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Last updated: April 15, 2026
Application No. 18/037,571

TWO-STAGE PREPARATION PROCESS FOR ?,?-ETHYLENICALLY UNSATURATED CARBOXYLIC ACIDS AND PLANT FOR THE PURPOSE

Non-Final OA §103
Filed
May 18, 2023
Examiner
RHOADES, DEREK JAMES
Art Unit
1692
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Basf Se
OA Round
1 (Non-Final)
70%
Grant Probability
Favorable
1-2
OA Rounds
3y 7m
To Grant
99%
With Interview

Examiner Intelligence

Grants 70% — above average
70%
Career Allow Rate
38 granted / 54 resolved
+10.4% vs TC avg
Strong +31% interview lift
Without
With
+31.2%
Interview Lift
resolved cases with interview
Typical timeline
3y 7m
Avg Prosecution
29 currently pending
Career history
83
Total Applications
across all art units

Statute-Specific Performance

§103
43.3%
+3.3% vs TC avg
§102
14.8%
-25.2% vs TC avg
§112
22.8%
-17.2% vs TC avg
Black line = Tech Center average estimate • Based on career data from 54 resolved cases

Office Action

§103
DETAILED ACTION STATUS OF THE APPLICATION Receipt is acknowledged of Applicants’ Amendments and Remarks, filed 18 May 2023, in the matter of Application No. 18/037,571. Said documents have been entered on the record. The Examiner further acknowledges the following: The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA . Claims 16-30 are pending. Claims 1-15 have been cancelled. Claims 16-30 have been newly added. Thus, claims 16-30 represent all claims currently under consideration. Priority Acknowledgment is made of Applicants’ claim for foreign priority under 35 U.S.C. 119 (a)-(d). The certified copy has been filed in the present application filed 18 May 2023, and in parent Application No. PCT/EP2021/079553, filed on 25 October 2021. Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55. Applicant claims foreign priority to Application No. EP10108603.9, filed on having an effective filing date of 19 November 2020. Domestic Priority data as claimed by Applicant: This application is a 371 of PCT/EP2021/079553 (10/25/2021) Foreign Applications: EUROPEAN PATENT 10108603.9 (11/19/2020) Information Disclosure Statement (IDS) The information disclosure statement (IDS) submitted on 26 May 2023 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the IDS is being considered by the Examiner. Specification The following title correction is suggested: “….?,?-ethylenically…” should read “…α, β-ethylenically…” Appropriate correction is required. Claim Objections Claim 22 is objected to because of the following informalities: In lines 1-2, “…specific surface area…” should read “…specific surface area per unit gas volume…” in a manner consistent with the written description (Specification; page 14, lines 11-17). Appropriate correction is required. Claim Interpretation The phrase “structured packing” as recited in claim 24 will be interpreted in a manner consistent with the instant specification as a packing that has an ordered structure, is not random, and is understood to mean internals such as, for example, metal plates (trays), metal meshes, metal grids, etc. that offer high (contact) surface area, but low resistance to gas flow (Specification; page 14, lines 23-28). The phrase “high specific surface area” of the exchangeable structure as recited in claims 16 and 21 will be interpreted in a manner consistent with the instant specification as a surface area greater than the expected surface area of the connecting conduit if the exchangeable structure were absent (Specification; page 11, lines 28-31). The term “plant” as recited in claims 21-30 will be interpreted in a manner consistent with the instant specification, which recites the operation of a plant for executing this method (Specification; page 1, line 35). Under a broadest reasonable interpretation, the term “plant” is being interpreted as an apparatus, facility, or factory capable of executing the instantly claimed method (c.f., Roget’s 21st Century Thesaurus; 2005, page 629, Col. 2). The phrase “cross-sectional area of the housing of the exchangeable structure” as recited in claim 28 will be interpreted in a manner consistent with the instant specification as any area of the housing at right angles to the flow direction of the gas stream comprising at least one α,β-ethylenically unsaturated aldehyde (Specification; page 16, lines 34-37). 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 (i.e., changing from AIA to pre-AIA ) 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, 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 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 16-30 are rejected under 35 U.S.C. 103 as being unpatentable over Tanimoto and Hakozaki (US 2010/0130777 A1; hereinafter “Tanimoto”), in view of Tanimoto and Masaki (US 2008/0021240 A1; hereinafter “Tanimoto-2”) Regarding claims 16 and 21, Tanimoto teaches a process for producing acrylic acid by two-stage catalytic vapor-phase oxidation of a propylene-containing gas comprising oxygen at a first fixed bed reactor which is loaded with a catalyst comprising a mixed metal oxide of molybdenum for converting propylene to acrolein by catalytic vapor-phase oxidation to produce an acrolein-containing gas (Tanimoto; Title; Abstract; claims 1 and 3; paragraphs [0025] and [0047]). In the second reaction stage, Tanimoto teaches that the formed acrolein-containing gas is further subjected to a catalytic vapor-phase oxidation at a second fixed bed reactor which is loaded with a catalyst for converting acrolein to acrylic acid (Tanimoto; Title; Abstract; claims 1 and 4). One of ordinary skill in the art would recognize propylene as an alkene, acrolein as an α,β-ethylenically unsaturated aldehyde, and acrylic acid as an α,β-ethylenically unsaturated carboxylic acid, in a manner consistent with the instant claims. Tanimoto further teaches that the outlet from the first reactor (the upper end) and the inlet to the second reactor (the upper end) were connected with a steel pipe (Tanimoto; paragraphs [0046] and [0088]). One of ordinary skill in the art would recognize the steel connecting pipe of Tanimoto as a connecting conduit, in a manner consistent with the instant claims. In addition, Tanimoto teaches that this process is characterized in that a filler formed of a solid inert material is disposed at a cooling part which is provided on the downstream side to the direction of gas flow through the catalyst layer in the first reactor and/or on the gas outlet side of the first reactor, in such a way that the voidage in the filler becomes 45-99% (Tanimoto; Abstract; claim 1; paragraph [0012]). The skilled artisan would recognize that the gas outlet side of the first reactor comprises the beginning of the connecting conduit, and the presence of an inert material would introduce a high specific surface area, as recited in the instant claims. Tanimoto further teaches that a treating agent for adsorbing and/or absorbing the organic matters and/or carbides is disposed at the cooling part disposed on the upstream side to the direction of gas flow through the catalyst layer in the second reactor and/or the gas inlet part of the second reactor (Tanimoto; claim 2). Complex oxides containing aluminum and silicon are particularly preferred, and the treating agent is used for preventing adhesion or deposition of organic matters or carbides to and on the catalyst layer loaded in the second reactor. (Tanimoto; paragraphs [0020]-[0021]). The skilled artisan would recognize that the gas inlet part of the second reactor comprises the end of the connecting conduit, and the presence of a treating agent would introduce a high specific surface area, as recited in the instant claims. Tanimoto fails to teach an exchangeable structure which is disposed in the connecting conduit, as recited in the instant claims. Instead, Tanimoto teaches that the organic matters and/or carbides which are precipitated or adsorbed and/or absorbed onto the solid inert material loaded in the cooling part in the first reactor or onto the treating agent loaded in the cooling part of the second reactor can be safely and efficiently removed by an aeration treatment using a mixed gas, at a frequency of at least once a year (Tanimoto; paragraph [0034]). However, Tanimoto-2 teaches a method for gas-phase catalytic oxidation using a fixed bed reactor, for producing (meth)acrylic acid from propylene in a stable continuous operation over long term, maintaining high yield and suppressing increase in pressure loss (Tanimoto-2; Title; Abstract; claims 1 and 6). The fixed bed reactor may be a stand-alone apparatus or may be one which is incorporated into a production plant (Tanimoto-2; paragraph [0013]). Of particular note, Tanimoto-2 teaches that a treating agent for removing organic substance and/or carbides is disposed on the downstream side of the catalyst for the first stage reaction and on the upstream side of the catalyst for the second stage reaction, in respect of the direction of the gas flow, and it is desirable that at least part of the treating agent is exchanged at a frequency of at least once a year (Tanimoto-2; Abstract; claim 7). Tanimoto-2 further teaches that preferably regularly exchanging at least a part or entire amount of the treating agent, catalyst deterioration can be prevented and stable continuous operation over a prolonged period maintaining high yield and suppressing increase in the pressure loss at the catalyst layer(s) becomes possible (Tanimoto-2; paragraphs [0006] and [0015]). One of ordinary skill in the art would recognize the treating agent of Tanimoto-2, which is regularly exchanged to maintain the efficiency of the process, as an exchangeable structure, in a manner consistent with the instant claims. The prior art as taught by Tanimoto and Tanimoto-2 reside in the closely overlapping technical area of acrylic acid production from propylene via two-stage vapor-phase catalytic oxidation, and are therefore deemed analogous art, as described in MPEP § 2141.01(a). In addition, Tanimoto teaches that the aeration treatment must be carried out with a mixed gas at 260-440 ºC and when the aeration treatment is not given over an excessively long period, the organic matters and/or carbides begin to precipitate also on the catalyst layers, leading to a possibility of inducing even clogging of the reaction tubes (Tanimoto; paragraph [0037]). As such, the skilled artisan would recognize that the aeration treatment of the treating agent as taught by Tanimoto could be substituted with exchanging the treating agent as taught by Tanimoto-2 with a reasonable expectation of success as an obvious alternative for obtaining a stable continuous operation of acrylic acid over a prolonged period. Such an endeavor would result in the simple substitution of one known element for another to obtain predictable results, as described in MPEP § 2143(I)(B). Furthermore, such an endeavor would result in choosing from a finite number of identified, predictable solutions with a reasonable expectation of success and would therefore be “obvious to try,” as described in MPEP § 2143(I)(E). Therefore, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have substituted the treating agent of Tanimoto with the exchangeable treating agent of Tanimoto-2 to arrive at the claimed method and apparatus as recited in the instant claims. The motivation to do so would permit the skilled artisan to pursue, with a reasonable expectation of success, an obvious alternative process for preventing catalyst deterioration and obtaining stable continuous operation over a prolonged period while maintaining high yield and suppressing increase in the pressure loss at the catalyst layer, as described above. Regarding claim 17 depending from claim 16, Tanimoto teaches a first reactor temperature of 330 ºC, a second reactor temperature of 260 ºC, and the temperature of the connecting pipe was maintained at 180 ºC (Tanimoto; paragraphs [0044]-[0046]). Given the significantly lower temperature of the connecting conduit, the skilled artisan could reasonably deduce that the flow rate of the gas stream comprising acrolein would be slowed in the region of the exchangeable structure, in a manner consistent with the instant claim. Therefore, as with claim 16, it would have been prima facie obvious to arrive at the claimed process based on Tanimoto in view of Tanimoto-2. Regarding claim 18 depending from claim 16, Tanimoto teaches a first reactor temperature of 330 ºC, and the temperature of the connecting pipe was maintained at 180 ºC (Tanimoto; paragraphs [0044] and [0046]). This represents a temperature difference of 150 ºC, a value that resides within the range recited in the instant claim. MPEP § 2144.05(I) states that “[i]n the case where the claimed ranges ‘overlap or lie inside ranges disclosed by the prior art’ a prima facie case of obviousness exists.” Regarding claim 19 depending from claim 16, Tanimoto-2 teaches that it is desirable that at least part of the treating agent is exchanged at a frequency of at least once a year (Tanimoto-2; Abstract; claim 4). Tanimoto and Tanimoto-2 do not explicitly teach the claim limitation in which the exchangeable structure is exchanged while the first reactor and/or second reactor is not be ing cooled below 150 ºC, as recited in the instant claim. However, Tanimoto teaches that a jacket for heating medium circulation is disposed over the whole length of the first and second reactors and was maintained at 330 ºC for the first reactor and 260 ºC for the second reactor (Tanimoto; paragraphs [0044]-[0045]). Therefore, the skilled artisan would reasonably deduce that the exchangeable structure could be exchanged once or periodically while the first reactor and/or second reactor is not being cooled below 150 ºC, in a manner consistent with the instant claim. Therefore, as with claim 16, it would have been prima facie obvious to arrive at the claimed process based on Tanimoto in view of Tanimoto-2. Regarding claim 20 depending from claim 16, Tanimoto teaches a process for producing acrylic acid by two-stage catalytic vapor-phase oxidation of propylene (Tanimoto; Title; Abstract). Regarding claims 22-23 depending from claim 21, Tanimoto and Tanimoto-2 do not explicitly teach wherein the exchangeable structure has a specific surface are per unit gas volume of at least 400 m2/m3 or at least 600 m2/m3, as recited in the instant claims. In spite of this deficiency, Tanimoto and Tanimoto-2 teach that the use rate of the treating agent can be suitably adjusted according to the kind, specific gravity and shape of the treating agent selected for individual occasions, and to the kind, specific gravity, shape and amount used of the catalyst, and is not particularly limited (Tanimoto; paragraph [0023] and Tanimoto-2; paragraph [0028]). In addition, Tanimoto teaches that the gas outlet side of the first reactor comprising acrolein can be configured in such a way that the voidage in the filler becomes 45-99% (Tanimoto; Abstract; claim 1). As such, the skilled artisan could arrive at the instantly claimed ranges through means of routine experimentation that is non-inventive in nature. MPEP § 2144.05(II) states that “[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.” Finally, absent any demonstration of criticality, there is no clear indication in the present application that the recited ranges for the specific surface area per unit gas volume is critical to the claimed invention, which would have supported the non-obviousness of an exchangeable structure having a specific surface area of at least 400 m2/m3 or at least 600 m2/m3, as recited in the instant claims. Thus, it is unclear to what extent (if any) extent this parameter contributes to the criticality of the claimed invention, and as a result the present application does not clearly demonstrate a criticality for the ranges recited in instant claims 22-23. MPEP § 2144.05(III)(A) states that “The law is replete with cases in which the difference between the claimed invention and the prior art is some range or other variable within the claims… In such a situation, the applicant must show that the particular range is critical, generally by showing that the claimed range achieves unexpected results relative to the prior art range.” Therefore, as with claim 21, it would have been prima facie obvious to arrive at the claimed process based on Tanimoto in view of Tanimoto-2 through means of routine experimentation. Regarding claims 24 and 26 depending from claim 21, Tanimoto teaches that the shape of the solid inert material is not particularly limited, and for example it can be, besides Raschig ring, sphere, column or ring, block, rod, plate or wire net (Tanimoto; paragraph [0016]). In addition, Tanimoto-2 teaches that the shape of the treating agent is not critical, but any optional shape may be chosen. For example, those shaped with ordinary tabletting machine, extrusion molding machine or granulating machine, such as sphere, column, cylinder, star, ring, tablet, pellet and the like can be named (Tanimoto-2; paragraph [0026]). The skilled artisan would recognize that structured packing consisting of ring shaped structures or a wire net would comprise channels. Regarding claim 25 depending from claim 21, Tanimoto and Tanimoto-2 teach the use of ceramic balls (Tanimoto; Example 3; Table 1; and Tanimoto-2; Examples 11-12; Table 1). Regarding claim 27 depending from claim 21, Taniomoto-2 teaches that the place of disposing the treating agent is not particularly limited so long as the treating agent alone can be withdrawn and refilled, for example, on the upper part of a tube-holding upper plate in the reactor (Tanimoto-2; paragraph [0029]). The skilled artisan could reasonably deduce that the place of disposing the treating agent would necessarily comprise housing, and Tanimoto in view of Tanimoto-2 would inform the skilled artisan that the exchangeable structure can be disposed within the connecting conduit, as detailed above. Therefore, as with claim 21, it would have been prima facie obvious to arrive at the claimed process based on Tanimoto in view of Tanimoto-2. Regarding claim 28 depending from claim 27, Tanimoto and Tanimoto-2 fail to explicitly teach the cross-sectional area of the housing of the exchangeable structure is greater than the cross-sectional area of the connecting conduit, as recited in the instant claim. However, the skilled artisan would recognize that the presence of treating agent within the exchangeable structure as rendered obvious by Tanimoto in view of Tanimoto-2 as detailed above would introduce areas within the housing wherein right angles to the flow direction of the gas stream comprising acrolein that flows through would occur (c.f., Claim Interpretation and Specification at page 16, lines 34-37). Thus, the housing of the exchangeable structure as taught by Tanimoto in view of Tanimoto-2 would necessarily comprise a cross-sectional area that is great than the cross-sectional rea of the connecting conduit and therefore, as with claim 27, it would have been prima facie obvious to arrive at the claimed process based on Tanimoto in view of Tanimoto-2. Regarding claim 29 depending from claim 21, Tanimoto teaches a first reactor and a second reactor that are fixed bed shell-and-tube reactors, wherein a jacket for the heating medium is disposed outside of the reactors (Tanimoto; paragraphs [0086]-[0087]). Regarding claim 30 depending from claim 21, Tanimoto teaches that a temperature of the heating medium (reaction temperature) in the first reactor was maintained at 320 ºC, and the part down to 200 mm from the tops of the reaction tubes was maintained at 260° C to function as the cooling part, by a separately externally disposed jacket for the heating medium circulation, and the connecting steel pipe was maintained at 180° C (Tanimoto; paragraphs [0086] and [0088]). The skilled artisan could reasonably deduce that the heat circulation medium that cools the first reaction gas stream comprising acrolein as a cooler, in a manner consistent with the instant claim. Based on the combined teachings of the references, the Examiner submits that a person of ordinary skill in the art would have had a reasonable expectation of success of arriving at the instantly claimed process and apparatus. Therefore, the invention as a whole would have been prima facie obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, and absent a clear showing of evidence to the contrary. Conclusion Any inquiry concerning this communication or earlier communications from the Examiner should be directed to DEREK RHOADES whose telephone number is (703)-756-5321. The Examiner can normally be reached Monday–Thursday, 7:30 am–5:00 pm EST; Friday, 7:30 am–4:00 pm EST. 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 on 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. /D.R./Examiner, Art Unit 1692 /AMY C BONAPARTE/Primary Examiner, Art Unit 1692
Read full office action

Prosecution Timeline

May 18, 2023
Application Filed
Dec 23, 2025
Non-Final Rejection — §103
Mar 26, 2026
Response Filed

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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
70%
Grant Probability
99%
With Interview (+31.2%)
3y 7m
Median Time to Grant
Low
PTA Risk
Based on 54 resolved cases by this examiner. Grant probability derived from career allow rate.

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