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 .
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 23 July 2026 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement has been considered by the examiner.
Status of the Claims
Claims 1-20 are currently pending.
Claims 1 and 10 are currently amended.
Response to Amendments
Applicant’s amendments filed on 23 July 2026 are acknowledged.
Claim Rejections - 35 USC § 103
Applicant’s amendments to claims 1 and 10 adding “wherein the dicarboxylate alkali salt transfers a carboxylate group to the aromatic ring and is converted to the decarboxylated alkali salt” not taught by the primary reference Kittrell is sufficient to overcome the rejection of claims 1-20 under 35 U.S.C. 103 as being unpatentable over Kittrell et al. (US20230020051, published 19 January 2023, filed 16 July 2021, hereinafter Kittrell) in view of Brownscombe et al. (WO2001016072, published 08 March 2001, hereinafter Brownscombe).
The rejection is withdrawn; however, due solely to the amendments to claims 1 and 10, new ground(s) of rejection is/are provided below.
Double Patenting
Applicant’s amendments to claims 1 and 10 adding “wherein the dicarboxylate alkali salt transfers a carboxylate group to the aromatic ring and is converted to the decarboxylated alkali salt” is taught by Brownscombe and is not sufficient to overcome the rejection of claims 1-20 on the ground of nonstatutory double patenting as being unpatentable over claims 1, 3-6, 8, 10, and 12-17 of copending Application No. 18506347 to Shi et al. (hereinafter Shi ‘347) in view of Brownscombe et al. (WO2001016072, published 08 March 2001, hereinafter Brownscombe).
The rejection is maintained; however, due solely to the amendments to claims 1 and 10, modified ground(s) of rejection is/are provided below.
Response to Arguments
Applicant’s arguments filed on 23 July 2026 have been fully considered but they are either moot or not persuasive.
Applicant’s argue that Kittrell and Brownscombe do not disclose the limitations as recited in amended claims 1 and 10. These arguments have been considered but are either moot or not persuasive for the reasons set forth in the new and modified grounds of rejection below and the response to arguments below.
Applicant’s arguments throughout the remarks filed on 23 July 2026 with respect to Kittrell have been considered but are moot because the new ground of rejection does not rely on Kittrell applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
In response to Applicant’s arguments on pages 5-7 of the remarks filed on 23 July 2026, that “the disclosure of Brownscombe states that the carboxyl sources for the carboxylation reaction is not the dicarboxylate salt but instead the basic carbonate salts and carbon dioxide gas”, “[t]here is no disclosure in Brownscombe that discloses or suggests that the dicarboxylate salt transfers a carboxyl group to the aromatic ring while being converted into a decarboxylated coproduct”, “Brownscombe therefore explains that dicarboxylate salts participate as reactive intermediates or initiators in the carboxylation process rather than as carboxylate-transfer reagents”, and “Brownscombe does not expressly disclose that a dicarboxylate salt transfers a carboxylate group to an aromatic substrate, nor does it provide any working example demonstrating such a reaction”.
Patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123. In this case, Brownscombe teaches the “direct carboxylation of aromatic hydrocarbons” by “a carboxyl source selected from basic carbonate containing salts and carbon dioxide”, see Abstract; Claim 1; Pg. 3, Lns. 11-27, where the basic carbonate containing salt has sufficient “molecular mobility” to incorporate its source carboxyl groups into an aromatic hydrocarbon, see Pg. 3, Ln. 11-Pg. 4, Ln. 2; Pg. 5, Lns. 1-30; Abstract; Claim 1, by mixing “the aromatic hydrocarbon and basic carbonate carboxyl salt”, such as dipotassium malonate, to accomplish the addition/transfer/molecular mobility of the “carboxyl to the aromatic hydrocarbon” resulting in the incorporation of “the aromatic hydrocarbon” into the structure of the “basic carbonate containing salt”, see Claims 1-8; Pg. 3, Lns. 6-28; Pg. 5, Ln. 1-Pg. 6, Ln. 25, where for example in a process dipotassium oxalate as the carboxyl source is reacted with naphthalene as the aromatic hydrocarbon to produce “2, 6-naphthalene dicarboxylic acid (NDCA)”, see Pg. 3, Ln. 11-Pg. 4, Ln. 2; Pg. 5, Lns. 1-30, i.e., both carboxylates from the oxalate are transferred to the aromatic compound.
“Where 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. Since Brownscombe teaches the “direct carboxylation of aromatic hydrocarbons” by “a carboxyl source selected from basic carbonate containing salts and carbon dioxide”, see Abstract; Claim 1; Pg. 3, Lns. 11-27, where the basic carbonate containing salt has sufficient “molecular mobility” to incorporate its source carboxyl groups into an aromatic hydrocarbon, see Pg. 3, Ln. 11-Pg. 4, Ln. 2; Pg. 5, Lns. 1-30; Abstract; Claim 1, “the dicarboxylate alkali salt transfers a carboxylate group to the aromatic ring and is converted to the decarboxylated alkali salt” as claimed in claims 1 and 10 will inherently also take place in the direct carboxylation of aromatic hydrocarbons of Brownscombe.
Brownscombe also teaches, as stated on pages 10-11 of the previous office action dated 24 April 2026, the addition of the carboxyl to the aromatic compound creates “a decarboxylated salt and the decarboxylated salt is recovered and regenerated back to a carboxylating salt, where “the basic potassium salts remaining can be converted back to oxalate or formate by well known reactions. (e.g., KOH + CO at 120°C —> potassium formate; potassium formate at > 200°C —> K2 Oxalate; etc.)”, see Pg. 3, Lns. 6-28; Pg. 5, Ln. 1-Pg. 6, Ln. 25”; Claims 1-8, where for example in a process dipotassium oxalate as the carboxyl source is reacted with naphthalene as the aromatic hydrocarbon to produce “2, 6-naphthalene dicarboxylic acid (NDCA)”, see Pg. 3, Ln. 11-Pg. 4, Ln. 2; Pg. 5, Lns. 1-30, i.e., both carboxylates from the oxalate are transferred to the aromatic compound resulting in KOH.
Therefore, Brownscombe teaches the carboxyl source is the dicarboxylate salt, such as dipotassium malonate, the dicarboxylate salt transfers a carboxyl group to the aromatic ring, and the dicarboxylate salt is converted into a decarboxylated salt after the transfer.
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 stating the alkali metal salt transfers the carboxylate to the aromatic instead of stating the alkali metal salt incorporates or has molecular mobility to the aromatic, “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.
For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to Applicant’s arguments on pages 6-7 of the remarks filed on 23 July 2026, that the “experimental example employs potassium furoate and dipotassium malonate under a CO2 atmosphere and demonstrates successful formation of FDCA-derived products without the addition of any separate alkali carbonate reagent”. 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.
In this case, Brownscombe teaches the “basic carboxylating salts may also be mixed with potassium carbonate” (emphasis added), see Pg. 5, Lns. 24-28 and “further comprising that the carboxylating salts may also be mixed with potassium carbonate”, see Claim 9. Therefore, Brownscombe also teaches the reaction takes place without the addition of any separate alkali carbonate reagent.
In addition, claims 1 and 10 of the instant application state “the process comprising: …”. MPEP 2111.03 I. states “[t]he transitional term “comprising”, which is synonymous with “including,” “containing,” or “characterized by,” is inclusive or open-ended and does not exclude additional, unrecited elements or method steps”. Therefore, the instantly claimed steps do not “exclude additional, unrecited elements or method steps”. As a result, additional reactants may be added to the reaction that is claimed in instant application claims 1 and 10.
For the reasons indicated above, applicant’s above arguments are not persuasive.
Double Patenting
Applicant’s arguments on page 7 of the remarks filed on 23 July 2026 that “Brownscombe, alone or in combination, require or suggest that “the dicarboxylate alkali salt transfers a carboxylate group to the aromatic ring and is converted to the decarboxylated alkali salt" as recited in claims 1 and 10”. Please see the response to arguments above detailing Brownscombe teaches the carboxyl source is the dicarboxylate salt, such as dipotassium malonate, the dicarboxylate salt transfers a carboxyl group to the aromatic ring, and the dicarboxylate salt is converted into a decarboxylated salt after the transfer.
Therefore, applicant’s above arguments are not persuasive for the reasons set forth in the response to arguments above and in the modified grounds of rejection below.
In the Spirit of Compact Prosecution
While 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.
New, Maintained, and Modified Rejections Based on Amendments to the Claims in the reply filed on 23 July 2026
Specification
Title of the Invention
The title of the invention is objected to because of the following informalities:
The title of the invention is not descriptive. A new title is required that is clearly indicative of the invention to which the claims are directed.
Appropriate correction is required.
For clarity between the new, modified, and maintained rejections, the specific new and modified 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, 3-5, 9, 10, 12, 14, 15, and 20 are newly rejected under 35 U.S.C. 103 as being unpatentable over Brownscombe et al. (WO2001016072, published 08 March 2001, hereinafter Brownscombe).
Brownscombe is in the known prior art field of processes for “synthesizing aromatic acids and diacids which comprises reacting aromatic hydrocarbons with a carboxyl source selected from basic carbonate containing salts and carbon dioxide at elevated temperature under conditions in which said carboxyl source exhibits sufficient mobility to effect a net reaction to form aromatic acid salts, and aromatic polyacid salts, incorporating the aromatic hydrocarbon used in the reaction into their structure”, see Abstract,
Regarding the limitations of instant application claims 1, 3, 9, 10, 12, and 20, Brownscombe teaches “[a] process for synthesizing aromatic acids and polyacids, particularly diacids, which comprises reacting aromatic hydrocarbons with a carboxyl source selected from basic carbonate containing salts in the presence of carbon dioxide at an elevated temperature under conditions in which said carbonate salt mixture exhibits sufficient molecular mobility to effect a net reaction with the aromatic hydrocarbon to form aromatic acid salts, and aromatic polyacid salts, incorporating the aromatic hydrocarbon used in the reaction into their structure”, where mixing “the aromatic hydrocarbon and basic carbonate carboxyl salt”, such as dipotassium malonate, to accomplish the addition/transfer/molecular mobility of the “carboxyl to the aromatic hydrocarbon” resulting in the incorporation of “the aromatic hydrocarbon” into the structure of the “basic carbonate containing salt”, see Claims 1-8; Pg. 3, Lns. 6-28; Pg. 5, Ln. 1-Pg. 6, Ln. 25, where for example in a process dipotassium oxalate as the carboxyl source is reacted with naphthalene as the aromatic hydrocarbon to produce “2, 6-naphthalene dicarboxylic acid (NDCA)”, see Pg. 3, Ln. 11-Pg. 4, Ln. 2; Pg. 5, Lns. 1-30, i.e., both carboxylates from the oxalate are transferred to the aromatic compound, meeting:
The process of conducting a carboxylate transfer reaction to an aromatic compound from a basic carbonate carboxyl salt, the mixture, the heating in the presence of CO2 to form a carboxylated aromatic compound in instant application claim 1 and in instant application claim 10;
The 1,3-dicarboxylate alkali salt, dipotassium malonate, in instant application claim 3 and in instant application claim 12;
The addition of the carboxyl to the aromatic compound creates a decarboxylated salt and the decarboxylated salt is recovered and regenerated back to a carboxylating salt, where “the basic potassium salts remaining can be converted back to oxalate or formate by well known reactions. (e.g., KOH + CO at 120°C —> potassium formate; potassium formate at > 200°C —> K2 Oxalate; etc.)”, see Pg. 3, Lns. 6-28; Pg. 5, Ln. 1-Pg. 6, Ln. 25; Claims 1-8, where for example in a process dipotassium oxalate as the carboxyl source is reacted with naphthalene as the aromatic hydrocarbon to produce “2, 6-naphthalene dicarboxylic acid (NDCA)”, see Pg. 3, Ln. 11-Pg. 4, Ln. 2; Pg. 5, Lns. 1-30, i.e., both carboxylates from the oxalate are transferred to the aromatic compound resulting in KOH, meeting:
The decarboxylated alkali salt created from the removal of carboxyl from the basic dicarbonate carboxyl salt in instant application claim 1 and in instant application claim 10;
The regenerating in instant application claim 9 and in instant application claim 20; and,
The reaction is conducted in a vessel in a reaction zone with passing of the reactants into the vessel, such as a flow reactor, see Pg. 8, Lns. 13-32; Pg. 11, Lns. 11-15; Pg. 11, Ln. 24-Pg. 13, Ln. 2, meeting:
The reactor vessel and passing in instant application claim 10.
Further regarding instant application claims 1 and 10, “[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, Brownscombe teaches the “direct carboxylation of aromatic hydrocarbons” by “a carboxyl source selected from basic carbonate containing salts and carbon dioxide”, see Abstract; Claim 1; Pg. 3, Lns. 11-27, where the basic carbonate containing salt has sufficient “molecular mobility” to incorporate its source carboxyl groups into an aromatic hydrocarbon, see Pg. 3, Ln. 11-Pg. 4, Ln. 2; Pg. 5, Lns. 1-30; Abstract; Claim 1. Therefore, “the dicarboxylate alkali salt transfers a carboxylate group to the aromatic ring and is converted to the decarboxylated alkali salt” as claimed in claims 1 and 10 will inherently also take place in the direct carboxylation of aromatic hydrocarbons of Brownscombe.
Regarding the limitations of instant application claims 4 and 14, Brownscombe teaches “wherein the temperature is in the range of 350-550°C” and “reaction conditions further comprise C02 pressure of 100-1000 psig”, see Claims 15-18; Pg. 7, Ln. 28-Pg. 8, Ln. 12, meeting:
Within the temperature and pressure range in instant application claim 4 and in instant application claim 14.
Regarding the limitations of instant application claims 5 and 15, Brownscombe teaches “[t]he use of a molten solvent or diluent medium may facilitate transfer of the reacting mass from vessel to vessel and improve mixing, however it is not necessary to the practice of the invention. If a diluent medium is used, it should be liquid, stable at the temperatures employed, and, if inert, a material which does not undesirably affect the reaction”, where “[t]he materials are often solids, in which case it is convenient to add mixed powders to the reaction zone. Liquids, and even gases, may be used for the reaction”, see Pg. 7, Ln. 28-Pg. 8, Ln. 32, i.e., a slurry, meeting:
The slurry mixture in instant application claim 5 and in instant application claim 15.
Brownscombe does not specifically teach:
The above limitations in one single express embodiment.
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 Brownscombe to choose the desired reaction materials, pressures, and temperatures with a reasonable predictability of success for the purpose of efficiently “synthesizing aromatic acids and diacids” “at a reduced cost in significantly improved purity without the necessity of oxidation reactions or purification of alkyl hydrocarbon isomers, both of which are expensive and difficult” by reacting “basic carbonate containing salts in the presence of carbon dioxide at an elevated temperature under conditions in which said carbonate salt mixture exhibits sufficient molecular mobility to effect a net reaction with the aromatic hydrocarbon to form aromatic acid salts, and aromatic polyacid salts, incorporating the aromatic hydrocarbon used in the reaction into their structure”, see Brownscombe, Abstract; Pg. 1, Lns. 9-23; Pg. 5, Ln. 1-Pg. 6, Ln. 25; Claim 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 Brownscombe to select the optimal reaction materials, pressures, and temperatures by applying the differing known reaction materials, pressures, and temperatures as taught by Brownscombe with a reasonable predictability of success for the purpose of efficiently “synthesizing aromatic acids and diacids” “at a reduced cost in significantly improved purity without the necessity of oxidation reactions or purification of alkyl hydrocarbon isomers, both of which are expensive and difficult” by reacting “basic carbonate containing salts in the presence of carbon dioxide at an elevated temperature under conditions in which said carbonate salt mixture exhibits sufficient molecular mobility to effect a net reaction with the aromatic hydrocarbon to form aromatic acid salts, and aromatic polyacid salts, incorporating the aromatic hydrocarbon used in the reaction into their structure”, see Brownscombe, Abstract; Pg. 1, Lns. 9-23; Pg. 5, Ln. 1-Pg. 6, Ln. 25; Claim 1; and MPEP 2143 I. B-D.
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 any of the reaction materials, pressures, and temperatures of Brownscombe, 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.
“It 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 stating the alkali metal salt transfers the carboxylate to the aromatic instead of stating the alkali metal salt incorporates or has molecular mobility to the aromatic, “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.
Claims 2, 6-8, 11, 13, and 16-19 are newly rejected under 35 U.S.C. 103 as being unpatentable over Brownscombe et al. (WO2001016072, published 08 March 2001, hereinafter Brownscombe), as applied in the 35 USC 103 rejection of claims 1, 3-5, 9, 10, 12, 14, 15, and 20 above, in further view of Kittrell et al. (US20230020051, published 19 January 2023, filed 16 July 2021, hereinafter Kittrell).
Regarding the limitations of instant application claims 2, 8, 11, and 13, Brownscombe teaches mixing “the aromatic hydrocarbon and basic carbonate carboxyl salt”, such as dipotassium malonate, to accomplish the addition/transfer/ molecular mobility of “carboxyl to the aromatic hydrocarbon” resulting in the incorporation of “the aromatic hydrocarbon” into the structure of the “basic carbonate containing salt”, see Claims 1-8; Pg. 3, Lns. 6-28; Pg. 5, Ln. 1-Pg. 6, Ln. 25; Claim 1, meeting:
The dicarboxylate alkali base salt counter ion and malonate, dipotassium malonate, in instant application claim 2, in instant application claim 8, in instant application claim 11, and in instant application claim 13.
Brownscombe does not teach:
The instant application claims 2 and 11 limitations of the aromatic hydrocarbon further comprises a counter ion;
The instant application claims 8 and 13 limitations of the aromatic ring comprises a furoate; and,
The limitations if instant application claims 6, 7, and 16-19.
Kittrell is in the known prior art field of “the preparation of furandicarboxylic acid (FDCA), especially 2,5-FDCA, from a furan derivatized carboxylate salt produced from sugar bearing sources such as C5 and C6 sugar bearing sources, especially C5 sugar bearing sources”, see Paras. [0001];[0007]-[0012]; Figs. 1-3 and 5, where the FDCA is a precursor for deriving polyesters, see Para. [0002], the “FDCA alkali metal” salts are produced which are “protonated to FDCA and precipitated out of solution”, and an alkali metal salt is regenerated, recovered, and recycled, see Paras. [0058]-[0059]; Figs. 3 and 6-10.
Regarding the limitations of instant application claims 2, 8, 11, and 13, Kittrell teaches in Example 1 a carboxylation reaction/carboxylate transfer reaction with “a cesium furoate conversion of 81.5% and a 2,5-furan dicarboxylate selectivity of 95% was achieved”, see Paras. [0069]-[0073]; Fig. 1, where a solution of a furoate, an alkali carbonate salt, and a stearate salt is prepared and placed in a Parr reactor, then “[a] hydrocarbon suspension fluid, such as in this case, Iso Par V produced by ExxonMobil, was then pumped directly to the Parr reactor, providing a 7:1 mass ratio of suspension fluid to solids (cesium furoate/cesium carbonate/cesium stearate). The reaction was then initiated at 260° C., at 8 bar pressure, and 60 mL/min CO2 flow rate for a period of 5 hours. Upon completion, the reactor was evacuated of its contents.”, see Paras. [0069]-[0071]; Figs. 3 and 5. “FDCA alkali metal” salts are produced which are “protonated to FDCA and precipitated out of solution”, where 2,5-furan dicarboxylate acid, 2,4 FDCA, 2,3 FDCA, and 3,4 FDCA are recovered, see Paras. [0058]-[0059];[0072]-[0073]; Fig. 3. The furoate is selected from “Li, Na, K, Rb, or Cs” furoate, see Paras. [0008];[0061], meeting:
The process for conducting a carboxylate transfer reaction, the mixing step of an aromatic, i.e., potassium furoate, and an alkali carbonate salt, and the heating step with CO2 to form carboxylated aromatic compounds, i.e., FDCA alkali metal salts, with the aromatic potassium furoate in instant application claim 2, in instant application claim 8, in instant application claim 11, and in instant application claim 13.
Regarding the limitations of instant application claims 5, 6, 15, and 16, Kittrell teaches in Example 1 “[a] hydrocarbon suspension fluid, such as in this case, Iso Par V produced by ExxonMobil, was then pumped directly to the Parr reactor, providing a 7:1 mass ratio of suspension fluid to solids (cesium furoate/cesium carbonate/cesium stearate).”, see Para. [0071], where as depicted in Fig. 5 the reactants are in bead solid form contacted with CO2 bubbles in the suspension fluid 308 slurry, see Fig. 5; Paras. [0010]-[0013];[0055], meeting the hydrocarbon slurry in instant application claim 5, in instant application claim 6, in instant application claim 15, and in instant application claim 16.
Regarding the limitations of instant application claims 7 and 17, Kittrell teaches in Example 1 “[t]he reaction was then initiated at 260° C., at 8 bar pressure, and 60 mL/min CO2 flow rate for a period of 5 hours.”, see Para. [0071], where as depicted in Fig. 5 the CO2 is in bubbles in a “counter-current” flow, see Fig. 5; Paras. [0052];[0055], meeting the CO2 is in a bubbling counter current flow in instant application claim 7 and in instant application claim 17.
Regarding the limitations of instant application claim 18, Kittrell teaches in Example 1 “[t]he solids were recovered by vacuum filtration using a Buchner funnel and Whatman qualitative filtering paper (Block 600 FIG. 3)” to obtain filtered solids of FDCA alkali metal salts, i.e. separated from the hydrocarbon suspension, see Paras. [0058]-[0059];[0071]-[0072]; Fig. 3, meeting the separating the carboxylated aromatic compound from the hydrocarbon suspension slurry in instant application claim 18.
Regarding the limitations of instant application claim 19, Kittrell teaches as depicted in Fig. 3, the separated hydrocarbon suspension from Block 600 of Example 1 is recycled back to Block 400 as line 310 for mixing with the cesium furoate, cesium carbonate, and cesium stearate to form the slurry, see Fig. 3; Paras. [0049];[0057];[0072], meeting recycling the separated hydrocarbon to form the slurry in instant application claim 19.
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 aromatic, the diluent liquid, and the CO2 flow of Brownscombe as taught by Kittrell and to add a diluent recycle to Brownscombe as taught by Kittrell with a reasonable predictability of success for the purpose of efficiently synthesizing aromatic furandicarboxylic acid (FDCA), “where the furoate is carboxylated using a continuous CO2 feed stream to produce the desired product 2,5-furandicarboxylic acid (2,5 FDCA)” by “feeding a slurry containing a suspension fluid, furoate, a surfactant and an alkali metal carbonate to a carboxylation reactor” in order to synthesize the FDCA with a reduction of complicated method steps, reaction time, costly catalysts, and environmental toxins, see Kittrell, Paras. [0001]-[0005];[0036]-[0037]; Claim 1.
The 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 aromatic, the diluent liquid, and the CO2 flow of Brownscombe along with the addition of a diluent recycle to Brownscombe by applying the known techniques as taught by Kittrell with a reasonable predictability of success for the purpose of efficiently synthesizing aromatic furandicarboxylic acid (FDCA), “where the furoate is carboxylated using a continuous CO2 feed stream to produce the desired product 2,5-furandicarboxylic acid (2,5 FDCA)” by “feeding a slurry containing a suspension fluid, furoate, a surfactant and an alkali metal carbonate to a carboxylation reactor” in order to synthesize the FDCA with a reduction of complicated method steps, reaction time, costly catalysts, and environmental toxins, see Kittrell, Paras. [0001]-[0005];[0036]-[0037]; Claim 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 Brownscombe and Kittrell both teach synthesizing aromatic acids by reacting aromatic hydrocarbons with a carboxyl source selected from basic carbonate containing salts and carbon dioxide at elevated temperature, a person of ordinary skill in the art has good reason to modify Brownscombe by relying upon Kittrell before the effective filing date of the claimed invention for knowledge generally available within the synthesis of aromatic acids art, see MPEP 2143 B & G and 2141, for the benefit of efficiently synthesizing aromatic furandicarboxylic acid (FDCA), “where the furoate is carboxylated using a continuous CO2 feed stream to produce the desired product 2,5-furandicarboxylic acid (2,5 FDCA)” by “feeding a slurry containing a suspension fluid, furoate, a surfactant and an alkali metal carbonate to a carboxylation reactor” in order to synthesize the FDCA with a reduction of complicated method steps, reaction time, costly catalysts, and environmental toxins, see Kittrell, Paras. [0001]-[0005];[0036]-[0037]; Claim 1; and, MPEP 2141 and 2143 I. B-D.
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 aromatic compounds and hydrocarbon diluents, 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.
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).
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Claims 1-20 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 3-5, 8, 10, 12, 13, and 17 of copending Application No. 18506347 to Shi et al. (hereinafter Shi ‘347) in view of Brownscombe et al. (WO2001016072, published 08 March 2001, hereinafter Brownscombe).
This is a provisional nonstatutory double patenting rejection.
Regarding instant application claim 1, the claims of Shi ‘347 recite a process for conducting a reaction, see Claim 1, the process comprising: mixing an aromatic ring with an alkali salt to form a mixture, see Claims 1 and 8; and, heating the mixture in the presence of carbon dioxide to form a carboxylated aromatic compound, see Claim 1.
Regarding instant application claim 2, the claims of Shi ‘347 recite wherein the aromatic ring further comprises a counter ion, and wherein the dicarboxylate alkali base, the counter ion, or both are selected from a group consisting of: lithium, sodium, potassium, rubidium, cesium, and mixtures thereof, see Claim 8.
Regarding instant application claim 4, the claims of Shi ‘347 recite wherein the mixture is heated to a temperature between 120 °C to 400 °C at a pressure up to 6,895 kPa (1,000 psi), see Claim 3.
Regarding instant application claim 5, the claims of Shi ‘347 recite wherein the mixture comprises a slurry, see Claim 1.
Regarding instant application claim 6, the claims of Shi ‘347 recite wherein the slurry is formed in a hydrocarbon, see Claim 1.
Regarding instant application claim 7, the claims of Shi ‘347 recite wherein the carbon dioxide is provided as bubbles which flow counter current, see Claims 4 and 5.
Regarding instant application claim 8, the claims of Shi ‘347 recite wherein the aromatic ring comprises a furoate, see Claim 1.
Regarding instant application claim 10, the claims of Shi ‘347 recite a process for producing a carboxylated aromatic compound, see Claim 10, the process comprising: passing an aromatic hydrocarbon and an alkali salt to a vessel in a reaction zone to form a mixture, see Claim 10; and, passing carbon dioxide into the vessel to contact the mixture, see Claim 10; and, heating the mixture to form a carboxylated aromatic compound, see Claim 10.
Regarding instant application claim 11, the claims of Shi ‘347 recite wherein the aromatic hydrocarbon further comprises a counter ion, and wherein the dicarboxylate alkali base, the counter ion, or both are selected from a group consisting of: lithium, sodium, potassium, rubidium, cesium, and mixtures thereof, see Claim 12.
Regarding instant application claim 13, the claims of Shi ‘347 recite wherein the aromatic ring comprises a furoate, see Claim 10.
Regarding instant application claim 14, the claims of Shi ‘347 recite wherein the mixture is heated to a temperature between 120 °C to 400 °C at a pressure up to 6,895 kPa (1,000 psi), see Claim 13.
Regarding instant application claim 15, the claims of Shi ‘347 recite wherein the mixture comprises a slurry, see Claim 10.
Regarding instant application claim 16, the claims of Shi ‘347 recite wherein the slurry is formed in a hydrocarbon, see Claim 10.
Regarding instant application claim 17, the claims of Shi ‘347 recite wherein the carbon dioxide is provided as bubbles which flow counter current, see Claim 14.
Regarding instant application claim 18, the claims of Shi ‘347 recite further comprising: separating the carboxylated aromatic compound from the hydrocarbon forming the slurry, see Claims 1 and 10.
Regarding instant application claim 19, the claims of Shi ‘347 recite further comprising: recycling the hydrocarbon forming the slurry, see Claim 17.
The claims of Shi ‘347 do not recite:
The instant application claim 1 limitations of a carboxylate transfer reaction, a dicarboxylate alkali salt, and forming a decarboxylated alkali salt;
The instant application claims 8 and 13 limitations of the dicarboxylate alkali salt is malonate;
The instant application claim 10 limitations of a dicarboxylate alkali salt and forming a decarboxylated alkali salt
The limitations of instant application claims 3, 9, 12, and 20.
Brownscombe is in the known prior art field of processes for “synthesizing aromatic acids and diacids which comprises reacting aromatic hydrocarbons with a carboxyl source selected from basic carbonate containing salts and carbon dioxide at elevated temperature under conditions in which said carboxyl source exhibits sufficient mobility to effect a net reaction to form aromatic acid salts, and aromatic polyacid salts, incorporating the aromatic hydrocarbon used in the reaction into their structure”, see Abstract.
Regarding the limitations of instant application claims 1, 8-10, 13, and 20, Brownscombe teaches a carboxylate transfer reaction where aromatic hydrocarbons are reacted with “basic carboxylating salts”, such as sodium, cesium, rubidium, or potassium malonate or oxalate, i.e., dicarboxylate alkali salts, and sodium, cesium, rubidium, or potassium carbonate, to transfer the carboxylate from the salt to the aromatic compound creating a decarboxylated salt and the decarboxylated salt is recovered and regenerated back to a carboxylating salt, where “the basic potassium salts remaining can be converted back to oxalate or formate by well known reactions. (e.g., KOH + CO at 120°C —> potassium formate; potassium formate at > 200°C —> K2 Oxalate; etc.)”, see Pg. 3, Lns. 6-28; Pg. 5, Ln. 1-Pg. 6, Ln. 25, meeting:
A carboxylate transfer reaction, a dicarboxylate alkali salt of sodium, cesium, rubidium, or potassium malonate, and forming a decarboxylated alkali salt, i.e. potassium formate, in instant application claim 1, in instant application claim 8, in instant application claim 10, and in instant application claim 13; and,
The regenerating the dicarboxylate alkali salt in instant application claim 9 and in instant application claim 20.
Regarding the limitations of instant application claims 3 and 12, Brownscombe teaches “basic carboxylating salts”, such as sodium, cesium, rubidium, or potassium malonate aka a 1,3-dicarboxylic acid salt, see Pg. 5, Ln. 1-Pg. 6, Ln. 25, meeting the specific dicarboxylic alkali salt in instant application claim 3 and in instant application claim 12.
The claims of Shi ‘347 do not recite:
The instant application claims 1 and 10 limitations of “wherein the dicarboxylate alkali salt transfers a carboxylate group to the aromatic ring and is converted to the decarboxylated alkali salt”.
Regarding the limitations of instant application claims 1 and 10, Brownscombe teaches “[a] process for synthesizing aromatic acids and polyacids, particularly diacids, which comprises reacting aromatic hydrocarbons with a carboxyl source selected from basic carbonate containing salts in the presence of carbon dioxide at an elevated temperature under conditions in which said carbonate salt mixture exhibits sufficient molecular mobility to effect a net reaction with the aromatic hydrocarbon to form aromatic acid salts, and aromatic polyacid salts, incorporating the aromatic hydrocarbon used in the reaction into their structure”, where mixing “the aromatic hydrocarbon and basic carbonate carboxyl salt”, such as dipotassium malonate, to accomplish the addition/transfer/molecular mobility of the “carboxyl to the aromatic hydrocarbon” resulting in the incorporation of “the aromatic hydrocarbon” into the structure of the “basic carbonate containing salt”, see Claims 1-8; Pg. 3, Lns. 6-28; Pg. 5, Ln. 1-Pg. 6, Ln. 25, where for example in a process dipotassium oxalate as the carboxyl source is reacted with naphthalene as the aromatic hydrocarbon to produce “2, 6-naphthalene dicarboxylic acid (NDCA)”, see Pg. 3, Ln. 11-Pg. 4, Ln. 2; Pg. 5, Lns. 1-30, i.e., both carboxylates from the oxalate are transferred to the aromatic compound, meeting:
The process of conducting a carboxylate transfer reaction to an aromatic compound from a basic carbonate carboxyl salt, the mixture, the heating in the presence of CO2 to form a carboxylated aromatic compound in instant application claim 1 and in instant application claim 10; and,
The addition of the carboxyl to the aromatic compound creates a decarboxylated salt and the decarboxylated salt is recovered and regenerated back to a carboxylating salt, where “the basic potassium salts remaining can be converted back to oxalate or formate by well known reactions. (e.g., KOH + CO at 120°C —> potassium formate; potassium formate at > 200°C —> K2 Oxalate; etc.)”, see Pg. 3, Lns. 6-28; Pg. 5, Ln. 1-Pg. 6, Ln. 25; Claims 1-8, where for example in a process dipotassium oxalate as the carboxyl source is reacted with naphthalene as the aromatic hydrocarbon to produce “2, 6-naphthalene dicarboxylic acid (NDCA)”, see Pg. 3, Ln. 11-Pg. 4, Ln. 2; Pg. 5, Lns. 1-30, i.e., both carboxylates from the oxalate are transferred to the aromatic compound resulting in KOH, meeting:
The decarboxylated alkali salt created from the removal of carboxyl from the basic dicarbonate carboxyl salt in instant application claim 1 and in instant application claim 10.
Further regarding instant application claims 1 and 10, “[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, Brownscombe teaches the “direct carboxylation of aromatic hydrocarbons” by “a carboxyl source selected from basic carbonate containing salts and carbon dioxide”, see Abstract; Claim 1; Pg. 3, Lns. 11-27, where the basic carbonate containing salt has sufficient “molecular mobility” to incorporate its source carboxyl groups into an aromatic hydrocarbon, see Pg. 3, Ln. 11-Pg. 4, Ln. 2; Pg. 5, Lns. 1-30; Abstract; Claim 1. Therefore, “the dicarboxylate alkali salt transfers a carboxylate group to the aromatic ring and is converted to the decarboxylated alkali salt” as claimed in claims 1 and 10 will inherently also take place in the direct carboxylation of aromatic hydrocarbons of Brownscombe.
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 alkali salt in the claims of Shi ‘347 to choose the “basic carboxylating salts”, regeneration, and transfer as taught by Brownscombe with a reasonable predictability of success for the purpose of efficiently “synthesizing aromatic acids and diacids” “at a reduced cost in significantly improved purity without the necessity of oxidation reactions or purification of alkyl hydrocarbon isomers, both of which are expensive and difficult” by reacting “basic carbonate containing salts and carbon dioxide at elevated temperature under conditions in which said carboxyl source exhibits sufficient mobility to effect a net reaction to form aromatic acid salts, and aromatic polyacid salts, incorporating the aromatic hydrocarbon used in the reaction into their structure”, see Brownscombe, Abstract; Pg. 1, Lns. 9-23; Pg. 5, Ln. 1-Pg. 6, Ln. 25.
The 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. One of ordinary skill in the art would have been capable of modifying the alkali salt source in the claims of Shi ‘347 by applying the known technique of carboxylate transfer reactions with the “basic carboxylating salts” as taught by Brownscombe with a reasonable predictability of success for the purpose of efficiently “synthesizing aromatic acids and diacids” “at a reduced cost in significantly improved purity without the necessity of oxidation reactions or purification of alkyl hydrocarbon isomers, both of which are expensive and difficult” by reacting “basic carbonate containing salts and carbon dioxide at elevated temperature under conditions in which said carboxyl source exhibits sufficient mobility to effect a net reaction to form aromatic acid salts, and aromatic polyacid salts, incorporating the aromatic hydrocarbon used in the reaction into their structure”, see Brownscombe, Abstract; Pg. 1, Lns. 9-23; Pg. 5, Ln. 1-Pg. 6, Ln. 25; 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 the claims of Shi ‘347 and Brownscombe both teach synthesizing aromatic acids by reacting aromatic hydrocarbons with a carboxyl source selected from basic carbonate containing salts and carbon dioxide at elevated temperature, a person of ordinary skill in the art has good reason to modify the claims of Shi ‘347 by relying upon Brownscombe before the effective filing date of the claimed invention for knowledge generally available within the synthesis of aromatic acids art, see MPEP 2143 B & G and 2141, for the benefit of efficiently “synthesizing aromatic acids and diacids” “at a reduced cost in significantly improved purity without the necessity of oxidation reactions or purification of alkyl hydrocarbon isomers, both of which are expensive and difficult” by reacting “basic carbonate containing salts and carbon dioxide at elevated temperature under conditions in which said carboxyl source exhibits sufficient mobility to effect a net reaction to form aromatic acid salts, and aromatic polyacid salts, incorporating the aromatic hydrocarbon used in the reaction into their structure”, see Brownscombe, Abstract; Pg. 1, Lns. 9-23; Pg. 5, Ln. 1-Pg. 6, Ln. 25; and, MPEP 2141 and 2143 I. B-D.
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 monocarboxylic acid alkali salts or dicarboxylic acid alkali salts, 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 monocarboxylic acid alkali salts substituted for dicarboxylic acid alkali salts and stating the alkali metal salt transfers the carboxylate to the aromatic instead of stating the alkali metal salt incorporates or has molecular mobility to the aromatic, “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
