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 .
Election/Restrictions
Applicant's election with traverse of group I invention (claims 1-13) in the reply filed on 12/10/2025 is acknowledged. The traversal is on the ground(s) that there is no undue burden for search and examination. This is not found persuasive because different groups of inventions involve different search queries, different class/subclass or CPC groups, prior art applicable to one invention not necessarily to another invention
The requirement is still deemed proper and is therefore made FINAL.
Claim 14 is withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim. Applicant timely traversed the restriction (election) requirement in the reply filed on 12/10/2025.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 8 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention. In this case, claim 8 recites “wherein rhenium comprises……”, but its parent claim 5 does not even require any rhenium, therefore, such limitation appears lack of antecedent basis. For examination on merit, given a rhenium component is recited for the first time in claim 7, the examiner interprets “rhenium” in claim 8 refers to “the rhenium component” in claim 7.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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.
Claims 1-9 and 11-13 are rejected under 35 U.S.C. 103 as obvious over Hocevar et al (EP3782976) in view of Deng et al. (Efficient Catalysts for the Green Synthesis of Adipic Acid from Biomass, Angew. Chem. Int. Ed. 2021, 60, 4712– 4719) and Radius (US2011/0008238).
Hocevar et al. teaches a process of producing adipic acid esters comprising (a) feeding an aldaric acid, specifically glucaric acid, an alcohol, specifically methanol ( i.e. a first solvent) and Re-catalyst on a solid support into a batch or continuous reactor; (b) heating the mixture of (a) at a temperature ranging from 80 - 250 °C, preferably 100 - 140 °C, for dehydroxylation to proceed, (c) separating the catalyst from the liquid phase, and (d) isolating adipic acid and/or their esters by evaporation of residual alcohol and aldehyde/ketone and volatile short chain aldol condensation products ( para. [0031]-[0032], example 1-6, Fig.1, claim 1). Hocevar et al. disclosed obtained adipic acid esters, compound (7) (Fig. 1, page 8, example 1-6) of hexanedioic acid dimethyl ester which has a generic formula of CH3OOC(CH2)4COOCH3, is a methyl adipate. Hocevar et al. further teaches the Re catalyst is a metal catalyst (para. [0046], claim 9-12) and such solid Re catalyst being separated from the liquid phase containing alkyl adipate via filtration (para. [0046]), then separated solid Re catalyst being washed with a second solvent (e.g. methanol), centrifuged to remove the second solvent, and being regenerated via reducing under 400 °C (i.e. calcination) for 3 hours (para. [0040]). Hocevar et al also teaches the catalyst can include a hydrogenation catalyst comprising Pd or Pt catalyst (claim 10-12, para. [0024]).
Regarding claim 1, Hocevar et al. does not teach the reaction solution comprising a glucaric acid potassium salt, or an acid catalyst, or obtaining adipic acid via hydrolyzing the alkyl adipate, or heating and drying the washed metal catalyst.
Deng teaches using glucaric acid with a base of KOH obtaining a glucaric acid potassium salt to contact with an activated carbon supported Pd and Re catalyst and an acid catalyst of Amberlyst-15 (scheme 1 b) to produce alkyl adipate, which is then hydrolyzed to produce adipic acid (page 4712 two last para.-page 4713 first two para., scheme 2, page 4713 last para.-page 4715 second para., table 1, table 3, page 4718 Conclusion section).
It would have been obvious for one of ordinary skill in the art to adopt such glucaric acid potassium salt as shown by Deng to modify the process of Hocevar et al. because by doing so can help remarkably increase glucaric acid formation (in the form of potassium glucarate) as suggested by Deng (Fig 1, scheme 2, page 4713 last para- 4714 2nd para.). It would have been obvious for one of ordinary skill in the art to add an acid catalyst into the reaction of glucaric acid solution because by doing so can help dissolve potassium glucarate by promoting its esterification with methanol as suggested by Deng (page 1474 left col. last para.). It would have been obvious for one of ordinary skill in the art to hydrolyzing the alkyl adipate to adipic acid as shown by Deng to modify the process of Hovevar et al. because by doing so can help using available biomass to obtain valuable adiptic acid for intended use, e.g. a key monomer for making nylon-66 as suggested by Deng (page 4712 Introduction section, scheme 1 b-page 4713 first para.).
Radius teaches a hydrogenation catalyst including Pt or Pd being supported onto support such as alumina, activated carbon can be thermally regenerated under temperature of 50 to 600 °C (para. [0025], [0029]-[0031], claim 7) after being separated with reaction solution, washed with water, e.g. filtered water, deionized water, heated and dried (para.[0018]-[0024, [0058], [0063], [0064]).
It would have been obvious for one of ordinary skill in the art to adopt such well-known heating and drying after washing as shown by Radius to modify the metal catalyst regeneration process of Hocevar et al. because adopting such well-known technique of heating and drying to modify a well-known metal catalyst regeneration for improvement would have predictable results (see MPEP §2143 KSR).
Regarding claim 2, as for the claimed “glucaric acid potassium salt being obtained by …… and potassium hydroxide”, such limitation is a product by process limitation, even though product-by-process limitations are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process (See § MPEP 2113). In this case, Hocevar et al. already teaches a same or substantially the same glucaric acid potassium salt as that of instantly claimed.
Regarding claim 3-7, such limitations are met as discussed above.
Regarding claim 8, Hocevar et al. teaches the rhenium catalyst can comprise rhenium oxide with different oxidation state of Re, e.g. RexOy (para. [0022]).
Regarding claim 9, Hocevar et al. further teaches the amount of Re being presented on the support ranging from 1 to 20 wt.% relative to the support, while the Pd or Pt in the range of 0.1-5 wt.% corresponding to the support (para. [0024]), wherein such teachings suggest an overlapped amount of the support and an overlapped amount of the metal components as those of claimed respectively, thus render a prima facie case of obviousness (see MPEP §2144. 05 I).
Regarding claim 11, Radius does not require mixing the metal (hydrogenation ) catalyst with water needed heating, therefore, mixing them under ambient atmosphere, i.e. at temperature of 15-25 °C is expected. Radius does not expressly teach the heating and drying temperature, but discloses the offgas from the apparatus of heating and drying the catalyst being less than 100 °C (para. [0022], [0023]). It would have been obvious for one of ordinary skill in the art to heat the water washed metal catalyst under temperature less than 100 °C as suggested by Radius for help obtaining desired metal catalyst because such temperature can help removing water and can also produce an offgas stream with temperature being lower than 100°C. It would have been obvious for one of ordinary skill in the art to adopt same heating hours as that of instantly claimed via routine experimentation (see MPEP §2144. 05 II) for help removing as much as water from the washed metal catalyst. As for the claimed drying temperature and hours, it would have been obvious for one of ordinary skill in the art to dry such heated metal catalyst around or slight above water boiling temperature (a littler higher than 100 °C) with same drying time as that of instantly claimed via routine experimentation (see MPEP §2144. 05 II) for obtaining a dried metal catalyst with minimum moisture.
Regarding claim 12, Radius already teaches washing water can be highly purified water, such as filtered or deionized water. It would have been obvious for one of ordinary skill in the art to adopt distilled water as purified water to wash the separated metal catalyst for help removing undesired byproduct and intermediate thus obtaining a cleaned metal catalyst for regeneration because distilled water is commercially available and easy to obtain.
Regarding claim 13, Hocevar et al. already teaches heating under 400 °C for 3 hours, but does not teach the atmosphere being nitrogen. Radius further teaches thermal regeneration can be performed at temperatures which are generally in the range from 50 to 600 °C, preferably from 100 to 450 °C, and preferably under an inert gas atmosphere, such as argon or nitrogen (para. [0007]-[0008]). It would have been obvious for one of ordinary skill in the art to adopt such well-known inert gas atmosphere of nitrogen as shown by Radius to modify the regeneration heating/calcining of Hocevar et al. because adopting such well-known technique of nitrogen as inert atmosphere to modify a well-known metal catalyst regeneration process for improvement would have predictable results (see MPEP §2143 KSR).
Allowable Subject Matter
Claim 10 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JUN LI whose telephone number is (571)270-5858. The examiner can normally be reached IFP.
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/JUN LI/ Primary Examiner, Art Unit 1732