Preparing By Isomerization Patents (Class 568/783)
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Patent number: 11485694Abstract: Processes of producing cresols from a phenols containing feed are described. The processes involve a combination of dealkylation and transalkylation processes. The dealkylation process converts the heavy alkylphenols in an alkylphenols stream to phenol and olefins. The olefins produced in the dealkylation process are separated out. The methylphenols, which are not converted in the dealkylation process, and phenol react in the transalkylation process to generate cresols.Type: GrantFiled: February 4, 2019Date of Patent: November 1, 2022Assignees: China Petroleum & Chemical Corporation, UOP LLCInventors: Shuguang Zhang, Lubo Zhou
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Patent number: 6887820Abstract: A method for producing optically active compounds is disclosed. The method is highly practical for producing optically active compounds useful for various utilities such as intermediates for synthesizing pharmaceutical agents, liquid crystal materials and agents for optical resolution.Type: GrantFiled: September 14, 2000Date of Patent: May 3, 2005Assignees: Japan Science and Technology Corporation, NKK Corporation, Takeda Pharmaceutical Company Limited, Asahi Kasei Pharma Corporation, Takasago International CorporationInventors: Takao Ikariya, Shohei Hashiguchi, Jun Takehara, Nobuyuki Uematsu, Kazuhiko Matsumura, Ryoji Noyori, Akio Fujii
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Patent number: 6433236Abstract: A substituted diaryl compound or a mixture of substituted diaryl compounds, such as dimethylbiaryl compounds are isomerized by treatment with a strong acid or mixtures of strong acids in the absence of any additional catalyst. The strong acid or mixture of acids has a Hammett acidity of less than about −12.6. The isomerization reaction conditions such as reaction temperature, amount of acid, and amount of solvent can be adjusted to selectively produce desired isomers in high yields. One or more desired isomers may be produced in high yields by isomerization of substituted diaryl compounds and selectively removing one or more desired isomers from the resulting equilibrium mixture of isomers. The isomer mixture may be re-isomerized subsequent to selective removal of the desired isomer to produce additional amounts of desired isomer.Type: GrantFiled: March 21, 2000Date of Patent: August 13, 2002Assignee: Arteva North America S.A.R.L.Inventors: David Anthony Schiraldi, Alexei Viktorovich Iretski, Sheldon Christopher Sherman, Laren Malcolm Tolbert, Mark Gilmore White
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Publication number: 20020040169Abstract: The isomerization of an alkylated phenol composition that contains an ortho-alkyl substituted phenol component to isomerize and reduce the level of ortho-alkyl substituted phenol component therein can be accomplished by heating that composition in the presence of a catalytically effective amount of a solid acid catalyst to carry out such isomerization and reduction in the level of ortho-alkyl substituted phenol. Examples of suitable solid acid catalysts can be selected from the H-form zeolites, the supported sulfonic acids, and the heteropoly acids. The resulting isomerized product can be subsequently phosphorylated.Type: ApplicationFiled: April 26, 2001Publication date: April 4, 2002Inventors: Anantha N. Desikan, George E. Whitwell
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Patent number: 5399786Abstract: The present invention has as purpose a process for the manufacture of tert-butylphenols, mainly of tertbutyl-4-phenols from a phenol and an alkyltert-butylether. The improvement consists in separating in at least two steps, the reaction of phenol alkylation and transalkylation/isomerization of undesirable alkyltert-butylphenols, enabling the flexibilization of the type and quality of end product, and easily adapt to the demands of the market, plus the fact that the total yield improved as well as this improvement has good industrial hygiene properties.Tert-butylphenols are useful intermediate products is the manufacture of phenolic resins or antioxydizing agents for rubber and for several plastic substances.Type: GrantFiled: July 13, 1993Date of Patent: March 21, 1995Assignee: Rhodia S/AInventors: Antonio U. B. Queiroz, Lumi T. Aikawa, deceased
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Patent number: 5053558Abstract: An improved process is disclosed for the isomerization of a non-equilibrium mixture of cresols to achieve a high yield of one or more cresol isomers using a catalyst comprising a Group VIII metal, a modifier, a pentasil zeolite, and an inorganic oxide binder.Type: GrantFiled: July 3, 1990Date of Patent: October 1, 1991Assignee: UOPInventors: J. W. Adriaan Sachtler, R. Joe Lawson
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Patent number: 5015785Abstract: A process for the preparation of mixtures of isomeric cresols with a molar ratio of para- to meta-cresol of from 0.6:1 to 10:1 by isomerization of cresol mixtures or ortho- and/or metal-cresol on zeolite catalysts of the pentasil type in the gas phase at from 300.degree. to 600.degree. C. under from 0.01 to 50 bar entails the mean particle size of the zeolite catalyst being at leat 3 .mu.m, and the selectivity in the established test for the disproportionation of ethylbenzene to diethylbenzene isomers being at least 60% for para-diethylbenzene.Type: GrantFiled: August 8, 1990Date of Patent: May 14, 1991Assignee: BASF AktiengesellschaftInventors: Werner Steck, Helmut Lermer, Matthias Schwarzmann, Toni Dockner
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Patent number: 5015784Abstract: This invention relates to a process for the preparation of bisphenols and bisphenol mixtures by the isomerization of bisphenols on acid or alkaline catalysts in the presence of the corresponding phenols.Type: GrantFiled: August 3, 1989Date of Patent: May 14, 1991Assignee: Bayer AktiengesellschaftInventors: Udo Rudolph, Claus Wulff
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Patent number: 4709102Abstract: The production of a 2-lower alkyl phenol, e.g., 2-cresol or 2-ethylphenol, is carried out by transalkylation of a lower alkyl phenyl ether, e.g. anisole or phenetole, at an elevated temperature in the presence of a medium pore, pentasil-type molecular sieve, e.g. an H-ZSM-5 zeolite, a silicalite or an AMS-1B borosilicate, as catalyst.Type: GrantFiled: October 7, 1986Date of Patent: November 24, 1987Assignee: Celanese CorporationInventor: Balaram B. G. Gupta
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Patent number: 4691063Abstract: An improvement in a process for the isomerization of cresols may be obtained by effecting the isomerization reaction of a cresol in the presence of a phosphorous containing crystalline aluminosilicate zeolite catalyst. The added phosphorous provides stability and longer life to the catalyst as well as more stable selectivity to the desired isomers. The isomerization reaction is effected at temperatures ranging from about 350.degree. C. to about 500.degree. C., pressures ranging from about 1 to about 60 atmospheres, a Liquid Hourly Space Velocity that ranges from 1 to about 5 hours.sup.-1, with the abovementioned catalyst containing from about 1% to about 8% by weight phosphorous.Type: GrantFiled: June 16, 1986Date of Patent: September 1, 1987Assignee: UOP Inc.Inventors: Dusan J. Engel, Jean-Pierre Gilson
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Patent number: 4605790Abstract: Phenol is prepared from mixed phenols derived from coal or biomass by separation of the mixed phenols, isomerization of m- and/or p-cresols to o-cresol, demethylation of o-cresol, dealkylation of xylenols and other alkyl phenols, recycling of products other than phenol, and, optionally, reducing phenol to cyclohexanone/cyclohexanol, followed by oxidation thereof to adipic acid.Type: GrantFiled: May 21, 1985Date of Patent: August 12, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventor: Paul W. Wojtkowski
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Patent number: 4590306Abstract: The instant invention relates to a process for the conversion of meta/para-cresol mixtures by catalytically methylating the meta/para-cresol mixtures in their ortho-positions, separating the 2,3,6- and 2,4,6-trimethylphenols formed and converting subsequently the 2,4,6-trimethylphenol in the presence of iron oxide(s) or catalysts which contain iron oxide(s) and at least one additional oxide, to a mixture of methyl phenols, which is essentially free from meta-substituted methylphenols.Type: GrantFiled: February 19, 1985Date of Patent: May 20, 1986Assignee: Union Rheinische Braunkohlen Kraftstoff AktiengesellschaftInventors: Joachim Korff, Karl-Heinz Keim
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Patent number: 4554388Abstract: This invention relates to a process for isomerization and transalkylation of alkylphenols and for phenol-derivatives in the presence of a catalyst comprising ironoxide (s) and at least one additional oxide and in the case of 2,4,6-trimethylphenol and 2,4-dimethylphenol as alkylphenol feed, of ironoxide (s) or of a catalyst comprising ironoxide (s) and at least one additional oxide.Type: GrantFiled: February 7, 1984Date of Patent: November 19, 1985Assignee: Rheinische Braunkohlenwerke AktiengesellschaftInventors: Karl-Heinz Keim, Joachim Korff
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Patent number: 4538008Abstract: Secondary or tertiary alkyl phenyl ethers may be induced to undergo thermal rearrangement on alumina, aluminum phosphate, or a silica-modified alumina as catalyst to afford the isomeric ortho-alkylphenol. Such rearrangement generally occurs under milder conditions than does the alkylation of a phenol with an olefin using the same alumina as an alkylating catalyst with high regioselectivity and good control over the extent of alkylation.Type: GrantFiled: April 20, 1984Date of Patent: August 27, 1985Assignee: UOP Inc.Inventors: Bruce E. Firth, Terry J. Rosen
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Patent number: 4503269Abstract: An improvement in a process for the isomerization of cresols may be obtained by effecting the isomerization reaction of a cresol in the presence of a crystalline aluminosilicate zeolite catalyst and added hydrogen. The added hydrogen will provide stability and longer life to the catalyst as well as a more stable selectivity to the desired isomers. The isomerization reaction is effected at temperatures ranging from about 250.degree. to about 450.degree. C. and pressures ranging from 2 to about 75 atmospheres in the presence of added hydrogen, said hydrogen being present in a mole ratio in the range of from about 1:1 to about 10:1 moles of hydrogen per mole of cresol.Type: GrantFiled: September 21, 1983Date of Patent: March 5, 1985Assignee: UOP Inc.Inventors: Dusan J. Engel, Thomas P. Malloy, James P. Shoffner
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Patent number: 4503270Abstract: A method is provided for producing 2,3,6 trimethylphenol by rearrangement of 2,4,6 trimethylphenol in the presence of an aluminum based catalyst, such as AlCl.sub.3, and an acid upon heating the mixture to a temperature within the range of 80.degree. C. to 150.degree. C.Type: GrantFiled: November 21, 1983Date of Patent: March 5, 1985Assignee: General Electric CompanyInventor: John J. Talley
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Patent number: 4484011Abstract: The process for preparing 4-isopropylphenol (4-IPP) from 2-isopropylphenol (2-IPP) comprising contacting phenol with 2-IPP in the presence of a catalyst system selected from: (1) the combination of sulfuric acid on comminuted acid clay and a molecular sieve; and (2) trifluoromethane sulfonic acid (TFMSA); at a temperature of from about 90.degree. C. to about 250.degree. C., preferably from about 110.degree. C. to about 200.degree. C., wherein the initial mole ratio of phenol/2-IPP is from about 6 to about 2, preferably from about 4 to about 2.5, for a sufficient period to give a mole ratio of 4-IPP/2-IPP in the reaction system of from about 0.6 to about 1.5, and preferably from about 0.8 to about 1.2, without significant meta-isopropylphenol formation, i.e., less than about 10 mole %. In the isolation procedure, distillation separates the reaction mixture into phenol, 2-IPP, and 4-IPP.Type: GrantFiled: December 2, 1983Date of Patent: November 20, 1984Assignee: Eastman Kodak CompanyInventor: Dale E. Van Sickle
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Patent number: 4476330Abstract: Conversion, e.g. dehydration of aliphatic organic oxygenates having up to about 6 carbon atoms by contact with a crystalline aluminosilicate zeolite, preferably ZSM-5, having a silica to alumina ratio substantially greater than 10, at a temperature of about 70.degree. to 1400.degree. F., depending upon the exact nature of the reactant and product.Type: GrantFiled: August 18, 1981Date of Patent: October 9, 1984Assignee: Mobil Oil CorporationInventors: George T. Kerr, Charles J. Plank, Edward J. Rosinski
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Patent number: 4465871Abstract: Tertiary alkyl phenyl ethers may be induced to undergo thermal rearrangement on an alumina catalyst to afford the isomeric ortho-t-alkylphenol. Such rearrangement generally occurs under milder conditions than does the alkylation of a phenol with an olefin using the same alumina as an alkylating catalyst. The rearrangement remains regioselective even when the phenyl ring bears an alkoxy group, hence affords a good preparative route to such materials as 2-t-butyl-4-methoxyphenol.Type: GrantFiled: August 8, 1983Date of Patent: August 14, 1984Assignee: UOP Inc.Inventors: Bruce E. Firth, Terry J. Rosen
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Patent number: 4447657Abstract: Alkyl phenyl ethers may be induced to undergo thermal rearrangement on an alumina catalyst to afford the isomeric ortho-alkylphenol. Such rearrangement generally occurs under milder conditions than does the alkylation of a phenol with an olefin using the same alumina as an alkylating catalyst. Yields frequently are high with good selectivity.Type: GrantFiled: November 10, 1982Date of Patent: May 8, 1984Assignee: UOP Inc.Inventors: Bruce E. Firth, Terry J. Rosen
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Patent number: 4431846Abstract: A process is disclosed for reducing the concentration of o-ethylphenol in m,p-cresol by partially t-butylating a mixture of the above and equilibrating the resultant mixture to convert o-ethylphenol and its 6-t-butyl derivative to the thermodynamically most stable 4-t-butyl-o-ethylphenol. The resultant mixture may then be separated by fractional distillation to isolate m,p-cresol low in o-ethylphenol, optionally, the mono-t-butylated derivatives of m,p-cresol and leave behind the 4-t-butyl-o-ethylphenol, along with di-t-butylated derivatives of all the phenols.Type: GrantFiled: May 24, 1982Date of Patent: February 14, 1984Assignee: Koppers Company, Inc.Inventor: Gerd Leston
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Patent number: 4424382Abstract: Resorcinol is prepared by an improved process through superacid (such as perfluorinated alkanesulfonic superacids of one to eighteen carbon atoms or polymeric perfluorinated resinsulfonic acids, such as Nafion-H) catalyzed cleavage-rearrangement reaction of meta-isopropylphenol hydroperoxide in the form of its protected ether or ester derivatives, including readily cleavable and reusable trimethylsilyl and trifluoromethanesulfonyl derivates. Part of the process is the preparation of needed meta-isopropylphenol in high purity free of other isomers by treating any mixture of isopropylphenol isomers in an excess of anhydrous hydrogen fluoride or a perfluorinated alkanesulfonic superacid of one to eighteen carbon atoms and a Lewis acid fluoride or by alkylating (transalkylating) phenol with a propyl alkylating agent in the presence of the aforementioned superacid systems.Type: GrantFiled: June 1, 1982Date of Patent: January 3, 1984Assignee: PCUK Produits Chimiques Ugine KuhlmannInventor: George A. Olah
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Patent number: 4346249Abstract: Para-isopropenylphenol can be obtained by dehydrogenation of para-isopropylphenol in the presence of a calcium-nickel phosphate catalyst, phenol, and water.Type: GrantFiled: April 9, 1981Date of Patent: August 24, 1982Assignee: General Electric CompanyInventor: Herman O. Krabbenhoft
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Patent number: 4283571Abstract: Isomerization of o-cresol to m-cresol by contact with a crystalline aluminosilicate zeolite of the ZSM-type, having a silica to alumina ratio greater than 5, at a temperature of about 350.degree. to 450.degree. C.Type: GrantFiled: January 30, 1979Date of Patent: August 11, 1981Assignee: Union Rheinische Braunkohlen Kraftstoff AktiengesellschaftInventors: Karl-Heinz Keim, Reinhard Kiauk, Ewald Meisenburg
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Patent number: 4283572Abstract: A process for the conversion of an alkyl phenyl ether to the corresponding alkylphenol, involving heating in the presence of a dehydrated sulfonic acid type cation exchange resin having a macroreticular structure. The process has particular application to the recovery of unreacted alkylphenol from a product mixture resulting from a reaction in which the alkylphenol is used (in stoichiometrically excessive amounts) as a reactant.Type: GrantFiled: December 27, 1979Date of Patent: August 11, 1981Assignee: Borg-Warner CorporationInventor: James D. Klicker
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Patent number: 4138411Abstract: Aromatic alkenyl compounds, for example, eugenol and safrole, are isomerized, for example to isoeugenol and isosafrole, by contact with a ruthenium or osmium catalyst.Type: GrantFiled: April 14, 1976Date of Patent: February 6, 1979Assignee: Rhone-Poulenc S. A.Inventor: Pierre Gandilhon
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Patent number: 4103096Abstract: Meta-alkylphenols are prepared by the isomerization of nonmeta-alkylphenols in the presence of trifluoromethane sulfonic acid. Ortho-isomer-containing alkylphenols are isomerized to increase their meta-isomer content and reduce their ortho-isomer content.Type: GrantFiled: October 13, 1977Date of Patent: July 25, 1978Assignee: Stauffer Chemical CompanyInventors: Silvio L. Giolito, Stanley B. Mirviss
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Patent number: RE34626Abstract: This invention relates to a process for the preparation of bisphenols and bisphenol mixtures by the isomerization of bisphenols on acid or alkaline catalysts in the presence of the corresponding phenols.Type: GrantFiled: February 1, 1993Date of Patent: May 31, 1994Assignee: Bayer AGInventors: Udo Rudolph, Claus Wulff