Silicon Containing Catalyst Patents (Class 568/791)
  • Patent number: 9212116
    Abstract: 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: Grant
    Filed: July 24, 2012
    Date of Patent: December 15, 2015
    Assignee: Dalian Institute of Chemical Physics, Chinese Academy of Sciences
    Inventors: Kunyuan Wang, Yunpeng Xu, Zhongmin Liu
  • Patent number: 8704006
    Abstract: 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: Grant
    Filed: December 10, 2010
    Date of Patent: April 22, 2014
    Assignee: Chevron Oronite Company LLC
    Inventors: Curtis Bay Campbell, Cedrick Mahieux
  • Publication number: 20130324760
    Abstract: 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: Application
    Filed: August 7, 2013
    Publication date: December 5, 2013
    Inventors: Ivy D. Johnson, Wenyih Frank Lai
  • Patent number: 8247621
    Abstract: 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: Grant
    Filed: October 12, 2009
    Date of Patent: August 21, 2012
    Assignee: Invista North America S.A.R.L.
    Inventors: Joachim C. Ritter, James Michael Garner
  • Patent number: 6670513
    Abstract: 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: Grant
    Filed: December 3, 1999
    Date of Patent: December 30, 2003
    Assignees: Chevron Oronite Company, LLC, Chevron Oronite S.A.
    Inventors: Curtis Bay Campbell, Jean Louis Le Coënt
  • Patent number: 5689024
    Abstract: 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: Grant
    Filed: December 1, 1994
    Date of Patent: November 18, 1997
    Assignee: Mobil Oil Corporation
    Inventor: Kirk D. Schmitt
  • Patent number: 5334775
    Abstract: 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: Grant
    Filed: June 2, 1993
    Date of Patent: August 2, 1994
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Antonio Gutierrez, Stuart L. Soled, Jose A. Paes
  • Patent number: 5300703
    Abstract: 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: Grant
    Filed: April 5, 1993
    Date of Patent: April 5, 1994
    Assignee: Texaco Chemical Company
    Inventor: John F. Knifton
  • Patent number: 5276215
    Abstract: 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: Grant
    Filed: April 9, 1993
    Date of Patent: January 4, 1994
    Assignee: Texaco Chemical Company
    Inventors: John F. Knifton, Yu-Hwa E. Sheu, Pei-Shing Dai
  • Patent number: 5243115
    Abstract: 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: Grant
    Filed: April 22, 1991
    Date of Patent: September 7, 1993
    Assignee: Chemical Research & Licensing Company
    Inventors: Lawrence A. Smith, Jr., Robert P. Arganbright, Dennis Hearn
  • Patent number: 5243116
    Abstract: 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: Grant
    Filed: December 22, 1989
    Date of Patent: September 7, 1993
    Assignee: The Dow Chemical Company
    Inventors: Guo-shuh J. Lee, Juan M. Garces, Garmt R. Meima, Matheus J. M. van der Aalst
  • Patent number: 5198595
    Abstract: 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: Grant
    Filed: June 21, 1991
    Date of Patent: March 30, 1993
    Assignee: The Dow Chemical Company
    Inventors: Guo-shuh J. Lee, Juan M. Garces, Garmt R. Meima, Matheus J. M. van der Aalst
  • Patent number: 5175375
    Abstract: 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: Grant
    Filed: October 11, 1991
    Date of Patent: December 29, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Clarence D. Chang, Stuart D. Hellring
  • Patent number: 5171896
    Abstract: 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: Grant
    Filed: March 5, 1992
    Date of Patent: December 15, 1992
    Assignee: Texaco Chemical Company
    Inventors: John F. Knifton, Yu-Hwa E. Sheu
  • Patent number: 5072054
    Abstract: 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: Grant
    Filed: July 31, 1990
    Date of Patent: December 10, 1991
    Assignee: Mobil Oil Corp.
    Inventors: David O. Marler, John P. McWilliams, Charles M. Smith
  • Patent number: 5059727
    Abstract: 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: Grant
    Filed: August 21, 1990
    Date of Patent: October 22, 1991
    Assignee: Mitsubishi Gas Chemical Co., Inc.
    Inventor: Muneo Ito
  • 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: 4954663
    Abstract: 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: Grant
    Filed: January 25, 1990
    Date of Patent: September 4, 1990
    Assignee: Mobil Oil Corp.
    Inventors: David O. Marler, John P. McWilliams
  • Patent number: 4927979
    Abstract: 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: Grant
    Filed: December 6, 1988
    Date of Patent: May 22, 1990
    Assignee: Maruzen Petrochemical Co., Ltd.
    Inventors: Takanori Yamagishi, Tsutomu Idai, Eiji Takahashi
  • Patent number: 4912264
    Abstract: 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: Grant
    Filed: June 3, 1987
    Date of Patent: March 27, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Akira Takeshita, Shinzaburo Masaki, Takeo Fujii, Tooru Tokumaru, Akira Murakami
  • Patent number: 4849569
    Abstract: 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: Grant
    Filed: October 17, 1988
    Date of Patent: July 18, 1989
    Assignee: Chemical Research & Licensing Company
    Inventor: Lawrence A. Smith, Jr.
  • Patent number: 4532368
    Abstract: 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: Grant
    Filed: February 1, 1984
    Date of Patent: July 30, 1985
    Assignee: Ethyl Corporation
    Inventors: Barry J. Swanson, Ronald L. Shubkin
  • 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: 4371714
    Abstract: 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: Grant
    Filed: December 30, 1980
    Date of Patent: February 1, 1983
    Assignee: Mobil Oil Corporation
    Inventor: Lewis B. Young
  • Patent number: 4359591
    Abstract: 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: Grant
    Filed: March 30, 1981
    Date of Patent: November 16, 1982
    Assignee: Union Rheinische Braunkohlen Kraftstoff Aktiengesellschaft
    Inventors: Max Fremery, Karl-Heinz Keim, Joachim Korff
  • Patent number: 4306106
    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 16, 1978
    Date of Patent: December 15, 1981
    Assignee: Mobil Oil Corporation
    Inventors: George T. Kerr, Charles J. Plank, Edward J. Rosinski
  • Patent number: 4243828
    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: June 5, 1978
    Date of Patent: January 6, 1981
    Assignee: Mobil Oil Corporation
    Inventors: George T. Kerr, Charles J. Plank, Edward J. Rosinski
  • Patent number: RE34076
    Abstract: 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: Grant
    Filed: July 15, 1991
    Date of Patent: September 22, 1992
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Akira Takeshita, Shinzaburo Masaki, Takeo Fujii, Tooru Tokumaru, Akira Murakami