Ex Parte Karube et alDownload PDFPatent Trial and Appeal BoardApr 28, 201713319588 (P.T.A.B. Apr. 28, 2017) Copy Citation United States Patent and Trademark Office UNITED STATES DEPARTMENT OF COMMERCE United States Patent and Trademark Office Address: COMMISSIONER FOR PATENTS P.O.Box 1450 Alexandria, Virginia 22313-1450 www.uspto.gov APPLICATION NO. FILING DATE FIRST NAMED INVENTOR ATTORNEY DOCKET NO. CONFIRMATION NO. 13/319,588 11/09/2011 Daisuke Karube 20111684A 9593 513 7590 05/02/2017 WENDEROTH, LIND & PONACK, L.L.P. 1030 15th Street, N.W., Suite 400 East Washington, DC 20005-1503 EXAMINER BAKSHI, PANCHAM ART UNIT PAPER NUMBER 1671 NOTIFICATION DATE DELIVERY MODE 05/02/2017 ELECTRONIC Please find below and/or attached an Office communication concerning this application or proceeding. The time period for reply, if any, is set in the attached communication. Notice of the Office communication was sent electronically on above-indicated "Notification Date" to the following e-mail address(es): ddalecki@wenderoth.com eoa@ wenderoth. com PTOL-90A (Rev. 04/07) UNITED STATES PATENT AND TRADEMARK OFFICE BEFORE THE PATENT TRIAL AND APPEAL BOARD Ex parte DAISUKE KARUBE, TSUNEO, AKINARRI SUGIYAMA, and TAKASHI SHIBANUMA Appeal 2016-0030021 Application 13/319,588 Technology Center 1600 Before RICHARD M. LEBOVITZ, FRANCISCO C. PRATS, and RYAN H. FLAX, Administrative Patent Judges. LEBOVITZ, Administrative Patent Judge. DECISION ON APPEAL This appeal involves claims directed to a process of preparing a fluorine containing propane. The Examiner rejected the claims under 35 U.S.C. § 103(a) as obvious. We have jurisdiction under 35 U.S.C. § 6(b). The rejection is affirmed. 1 The Appeal Brief (“Appeal Br.”), page 2, lists Daikin Industries, Ltd, as the real party in interest. Appeal 2016-003002 Application 13/319,588 STATEMENT OF THE CASE Appellants appeal from the Examiner’s rejection of claims 1—6 under pre-AIA 35 U.S.C. § 103(a) as obvious in view of Belen’Kill (US Pat. No. 6,184,426 Bl, pat. Feb. 6, 2001), Saunders (Gas-Phase Chemiionization Reactions of Antimony Pentafluoride, J. Am. Chem. Society 5031—34 (1981)), Siskin (US Pat. No. 4,069,268, pat. Jan. 17, 1978), and Brunet {Reactivity of antimony mixed halides for the fluorination of tetrachlorethene (PCE) in liquid phase, J. Molecular Catalysis A: Chemical 142 183-86 (1999)). Claim 1, the only independent claim on appeal, is reproduced below: 1. A process for preparing a fluorine-containing propane represented by the formula: CF2XCF2CH3 wherein X is F or Cl, the process comprising reacting tetrafluoroethylene and methyl chloride in the presence of an antimony halide represented by the formula: SbFxCl5-x wherein x is a value of 0 to 5. REJECTION Claim 1 is directed to a process for preparing a fluorine-containing propane. The fluorine-containing propane can also contain chloride. The process comprises reacting 1) tetrafluoroethylene and 2) methyl chloride in the presence of 3) antimony halide as a catalyst. Tetrafluoroethylene is an olefin. Belen’Kill is cited by the Examiner for a process for making a fluorine-containing propane comprising reacting a 1) halogen olefin and 2) methyl fluoride in the presence of 3) antimony pentafluoride as the catalyst, Office Action (mailed Dec. 26, 2014) (“Non-Final Act.”) 3^4. The Examiner found that the halogen olefin and the antimony pentafluoride are 2 Appeal 2016-003002 Application 13/319,588 within the scope of the claim. Id. at 4. The Examiner found that Belen’Kill does not teach methyl chloride as in claim 1. Id. at 5. The Examiner determined that “it would have been obvious to a person of ordinary skill in the art that methyl fluoride of Bellen'Kill’s [sic] process may be substituted with chemically similar and commercially-available methyl chloride compound.” Id. Furthermore, the Examiner found that Saunders teaches the reaction of organic halides (RX), corresponding to 2) methyl chloride of claim 1 or methyl fluoride of Belen’Kill, with 3) antimony pentafluoride, the catalyst of claim 1 and Belen’Kill. Id. The Examiner found that, based on Saunders, it would have been obvious that methyl chloride and methyl fluoride interact with antimony pentafluoride in a mechanistically similar manner to form a carbocation. Id. The Examiner also found that, based on Saunders, the skilled worker would have a reasonable expectation of success that 2) methyl fluoride of Belen’Kill’s process could be substituted for methyl chloride meeting the corresponding limitation of the claim. Id. at 5—6. Similar properties Appellants contend that the Examiner’s “presumed expectation” that methyl fluoride would have similar properties to methyl chloride is an error because the Examiner relied upon “close structural similarity” and the two compounds are not positional isomers or homologs. Appeal Br. 6. We disagree. Fluorine and chlorine are halogens. It is basic chemical knowledge that members of the same periodic group have similar chemical properties. Fluorine and chlorine are members of the same periodic group, 3 Appeal 2016-003002 Application 13/319,588 the halogens, and would, therefore, be expected to have similar chemical properties. See Ans. 13. Expectation of Success Appellants contend that one skilled in the art would not have reasonably expected that methyl chloride and methyl fluoride would have similar properties in the claimed reaction. Appeal Br. 7. Appellants rely on several lines of evidence to support this argument. Appellants cited the Tung and Nappa publications as providing evidence that the skilled worker “would believe that the C-F bond would be much easier to break than the C-Cl bond in the catalyzed gas phase addition reaction using the catalyst of the present invention, and thus [would] not substitute the methyl fluoride of Bellen’KilTs [sic] process with methyl chloride with a reasonable expectation.” Appeal Br. 7. Appellants also contend that using methyl chloride in the claimed reaction results in higher selectivity than methyl fluoride. Id. at 8. To support this argument, Appellants provided a publication by Martin that they stated showed “that radicals are more easily generated from CH3F than CH3CI.” Id. Although Appellants did not offer an explanation, we understand Appellants’ argument to be that the production of more free radicals with CH3F results in undesirable side-reactions, and less selectivity as compared to CH3C1 which generates fewer free radicals. However, no evidence or comparative testing was provided to establish that high selectivity was, in fact, observed. An argument made by counsel in a brief does not substitute for evidence lacking in the record. Estee Lauder Inc. v. L’Oreal, S.A., 129 F.3d 588, 595 (Fed. Cir. 1997). 4 Appeal 2016-003002 Application 13/319,588 Reason to combine Appellants also contend that Saunders does not provide motivation to have substituted methyl chloride for the methyl fluoride in Belen’Kill. Reply Br. 4. In making this argument, Appellants cite the statement in Saunders that the reaction of F" in the equations showing the reaction of the halogen ion with antimony pentafluoride is ‘“likely to be more exothermic than that of Cl'.”’ Id. (quoting from Saunders). Appellants provided no explanation, but apparently their argument is that the skilled worker would have believed that the reaction of methyl fluoride is favored because it is more exothermic than methyl chloride. We do not find Appellants’ argument persuasive. The difference between the process of producing a fluorine containing propane as described in Belen’Kill and the claimed process is that in Belen’Kill methyl fluoride is used as a reactant, while in the claimed reaction, methyl chloride is used. The Examiner reasoned that it would have been obvious to have substituted methyl chloride for methyl fluoride because the compounds are chemically similar (namely, they differ only in the choice of Cl or F, and Cl and F are members of the same periodic group and, thus, have similar chemical properties) and because Saunders teaches that methyl fluoride and methyl chloride undergo the same type reaction with antimony pentafluoride, the same catalyst used in Belen’Kill and in the claims. Appellants’ principal argument is that one of ordinary skill in the art would not have expected methyl chloride to work better than methyl fluoride, and thus, there would have been no reason to have substituted methyl chloride in Belen’Kill’s process. 5 Appeal 2016-003002 Application 13/319,588 This argument does not persuade us that the Examiner erred in finding the claimed subject matter obvious. First, the Examiner provided a well-reasoned basis for modifying Belen’Kill. Non-Final Act. 5—6. With respect to the substitution of one halogen for another, it is basic chemical knowledge that elements from the same periodic group have similar chemical properties. See above. It is also well-established that: Structural relationships may provide the requisite motivation or suggestion to modify known compounds to obtain new compounds. For example, a prior art compound may suggest its homologs because homologs often have similar properties and therefore chemists of ordinary skill would ordinarily contemplate making them to try to obtain compounds with improved properties.” In re Dene!, 51 F.3d 1552, 1558 (Fed. Cir. 1995). Appellants contend that one of ordinary' skill in the art would not have substituted methyl chloride for methyl fluoride because they would not have had a reasonable expectation of success that it would work, and because reactions with methyl fluoride are favored. Appellants did not provide adequate evidence that one of ordinary skill in the art at the time of the invention would have expected that methyl chloride would not work in the process of Belen’Kill. Even if we find the evidence cited in Tung and Nappa as probative of bond strength, the fact that the C-F bond is easier to break than the C-Cl bond does not establish a reasonable expectation that the methyl chloride would not work. To the contrary, Saunders showed that both alkyl-CTs and alkyl-F’s reacted with the same antimony pentafluoride catalyst (Saunders 5033 (col 2, beginning at line 15)) in Belen’Kill and in the claimed process, providing an 6 Appeal 2016-003002 Application 13/319,588 expectation of success at the time of the invention that an alkyl chloride would work in the process of Belen’Kill. Appellants responded that Saunders shows that the reaction of alkyl fluorides with antimony pentafluoride is more exothermic than with alkyl chloride (Reply Br. 4), but the fact that the alkyl halides have different reactivties and heats of reaction is not evidence that the skilled worker reading Saunders would have been dissuaded from using methyl chloride in Belen’Kill, particularly when Saunders showed both Cl and F alkyls reacted with antimony pentafluoride. Appellants did not establish what one of ordinary skill in the art would have believed upon reading Saunders. As indicated above, attorney argument is insufficient. (It has not been established the attorney is a person of ordinary skill in the art qualified to testify on this issue.) Moreover, “just because better alternatives exist in the prior art does not mean that an inferior combination is inapt for obviousness purposes.” In re Mouttet, 686 F.3d 1322, 1334 (Fed. Cir. 2012). Appellants also argue that methyl chloride would be more selective in the Belen’Kill process than methyl fluoride. One way for a patent applicant to rebut a prima facie case of obviousness is to make a showing of “unexpected results,” i.e., to show that the claimed invention exhibits some superior property or advantage that a person of ordinary skill in the relevant art would have found surprising or unexpected. In re Soni, 54 F.3d 746, 750 (Fed. Cir. 1995). However, no objective evidence has been provided that methyl chloride is more selective than methyl fluoride and that such selectivity would have been surprising to one of ordinary skill in the art at the time of the invention. 7 Appeal 2016-003002 Application 13/319,588 DECISION For the above-identified reasons, the obviousness rejection of claim 1 is affirmed. Dependent claims 2—6 were not argued separately and fall with claim 1. 37 C.F.R. §41.37(c)(l)(iv). TIME PERIOD No time period for taking any subsequent action in connection with this appeal may be extended under 37 C.F.R. § 1.136(a)(l)(iv). AFFIRMED 8 Copy with citationCopy as parenthetical citation