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 .
DETAILED ACTION
This Office action is responsive to Applicant's preliminary amendment, filed Feb. 27, 2024. As filed, claims 1, 4-11. Claims 2-3 are canceled.
Priority
This application filed 02/27/2024 is a National Stage entry of PCT/FI2022/050551, International Filing Date: 08/26/2022 claims foreign priority to 20215901, filed 08/27/2021.
Information Disclosure Statement
Applicants' information disclosure statements (IDS) filed on 5/20/2024 have been considered except where lined through. Please refer to Applicants' copy of the 1449 submitted herewith.
Claim Objections
Claims 1 and 6 are objected to because of the following informalities: the recitation “mol-%” appears to contain a superfluous punctuation.
The recitation “increasing the temperature” in claim 1 should be replaced with “increasing temperature” to address potential lack of antecedent bases issues.
Appropriate correction is required.
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 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 of this title, 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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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, 4-11 are rejected under 35 U.S.C. 103 as being unpatentable over Shin et al. Tetrahedron 73 (2017) 4758-4785 (cited by Applicants in IDS) and further in view of Giani et al. Computers and Chemical Engineering 29 (2005) 1661–1676 (cited in PTO-892 attached herewith).
The article by Shin teaches ovel recyclable Re-catalyzed deoxydehydration reaction (DODH) was developed with an ionic liquid (IL) as a reaction medium for an efficient synthesis of adipic acid from biomass galactaric acid. The reaction as depicted in Scheme 1 on page 4758 (reproduced below) shows carefully designed solubility of ILs allowed a homogeneous DODH reaction to produce muconate 3 in excellent yields. Use of the IL also enabled an efficient separation of the muconate (muconic ester) product 3- which corresponds to claimed product muconic acid and muconic ester from the reaction mixture by simple decantation. The recovered IL layer containing the expensive Re catalyst was reused up to four times, yielding muconate; the overall process for bio-based products would become much more cost-effective, eco-friendly, and industrially viable, which could be applied to various biomass conversions (abstract).
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Regarding claims 1, 4-7, 9, 10, 11 the article by Shin teaches on Table 3, page 4761 that the reaction is conducted in a pressure tube, under reduce pressure and under argon, for 12h at temperature ranging 120-200C, wherein the metal catalyst loading is 0.05 eq; the rhenium catalyst include ammonium perrhenate (entry 8 of Table 1) whil on experimental section, the general procedure illustrate reaction conducted under pressure in a pressure reactor, heating the reagents for 12h, cooling crude reaction mixture to room temperature, work-up to separate the product:
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The instant claims differ from the prior art in that the publication by Shin does not teach preparation of bio-based non-alcoholic solvent such as methyl acetate for the reaction of instant claims; the prior art by Shin teaches reduced pressure, it does not teach pressure of 5 bar.
Regarding the limitation of instant claims about the non-alcohol solvent, choosing an appropriate solvent for the reaction is routine in chemical art. The use of common organic solvents, are the known options within the technical grasp of one of ordinary skill in the art.
As discussed in the article by Giani selection of appropriate solvents for the promotion of organic reactions, by using a rules-based procedure where the estimated reaction-solvent properties and the solvent-environmental properties guide the decision-making process is known in the art. Disclosed on table 1 on page 1666 of the article by Giani is methyl acetate as alternative solvent to alcohol were found as more suitable solvents for reaction. A list of candidate solvents are generated through ProCamd program, providing a breakdown of number of feasible chemicals that have been found to satisfy the specified solvent property constraints. Based on the teaching of prior art combined with technical knowledge, a phosita would opt for alcohol as reaction solvent instead of water as disclosed by prior art by Shin, with reasonable expectation of success.
Regarding the limitation of instant claims about the pressure of at least 5 bar and reaction times, since the prior art teaches reaction under reduced pressure at various reaction times, and since pressure and reaction time are a result-effective variable in the reaction or producing muconic acid and esters, the skilled artisan would have been motivated to modify the reaction conditions such as pressure, reaction time, as part of routine optimization in attempting to obtain the highest product yield in the shortest amount of time. In other words, it is inherent that a person of ordinary skill in art would be motivated to optimize a reaction by varying experimental parameters in search of optimal conditions. See MPEP 2144.05 II.A:
“[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955) (Claimed process which was performed at a temperature between 40°C and 80°C and an acid concentration between 25% and 70% was held to be prima facie obvious over a reference process which differed from the claims only in that the reference process was performed at a temperature of 100°C and an acid concentration of 10%.); see also Peterson, 315 F.3d at 1330, 65 USPQ2d at 1382 (“The normal desire of scientists or artisans to improve upon what is already generally known provides the motivation to determine where in a disclosed set of percentage ranges is the optimum combination of percentages.”)
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention, to combine the teachings of the prior art and to produce muconic acid and muconic acid esters under optimal reaction conditions and solvents, to arrive at instant invention with reasonable expectation of success because the prior art teaches that bio-based products would become much more cost-effective, eco-friendly, and industrially viable and that optimizing the reaction conditions by choosing an appropriate solvent for the reaction is routine in chemical art.
"Exemplary rationales that may support a conclusion of obviousness include: (A) Combining prior art elements according to known methods to yield predictable results ". See MPEP § 2143.
Therefore, absent a showing of unexpected results, the instant claims are obvious over the prior art.
Conclusion
Claims 1, 4-11 are rejected.
Telephone Inquiry
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ANA MURESAN whose telephone number is (571)-270-7587. The examiner can normally be reached on Monday through Friday, 8:30 am to 5:30 pm EST.
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/ANA Z MURESAN/Primary Examiner, Art Unit 1692
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