CTNF 18/564,332 CTNF 101756 Notice of Pre-AIA or AIA Status 07-03-aia AIA 15-10-aia 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 A preliminary amendment was filed on 11/27/2023. Claims 1-10 have been cancelled, and claims 11-20 have been added. Claims 11-20 are currently pending and under examination. Priority The instant application is a national stage application of PCT/FR2022/051054 filed on 06/03/2022 which claims foreign priority to French application no. FR2105962 filed on 06/07/2021. Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55. 23-19 AIA Should applicant desire to obtain the benefit of foreign priority under 35 U.S.C. 119(a)-(d) prior to declaration of an interference, a certified English translation of the foreign application must be submitted in reply to this action. 37 CFR 41.154(b) and 41.202(e). Failure to provide a certified translation may result in no benefit being accorded for the non-English application. Information Disclosure Statement The information disclosure statements (IDS) submitted on 11/27/2023 and 03/17/2026 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements have been considered by the examiner. Claim Rejections - 35 USC § 103 07-06 AIA 15-10-15 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. 07-20-aia AIA 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. 07-23-aia AIA 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. 07-21-aia AIA Claim s 11-18 are rejected under 35 U.S.C. 103 as being unpatentable over Taniguchi et al. (JP2016130236A, published 07/21/2016, IDS dated 11/27/2023) . Taniguchi et al. teaches a fluorine-containing compound and a method for producing an azeotrope-like composition of CFO-1113 (chlorotrifluoroethylene, CTFE) and HFC-143 (1,1,2-trifluoroethane) (see Abstract). Examples of the method for producing trifluoroethylene (HFO-1123) include chlorotrifluoroethylene (CFO-1113) or 1,1,2-trichloro-1,2,2-trifluoroethane (CFC-113). There is known a method of reducing (hydrogen reduction reaction) by reacting with hydrogen in the presence of a hydrogenation catalyst. The reaction products of these production methods include CFO-1113 or CFC-113, which are unreacted raw materials, and various by-products in addition to the target substance, HFO-1123. The unreacted raw material contained in the reaction product can be separated from the reaction product and recycled as the raw material in order to improve the production efficiency of HFO-1123. In addition to unreacted raw materials, it is preferable to effectively use a compound that is contained as a by-product and that can produce HFO-1123. For example, hydrochlorofluoroalkanes which are by-products such as 1-chloro-1,2,2-trifluoroethane (HCFC-133) and 1-chloro-1,1,2-trifluoroethane (HCFC-133b) It is preferable to separate and effectively use as a raw material for producing HFO-1123 (see paragraphs 4-6). A stainless-steel reaction tube having an inner diameter of 2.3 cm and a length of 50 cm is filled with palladium-supported activated carbon in which 0.5 parts by weight of palladium (in group 10 of the Periodic Table of the Elements) is loaded with respect to 100 parts by weight of coconut shell activated carbon (corresponding to a fixed catalytic bed comprising a catalyst). A layer was formed. The catalyst layer in the reaction tube thus formed was controlled at 80 °C by an electric heater, and a raw material composition having an internal pressure of 0.04 MPa and a molar ratio of CTFE to hydrogen of 1.0 was used as the raw material composition with respect to the catalyst layer. HFO-1123 (trifluoroethylene) was manufactured by supplying the reaction tube so that the contact time was 30 seconds. Next, the product gas discharged from the outlet (corresponding to instant stream A) of the reaction tube was subjected to alkali cleaning and then dehydrated to recover crude HFO-1123 (trifluoroethylene). The composition of the recovered crude trifluoroethylene is shown in the lower column of Table 8. Next, the crude HFO-1123 obtained in Production Example 1 was recovered and supplied at a flow rate of 10 mol / h from the top of a 30-stage distillation column to the 21st stage, a pressure of 1.0 Mpa (equivalent to 10 Bar), a top temperature of 4.9 °C, Distillation is continuously carried out at a bottom temperature of 36.9 °C. The reflux liquid is supplied to the uppermost stage of the distillation column. Distillation is performed at a reflux ratio of 21.0. A fraction (distillate A) in which low-boiling components are concentrated from the top of the column is distilled at a flow rate of 1.1 mol/h, and the temperature in the column is 9.0 °C, that is, from the 14th stage from the top. High-purity HFO-1123 (distillate B, corresponding to instant stream C1) was distilled at a flow rate of 4.5 mol/h, and a fraction (bottom liquid C, corresponding to instant stream C2) in which high-boiling components were concentrated from the bottom of the column was 4.3 mol/h. Distillate to a flow rate of Table 9 shows the compositions of the distillates A and B and the bottoms C, the tower top temperature, the 14th stage temperature, and the tower bottom temperature. Next, the distillation composition (CFO-1113/HFC-143 = 9) prepared by mixing and adjusting the bottoms C (corresponding to purifying instant stream C2) obtained by the above distillation at a flow rate of 4.4 mol/h and CFO-1113 at 10.6 mol/h) at a flow rate of 15.0 mol/h from the top of the distillation column having 40 stages to the 30th stage, the pressure is 0.4 Mpa (4 Bar), the top temperature is 14.7 °C, and the bottom temperature is 77.9 ° C. Distill continuously. The reflux liquid is supplied to the uppermost stage of the distillation column. A distillate containing an azeotropic composition comprising CFO-1113 and HFC-143 or an azeotrope-like composition as a distillate is distilled from the top of the column at a flow rate of 14.4 mol/h, and the bottom is discharged from the bottom of the column. Table 10 shows the composition of the distillation composition, distillate (corresponding to instant stream D1), and bottoms fractions (corresponding to instant stream D2). The distillate has 74.1825 mol% (calculated to be 76.5 weight %) of chlorotrifluoroethylene and 11.4315 mol% (calculated to be 8.51 weight %) of PNG media_image1.png 622 831 media_image1.png Greyscale 1,1,2-trifluoroethane (corresponding to less than 15% by weight as required by instant claim 11). The teachings of Taniguchi et al. differ from that of the instantly claimed invention in that Taniguchi et al. does not exemplify the process for producing trifluoroethylene comprising the step of: c) recycling stream D1 to step a) as required by instant claim 1. It would have been obvious before the effective filing date of the claimed invention to modify the teachings of Taniguchi et al. by recycling the distillate of unreacted starting material, as taught by Taniguchi et al., to arrive at the instantly claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to recycle the purified, unreacted starting material because, as taught by Taniguchi et al., the unreacted raw material can be separated from the reaction product and recycled as the raw material in order to improve the production efficiency of HFO-1123. One of ordinary skill in the art would have a reasonable expectation of success because recycling purified, unreacted starting material is common practice in chemical processing. In regard to instant claim 12, table 8 of Taniguchi et al. teaches the crude product gas (corresponding to instant stream A) comprising HFO-1123 (trifluoroethylene), CFO-1113 (chlorotrifluoroethylene), and HFC-143 (1,1,2-trifluoroethane). In regard to instant claim 13, Taniguchi et al. teaches a stream, corresponding to instant stream D1, which comprises CFO-1113 (chlorotrifluoroethylene) in 74.1825 mol % (calculated to be 76.5 wt. %) in table 10 (shown above). In regard to instant claim 14, Taniguchi et al. teaches azeotrope-like composition of CFO-1113 (chlorotrifluoroethylene, CTFE) and HFC-143 (1,1,2-trifluoroethane) (see Abstract). In regard to instant claim 15, Taniguchi et al. teaches distilling the crude stream (corresponding to purifying instant stream A) into multiple fractions which include distillate B which comprises CFO-1113 (corresponding to instant stream C1) and a fraction bottom liquid C comprising CFO-1113 (chlorotrifluoroethylene) and HFC-143 (1,1,2-trifluoroethane) (corresponding to instant stream C2) followed by stilling the bottoms fraction to produce a distillate (corresponding to instant stream D1) and another bottoms fraction (corresponding to instant stream D2). In regard to instant claims 16 and 17, Taniguchi et al. teaches the distillation step (corresponding to instant step b2)) having a pressure of 0.4 Mpa (4 Bar) and a top temperature of 14.7 °C. In regard to instant claim 18, Taniguchi et al. teaches palladium (a group 10 metal) as a metal in the catalyst . 07-22-aia AIA Claim 19 is rejected under 35 U.S.C. 103 as being unpatentable over Taniguchi et al. (JP2016130236A, published 07/21/2016, IDS dated 11/27/2023) , as applied to claim s 11 and 18 above, and further in view of Asahi et al. (EP2993213A1, published 09/03/2016, IDS dated 11/27/2023) . The teachings of Taniguchi et al. were discussed above. The teachings of Taniguchi et al. differ from that of the instantly claimed invention in that Taniguchi et al. does not teach that the catalyst comprises palladium supported on α-alumina. Asahi et al. teaches a method for producing a composition containing trifluoroethylene by gas-phase hydrogen reduction of chlorotrifluoroethylene, wherein chlorotrifluoroethylene (CTFE) and hydrogen are reacted in the presence of a palladium catalyst at 80 °C or higher (corresponding to instant claim 1, step a), and the obtained reaction product is distilled to obtain trifluoroethylene containing chlorotrifluoroethylene and optionally at least one compound selected from a Markush group consisting of by-products, wherein the proportion of each of the Markush group of compounds is 0.0001 mass% (see 0015). The catalyst is preferably a catalyst having only palladium or a palladium alloy supported on a carrier, or a catalyst having a mixture of palladium with a metal other than palladium supported on a carrier. A catalyst having palladium and a metal other than palladium supported on a carrier tends to have high catalyst durability as compared with a catalyst having only palladium supported on a carrier. The carrier may, for example, be activated carbon or a metal oxide (such as alumina, zirconia or silica), and is preferably activated carbon in view of the activity, the durability and the reaction selectivity. It would have been obvious before the effective filing date of the claimed invention to combine the teachings of Taniguchi et al. with the teachings of Asahi et al. by substituting the coconut shell activated carbon support, as taught by Taniguchi et al., with the alumina oxide (α-alumina) in the Markush group of catalyst supports, as taught by Asahi et al., to arrive at the instantly claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to substitute the activated carbon for alumina oxide because Asahi et al. teaches activated carbon and alumina oxide to be interchangeable supports for the catalyst. One of ordinary skill in the art would have a reasonable expectation of success because both references make the same product from the same starting material . 07-22-aia AIA Claim 20 is rejected under 35 U.S.C. 103 as being unpatentable over Taniguchi et al. (JP2016130236A, published 07/21/2016, IDS dated 11/27/2023) , as applied to claim 11 above, and further in view of Grouch et al. (NPL, published 04/18/2004, PTO-892) The teachings of Taniguchi et al. were discussed above. The teachings of Taniguchi et al. differ from that of the instantly claimed invention in that Taniguchi et al. does not teach the chlorotrifluoroethylene and the hydrogen are in anhydrous form. Grouch et al. teaches the removal of admixed or dissolved water from starting materials and finished products is an important feature of organic chemistry and lab work. As a rule, water must be considered as an objectional impurity and must be removed since it may bring on undesired reactions (hydrolytic) or exert an undesired catalytic effect (see paragraph 1). It would have been obvious before the effective filing date of the claimed invention to combine the teachings of Taniguchi et al. with the teachings of Grouch et al. by drying the starting material gas to arrive at the instantly claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to dry the starting material gases because, as taught by Grouch et al., water must be considered as an objectional impurity and must be removed since it may bring on undesired reactions (hydrolytic) or exert an undesired catalytic effect. One of ordinary skill in the art would have a reasonable expectation of success because the removal of impurities in the starting material is common practice in synthetic chemistry. Conclusion No claim is found allowable. Any inquiry concerning this communication or earlier communications from the examiner should be directed to KRISTEN WEEKS BRADY whose telephone number is (571)272-5906. The examiner can normally be reached 8am-5pm. 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) 272-5960. 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. /KRISTEN W BRADY/ Examiner, Art Unit 1692 /SCARLETT Y GOON/ Supervisory Patent Examiner, Art Unit 1693 Application/Control Number: 18/564,332 Page 2 Art Unit: 1692 Application/Control Number: 18/564,332 Page 3 Art Unit: 1692 Application/Control Number: 18/564,332 Page 4 Art Unit: 1692 Application/Control Number: 18/564,332 Page 5 Art Unit: 1692 Application/Control Number: 18/564,332 Page 6 Art Unit: 1692 Application/Control Number: 18/564,332 Page 7 Art Unit: 1692 Application/Control Number: 18/564,332 Page 8 Art Unit: 1692 Application/Control Number: 18/564,332 Page 9 Art Unit: 1692
