Heavy Metal Or Aluminum Containing Catalyst Patents (Class 568/794)
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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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Publication number: 20090176998Abstract: The present invention relates to novel processes for the manufacture of chroman derivatives such as ?-tocopherol (TCP) and alkanoates thereof, especially ?-tocopheryl acetate (TCPA), whereby at least one step of the processes is carried out in the presence of a Lewis acid or a mixture of a Lewis acid with a Bronsted acid as the catalyst under pressure, preferably at an absolute pressure of at least 1.1 bar. As starting materials for the manufacture of TCP and its alkanoates either a mixture of 2,3,5-trimethylhydroquinone (TMHQ) or 2,3,6-trimethylhydroquinone-1-alkanoate (TMHQA) and a compound selected from the group consisting of phytol (PH), isophytol (IP) and (iso)phytol derivatives or 2-phytyl-3,5,6-trimethyl-hydroquinone (PTMHQ)/3-phytyl-2,5,6-trimethylhydroquinone-1-alkanoate (PTMHQA) and/or an isomer thereof are used. Suitable Lewis acids are indium(III) salts and scandium(III) salts. Suitable acid mixtures are iron/iron(II) chloride/hydrogen chloride and zinc(II) chloride/hydrogen chloride.Type: ApplicationFiled: March 6, 2009Publication date: July 9, 2009Inventors: Werner Bonrath, Yann Foricher, Thomas Netscher, Angela Wildermann
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Patent number: 7435273Abstract: Alkoxylated alkylphenols which have at least one long-chain alkyl radical having at least one tertiary or quaternary carbon atom are prepared and are used as fuel or lubricant additives in fuel and lubricant compositions.Type: GrantFiled: January 22, 2002Date of Patent: October 14, 2008Assignee: Basf AktiengesellschaftInventors: Arno Lange, Hans Peter Rath, Marc Walter
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Patent number: 7288683Abstract: An alkylation method comprises reacting a hydroxy aromatic compound with an alkyl alcohol in the presence of an alkylation catalyst comprising a metal oxide wherein the alkylation catalyst, has a surface area to volume ratio of about 950 to about 4,000 m2/m3, an aspect ratio of about 0.7 to about 1.0 or a combination of the foregoing.Type: GrantFiled: June 16, 2006Date of Patent: October 30, 2007Assignee: General Electric CompanyInventors: Hugo G. E. Ingelbrecht, David Parrillo, Mukund Parthasarathy, Gert-Jan Schoenmakers, Geuch Zijlma
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Patent number: 7282617Abstract: A process for making medium and long chain alkylaromatics and alkylphenols having a high level of anti-Markovnikov addition of the alkyl group. The alkylaromatics and alkylphenols made by the process of the present invention have enhanced stability and are particularly well suited to make highly stable oil additives and enhanced oil recovery surfactants.Type: GrantFiled: March 31, 2006Date of Patent: October 16, 2007Assignee: Chevron U.S.A. Inc.Inventors: William L. Schinski, Curt B. Campbell
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Patent number: 7208438Abstract: A method of making a catalyst comprising mixing a metal oxide precursor and a pore former to form a metal oxide precursor mixture and calcining the metal oxide precursor mixture in the presence of a flowing gas having a flow rate to form the catalyst comprising metal oxide. The catalyst comprises a first distribution of pores having a median pore diameter of 10 to 50 angstroms and a second distribution of pores having a median pore diameter of 1 to 500 angstroms. The median pore diameter of the second distribution of pores is inversely related to the flow rate of the gas.Type: GrantFiled: July 30, 2004Date of Patent: April 24, 2007Assignee: General Electric CompanyInventors: Hugo Gerard Eduard Ingelbrecht, Sabyasachi Mandal, Ashok Menon, Pradeep Nadkarni, Rupesh Pawar, Kuppuswamy Raghunathan, Gert-Jan Schoenmakers, Sahida Sharma
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Patent number: 6914163Abstract: Polyisobutenylphenols are prepared by alkylating an aromatic hydroxy compound with substantially monoethylenically unsaturated and substantially homopolymeric polyisobutenes in the presence of a Lewis acid alkylation catalyst by a process in which the polyisobutenes have a ? double bond content of at least 35 mol %.Type: GrantFiled: September 27, 2001Date of Patent: July 5, 2005Assignee: BASF AGInventors: Arno Lange, Hans Peter Rath
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Patent number: 6875897Abstract: Polyisobutenylphenols are prepared by alkylating an aromatic hydroxy compound with substantially monoethylenically unsaturated and substantially homopolymeric polyisobutenes in the presence of a Lewis acid alkylation catalyst by a process in which an ether is additionally used as a cocatalyst, the ether having a molecular weight of at least 102 g/mol in the case of BF3 as the Lewis acid.Type: GrantFiled: September 27, 2001Date of Patent: April 5, 2005Assignee: BASF AktiengesellschaftInventors: Arno Lange, Hans Peter Rath
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Patent number: 5847237Abstract: There is disclosed a catalyst for ortho-alkylation of phenols obtained by calcination of a catalyst precursor comprising a dry mixture of:(a) manganese oxalate;(b) phenolic resin fine particles; and(c) at least one magnesium compound selected from the group consisting of basic magnesium carbonate and magnesium hydroxide.There is further disclosed a process for producing ortho-alkylated phenols by the gas phase reaction between an alkyl alcohol and a phenol in the presence of the ortho-alkylation catalyst defined above.Type: GrantFiled: July 3, 1996Date of Patent: December 8, 1998Assignee: Honshu Chemical Industry Co., Ltd.Inventors: Shunji Yago, Takashi Kakiuchi, Keiji Arimatsu, Fujihisa Matsunaga
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Patent number: 5583268Abstract: A process of catalytically reacting a 3-18 carbon mono-olefin such as cyclohexene with an arylhydroxide such as phenol in the liquid phase forming an ortho-alkylated arylhydroxide which is subsequently catalytically dehydrogentated to form an ortho-alkenylarylhydroxide or ortho-arylarylhydroxide such as ortho-phenylphenol.Type: GrantFiled: December 15, 1995Date of Patent: December 10, 1996Assignee: The Dow Chemical CompanyInventors: Guo-shuh J. Lee, Juan M. Garces, Dennis A. Hucul, Tracy L. Young, Kenneth A. Burdett
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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: 5292970Abstract: A method of manufacturing orthosubstituted alkylphenols, employing a catalyst of increased activity, by reacting phenol or 2-alkylphenols with 2-alkyl-1-alkenes and/or 2-aryl-1-alkenes in the liquid phase, optionally in the presence of inert diluents and/or an excess of the alkene, wherein the reaction is carried out in the presence of modified aluminum-containing catalysts obtained by adding small amounts of polyhalophenols, each having at least 3 like or unlike halogen substituents from the group of the elements fluorine, chlorine, and bromine, serving as cocatalysts, to known aluminum trisphenolate catalysts, wherein the molar ratio between the cocatalysts and the aluminum compound is in the range 0.5:1-8:1.The invention also relates to the catalyst for manufacturing the ortho-alkylated phenols, which catalyst is comprised of the (2-alkyl)phenol undergoing alkylation, an organoaluminum compound, and a polyhalophenol as the (or a) cocatalyst.Type: GrantFiled: November 30, 1992Date of Patent: March 8, 1994Assignee: Huels AktiengesellschaftInventors: Friedrich-Wilhelm Kupper, Wolfgang Muller
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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: 5245089Abstract: Provided is a process for alkylating aromatic compounds in the presence of mixed oxides of titanium and gallium which have been found to be highly active catalysts for the alkylation of aromatics with alkyl esters, alcohols, olefins and ethers. When the alkyl acceptor is a phenol, the catalysts provide high reaction rates and high selectivity for ortho alkylated products.Type: GrantFiled: October 23, 1992Date of Patent: September 14, 1993Assignee: Eastman Kodak CompanyInventors: Gether Irick, Jr., Leslie S. LaForce
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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: 5144082Abstract: It is disclosed that aromatic compounds can be alkylated with mono-olefinic HVI-PAO dimer in contact with an acidic catalyst to produce novel alkylated aromatic compositions. It has been found that the novel HVI-PAO dimer alkylated aromatic compositions exhibit an extraordinary combination of properties relating to low viscosity with high viscosity index and low pour point which renders them very useful as lubricant basestock. Further, it has been found that the novel alkylaromatic compositions of the present invention show improved oxidative stability. Depending upon the substituent groups on the aromatic nucleus, useful lubricant additives can be prepared for improved antiwear, antioxidant and other properties. HVI-PAO dimer is prepared as a product or by-product from 1-alkene oligomerization using reduced chromium oxide on solid support. Particularly disclosed are the alkylphenols prepared by the process of alkylation a phenol at the aromatic nucleus with the novel oligomer.Type: GrantFiled: April 17, 1991Date of Patent: September 1, 1992Assignee: Mobil Oil CorporationInventors: Thomas R. Forbus, Bruce P. Pelrine
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Patent number: 5098945Abstract: A composition containing a) a polystyrene, substituted polystyrene, copolymer or terpolymer of styrene or of a substituted styrene, polycarbonate, polyester-carbonate, polyurethane, polyamide copolyamide, polyacetyl or polyphenylene oxide and b) at least one compound of the formula I ##STR1## in which R.sub.1 is methyl or ethyl and R.sub.2 is C.sub.2 -C.sub.30 alkyl.Compounds of the formula I in which R.sub.2 is C.sub.8 -C.sub.30 alkyl are novel and are suitable for stabilizing organic materials against thermal, oxidative and actinic degradation.Type: GrantFiled: February 11, 1991Date of Patent: March 24, 1992Assignee: Ciba-Geigy CorporationInventors: Rita Pitteloud, Paul Dubs
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Patent number: 5097079Abstract: Catalyst precursor compositions comprising a mixture of magnesium oxide or a source of magnesium oxide and a water insoluble zinc compound are described. The compositions are calcinable to a catalyst that is useful in reactions for the ortho-alkylation of phenols.Type: GrantFiled: July 6, 1990Date of Patent: March 17, 1992Assignee: General Electric CompanyInventors: James G. Bennett, Jr., Gregory R. Chambers
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Patent number: 5091594Abstract: For producing 2,6-di-tert-butylphenol and products therefrom, utilizing small quantities of aluminum tris-(2-tert-butylphenolate as a catalyst by reaction of 2-tert-butylphenol with isobutene in the liquid phase, the reaction is performed in the presence of diluents such as liquid saturated aliphatic or cycloaliphatic hydrocarbons, C.sub.5 -C.sub.16 alkenes of formula R.sub.1 --CH.dbd.CH.sub.2 or R.sub.2 --CH.dbd.CH--R.sub.3, C.sub.5 to C.sub.12 cycloalkenes, which contain no branching on the C.dbd.C-bond, excess isobutene or mixtures thereof, at temperatures of 0.degree. C. to 80.degree. C., pressures of 0.1 to 11 bars and catalyst amounts of 0.005 to 5 mol %, based on 2-tert-butylphenol. High conversions are obtained with few undesirable trialkylated products.Type: GrantFiled: December 11, 1990Date of Patent: February 25, 1992Assignee: Huels AktiengesellschaftInventors: Friedrich-Wilhelm Kupper, Wolfgang H. E. Muller, Alfred Oberholz
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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: 5030770Abstract: Thymol can be prepared by reaction of m-cresol with propene at elevated temperature and at atmospheric to superatmospheric pressure by using wide- and medium-pored zeolites which have a pore diameter of at least 5 .ANG. as heterogeneous catalysts.Type: GrantFiled: July 5, 1989Date of Patent: July 9, 1991Assignee: Bayer AktiengesellschaftInventors: Peter Wimmer, Hans-Josef Buysch, Lothar Puppe
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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: 4954475Abstract: Catalyst precursor compositions comprising a mixture of magnesium oxide or a source of magnesium oxide and a water insoluble zinc compound are described. The compositions are calcinable to a catalyst that is useful in reactions for the ortho-alkylation of phenols.Type: GrantFiled: November 30, 1987Date of Patent: September 4, 1990Assignee: General Electric CompanyInventors: James G. Bennett, Jr., Gregory R. Chambers
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Patent number: 4933509Abstract: A method is provided for ortho-alkylating phenol by passing a mixture of phenol and methanol through a heated magnesium oxide catalyst. The magnesium oxide catalyst is made by calcining magnesium carbonate and thereafter further heating the calcined product in the presence of steam.Type: GrantFiled: April 28, 1989Date of Patent: June 12, 1990Assignee: General Electric CompanyInventor: Gregory L. Warner
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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: 4906793Abstract: Crystalline silica-titania catalyst compositions, optionally containing magnesium, are disclosed; the titanium is introduced through the use of organo-titanate chelates wherein the titanium has a coordination number of at least 5. The compositions are used in acid-catalyzed reactions such as alkylation reactions.Type: GrantFiled: November 17, 1988Date of Patent: March 6, 1990Assignee: Aristech Chemical CorporationInventors: Leonard A. Cullo, Francis J. Shiring, III
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Patent number: 4870216Abstract: Phenols are selectively orthoalkylated in higher yields by the reverse addition of a phenol-aluminum phenoxide mixture to an olefin at alkylation temperature and under pressure sufficient to maintain a liquid olefin phase.Type: GrantFiled: June 24, 1988Date of Patent: September 26, 1989Assignee: Ethyl CorporationInventors: Jeffrey F. King, Charles W. Matthews, Eric S. Batman
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Patent number: 4870215Abstract: Phenol is di-orthoalkylated in high yield by reacting, in a first stage, phenol containing only 1 mole of an aluminum phenoxide for each 100-800 moles of phenol with an olefin at 85.degree.-175.degree. C. until the reaction mixture contains 3 wt percent or less phenol and then, in a second stage, continuing the reaction at 25.degree.-80.degree. C. until the mixture contains a substantial amount of 2,6-di-alkylphenol.Type: GrantFiled: June 24, 1988Date of Patent: September 26, 1989Assignee: Ethyl CorporationInventors: Steven L. Wiker, Charles W Matthews, Jeffrey F. King
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Patent number: 4851591Abstract: A catalyst precursor comprising a magnesium compound or material, optionally also containing other metal compounds, is activated for use by calcining at an elevated temperature in the presence of air or nitrogen, or under vacuum. The active catalyst which results may be used in processes for the ortho-alkylation of phenolic compounds, with good yields of and selectivity to the ortho-alkylated end product.Type: GrantFiled: December 16, 1987Date of Patent: July 25, 1989Assignee: General Electric CompanyInventors: Richard A. Battista, James G. Bennett, Jr., John J. Kokoszka, Freddie L. Tungate
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Patent number: 4731492Abstract: A process of ortho-alkylating arylhydroxides, e.g., phenol, by passing a mixture of arylhydroxide, olefin and an inert hydrocarbon diluent in the liquid phase through a bed of activated alumina at an elevated temperature and pressure. Conversion and selectivity is improved over that obtained without the diluent.Type: GrantFiled: March 4, 1987Date of Patent: March 15, 1988Assignee: Ethyl CorporationInventors: Steven L. Wiker, S. Wendell Holmes, Jr., Dixie E. Goins
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Patent number: 4677089Abstract: A catalyst precursor comprised of a dry admixture of manganese carbonate and at least one material selected from among magnesium carbonate, basic magnesium carbonate and magnesium hydroxide. The precursor is calcinable at elevated temperatures to an activated catalyst which may be used in a process for the ortho-alkylation of phenolic compounds.Type: GrantFiled: June 23, 1986Date of Patent: June 30, 1987Assignee: General Electric CompanyInventors: James G. Bennett, Jr., Freddie L. Tungate
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Patent number: 4665238Abstract: Alkylaromatic compounds may be synthesized by reacting an aromatic compound with an alkylating agent comprising a mixture of gases, including carbon monoxide and hydrogen at alkylation conditions in the presence of a dual-function-catalyst. The catalyst system which is employed for this reaction will comprise (1) a composite of oxides of copper and chromium and (2) an aluminosilicate which may be either in crystalline or amorphous form.Type: GrantFiled: September 9, 1985Date of Patent: May 12, 1987Assignee: UOP Inc.Inventors: Tamotsu Imai, Paul T. Barger
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Patent number: 4661638Abstract: A catalyst precursor prepared by precipitating manganese hydroxide from caustic solution and then mixing the precipitate with a magnesium-containing material is described. The catalyst precursor can be calcined to an active form, and the resulting catalyst can be used to effect or facilitate the ortho-alkylation of phenolic compounds in vapor phase reactions. Superiority of performance is demonstrated with respect to a catalyst derived from a precursor in which manganese hydroxide is precipitated (sometimes referred to as "co-precipitation") in the presence of a magnesium compound, rather than formed separately.Type: GrantFiled: September 16, 1985Date of Patent: April 28, 1987Assignee: General Electric CompanyInventors: Richard A. Battista, James G. Bennett, Jr., John J. Kokoszka, Freddie L. Tungate
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Patent number: 4599465Abstract: A process for producing an orthoalkylphenol which comprises reacting phenol with an olefin in a liquid phase in the presence of an alumina catalyst, characterized in that the water content in the liquid phase of the reaction system is maintained at a level of not higher than 250 ppm.Type: GrantFiled: June 5, 1985Date of Patent: July 8, 1986Assignee: Mitsubishi Chemical Industries, Ltd.Inventors: Akio Tamaru, Yoshiaki Izumisawa, Hidekichi Hashimoto, Kiyoji Kuma, Takashi Komaya, Masanobu Minagawa
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Patent number: 4594460Abstract: Substituted phenols of formula ##STR1## in which R.sub.1 is in an ortho or para position relative to the phenol function and denotes ##STR2## R.sub.2 denotes an acyclic radical optionally substituted by alkyl, hydroxy, alkoxycarbonyl, cyano or formyl, or a phenyl or naphthyl radical, and R denotes hydrogen or 1 to 4 substituents chosen from halogen, OH optionally in the form of ether or ester, alkyl, NO.sub.2, CHO optionally in the form of acetal, CH.sub.3 CO--, C.sub.6 H.sub.5 CO--, NH.sub.2, alkylamino, dialkylamino or alkoxycarbonyl, it being understood that 2 symbols R may form with the phenyl nucleus a condensed aromatic ring, which comprises reacting a butadiene of formula ##STR3## with a phenol for formula ##STR4## in water in the presence of a rhodium-based catalyst, a water-soluble phosphine and optionally an inorganic or organic base. The products of formula (I) are intermediates for the synthesis of vitamin E, antioxidants, perfumes or insecticides.Type: GrantFiled: March 19, 1985Date of Patent: June 10, 1986Assignee: Rhone-Poulenc SanteInventors: Gerard Mignani, Didier Morel
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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: 4568662Abstract: Preparation of alkylation catalysts containing iron oxide and/or chromium oxide, by means of a process which comprises:(a) precipitating hydrate oxides of iron and/or chromium from an aqueous solution of soluble compounds of said elements;(b) separating the thus obtained precipitate, and washing said precipitate;(c) granulating the washed precipitate, and drying the granules so obtained;(d) calcining said dried granules at high temperature;in which an organic carboxylic acid salt of iron and/or chromium is added to and homogenized with the washed precipitate from stage (b), and/or the dried granules from stage (c) are impregnated with an aqueous solution of an organic carboxylic acid salt of iron and/or chromium.The catalysts obtained by means of the above process are mechanically strong, and highly active in the production process of 2,6-xylenol by means of the alkylation of phenol or o-cresol with methanol.Type: GrantFiled: December 3, 1984Date of Patent: February 4, 1986Assignee: Enichimica S.p.A.Inventors: Jan Bialy, Irena Penczek, Nikuca Kopytowska, Josef Wrzyszcz, Jolanta Cmielowska, Hanna Grabowska, Wlodzimierz Kaczmarczyk, Kazimierz Mazur, Wlodzimierz Mista
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Patent number: 4560809Abstract: A process for the production of a 2,6-dialkylphenol in high yield wherein the alkyl groups are secondary or tertiary with a reduced overall production of 4-alkylphenol by-products by the aluminum phenoxide catalyzed pressure reaction of isobutylene with phenol and a mixture of 2,4-dialkylphenol and 2,4,6-trialkylphenol which may be obtained, in a cyclic process, as a bottom stream from the distillation of the reaction mixture to obtain the 2,6-dialkylphenol product.Type: GrantFiled: October 9, 1984Date of Patent: December 24, 1985Assignee: Ethyl CorporationInventors: Dixie E. Goins, Harold V. Huggins, Edward A. Burt, Silas W. Holmes
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Patent number: 4554267Abstract: Hydroxyaromatic compounds such as phenol are alkylated with alkanols such as methanol in the presence of a catalyst comprising magnesium oxide with up to about 0.1% by weight of copper deposited thereon in a layer of submicroscopic thickness. The catalyst is prepared by preparing a slurry of a substantially water-insoluble magnesium reagent such as magnesium hydroxide or magnesium carbonate in an aqueous solution of at least one copper salt, removing and drying the solid phase, and calcining the same at a temperature within the range of about 350.degree.-550.degree. C. The catalyst promotes ortho-alkylation of the hydroxyaromatic compound in high yield, minimizes decomposition of the alkanol, and has long life.Type: GrantFiled: June 3, 1983Date of Patent: November 19, 1985Assignee: General Electric CompanyInventors: Gregory R. Chambers, James G. Bennett, Jr.
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Patent number: 4554266Abstract: Hydroxyaromatic compounds such as phenol are alkylated with alkanols such as methanol in the presence of a catalyst comprising an intimate blend of magnesium oxide and copper, the latter being present in an amount up to about 2% by weight, based on said magnesium oxide. The catalyst is prepared by blending a magnesium reagent and copper in elemental or (preferably) chemically combined form and calcining the same at a temperature within the range of about 350.degree.-550.degree. C. The catalyst promotes ortho-alkylation of the hydroxyaromatic compound in high yield, minimizes decomposition of the alkanol, and has long life.Type: GrantFiled: June 3, 1983Date of Patent: November 19, 1985Assignee: General Electric CompanyInventors: James G. Bennett, Gregory R. Chambers
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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: 4547480Abstract: A catalyst precursor comprised of a dry admixture of manganese carbonate and at least one material selected from among magnesium carbonate, basic magnesium carbonate and magnesium hydroxide. The precursor is calcinable at elevated temperatures to an activated catalyst which may be used in a process for the ortho-alkylation of phenolic compounds.Type: GrantFiled: December 20, 1983Date of Patent: October 15, 1985Assignee: General Electric CompanyInventors: James G. Bennett, Jr., Freddie L. Tungate
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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