DETIALED 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 .
Status of Claims
Claims 1-3, 5, 7 and 9-11 are pending in the instant application. Claim 1 is amended and claims 4, 6, 8 and 12 are cancelled via the amendment filed December 24th, 2025.
Priority
This is a 35 U.S.C. 371 National Stage filing of International Application No. PCT/KR2021/008780 filed July 9th, 2021, which claims priority under 35 U.S.C. 119(a-d) to KR10-2020-0116811 filed September 11th, 2020.
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on December 24th, 2025 has been entered.
Withdrawn Rejections
Applicant’s arguments and amendments, filed December 24th, 2025, with respect to the rejection(s) of claim(s) 1-3, 5, 6, and 9-12 under 35 USC 103 have been fully considered and are persuasive. Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of the art below.
Applicant has overcome this rejection by amending claim 1 to recite “the organic layer stream discharged from the decanter is directly supplied to the second distillation tower”.
Response to Remarks
Applicant’s arguments with respect to the rejection of claim(s) 1-3, 5, 6, and 9-12 under 35 USC 103 have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
In the response, Applicant argues that the new claim limitations of instant claim 1 are not taught by Kazuhiko. However, as the new grounds rejection relies on Godboel for the teachings of these new limitations, Applicant’s arguments are moot.
New 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.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim(s) 1-3, 5 and 7 are newly rejected under 35 U.S.C. 103 as being unpatentable over Godble et al (US 2005/0187401) in view of Kawakami et al (US 4,599,145) and Yoshimura et al (WO 2019/181697 A1, as cited on the IDS dated 01/20/2022).
Determining the scope and contents of the prior art. (See MPEP § 2141.01)
Godbel teaches a process for the recovery of olefinically unsaturated nitrites (Figure 1):
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Godbel teaches that a solution containing water, acrylonitrile, acetonitrile and impurities are sent through line 47 and passed to a recovery column, an extractive distillation-type of column, 50 (which corresponds to the first distillation tower of the instant invention). Godbel teaches that acrylonitrile and HCN are removed from the top of the recovery column and condensed in a condenser, 53 (which corresponds to the condenser of the instant invention) and a stream comprising water is removed from the recovery column through line 51. Godbel then teaches that the condensed stream is sent to the decanter (which corresponds to the decanter of the instant application), 54 where the acrylonitrile stream is decanted and sent through line 58 to further purification (not shown on the figure) and water from the decanter is removed through 56 and returned to column 50. Godbel teaches that the further purification is accomplished by passing the overhead stream to a second distillation tower to remove the impurities from the acrylonitrile (which corresponds to the second distillation tower of the instant invention).
Ascertainment of the differences between the prior art and the claims. (See MPEP § 2141.02)
Godbel does not explicitly teach that a part of the upper discharge stream from the second distillation tower is refluxed back to the second distillation tower at a flow rate ratio of 0.5 to 0.8. Godbel also does not explicitly teach that the feed stream is discharged from a reactor in which the nitrile-based monomer and a conjugated diene-based monomer are polymerized.
Finding of prima facie obviousness --- rationale and motivation (See MPEP § 2142-2143)
With regard to the split stream, Kawakami also teaches a process for the production of a nitrile monomer with compounds hydrogen cyanide, isobutyronitrile and cyanohydrin. Kawakami teaches that the products are sent to a distillation in a recovery column, 2. The overhead vapor is condensed in a condenser, 9 and sent to a decanter wherein the oil layer is separated. Kawakami then teaches that the oil layer is sent to a product column and after high boiling, the upper discharge stream is spilt and a part of the stream is refluxed in the distillation tower (Figure 2). Kawakami also teaches multiple flow rates were used including 100 ml/hr, 2-7 ml/hr, 14ml/hr and 134 ml/hr.
As Godbel teaches a method of recovering a nitrile monomer including a first distillation tower, condenser, decanter and direct path from the decanter to the second distillation tower, one of ordinary skill in the art would have been motivated to split part of the upper discharge stream from the second distillation tower is refluxed back to the second distillation tower at a flow rate ratio of 0.5 to 0.8, as Kawakami also teaches a similar recovery method for a nitrile monomer with the spilt stream refluxed back to the second distillation tower. One of ordinary skull in the art also would’ve been motivated by the general flow rates taught by Kawakami to optimize the nitrile monomer recovery process.
Concerning the feed stream being discharged from a reactor in which the nitrile-based monomer and a conjugated diene-based monomer are polymerized, Yoshimura also teaches a method for recovering an unsaturated nitrile monomer. Yoshimura teaches that the method comprises a strep for adjusting the pH of a nitrile rubber latex, a step for decompressing the nitrile rubber latex under heating conditions and an unsaturated nitrile monomer recovery step (claim 1). Yoshimura teaches that the nitrile rubber latex can be produced from a monomer mixture comprising a diene monomer (claim 6). Yoshimura teaches that the monomer mixture contains an unsaturated nitrile monomer and a carboxyl group monomer and that the diene monomer is particularly a conjugate diene having 4 or more carbons.
As Godbel teaches a method that produces a nitrile-based monomer, and Yoshimura teaches a method of recovery for a nitrile based monomer which comprises a step of producing a feed stream with a nitrile based monomer and conjugated diene-based monomer, one of ordinary skill would have had the motivation to combine the teachings to produce the methods of the instant invention.
In view of the above art, the method of instant claims 1 and 5 have been rendered obvious.
Regarding claim 2, both acetonitrile and hydrogen cyanide are used in the method above.
Regarding claim 3, acetonitrile has a boiling point of 82°C and acrylonitrile has a boiling point of 78°C, as evidenced by Teeter et al (US 241566 A).
Regarding claim 7, as seen above, Godbel teaches that the water from the decanter is removed through 56 and returned to column 50.
Claim(s) 1-3, 5, 7 and 9-11 are newly rejected under 35 U.S.C. 103 as being unpatentable over Godble et al (US 2005/0187401) in view of Kawakami et al (US 4,599,145) and Yoshimura et al (WO 2019/181697 A1, as cited on the IDS dated 01/20/2022), as applied to claim 1-3, 5 and 7 and in further view of Kazuhiko et al (WO 2012/090691, as cited on the IDS dated 08/18/2022).
Determining the scope and contents of the prior art. (See MPEP § 2141.01)
Neither Godble, Kawakami nor Yoshimura specifically teaches that each stream is supplied to a certain plate of the theoretically plate number. However, Godbel teaches that in the distillation towers, the stream is preferably taken from a location that is above one-third the distance from the bottom tray to the top of the column (paragraph [0045]). Godbel also teaches that the distillation towers contain 60-120 trays.
Ascertainment of the differences between the prior art and the claims. (See MPEP § 2141.02)
There is not a single embodiment wherein each stream is supplied to a plate at a certain percentage of the theoretical plate number.
Finding of prima facie obviousness --- rationale and motivation (See MPEP § 2142-2143)
However, Kazuhiko teaches a process for the production of acrylonitrile, see the schematic diagram below (Figure 1):
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Kazuhiko teaches that acrylonitrile, acetonitrile and hydrogen cyanide are absorbed in water and transferred to a recovery tower, 12 (page 3, paragraph 3). Kazuhiko teaches that most water is withdrawn from the tower through line 16 and from the top of the recovery tower, acrylonitrile, hydrogen cyanide, and water are distilled off by line 17 (page 3, paragraph 3). After being distilled off, Kazuhiko teaches that the upper discharge stream is condensed in a condenser and separated into two layers, an organic layer and an aqueous layer with a decanter. Kazuhiko then teaches that the organic layer is supplied to a dehydrocyanic acid dehydration tower 18. The gas contain hydrogen cyanide is distilled from the top of the tower. The crude acrylonitrile extracted from the bottom of the dehydrocyanic acid dehydration tower, 18, is then sent to a product tower, 25. Kazuhiko teaches that the product column is a tray column distillation column, wherein the bottom liquid containing the high-boiling substance is withdrawn through line 28 and the acrylonitrile is obtained as a product from line 27 (page 3, paragraph 7). Kazuhiko teaches that the distillate vapor of the product tower, 25, is withdrawn through line 26 and send to a condenser for condensation. The condensate is refluxed back to the product tower, 25. Kazuhiko then teaches that the acrylonitrile is obtained as a product from line 27 (page 3, paragraph 7).
Further, Kazuhiko teaches that within the dehydrocyanic acid dehydration tower, the liquid is withdrawn in the middle stage of the tower. Kazuhiko teaches “middle stage: to mean a portion below the top of the column. Kazuhiko also provides an example, in the case of a distillation column having 50-65 stages in all, it is preferable to ser the line to 23-30 stages, counting From the bottom of the column. Kazuhiko teaches that this method is preferable from the viewpoint of efficiently separate water from crude acrylonitrile (page 3, paragraph 5).
Regarding claims 9-11, as both Godbel and Kazuhiko teach similar processes for the recovery of a nitrile monomer, one of ordinary skill in the art would have been motivated by teachings of Kazuhiko to use this rationale when adjusting the feed streams, as Kazuhiko teaches that it improves efficiency.
Correspondence
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/A.G.K./Examiner, Art Unit 1626
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699