DETAILED ACTION
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 .
Status of the Claims
Claims 1-8 and 10-13 are pending.
Claims 1, 3, and 10 are amended.
Claim 9 is currently cancelled.
Response to Amendments
Applicant’s amendments filed 06 February 2026 are acknowledged.
Claim Objections
Applicant’s amendment to claim 1 is sufficient to overcome the objection of the claim. The claim has been amended to correct the grammatical mistake. The objection is withdrawn.
Claim Rejections - 35 USC § 112
Applicant’s amendments to claims 1 and 3 are sufficient to overcome the rejection of claims 1-13 under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention. Claim 1 has been amended to correct the antecedent basis issue and claim 3 has been amended for clarity. The rejection is withdrawn.
Claim Rejections - 35 USC § 103
Applicant’s amendment to claim 1 adding specific solvents to the combined reactant stream not taught by Nair ‘679, as evidenced by Correia and Cameo, in view of Sanchez-Ramirez and Mukhopadhyay is sufficient to overcome the rejections of:
Claims 1-8, 12, and 13 under 35 U.S.C. 103 as being obvious over Nair et al. (US20200062679, hereinafter Nair ‘679), as evidenced by Correia et al. (“Fire resistance of a water filled cooled structure”, June 2006, III European Conference on Computational Mechanics Solids, Structures and Coupled Problems in Engineering, Pgs. 1-12) and Cameo Chemicals, (“Chemical Datasheet, Trifluoroacetyl Chloride”, 13 December 2016, Wayback Machine, Pgs. 1-4), in view of Sanchez-Ramirez et al. (“Reactive Distillation Column Design for Tetraethoxysilane (TEOS) Production: Economic and Environmental Aspects”, 26 March 2018, Industrial & Engineering Chemistry Research, Vol. 57, Pgs. 5024-5034, hereinafter Sanchez-Ramirez); and,
Claims 9-11 under 35 U.S.C. 103 as being obvious over Nair et al. (US20200062679, hereinafter Nair ‘679), as evidenced by Correia et al. (“Fire resistance of a water filled cooled structure”, June 2006, III European Conference on Computational Mechanics Solids, Structures and Coupled Problems in Engineering, Pgs. 1-12) and Cameo Chemicals, (“Chemical Datasheet, Trifluoroacetyl Chloride”, 13 December 2016, Wayback Machine, Pgs. 1-4), in view of Sanchez-Ramirez et al. (“Reactive Distillation Column Design for Tetraethoxysilane (TEOS) Production: Economic and Environmental Aspects”, 26 March 2018, Industrial & Engineering Chemistry Research, Vol. 57, Pgs. 5024-5034, hereinafter Sanchez-Ramirez), as applied to claims 1-8, 12, and 13 in the 35 USC 103 rejection above, in further view of Mukhopadhyay et al. (US20060122440, hereinafter Mukhopadhyay).
Due to the amendment to claim 1 and the cancellation of claim 9, the above rejections are withdrawn and a new ground(s) of rejection is/are provided below.
Response to Arguments
Applicant’s arguments filed 06 February 2026 have been fully considered but they are persuasive, moot, or not persuasive.
Applicant’s 35 U.S.C. § 102(b)(2)(C) Response
Applicant’s statements on pages 4-5 of the remarks filed on 06 February 2026 that “Yang as reference may be removed by filing a statement pursuant to 35 U.S.C. 102(b)(2)(C) establishing that, not later than the effective filing date of the claimed invention, the subject matter disclosed and the claimed invention were either owned by the same person or subject to an obligation of assignment to the same person or subject to a joint research agreement” and “Applicants submit that Yang was owned by the same person (Honeywell International Inc.) or subject to an obligation of assignment to the same person”, is sufficient to overcome the rejections of:
Claims 1-8, 12, and 13 under 35 U.S.C. 103 as being obvious over Yang et al. (WO2021207194, filed on 06 April 2021, hereinafter Yang) in view of Sanchez-Ramirez et al. (“Reactive Distillation Column Design for Tetraethoxysilane (TEOS) Production: Economic and Environmental Aspects”, 26 March 2018, Industrial & Engineering Chemistry Research, Vol. 57, Pgs. 5024-5034, hereinafter Sanchez-Ramirez) and Nair et al. (US20200062679, hereinafter Nair ‘679); and,
Claims 9-11 under 35 U.S.C. 103 as being obvious over Yang et al. (WO2021207194, filed on 06 April 2021, hereinafter Yang) in view of Sanchez-Ramirez et al. (“Reactive Distillation Column Design for Tetraethoxysilane (TEOS) Production: Economic and Environmental Aspects”, 26 March 2018, Industrial & Engineering Chemistry Research, Vol. 57, Pgs. 5024-5034, hereinafter Sanchez-Ramirez) and Nair et al. (US20200062679, hereinafter Nair ‘679 ), as applied to claims 1-8, 12, and 13 in the 35 USC 103 rejection above, in further view of Mukhopadhyay et al. (US20060122440, hereinafter Mukhopadhyay).
Due to applicant’s clear and conspicuous statement that the claimed invention of the application under examination and the subject matter disclosed in WO2021207194 to Yang et al. applied as prior art were owned by the same person or subject to an obligation of assignment to the same person, namely Honeywell International Inc., not later than the effective filing date of the claimed invention, the above rejections are withdrawn, see MPEP 2154.02(c).
Applicant’s argue that Nair ‘679, as evidenced by Correia and Cameo, in view of Sanchez-Ramirez and Mukhopadhyay do not disclose the limitations as recited in amended claim 1. These arguments have been considered but are moot or not persuasive for the reasons set forth in the new grounds of rejection below and the response to arguments below.
Applicant’s arguments throughout the remarks filed on 06 February 2026 with respect to Mukhopadhyay have been considered but are moot because the new ground of rejection does not rely on Mukhopadhyay applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
In response to applications arguments on pages 5-6 of the remarks filed on 06 February 2026 that “there is no motivation for a person of ordinary skill in the art to combine Nair's gas-phase process, which expressly criticizes liquid-phase and solvent-based processes for their inefficiency due to the need for separation and disposal steps (Nair, [0007]), with the solvent teachings … Nair teaches away from the use of solvents and liquid-phase reactions in the context of TFAI production.” See pages 6-8 and pages 25-26 of the previous office action dated 14 November 2025 (hereinafter POA) detailing a response to the above arguments and a rejection to the claim limitations of reacting in both vapor phase and liquid phase reactions, where the “teachings of Nair ‘679 would lead a person of ordinary skill in the art before the effective filing date of the claimed invention to the understanding that the Nair ‘679 process is not entirely a gas phase process as the process may run under operating conditions to include liquid water and liquid trifluoroacetyl chloride, see MPEP 2143 B & G.”
The instant specification, Para. [0007] states “[s]ome known methods of preparing trifluoroacetyl iodide include liquid-phase processes. Liquid-phase processes can require solvents that must be separated out and disposed of. The extra steps required for separation and disposal make the processes less efficient.” Nair ‘679, Para. [0007] also states “[s]ome known methods of preparing trifluoroacetyl iodide include liquid-phase processes. Liquid-phase processes can require solvents that must be separated out and disposed of. The extra steps required for separation and disposal make the processes less efficient.” The instant specification employs the use of a solvent even though it is identified as less efficient. Nair ‘679 also does not “criticize, discredit, or otherwise discourage” the use of operating conditions that renders the reactants in liquid and vapor phases, or the use of a solvent, see MPEP 2145 X.D.1., even though the use of a solvent may be less efficient. On the contrary, as stated above, the Nair ‘679 process is not entirely a gas phase process as the process may run under operating conditions to include liquid water and liquid trifluoroacetyl chloride.
In addition, “[t]he discovery of a previously unappreciated property of a prior art composition,” such as the process to make trifluoroacetyl iodide with or without a specific solvent, “or of a scientific explanation for the prior art’s functioning, does not render the old composition patentably new to the discoverer”, see MPEP 2112 I.
For the reasons indicated above and detailed in the POA, applicant’s above arguments are not persuasive.
In response to applications arguments on pages 6-8 of the remarks filed on 06 February 2026 that “Applicants' disclosure, particularly as demonstrated in Examples 3 and 4, shows that the use of toluene as a solvent in the reactive distillation system provides unexpected advantages” and the “process for producing trifluoroacetyl iodide (TFAI) from trifluoroacetyl chloride (TFAC) and hydrogen iodide (HI) in a reactive distillation reaction with or without catalyst at ambient or elevated temperatures, yields unexpected results as is evidenced by the Examples of the present application”, such as “high performance even without a catalyst”, “lower energy usage, less thermal degradation, and potentially longer equipment/catalyst lifetimes”, and “[t]he reactive distillation approach integrates reaction and purification, capturing high-purity TFAI (>99 wt.%) in one unit operation”.
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 application claim 1 states “wherein the combined reactant stream further comprises a solvent selected from the group consisting of benzene, toluene, xylenes, mesitylene (1,3,5-trimethylbenzene), ethyl benzene, dimethylformamide (DMF), dimethyl sulfoxide (DMSO), ionic liquids, and combinations thereof” and “wherein the reactive distillation column reboiler temperature is about 500C to about 1200C”.
The instant specification is relied upon for any comparison tests/examples. The instant specification, and Examples 3 and 4 do not appear to provide any test data to determine the difference in the tests of Examples 1 and 2 with or without the solvent toluene. In addition, no tests are performed with the other claimed solvents. The reboiler in the first, second, and third columns are controlled at 560C, 650C, and 740C in all Examples 1-4. There are no tests or data at the temperatures between, below, and above the controlled reboiler temperatures of 560C, 650C, and 740C. In addition, the Examples indicate the use of three distillation columns, which is not a “one unit operation”. Therefore, Applicant’s have not provided a proper comparison to the closest prior art and have not established test points inside and outside the claimed range of the differing solvents, temperatures of the reboiler, and one distillation unit operation in order to support the argument of surprising and unexpected results, see MPEP 716.02(e).
For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to applications arguments on page 7 of the remarks filed on 06 February 2026 that “Applicants' process integrates vapor phase and liquid phase reactions within a single reactive distillation column, an approach neither taught nor suggested by Nair”. “The use of patents as references is not limited to what the patentees describe as their own inventions or to the problems with which they are concerned. They are part of the literature of the art, relevant for all they contain”, see In re Heck, 699 F.2d 1331, 1332-33, 216 USPQ 1038, 1039 (Fed. Cir. 1983) (quoting In re Lemelson, 397 F.2d 1006, 1009, 158 USPQ 275, 277 (CCPA 1968)) and MPEP 2123.
As stated above, the Nair ‘679 process is not entirely a gas phase process as the process may run under operating conditions to include liquid water and liquid trifluoroacetyl chloride. Therefore, both Nair ‘679 teaches the process may be performed in the liquid and vapor phase.
For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to applications arguments on page 7 of the remarks filed on 06 February 2026 that “the cited references do not teach, suggest, or motivate the use of the specifically claimed solvents in a dual-phase, continuous reactive distillation process for TFAI production”. 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.
Nair ‘679 is in the known prior art field of a process for producing trifluoroacetyl iodide “the process comprising providing a reactant stream comprising hydrogen iodide and at least one trifluoroacetyl halide selected from the group consisting of trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof, reacting the reactant stream in the presence of a first catalyst at a first reaction temperature from about 25° C. to about 400° C”, see Abstract, where the process comprises water up to “about 500 parts per million”, see Para. [0021], and minimal steps within one reactor, i.e., the first reactor, see Paras. [0027]-[0029];[0089]; Figs. 1-3. As stated above, the Nair ‘679 process is not entirely a gas phase process as the process may run under operating conditions to include liquid water and liquid trifluoroacetyl chloride.
Sanchez-Ramirez is in the known prior art field of the problem to be solved by combining a catalytic acetalization reaction, distillation, and purification in one reactor by performing catalytic reactive distillation of a hydrocarbon and the simultaneous separation of HCl, see Abstract and Graphical Abstract; Pg. 5026, Col. 1, Last Full Para., where reactive distillation takes place in the both the liquid and vapor phases and the catalyst packed column comprises a reboiler that is used to heat the column and a condenser that is used to cool the tower to the optimal temperature, such as from about -60 °C to about 300 °C, depending upon the optimal reaction temperature for conversion, the boiling points of the products to be separated, the vapor−liquid equilibrium, and the reaction pressure, see Pg. 5026, Col. 1, Second Full Para.-Col. 2, Second Full Para.; Pg. 5028, 3.2. Reactive Distillation System – 3.3. Economical and Environmental indexes; Pgs. 5030-5033, 4.2. Reactive Distillation System, Table 4, Figs. 6-7; Pg. 5033, 5. Conclusions, and is applied to solve the efficiency problem involving multiple liquid phase reactors.
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 Nair ‘679 and Sanchez-Ramirez both teach vapor and liquid phase catalytic acetalization reactions, a person of ordinary skill in the art has good reason to modify Nair ‘679 by relying upon Sanchez-Ramirez before the effective filing date of the claimed invention for knowledge generally available within the vapor and liquid phase catalytic acetalization reaction art regarding a suitable choice of solvent, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing a reactive distillation product depending upon the optimal reaction temperature for conversion, the boiling points of the products to be separated, the vapor−liquid equilibrium, and the reaction pressure, see Sanchez-Ramirez, Pg. 5026, Col. 1, Second Full Para.-Col. 2, Second Full Para.; Pg. 5028, 3.2. Reactive Distillation System – 3.3. Economical and Environmental indexes; Pgs. 5030-5033, 4.2. Reactive Distillation System, Table 4, Figs. 6-7; Pg. 5033, 5. Conclusions; and, MPEP 2141 and 2143 I. B-D.
For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to applications arguments on page 7 of the remarks filed on 06 February 2026 that “Applicants respectfully submit that the Examiner relies on an impermissible degree of hindsight in making the rejection”. It must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant’s disclosure, such a reconstruction is proper, see In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971) and MPEP 2145 X.A. Only knowledge which was within the level of ordinary skill in the art at the time the claimed invention was made has been applied to determine obviousness.
For the reasons indicated above, applicant’s above argument is not persuasive.
New and Previous Rejections Based on Amendments to the Claims in the reply filed on 06 February 2026
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.
For clarity between the new and previous rejections, the specific new rejections below are in italics.
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.
Claims 1-8 and 10-13 are newly rejected under 35 U.S.C. 103 as being obvious over Nair et al. (US20200062679, hereinafter Nair ‘679), as evidenced by Correia et al. (“Fire resistance of a water filled cooled structure”, June 2006, III European Conference on Computational Mechanics Solids, Structures and Coupled Problems in Engineering, Pgs. 1-12) and Cameo Chemicals, (“Chemical Datasheet, Trifluoroacetyl Chloride”, 13 December 2016, Wayback Machine, Pgs. 1-4), in view of Sanchez-Ramirez et al. (“Reactive Distillation Column Design for Tetraethoxysilane (TEOS) Production: Economic and Environmental Aspects”, 26 March 2018, Industrial & Engineering Chemistry Research, Vol. 57, Pgs. 5024-5034, hereinafter Sanchez-Ramirez), in further view of Nair et al. (US20200377366, published 03 December 2020, hereinafter Nair ‘366).
Nair ‘679 is in the known prior art field of “processes for the manufacture of trifluoroiodomethane and trifluoroacetyl iodide that produce surprisingly good process yields starting from hydrogen, iodine, and a trifluoroacetyl halide, such as trifluoroacetyl chloride”, see Abstract; Paras. [0019]-[0022], where the process comprises water up to “about 500 parts per million”, see Para. [0021], and minimal steps within one reactor, i.e., the first reactor, see Paras. [0027]-[0029];[0089]; Figs. 1-3. As detailed below, the Nair ‘679 process is not entirely a gas phase process as the process may run under operating conditions to include liquid water and liquid trifluoroacetyl chloride.
Nair ‘679 teaches the claims 1, 2, 4, 5, 6, 8, and 12 limitations of the production of trifluoroacetyl iodide on a commercial scale by providing a reactant stream 12 comprising hydrogen iodide and a reactant stream 14 comprising trifluoroacetyl chloride, mixing the streams in mixer valve 16, then directly reacting the reactant stream in column 20 in the presence of a first catalyst 24 at a first reaction temperature from about 50° C. to about 120° C. and a pressure of about 30 to 100 psig to produce an intermediate product stream 26 comprising trifluoroacetyl iodide, where it has been found that a lower reaction temperature, such as a first reaction temperature at or below about 120° C., the reaction can produce a low concentration of trifluoroiodomethane in the intermediate product stream and the concentration of trifluoroacetyl iodide in the intermediate product stream, in GC area % of total organic compounds, is about 90% to about 99% or about 95% to about 99%, see Claim 1; Paras. [0030];[0035];[0041]-[0044];[0081]-[0087], Fig. 1, meeting:
The product to be produced, reactant streams, the mixing, the combined reactant streams, the reacting in a column, and the crude/intermediate product stream in instant application claim 1;
Within the temperature and pressure range in instant application claim 1, in instant application claim 4, and in instant application claim 5;
The first catalysts is selected from activated carbon, meso carbon, stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, alumina, etc., see Para. [0030], meeting the specific catalysts in instant application claim 8;
The intermediate product stream 26 proceeds directly to a first distillation column 28, where the first distillation column is configured for the separation of some of the by-products, reactants, and organic compounds from the trifluoroacetyl iodide to produce a purified intermediate product stream 32 of trifluoroacetyl iodide, the first distillation column is configured to separate the hydrogen halide, such as HCl, into a hydrogen halide stream 38 for sale, reuse elsewhere, or disposal, and the concentration of the trifluoroacetyl iodide in the purified intermediate product stream is greater than about 98 weight percent (wt. %) provided that the purified intermediate product stream consist of at least 99.7 wt. % of trifluoroacetyl iodide, see Paras. [0027];[0049]-[0055];[0084]-[0087], Fig. 1. The distillation is run at a pressure of about 300 kPaG aka 43.5 psig and at a temperature of about 55° C, with hydrogen chloride taken off from the top of the column, and product from the bottom of the column, see Para. [0118], meeting:
The purification distillation column, the overhead stream of HCl, the purified product, and within the range of the yield of trifluoroacetyl iodide in instant application claim 1;
Within the temperature and pressure range in instant application claim 1 and in instant application claim 4;
The distillation purification in instant application claim 6;
Within the range of purity in instant application claim 12; and,
The molar ratio of trifluoroacetyl chloride to hydrogen iodide is about 1:1 or a CF3CoCl:HI mole ratio of 0.75 to 1.95 aka about 1:1.4 to about 2:1, see Paras. [0023]-[0025], Tables 4 and 7, meeting and within the molar ratio range in instant application claim 2.
Nair ‘679 does not specifically teach:
The instant application claim 1 limitations of reacting, in both vapor phase and liquid phase reactions.
Nair ‘679 teaches “[s]ome known methods of preparing trifluoroacetyl iodide include liquid-phase processes” that “can require solvents that must be separated out and disposed of” (emphasis added) that “make the processes less efficient”, see Para. [0007]. Nair ‘679 teaches the use of some solvents that may require disposal makes the process less efficient. Nair ‘679 does not “criticize, discredit, or otherwise discourage” the use of all solvents and liquid phase reactions, see MPEP 2145 X.D.1. On the contrary, Nair ‘679 teaches water is present in the gas phase process “in an amount by weight less than about 500 parts per million”, see Paras. [0019]-[0021], water in the process or created in the process will “hydrolyze the trifluoroacetyl halide and form the more thermodynamically favorable trifluoroacetic acid”, see Para. [0022], the catalytic reaction is performed from 40 ◦C to less than 100 ◦C at about 15 psig aka 1 bar, see Paras. [0026];[0035], the distillation is performed at about 55° C at about 43.5 psig aka 3 bar, see Para. [0118], and the purified trifluoroacetyl iodide stream contains an amount of trifluoroacetic acid, see Paras. [0051]-[0052]. Water is a liquid/not boiling from 40 ◦C to less than 100 ◦C at 1 bar to 3 bar, see Correia et al., Pg. 10, Fig. 6. Therefore, liquid water is present throughout the gas phase process of Nair ‘679, meeting the vapor/gas phase and liquid phase reactions in instant application claim 1.
In addition, Cameo Chemicals teaches trifluoroacetyl chloride is a liquid under it’s own vapor pressure, is a liquid when unconfined, and is a liquid that reacts with adsorbents, see Cameo Chemicals, Pg. 1, General Description and Pg. 2, Potential Incompatible Absorbents. Nair ‘679 teaches the reaction and the distillation take place at various temperatures and pressures including ambient temperature and pressure, see Paras. [0035];[0042]-[0043];[0118], the reactant stream 18 is provided directly to the reactor 20 bypassing heat exchange 22, see Fig. 1; Para. [0081], and the product stream 26 proceeds directly to the distillation column 28 bypassing heat exchange 30, see Fig. 1; Para. [0084], resulting in the reactant stream and product stream not being heated or cooled prior to the reactor or the distillation. Therefore, the trifluoroacetyl chloride within the reaction of Nair ‘679 may also be in a compressed liquid form and/or an unconfined liquid form, meeting the vapor/gas phase and liquid phase reactions in instant application claim 1.
The above teachings of Nair ‘679 would lead a person of ordinary skill in the art before the effective filing date of the claimed invention to the understanding that the Nair ‘679 process is not entirely a gas phase process as the process may run under operating conditions to include liquid water and liquid trifluoroacetyl chloride, see MPEP 2143 B & G.
Furthermore, “[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 a liquid phase, gas phase, and/or vapor phase reactions, “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 re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929)”, see MPEP 2144.05.
Nair ‘679 does not teach:
The instant application claim 1 limitations of reacting in a reactive distillation column comprising a reboiler;
The instant application claim 4 reactive distillation column reboiler temperature;
The instant application claim 5 reactive distillation column operated at a pressure; and,
The limitations of instant application claims 3, 7, and 13.
Nair ‘679 teaches reacting in a catalysts packed column 20 than separately separating and purifying in a distillation column 28, see Fig. 1; Paras. [0081]-[0087].
Sanchez-Ramirez relating to the efficiency problem to be solved by combining a catalytic acetalization reaction, distillation, and purification in one reactor by performing catalytic reactive distillation of a hydrocarbon and the simultaneous separation of HCl, see Abstract and Graphical Abstract; Pg. 5026, Col. 1, Last Full Para., teaches reactive distillation takes place in the both the liquid and vapor phases and the catalyst packed column comprises a reboiler that is used to heat the column and a condenser that is used to cool the tower to the optimal temperature, such as from about -60 °C to about 300 °C, depending upon the optimal reaction temperature for conversion, the boiling points of the products to be separated, the vapor−liquid equilibrium, and the reaction pressure, see Pg. 5026, Col. 1, Second Full Para.-Col. 2, Second Full Para.; Pg. 5028, 3.2. Reactive Distillation System – 3.3. Economical and Environmental indexes; Pgs. 5030-5033, 4.2. Reactive Distillation System, Table 4, Figs. 6-7; Pg. 5033, 5. Conclusions, meeting:
The packed reactive distillation column with a reboiler within the temperature range in instant application claim 1, in instant application claim 3, and in instant application claim 4;
The reactive distillation column operated at a pressure in instant application claim 5;
The reactive distillation column catalyst in instant application claim 7; and,
Within the range of the temperature of the overhead stream in instant application claim 13.
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 Nair ‘679 to combine the reactor and distillation columns into one integral packed bed reactive distillation column, see MPEP 2144.04 V. B., including a reboiler in the catalysts packed column to provide the appropriate reactive distillation column temperature and pressure profiles, as taught by Sanchez-Ramirez, with a reasonable predictability of success for the purpose of efficiently producing an acetyl by reacting and distilling in a one piece reactive distillation unit at the optimal reaction temperature for conversion, the optimal boiling points of the products to be separated, the optimal vapor−liquid equilibrium, and the optimal reaction pressure in order to achieve high conversion, yield, and purity; while, reducing operating costs and equipment size, see Sanchez-Ramirez, Abstract, Graphical Abstract; Pg. 5026, Col. 1, Second Full Para.-Col. 2, Second Full Para.
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 both Nair ‘679 and Sanchez-Ramirez teach catalytic reaction, distillation, and acetylation, a person of ordinary skill in the art has good reason to produce and purify the trifluoroacetyl iodide by pursuing the known options within their technical grasp for the benefit of efficiently producing an acetyl by reacting and distilling in a one piece reactive distillation unit at the optimal reaction temperature for conversion, the optimal boiling points of the products to be separated, the optimal vapor−liquid equilibrium, and the optimal reaction pressure in order to achieve high conversion, yield, and purity; while, reducing operating costs and equipment size, see Sanchez-Ramirez, Abstract, Graphical Abstract; Pg. 5026, Col. 1, Second Full Para.-Col. 2, Second Full Para. 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 addition, “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions,” such as reaction pressures and temperatures, “or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, 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 re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929)”, see MPEP 2144.05.
Nair ‘679 does not teach:
The instant application claim 1 limitations of wherein the combined reactant stream further comprises a solvent selected from the group consisting of benzene, toluene, xylenes, mesitylene (1,3,5-trimethylbenzene), ethyl benzene, dimethylformamide (DMF), dimethyl sulfoxide (DMSO), ionic liquids, and combinations thereof; and,
The limitations of instant application claims 10 and 11.
Nair ‘366 is in the known prior art field of a “process for the manufacture of hydrogen iodide (HI) from hydrogen (H2) and elemental iodine (I2) dissolved in a suitable solvent with use of at least one catalyst”, see Abstract, where “[h]ydrogen iodide is an important industrial chemical used as a reducing agent, as well as in the preparation of hydroiodic acid, organic and inorganic iodides, and iodoalkanes. However, hydrogen iodide is very difficult to handle due to its instability and reactivity”, see Para. [0003].
Regarding the limitations of instant application claims 1 and 10, Nair ‘366 teaches “providing a reactant stream comprising hydrogen (H2) and iodine (I2), the iodine dissolved in a suitable solvent which can be conveniently fed into a reactor by a liquid pump”, see Para. [0011], where “the hydrogen (H2) and the iodine (I2) dissolved in a solvent are fed to a preheater”, then the “mixture is then passed to a furnace containing a heated catalyst”, then the “product stream including hydrogen iodide (HI), unreacted hydrogen (H2), and unreacted iodine (I2) dissolved in a solvent is directed from the reactor to at least two cold traps”, see Paras. [0066]-[0070]; Fig. 1, where the suitable solvents “are stable under the elevated temperature reaction conditions and are non-reactive when exposed to the reagents, products, and catalysts present in the reaction”, and the suitable solvents include “at least one of ethers, such as diethyl ether and diglyme; nitriles, such as benzonitrile and acetonitrile; and formamides, such as dimethylformamide; ionic liquids, such as 1-ethyl-3-methylimidazolium acetate; sulfolane; carbon disulfide; toluene; naphthalene; xylene; 2,2-dimethylbutane; cyclohexane; ethanol; perfluoroheptane; and mesitylene”, see Paras. [0015]-[0023]; Table 1, specifically “[t]hermally stable solvents (vapor decomposition temperature >500° C.) such as toluene, benzonitrile, naphthalene may also be used, and can be recycled”, see Para. [0022], and the hydrogen, iodine, and solvent may each “be substantially free of water, including any water by weight in an amount less than about 500 ppm”, see Paras. [0024]-[0026], meeting the combined reactant stream including a suitable solvent, such as toluene, in instant application claim 1 and in instant application claim 10.
Regarding the limitations of instant application claim 11, Nair ‘366 teaches “[t]he product stream 22 may include hydrogen iodide (HI), unreacted iodine (I2) dissolved in the solvent, unreacted hydrogen (H2), and trace amounts of water. The product stream 22 may be directed to a first cold trap 24 where the product stream 22 may be cooled to permit collection of unreacted iodine (I2) dissolved in the solvent 32. The unreacted iodine dissolved in the solvent 32 may be recycled back to the dissolved iodine (I2) feed stream 10”, see Para. [0075]; Fig. 1, meeting the recovered I2 from a purified product stream in instant application claim 11.
In reference to the above claims, since Nair ‘679 does not “criticize, discredit, or otherwise discourage” the use of operating conditions that renders the reactants in liquid and vapor phases, or the use of a solvent, see MPEP 2145 X.D.1., even though the use of a solvent may be less efficient. On the contrary, as stated above, the Nair ‘679 process is not entirely a gas phase process as the process may run under operating conditions to include liquid water and liquid trifluoroacetyl chloride. 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 Nair ‘679 to include a suitable solvent and reactant recycle as taught by Nair ‘366 with a reasonable predictability of success for the purpose of efficiently producing an iodine product while controlling the instability and reactivity of the reactants, such as with solid or gaseous iodine, and products by dissolving the reactants in solvents that “are stable under the elevated temperature reaction conditions and are non-reactive when exposed to the reagents, products, and catalysts present in the reaction”, see Nair ‘366, Paras. [0003];[0011];[0017]-[0023]; Table 1.
A rationale to support a conclusion that the claim would have been obvious is that a particular known technique was recognized as part of the ordinary capabilities of one skilled in the art. Another rationale to support a conclusion that the claim would have been obvious is that the substitution of one known element for another yields predictable results to one of ordinary skill in the art. One of ordinary skill in the art would have been capable of modifying the process of Nair ‘679 by applying the known technique of the added solvent as taught by Nair ‘366 with a reasonable predictability of success for the purpose of efficiently producing an iodine product while controlling the instability and reactivity of the reactants, such as with solid or gaseous iodine, and products by dissolving the reactants in solvents that “are stable under the elevated temperature reaction conditions and are non-reactive when exposed to the reagents, products, and catalysts present in the reaction”, see Nair ‘366, Paras. [0003];[0011];[0017]-[0023]; Table 1; and MPEP 2143 I. B-D.
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 Nair ‘679 and Nair ‘366 both teach catalytic reactions involving hydrogen and iodine to produce iodide products, a person of ordinary skill in the art has good reason to modify Nair ‘679 by relying upon Nair ‘366 before the effective filing date of the claimed invention for knowledge generally available within the catalytic reactions involving hydrogen and iodine to produce iodide products art regarding a suitable choice of solvent, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing an iodine product while controlling the instability and reactivity of the reactants, such as with solid or gaseous iodine, and products by dissolving the reactants in solvents that “are stable under the elevated temperature reaction conditions and are non-reactive when exposed to the reagents, products, and catalysts present in the reaction”, see Nair ‘366, Paras. [0003];[0011];[0017]-[0023]; Table 1; and, MPEP 2141 and 2143 I. B-D.
“The discovery of a previously unappreciated property of a prior art composition,” such as the process to make trifluoroacetyl iodide with or without a specific solvent, “or of a scientific explanation for the prior art’s functioning, does not render the old composition patentably new to the discoverer”, see MPEP 2112 I.
Selection of a known material, such as a suitable 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 addition, “[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 a liquid phase, a gas phase, and/or a vapor phase reaction, “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 re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929)”, see MPEP 2144.05.
Conclusion
No claims are allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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/YO/Examiner, Art Unit 1692
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699
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