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 amendments filed May 12, 2025. As filed, claims 1-13 are pending.
Priority
This application, filed 03/25/2024 is a National Stage entry of PCT/US2022/045719 , International Filing Date: 10/05/2022; PCT/US2022/045719 is a Continuation of 63253558 , filed 10/08/2021.
Information Disclosure Statement
Applicants' information disclosure statements (IDS) have been considered except where lined through. Please refer to Applicants' copy of the 1449 submitted herewith.
Claim Objections
Claims 5-13 are objected to because of the following informalities: replace capitalized “Claim” with lower case.
Appropriate correction is required.
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.
Claims 2-10, 12 are 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.
Regarding claim 2, the terminology "etc." renders said claim and its dependents indefinite because it is unclear whether the limitation(s) following the phrase are part of the claimed invention.
Regarding claim 12, the recitation ”wherein an average concentration of methanol in the reactor system is greater than 70 wt% based on the total weight of methanol and methacrolein in the reaction mixture introduced to the reactor system” followed by recitation ” wherein the concentration of methanol is the average of the concentration of methanol in the reaction mixture introduced to the reactor system and the concentration of methanol in the product stream exiting the reactor system” renders said claim indefinite because it is unclear whether the limitation(s) following the phrase are part of the claimed invention.
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 1-13 are rejected under 35 U.S.C. 103 as being unpatentable over EP 3786148, March 3, 2021 by Darmnstand et al. (cited by Applicant in IDS; machine translation provided herewith).
Instant claims are drawn to a method for the production of methyl methacrylate (MMA) via oxidative esterification in a reactor system comprising:introducing a reaction mixture comprising methacrolein, methanol, and an oxygen-containing gas to the reactor system comprising a noble metal-containing
catalyst, wherein a methanol concentration of the reaction mixture entering the reactor is greater than 32 wt% based on the total weight of methanol and methacrolein
entering the reactor system; wherein the methanol concentration in the product stream exiting the reactor system is at least 65 wt% based on the total weight of the methanol and methacrolein exiting the reactor system;
wherein the product stream exiting the reactor system comprises greater than 0.1 ppm and less than 5000 ppm methyl isobutyrate.
The ‘148 publication teaches a process for the production of methyl methacrylate by oxidative esterification in a reactor system from methacrolein, methanol and oxygen and using a noble metal-containing catalyst. The process of the prior art for the production of alkyl methacrylates, in which methacrolein is conducted in a first reaction stage in a reactor I and this is oxidatively esterified in a second reaction stage in a reactor II with an alcohol in the liquid phase to give an alkyl methacrylate; the reactor discharge from reactor II is separated into a first aqueous phase, containing more than 80% by weight of the alcohol present in the reactor discharge and a second phase, each containing more than 80% by weight of the alkyl methacrylate and methacrolein (MAL) present in the reactor discharge, and in a subsequent single- or multi-stage distillation the second phase is worked up in such a way that methacrolein is separated from alkyl methacrylate (see claims 1 and 3 of the cited reference; examples; instant claims 1-3). Disclosed on example 2 of the ‘148 publication is the outline of the direct oxidative esterification of methacrolein to methyl methacrylate (MMA) with a nanoparticulate gold-containing DOE catalyst (instant claims 6, 7; page 15-12 of the translation). The ‘148 publication teaches on example 2 page 18 of translation the methyl isobutyrate content in the product stream is less than 1000ppm (instant claim 1, 13). The starting feed composition was 3% by weight of MAS (50% of which are in the form of sodium salt at pH 7), 35% by weight of MMA, 5% by weight of water (total of 43%), the remainder being methanol – therefore the methanol content in the feed stream is 57wt% based on the total weight of methanol and methacrolein which reads on greater than 35%methnaol of the reaction mixture entering the reactor of claimed process. The methanol content in the product stream is 46.3wt% to 58wt% based on the total weigh of the methanol and methacrolein (page 18 of translation).
The ‘148 publication teaches that the process is characterized in that the reactor discharge from reactor II is first divided into a first phase, containing more than 80% by weight of the alcohol present in the reactor discharge and a second phase, each containing more than 90% by weight of the alkyl methacrylate present in the reactor discharge and methacrolein (MAL) is separated; this second phase is then only separated into a third phase, containing high-boiling components and a fourth phase, each containing more than 90% by weight of the alkyl methacrylate and methacrolein (MAL) present in the reactor discharge; the fourth phase is then separated from the major part of the alkyl methacrylate from the major part of the MAL in a distillation column (page 9).
The method of prior art produces MMA in high a yield as possible; highest possible degree of recycling of the unreacted methacrolein and alcohol (methanol), the lowest content or, compared to the prior art, a reduced content of alkyl isobutyrate, in particular methyl isobutyrate; the lowest water and energy consumption, as well as clean disposal flows and exhaust gases (page 8).
Regarding instant claims 8-10, it would have been obvious to a phosita to operate the process in a single or multiple reactors or continuous or batch mode and have reasonable expectation of success in producing claimed compound. See also MPEP 2144.04: “In re Dilnot, 319 F.2d 188, 138 USPQ 248 (CCPA 1963) (Claim directed to a method of producing a cementitious structure wherein a stable air foam is introduced into a slurry of cementitious material differed from the prior art only in requiring the addition of the foam to be continuous. The court held the claimed continuous operation would have been obvious in light of the batch process of the prior art.)”
The method of the present application differs from the method described in the ‘148 publication in that prior art teach methanol content in the product stream is 46.3wt% to 58wt% while instant claims require methanol concentration in the product stream exiting the reactor system is at least 65 wt% based on the total weight of the methanol and methacrolein exiting the reactor system for the formation of the same product by the same reaction – oxidative esterification of methanol with methacrolein.
Regarding the concentration of methanol content in the product stream, the ‘148 publication teaches the same methodology- oxidative esterification of methacrolein with to produce MMA and low content of byproducts, by same process steps, and specifically teaches that methanol concentration in the product stream is 46.3wt% to 58wt%. Additionally, the reference teach that the purification method may comprise an additional final step for adjusting the methanol content of the product solution. The methanol concentration adjustment may be realized by, for example, by adding more
in methanol to the feed solution which would results in concentrating the solution exiting the reactor, by any commonly known method readily available for the person of ordinary skills in the art.
Therefore, the determination of the appropriate concentration of methanol as an art recognized result-effective variables, is subject to routine optimization in the course of modification of the process of the ‘148 publication.
Furthermore, pertaining to the concentration of a process, it is noted that generally, differences such parameters will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such parameter is critical. “[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) See MPEP 2144.5.
The instantly claimed process therefore corresponds to the combination of prior art elements according to known methods to yield predictable results.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention, to adjust the concentration of methanol reasonable expectation for success since each element retains its intended function in the combination.
Absent factual unexpected, unobvious, and beneficial results, the claimed invention would have been suggested to one skilled in the art and therefore, the instant claimed invention would have been obvious to one skilled in the art.
Conclusion
Claims 1-13 are rejected.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the
examiner should be directed to:
Ana Muresan
(571) 270-7587
Ana.Muresan@uspto.gov
The examiner can normally be reached Monday - Friday (9:00AM - 5:30PM).
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at 571-270-5241.
The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/ANA Z MURESAN/Primary Examiner, Art Unit 1692
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