Ex Parte EngDownload PDFPatent Trial and Appeal BoardOct 31, 201311927834 (P.T.A.B. Oct. 31, 2013) Copy Citation UNITED STATES PATENT AND TRADEMARKOFFICE 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. 11/927,834 10/30/2007 Curtis N. Eng 07-09 6532 7590 11/01/2013 Christian N. Heausler Kellogg Brown & Root LLC 601 Jefferson Avenue Houston, TX 77002 EXAMINER BULLOCK, IN SUK C ART UNIT PAPER NUMBER 1772 MAIL DATE DELIVERY MODE 11/01/2013 PAPER 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. PTOL-90A (Rev. 04/07) UNITED STATES PATENT AND TRADEMARK OFFICE _________ BEFORE THE PATENT TRIAL AND APPEAL BOARD __________ Ex parte CURTIS N. ENG __________ Appeal 2012-007962 Application 11/927,834 Technology Center 1700 ___________ Before ADRIENE LEPIANE HANLON, GEORGE C. BEST, and DONNA M. PRAISS, Administrative Patent Judges. HANLON, Administrative Patent Judge. DECISION ON APPEAL Appeal 2012-007962 Application 11/927,834 2 A. STATEMENT OF THE CASE The Appellant has filed an appeal under 35 U.S.C. § 134 from an Examiner’s decision finally rejecting claims 1-18 and 26-31. We have jurisdiction under 35 U.S.C. § 6(b). We REVERSE and enter new grounds of rejection. The subject matter on appeal is directed to a process for making propylene comprising, inter alia, bypassing a first product around an existing etherification reactor for converting isobutylene to methyl tert-butyl ether (MTBE). According to the Appellant’s Specification: MTBE production has decreased as various jurisdictions restricted or banned its use. By late 2006 most American gasoline retailers stopped using MTBE as an oxygenate. Accordingly, domestic production has continued to decline. As a result, MTBE manufacturers are left holding useless feedstocks and manufacturing assets. There is a need, therefore, for reallocating feedstocks and manufacturing assets previously allocated to the manufacture of MTBE, thereby providing an economic benefit to MTBE manufacturers. Spec., ¶¶ [0003]-[0004]. The Appellant’s process reallocates MTBE feedstocks and manufacturing assets to produce olefins such as propylene. Spec., ¶ [0010]. Representative claim 1 is reproduced below from the Claims Appendix of the Appeal Brief dated January 17, 2012 (“App. Br.”). Appeal 2012-007962 Application 11/927,834 3 1. A process for making propylene, comprising: [1] dehydrogenating a feed comprising one or more C4- containing compounds to provide a first product comprising about 20 vol% to about 80 vol% isobutylene; [2] bypassing the first product comprising about 20 vol% to about 80 vol% isobutylene around an existing etherification reactor for converting isobutylene to methyl tert-butyl ether; and [3] cracking at least a portion of the first product comprising about 20 vol% to about 80 vol% isobutylene to provide a second product comprising propylene, ethylene, and butane, wherein cracking comprises contacting the first product with a catalyst consisting essentially of a zeolite at reaction conditions favoring conversion of the first product to propylene. The claims stand rejected as follows:1 (1) claims 1-18, 26, 27, and 29-31 under 35 U.S.C. § 103(a) as unpatentable over Leyshon (U.S. 5,043,522 issued Aug. 27, 1991) in view of Hensley (U.S. 5,254,748 issued Oct. 19, 1993) and Tsunoda (U.S. 6,307,117 B1 issued Oct. 23, 2001);2 and (2) claim 28 under 35 U.S.C. § 103(a) as unpatentable over Leyshon in view of Hensley, Tsunoda, and Miracca (U.S. 5,446,224 issued Aug. 29, 1995). The Appellant presents separate arguments for claims 1 and 29 in the Appeal Brief. 1 In the Examiner’s Answer dated February 24, 2012 (“Ans.”), at 18, the Examiner withdrew the obviousness-type double patenting rejection of claims 1-18 and 26- 31 as unpatentable over claims 1-12 and 23-30 of Application 11/927,828. 2 Claim 31 was not included in the statement of the rejection in the Final Office Action dated August 2, 2011 (“Final”), at 2. However, the Examiner discusses claim 31 in the body of the rejection. Final 6. For the reasons set forth infra, this rejection is not sustained. Thus, it is not necessary to determine whether the Examiner’s error was harmful. Appeal 2012-007962 Application 11/927,834 4 B. EXAMINER’S REJECTIONS UNDER 35 U.S.C. § 103(a) The Examiner finds Leyshon discloses a process for producing propylene comprising the step of dehydrogenating a feed comprising C4+ products. The Examiner finds Leyshon does not disclose the bypassing and cracking steps recited in claim 1. Ans. 4-5. The Examiner finds Hensley discloses a process which integrates dehydrogenating C4 compounds with a MTBE unit and concludes that it would have been obvious to combine the dehydrogenation reactor of Leyshon with the MTBE unit disclosed in Hensley and “make an integrated process of dehydrogenation and etherification.” Id. at 5. As for the cracking step, the Examiner finds Tsunoda discloses a method of producing ethylene, propylene, and butane by direct cracking of C4+ olefins. Id. The Examiner finds “ethylene and propylene are important raw materials for a variety of products.” Id. at 6. Thus, the Examiner concludes it would have been obvious to one of ordinary skill in the art to introduce an olefin cracking step in the modified Leyshon process to produce ethylene and propylene “when MTBE is not a desired product” thereby bypassing the MTBE unit disclosed in Hensley. Id. The Appellant argues that “[n]othing about Hensley motivates or suggests bypassing its etherification unit because the etherification unit is a key component of Hensley’s ‘essential feature.’” App. Br. 11. The Appellant’s argument is supported by the record. See Hensley, col. 3, ll. 24-28 (“An essential feature of all the disclosed embodiments of the present invention is directed to integrating a combination hydrogenation/dehydrogenation step . . . into an etherification process.”). Thus, absent the Appellant’s disclosure, there would have been no reason to bypass the MTBE reactor disclosed in Hensley and introduce an olefin Appeal 2012-007962 Application 11/927,834 5 cracking step as proposed by the Examiner. For this reason, the § 103(a) rejection based on Leyshon in view of Hensley and Tsunoda is not sustained. The Examiner does not rely on Miracca to overcome the above-noted deficiency in Hensley. Therefore, the § 103(a) rejection based on Leyshon in view of Hensley, Tsunoda, and Miracca is not sustained. C. NEW GROUNDS OF REJECTION Claims 1-18, 26, 27, and 29-31 are rejected under 35 U.S.C. § 103(a) as unpatentable over the combination of Tsunoda, Hensley, and paragraphs [0003] and [0004] of the Appellant’s Specification. 1. Claim 1 There is no dispute on this record that Tsunoda discloses a method of producing ethylene, propylene, and butane by cracking C4+ olefins. Ans. 5; see also Tsunoda, col. 12, ll. 14-15 (ethylene and propylene are collected from the obtained H2-C3 fraction); Tsunoda, col. 12, ll. 38-48 (butane is separated by the C4 separator). In one embodiment, Tsunoda discloses that the hydrocarbon feedstock is a C4 fraction comprised mainly of C4 hydrocarbons, such as butane, isobutane, butene, and isobutene. Tsunoda, col. 11, ll. 61-67. Thus, we find Tsunoda discloses step [3] of the claimed process. As for step [1] of the claimed process, Hensley discloses a method of producing tertiary alkyl ether compounds, such as MTBE, from a mixture of C4 hydrocarbons. Hensley, col. 4, ll. 51-55. According to one embodiment of the invention, a mixed C4 hydrocarbon feed stream is provided to a hydrogenation/dehydrogenation unit along with an isobutane stream from an isomerization unit. Id. at col. 5, ll. 56-62. Hensley discloses that the reaction product from the hydrogenation/de-hydrogenation unit comprises primarily Appeal 2012-007962 Application 11/927,834 6 isobutene but also contains significant amounts of butene-1, butene-2, n-butane, and isobutane. Id. at col. 4, l. 67-col. 5, l. 2 and col. 5, ll. 52-54. The reaction product from the hydrogenation/dehydrogenation unit of Hensley is substantially the same as the hydrocarbon feedstock used in the method of Tsunoda. Thus, we find one of ordinary skill in the art would have considered Hensley’s reaction product to be a suitable feedstock in Tsunoda’s method. As for step [2] of the claimed process, Hensley discloses that the reaction product from the hydrogenation/dehydrogenation unit feeds a distillation column, and the overhead from the distillation unit is fed to a MTBE unit. Id. at col. 5, l. 63-col. 6, l. 2. The Appellant discloses that MTBE production was on the decline at the time of the Appellant’s invention and “MTBE manufacturers are left holding useless feedstocks and manufacturing assets.” Spec., ¶ [0003]. Thus, according to the Appellant, “[t]here is a need . . . for reallocating feedstocks and manufacturing assets previously allocated to the manufacture of MTBE, thereby providing an economic benefit to MTBE manufacturers.” Id. at ¶ [0004]. Based on this disclosure in the Appellant’s Specification, we find one of ordinary skill in the art would have been motivated to reallocate Hensley’s MTBE feedstocks and manufacturing assets (i.e., Hensley’s hydrogenation/de- hydrogenation unit) to produce the feedstock in Tsunoda’s method. This combination results in step [2] of the claimed process (i.e., bypassing Hensley’s reaction product from the hydrogenation/dehydrogenation unit around an existing etherification reactor). Thus, we conclude the process of claim 1 is rendered obvious by the combination of Tsunoda, Hensley, and paragraphs [0003] and [0004] of the Appellant’s Specification. Appeal 2012-007962 Application 11/927,834 7 2. Claim 29 Claim 29 recites, inter alia, that “the feed further comprises about 70% vol or more isobutane and about 5% vol to about 30% vol butane.” App. Br., Claims App’x. The Appellant argues Leyshon does not “teach, show, or suggest a feed comprising about 70% vol or more isobutane and about 5% vol to about 30% vol butane, as required in claim 29.” Id. at 15. We find Hensley teaches that the concentration of isobutane in the feed stream is a result effective variable. Hensley, col. 4, ll. 51-59; see also In re Boesch, 617 F.2d 272, 276 (CCPA 1980) (“discovery of an optimum value of a result effective variable in a known process is ordinarily within the skill of the art”). Thus, the burden shifts to the Appellant to demonstrate that a feed comprising “about 70% vol or more isobutane” achieves unexpectedly good results. See In re Antonie, 559 F.2d 618, 620 (CCPA 1977) (a prima facie case of obviousness may be rebutted “where the results of optimizing a variable, which was known to be result effective, [are] unexpectedly good”). The Appellant has not made such a showing on this record. As for the concentration of butane in Hensley’s feed, we find the feeds employed by the Appellant and Hensley are both used for manufacturing MTBE. Thus, it is reasonable to expect that the feeds would have similar butane concentrations. In this regard, we note the Appellant does not disclose that the butane concentration is critical and indicates that as little as about 1% vol butane may be contained in the feedstock. Spec., ¶ [0016]. Based on the foregoing, the weight of the evidence supports a conclusion of obviousness under § 103(a). Appeal 2012-007962 Application 11/927,834 8 Claim 28 is rejected under 35 U.S.C. § 103(a) as unpatentable over the combination of Tsunoda, Hensley, paragraphs [0003] and [0004] of the Appellant’s Specification, and Miracca. Claim 28 is reproduced below from the Claims Appendix of the Appeal Brief. 28. The process of claim 1, wherein the first product further comprises isobutane, hydrogen, and C1 to C3 hydrocarbons, and the process further comprises: contacting at least a portion of the first product with a solvent to provide a solvent mixture; separating the solvent mixture to produce a purified isobutane/isobutylene mixture, wherein the purified isobutane/isobutylene mixture contains less hydrogen and C1 to C3 hydrocarbons than the first product, and wherein at least a portion of the purified isobutane/isobutylene mixture is cracked to provide the second product. The Examiner found Miracca discloses an integrated process for producing isobutene and alkyl tert-butyl ethers similar to Hensley. The Examiner continues: Miracca also discloses separation of first product including hydrogen, light hydrocarbons, and C4 hydrocarbons (See column 1, lines 59-61). Miracca further discloses separation and purification of C4 hydrocarbons using a suitable solvent followed by C4 stripping and solvent regeneration (See column 1, lines 65-68). Miracca also discloses separation and purification of isobutene/isobutane fraction (See column 2, lines 18-26). In view of Miracca disclosing separation and purification of isobutene/isobutane fraction, and Tsunoda disclosing that when olefin content of hydrocarbon feedstock is less than 20%, the yields of ethylene and propylene are unsatisfactory (See column 6, lines 32-34), it would have been obvious to one with ordinary skill in the art at the time of invention to combine Leyshon/Hensley/Tsunoda invention with Miracca invention and use the isobutene/isobutane fraction from Appeal 2012-007962 Application 11/927,834 9 Miracca in the cracking step of Tsunoda for an increased ethylene/propylene production. Ans. 11. The Appellant does not direct us to any evidence to the contrary. We find the benefits achieved in the modified Leyshon process with the addition of Miracca (i.e., increased ethylene/propylene production) would have been equally desirable in the modified Tsunoda process. For this reason, we conclude the process of claim 28 is rendered obvious by the combination of Tsunoda, Hensley, paragraphs [0003] and [0004] of the Appellant’s Specification, and Miracca. D. DECISION The Examiner’s rejection of claims 1-18, 26, 27, and 29-31 under 35 U.S.C. § 103(a) as unpatentable over Leyshon in view of Hensley and Tsunoda is reversed. The Examiner’s rejection of claim 28 under 35 U.S.C. § 103(a) as unpatentable over Leyshon in view of Hensley, Tsunoda, and Miracca is reversed. Claims 1-18, 26, 27, and 29-31 are rejected under 35 U.S.C. § 103(a) as unpatentable over the combination of Tsunoda, Hensley, and paragraphs [0003] and [0004] of the Appellant’s Specification. Claim 28 is rejected under 35 U.S.C. § 103(a) as unpatentable over the combination of Tsunoda, Hensley, paragraphs [0003] and [0004] of the Appellant’s Specification, and Miracca. This decision contains new grounds of rejection under 37 C.F.R. § 41.50(b) which provides that “[a] new ground of rejection . . . shall not be considered final for judicial review.” Appeal 2012-007962 Application 11/927,834 10 37 C.F.R. § 41.50(b) also provides that the Appellant, WITHIN TWO MONTHS FROM THE DATE OF THE DECISION, must exercise one of the following two options with respect to the new grounds of rejection to avoid termination of the appeal as to the rejected claims: (1) Reopen prosecution. Submit an appropriate amendment of the claims so rejected or new evidence relating to the claims so rejected, or both, and have the matter reconsidered by the examiner, in which event the proceeding will be remanded to the examiner. . . . (2) Request rehearing. Request that the proceeding be reheard under § 41.52 by the Board upon the same record. . . . No time period for taking any subsequent action in connection with this appeal may be extended under 37 C.F.R. § 1.136(a). REVERSED (37 C.F.R. § 41.50(b)) bar Copy with citationCopy as parenthetical citation