Prosecution Insights
Last updated: April 19, 2026
Application No. 18/249,917

IMPROVED PROCESS FOR PREPARING METHYL METHACRYLATE AND/OR METHACRYLIC ACID BY REDUCED BACK MIXING DURING CONVERSION

Non-Final OA §112
Filed
Apr 20, 2023
Examiner
BONAPARTE, AMY C
Art Unit
1692
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Röhm GmbH
OA Round
1 (Non-Final)
80%
Grant Probability
Favorable
1-2
OA Rounds
2y 2m
To Grant
99%
With Interview

Examiner Intelligence

Grants 80% — above average
80%
Career Allow Rate
584 granted / 734 resolved
+19.6% vs TC avg
Strong +24% interview lift
Without
With
+23.8%
Interview Lift
resolved cases with interview
Typical timeline
2y 2m
Avg Prosecution
40 currently pending
Career history
774
Total Applications
across all art units

Statute-Specific Performance

§101
1.6%
-38.4% vs TC avg
§103
33.3%
-6.7% vs TC avg
§102
15.7%
-24.3% vs TC avg
§112
32.8%
-7.2% vs TC avg
Black line = Tech Center average estimate • Based on career data from 734 resolved cases

Office Action

§112
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 . Claim Status Claims 1-17 were filed 4/20/2023. In a preliminary amendment filed on the same day, claims 1-17 were canceled and claims 18-33 were newly added. Claims 18-33 are currently pending. Priority The instant application was filed 4/20/2023 and claims the benefit of priority to: PNG media_image1.png 154 1010 media_image1.png Greyscale See filing receipt dated 9/5/2023. Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55. Drawings The drawings are objected to because the drawings are blurry and the labels are difficult to read. Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance. Additionally, Figure 3 should be designated by a legend such as --Prior Art-- because only that which is old is illustrated. See MPEP § 608.02(g) and p. 35 of the specification as filed. Corrected drawings in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. The replacement sheet(s) should be labeled “Replacement Sheet” in the page header (as per 37 CFR 1.84(c)) so as not to obstruct any portion of the drawing figures. If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance. Claim Rejections - 35 USC § 112(b) 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 26 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. Claim 26 recites “the process according to claim 18, wherein at least 60% of static dwell time of at least one second reaction stage is implemented in a dwell segment executed as a pipeline”. Claim 18 requires at least one reactor II comprises at least “one delay segment”. It is not clear if the newly introduced “dwell segment” of claim 24 is the same as the “delay segment” or another required part of the process apparatus. Claim Rejections - 35 USC § 112(d) The following is a quotation of 35 U.S.C. 112(d): (d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers. The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph: Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers. Claim 25 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 25 recites: “the process according to claim 24, wherein at least two reactors I are used for the first reaction stage and the further first reaction stage, wherein at least one reactor II comprising at least one preheater segment and/or delay segment is arranged between the at least two reactors I, and at least one reactor II comprising at least one preheater segment and/or delay segment is arranged at an exit from the first reaction stage”. In claim 24, from which claim 25 depends, the “at least two reactors II” are implemented by at least one shell-and-tube heat exchanger as a preheater segment, combined with at least one delay zone as a delay segment”. Therefore, claim 25 appears to be broader than claim 24 because both “reactor II”s are only required to have a preheater segment or a delay segment. This rejection would be overcome by deleing the limitation “and/or” and replacing it with –and--. Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements. Allowable Subject Matter Claims 18-24 and 27-33 are allowed. The following is a statement of reasons for the indication of allowable subject matter. The closest prior art to the claimed inventions are: Bernardin (WO 2015/055844, published 4/23/2015, of record in the IDS filed on 4/20/2023); and Benderly (EP0999200A1, published on 5/10/2000, of record in the IDS Filed on 4/20/2023). Bernardin is directed toward a hydrolysis vessel used during an amidification step of acetone cyanohydrin (ACH), in the industrial process for production of methyl methacrylate (MMA) or methacrylic acid (MAA). The hydrolysis vessel (200) is used for hydrolyzing acetone cyanohydrin with sulfuric acid to produce a mixture comprising α-sulfatoisobutyramide (SIBAM). It comprises at least one cooling system (212; 244) on its internal annular periphery area and it is divided into at least two stages, preferably three, along its vertical wall, each stage (S1 to S3) comprising a ACH feeding inlet (201, 202, 203). Such vessel allows controlling both homogeneity and temperature of the mixture, and thus obtaining a high yield for the hydrolyzing reaction in very safe conditions. See abstract. The process is summarized in Fig. 1: PNG media_image2.png 720 1152 media_image2.png Greyscale In unit 110, HCN is produced by the Andrussow process and in unit 120 acetone cyanohydrin (ACH) is prepared. See [0024-0027]. The amidification of acetone cyanohydrin occurs in unit 130 and corresponds to instant steps a (first reaction stage) and b (second reaction stage). See [0028-0038]. In S4 (first reaction stage), instant step a is performed at a temperature between 80-110°C in hydrolysis unit 131 (Fig. 2) with sulfuric acid (H2SO4) having a concentration higher than 98 wt%, preferably between 99.5 wt% and 100 wt%. In S5 (second reaction stage), instant step b is performed at a temperature in the range of 110-165°C to produce a mixture comprising 2-methylacrylamide (MACRYDE) and sulfuric acid in thermal conversion unit 133 (Fig. 2). Also see [0044-0047 and 0067]. The MACRYDE mixture from step S5 can be fed to either a hydrolysis unit in S7 and treated with water (H2O) to produce methacrylic acid (MAA) and/or an esterification unit in S6 and treated with methanol (CH3OH) to produce methyl methacrylate (MMA) as required in instant step c (third reaction stage). See [0041-0043]. Bernardin further teaches a hydrolysis vessel (200) in Fig. 3-6 for step S4, which is designed to control homogeneity and temperature using a specific cooling system. See abstract, Fig. 3-6, and [0048-0065]. Further regarding instant limitation (ii), Bernardin teaches that the thermal conversion stage (S5), corresponding to instant step b/second reaction stage, is carried out for a “predetermined retention time”, wherein the mixture is maintained in the confined vessel at the conversion temperature during the predetermined retention time to have an optimal yield of conversion. See [0044]. Thus the “dwell”/retention time in the second reaction stage is variable and can be determined based on the temperature employed. Bernardin does not explicitly teach or suggest: (iii) that step S5 (instant step b/second reaction stage) is carried out in a reactor comprising at least one pre-heating segment comprising one or more linear pipeline elements that are heated by a heating medium spatially separate from the reaction mixture which heats the first reaction mixture by 10 to 100°C; (iv) that the reactor for the second reaction stage comprises at least one delay segment which is operated under virtually adiabatic conditions (defined on p. 17, lines 28-30 of the specification as filed); (v) that the at least one preheater segment and/or the at least one delay segment are implemented in a combination of linear pipeline elements and deflections, wherein the linear pipeline elements are connected to one another via reducing flanges; and Wherein a superficial velocity of the linear pipeline elements relative to a superficial volume of the deflections in the at least one preheater segment corresponds to a ratio in the range from 2.0 to 75.0. Benderly is directed toward a thermal conversion apparatus useful for producing methacrylic acid or methyl methacrylate (using the same process as that of Bernardin) that comprises at least one pipe means for maintaining plug flow. See abstract and claim 1. Benderly teaches that the thermal conversion apparatus is of Fig. 2: PNG media_image3.png 752 810 media_image3.png Greyscale . The thermal conversion apparatus comprises three sections: i) a pre-heater (bottom, see “inlet”, preferably a heat-exchanger); ii) a thermal conversion section (9, 7, 8, and 10); and iii) a cooler (top, see “output”). See [0015-0022]. The pre-heater and thermal conversion section (adiabatic) delay segment) are show to have U-shaped 180° deflections. However, Benderly does not explicitly teach that the linear pipeline elements and the deflections are connected to one another via reducing flanges (defined in instant Fig. 4 and p. 16, lines 11-13 of the specification as filed) or that the superficial volume of the linear pipeline elements relative to a superficial volume of the deflections in the at least one preheater segment corresponds to a ratio in the range from 2.0 to 75.0. Therefore, the combination of Benderly and Bernardin appears to meet all of the limitations of independent claims 1 and 29 except for the reducing flange connections and superficial volume ratio. However, it would not have been obvious to modify the combined process of Benderly and Bernardin to arrive at that claimed because the Applicant shows evidence of unexpected results tied to the reducing flange connections and superficial volume ratio in Table 7 on p. 46-47 of the specification as filed. Examples 1’ and 2’ are comparative examples which correspond to the Benderly apparatus, shown in instant Fig. 3 and discussed as “EP 0 999 200” on p. 4 and 18 of the specification as filed. Examples 3-6 are inventive and correspond to the connections of Fig. 4. Also see Fig. 5a (comparative) vs. Fig. 5b (inventive). The results show that when the superficial volume is held within the claimed ratio, even with all other variables optimized, that the yield of the MAA and MA is significantly increased, especially for an industrial process which produces large quantities of MAA and MA. Therefore, the instantly claimed inventions appear to be free from the prior art. Conclusion Claims 18-24 and 27-33 are allowed. Claims 25 and 26 are rejected under 35 USC 11, but otherwise appear to be free from the prior art. Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMY C BONAPARTE whose telephone number is (571)272-7307. The examiner can normally be reached 11-7. 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 published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /AMY C BONAPARTE/Primary Examiner, Art Unit 1692
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Prosecution Timeline

Apr 20, 2023
Application Filed
Feb 05, 2026
Non-Final Rejection — §112 (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
80%
Grant Probability
99%
With Interview (+23.8%)
2y 2m
Median Time to Grant
Low
PTA Risk
Based on 734 resolved cases by this examiner. Grant probability derived from career allow rate.

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