Ex Parte Sommer et alDownload PDFPatent Trial and Appeal BoardMay 31, 201612814536 (P.T.A.B. May. 31, 2016) Copy Citation UNITED STA TES p A TENT AND TRADEMARK OFFICE APPLICATION NO. FILING DATE 12/814,536 06/14/2010 157 7590 06/02/2016 Covestro LLC 1 Covestro Circle PITTSBURGH, PA 15205 FIRST NAMED INVENTOR KnutSommer 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 ATTORNEY DOCKET NO. CONFIRMATION NO. BMS091129 9557 EXAMINER OTTON, ALICIA L ART UNIT PAPER NUMBER 1626 NOTIFICATION DATE DELIVERY MODE 06/02/2016 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): veronica. thompson@covestro.com US-IPR@covestro.com laura.finnell@covestro.com PTOL-90A (Rev. 04/07) UNITED STATES PATENT AND TRADEMARK OFFICE BEFORE THE PATENT TRIAL AND APPEAL BOARD Ex parte KNUT SOMMER, DR. PETER LEHNER, and ANDRE LAGO Appeal2014-005103 Application 12/814,536 Technology Center 1600 Before DONALD E. ADAMS, RICHARD M. LEBOVITZ, and JEFFREY N. FREDMAN, Administrative Patent Judges. LEBOVITZ, Administrative Patent Judge. DECISION ON APPEAL This appeal involves claims directed to a process for production of an aromatic amine. Appellants appeal from the Examiner's final rejection of claims 1-18 as obvious under 35 U.S.C. § 103(a). We have jurisdiction under 35 U.S.C. § 134. The rejection is affirmed. STATEMENT OF CASE Claims 1-181 stand finally rejected by the Examiner under 35 U.S.C. 103(a) (pre-AIA) as obvious in view of JP '405 (English translation of JP 1 Page 1 of the Appeal Brief lists the rejected claims correctly as 1-18. However, page 2 lists claims 1-9 and 10-19. The claims in the claim Appeal2014-005103 Application 13/814,536 2007-217405, published Feb. 2, 2010). Final Rej. 5. The Examiner had also rejected the claims as anticipated by JP '405, but the rejection was withdrawn. Answer 7. Claim 1 is representative and reads as follows; 1. Process for the production of an aromatic amine comprising a) removing water formed during hydrogenation of a nitroaromatic compound by phase separation to obtain a crude aromatic amine, and b) purifying the crude aromatic amine, optionally, by distillation before treatment by a procedure comprising: b) (i) mixing the crude aromatic amine with at least one aqueous solution of at least one base in an amount and in a concentration such that (A) a molar ratio of total amount of any base added to the aromatic amine in purifying the crude aromatic amine to amount of phenolic hydroxyl groups contained in the crude aromatic amine from a) not greater than 10 is achieved, and (B) a weight ratio of organic constituents to water greater than l 0 is achieved, b) (ii) mixing the mixture obtained from b) (i) with water in an amount such that a weight ratio of the mixture obtained from step b) (i) to the water added in step b) (ii) between 0.05 and 20 is achieved, and b) (iii) separating the mixture obtained from b) (ii) into an organic phase containing the aromatic amine and an aqueous phase. appendix only go up to claim 18 and claim 10 is rejected. Consequently, we presume the latter statement of the claims is an error. 2 Appeal2014-005103 Application 13/814,536 Rejection Claim 1 is directed to a process for the production of an aromatic amine. The process comprises two steps, a) and b ). Step b) is divided into three steps: b) (i), b) (ii), and b) (iii). In step b) (i), crude aromatic oil is mixed with an aqueous solution of at least one base. In step b) (ii), the mixture ofb) (i) is mixed with water. In step b) (iii), the mixture obtained from b) (ii) is separated into an organic phase containing the aromatic amine and an aqueous phase. Specific ratios of the constituents recited in claim 1 are recited in the claims. These are as follows: 1) base to phenolic hydroxyl groups in the crude aromatic amine is not greater than 10 in step b) (i); 2) organic constituents to water greater than 10 in step b) (i); and 3) mixture of b) (i) to water in step b) (ii) is between 0.5 and 20. The Examiner found that JP '405 describes all the steps of the claimed method. Final Rej. 5-7. For ratio 1), citing paragraph 15, the Examiner found that JP '405 teaches that the "molar ratio of alkali to phenols should be from 3 to 500, preferably 10-200 and most preferably 5-100," and that the ratio is a result- effective variable. Id. at 6. The Examiner also found that, in Example 3, the ratio of base: phenolic hydroxyl group was 5.35 which is not greater than 10. Id. at 6-7. The Examiner stated it was routine at the time of the invention to determine the optimal ratio of a known result-effective variable. Id. at 8. For ratio 2), the Examiner calculated a ratio of 282.9 in Example 3, which the Examiner found is greater than 10 as required by the claim. Final Rej. 7. 3 Appeal2014-005103 Application 13/814,536 For ratio 3), the Examiner calculated a weight ratio of 2.6 in Example 3, which the Examiner found falls between 0.5 and 20 as recited in claim 1. Id. The Examiner found that JP '405 differs from the claims in that JP '405 teaches adding water before the aqueous alkaline solution rather than after as required by step b) (ii) of claim 1. Id. at 7-8. However, the Examiner found that it would have been obvious to have added the water after the alkaline solution because the end mixture would have been same and because water is added in a second step by JP '405 when it is added as part of the aqueous alkaline solution. Id. at 8. Appellants contend that JP '405 does not teach or suggest the three required ratios. Appeal Br. 5. Discussion During patent examination, the Examiner bears the initial burden of establishing a prima facie case of obviousness. In re Kumar, 418 F.3d 1361, 1366 (Fed. Cir. 2005). In this case, the Examiner identified factual support for each of the ratios recited in independent claim 1. Final Rej. 6-8. Appellants contend that ratios 1 ), 2), and 3) are not taught or suggested by JP '405, but provided arguments only for ratio 1 ). Appeal Br. 5. With respect to ratio 1 ), Appellants contend that JP '405 teaches treating the crude aromatic amine ("crude aniline" in JP '405) twice with a sodium hydroxide solution (the "base" of claim 1 ). Id. at 5. Consequently, Appellants contend that the molar ratio of sodium hydroxide to phenolic hydroxyl groups is 10. 7 in JP '405 which is outside the claimed ratio of "not 4 Appeal2014-005103 Application 13/814,536 greater than 10." Id. Appellants also argue that JP '405 teaches the "adverse effects of varying the amount of water." Id. The Examiner responded that the claimed process is recited with the term "comprising" which is "open transitional language" that permits additional steps. Answer 8. Thus, the Examiner found, even if JP '405 describes adding a second aliquot of base in a later step, the first addition of base with a molar ratio of 5.35 meets the claimed requirement of a ratio that does not exceed 10. Id. at 8-9. The Examiner also pointed out that dependent claim 2 recites an additional step of adding base, consistent with reading claim 1 to permit the addition of another aliquot of base. Id. The Examiner further responded that paragraph 15 of JP '404 teaches a range of preferred molar ratios, most preferably from 5-100, which overlaps with the claimed range of "not greater than 10." Id. at 9. The Examiner stated that despite Appellants' argument that there is an adverse effect of varying the amounts of water and base, an adverse effect would not be expected in the range 5-100 because that range is expressly described as "most preferable" by JP '405. Id. at 9. The Examiner's positions is supported by a preponderance of the evidence. As the Examiner explained, claim 1 is open-ended so the first addition of base in a molar ratio of 5.35 described in JP '405 meets the claimed requirement of 1) a ratio of not greater than 10. Even if the example in JP '405 teaches a ratio that is greater than 10, JP '405 suggests a lower ratio. As pointed out by the Examiner, a ratio of 5- 100 is preferable. JP '405 i-f 15. While Appellants contend that varying the ratio is described by JP '405 as having adverse effects, we find no evidence that ratio of 5-100 would be adverse because it is expressly described by JP 5 Appeal2014-005103 Application 13/814,536 '405 as preferred ratio. The preferred ratio of JP '405 of 5-100 overlaps with the recited ratio of "not greater than 10." When there is a range disclosed in the prior art, and the claimed invention overlaps or falls within that range, there is a presumption of obviousness. In re Peterson, 315 F.3d 1325, 1329 (Fed. Cir. 2003); Iron Grip Barbell Co. v. USA Sports, Inc., 392 F.3d 1317, 1322 (Fed. Cir. 2004). Thus, the Examiner properly found the claimed range to be obvious. In such situations, "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. In re Woodruff, 919 F.2d 1575, 1578 (Fed. Cir. 1990). Appellants have not provided evidence that the claimed ratio is critical or achieves unexpected results. Consequently, we affirm the rejection of claim 1 as obvious in view of JP '405. Claims 2-18 were not argued separately and thus fall with claim 1. 37 C.F.R. i-f 41.37(c)(iv). AFFIRMED 6 Copy with citationCopy as parenthetical citation