Preparing By Isomerization Patents (Class 568/783)
  • Patent number: 11485694
    Abstract: 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: Grant
    Filed: February 4, 2019
    Date of Patent: November 1, 2022
    Assignees: China Petroleum & Chemical Corporation, UOP LLC
    Inventors: Shuguang Zhang, Lubo Zhou
  • Patent number: 6887820
    Abstract: 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: Grant
    Filed: September 14, 2000
    Date of Patent: May 3, 2005
    Assignees: Japan Science and Technology Corporation, NKK Corporation, Takeda Pharmaceutical Company Limited, Asahi Kasei Pharma Corporation, Takasago International Corporation
    Inventors: Takao Ikariya, Shohei Hashiguchi, Jun Takehara, Nobuyuki Uematsu, Kazuhiko Matsumura, Ryoji Noyori, Akio Fujii
  • Patent number: 6433236
    Abstract: 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: Grant
    Filed: March 21, 2000
    Date of Patent: August 13, 2002
    Assignee: Arteva North America S.A.R.L.
    Inventors: David Anthony Schiraldi, Alexei Viktorovich Iretski, Sheldon Christopher Sherman, Laren Malcolm Tolbert, Mark Gilmore White
  • Publication number: 20020040169
    Abstract: 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: Application
    Filed: April 26, 2001
    Publication date: April 4, 2002
    Inventors: Anantha N. Desikan, George E. Whitwell
  • Patent number: 5399786
    Abstract: 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: Grant
    Filed: July 13, 1993
    Date of Patent: March 21, 1995
    Assignee: Rhodia S/A
    Inventors: Antonio U. B. Queiroz, Lumi T. Aikawa, deceased
  • Patent number: 5053558
    Abstract: 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: Grant
    Filed: July 3, 1990
    Date of Patent: October 1, 1991
    Assignee: UOP
    Inventors: J. W. Adriaan Sachtler, R. Joe Lawson
  • Patent number: 5015785
    Abstract: 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: Grant
    Filed: August 8, 1990
    Date of Patent: May 14, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Steck, Helmut Lermer, Matthias Schwarzmann, Toni Dockner
  • Patent number: 5015784
    Abstract: 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: Grant
    Filed: August 3, 1989
    Date of Patent: May 14, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Udo Rudolph, Claus Wulff
  • Patent number: 4709102
    Abstract: 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: Grant
    Filed: October 7, 1986
    Date of Patent: November 24, 1987
    Assignee: Celanese Corporation
    Inventor: Balaram B. G. Gupta
  • Patent number: 4691063
    Abstract: 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: Grant
    Filed: June 16, 1986
    Date of Patent: September 1, 1987
    Assignee: UOP Inc.
    Inventors: Dusan J. Engel, Jean-Pierre Gilson
  • Patent number: 4605790
    Abstract: 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: Grant
    Filed: May 21, 1985
    Date of Patent: August 12, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Paul W. Wojtkowski
  • Patent number: 4590306
    Abstract: 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: Grant
    Filed: February 19, 1985
    Date of Patent: May 20, 1986
    Assignee: Union Rheinische Braunkohlen Kraftstoff Aktiengesellschaft
    Inventors: Joachim Korff, Karl-Heinz Keim
  • Patent number: 4554388
    Abstract: 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: Grant
    Filed: February 7, 1984
    Date of Patent: November 19, 1985
    Assignee: Rheinische Braunkohlenwerke Aktiengesellschaft
    Inventors: Karl-Heinz Keim, Joachim Korff
  • Patent number: 4538008
    Abstract: 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: Grant
    Filed: April 20, 1984
    Date of Patent: August 27, 1985
    Assignee: UOP Inc.
    Inventors: Bruce E. Firth, Terry J. Rosen
  • Patent number: 4503269
    Abstract: 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: Grant
    Filed: September 21, 1983
    Date of Patent: March 5, 1985
    Assignee: UOP Inc.
    Inventors: Dusan J. Engel, Thomas P. Malloy, James P. Shoffner
  • Patent number: 4503270
    Abstract: 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: Grant
    Filed: November 21, 1983
    Date of Patent: March 5, 1985
    Assignee: General Electric Company
    Inventor: John J. Talley
  • Patent number: 4484011
    Abstract: 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: Grant
    Filed: December 2, 1983
    Date of Patent: November 20, 1984
    Assignee: Eastman Kodak Company
    Inventor: Dale E. Van Sickle
  • Patent number: 4476330
    Abstract: 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: Grant
    Filed: August 18, 1981
    Date of Patent: October 9, 1984
    Assignee: Mobil Oil Corporation
    Inventors: George T. Kerr, Charles J. Plank, Edward J. Rosinski
  • Patent number: 4465871
    Abstract: 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: Grant
    Filed: August 8, 1983
    Date of Patent: August 14, 1984
    Assignee: UOP Inc.
    Inventors: Bruce E. Firth, Terry J. Rosen
  • Patent number: 4447657
    Abstract: 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: Grant
    Filed: November 10, 1982
    Date of Patent: May 8, 1984
    Assignee: UOP Inc.
    Inventors: Bruce E. Firth, Terry J. Rosen
  • Patent number: 4431846
    Abstract: 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: Grant
    Filed: May 24, 1982
    Date of Patent: February 14, 1984
    Assignee: Koppers Company, Inc.
    Inventor: Gerd Leston
  • Patent number: 4424382
    Abstract: 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: Grant
    Filed: June 1, 1982
    Date of Patent: January 3, 1984
    Assignee: PCUK Produits Chimiques Ugine Kuhlmann
    Inventor: George A. Olah
  • Patent number: 4346249
    Abstract: Para-isopropenylphenol can be obtained by dehydrogenation of para-isopropylphenol in the presence of a calcium-nickel phosphate catalyst, phenol, and water.
    Type: Grant
    Filed: April 9, 1981
    Date of Patent: August 24, 1982
    Assignee: General Electric Company
    Inventor: Herman O. Krabbenhoft
  • Patent number: 4283571
    Abstract: 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: Grant
    Filed: January 30, 1979
    Date of Patent: August 11, 1981
    Assignee: Union Rheinische Braunkohlen Kraftstoff Aktiengesellschaft
    Inventors: Karl-Heinz Keim, Reinhard Kiauk, Ewald Meisenburg
  • Patent number: 4283572
    Abstract: 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: Grant
    Filed: December 27, 1979
    Date of Patent: August 11, 1981
    Assignee: Borg-Warner Corporation
    Inventor: James D. Klicker
  • Patent number: 4138411
    Abstract: 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: Grant
    Filed: April 14, 1976
    Date of Patent: February 6, 1979
    Assignee: Rhone-Poulenc S. A.
    Inventor: Pierre Gandilhon
  • Patent number: 4103096
    Abstract: 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: Grant
    Filed: October 13, 1977
    Date of Patent: July 25, 1978
    Assignee: Stauffer Chemical Company
    Inventors: Silvio L. Giolito, Stanley B. Mirviss
  • Patent number: RE34626
    Abstract: 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: Grant
    Filed: February 1, 1993
    Date of Patent: May 31, 1994
    Assignee: Bayer AG
    Inventors: Udo Rudolph, Claus Wulff