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 12/11/2024 was filed in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Claim Objections
Claim 20 is objected to because of the following informalities: Claim 20 ends with an improper character; it should end with a period. Appropriate correction is required.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim(s) 1-11, 13-15 and 17-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over US 9,701,652 B2 to Miller et al.
Miller et al. teaches methods of forming FDCA compounds from hexose diacid compounds in the presence of an acid catalyst with an ionic liquid. See whole document and Example 1, Col. 7-14. Exemplary embodiments utilize mucic (galactaric) and saccharic (glucaric) acids as the hexose diacid compound; sulfuric acid as the acid catalyst; and 1-butyl-3-methylimidazolium sulfate as the ionic liquid. See Col, 7, lines 61-67; Col. 8, lines 2-4.
Miller et al. does not teach an embodiment wherein the ionic liquid comprises an anion moiety selected from halogen ions.
Miller et al. teaches that the ionic liquid can comprise a counter anion selected from the group consisting of, chloride, bromide, and iodide. This amounts to an art-recognized equivalence between sulfate and halogen anions such as chloride, bromide and iodide, and it would have therefore been obvious to substitute the sulfate taught in the exemplary embodiment with a halogen anion such as chloride, bromide and iodide. See MPEP 2144.06(II). With respect to claim 6, Miller teaches the use of aldaric acids from biomass materials (Abstract). With respect to claim 9, Miller et al. teaches “Various acid catalysts may be used … the acid catalyst is selected from the group consisting of a liquid phase organic sulfonic acid (e.g., a Sulfonic acid including a linear or branched alkyl group of 1 to 4 or 1 to 20 carbon atoms (e.g., substituted or unsubstituted)” (Col. 3, second paragraph). This amounts to an art-recognized equivalence of the sulfuric acid used in the exemplary embodiment and trifluoromethanesulfonic acid (a fluoroalkyl substituted sulfonic acid), and it would have therefore been obvious to substitute the sulfuric acid taught in the exemplary embodiment with trimethanesulfonic acid. See MPEP 2144.06(II). With respect to claims 9 and 10, Miller et al. does not teach the use of either a co-catalyst or additional organic solvent. With respect to claims 14 and 17, Miller et al. teaches wherein the reaction medium is substantially free from water, the reaction medium containing less than 1 wt. % water (claim 17). With respect to claims 15 and 19, exemplary embodiments in Table 3 (Col. 9) teach temperatures within the claimed ranges, for example see Sample R5-pdt at a reaction temperature of 120 with a 28% FDCA yield. With respect to claim 18, Miller et al. teaches wherein the reaction medium is substantially free from alcohols, the reaction medium containing less than 1 wt. % alcohols (claim 18). With respect to claim 20, it would have been obvious to use an ionic liquid with a melting point below 180C because the reaction conditions taught by Miller et al. require such a range. Accordingly, claims 1-11, 13-15 and 17-20 are obvious.
Claim(s) 12 and 16 is/are rejected under 35 U.S.C. 103 as being unpatentable over US 9,701,652 B2 to Miller et al. in view of WO 2017/083297 A1 to Guo.
Miller et al. teaches methods of forming FDCA compounds from hexose diacid compounds in the presence of an acid catalyst with an ionic liquid. See Example 1, Col. 7-14. Exemplary embodiments utilize mucic (galactaric) and saccharic (glucaric) acids as the hexose diacid compound; sulfuric acid as the acid catalyst; and 1-butyl-3-methylimidazolium sulfate as the ionic liquid. See Col, 7, lines 61-67; Col. 8, lines 2-4.
Miller et al. does not teach an embodiment wherein the ionic liquid comprises an anion moiety selected from halogen ions.
Miller et al. teaches that the ionic liquid can comprise a counter anion selected from the group consisting of, chloride, bromide, and iodide. This amounts to an art-recognized equivalence, and it would have therefore been obvious to substitute the sulfate taught in the exemplary embodiment with a halogen anion such as chloride, bromide and iodide. See MPEP 2144.06(II).
With respect to claims 12 and 16, Miller et al. does not teach the addition of a organic solvent such as sulfolane or a co-catalyst such as lithium bromide.
Guo teaches an analogous reaction to that instantly claimed for the production of FDCA from a dicarboxylic acid via acid catalysis. Sulfolane may act as both a solvent and a catalyst (Para. [00011]). Lithium Bromide may be added to promote FDCA production (Para. [00013]). A PHOSITA would have found it obvious to incorporate both into the reaction taught by Miller et al. in order to act as a co-solvent/catalyst and thereby promote FDCA production. Accordingly claims 12 and 16 are obvious.
Conclusion
Claims 1-20 are rejected.
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/JED A KUCHARCZK/ Examiner, Art Unit 1623
/CLINTON A BROOKS/ Supervisory Patent Examiner, Art Unit 1621
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