Gas Phase Rearrangement Patents (Class 540/536)
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Patent number: 5292880Abstract: A process for catalytically converting cyclohexanone oxime to epsilon caprolactam. The conversion catalyst is a crystalline aluminosilicate zeolite having a Constraint Index greater than 1 and a reduced surface acidity. The surface acidity is reduced by selective surface dealumination of the crystalline aluminosilicate zeolite by contacting the zeolite with dicarboxylic acid, such as oxalic acid.Type: GrantFiled: March 12, 1993Date of Patent: March 8, 1994Assignee: Mobil Oil CorporationInventors: Minas R. Apelian, Weldon K. Bell, Anthony S. Fung, Werner O. Haag, Chaya Venkat
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Patent number: 5227482Abstract: A method for preparing a lactam, which comprises subjecting a cycloalkanone oxime to a Beckmann rearrangement reaction in a gas phase in the presence of a carrier-supported catalyst containing tantalum, wherein the carrier-supported catalyst is the one prepared by contacting an organic compound containing tantalum to a silica carrier having pores with pore diameters of from to 150,000 .ANG. wherein the pore volume of pores with pore diameters of from 40 to 2,000 .ANG. is at least 80% of the total pore volume of pores with pore diameters of from 40 to 150,000 .ANG..Type: GrantFiled: April 17, 1992Date of Patent: July 13, 1993Assignee: Mitsubishi Kasei CorporationInventor: Takashi Ushikubo
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Patent number: 5212302Abstract: In the production of .epsilon.-caprolactam from cyclohexanon oxime in gaseous phase in the presence of solid catalysts, the catalysts, no matter whether they may have worked, are brought into contact with either aqueous solution of ammonium salts and at least one basic material or ammonia water.Type: GrantFiled: December 23, 1991Date of Patent: May 18, 1993Assignee: Sumitomo Chemical Company, Ltd.Inventors: Masaru Kitamura, Hiroshi Ichihashi, Hideto Tojima
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Patent number: 5071802Abstract: Carbonaceous materials deposited on solid catalysts and produced, for example, in Beckmann rearrangement in a gaseous phase are burned off by effecting the treatment in the presence of alcohols such as methanol or ethanol together with molecular oxygen-containing gas in order to regenerate the catalyst activity.Type: GrantFiled: March 7, 1990Date of Patent: December 10, 1991Assignee: Sumitomo Chemical Co., Ltd.Inventors: Shinkichi Shimizu, Takayasu Niwa, Nobuyuki Abe, Masanori Doba, Akira Iguchi, Hiroshi Ichihashi, Masaru Kitamura
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Patent number: 4968793Abstract: .epsilon.-caprolactam is produced by gas phase reaction of cyclohexanone oxime using a solid acid as a catalyst in the presence of a compound represented by the formula (I): R.sub.1 --O--R.sub.2 (wherein R.sub.1 represents a lower alkyl group which may be substituted with a fluorine atom and R.sub.2 represents a hydrogen atom, a lower alkyl group or a phenyl group) such as a lower alcohol or an ether compound. The solid acid includes a crystalline metallosilicate or a crystalline silicate.Type: GrantFiled: January 23, 1990Date of Patent: November 6, 1990Assignee: Sumitomo Chemical Company, LimitedInventors: Masaru Kitamura, Hiroshi Ichihashi, Gohfu Suzukamo, Yasuo Nakamura
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Patent number: 4965371Abstract: This invention provides a process for preparing lactams, by selectively reacting a novel 1-hydrocarbylamino (or heteroatom-substituted hydrocarbylamino); 1,1-dicarboxylic acid, alkylesters; 1-hydrocarbyl (or heteroatom-substituted hydrocarbyl) carboxylic acid, alkyl ester methane, as the salt of an acid having a pKa of 0 or more, in the absence or presence of a base, whereby novel lactams wherein one or both hydrocarbyl moieties are incorporated into the lactam ring are obtained. That is, the acid moiety of said novel salt promotes the reaction whereby both hydrocarbyl moieties are incorporated into the ring, while the presence of a base, in an amount substantially equivalent to said acid promotes the reaction whereby only one hydrocarbyl is incorporated into the ring.Type: GrantFiled: May 25, 1989Date of Patent: October 23, 1990Assignee: Whitby Research, Inc.Inventors: Gevork Minaskanian, James V. Peck
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Patent number: 4927924Abstract: A process is provided for catalytically converting cyclohexanone oxime to epsilon caprolactam. The conversion is characterized by exceptionally high selectivity and reduced rate of catalyst aging, even at single pass conversion above 90 percent. The conversion catalyst is a medium pore size crystalline zeolite exemplified by ZSM-5 which has low acid activity. Recycling unconverted oxime provides excellent ultimate yield of caprolactam.Type: GrantFiled: April 14, 1989Date of Patent: May 22, 1990Assignee: Mobil Oil Corp.Inventors: Weldon K. Bell, Werner O. Haag
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Patent number: 4883915Abstract: A process for the catalyzed conversion fo oximes such as cyclohexanone oxime to amides such as caprolactam via a high conversion, high selectivity, long catalyst lifetime reaction over a HAMS-1B crystalline borosilicate-based catalyst composition.Type: GrantFiled: April 8, 1987Date of Patent: November 28, 1989Assignee: Amoco CorporationInventor: Patrick E. McMahon
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Patent number: 4873325Abstract: Oximes can be converted to the corresponding amides by contacting the oximes with a non-zeolitic molecular sieve, which has in its calcined form an adsorption of isobutane of at least about 2 percent by weight of the non-zeolitic molecular sieve at a partial pressure of 500 torr and a temperature of 20.degree. C. The process is especially useful for the conversion of cyclohexanone oxime to caprolactam. The non-zeolitic molecular sieves can achieve improved conversion rates and selectivities as compared with conventional zeolite catalysts for the reaction.Type: GrantFiled: June 25, 1986Date of Patent: October 10, 1989Assignee: UOPInventor: Kurt D. Olson
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Patent number: 4717769Abstract: .epsilon.-caprolactam is produced by gas phase catalytic synthesis with high selectivity of lactam wherein cyclohexanone oxime is brought into contact with a crystalline metallo-silicate catalyst having Si/metal atomic ratio is more than 500. The metal moiety in the catalyst is Ga, Fe, B, Zr, Bi, Nb, Zn, Be, Cr, La, Ti, Hf, V and/or Cu.Type: GrantFiled: February 27, 1987Date of Patent: January 5, 1988Assignee: Sumitomo Chemical Co., Ltd.Inventors: Hiroshi Sato, Kenichi Hirose, Masaru Kitamura, Youichi Umada, Norio Ishii, Hideto Tojima
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Patent number: 4717770Abstract: .epsilon.-caprolactam is prepared by gas phase catalytic synthesis where cyclohexanone oxime is brought into contact with a crystalline zeolite, for example, aluminosilicate zeolite or metallosilicate zeolite having a constraint index of 1-12 which has been surface treated with an organometallic compound represented by the general formula: R.sub.4-n MX.sub.n wherein R which may be identical or different represent an alkyl group of 1-6 carbon atoms or phenyl group, M represnets Si or Ge, X represents Cl or an alkoxy group of 1-6 carbon atoms and n represents 1 or 2.Type: GrantFiled: February 27, 1987Date of Patent: January 5, 1988Assignee: Sumitomo Chemical Co., Ltd.Inventors: Hiroshi Sato, Kenichi Hirose, Masaru Kitamura, Hideto Tojima, Norio Ishii
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Patent number: 4709024Abstract: .epsilon.-caprolactam is prepared by gas phase catalytic synthesis in which cyclohexanone oxime is brought into contact with crystalline alluminosilicate, for example, ZSM-5 H.sup.+ form) having 1-12 of constraint index, 500 or more, preferably 1000 or more, of Si/Al atomic ratio and 5.mu. equivalent/g or less, preferably 2.mu. equivalent/g, of external acid amount.Type: GrantFiled: August 13, 1986Date of Patent: November 24, 1987Assignee: Sumitomo Chemical CompanyInventors: Hiroshi Sato, Kenichi Hirose, Norio Ishii, Youichi Umada
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Patent number: 4697010Abstract: A process for the catalyzed conversion of oximes such as cyclohexanone oxime to amides such as caprolactam via a high conversion, high selectivity, long catalyst lifetime reaction over a HAMS-1B crystalline borosilicate-based catalyst composition.Type: GrantFiled: June 5, 1986Date of Patent: September 29, 1987Assignee: Amoco CorporationInventor: Patrick E. McMahon