Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Continued Examination Under 37 CFR 1.114
A request for continued examination (RCE) under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 17 February 2026 has been entered.
Priority
This application is a 371 of PCT/JP2021/007291 which claims the benefit of JP 2020-033525 with an effective filing date of 28 February 2020 as reflected in the filing receipt mailed on 05 January 2023.
Status of the Claims
Claims 1-18, 20, and 21 are pending.
Claims 1, 2, 7, and 11 are currently amended.
Claim 21 is new.
Claim 19 is currently cancelled.
Response to Amendments
Applicant’s amendments filed 17 February 2026 are acknowledged.
Claim Rejections - 35 USC § 112
Applicant’s amendments to claims 1, 7, and 11 and cancellation of claim 19 are sufficient to overcome the rejection of claims 1-20 under 35 U.S.C. 112(a) as failing to comply with the written description requirement. Claims 1, 7, and 11 have been amended to cancel the claim limitations that the specification does not provide support for a lower limit of more than 0% to 17.5% by mass for the content of the other components in the bottom liquid. The rejection is withdrawn.
Claim Rejections - 35 USC § 103
Applicant’s amendments to claims 1, 7, and 11 where limiting the treated liquid contents to 5% by mass or more is taught by Otsuka ‘287; however, adding the distillation residence time from claim 2 to claims 1 and 7 are not taught by Otsuka ‘287 and Sheely, and cancellation of claim 19 are sufficient to overcome the rejections of:
Claims 1, 3, 4, 6, 7, 17, and 18 under 35 U.S.C. 103 as being unpatentable over Otsuka et al. (US20020035287, cited by applicant 23 August 2022, hereinafter Otsuka ‘287) in view of Sheely (US3895050, cited by applicant 23 August 2022), as evidenced by Meili et al. (CN106892840, 27 June 2017, see machine translation);
Claims 2, 5, 12-16, and 19 under 35 U.S.C. 103 as being unpatentable over Otsuka et al. (US20020035287, cited by applicant 23 August 2022, hereinafter Otsuka ‘287) in view of Sheely (US3895050, cited by applicant 23 August 2022) and Ibi et al. (US20170217873, hereinafter Ibi);
Claims 8 and 10 under 35 U.S.C. 103 as being unpatentable over Otsuka et al. (US20020035287, cited by applicant 23 August 2022, hereinafter Otsuka ‘287) in view of Sheely (US3895050, cited by applicant 23 August 2022) and Prochazka et al. (US20110275869, hereinafter Prochazka); and,
Claims 9 and 20 under 35 U.S.C. 103 as being unpatentable over Otsuka et al. (US20020035287, cited by applicant 23 August 2022, hereinafter Otsuka ‘287) in view of Sheely (US3895050, cited by applicant 23 August 2022), Ibi et al. (US20170217873, hereinafter Ibi), and Prochazka et al. (US20110275869, hereinafter Prochazka).
Due to the amendments to claims 1 and 7 adding the distillation residence time from claim 2 to claims 1 and 7 not taught by Otsuka ‘287 and Sheely and cancellation of claim 19, the above rejections are withdrawn and a new ground(s) of rejection is/are provided below.
Applicant’s amendment to claim 11 limiting the treated liquid contents to 5% by mass or more is taught by Otsuka ‘287 and is not sufficient to overcome the rejection of claim 11 under 35 U.S.C. 103 as being unpatentable over Otsuka et al. (US20020035287, cited by applicant 23 August 2022, hereinafter Otsuka ‘287) in view of Poindexter (US5045156, cited by applicants 11 September 2013). The rejection is maintained; however, due solely to the amendment to claim 11 limiting the treated liquid contents to 5% by mass or more, an additional modified ground of rejection is provided below.
Double Patenting
Applicant’s amendment to claims 1, 7, and 11 where limiting the treated liquid contents to 5% by mass or more is taught by Otsuka ‘287; however, adding the distillation residence time from claim 2 to claims 1 and 7 are not taught by Otsuka ‘287 and Sheely, and cancellation of claim 19 are not sufficient to overcome the double patenting rejections of:
Claims 1-20 on the ground of nonstatutory double patenting as being unpatentable over claims 1-5 of U.S. Patent No. 6509490 to Otsuka et al. (hereinafter Otsuka ‘490) in view of in view of Otsuka et al. (JP2002097177, cited by applicant 23 August 2022, hereinafter Otsuka ‘177), Sheely (US3895050, cited by applicant 23 August 2022), Ibi et al. (US20170217873, hereinafter Ibi), Prochazka et al. (US20110275869, hereinafter Prochazka), and Poindexter (US5045156, cited by applicants 11 September 2013); and,
Claims 1-20 on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 2 of U.S. Patent No. 6646163 to Nakamura et al. (hereinafter Nakamura) in view of in view of Otsuka et al. (US20020035287, cited by applicant 23 August 2022, hereinafter Otsuka ‘287), Sheely (US3895050, cited by applicant 23 August 2022), Ibi et al. (US20170217873, hereinafter Ibi), Prochazka et al. (US20110275869, hereinafter Prochazka), and Poindexter (US5045156, cited by applicants 11 September 2013).
The rejections are maintained; however, due solely to the amendment to claims 1, 7, and 11 limiting the treated liquid contents to 5% by mass or more taught by Otsuka ‘287, adding the distillation residence time from claim 2 to claims 1 and 7 not taught by Otsuka ‘287 and Sheely, and cancellation of claim 19, an additional modified ground(s) of rejection is/are provided below.
Response to Arguments
Applicant’s arguments filed 17 February 2026 have been fully considered but they are not persuasive.
Applicant’s argue that Otsuka ‘287, Sheely, Ibi, Prochazka, and Poindexter do not disclose the limitations as recited in amended claims 1, 7, and 11. These arguments have been considered but are not persuasive for the reasons set forth in the new grounds of rejection below and the response to arguments below.
In response to applicant’s arguments throughout the remarks filed on 17 February 2026 that “Otsuka '287 does not disclose or suggest” “a distillation step in which a bottom liquid containing 5% by mass or more and 90% by mass or less of phthalonitriles and containing cyanobenzamides is obtained from the bottom of a high-boiling separation column, and in which the liquid residence time at the column bottom is set to 72 hours or less and the distillation pressure is set to 12 kPa or less”; and, a bottom liquid containing “5% by mass or more and 90% by mass or less of a phthalonitrile, a cyanobenzamide, and an organic solvent”.
Patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123.
Otsuka ‘287 is in the known prior art field of preventing the “loss of isophthalonitrile and plugging of a vacuum-evacuation system caused by isophthalonitrile migrating from a condensation system during distillation under reduced pressure” in order to produce “high-quality isophthalonitrile … at high yield constantly for a long period of time”, see Abstract; Paras. [0008]-[0009];[0039], where plugging in the line/pipe of condensed isophthalonitrile disturbs continuous operation, see Paras. [0008]-[0009];[0032];[0051]-[0052]; Fig. 1. Otsuka ‘287 also teaches “isophthalonitrile is unstable to heat and readily undergoes undesirable change or deterioration”, see Para. [0029].
Otsuka ‘287 teaches a distillation bottom liquid from “high-boiling-point impurity separation column C” contains 2% “unrecovered isophthalonitrile”, 2% to 6% “unrecovered isophthalonitrile”, and “a large amount of” “unrecovered isophthalonitrile”, see Paras. [0049]-[0052]; Fig. 1. Since “a prima facie case of obviousness exists” where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” and where the claimed ranges or amounts do not overlap with the prior art but are merely close, see MPEP 2144.05, one of ordinary skill in the art, before the effective filing date of the claimed invention, would be able to predictably determine the desirable amount of phthalonitrile in the bottom liquid from the high-boiling-point impurity separation column C of Otsuka ‘287, such as more than 5% by mass to less than 90% by mass, in order to prevent plugging in the line/pipe of condensed isophthalonitrile disturbing continuous operation, see Paras. [0008]-[0009];[0032];[0051]-[0052]; Fig. 1, meeting within the above bottom liquid phthalonitriles concentration.
Otsuka ‘287 teaches a liquid containing “m-tolunitrile (73.5 wt. %), isophthalonitrile (25 wt. %), cyanobenzamide (1 wt. %), and other components (0.5 wt. %)” is distilled in column C, see Paras. [0049]-[0050]. The top gaseous effluent from column C comprises “isophthalonitrile and the organic solvent”, i.e., m-tolunitrile (73.5 wt. %) and isophthalonitrile (25 wt. %), and “high-boiling-point impurities are discharged from the bottom”, i.e., cyanobenzamide (1 wt. %), and other components (0.5 wt. %), see Paras. [0024];[0037];[0049]-[0050], meeting the above bottom liquid containing cyanobenzamide.
Otsuka ‘287 teaches the distillation in column C is carried out at a pressure of 8 kPa, “preferably 5-10 kPa”, see Paras. [0031]-[0032];[0050], meeting within the above distillation pressure.
As stated on page 25 of the previous office action dated 17 November 2025 (hereinafter POA), “Otsuka ‘287 does not disclose adjusting the liquid residence time at the column bottom to 72 hours or less.” Ibi is provided to teach this limitation.
“A reference is analogous art to the claimed invention if: (1) the reference is from the same field of endeavor as the claimed invention (even if it addresses a different problem); or (2) the reference is reasonably pertinent to the problem faced by the inventor (even if it is not in the same field of endeavor as the claimed invention).”, see MPEP 2141.01(a).
Ibi is in the known prior art field of producing phthalonitriles from their corresponding xylenes with further purification by distillation, see Abstract; Paras. [0019];[0047]; Fig. 1; while, suppressing the condensation and clogging of phthalonitriles in the system, see Paras. [0035];[0053], and is applied to teach the same, where in order to prevent the formation of phthalonitrile isomers “a shorter residence time of” phthalonitrile in the bottom of the column is preferred, such as “180 minutes or less, more preferably 10 to 120 minutes, furthermore preferably 15 to 60 minutes, particularly preferably 20 to 30 minutes”, see Para. [0047].
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Otsuka ‘287 and Ibi both teach preventing condensation in phthalonitrile production system and lines in the phthalonitrile production industry, a person of ordinary skill in the art has good reason to modify the bottom liquid high-boiling point column residence time of Otsuka ‘287 by relying upon the bottom liquid high-boiling point column residence time of Ibi before the effective filing date of the claimed invention for knowledge generally available within the phthalonitrile production industry regarding bottom liquid residence time, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing a nitrile compound by pursuing the known options within their technical grasp, such as the distillation residence time for the limited production of specific by-products, for the benefit of producing a nitrile compound with efficiency and minimal environmental impact, see Ibi, Paras. [0047];[0078] and MPEP 2141.
For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to applicant’s arguments (a) on page 9 of the remarks filed on 17 February 2026 that “Otsuka '287 nor Sheely provides any teaching or motivation regarding the operating conditions of the distillation or the composition of the bottom liquid for the purpose of feeding the bottom liquid to an incinerator without clogging the piping while maintaining fluidity. Therefore, a person skilled in the art would not have been motivated to arrive at the present claims based on Otsuka '287 and Sheely.”
The test for obviousness is not whether the features of a secondary reference may be bodily incorporated into the structure of the primary reference; nor is it that the claimed invention must be expressly suggested in any one or all of the references. Rather, the test is what the combined teachings of the references would have suggested to those of ordinary skill in the art, see In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981) and MPEP 2145.
“A reference is analogous art to the claimed invention if: (1) the reference is from the same field of endeavor as the claimed invention (even if it addresses a different problem); or (2) the reference is reasonably pertinent to the problem faced by the inventor (even if it is not in the same field of endeavor as the claimed invention).”, see MPEP 2141.01(a).
As stated above, Otsuka ‘287 is in the known prior art field of preventing the “loss of isophthalonitrile and plugging of a vacuum-evacuation system caused by isophthalonitrile migrating from a condensation system during distillation under reduced pressure” in order to produce “high-quality isophthalonitrile … at high yield constantly for a long period of time”, see Abstract; Paras. [0008]-[0009];[0039], where plugging in the line/pipe of condensed isophthalonitrile disturbs continuous operation, see Paras. [0008]-[0009];[0032];[0051]-[0052]; Fig. 1. Otsuka ‘287 also teaches “isophthalonitrile is unstable to heat and readily undergoes undesirable change or deterioration”, see Para. [0029].
Sheely is in the known prior art field of an improved method of recovering condensed materials from the effluents of reactions for producing tolunitrile, phthalonitrile, iso- and terephthalonitrile from the xylene isomers, whereby said materials may be ultimately disposed of by incineration, see Col. 2, Lns. 7-63; Col. 3, Lns. 3-14; Col. 4, Lns. 42-57; Col. 11, Lns. 9-68; Fig. 1, and is applied to teach the same, where “[c]ondensed polymer by-products and catalyst fines (if present in the reactor effluent) are removed from the bottom of the quench column via line 11 in a relatively small stream of unvaporized solvent. Although not shown, it is to be understood that the quench column bottoms may be treated to recover the catalyst fines and hydrocarbon solvent for reuse in the system. The polymer by-products may be disposed of by incineration”, see Col. 4, Lns. 42-57.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Otsuka ‘287 and Sheely both teach preventing condensation in phthalonitrile production lines in the phthalonitrile production industry, a person of ordinary skill in the art has good reason to modify the bottom liquid high-boiling point column effluent of Otsuka ‘287 by relying upon the bottom liquid high-boiling point column effluent waste disposal incineration of Sheely before the effective filing date of the claimed invention for knowledge generally available within the phthalonitrile production industry regarding bottom liquid waste disposal, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing a nitrile compound by pursuing the known options within their technical grasp, such as the recovery of process materials and the combustion of condensed material by-products, for the benefit of producing a nitrile compound with efficiency and minimal environmental impact, see Sheely, Col. 2, Ln. 48-Col. 3, Ln. 54 and MPEP 2141.
For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to applicant’s arguments (b) on page 10 of the remarks filed on 17 February 2026 that the column bottom distillation residence time, distillation pressure, and phthalonitrile content in the bottom liquid “achieves remarkable effects”. The fact that the inventor has recognized another advantage which would flow naturally from following the suggestion of the prior art cannot be the basis for patentability when the differences would otherwise be obvious, see Ex parte Obiaya, 227 USPQ 58, 60 (Bd. Pat. App. & Inter. 1985). In addition, “[t]o establish unexpected results over a claimed range, applicants should compare a sufficient number of tests both inside and outside the claimed range to show the criticality of the claimed range.” In re Hill, 284 F.2d 955, 128 USPQ 197 (CCPA 1960), see MPEP 716.02(d). Instant specification, Table 1 does not provide tests at a pressure of above 12 Kpa and a phthalonitrile content of above 90% by mass; therefore, applicants have not provided a comparison to the closest prior art and tests inside and outside the limitations of the above critical parameters to support their argument of remarkable effects, surprising, and unexpected results, see MPEP 716.02(e).
For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to applicant’s arguments (c) on page 10 of the remarks filed on 17 February 2026 that “while the specification does not explicitly use the phrase “preventing piping clogging,” paragraphs [0080] and [0081] of the specification clearly support this effect. For instance, see paragraph [0080], which explicitly states that “closure of the piping can be avoided.” In the POA there was no rejection based upon applicant’s use of the terms “preventing piping clogging”. The examiner herein acknowledges that applicant’s terms of “preventing piping clogging” is understood to refer to “closure of the piping”.
In response to applicant’s arguments:
(a) on pages 11-12 of the remarks filed on 17 February 2026 that “Otsuka '287 and Poindexter differ in their technical concepts regarding the composition of the bottom liquid withdrawn from the column, and thus, a person skilled in the art would not combine Poindexter's teachings with Otsuka '287”, “a person skilled in the art would not be motivated to combine Poindexter's teachings with Otsuka '287 due to these divergent technical objectives”; and,
(b) on page 13 of the remarks filed on 17 February 2026 that “Otsuka '287 does not describe feeding the bottom liquid to an incinerator while maintaining fluidity without clogging the piping, nor does it disclose any specific composition of the bottom liquid. Similarly, Poindexter does not disclose these distinguishing features”.
Applicant’s argue limitations that are not presented in claim 11, such as “the addition of extra solvent to the isophthalonitrile capture liquid” and “clogging the piping”. Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims, see In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993) and MPEP 2111.01.
As stated on pages 39-40 of the POA, “Otsuka ‘287 does not disclose subjecting a treated liquid to combustion while maintaining the treated liquid in a liquid state.” Poindexter is provided to teach this limitation. Poindexter is not applied to teach the claim 11 treated liquid or its composition.
To clarify, the claim 11 preamble “for producing a phthalonitrile by an ammoxidation reaction” may be interpreted as intended use since “the body of a claim fully and intrinsically sets forth all of the limitations of the claimed invention, and the preamble merely states, for example, the purpose or intended use of the invention, rather than any distinct definition of any of the claimed invention’s limitations, then the preamble is not considered a limitation and is of no significance to claim construction. Shoes by Firebug LLC v. Stride Rite Children’s Grp., LLC, 962 F.3d 1362, 2020 USPQ2d 10701 (Fed. Cir. 2020)”, see MPEP 2111.02 II. Therefore, the preamble statement may not be considered a claim limitation.
“A reference is analogous art to the claimed invention if: (1) the reference is from the same field of endeavor as the claimed invention (even if it addresses a different problem); or (2) the reference is reasonably pertinent to the problem faced by the inventor (even if it is not in the same field of endeavor as the claimed invention).”, see MPEP 2141.01(a).
As stated above and on pages 38-39 of the POA, Otsuka ‘287 teaches the method and the contents of the treated liquid. Otsuka ‘287 further teaches “a mixture containing a sublimable high-melting-point substance is subjected to distillation, the interior temperature of the distillation column is elevated to a temperature not lower than the melting point of the substance, to thereby prevent plugging caused by deposition of crystals … in the case in which a sublimable high-melting-point substance and a solvent in an amount sufficient for dissolving the sublimable high-melting-point substance are together placed in the distillation column, deposition of crystals does not occur even through the operation temperature is not higher than the melting point of the substance. The distribution of isophthalonitrile concentration in a distillation column is determined in accordance with the composition of supplied liquid, conditions for distillation and separation of the bottom residue, and vapor-liquid equilibrium conditions, and the temperature profile varies in accordance with operation pressure.”, see Paras. [0009];[0031]-[0033]. Therefore, Otsuka ‘287 teaches it is advantageous to incorporate an organic solvent in the distillation column in order to prevent condensation plugging.
Poindexter is in the known prior art field of increasing “isophthalonitrile yield” by fluidizing the distillation bottoms in order to prevent condensation/precipitation and clogging in the system and pipes “due to foulant accumulation”, see Abstract; Col. 1, Lns. 6-44, as is applied to teach the same, where an amount of crude isophthalonitrile is left in the bottom of the high boiling point distillation column and an amount is mixed with a hydrocarbon liquid solvent in order to “solubilize solid impurities formed during the distillation process and which impurities are removed from the distillation column for disposal”, where the bottom stream effluent is “easily pumped to an incinerator for disposal”, see Col. 1, Ln. 45-Col. 2, Ln. 5.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Otsuka ‘287 and Poindexter both teach preventing condensation in phthalonitrile production lines and the condensation is related to the concentration of the phthalonitrile in the phthalonitrile production line, a person of ordinary skill in the art has good reason to modify the bottom liquid high-boiling point column effluent of Otsuka ‘287 by relying upon the bottom liquid high-boiling point column effluent waste disposal incineration of Poindexter before the effective filing date of the claimed invention for knowledge generally available within the phthalonitrile production industry regarding bottom liquid waste disposal, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing a nitrile compound by pursuing the known options within their technical grasp, such as combustion of by-products, for the benefit of producing a nitrile compound with efficiency and minimal environmental impact, see Poindexter, Col. 1, Lns. 35-44 and MPEP 2141.
Double Patenting
Applicant’s arguments on pages 13-14 of the remarks filed on 27 February 2026 that the claims are distinguished from US 6509490 to Otsuka et al. and US 6646163 to Nakamura et al. have been considered but are not persuasive for the reasons set forth in the Double Patenting rejections detailed in the POA, the response to arguments above, and in the new grounds of rejection below.
New, Maintained, and Modified Rejections Based on the RCE and Amendments to the Claims filed on 17 February 2026
For clarity between the new, modified, and maintained rejections, the specific modifications in the maintained rejections are in italics.
In the Spirit of Compact Prosecution
Throughout prosecution the examiner has attempted to identify all objections and clarity issues amongst the claims, applicant is advised that some objections and clarity issues may still remain. Going forward, the examiner respectfully requests applicant to perform a detailed review of the claims regarding clarity, grammar, antecedent basis, word spacing, and spelling issues.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim 11 stands rejected in modified form under 35 U.S.C. 103 as being unpatentable over Otsuka et al. (US20020035287, published 21 March 2002, hereinafter Otsuka ‘287) in view of Poindexter (US5045156, patented 03 September 1991).
Otsuka ‘287 is in the known prior art field of preventing the “loss of isophthalonitrile and plugging of a vacuum-evacuation system caused by isophthalonitrile migrating from a condensation system during distillation under reduced pressure” in order to produce “high-quality isophthalonitrile … at high yield constantly for a long period of time”, see Abstract; Paras. [0008]-[0009];[0039], where plugging in the line/pipe of condensed isophthalonitrile disturbs continuous operation, see Paras. [0008]-[0009];[0032];[0051]-[0052]; Fig. 1. Otsuka ‘287 also teaches “isophthalonitrile is unstable to heat and readily undergoes undesirable change or deterioration”, see Para. [0029].
Claim 11 Otsuka ‘287 teaches a method for producing a phthalonitrile by an ammoxidation reaction (Paras. [0046]-[0050, Example 1), the method comprising:
wherein the treated liquid comprises 90% by mass or less of a phthalonitrile, acyanobenzamide, and an organic solvent (Paras. [0049]-[0050], “After completion of trapping, the liquid was found to have the following composition; i.e., m-tolunitrile (73.5 wt. %), isophthalonitrile (25 wt. %), cyanobenzamide (1 wt. %), and other components (0.5 wt. %). … The percent recovery of isophthalonitrile including isophthalonitrile contained in a fraction from which the high-boiling-point impurity had been separated was 98%. In other words, the high-boiling-point impurity included 2% unrecovered isophthalonitrile.”; Figure 1, column D where solvent is recovered from the top, i.e., the residue of column C has about “2% unrecovered isophthalonitrile”, less than “m-tolunitrile (73.5 wt. %)”, “cyanobenzamide (1 wt. %), and other components (0.5 wt. %)”, which equates to less than 76.5 wt.% phthalonitrile, a cyanobenzamide, and an organic solvent). [deletions]
The distillation bottom liquid from “high-boiling-point impurity separation column C” contains 2% “unrecovered isophthalonitrile”, 2% to 6% “unrecovered isophthalonitrile”, and “a large amount of” “unrecovered isophthalonitrile”, see Paras. [0049]-[0052]; Fig. 1. Since “a prima facie case of obviousness exists” where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” and where the claimed ranges or amounts do not overlap with the prior art but are merely close, see MPEP 2144.05, one of ordinary skill in the art, before the effective filing date of the claimed invention, would be able to predictably determine the desired “distribution of isophthalonitrile concentration” in the distillation column bottom liquid from the high-boiling-point impurity separation column C of Otsuka ‘287, such as more than 5% by mass to less than 90% by mass, for the purpose of preventing plugging in the line/pipe of condensed isophthalonitrile disturbing continuous operation, see Paras. [0008]-[0009];[0032];[0051]-[0052]; Fig. 1, meeting within the liquid phthalonitriles bottom effluent concentration in instant application claim 11.
The claim 11 preamble “for producing a phthalonitrile by an ammoxidation reaction” may be interpreted as intended use since “the body of a claim fully and intrinsically sets forth all of the limitations of the claimed invention, and the preamble merely states, for example, the purpose or intended use of the invention, rather than any distinct definition of any of the claimed invention’s limitations, then the preamble is not considered a limitation and is of no significance to claim construction. Shoes by Firebug LLC v. Stride Rite Children’s Grp., LLC, 962 F.3d 1362, 2020 USPQ2d 10701 (Fed. Cir. 2020)”, see MPEP 2111.02 II. Therefore, the preamble statement is not considered a claim limitation.
Otsuka ‘287 does not teach subjecting a treated liquid to combustion while maintaining the treated liquid in a liquid state.
Poindexter in the field of “a product which substituted in whole or in part for IPN during the distillation which would increase the recovery of IPN from the bottoms and keep the bottoms fluid and pumpable for disposal by incineration” (Col. 1, Lns. 35-44) teaches subjecting a treated liquid to combustion while maintaining the treated liquid in a liquid state (Col. 1, Ln. 46-Col. 2, Ln. 5, “The improvement of this invention comprises substituting from 1 to 50% by weight of the crude IPN feed to the column, a substantially aromatic free hydrocarbon liquid having an initial boiling point between 570° to 750° F. and continuing the distillation whereby the hydrocarbon liquid replaces the IPN used to solubilize the impurities thereby increasing the yield of distilled IPN recovered from the column. A high boiling, non-aromatic solvent found to be unreactive towards IPN in laboratory testing is described in Table 1. During a field trial, the additive kept the bottoms stream fluid demonstrating that the residue could be easily pumped to an incinerator for disposal.”).
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to have modified the process of Otsuka ‘287 with the combustion teachings of Poindexter with a reasonable predictability of success. By applying “routine optimization” and “predictable results” to select the optimal combustion, as taught by Poindexter, one of ordinary skill in the art would have been motivated to make these modifications because Poindexter provides a finite number of identified, predictable solutions, and a person of ordinary skill in the art has good reason to efficiently produce a nitrile compound by pursuing the known options within their technical grasp, such as combustion of by-products, for the benefit of producing a nitrile compound with efficiency and minimal environmental impact (Otsuka ‘287, Para. [0029], “in order to obtain isophthalonitrile at high yield, separation of high-boiling-point impurities must be performed as rapidly as possible and at as low a temperature as possible”; Poindexter, Col. 1, Lns. 35-44, “a product which substituted in whole or in part for IPN during the distillation which would increase the recovery of IPN from the bottoms and keep the bottoms fluid and pumpable for disposal by incineration … Furthermore, the product would reduce maintenance costs by eliminating shutdowns due to foulant accumulation and increase production by increasing operating utility.”). See MPEP 2141.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Otsuka ‘287 and Poindexter both teach preventing condensation in phthalonitrile production lines and the condensation is related to the concentration of the phthalonitrile in the phthalonitrile production line, a person of ordinary skill in the art has good reason to modify the bottom liquid high-boiling point column effluent of Otsuka ‘287 by relying upon the bottom liquid high-boiling point column effluent waste disposal incineration of Poindexter before the effective filing date of the claimed invention for knowledge generally available within the phthalonitrile production industry regarding bottom liquid waste disposal, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing a nitrile compound by pursuing the known options within their technical grasp, such as combustion of by-products, for the benefit of producing a nitrile compound with efficiency and minimal environmental impact, see Poindexter, Col. 1, Lns. 35-44 and MPEP 2141.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied, 426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design incentives and other market forces can prompt variations of it, either in the same field or a different one. If a person of ordinary skill can implement a predictable variation, § 103 likely bars its patentability. For the same reason, if a technique has been used to improve one device, and a person of ordinary skill in the art would recognize that it would improve similar devices in the same way, using the technique is obvious unless its actual application is beyond his or her skill”. See MPEP 2141.
In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929) states “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions, or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means,” such as quantifying the exact proportion of materials in the high-boiling point impurities, “is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions”.
“The discovery of a previously unappreciated property of a prior art composition,” such as quantifying the exact proportion of materials in the high-boiling point impurities, “or of a scientific explanation for the prior art’s functioning, does not render the old composition patentably new to the discoverer” and “the claiming of a new use, new function or unknown property which is inherently present in the prior art does not necessarily make the claim patentable”, see MPEP 2112 I.
Claims 1-7, 11-18, and 21 are newly rejected under 35 U.S.C. 103 as being unpatentable over Otsuka et al. (US20020035287, published 21 March 2002, hereinafter Otsuka ‘287) in view of Sheely (US3895050, published 15 July 1975) and in further view of Ibi et al. (US20170217873, published 03 August 2017, hereinafter Ibi).
Otsuka ‘287 is in the known prior art field of preventing the “loss of isophthalonitrile and plugging of a vacuum-evacuation system caused by isophthalonitrile migrating from a condensation system during distillation under reduced pressure” in order to produce “high-quality isophthalonitrile … at high yield constantly for a long period of time”, see Abstract; Paras. [0008]-[0009];[0039], where plugging in the line/pipe of condensed isophthalonitrile disturbs continuous operation, see Paras. [0008]-[0009];[0032];[0051]-[0052]; Fig. 1. Otsuka ‘287 also teaches “isophthalonitrile is unstable to heat and readily undergoes undesirable change or deterioration”, see Para. [0029].
Regarding instant application claims 1, 6, and 16-18, Otsuka ‘287 teaches a method for producing a purified phthalonitrile by separating isophthalonitrile from a gas produced by causing m-xylene to react with ammonia and oxygen-containing gas in the presence of a catalyst, … and the organic solvent is recovered from the top of the rectification column and liquefied isophthalonitrile of high purity is recovered at the bottom of the column”, see Abstract; Fig. 1; Paras. [0045]-[0050], the method comprising: reacting ammonia, oxygen, and xylene in the presence of a catalyst in “an ammoxidation reactor A" to obtain a reaction product gas comprising a phthalonitrile and a cyanobenzamide, see Paras. [0035]-[0036];[0045]-[0050]; Fig. 1, that is then sent to an isophthalonitrile trapping column B, where a trapping step where “the gas produced through the aforementioned ammoxidation was subjected to a trapping process” by “bringing the gas into contact with an organic solvent having a boiling point lower than that of isophthalonitrile” “for two hours by use of m-tolunitrile (2 kg) charged into the trapping column and heated to 175° C., to thereby trap components. After completion of trapping, the liquid was found to have the following composition; i.e., m-tolunitrile (73.5 wt. %), isophthalonitrile (25 wt. %), cyanobenzamide (1 wt. %), and other components (0.5 wt. %).”, i.e., the trapping liquid includes all of the contents of the gas, see Paras. [0012];[0015];[0049]; Fig. 1, meeting:
The method for producing, the reactants, the reacting, and the contents of the gas produced in instant application claim 1;
The contacting with a solvent within the boiling point range and obtaining a liquid in instant application claim 1; and,
The specific isophthalonitrile in instant application claim 6, in instant application claim 16, in instant application claim 17, and in instant application claim 18.
After trapping column B, the liquid is “supplied to a middle stage plate of a high-boiling-point impurity separation column C” having a column top and a column bottom, see Para. [0050]; Fig. 1, where the distillation in column C is carried out at a pressure of 8 kPa, “preferably 5-10 kPa”, see Paras. [0031]-[0032];[0050]. The liquid containing “m-tolunitrile (73.5 wt. %), isophthalonitrile (25 wt. %), cyanobenzamide (1 wt. %), and other components (0.5 wt. %)” is distilled in column C, see Paras. [0049]-[0050], where the top gaseous effluent from column C comprises “isophthalonitrile and the organic solvent”, i.e., m-tolunitrile (73.5 wt. %) and isophthalonitrile (25 wt. %), and “high-boiling-point impurities are discharged from the bottom”, i.e., cyanobenzamide (1 wt. %), and other components (0.5 wt. %), see Paras. [0024];[0037];[0049]-[0050], meeting the distilling high boiling components, the top gaseous components, the bottom liquid effluent having cyanobenzamide, and within the distillation pressure range in instant application claim 1.
The distillation bottom liquid from “high-boiling-point impurity separation column C” contains 2% “unrecovered isophthalonitrile”, 2% to 6% “unrecovered isophthalonitrile”, and “a large amount of” “unrecovered isophthalonitrile”, see Paras. [0049]-[0052]; Fig. 1. Since “a prima facie case of obviousness exists” where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” and where the claimed ranges or amounts do not overlap with the prior art but are merely close, see MPEP 2144.05, one of ordinary skill in the art, before the effective filing date of the claimed invention, would be able to predictably determine the desired “distribution of isophthalonitrile concentration” in the distillation column bottom liquid from the high-boiling-point impurity separation column C of Otsuka ‘287, such as more than 5% by mass to less than 90% by mass, for the purpose of preventing plugging in the line/pipe of condensed isophthalonitrile disturbing continuous operation, see Paras. [0008]-[0009];[0032];[0051]-[0052]; Fig. 1, meeting within the liquid phthalonitriles bottom effluent concentration in instant application claim 1.
From “high-boiling-point impurity separation column C”, “isophthalonitrile and the organic solvent are recovered from the top, and high-boiling-point impurities are discharged from the bottom. The recovered isophthalonitrile and the organic solvent are transferred to a rectification column D. The organic solvent is recovered from the top of the column, while isophthalonitrile is recovered from the bottom of the column.”, see Paras. [0037];[0050]; Fig. 1, meeting the removing the organic solvent and purifying phthalonitrile in instant application claim 1.
In addition, the instant application claim 1 scope is not limited by claim language that suggests or makes optional but does not require steps to be performed, or by claim language that does not limit a claim to a particular structure, see MPEP 2111.04. In this case, since the “or less” implies a lower limit of zero, the “wherein” clause drawn to adjusting the residence time and pressure appears to not give “meaning and purpose to the manipulative steps”, see MPEP 2111.04.
Furthermore, the residence time of “72 hours or less” with a lower limit of no/zero residence time, renders the distillation step optional, see MPEP 2111.
Regarding instant application claim 2, Otsuka ‘287 teaches distillation in column C is “performed at a top pressure of 8 kPa, a top temperature of 164° C., and a bottom temperature of 204° C.”, see Para. [0050], meeting within the temperature range in instant application claim 2.
Regarding instant application claims 3, 4, and 12, Otsuka ‘287 teaches the process is a continuous process, see Paras. [0045]-[0050], Example 1; Fig. 1 depicts a continuous operation; Para. [0051], “disturbing continuous operation”, i.e., Comparative Example 1 disturbed continuous operation; therefore, the process of Otsuka ‘287 Example 1 is continuous, where m-tolunitrile is the solvent that is part of the “gas produced through distillation carried out in the high-boiling-point impurity separation column C was supplied to a rectification column D” then the “organic solvent is recovered from the top of the column, while isophthalonitrile is recovered from the bottom of the column”, see Paras. [0024];[0032];[0037];[0050], meeting:
The continuous reacting, contacting, distilling and removing in instant application claim 3 and in instant application claim 12; and,
The solvent is m-tolunitrile in instant application claim 4.
Regarding instant application claims 7, 11, and 21, Otsuka ‘287 teaches a method for producing a purified phthalonitrile by separating isophthalonitrile from a gas produced by causing m-xylene to react with ammonia and oxygen-containing gas in the presence of a catalyst, … and the organic solvent is recovered from the top of the rectification column and liquefied isophthalonitrile of high purity is recovered at the bottom of the column”, see Abstract; Fig. 1; Paras. [0045]-[0050], the method comprising: reacting ammonia, oxygen, and xylene in the presence of a catalyst in “an ammoxidation reactor A" to obtain a reaction product gas comprising a phthalonitrile and a cyanobenzamide, see Paras. [0035]-[0036];[0045]-[0050]; Fig. 1, that is then sent to an isophthalonitrile trapping column B, where a trapping step where “the gas produced through the aforementioned ammoxidation was subjected to a trapping process” by “bringing the gas into contact with an organic solvent having a boiling point lower than that of isophthalonitrile” “for two hours by use of m-tolunitrile (2 kg) charged into the trapping column and heated to 175° C., to thereby trap components. After completion of trapping, the liquid was found to have the following composition; i.e., m-tolunitrile (73.5 wt. %), isophthalonitrile (25 wt. %), cyanobenzamide (1 wt. %), and other components (0.5 wt. %).”, i.e., the trapping liquid includes all of the contents of the gas, see Paras. [0012];[0015];[0049]; Fig. 1, meeting:
The method for purifying and the contents of the gas produced in instant application claim 7;
The method for producing in instant application claim 11;
The bottom liquid, the reacting, the reactants, and the reactant product contents in instant application claim 21; and,
The contacting with a solvent within the boiling point range and obtaining a liquid in instant application claim 7 and in instant application claim 21.
After trapping column B, the liquid is “supplied to a middle stage plate of a high-boiling-point impurity separation column C” having a column top and a column bottom, see Para. [0050]; Fig. 1, where the distillation in column C is carried out at a pressure of 8 kPa, “preferably 5-10 kPa”, see Paras. [0031]-[0032];[0050]. The liquid containing “m-tolunitrile (73.5 wt. %), isophthalonitrile (25 wt. %), cyanobenzamide (1 wt. %), and other components (0.5 wt. %)” is distilled in column C, see Paras. [0049]-[0050], where the top gaseous effluent from column C comprises “isophthalonitrile and the organic solvent”, i.e., m-tolunitrile (73.5 wt. %) and isophthalonitrile (25 wt. %), and “high-boiling-point impurities are discharged from the bottom”, i.e., cyanobenzamide (1 wt. %), and other components (0.5 wt. %), see Paras. [0024];[0037];[0049]-[0050], meeting:
The distilling high boiling components, the top gaseous components, and within the distillation pressure range in instant application claim 7 and in instant application claim 21; and,
The bottom liquid effluent having cyanobenzamide in instant application claim 7 and in instant application claim 21.
The distillation bottom liquid from “high-boiling-point impurity separation column C” contains 2% “unrecovered isophthalonitrile”, 2% to 6% “unrecovered isophthalonitrile”, and “a large amount of” “unrecovered isophthalonitrile”, see Paras. [0049]-[0052]; Fig. 1. Since “a prima facie case of obviousness exists” where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” and where the claimed ranges or amounts do not overlap with the prior art but are merely close, see MPEP 2144.05, one of ordinary skill in the art, before the effective filing date of the claimed invention, would be able to predictably determine the desired “distribution of isophthalonitrile concentration” in the distillation column bottom liquid from the high-boiling-point impurity separation column C of Otsuka ‘287, such as more than 5% by mass to less than 90% by mass, for the purpose of preventing plugging in the line/pipe of condensed isophthalonitrile disturbing continuous operation, see Paras. [0008]-[0009];[0032];[0051]-[0052]; Fig. 1, meeting within the liquid phthalonitriles bottom effluent/treated liquid concentration in instant application claim 7, in instant application claim 11, and in instant application claim 21.
From “high-boiling-point impurity separation column C”, “isophthalonitrile and the organic solvent are recovered from the top, and high-boiling-point impurities are discharged from the bottom. The recovered isophthalonitrile and the organic solvent are transferred to a rectification column D. The organic solvent is recovered from the top of the column, while isophthalonitrile is recovered from the bottom of the column.”, see Paras. [0037];[0050]; Fig. 1, meeting the removing the organic solvent and purifying phthalonitrile in instant application claim 7.
In addition, the instant application claims 7 and 21 scope is not limited by claim language that suggests or makes optional but does not require steps to be performed, or by claim language that does not limit a claim to a particular structure, see MPEP 2111.04. In this case, since the “or less” implies a lower limit of zero, the “wherein” clause drawn to adjusting the residence time and pressure appears to not give “meaning and purpose to the manipulative steps”, see MPEP 2111.04.
Furthermore in instant application claims 7 and 21, the residence time of “72 hours or less” with a lower limit of no/zero residence time, renders the distillation step optional, see MPEP 2111.
Otsuka ‘287 does not teach:
The instant application claims 1, 7, and 11 limitations of combusting the bottom liquid, while maintaining the bottom liquid in a liquid state;
The instant application claims 1, 7, and 21 limitations of wherein in the distilling, the liquid residence time at the column bottom is adjusted to 72 hours or less;
The claims 3 and 12 limitations of continuous combusting, the reaction product gas further comprises a tolunitrile, and the recovered tolunitrile is used as the organic solvent; and,
The limitations of instant application claims 5 and 13-15.
Sheely is in the known prior art field of an improved method of recovering condensed materials from the effluents of reactions for producing tolunitrile, phthalonitrile, iso- and terephthalonitrile from the xylene isomers, whereby said materials may be ultimately disposed of by incineration, see Col. 2, Lns. 7-63; Col. 3, Lns. 3-14; Col. 4, Lns. 42-57; Col. 11, Lns. 9-68; Fig. 1, and is applied to teach the same.
Regarding instant application claims 1, 7, and 11, Sheely teaches “[c]ondensed polymer by-products and catalyst fines (if present in the reactor effluent) are removed from the bottom of the quench column via line 11 in a relatively small stream of unvaporized solvent. Although not shown, it is to be understood that the quench column bottoms may be treated to recover the catalyst fines and hydrocarbon solvent for reuse in the system. The polymer by-products may be disposed of by incineration”, see Col. 4, Lns. 42-57, where “the dilute water solution of the ammonia salt issuing from the bottom of the quench tower typically contains some acrylonitrile and other reaction products but is contaminated with organic heavies such as carbonyl polymers, hydrolyzed polyacrylonitrile, polyacrylamide, and cyanoethylated side reaction products”, see Col. 2, Lns. 7-47. Figs. 1 and 2 depict lines passing to incinerator 36, “where ammonia, HCN, acetonitrile, propionitrile and any uncondensed hydrocarbon solvent furnish the necessary fuel values”, see Figs. 1-2; Col. 5, Lns. 43-47; Col. 10, Ln. 53-Col. 11, Ln. 8, i.e., the bottom liquid effluent remains a liquid until passed to the incinerator where the effluent is used to generate heat and disposed of in the incinerator, meeting combusting the bottom liquid, while maintaining the bottom liquid in a liquid state in instant application claim 1, in instant application claim 7, and in instant application claim 11.
Regarding instant application claims 3 and 12, Sheely teaches Figs. 1 and 2 depicting a continuous process, see Figs. 1-2, where “water is continually recovered and recycled and since hydrocarbon solvent is available for quenching purposes, polymer by-products and entrained catalyst particles are removed almost entirely from the reactor effluent in the quench column, and fuel values in the off-gases passed to the incinerator can be controlled to within close limits … and recovery of bottoms that may be disposed of by incineration rather than by biological treatment. Since incineration may be conducted so as to obtain complete combustion. the incinerator output can be controlled so as to meet governmental standards as to carbon monoxide content. Furthermore, the rate of solvent loss can be limited to what is required to satisfy incinerator fuel requirements.”, see Col. 10, Ln. 53-Col. 11, Ln. 8. The reaction product gas further comprises a tolunitrile, see Col. 11, Lns. 9-68, and the recovered solvent is used as the organic solvent, see Col. 3, Lns. 45-48, where “[a]lthough not shown, it is to be understood that the quench column bottoms may be treated to recover the catalyst fines and hydrocarbon solvent for reuse in the system.”, see Col. 4, Lns. 52-57, meeting continuous combusting, the reaction product gas further comprises a tolunitrile, and the recovered tolunitrile is used as the organic solvent in instant application claim 3 and in instant application claim 12.
Ibi is in the known prior art field of producing phthalonitriles from their corresponding xylenes with further purification by distillation, see Abstract; Paras. [0019];[0047]; Fig. 1; while, suppressing the condensation and clogging of phthalonitriles in the system, see Paras. [0035];[0053], and is applied to teach the same.
Regarding instant application claims 1, 7, and 21, Ibi teaches in order to prevent the formation of phthalonitrile isomers “a shorter residence time of” phthalonitrile in the bottom of the column is preferred, such as “180 minutes or less, more preferably 10 to 120 minutes, furthermore preferably 15 to 60 minutes, particularly preferably 20 to 30 minutes”, see Para. [0047], meeting within the residence time range in instant application claim 1, in instant application claim 7, and in instant application claim 21.
Regarding instant application claims 5 and 13-15, Ibi teaches “ammoxidation reaction gas extracted from the top of the ammoxidation reactor A was introduced to an isophthalonitrile absorption column B, so that isophthalonitrile in the ammoxidation reaction gas was absorbed in the meta-tolunitrile”, where after absorption the liquid containing the product gas from the ammoxidation reaction includes “24.98% by mass of isophthalonitrile, 73.89% by mass of meta-tolunitrile, and 0.467% by mass of 3-cyanobenzamide, and 0.156% by mass of 3-cyanobenzoic acid”, see Paras. [0072]-[0074], meeting the cyanobenzamide is 3-cyanobenzamide in instant application claim 5, in instant application claim 13, in instant application claim 14, and in instant application claim 15.
In reference to the above claims, as stated above, “a prima facie case of obviousness exists” where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” and where the claimed ranges or amounts do not overlap with the prior art but are merely close, see MPEP 2144.05, one of ordinary skill in the art, before the effective filing date of the claimed invention, would be able to predictably determine the desired “distribution of isophthalonitrile concentration” in the distillation column bottom liquid from the high-boiling-point impurity separation column C of Otsuka ‘287, such as more than 5% by mass to less than 90% by mass, for the purpose of preventing plugging in the line/pipe of condensed isophthalonitrile disturbing continuous operation, see Otsuka ‘287, Paras. [0008]-[0009];[0032];[0051]-[0052]; Fig. 1.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified the bottom liquid high-boiling point column effluent of Otsuka ‘287 by relying upon the bottom liquid high-boiling point column effluent waste disposal incineration, recovery, and recycle of process reactants of Sheely with a reasonable predictability of success for the purpose of efficiently producing a nitrile compound by pursuing the known options within their technical grasp, such as the recovery of process materials and the combustion of condensed material by-products, for the benefit of producing a nitrile compound with efficiency and minimal environmental impact, see Sheely, Col. 2, Ln. 48-Col. 3, Ln. 54.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified the bottom liquid high-boiling point column residence time of Otsuka ‘287 by relying upon the bottom liquid high-boiling point column residence time and specific reaction products of Ibi with a reasonable predictability of success for the purpose of efficiently producing a nitrile compound by pursuing the known options within their technical grasp, such as the distillation residence time for the limited production of specific by-products, for the benefit of producing a nitrile compound with efficiency and minimal environmental impact, see Ibi, Paras. [0047];[0078].
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Otsuka ‘287, Sheely, and Ibi all teach preventing condensation in phthalonitrile production lines in the phthalonitrile production industry, a person of ordinary skill in the art has good reason to modify the bottom liquid high-boiling point column effluent, column bottom residence time, and the recovery and recycle of reactants and products of Otsuka ‘287 by relying upon the bottom liquid high-boiling point column effluent waste disposal incineration, recovery, and recycle of process reactants of Sheely and the bottom liquid high-boiling point column residence time and specific reaction products of Ibi before the effective filing date of the claimed invention for knowledge generally available within the phthalonitrile production industry art, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing a nitrile compound by pursuing the known options within their technical grasp, such as the recovery of process materials and the combustion of condensed material by-products, for the benefit of producing a nitrile compound with efficiency and minimal environmental impact, see Sheely, Col. 2, Ln. 48-Col. 3, Ln. 54; Ibi, Paras. [0047];[0078]; and, MPEP 2141.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied, 426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design incentives and other market forces can prompt variations of it, either in the same field or a different one. If a person of ordinary skill can implement a predictable variation, § 103 likely bars its patentability. For the same reason, if a technique has been used to improve one device, and a person of ordinary skill in the art would recognize that it would improve similar devices in the same way, using the technique is obvious unless its actual application is beyond his or her skill”, see MPEP 2141.
Selection of a known material, such as the specific cyanobenzamide by-product and tolunitrile solvent based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945). See MPEP 2144.07.
In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929) states “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions, or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means,” such as quantifying the exact proportion of materials in the high-boiling point impurities, “is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions”.
In addition, “[w]here applicant claims a composition in terms of a function, property or characteristic and the composition of the prior art is the same as that of the claim but the function is not explicitly disclosed by the reference, the examiner may make a rejection under both 35 U.S.C. 102 and 103.”, see MPEP 2112 III. In this case, Otsuka ‘287 teaches an ammoxidation reaction with the same starting reactants as instantly claimed to produce a phthalonitrile and a cyanobenzamide, see Otsuka ‘287, Para. [0049], the cyanobenzamide produced by Otsuka ‘287 may also inherently contain “3-cyanobenzamide, 4-cyanobenzamide or a mixture thereof” as instantly claimed.
“The discovery of a previously unappreciated property of a prior art composition,” such as quantifying the exact proportion of materials in the high-boiling point impurities, “or of a scientific explanation for the prior art’s functioning, does not render the old composition patentably new to the discoverer” and “the claiming of a new use, new function or unknown property which is inherently present in the prior art does not necessarily make the claim patentable”, see MPEP 2112 I.
Claims 1-18, 20, and 21 are newly rejected under 35 U.S.C. 103 as being unpatentable over Otsuka et al. (US20020035287, published 21 March 2002, hereinafter Otsuka ‘287) in view of Sheely (US3895050, published 15 July 1975) and in further view of Ibi et al. (US20170217873, published 03 August 2017, hereinafter Ibi), as applied to claims 1-7, 11-18, and 21 in the 35 USC 103 rejection above, in further view of Prochazka et al. (US20110275869, published 10 November 2011, hereinafter Prochazka).
Otsuka ‘287 is in the known prior art field of distillation for the purification of desired hydrocarbons from a produced hydrocarbon stream, see Abstract; Fig. 1; Paras. [0009]-[0014];[0029]-[0032], where column C “high-boiling-point impurities are separated from isophthalonitrile and removed from the bottom potion of the column”, see Para. [0026]; Fig. 1.
Otsuka ‘287 does not teach the limitations of instant application claims 8-10 and 20.
Prochazka in the known prior art field of distillation for the purification of desired hydrocarbons from a produced hydrocarbon stream and combustion of produced hydrocarbons and by-products, see Abstract; Paras. [0052];[0218]-[0231].
Regarding instant application claims 8-10 and 20, Prochazka teaches the remaining residue, such as organic components low in aromatics, inorganic process chemicals, etc., from a distillation column “can be passed to a further work-up and/or thermal utilization, preferably within the process of the invention or an integrated pulp process coupled therewith”, see Paras. [0118]-[0119], where the further work-up and/or thermal utilization is “combustion to obtain heat, which is preferably used further in the process of the invention or an integrated process”, see Para. [0133], the heat is used to generate steam, see Paras. [0207];[0229], “[t]ransport is preferably effected via a pipe”, see Para. [0108], and the steam generated from combustion of residue, see Paras. [0118]-[0119];[0133];[0207];[0229], is used throughout the entire process, see Paras. [0065]-[0066];[0118];[0143], meeting:
The steam generation by combustion in instant application claim 8 and instant application claim 20; and,
The pipe transport in instant application claim 9; and,
The steam as a heat source in instant application claim 10
Regarding instant application claim 20, Prochazka teaches “[t]ransport is preferably effected via a pipe”, see Para. [0108], where ; Para. [0119].
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified the process of Otsuka ‘287 by relying upon the steam generation by combustion of distillation residue of Prochazka with a reasonable predictability of success for the purpose of efficiently producing at least one organic liquid or liquefiable material of value with minimal environmental impact by pursuing the known options within their technical grasp, such as combustion of by-products and energy recovery from the combustion to create heat and steam, see Prochazka, Abstract; Paras. [0133];[0207];[0229].
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Otsuka ‘287 and Prochazka both teach distillation for the purification of desired hydrocarbons from a produced hydrocarbon stream in the distillation industry, a person of ordinary skill in the art has good reason to modify the bottom liquid of Otsuka ‘287 by relying upon the residue combustion to produce steam that is used throughout the distillation process before the effective filing date of the claimed invention for knowledge generally available within the energy recovery distillation art, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing at least one organic liquid or liquefiable material of value with minimal environmental impact by pursuing the known options within their technical grasp, such as combustion of by-products and energy recovery from the combustion to create heat and steam, see Prochazka, Abstract; Paras. [0133];[0207];[0229]; and, MPEP 2141.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied, 426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design incentives and other market forces can prompt variations of it, either in the same field or a different one. If a person of ordinary skill can implement a predictable variation, § 103 likely bars its patentability. For the same reason, if a technique has been used to improve one device, and a person of ordinary skill in the art would recognize that it would improve similar devices in the same way, using the technique is obvious unless its actual application is beyond his or her skill”, see MPEP 2141.
“The discovery of a previously unappreciated property of a prior art composition,” such as quantifying the exact proportion of materials in the high-boiling point impurities, “or of a scientific explanation for the prior art’s functioning, does not render the old composition patentably new to the discoverer” and “the claiming of a new use, new function or unknown property which is inherently present in the prior art does not necessarily make the claim patentable”, see MPEP 2112 I.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-18 and 20 stand rejected and claim 21 is newly rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-5 of U.S. Patent No. 6509490 to Otsuka et al. (hereinafter Otsuka ‘490) in view of Otsuka et al. (JP2002097177, cited by applicant 23 August 2022, hereinafter Otsuka ‘177), Sheely (US3895050, cited by applicant 23 August 2022), Ibi et al. (US20170217873, hereinafter Ibi), Prochazka et al. (US20110275869, hereinafter Prochazka), and Poindexter (US5045156, cited by applicants 11 September 2013).
Regarding claims 1, 7, and 21, the claims of Otsuka ‘490 recite a method for producing a purified phthalonitrile (Claim 1), the method comprising:
reacting ammonia, oxygen, and xylene in the presence of a catalyst to obtain a reaction product gas comprising a phthalonitrile (Claim 1);
contacting the reaction product gas with an organic solvent that has a boiling point lower than that of the phthalonitrile to obtain a collection liquid (Claims 1 and 3-5);
distilling the collection liquid by a high boiling point fraction-separating column having a column top and a column bottom, thereby obtaining a gas comprising the phthalonitrile and the organic solvent from the column top, and obtaining a bottom liquid (Claims 1 and 2); and removing the organic solvent from the gas obtained from the column top to obtain a purified phthalonitrile (Claims 1, 2, and 5).
The claims of Otsuka ‘490 lack and a cyanobenzamide; obtaining a bottom liquid that comprises a cyanobenzamide from the column bottom [deleted];
combusting the bottom liquid, while maintaining the bottom liquid in a liquid state.
However, as per MPEP 804 II.B.1., the portion of the specification that describes subject matter that falls within the scope of the claim may be relied upon to properly construe the scope of the claim. As such, Otsuka ‘490, Example 1 is within the scope of Otsuka ‘490 claims and teaches on Col. 7:
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which would anticipate instant claims 1, 7 and 21 with cyanobenzamide in the gas; a distillation pressure of 8 kPa, obtaining a bottom liquid that comprises a cyanobenzamide from the column bottom, the bottom liquid having a phthalonitrile content of 90% by mass or less but for, combusting the bottom liquid, while maintaining the bottom liquid in a liquid state limitation in the claim. As detailed above in the 35 USC 103 rejection of claim 1, the limitation is rendered obvious over Otsuka et al. (US20020035287, cited by applicant 23 August 2022, hereinafter Otsuka ‘287, which is the English equivalent of Otsuka ‘177) in view of Sheely (US3895050, cited by applicant 23 August 2022).
[deleted]
Regarding claims 1, 2, 7, and 21, the claims of Otsuka ‘490 do not recite the distilling comprises;
[deleted]
adjusting the temperature of the column bottom to 200 to 230°C.
However, as per MPEP 804 II.B.1., the portion of the specification that describes subject matter that falls within the scope of the claim may be relied upon to properly construe the scope of the claim. As such, Otsuka ‘490, Example 1 is within the scope of Otsuka ‘490 claims and teaches on Col. 7: see above, which would anticipate instant claims 1, 2, 7, and 21 with adjusting the distillation pressure to 12 kPa or less; and adjusting the temperature of the column bottom to 200 to 230°C; but for, adjusting the liquid residence time at the column bottom to 72 hours or less limitation in the claim. As detailed above in the 35 USC 103 rejection of claims 1, 2, 7, and 21, the limitation are rendered obvious over Otsuka et al. (US20020035287, cited by applicant 23 August 2022, hereinafter Otsuka ‘287, which is the English equivalent of Otsuka ‘177) in view of Sheely (US3895050, cited by applicant 23 August 2022) and Ibi et al. (US20170217873, hereinafter Ibi).
Regarding claims 3 and 12, the claims of Otsuka ‘490 do not recite wherein: the reacting, the contacting, the distilling, the combusting, and the removing are carried out continuously;
the reaction product gas further comprises a tolunitrile; and
the tolunitrile is recovered from the reaction product gas and used as the organic solvent in the contacting.
Otsuka ‘177 teaches wherein: the reacting, the contacting, the distilling, and the removing are carried out continuously (Para. [0019], Example 1, “An ammoxidation reactor A was filled with 6 L of the fluidized catalyst prepared above, and air, meta-xylene (MX) and ammonia were mixed … The reaction product gas from the top of the reactor was introduced into an isophthalonitrile absorption column B, where the isophthalonitrile in the reaction product gas was absorbed in a m-tolunitrile solvent. … The composition of the collected liquid at the end of collection was 73.5 wt % m-tolunitrile, 25 wt % isophthalonitrile, 1 wt % cyanobenzamide, and 0.5 wt % other components. The collected liquid was supplied to the middle stage of the higher bp separation column C, and the distillate gas from the higher bp separation column C was supplied to the middle stage of the rectification column D.”; Claim 1, “b) a high-boiling separation step in which the isophthalonitrile collected liquid from the collection step is distilled to recover isophthalonitrile and the organic solvent from a column top, and impurities having a boiling point higher than that of isophthalonitrile are separated into a column bottom”; Figure 1 depicts a continuous operation; Para. [0021], “However, continuous operation became difficult due to line blockage caused by severe scattering of isophthalonitrile from the condensation system to the vacuum exhaust system.”, i.e., Comparative Example 2 disturbed continuous operation; therefore, the process of Otsuka ‘177 Example 1 is continuous); and
the tolunitrile is recovered from the reaction product gas and the organic solvent in the contacting (Para. [0019], “the ammoxidation reaction product gas was absorbed for 2 hours. The composition of the collected liquid at the end of collection was 73.5 wt % m-tolunitrile, 25 wt % isophthalonitrile, 1 wt % cyanobenzamide, and 0.5 wt % other components.”; Para. [0005], “recovering the organic solvent from the top of the column”).
Sheely teaches continuous combusting (Figs. 1 and 2 depict a continuous process; Col. 10, Ln. 53-Col. 11, Ln. 8, “water is continually recovered and recycled and since hydrocarbon solvent is available for quenching purposes, polymer by-products and entrained catalyst particles are removed almost entirely from the reactor effluent in the quench column, and fuel values in the off-gases passed to the incinerator can be controlled to within close limits … and recovery of bottoms that may be disposed of by incineration rather than by biological treatment. Since incineration may be conducted so as to obtain complete combustion. the incinerator output can be controlled so as to meet governmental standards as to carbon monoxide content. Furthermore, the rate of solvent loss can be limited to what is required to satisfy incinerator fuel requirements.”), the reaction product gas further comprises a tolunitrile (Col. 11, Lns. 9-68, “nitriles are formed by ammoxidation of other olefins. e.g.. … tolunitrile, phthalonitrile, iso- and terephthalonitrile from the xylene isomers”) and the recovered solvent is used as the organic solvent (Col. 3, Lns. 45-48, “Solvent recovered in the products column is recycled to the absorber and lights column.”; Col. 4, Lns. 52-57, “Although not shown, it is to be understood that the quench column bottoms may be treated to recover the catalyst fines and hydrocarbon solvent for reuse in the system.”).
Regarding claim 4, the claims of Otsuka ‘490 recite wherein the tolunitrile is meta-tolunitrile, para-tolunitrile, or a mixture thereof (Claim 4, “m-tolunitrile”).
Regarding claims 5 and 13-15, the claims of Otsuka ‘490 do not recite wherein the cyanobenzamide is 3-cyanobenzamide, 4-cyanobenzamide or a mixture thereof.
Ibi teaches wherein the cyanobenzamide is 3-cyanobenzamide (Para. [0078], “The composition of the organic phase obtained from the bottom of the column included 97.39% by mass of isophthalonitrile, 0.10% by mass of meta-tolunitrile, 1.821% by mass of 3-cyanobenzamide, and 0.043% by mass of 3-cyanobenzoic acid.”).
Regarding claims 6 and 16-18, the claims of Otsuka ‘490 recite wherein the phthalonitrile is isophthalonitrile, terephthalonitrile, or a mixture thereof (Claims 1-5, “isophthalonitrile”).
Regarding claim 7, the claims of Otsuka ‘490 recite a method for purifying a phthalonitrile (Claim 1), the method comprising:
contacting a reaction product gas that comprises a phthalonitrile with an organic solvent that has a boiling point lower than that of the phthalonitrile to obtain a collection liquid (Claims 1 and 3-5);
distilling the collection liquid by a high boiling point fraction-separating column having a column top and a column bottom, thereby obtaining a gas comprising the phthalonitrile and the organic solvent from the column top (Claims 1 and 2), and obtaining a bottom liquid (Claim 1); and removing the organic solvent from the gas obtained from the column top to obtain a purified phthalonitrile (Claims 1, 2, and 5).
The claims of Otsuka ‘490 do not recite a cyanobenzamide; obtaining a bottom liquid that comprises a cyanobenzamide from the column bottom [deleted]; and,
combusting the bottom liquid while maintaining the bottom liquid in a liquid state.
However, as per MPEP 804 II.B.1., the portion of the specification that describes subject matter that falls within the scope of the claim may be relied upon to properly construe the scope of the claim. As such, Otsuka ‘490, Example 1 is within the scope of Otsuka ‘490 claims and teaches on Col. 7: see above, which would anticipate instant claim 7 with cyanobenzamide in the gas; and, obtaining a bottom liquid that comprises a cyanobenzamide from the column bottom [deleted]; but for, combusting the bottom liquid, while maintaining the bottom liquid in a liquid state limitation in the claim. As detailed above in the 35 USC 103 rejection of claim 7, the limitation is rendered obvious over Otsuka et al. (US20020035287, cited by applicant 23 August 2022, hereinafter Otsuka ‘287, which is the English equivalent of Otsuka ‘177) in view of Sheely (US3895050, cited by applicant 23 August 2022).
[deleted]
Regarding claims 8 and 20, the claims of Otsuka ‘490 do not recite wherein combusting further comprises generating steam with the heat generated by combustion.
Prochazka in the field of distillation and combustion of hydrocarbons (Para. [0052], “The removal of components which can be vaporized without decomposition from the lignin-comprising fraction can be carried out by customary distillation processes known to those skilled in the art.”) teaches wherein combusting further comprises generating steam with the heat generated by combustion (Para. [0118]-[0119], “The separation by distillation of the product obtained from the decomposition in the liquid state in step b) can be carried out by conventional methods known to those skilled in the art. … The separation of the product obtained from the decomposition in the liquid state in step b) is preferably also effected by extraction. Here, at least part of the aromatics obtained in the decomposition in step b) is separated off, while the remaining residue (organic components low in aromatics, inorganic process chemicals, etc.) can be passed to a further work-up and/or thermal utilization, preferably within the process of the invention or an integrated pulp process coupled therewith.”; Para. [0133], “Components other than inert materials which have been separated off are passed to another use, for example, combustion to obtain heat, which is preferably used further in the process of the invention or an integrated process.”; Para. [0207], “Particular preference is given to feeding the stream E3) into the waste liquor combustion (recovery boiler). This embodiment has the advantage that no additional apparatuses for steam or power generation or flue gas desulfurization for combustion of the stream E3) are required.”).
Regarding claim 9, the claims of Otsuka ‘490 do not recite wherein the combusting further comprises transferring the bottom liquid with a piping, and wherein the piping is heated with the steam.
Otsuka ‘177 teaches transferring the bottom liquid (Para. [0013], “In the high boiling separation step, the isophthalonitrile absorbed in the organic solvent is distilled in a high boiling separation column, impurities having a boiling point higher than that of isophthalonitrile are separated from the bottom of the column, and isophthalonitrile and the organic solvent are recovered from the top of the column. ”; Figure 1, column C bottom portion removal).
Ibi teaches wherein the piping is heated with the steam (Para. [0074], “a double pipe structure capable of steam heating”).
Prochazka teaches wherein the combusting further comprises transferring the bottom liquid with a piping, and wherein the piping is heated with the steam (Para. [0108], “If a cellulose-depleted fraction from the pulp process is used for the decomposition in step b), then the decomposition is advantageously carried out in close proximity to the site of pulp production in order to keep the outlay for transport of the cellulose-depleted fraction, especially a black liquor, low. Transport is preferably effected via a pipe.”; Para. [0119], “while the remaining residue (organic components low in aromatics, inorganic process chemicals, etc.) can be passed to a further work-up and/or thermal utilization, preferably within the process of the invention”; Para. [0207], “Particular preference is given to feeding the stream E3) into the waste liquor combustion (recovery boiler). This embodiment has the advantage that no additional apparatuses for steam or power generation or flue gas desulfurization for combustion of the stream E3) are required.”; Para. [0133], “Components other than inert materials which have been separated off are passed to another use, for example, combustion to obtain heat, which is preferably used further in the process of the invention”, i.e., further use in the process such as to heat piping).
Regarding claim 10, the claims of Otsuka ‘490 do not recite wherein the steam is used as a heat source in the contacting, the distilling, or the removing.
Prochazka teaches wherein the steam is used as a heat source in the contacting, the distilling, or the removing (Para. [0118], “Preference is given to a steam distillation, giving a distillate enriched in aromatics. In this procedure, the steam volatility of the aromatic fragments obtained in the decomposition in step b) is utilized to separate these off from the decomposition product.”; Para. [0133], “Components other than inert materials which have been separated off are passed to another use, for example, combustion to obtain heat, which is preferably used further in the process of the invention or an integrated process.”; Para. [0207], “Particular preference is given to feeding the stream E3) into the waste liquor combustion (recovery boiler). This embodiment has the advantage that no additional apparatuses for steam or power generation or flue gas desulfurization for combustion of the stream E3) are required.”, i.e., combusted materials obtained from the process are used for steam distillation and removing).
Regarding claim 11, the claims of Otsuka ‘490 recite a method for producing a phthalonitrile by an ammoxidation reaction (Claim 1).
The claims of Otsuka ‘490 do not recite the method comprising:
subjecting a treated liquid to combustion while maintaining the treated liquid in a liquid state, wherein the treated liquid comprises 90% by mass or less of a phthalonitrile, a cyanobenzamide, and an organic solvent.
However, as per MPEP 804 II.B.1., the portion of the specification that describes subject matter that falls within the scope of the claim may be relied upon to properly construe the scope of the claim. As such, Otsuka ‘490, Example 1 is within the scope of Otsuka ‘490 claims and teaches on Col. 7: see above [deleted]; but for, subjecting a treated liquid to combustion while maintaining the treated liquid in a liquid state. As detailed above in the 35 USC 103 rejection of claim 11, the limitation is rendered obvious over Otsuka et al. (US20020035287, cited by applicant 23 August 2022, hereinafter Otsuka ‘287, which is the English equivalent of Otsuka ‘177) in view of Poindexter (US5045156, cited by applicants 11 September 2013).
[deleted]
Regarding instant application claims 1, 7, 11, and 21, Otsuka ‘287 teaches the distillation bottom liquid from “high-boiling-point impurity separation column C” contains 2% “unrecovered isophthalonitrile”, 2% to 6% “unrecovered isophthalonitrile”, and “a large amount of” “unrecovered isophthalonitrile”, see Paras. [0049]-[0052]; Fig. 1. Since “a prima facie case of obviousness exists” where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” and where the claimed ranges or amounts do not overlap with the prior art but are merely close, see MPEP 2144.05, one of ordinary skill in the art, before the effective filing date of the claimed invention, would be able to predictably determine the desired “distribution of isophthalonitrile concentration” in the distillation column bottom liquid from the high-boiling-point impurity separation column C of Otsuka ‘287, such as more than 5% by mass to less than 90% by mass, for the purpose of preventing plugging in the line/pipe of condensed isophthalonitrile disturbing continuous operation, see Paras. [0008]-[0009];[0032];[0051]-[0052]; Fig. 1, meeting within the liquid phthalonitriles bottom effluent concentration in instant application claim 1, in instant application claim 7, and in instant application claim 21.
Regarding instant application claims 1, 7, and 21, Ibi teaches in order to prevent the formation of phthalonitrile isomers “a shorter residence time of” phthalonitrile in the bottom of the column is preferred, such as “180 minutes or less, more preferably 10 to 120 minutes, furthermore preferably 15 to 60 minutes, particularly preferably 20 to 30 minutes”, see Para. [0047], meeting within the residence time range in instant application claim 1, in instant application claim 7, and in instant application claim 21.
Regarding instant application claim 2, Otsuka ‘287 teaches distillation in column C is “performed at a top pressure of 8 kPa, a top temperature of 164° C., and a bottom temperature of 204° C.”, see Para. [0050], meeting within the temperature range in instant application claim 2.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified
the claims of Otsuka ‘490 with the combustion and process material recovery teachings of Sheely, the residence time and specific cyanobenzamide teachings of Ibi, the combustion, steam generation, and energy recovery teachings of Prochazka, and the combustion teachings of Poindexter with a reasonable predictability of success. By applying “routine optimization” and “predictable results” to select the optimal disposal, combustion, energy recover, and recovery of process materials, as taught by Sheely, Ibi, Prochazka, and Poindexter, one of ordinary skill in the art would have been motivated to make these modifications because Sheely, Ibi, Prochazka, and Poindexter provide a finite number of identified, predictable solutions, and a person of ordinary skill in the art has good reason to efficiently produce a nitrile compound with minimal environmental impact by pursuing the known options within their technical grasp, such as the recovery of process materials, the combustion of by-products, and energy recovery, for the benefit of producing a nitrile compound with efficiency and minimal environmental impact (Otsuka ‘287, Para. [0029], “in order to obtain isophthalonitrile at high yield, separation of high-boiling-point impurities must be performed as rapidly as possible and at as low a temperature as possible”; Sheely, Col. 2, Ln. 65-Col. 3, Ln. 14, “It is recognized that incineration is the only practical way of effectively disposing of many industrial waste materials that are toxic, hazardous or expensive to store, or of a nature as to require extensive degradation treatment before being discharged into natural bodies of water. … an improved method of recovering by-product waste materials whereby said materials may be ultimately disposed of by incineration.”; Ibi, Para. [0047], “in order to suppress the formation of the group of multimers of dicyanobenzene in the liquid phase (at the bottom of the column, in the case of a distillation column), a shorter residence time of dicyanobenzene in a melt state is preferred”; Para. [0078], “a residence time at the bottom of the column of 20 minutes. … while an organic phase mainly containing isophthalonitrile in a melt state was extracted from the bottom of the column. The composition of the organic phase obtained from the bottom of the column included 97.39% by mass of isophthalonitrile, 0.10% by mass of meta-tolunitrile, 1.821% by mass of 3-cyanobenzamide, and 0.043% by mass of 3-cyanobenzoic acid.”; Prochazka, Para. [0133], “Components other than inert materials which have been separated off are passed to another use, for example, combustion to obtain heat, which is preferably used further in the process of the invention or an integrated process.”; Para. [0207], “Particular preference is given to feeding the stream E3) into the waste liquor combustion (recovery boiler). This embodiment has the advantage that no additional apparatuses for steam or power generation or flue gas desulfurization for combustion of the stream E3) are required.”; Poindexter, Col. 1, Lns. 35-44, “a product which substituted in whole or in part for IPN during the distillation which would increase the recovery of IPN from the bottoms and keep the bottoms fluid and pumpable for disposal by incineration … Furthermore, the product would reduce maintenance costs by eliminating shutdowns due to foulant accumulation and increase production by increasing operating utility.”). See MPEP 2141.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied, 426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design incentives and other market forces can prompt variations of it, either in the same field or a different one. If a person of ordinary skill can implement a predictable variation, § 103 likely bars its patentability. For the same reason, if a technique has been used to improve one device, and a person of ordinary skill in the art would recognize that it would improve similar devices in the same way, using the technique is obvious unless its actual application is beyond his or her skill”. See MPEP 2141.
Further, In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929) states “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions, or degree, or the
substitution of equivalents doing the same thing as the original invention, by
substantially the same means,” such as quantifying the exact proportion of materials in the high-boiling point impurities, “is not such an invention as will sustain a patent, even
though the changes of the kind may produce better results than prior inventions”.
In addition, selection of a known material, such as the specific cyanobenzamide by-product and steam heated piping, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945). See MPEP 2144.07.
Claims 1-18 and 20 stand rejected and claim 21 is newly rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 2 of U.S. Patent No. 6646163 to Nakamura et al. (hereinafter Nakamura) in view of Otsuka et al. (US20020035287, cited by applicant 23 August 2022, hereinafter Otsuka ‘287), Sheely (US3895050, cited by applicant 23 August 2022), Ibi et al. (US20170217873, hereinafter Ibi), Prochazka et al. (US20110275869, hereinafter Prochazka), and Poindexter (US5045156, cited by applicants 11 September 2013).
Regarding claims 1, 7, and 21, the claims of Nakamura recite a method for producing a purified phthalonitrile (Claim 1), the method comprising:
reacting ammonia, oxygen, and xylene in the presence of a catalyst to obtain a reaction product gas comprising a phthalonitrile (Claim 1);
contacting the reaction product gas with an organic solvent (Claims 1 and 2);
distilling the collection liquid by a high boiling point fraction-separating column having a column top and a column bottom, thereby obtaining a gas comprising the phthalonitrile and the organic solvent from the column top, and obtaining a bottom liquid (Claims 1 and 2); and removing the organic solvent from the gas obtained from the column top to obtain a purified phthalonitrile (Claims 1 and 2).
The claims of Nakamura lack and a cyanobenzamide, an organic solvent that has a boiling point lower than that of the phthalonitrile to obtain a collection liquid; obtaining a bottom liquid that comprises a cyanobenzamide from the column bottom, the bottom liquid having a phthalonitrile content of 90% by mass or less;
combusting the bottom liquid, while maintaining the bottom liquid in a liquid state.
However, as per MPEP 804 II.B.1., the portion of the specification that describes subject matter that falls within the scope of the claim may be relied upon to properly construe the scope of the claim. As such, Nakamura, Example 1 is within the scope of Nakamura claims and teaches on Cols. 8-9:
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which would anticipate instant claim 1 with cyanobenzamide in the gas; a distillation pressure of 8 kPa; an organic solvent that has a boiling point lower than that of the phthalonitrile to obtain a collection liquid and, obtaining a bottom liquid that comprises a cyanobenzamide from the column bottom, the bottom liquid having a phthalonitrile content of 90% by mass or less; but for, combusting the bottom liquid, while maintaining the bottom liquid in a liquid state limitation in the claim. As detailed above in the 35 USC 103 rejection of claim 1, the limitation is rendered obvious over Otsuka et al. (US20020035287, cited by applicant 23 August 2022, hereinafter Otsuka ‘287) in view of Sheely (US3895050, cited by applicant 23 August 2022).
[deleted]
Regarding claims 1, 2, 7, and 21, the claims of Nakamura do not recite the distilling comprises;
[deleted]
adjusting the temperature of the column bottom to 200 to 230°C.
However, as per MPEP 804 II.B.1., the portion of the specification that describes subject matter that falls within the scope of the claim may be relied upon to properly construe the scope of the claim. As such, Nakamura, Example 1 is within the scope of Nakamura claims and teaches on Cols. 8-9: see above, which would anticipate instant claims 1, 2, 7, and 21 with adjusting the distillation pressure to 12 kPa or less; and adjusting the temperature of the column bottom to 200 to 230°C; but for, adjusting the liquid residence time at the column bottom to 72 hours or less limitation in the claim. As detailed above in the 35 USC 103 rejection of claims 1, 2, 7, and 21, the limitations are rendered obvious over Otsuka et al. (US20020035287, cited by applicant 23 August 2022, hereinafter Otsuka ‘287) in view of Sheely (US3895050, cited by applicant 23 August 2022) and Ibi et al. (US20170217873, hereinafter Ibi).
Regarding claims 3 and 12, the claims of Nakamura do not recite wherein: the reacting, the contacting, the distilling, the combusting, and the removing are carried out continuously;
the reaction product gas further comprises a tolunitrile; and
the tolunitrile is recovered from the reaction product gas and used as the organic solvent in the contacting.
Otsuka ‘287 teaches wherein: the reacting, the contacting, the distilling, and the removing are carried out continuously (Paras. [0045]-[0050], Example 1; Figure 1 depicts a continuous operation; Para. [0051], “disturbing continuous operation”, i.e., Comparative Example 1 disturbed continuous operation; therefore, the process of Otsuka ‘287 Example 1 is continuous); and
the tolunitrile is recovered from the reaction product gas and the organic solvent in the contacting (Para. [0049], “the gas produced through the aforementioned ammoxidation was subjected to a trapping process for two hours by use of m-tolunitrile (2 kg) charged into the trapping column … After completion of trapping, the liquid was found to have the following composition; i.e., m-tolunitrile (73.5 wt. %), isophthalonitrile (25 wt. %), cyanobenzamide (1 wt. %), and other components (0.5 wt. %)”; Figure 1, solvent is recovered).
Sheely teaches continuous combusting (Figs. 1 and 2 depict a continuous process; Col. 10, Ln. 53-Col. 11, Ln. 8, “water is continually recovered and recycled and since hydrocarbon solvent is available for quenching purposes, polymer by-products and entrained catalyst particles are removed almost entirely from the reactor effluent in the quench column, and fuel values in the off-gases passed to the incinerator can be controlled to within close limits … and recovery of bottoms that may be disposed of by incineration rather than by biological treatment. Since incineration may be conducted so as to obtain complete combustion. the incinerator output can be controlled so as to meet governmental standards as to carbon monoxide content. Furthermore, the rate of solvent loss can be limited to what is required to satisfy incinerator fuel requirements.”), the reaction product gas further comprises a tolunitrile (Col. 11, Lns. 9-68, “nitriles are formed by ammoxidation of other olefins. e.g.. … tolunitrile, phthalonitrile, iso- and terephthalonitrile from the xylene isomers”) and the recovered solvent is used as the organic solvent (Col. 3, Lns. 45-48, “Solvent recovered in the products column is recycled to the absorber and lights column.”; Col. 4, Lns. 52-57, “Although not shown, it is to be understood that the quench column bottoms may be treated to recover the catalyst fines and hydrocarbon solvent for reuse in the system.”).
Regarding claim 4, the claims of Nakamura do not recite wherein the tolunitrile is meta-tolunitrile, para-tolunitrile, or a mixture thereof.
However, as per MPEP 804 II.B.1., the portion of the specification that describes subject matter that falls within the scope of the claim may be relied upon to properly construe the scope of the claim. As such, Nakamura, Example 1 is within the scope of Nakamura claims and teaches on Cols. 8-9: see above, which would anticipate instant claim 4 with meta-tolunitrile. As detailed above in the 35 USC 103 rejection of claim 4, the limitation is rendered obvious over Otsuka et al. (US20020035287, cited by applicant 23 August 2022, hereinafter Otsuka ‘287) in view of Sheely (US3895050, cited by applicant 23 August 2022).
Regarding claims 5 and 13-15, the claims of Nakamura do not recite wherein the cyanobenzamide is 3-cyanobenzamide, 4-cyanobenzamide or a mixture thereof.
However, as per MPEP 804 II.B.1., the portion of the specification that describes subject matter that falls within the scope of the claim may be relied upon to properly construe the scope of the claim. As such, Nakamura, Example 1 is within the scope of Nakamura claims and teaches on Cols. 8-9: see above, which would anticipate instant claims 5 and 13-15 with 3-cyanobenzamide. As detailed above in the 35 USC 103 rejection of claims 5 and 13-15, the limitation is rendered obvious over Otsuka et al. (US20020035287, cited by applicant 23 August 2022, hereinafter Otsuka ‘287) in view of Sheely (US3895050, cited by applicant 23 August 2022) and Ibi et al. (US20170217873, hereinafter Ibi).
Regarding claims 6 and 16-18, the claims of Nakamura do not recite wherein the phthalonitrile is isophthalonitrile, terephthalonitrile, or a mixture thereof.
However, as per MPEP 804 II.B.1., the portion of the specification that describes subject matter that falls within the scope of the claim may be relied upon to properly construe the scope of the claim. As such, Nakamura, Example 1 is within the scope of Nakamura claims and teaches on Cols. 8-9: see above, which would anticipate instant claims 6 and 16-18 with isophthalonitrile. As detailed above in the 35 USC 103 rejection of claims 6 and 16-18, the limitation is rendered obvious over Otsuka et al. (US20020035287, cited by applicant 23 August 2022, hereinafter Otsuka ‘287) in view of Sheely (US3895050, cited by applicant 23 August 2022).
Regarding claim 7, the claims of Nakamura recite a method for purifying a phthalonitrile (Claim 1), the method comprising:
contacting a reaction product gas that comprises a phthalonitrile with an organic solvent to obtain a collection liquid (Claims 1 and 2);
distilling the collection liquid by a high boiling point fraction-separating column having a column top and a column bottom, thereby obtaining a gas comprising the phthalonitrile and the organic solvent from the column top (Claims 1 and 2), and obtaining a bottom liquid (Claim 1); and removing the organic solvent from the gas obtained from the column top to obtain a purified phthalonitrile (Claim 1).
The claims of Nakamura do not recite and a cyanobenzamide, an organic solvent that has a boiling point lower than that of the phthalonitrile; obtaining a bottom liquid that comprises a cyanobenzamide from the column bottom, the bottom liquid having a phthalonitrile content of 90% by mass or less;
combusting the bottom liquid while maintaining the bottom liquid in a liquid state.
However, as per MPEP 804 II.B.1., the portion of the specification that describes subject matter that falls within the scope of the claim may be relied upon to properly construe the scope of the claim. As such, Nakamura, Example 1 is within the scope of Nakamura claims and teaches on Cols. 8-9: see above, which would anticipate instant claim 7 with cyanobenzamide in the gas; an organic solvent that has a boiling point lower than that of the phthalonitrile and, obtaining a bottom liquid that comprises a cyanobenzamide from the column bottom, the bottom liquid having a phthalonitrile content of 90% by mass or less; but for, combusting the bottom liquid, while maintaining the bottom liquid in a liquid state limitation in the claim. As detailed above in the 35 USC 103 rejection of claim 7, the limitation is rendered obvious over Otsuka et al. (US20020035287, cited by applicant 23 August 2022, hereinafter Otsuka ‘287) in view of Sheely (US3895050, cited by applicant 23 August 2022).
[deleted]
Regarding claims 8 and 20, the claims of Nakamura do not recite wherein combusting further comprises generating steam with the heat generated by combustion.
Prochazka in the field of distillation and combustion of hydrocarbons (Para. [0052], “The removal of components which can be vaporized without decomposition from the lignin-comprising fraction can be carried out by customary distillation processes known to those skilled in the art.”) teaches wherein combusting further comprises generating steam with the heat generated by combustion (Para. [0118]-[0119], “The separation by distillation of the product obtained from the decomposition in the liquid state in step b) can be carried out by conventional methods known to those skilled in the art. … The separation of the product obtained from the decomposition in the liquid state in step b) is preferably also effected by extraction. Here, at least part of the aromatics obtained in the decomposition in step b) is separated off, while the remaining residue (organic components low in aromatics, inorganic process chemicals, etc.) can be passed to a further work-up and/or thermal utilization, preferably within the process of the invention or an integrated pulp process coupled therewith.”; Para. [0133], “Components other than inert materials which have been separated off are passed to another use, for example, combustion to obtain heat, which is preferably used further in the process of the invention or an integrated process.”; Para. [0207], “Particular preference is given to feeding the stream E3) into the waste liquor combustion (recovery boiler). This embodiment has the advantage that no additional apparatuses for steam or power generation or flue gas desulfurization for combustion of the stream E3) are required.”).
Regarding claim 9, the claims of Nakamura do not recite wherein the combusting further comprises transferring the bottom liquid with a piping, and wherein the piping is heated with the steam.
Otsuka ‘287 teaches transferring the bottom liquid (Para. [0026], “Thus, high-boiling-point impurities are separated from isophthalonitrile and removed from the bottom potion of the column”; Figure 1, column C bottom portion removal).
Ibi teaches wherein the piping is heated with the steam (Para. [0074], “a double pipe structure capable of steam heating”).
Prochazka teaches wherein the combusting further comprises transferring the bottom liquid with a piping, and wherein the piping is heated with the steam (Para. [0108], “If a cellulose-depleted fraction from the pulp process is used for the decomposition in step b), then the decomposition is advantageously carried out in close proximity to the site of pulp production in order to keep the outlay for transport of the cellulose-depleted fraction, especially a black liquor, low. Transport is preferably effected via a pipe.”; Para. [0119], “while the remaining residue (organic components low in aromatics, inorganic process chemicals, etc.) can be passed to a further work-up and/or thermal utilization, preferably within the process of the invention”; Para. [0207], “Particular preference is given to feeding the stream E3) into the waste liquor combustion (recovery boiler). This embodiment has the advantage that no additional apparatuses for steam or power generation or flue gas desulfurization for combustion of the stream E3) are required.”; Para. [0133], “Components other than inert materials which have been separated off are passed to another use, for example, combustion to obtain heat, which is preferably used further in the process of the invention”, i.e., further use in the process such as to heat piping).
Regarding claim 10, the claims of Nakamura do not recite wherein the steam is used as a heat source in the contacting, the distilling, or the removing.
Prochazka teaches wherein the steam is used as a heat source in the contacting, the distilling, or the removing (Para. [0118], “Preference is given to a steam distillation, giving a distillate enriched in aromatics. In this procedure, the steam volatility of the aromatic fragments obtained in the decomposition in step b) is utilized to separate these off from the decomposition product.”; Para. [0133], “Components other than inert materials which have been separated off are passed to another use, for example, combustion to obtain heat, which is preferably used further in the process of the invention or an integrated process.”; Para. [0207], “Particular preference is given to feeding the stream E3) into the waste liquor combustion (recovery boiler). This embodiment has the advantage that no additional apparatuses for steam or power generation or flue gas desulfurization for combustion of the stream E3) are required.”, i.e., combusted materials obtained from the process are used for steam distillation and removing).
Regarding claim 11, the claims of Nakamura recite a method for producing a phthalonitrile by an ammoxidation reaction (Claim 1).
The claims of Nakamura do not recite the method comprising:
subjecting a treated liquid to combustion while maintaining the treated liquid in a liquid state, wherein the treated liquid comprises 90% by mass or less of a phthalonitrile, a cyanobenzamide, and an organic solvent.
However, as per MPEP 804 II.B.1., the portion of the specification that describes subject matter that falls within the scope of the claim may be relied upon to properly construe the scope of the claim. As such, Nakamura, Example 1 is within the scope of Nakamura claims and teaches on Cols. 8-9: see above, which would anticipate instant claim 11 with wherein the treated liquid comprises 90% by mass or less of a phthalonitrile, a cyanobenzamide, and an organic solvent limitation in the claim; but for, subjecting a treated liquid to combustion while maintaining the treated liquid in a liquid state. As detailed above in the 35 USC 103 rejection of claim 11, the limitation is rendered obvious over Otsuka et al. (US20020035287, cited by applicant 23 August 2022, hereinafter Otsuka ‘287) in view of Poindexter (US5045156, cited by applicants 11 September 2013).
[deleted]
Regarding instant application claims 1, 7, and 21, Ibi teaches in order to prevent the formation of phthalonitrile isomers “a shorter residence time of” phthalonitrile in the bottom of the column is preferred, such as “180 minutes or less, more preferably 10 to 120 minutes, furthermore preferably 15 to 60 minutes, particularly preferably 20 to 30 minutes”, see Para. [0047], meeting within the residence time range in instant application claim 1, in instant application claim 7, and in instant application claim 21.
Regarding instant application claim 2, Otsuka ‘287 teaches distillation in column C is “performed at a top pressure of 8 kPa, a top temperature of 164° C., and a bottom temperature of 204° C.”, see Para. [0050], meeting within the temperature range in instant application claim 2.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified
the claims of Nakamura with the combustion and process material recovery teachings of Sheely, the residence time and specific cyanobenzamide teachings of Ibi, the combustion, steam generation, and energy recovery teachings of Prochazka, and the combustion teachings of Poindexter with a reasonable predictability of success. By applying “routine optimization” and “predictable results” to select the optimal disposal, combustion, energy recover, and recovery of process materials, as taught by Sheely, Ibi, Prochazka, and Poindexter, one of ordinary skill in the art would have been motivated to make these modifications because Sheely, Ibi, Prochazka, and Poindexter provide a finite number of identified, predictable solutions, and a person of ordinary skill in the art has good reason to efficiently produce a nitrile compound with minimal environmental impact by pursuing the known options within their technical grasp, such as the recovery of process materials, the combustion of by-products, and energy recovery, for the benefit of producing a nitrile compound with efficiency and minimal environmental impact (Otsuka ‘287, Para. [0029], “in order to obtain isophthalonitrile at high yield, separation of high-boiling-point impurities must be performed as rapidly as possible and at as low a temperature as possible”; Sheely, Col. 2, Ln. 65-Col. 3, Ln. 14, “It is recognized that incineration is the only practical way of effectively disposing of many industrial waste materials that are toxic, hazardous or expensive to store, or of a nature as to require extensive degradation treatment before being discharged into natural bodies of water. … an improved method of recovering by-product waste materials whereby said materials may be ultimately disposed of by incineration.”; Ibi, Para. [0047], “in order to suppress the formation of the group of multimers of dicyanobenzene in the liquid phase (at the bottom of the column, in the case of a distillation column), a shorter residence time of dicyanobenzene in a melt state is preferred”; Para. [0078], “a residence time at the bottom of the column of 20 minutes. … while an organic phase mainly containing isophthalonitrile in a melt state was extracted from the bottom of the column. The composition of the organic phase obtained from the bottom of the column included 97.39% by mass of isophthalonitrile, 0.10% by mass of meta-tolunitrile, 1.821% by mass of 3-cyanobenzamide, and 0.043% by mass of 3-cyanobenzoic acid.”; Prochazka, Para. [0133], “Components other than inert materials which have been separated off are passed to another use, for example, combustion to obtain heat, which is preferably used further in the process of the invention or an integrated process.”; Para. [0207], “Particular preference is given to feeding the stream E3) into the waste liquor combustion (recovery boiler). This embodiment has the advantage that no additional apparatuses for steam or power generation or flue gas desulfurization for combustion of the stream E3) are required.”; Poindexter, Col. 1, Lns. 35-44, “a product which substituted in whole or in part for IPN during the distillation which would increase the recovery of IPN from the bottoms and keep the bottoms fluid and pumpable for disposal by incineration … Furthermore, the product would reduce maintenance costs by eliminating shutdowns due to foulant accumulation and increase production by increasing operating utility.”). See MPEP 2141.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied, 426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design incentives and other market forces can prompt variations of it, either in the same field or a different one. If a person of ordinary skill can implement a predictable variation, § 103 likely bars its patentability. For the same reason, if a technique has been used to improve one device, and a person of ordinary skill in the art would recognize that it would improve similar devices in the same way, using the technique is obvious unless its actual application is beyond his or her skill”. See MPEP 2141.
Further, In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929) states “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions, or degree, or the
substitution of equivalents doing the same thing as the original invention, by
substantially the same means,” such as quantifying the exact proportion of materials in the high-boiling point impurities, “is not such an invention as will sustain a patent, even
though the changes of the kind may produce better results than prior inventions”.
In addition, selection of a known material, such as the specific cyanobenzamide by-product and steam heated piping, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945). See MPEP 2144.07.
Conclusion
No claims are allowed.
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/YO/Examiner, Art Unit 1692
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699