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 December 23, 2024. As filed, claims 1-11 are pending.
Priority
This application, filed 3/26/2024 is a National Stage entry of PCT/US2022/045724 , International Filing Date: 10/05/2022; PCT/US2022/045724 is a Continuation of 63253561 , 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 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 1-11 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 process for the production of methyl methacrylate (MMA) via oxidative esterification comprising:
a) producing methacrolein from propionaldehyde and formaldehyde;
b) reacting the methacrolein in an oxidative esterification reaction to obtain methyl
methacrylate; wherein:
reacting the methacrolein in an oxidative esterification reaction comprises introducing a
reaction mixture comprising the methacrolein, methanol, and an oxygen-containing gas to a reactor system comprising a heterogeneous noble metal-containing catalyst;
a liquid phase stream exiting the reactor system contains at least 30 wt% methanol based on the total weight of the liquid phase stream;
the liquid phase stream exiting the reactor system contains less than 30 wt% methacrolein based on the total weight of the liquid phase stream;
the liquid phase stream exiting the reactor system comprises greater than 0.1 ppm and less than 5000 ppm methyl isobutyrate; and a gas phase stream exiting the reactor system comprises between 1 mol% and 7.5 mol% oxygen based on the total amount of the gas phase stream.
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 wherein methacrolein is produced by reacting propionaldehyde is reacted with formalin (formaldehyde) at temperatures of 162 to 205 ° C and a residence time of 6 seconds – which corresponds to step a) of the claimed process (page 5, example 1.22 on page 14 of translation). The process 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 methanol in the liquid phase to give an methyl methacrylate; the reactor discharge from reactor 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 such that methacrolein is separated from alkyl methacrylate which corresponds to step b) of the claimed process (see claims 1 and 3 of the cited reference; examples; instant claim 1).
Regarding the limitation of claim 1 “a gas phase stream exiting the reactor system comprises between 1 mol% and 7.5 mol% oxygen based on the total amount of the gas phase stream”, the prior art teaches the amount of air is increased in the steps until the exhaust gas has an oxygen concentration of 4% by volume (which corresponds to 4 mol% within the claimed range (page 16 of translation).
Regarding instant claims 2-4, disclosed on example 2 of the ‘148 publication is the direct oxidative esterification of methacrolein to methyl methacrylate (MMA) with a nanoparticulate gold-containing DOE catalyst. The reactor is filled with 15 kg of catalyst, the slurry density is thus 10-11% by weight based on the amount of catalyst used and the working volume of the reaction solution. The reaction mixture is heated to 80 ° C. The reactor is set to a working pressure of 5 bar absolute (with nitrogen as the starting medium). After the reaction temperature has been reached, air is fed in in steps of 1 kg / h and the reaction starts immediately, recognizable by the drop in the methacrolein level in the reactor or the increase in the MMA concentration in the reaction mixture (page 15-16 of the translation).
Regarding instant claim 5, the prior art teaches under 8% by volume of O 2 (page 16).
The reference teaches that 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 . The methanol content in the product stream is 46.3wt% to 58wt% based on the total weigh of the methanol and methacrolein which meet the limitation of at least 30wt% methanol in the stream exiting the reactor. The composition after 24 hours is: MMA: 32.4 wt% MeOH: 46.3 wt% Methacrolein: 9.4 wt% (which meets the limitation of less than 30wt% methacrolein in the stream exiting the reactor ); Methoxyisobutyric acid methyl ester (MIBME): 0.7 wt% Methacrylic acid (also Na-MAS): 0.8 wt% Water: 7.7 wt% Exhaust gas quantities and composition of the exhaust gas (11) as well as the feed composition (fresh feed and recycling streams) are also shown in Figure 4 shown in detail.
Other existing components are acetals of methacrolein (MAL-ACET) with a concentration of about 400 ppm, as well as isobutyric acid methyl ester (IBSME), the formal hydrogenation product of MMA also in a concentration of less than 1000 ppm in the degassed product mixture, as well as dimers of methacrolein and their derivatives .
(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, i.e. methyl isobutyrate; the lowest water and energy consumption, as well as clean disposal flows and exhaust gases (page 8).
Regarding instant claim 8, the ‘148 publication teaches catalyst as slurry (page 16).
Regarding instant claims 9-11, it would have been obvious to a phosita to operate the process in a single or multiple reactors 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 does not specifically teach less 30% methacrolein exiting the reactor system – instead it teaches 46.3 wt% methacrolein -for the formation of the same product by the same reaction – oxidative esterification of methanol with methacrolein.
Regarding the concentration of methacrolein 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 concentration of methacrolein in the product stream is 46.3wt%. Additionally, the reference teaches that the purification method may comprise an additional final step for adjusting the content of the product solution.
Therefore, the determination of the appropriate concentration of mthacrolein 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.
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 1-11 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
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/ANA Z MURESAN/Primary Examiner, Art Unit 1692
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