Silicon Containing Catalyst Patents (Class 568/791)
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Patent number: 9212116Abstract: The present invention relates to a method for producing cresol from phenol and methanol via gas phase alkylation, in which phenol and methanol are preheated and mixed with diluent gas, then the mixture continuously go through a catalyst bed comprising the catalyst for alkylation of phenol with methanol, to produce cresol by gas phase reaction at the reaction temperature of 200˜500° C. and the weight hourly space velocity of 0.5˜20 h?1. The catalyst for alkylation of phenol with methanol is obtained by modification steps and using ZSM-5 zeolite, MCM-22 zeolite or Beta zeolite as an active composition. Using phenol and methanol as feedstock, the cresol selectivity can reach to 90%, and the p-cresol selectivity can reach to 58%. The catalyst is environmental friendly and non-corrosive to the equipment with a good stability and a broad prospect in industrial application.Type: GrantFiled: July 24, 2012Date of Patent: December 15, 2015Assignee: Dalian Institute of Chemical Physics, Chinese Academy of SciencesInventors: Kunyuan Wang, Yunpeng Xu, Zhongmin Liu
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Patent number: 8704006Abstract: A process for preparing an alkylated hydroxyl aromatic compound comprising reacting (a) a hydroxyl aromatic compound (I), having the following structure; wherein n 1, 2 or 3; m is 0, 1, 2, or 3 and R1 is Hydrogen or hydrocarbyl group; and (b) at least one ?-branched primary alcohol component in the presence of an alkylating catalyst thereby producing an alkylated hydroxyl aromatic compound.Type: GrantFiled: December 10, 2010Date of Patent: April 22, 2014Assignee: Chevron Oronite Company LLCInventors: Curtis Bay Campbell, Cedrick Mahieux
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Publication number: 20130324760Abstract: A method of crystallizing a crystalline molecular sieve having a pore size in the range of from about 2 to about 19 ?, said method comprising the steps of (a) providing a mixture comprising at least one source of ions of tetravalent element (Y), at least one hydroxide source (OH?), and water, said mixture having a solid-content in the range of from about 15 wt. % to about 50 wt. %; and (b) treating said mixture to form the desired crystalline molecular sieve with stirring at crystallization conditions sufficient to obtain a weight hourly throughput from about 0.005 to about 1 hr?1, wherein said crystallization conditions comprise a temperature in the range of from about 200° C. to about 500° C. and a crystallization time less than 100 hr.Type: ApplicationFiled: August 7, 2013Publication date: December 5, 2013Inventors: Ivy D. Johnson, Wenyih Frank Lai
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Patent number: 8247621Abstract: The invention relates to the preparation of alkylated phenols. More specifically, the invention relates to an improved process for the manufacture of 2-secondary-alkyl-4,5-di-normal-alkylphenols.Type: GrantFiled: October 12, 2009Date of Patent: August 21, 2012Assignee: Invista North America S.A.R.L.Inventors: Joachim C. Ritter, James Michael Garner
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Patent number: 6670513Abstract: An alkylated hydroxyl-containing aromatic compound is produced by isomerizing a normal alpha-olefin having from about 16 to about 30 carbon atoms in the presence of a first solid, acidic catalyst capable of inducing both olefin isomerization and skeletal isomerization to produce a mixture of isomerized olefin, then alkylating an hydroxyl-containing aromatic compound with the mixture of isomerized olefins in the presence of a second solid, acidic catalyst. The first solid, acidic catalyst can be SM-3, MAPO-11, SAPO-11, SSZ-32, ZSM-23, MAPO-39, SAPO-39, ZSM-22, SSZ-20, ZSM-35, SUZ-4, NU-23, NU-87, natural ferrierite or synthetic ferrierite. The second solid, acidic catalyst can be a sulfonic acid anionic ion exchange resin catalyst or an acidic clay.Type: GrantFiled: December 3, 1999Date of Patent: December 30, 2003Assignees: Chevron Oronite Company, LLC, Chevron Oronite S.A.Inventors: Curtis Bay Campbell, Jean Louis Le Coënt
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Patent number: 5689024Abstract: This invention relates to use of a new and improved form of crystalline material identified as having the structure of SUZ-9 as a sorbent or a catalyst for organic compound, e.g., hydrocarbon compound, conversion.Type: GrantFiled: December 1, 1994Date of Patent: November 18, 1997Assignee: Mobil Oil CorporationInventor: Kirk D. Schmitt
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Patent number: 5334775Abstract: A process for alkylating hydroxyaromatic compounds with a terminally unsaturated polymer in the presence of a partially or completely dehydrated heteropoly catalyst. The alkylated hydroxyaromatic compounds so formed are useful as precursors for the production of fuel and lubricant additives.Type: GrantFiled: June 2, 1993Date of Patent: August 2, 1994Assignee: Exxon Chemical Patents Inc.Inventors: Antonio Gutierrez, Stuart L. Soled, Jose A. Paes
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Patent number: 5300703Abstract: Disclosed is a one step method for synthesis of alkylphenols which comprises reacting phenol with the corresponding olefin under adiabatic conditions in the presence of a catalyst comprising a heteropoly acid represented by the structure:H.sub.8-n [XM.sub.12 O.sub.40 ]where x=P or Si, M=Mo or w.sub.v and n is an integer which is 4 or 5, alone, or deposited on an inert support, at a temperature of from 60.degree. C. to 250.degree. C. and a pressure of from near atmospheric to about 500 psi.Type: GrantFiled: April 5, 1993Date of Patent: April 5, 1994Assignee: Texaco Chemical CompanyInventor: John F. Knifton
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Patent number: 5276215Abstract: Disclosed is a one-step method for synthesis of alkylphenols which comprises reacting phenol with the corresponding olefin under adiabatic conditions in the presence of a zeolite catalyst, preferably a dealuminated Y-zeolite, a modified Y-zeolite, or a .beta.-zeolite.Type: GrantFiled: April 9, 1993Date of Patent: January 4, 1994Assignee: Texaco Chemical CompanyInventors: John F. Knifton, Yu-Hwa E. Sheu, Pei-Shing Dai
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Patent number: 5243115Abstract: Aromatic compounds are alkylated in a catalytic distillation, wherein the catalyst structure also serves as a distillation component by contacting the aromatic compound with a C.sub.2 to C.sub.10 olefin in the catalyst bed under 0.25 to 50 atmospheres of pressure and at temperatures in the range of 80.degree. C. to 500.degree. C., using as the catalyst a mole sieve characterized as acidic or an acidic cation exchange resin. For example, ethyl benzene is produced by feeding ethylene to about the mid point of the catalyst bed while benzene is conveniently added through the reflux in molar excess to that required to react with ethylene, thereby reacting substantially all of the ethylene and recovering benzene as the principal overhead and ethyl benzene in the bottoms.Type: GrantFiled: April 22, 1991Date of Patent: September 7, 1993Assignee: Chemical Research & Licensing CompanyInventors: Lawrence A. Smith, Jr., Robert P. Arganbright, Dennis Hearn
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Patent number: 5243116Abstract: Alkylated benzenes such as ethylbenzene and cumene are produced by alkylation and/or transalkylation in the presence of an acidic mordenite zeolite catalyst having a silica/alumina molar ratio of at least 30:1 and a crystalline structure which is determined by X-ray diffraction to be a matrix of Cmcm symmetry having dispersed therein domains of Cmmm symmetry.Type: GrantFiled: December 22, 1989Date of Patent: September 7, 1993Assignee: The Dow Chemical CompanyInventors: Guo-shuh J. Lee, Juan M. Garces, Garmt R. Meima, Matheus J. M. van der Aalst
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Patent number: 5198595Abstract: Monoalkylated benzene such as ethylbenzene and cumene or monoalkylated substituted benzene are produced by alkylation in the presence of an acidic mordenite zeolite catalyst having a silica/alumina molar ratio of at least 40:1, preferably 160:1. In a subsequent, optional process, the polyalkylated benzene or polyalkylated substituted benzene produced in the alkylation is transalkylated in the presence of an acidic mordenite zeolite catalyst.Type: GrantFiled: June 21, 1991Date of Patent: March 30, 1993Assignee: The Dow Chemical CompanyInventors: Guo-shuh J. Lee, Juan M. Garces, Garmt R. Meima, Matheus J. M. van der Aalst
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Patent number: 5175375Abstract: The invention relates to producing ortho isopropyl phenol catalytically by contacting phenol with isopropanol or propylene, at a temperature of from about 200.degree. C. to about 300.degree. C., with ZSM-12 and zeolite Beta; and recovering ortho isopropyl phenol.Type: GrantFiled: October 11, 1991Date of Patent: December 29, 1992Assignee: Mobil Oil CorporationInventors: Clarence D. Chang, Stuart D. Hellring
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Patent number: 5171896Abstract: Disclosed is a one step method for synthesis of alkylphenols which comprises reacting phenol with the corresponding olefin under adiabatic conditions in the presence of a catalyst comprising an acidic montmorillonite clay having the structure:M.sub.x/n.sup.n+ .multidot.yH.sub.2 O(Al.sub.4-x Mg.sub.x)(Si.sub.8)O.sub.20 (OH).sub.4where M represent the interlamellar (balancing cation, normally sodium or lithium) and x, y and n are integers, wherein the acidic clay has been pretreated with an acid and optionally has deposited thereon an acid selected from the group consisting hydrogen fluoride, a fluorosulfonic acid or a mineral acid, at a temperature of from 60.degree. C. to 250.degree. C. and a pressure of from near atmospheric to about 500 psi.Type: GrantFiled: March 5, 1992Date of Patent: December 15, 1992Assignee: Texaco Chemical CompanyInventors: John F. Knifton, Yu-Hwa E. Sheu
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Patent number: 5072054Abstract: Short-chain alkyl phenols are prepared by reacting an alkylatable phenolic compound with an alkylating agent having one or more available alkylating aliphatic groups of from one to five carbon atoms. The reaction is carried out under alkylation conditions with a zeolite catalyst characterized by x-ray diffraction values as set forth in Tables A to D, infra.Type: GrantFiled: July 31, 1990Date of Patent: December 10, 1991Assignee: Mobil Oil Corp.Inventors: David O. Marler, John P. McWilliams, Charles M. Smith
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Patent number: 5059727Abstract: A method of alkylating phenols which comprises reacting phenols having a hydrogen atom in at least one of the ortho-positions with regard to the hydroxyl group with an alcohol in a gaseous phase under heat in the presence of a catalyst comprising iron oxide, silica, chromium oxide, germanium oxide and an alkali metal compound. The catalyst exhibits a long catalytic activity duration and decreases frequency of regeneration and replacement of catalysts.Type: GrantFiled: August 21, 1990Date of Patent: October 22, 1991Assignee: Mitsubishi Gas Chemical Co., Inc.Inventor: Muneo Ito
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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: 4954663Abstract: Long chain alkyl phenols are prepared by alkylating an alkylatable phenolic compound with a long chain alkylating agent under alkylation reaction conditions in the presence of catalyst comprising a synthetic porous crystalline material characterized by an X-ray diffraction pattern including interplanar d-spacings at 12.36.+-.0.4, 11.03.+-.0.2, 8.83.+-.0.14, 6.18.+-.0.12, 6.00.+-.0.10, 4.06.+-.0.07; 3.91.+-.0.07 and 3.42.+-.0.06 Angstroms.Type: GrantFiled: January 25, 1990Date of Patent: September 4, 1990Assignee: Mobil Oil Corp.Inventors: David O. Marler, John P. McWilliams
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Patent number: 4927979Abstract: A very simple process for preparing p-ethylphenol is disclosed. It is only necessary to contact phenol with an ethylating agent in vapor phase in the presence of a specific catalyst. The catalyst can be obtained by incorporating one or more alkoxysilanes to a crystalline aluminosilicte with a constraint index of 1-15 having a silica/alumina molar ratio of 20-400, wherein the amount of said alkoxysilanes to be incorporated is not less than 1.4 wt % calculated as silicon based on the amount of said crystalline aluminosilicate. Because the specific catalyst has the narrowed or restricted entrances of the micro pores of the crystalline aluminosilicate by the alkoxysilane treatment, it is possible to prepare p-ethylphenol in a high selectivity. The product contains only a very small amount of m-ethylphenol.Type: GrantFiled: December 6, 1988Date of Patent: May 22, 1990Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Takanori Yamagishi, Tsutomu Idai, Eiji Takahashi
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Patent number: 4912264Abstract: Process for producing hydroxy-containing alkylated aromatic compounds by the liquid phase reaction of an aromatic compound having at least one hydroxyl group with an alkylating agent in the presence of a heteropoly acid and water.Type: GrantFiled: June 3, 1987Date of Patent: March 27, 1990Assignee: Sumitomo Chemical Company, LimitedInventors: Akira Takeshita, Shinzaburo Masaki, Takeo Fujii, Tooru Tokumaru, Akira Murakami
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Patent number: 4849569Abstract: Aromatic compounds are alkylated in a catalytic distillation, wherein the catalyst structure also serves as a distillation component by contacting the aromatic compound with a C.sub.2 to C.sub.10 olefin in the catalyst bed under 0.25 to 50 atmospheres of pressure and at temperatures in the range of 80.degree. C. to 500.degree. C., using as the catalyst a mole sieve characterized as acidic or an acidic cation exchange resin. For example, ethyl benzene is produced by feeding ethylene below the catalyst bed while benzene is conveniently added through the reflux in molar excess to that required to react with ethylene, thereby reacting substantially all of the ethylene and recovering benzene as the principal overhead and ethyl benzene in the bottoms.Type: GrantFiled: October 17, 1988Date of Patent: July 18, 1989Assignee: Chemical Research & Licensing CompanyInventor: Lawrence A. Smith, Jr.
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Patent number: 4532368Abstract: A process for making a mixture of meta- and para-alkylphenols by contacting a mixture of phenol, ortho-alkylphenol and an alkylating agent (e.g. olefins or lower alcohols) with a zeolite having a silica:alumina ratio of at least 12:1 under alkylating conditions to obtain a mixture of ortho-, meta- and para-alkylphenols and then separating at least part of the ortho-alkylphenol which is recycled to a subsequent alkylation process carried out in the same manner.Type: GrantFiled: February 1, 1984Date of Patent: July 30, 1985Assignee: Ethyl CorporationInventors: Barry J. Swanson, Ronald L. Shubkin
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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: 4371714Abstract: A process for the selective alkylation of phenol or its alkyl ethers, in the presence of a particular type of zeolite catalyst, to produce a product rich in 4-alkyl phenyl alkyl ethers (e.g. 4-methylanisole). The zeolite is characterized by a Constraint Index of 1 to 12 and a silica to alumina mole ratio of at least 12, and may optionally contain a minor amount of a difficultly reducible oxide.Type: GrantFiled: December 30, 1980Date of Patent: February 1, 1983Assignee: Mobil Oil CorporationInventor: Lewis B. Young
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Patent number: 4359591Abstract: This invention relates to a process for reacting phenol, mono- and di-alkyl phenols having at least one free o-position with methanol and/or dimethyl ether in the gas phase to form o-substituted phenols in the presence of a catalyst of oxides of iron, chromium, silicon and at least one oxide of an alkaline-earth metal, lanthanum and manganese or in the presence of a catalyst of oxides of iron, chromium, a metal from the group comprising germanium, titanium, zirconium, tin, lead, and at least one oxide of an alkali metal, alkaline-earth metal, lanthanum and manganese.Type: GrantFiled: March 30, 1981Date of Patent: November 16, 1982Assignee: Union Rheinische Braunkohlen Kraftstoff AktiengesellschaftInventors: Max Fremery, Karl-Heinz Keim, Joachim Korff
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Patent number: 4306106Abstract: 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 16, 1978Date of Patent: December 15, 1981Assignee: Mobil Oil CorporationInventors: George T. Kerr, Charles J. Plank, Edward J. Rosinski
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Patent number: 4243828Abstract: 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: June 5, 1978Date of Patent: January 6, 1981Assignee: Mobil Oil CorporationInventors: George T. Kerr, Charles J. Plank, Edward J. Rosinski
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Patent number: RE34076Abstract: Process for producing hydroxy-containing alkylated aromatic compounds by the liquid phase reaction of an aromatic compound having at least one hydroxyl group with an alkylating agent in the presence of a heteropoly acid and water.Type: GrantFiled: July 15, 1991Date of Patent: September 22, 1992Assignee: Sumitomo Chemical Company LimitedInventors: Akira Takeshita, Shinzaburo Masaki, Takeo Fujii, Tooru Tokumaru, Akira Murakami