Prosecution Insights
Last updated: April 19, 2026
Application No. 18/257,654

LIQUID-PHASE OXIDATION OF METHACROLEIN WITH GOLD BASED CATALYSTS

Non-Final OA §103§DP
Filed
Jun 15, 2023
Examiner
MURESAN, ANA Z
Art Unit
1692
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Rohm And Haas Company
OA Round
1 (Non-Final)
76%
Grant Probability
Favorable
1-2
OA Rounds
2y 4m
To Grant
99%
With Interview

Examiner Intelligence

Grants 76% — above average
76%
Career Allow Rate
530 granted / 702 resolved
+15.5% vs TC avg
Strong +30% interview lift
Without
With
+30.3%
Interview Lift
resolved cases with interview
Typical timeline
2y 4m
Avg Prosecution
38 currently pending
Career history
740
Total Applications
across all art units

Statute-Specific Performance

§101
0.4%
-39.6% vs TC avg
§103
39.6%
-0.4% vs TC avg
§102
20.1%
-19.9% vs TC avg
§112
26.3%
-13.7% vs TC avg
Black line = Tech Center average estimate • Based on career data from 702 resolved cases

Office Action

§103 §DP
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 15 June, 20 23 . As filed, Claims 1- 14 are pending. Priority This application, filed 06/15/2023 is a National Stage entry of PCT/US2021/061513 , International Filing Date: 12/02/2021 PCT/US2021/061513 is a Continuation of 63127643 , filed 12/18/2020 . Information Disclosure Statement Applicants' information disclosure statements (IDS) filed on 6/15/2023 and 9/23/2023 have been considered except where lined through. Please refer to Applicants' copy of the 1449 submitted herewith. Claim Objections Claim 1 is objected for reciting improper Markush language: the recitation in claim 1 “selected from” should be changed to “selected from the group consisting of”. See MPEP 803.02. 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. 1. Claims 1-1 3 are rejected under 35 U.S.C. 103 as being unpatentable over US 2015/0321178 by Suzuki et al ( “the ‘178 publication”; cited by Applicants in IDS ) . The c laimed invention is directed to a method for preparing methacrylic acid from methacrolein comprising: contacting a liquid mixture comprising methacrolein and water in the presence of oxygen with a heterogeneous catalyst comprising a support and gold; wherein the support comprises an oxide selected from y -, β -, or δ -alumina, magnesia, titania, zirconia, hafnia, vanadia, niobium oxide, tantalum oxide, ceria, yttria, lanthanum oxide, zinc oxide or a combination thereof . Determining the scope and contents of the prior art The ‘178 publication teaches a method for producing Methacrylic acid was produced from methacrolein and water in liquid phase – water and acetonitrile solvent, by using the noble metal-supported material specifically AuNi/SiAl- Ni-Mg composite oxide as shown in e xample s 18 -24 . T he methacrylic acid selectivity was 94.9% [0286]-[0303] ; ( instant claims 1- 5 , 8, 12 ). Regarding instant claim s 2-3 , the ‘178 publication teaches in example 18 the amount of water of about 60% of total wt % liquid mixture. Regarding instant claim s 4-8, the ‘178 publication teaches as suitable solvent ketones, nitriles, alcohols, organic esters, hydrocarbons, organic acids and amides including acetone, N,N-dimethylformamide, etc . [0158] . Regarding instant claim s 9-11 , the ‘178 publication teaches the on [0119] that the noble metal particles are preferably supported on a support in a highly dispersed state. Specifically, the noble metal particles are supported n a state where the particles do not overlap one another in a stacking direction on the support, and are supported to be dispersed more preferably in a particulate state - where the particles are not in contact with one another - or in a thin film state - where the particles do not overlap one another in the stacking direction on the support although they are in contact with one another. The noble metal particles have an average particle size ranging from 2 to 10 nm . Example 15 on [0259]-[0266] of the cited reference describes a noble metal-supported material supporting 2.0% by mass of Au a 2%Au/Si-Al-Ni-Mg composite oxide ; the specific surface area measured by the nitrogen adsorption method was 242 m2/g, the pore volume was 0.27 mL/g and the average pore size was 3.9 nm. The average particle size was found to be 62 μm by laser scattering particle size distribution measurement. Th e noble metal-supported material was found to be free from break or crack and be in a substantially spherical shape on the basis of observation with a scanning electron microscope . Regarding instant claim s 12- 13, the ‘178 publication teaches on [1021] titanium as the component of composite oxide of the noble-metal supported material. Ascertaining the differences between the prior art and the claims at issue The difference between the prior art and the instant is that the prior art is that the catalyst for the synthesizing methacrylic acid which catalyst comprises gold on support comprises silica and nickel as additional components . However, it is noted that applicant(s) "comprising" terminology regarding the catalyst components is open language and does not exclude those additional elements disclosed therein- i.e. silica and nickel as additional catalyst components. It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention was made, to use the method on producing methacrylic acid by reacting methacrolein with oxygen in liquid phase under gold-containing catalyst composition on support such as alumina or titania as taught by the ‘ 178 publication , because the prior art specifically teach catalyst comprising gold and support composition which encompasses instantly claimed catalyst composition as effective for methacrylic acid production of the prior art. One of ordinary skill in the art would have a reasonable expectation of success to arrive at the instantly claimed process because the prior art teach that the oxidation of methacrolein to methacrylic acid when mediated by catalyst comprising gold on support such as titania, alumina increased methacrylic acid selectivity . The rationale to support a conclusion that the claim would have been obvious is that teaching, suggestion, or motivation in the prior art that would have led one of ordinary skill to modify the prior art reference or to combine prior art reference teachings to arrive at the claimed invention. KSR, 550 U.S. at_, 82 USPQ2d at 1395. Th erefore , the claimed invention as a whole is prima facie obvious over the teachings of the prior art. 2. Claims 1- 8, 12- 14 are rejected under 35 U.S.C. 103 as being unpatentable over JP2005-22069 , 2005 (“the ‘069 publication”; cited by Applicants in IDS). Determining the scope and contents of the prior art The ‘069 publication teaches a method for producing an alpha-beta -unsaturated carboxylic acid by oxidizing an alpha-beta -unsaturated aldehyde with molecular oxygen in a liquid phase , containing organic solvent comprising water and any organic solvent , using a noble metal catalyst such as gold supported on a carrier such as activated carbon, carbon black, silica, alumina, magnesia, titania, and zirconia ; e xamples of the unsaturated aldehyde raw material include methacrolein ; example an alpha-beta -unsaturated carboxylic acid - methacrylic acid ( abstract; [0007] ; [0015] ; [0021]; [0033]; [0042] ; instant claim 1) Regarding instant claim 2-3, the ‘069 publication teaches various composition of the mixed solvent at this time was acetic acid 0.40, water 0.10, and acetone 0.50 in molar ratio [0033] ; acetic acid 0.32, water 0.39, and acetone 0.29 in molar ratio on [0035 ]. Regarding instant claim s 4-8, the ‘069 publication teaches as suitable solvent s such as acetone [0 010 ] . Regarding instant claim s 12- 1 4 , the ‘178 publication teaches titani a as the carrier material ; The loading rate of the noble metal in the supported catalyst is usually 0.1 mass% or more, and particularly preferably 15 mass% or less [0021]. Ascertaining the differences between the prior art and the claims at issue The difference between the prior art and the instant is that the prior art does not teach preparative example of synthesizing methacrylic acid by reaction of methacrolein and water with oxygen in which the catalyst comprises gold as noble metal component of the catalyst. However, the ‘069 publication specifically teaches gold as suitable metal as catalyst component on [0015] and the catalyst carrier include alumina, magnesia , titania, and zirconia and further that the supported catalyst can be produced in the same manner as discussed in the provided examples [0021]. A prima facie case of obviousness based on structure exists if the prior art suggests to one of ordinary skill in the art to make the substitution or modification. In re Tabor , 502 F.2d 775 (CCPA 1974). It has been held several times that structurally similar compounds are obvious over one another. See, e.g., In re Payne , 606 F.2d 303, (CCPA 1979) (An obviousness rejection based on similarity in chemical structure and function entails motivation of one skilled in the art to make the claimed compound with an expectation that compounds similar in structure will have similar properties. When prior art compounds essentially "bracket" the instantly claimed compound, one of ordinary skill in the art would clearly be motivated to make the claimed compound.). I n the insta nt case, it would therefore have been obvious to one of ordinary skilled in the art before the effective filing date of the claimed invention to utilize gold as metal component and alumina, magnesia , titania, and zirconia as support , and have reasonable expectation of success in arriving at the claimed invention, because the prior art specifically suggest gold on support such as titania are suitable option for the liquid-phase oxidation reaction to produce the same compound as claimed by same starting material s and reagents and same process steps. MPEP 2141 provides that exemplary rationales that may support a conclusion of obviousness include (E) " Obvious to try" - choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success. Thus, the claimed invention as a whole is prima facie obvious over the teachings of the prior art. Double Patenting The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg , 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman , 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi , 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum , 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel , 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington , 418 F.2d 528, 163 USPQ 644 (CCPA 1969). A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA. A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b). The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13. The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA/25, or PTO/AIA/26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer . Claims 1-14 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-14 of copending Application No. 18257644 in view of JP2005-22069 , 2005 (“the ‘069 publication”; cited by Applicants in IDS). Although the claims at issue are not identical, they are not patentably distinct from each other because both claim a process for preparing (meth)acrylic acid by the same steps: contacting a liquid mixture comprising ( meth ) acrolein and water in the presence of oxygen with a heterogeneous catalyst comprising a support and gold; wherein the support comprises an oxide selected from y-, 8-, or 8-alumina, magnesia, titania, zirconia, hafnia, vanadia, niobium oxide, tantalum oxide, ceria, yttria, lanthanum oxide, zinc oxide or a combination thereof . While the copending application ‘644 teaches oxidation of acrolein instead of methacrolein under the same process steps and catalyst to corresponding acrylic acid – instead of methacrylic acid, as discussed in the prior art the general synthetic methodology for oxidation of unsaturated aldehydes to corresponding acid is applicable for both substrates- acrolein or methacrolein given the similar reactivity. In this regards, the prior art by the ‘069 publication teaches that the method for producing an alpha-beta -unsaturated carboxylic acid by oxidizing an alpha-beta -unsaturated aldehyde with molecular oxygen in a liquid phase , containing organic solvent comprising water using a noble metal catalyst such as gold supported on a carrier such as alumina, magnesia, titania, and zirconia wherein the unsaturated aldehyde raw material include acrolein, methacrolein ; ( abstract; [0007]; [0015]; [0021]; [0033]; [0042] . The prior art as taught by copending Application No. 18257644 and the ‘069 publication teach the same general process for the production of unsaturated carboxylic acid , and copending Application No. 18257644 and the ‘069 publication reside in the closely overlapping technical area of processes related to production method for producing an alpha-beta -unsaturated carboxylic acid by oxidizing an alpha-beta -unsaturated aldehyde substrate with oxygen in a liquid phase , mediated by gold supported on a carrier catalyst. This is a provisional nonstatutory double patenting rejection. Conclusion Claims 1- 14 are rejected. Telephone Inquiry Any inquiry concerning this communication or earlier communications from the examiner should be directed to: Ana Muresan (571) 270-7587 (phone) (571)270-8587 (fax) Ana.Muresan@uspto.gov The examiner can normally be reached Monday - Friday (9:00AM - 5:30PM). Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. 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. Information regarding the status of an application may be obtained from the Patent Application Information Retrieval (PAIR) system. Status information for published applications may be obtained from either Private PAIR or Public PAIR. Status information for unpublished applications is available through Private PAIR only. For more information about the PAIR system, see https://ppair-my.uspto.gov/pair/PrivatePair. Should you have questions on access to the Private PAIR system, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative or access to the automated information system, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /ANA Z MURESAN/ Primary Examiner, Art Unit 1692
Read full office action

Prosecution Timeline

Jun 15, 2023
Application Filed
Dec 12, 2025
Non-Final Rejection — §103, §DP (current)

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Study what changed to get past this examiner. Based on 5 most recent grants.

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Prosecution Projections

1-2
Expected OA Rounds
76%
Grant Probability
99%
With Interview (+30.3%)
2y 4m
Median Time to Grant
Low
PTA Risk
Based on 702 resolved cases by this examiner. Grant probability derived from career allow rate.

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