Preparing Esters From Ethers Patents (Class 560/240)
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Patent number: 5852208Abstract: A process of producing compounds containing an acyloxyalkoxy group from an alcohol consists of reacting the alcohol with a formaldehyde donor until a compound of the formula:R--O--CH.sub.2 (OCH.sub.2).sub.X OR (V)is generated, wherein x is between about 1 to about 5 and R is an organic moiety. This product is then reacted with a carboxylic acid anhydride. The resulting product has the formula:R--O--CH.sub.2 O--COR.sup.1wherein R.sup.1 is a C.sub.1 -C.sub.6 alkyl group. The invention further relates to intermediates used in the production of such acyloxyalkoxylated compounds.Type: GrantFiled: August 30, 1996Date of Patent: December 22, 1998Assignee: Dixie Chemical Company, Inc.Inventor: Joseph C. Rongione
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Patent number: 5773648Abstract: A process for the preparation of polytetrahydrofuran or polytetrahydrofuran monoesters of C.sub.1 -C.sub.10 monocarboxylic acids by the polymerization of tetrahydrofuran over a heterogeneous catalyst in the presence of one of the telogens water, 1,4-butanediol or polytetrahydrofuran having a molecular weight of from 200 to 700 dalton or a C.sub.1 -C.sub.10 monocarboxylic acid or mixtures of these telogens, wherein a supported catalyst is used as catalyst, which contains a catalytically active amount of an oxygen-containing tungsten or molybdenum compound or mixtures of these compounds on an oxidic support material and which was calcined at temperatures ranging from 500.degree. to 1000.degree. C. following the application of the precursor compounds of said oxygen-containing molybdenum and/or tungsten compounds to the support material precursor.Type: GrantFiled: March 7, 1997Date of Patent: June 30, 1998Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Christoph Sigwart, Michael Hesse, Rolf Fischer, Karsten Eller, Gerd Heilen, Klaus-Dieter Plitzko
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Patent number: 5684179Abstract: An improved method for recovering purified diesters of polytetramethylene ethers involving the polymerization of tetrahydrofuran (THF) optionally with one or more comonomers (e.g., 3-methyl THF, ethylene oxide, propylene oxide, or the like) utilizing a solid acid catalyst (e.g., Nafion.RTM.) and a carboxylic acid with carboxylic acid anhydride (e.g., acetic acid with acetic anhydride) as molecular weight control agents wherein after polymerization product recovery involves bulk flashing of unreacted THF and stripping of remaining THF, carboxylic acid and carboxylic acid anhydride (e.g., acetic acid and acetic anhydride) by use of superheated THF. Such a process is useful in producing high purity commercial grade PTMEA that advantageously avoids problems associated with the presence of high boilers when converting to PTMEG.Type: GrantFiled: December 14, 1995Date of Patent: November 4, 1997Assignee: E. I. du Pont de Nemours and CompanyInventor: Suriyanarayan Dorai
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Patent number: 5663422Abstract: A process for the preparation of a 1,2-diacetoxy ester comprises acetylation of an epoxide with an acetic anhydride in the presence of a quaternary phosphonium acetate catalyst or its complex with acetic acid.Type: GrantFiled: March 1, 1996Date of Patent: September 2, 1997Assignee: Eastman Chemical CompanyInventors: Steven Thomas Perri, Stephen Neal Falling
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Patent number: 5659073Abstract: Disclosed is a method of making a glycol ether acetate. Acetic acid is reacted with a glycol ether at a molar ratio of about 1.1 to about 2, in a mixture with a catalyst and an azeotropic agent which can be either butyl acetate or dibutyl ether. The mixture is heated to a temperature and pressure sufficient to vaporize an azeotrope of water and the azeotropic agent. In another embodiment of the invention, a glycol ether acetate is made by preparing a reaction mixture of acetic acid and a glycol ether in a molar ratio of about 1.1 to about 1.2, about 5 to about 25 wt % n-butanol, an additional amount of acetic acid stoichiometric with the amount of n-butanol, and a catalyst. The reaction mixture is heated to form a glycol ether acetate, water, and butyl acetate. The azeotrope, excess acetic acid, butyl acetate, and glycol ether are successively removed by distillation.Type: GrantFiled: July 7, 1995Date of Patent: August 19, 1997Inventor: Jian Steven Qi
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Patent number: 5659068Abstract: Polyoxyalkylene glycol monoesters of carboxylic acids are prepared by a process in which tetrahydrofuran or a mixture of tetrahydrofuran with a total of not more than 95 mol %, based on the amount of tetrahydrofuran used, of one or more comonomers from the group consisting of the cyclic ethers and acetals is polymerized in the absence of water and in the presence of a carboxylic acid and of an anhydrous heteropolyacid catalyst.Type: GrantFiled: May 31, 1994Date of Patent: August 19, 1997Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Weyer, Rolf Fischer, Gerhard Jeschek, Herbert Mueller
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Patent number: 5648558Abstract: A method for producing a polyoxyalkylene glycol by ring opening polymerization of a cyclic ether, wherein a zeolite (other than ZSM-5, ZSM-11 and Nu-5) is used as a catalyst.Type: GrantFiled: March 16, 1994Date of Patent: July 15, 1997Assignee: Mitsubishi Chemical CorporationInventors: Masakatsu Hatano, Akio Nakanishi, Yoshio Kabata, Masayuki Shirado, Hiroshi Takeo, Mitsuharu Kobayashi
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Patent number: 5641857Abstract: Polytetrahydrofuran or polytetrahydrofuran monoesters of C.sub.1 -C.sub.20 -monocarboxylic acids or polytetrahydrofuran monoethers of monohydric C.sub.1 -C.sub.20 -alcohols, having an average molecular weight of from 250 to 10,000 Dalton and liquid at room temperature, are prepared by the cationic polymerization of tetrahydrofuran in the presence of a telogen by a process in which tetrahydrofuran is polymerized in the presence of water, 1,4-butanediol and/or polytetrahydrofuran having an average molecular weight of from 200 to 700 Dalton and/or of a C.sub.1 -C.sub.20 -monocarboxylic acid and/or of a monohydric C.sub.1 -C.sub.20 -alcohol with the aid of a catalytic amount of a zeolite catalyst which has an SiO.sub.2 /Al.sub.2 O.sub.3 molar ratio of from 4:1 to 100:1 and in which the population ratio P of the acid centers on the external surface of the zeolite to the total number of acid centers of the zeolite is 0.03/l or more.Type: GrantFiled: November 7, 1995Date of Patent: June 24, 1997Assignee: BASF AktiengesellschaftInventors: Roman Dostalek, Rolf Fischer, Ulrich Mueller, Rainer Becker
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Patent number: 5623086Abstract: A process for the preparation of 1,2-bis(acyloxyates) comprises acylation of epoxides with carboxylic anhydrides in the presence of a catalytic composition containing a tertiary amine and a carboxylic acid. Preferably, the carboxylic acid is a conjugate acid of the carboxylic anhydride. The carboxylic acid acts as a co-catalyst and its use in conjunction with the tertiary amine significantly increases the rate of reaction and results in higher selectivity. The catalytic composition may be prepared prior to acylation or in situ providing application versatility.Type: GrantFiled: December 29, 1995Date of Patent: April 22, 1997Assignee: Eastman Chemical CompanyInventors: Steven T. Perri, Stephen N. Falling
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Patent number: 5463020Abstract: Polytetrahydrofuran or C.sub.2 -C.sub.10 -alkylene oxide/tetrahydrofuran copolymers having a molecular weight of from 250 to 20,000 Dalton are prepared by the cationic polymerization of tetrahydrofuran or tetrahydrofuran and C.sub.2 -C.sub.10 -alkylene oxides in the prsence of a promoter by a process in which the catalyst used is a mixture of one or more C.sub.2 -C.sub.6 -di- or tricarboxylic acids with boric acid.Type: GrantFiled: June 30, 1994Date of Patent: October 31, 1995Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Michael Huellmann, Christof Palm, Wolfgang Franzischka
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Patent number: 5416240Abstract: Polyoxyalkylene glycols are prepared by a process in which tetrahydrofuran is polymerized with a total of not more than 95 mol %, based on the amount of tetrahydrofuran used, of one or more comonomers from the group consisting of the cyclic ethers and acetals in the absence of water and in the presence of a monohydric alcohol or of a monocarboxylic acid with the aid of an anhydrous heteropoly acid catalyst, and the polyoxyalkylene glycol is liberated from the resulting polyoxyalkylene glycol monoethers or polyoxyalkylene glycol monoesters by cleavage of the monoether or monoester bond.Type: GrantFiled: March 2, 1993Date of Patent: May 16, 1995Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Weyer, Rolf Fischer, Gerhard Jeschek, Franz Merger, Herbert Mueller
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Patent number: 5371276Abstract: A method for preparing ester end-capped polyalkylene ether is disclosed. Cyclic ether monomers are subjected to ring-opening polymerzation at a temperature of 20.degree.-80.degree. C. and a pressure of 0-10 atm in the presence of a solid acid serving as catalyst and a mixture of acid and acid anhydride serving as a promoter. The solid acid is an oxide of group III and group IV elements and has been modified by sulfuric acid, ammonium sulfate or ammonium sulfite.Type: GrantFiled: November 24, 1993Date of Patent: December 6, 1994Assignee: Industrial Technology Research InstituteInventors: Shiao-Jung Chu, Fu-Chen Liu, Ching-Tang Lin, Huey-Jiuan Yeh, Fu-Hsi Yu
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Patent number: 5344964Abstract: A method for preparing ester end-capped polyalkylene ether is disclosed. Cyclic ether monomers are subjected to ring-opening polymerization at a temperature of 10.degree.-80.degree. C. and a pressure of 0-10 atm in the presence of a solid acid of a mixed oxide of group III and group IV elements serving as catalyst and a mixture of acid and acid anhydride serving as molecular weight moidifier. The group III and group IV elements used should have a Ho index of +3.0 to -10.0.Type: GrantFiled: November 24, 1993Date of Patent: September 6, 1994Assignee: Industrial Technology Research InstituteInventors: Shiao-Jung Chu, Fu-Chen Liu, Ching-Tang Lin, Wen-Fa Lin, Kuei-Chih Wang, Sheng-Te Yang
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Patent number: 5298650Abstract: The present invention is a process for producing organic esters wherein a dialkyl ether and a carboxylic acid are reacted in the presence of a solid phase acidic catalyst having an acidity factor of at least 0.30, preferably at least 1, under reaction conditions sufficient to form a reaction mixture comprising the desired organic ester and an alcohol and recovering the organic ester. For example, methyl acetate can be prepared by reacting dimethyl ether and acetic acid in the presence of montmorillonite, amorphous silica-alumina or .kappa.-alumina under conditions sufficient to form methyl acetate. While typical processes produce an azeotropic mixture of the desired organic ester and water, the claimed process utilizes a combination or reactants and catalysts wherein water is not produced in appreciable amounts. Therefore, the organic ester product can be separated conveniently thereby avoiding a cumbersome azeotropic distillation step as required in prior art processes.Type: GrantFiled: April 15, 1992Date of Patent: March 29, 1994Assignee: Air Products and Chemicals, Inc.Inventors: Francis J. Waller, William F. Burgoyne, Jr.
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Patent number: 5262562Abstract: A method is disclosed wherein tetrahydrofuran is reacted in the presence of acetic anhydride and a catalyst to provide acetate derivatives of polyglycols and using as a catalyst a triflic acid-modified montmorillonite clay at a temperature of 0.degree.-1000.degree. C. and atmospheric pressure.Type: GrantFiled: February 14, 1992Date of Patent: November 16, 1993Assignee: Texaco Chemical CompanyInventors: Donald R. Hollingsworth, John F. Knifton
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Patent number: 5254723Abstract: A process for making glycol diesters from polyethers is disclosed. The polyether is reacted with an acyclic, aliphatic anhydride in the presence of a Lewis acid to produce the glycol diester. The invention provides a way to reuse polyether polyols recovered from polyurethanes by converting them to readily purified glycol diesters. The diesters are useful as solvents and as chemical intermediates.Type: GrantFiled: November 23, 1992Date of Patent: October 19, 1993Assignee: ARCO Chemical Technology, L.P.Inventors: Lau S. Yang, Diane A. Macarevich
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Patent number: 5225590Abstract: Intermediates and methods for producing intermediates for use in preparing 9-(1,3-dihydroxy-2-propoxymethyl)-guanine and esters and ethers thereof.Type: GrantFiled: April 26, 1988Date of Patent: July 6, 1993Assignee: Syntex (U.S.A.) Inc.Inventors: David J. Morgans, Jr., Harlan H. Chapman
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Patent number: 5218141Abstract: Polyoxybutylene polyoxyalkylene glycol dicarboxylates are prepared by a process in which tetrahydrofuran is copolymerized with a molar excess of a 1,2-alkylene oxide in the presence of a carboxylic anhydride using, as a catalyst, a bleaching earth containing less than 3% by weight of water.Type: GrantFiled: November 6, 1991Date of Patent: June 8, 1993Assignee: BASF AktiengesellschaftInventor: Herbert Mueller
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Patent number: 5214200Abstract: The present invention is a process for producing organic esters wherein a dialkyl ether and a carboxylic acid are reacted in the presence of a catalyst consisting essentially of an iodide of a Group IA element under reaction conditions sufficient to form a reaction mixture comprising the desired organic ester and an alcohol and recovering the ester from the reaction product mixture. For example, methyl acetate can be prepared by reacting dimethyl ether and acetic acid in the presence of a hydrogen iodide or lithium iodide catalyst under conditions sufficient to form methyl acetate and methanol. While typical processes produce an azeotropic mixture of the desired organic ester and water, the claimed process utilizes a combination or reactants and catalysts wherein water is not produced in appreciable amounts. Therefore, the organic ester product can be separated conveniently thereby avoiding a cumbersome azeotropic distillation step as required in prior art processes.Type: GrantFiled: April 15, 1992Date of Patent: May 25, 1993Assignee: Air Products and Chemicals, Inc.Inventor: Francis J. Waller
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Patent number: 5210325Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalyst which comprises one or more compounds comprising a rare earth element and phosphorus supported on an inert porous support. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: August 10, 1992Date of Patent: May 11, 1993Assignee: Shell Oil CompanyInventors: Richard A. Kemp, Paul R. Weider
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Patent number: 5210283Abstract: Tetrahydrofuran is polymerized in the presence of a carboxylic acid anhydride and a solid acid catalyst that has been calcined at a temperature greater than about 600.degree. C. Calcined bleaching earth catalysts give THF polymer products having a narrow molecular weight distribution; calcining amorphous silica-aluminas improves their activity toward THF polymerization.Type: GrantFiled: May 18, 1992Date of Patent: May 11, 1993Assignee: ARCO Chemical Technology, L.P.Inventors: Andrew P. Kahn, Robert G. Gastinger, Gangfeng Cai
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Patent number: 5208385Abstract: A process for producing tetrahydrofuran polymers having a narrow molecular weight distribution is disclosed. Tetrahydrofuran is polymerized in the presence of a carboxylic acid anhydride and amorphous silica-alumina. The process overcomes the need for costly post-treatment techniques such as distillation and selective solvent extraction.Type: GrantFiled: February 19, 1992Date of Patent: May 4, 1993Assignee: Arco Chemical Technology, L.P.Inventors: Andrew P. Kahn, Robert G. Gastinger, Rangasamy Pitchai
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Patent number: 5202463Abstract: An improved process for preparing and purifying glycol ether esters is disclosed. An azeotroping agent is included at a sufficiently low level to allow removal of the water of reaction, but also permit removal of by-products from esterification in the low-boiling component.Type: GrantFiled: September 10, 1991Date of Patent: April 13, 1993Assignee: ARCO Chemical Technology, L.P.Inventor: Jude T. Ruszkay
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Patent number: 5189199Abstract: A process is disclosed for the preparation of 1,4-dioxy-2-butenes by reacting 3,4-epoxy-1-butene with an oxygen nucleophile in the presence of a Pd(O) complex catalyst.Type: GrantFiled: February 20, 1992Date of Patent: February 23, 1993Assignee: Eastman Kodak CompanyInventor: Stephen A. Godleski
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Patent number: 5180847Abstract: A preferred process for producing 3-hydroxy-2,2,4-trimethylpentyl isobutyrate is described. The spent aqueous phase from an alkali metal hydroxide-catalyzed isobutyraldehyde condensation is concentrated in alkali metal isobutyrate salt, and the concentrated medium is introduced into a subsequent condensation to advantageously modify the isobutyraldehyde reaction. Increased conversions and productivities can thus be achieved. Preferred continuous processes, as well as preferred processes of controlled reaction duration and reactant/catalyst/salt ratios are also described. Further described is a preferred process for producing the diisobutyrate ester of 2,2,4-trimethyl-1,3-pentanediol, which in a preferred mode also achieves a desirable coproduction of the diol and its monoisobutyrate ester.Type: GrantFiled: February 15, 1991Date of Patent: January 19, 1993Assignee: BASF CorporationInventors: Laurance R. Thurman, James B. Harris
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Patent number: 5162589Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of sodium barium phosphate or potassium barium phosphate. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvent, and chemical intermediates.Type: GrantFiled: June 8, 1992Date of Patent: November 10, 1992Assignee: Shell Oil CompanyInventors: Rudolf J. Wijngaarden, Kees Latjes
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Patent number: 5149862Abstract: A process for polymerizing tetrahydrofuran to produce polytetramethylene ether glycol or ester-capped polytetramethylene ether glycol is disclosed. The reaction mass is carried out at 10.degree. to 80.degree. C. and preferably 20.degree. to 60.degree. C. In a preferred aspect of the invention, a mixture of acetic anhydride and acetic acid is present in the reaction mixture.Type: GrantFiled: February 26, 1991Date of Patent: September 22, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: Suriyanarayan Dorai, Melvin C. Baker, James A. Schultz
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Patent number: 5126493Abstract: Alkoxylates of active hydrogen compounds having a peaked molecular weight distribution are prepared by reacting the active hydrogen compound with an alkylene oxide of from 2 to 4 carbon atoms using iron oxides as alkoxylation catalysts.Type: GrantFiled: April 5, 1991Date of Patent: June 30, 1992Inventors: Wolfgang Hoelderich, Jochen Houben, Gerhard Wolf, Michael G. Kinnaird
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Patent number: 5118870Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of a xerogel comprising one or more compounds comprising a rare earth element and phorphorus. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: April 23, 1990Date of Patent: June 2, 1992Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 5104987Abstract: This invention relates to a process for the alkoxylation of an active hydrogen-containing compound comprising contacting the active hydrogen-containing compound with an alkylene carbonate in the presence of a mixed metal oxide catalyst under conditions effective to alkoxylate the active hydrogen-containing compound.Type: GrantFiled: September 20, 1990Date of Patent: April 14, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Stephen W. King
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Patent number: 5072029Abstract: The present invention relates to a process for the reaction of carboxylic acids with vinyl ethers using a non-polymeric pyridine hydrochloride and/or polymeric vinylpyridine hydrochloride as a catalyst.Type: GrantFiled: April 10, 1990Date of Patent: December 10, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventor: Walter R. Hertler
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Patent number: 5059719Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more C.sub.2 to C.sub.4 vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more soluble basic compounds of one or more elements of the lanthanum series (atomic numbers 57-71, inclusive). The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates. When the process is applied to the preparation of alkylene oxide, particularly ethylene oxide, adducts of alkanols, particularly primary alkanols in the C.sub.6 to C.sub.24 range, the product is a valuable narrow range nonionic surfactant, characterized by relatively narrow distribution of alkylene oxide adducts.Type: GrantFiled: March 23, 1990Date of Patent: October 22, 1991Assignee: Shell Oil CompanyInventor: Charles L. Edwards
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Patent number: 5057627Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more of the phosphate salts of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: February 20, 1990Date of Patent: October 15, 1991Assignee: Shell Oil CompanyInventor: Charles L. Edwards
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Patent number: 5057628Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more compounds of one or more of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: February 20, 1990Date of Patent: October 15, 1991Assignee: Shell Oil CompanyInventors: Charles L. Edwards, Richard A. Kemp
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Patent number: 5051492Abstract: A process for the preparation of a polyether resin having an epoxy group content of less than 0.2 meq/g and containing or average n/3-0.5 to n/3+2.5 primary hydroxyl groups, the process comprising reacting a glycidyl ester of a C.sub.9-11 branched aliphatic acid with an aliphatic primary polyhydric alcohol having n primary hydroxyl groups and 5 to 16 carbon atoms, n having a value of 3 to 6, in the presence of an etherification catalyst selected from a tin, zinc or iron compound.Type: GrantFiled: June 19, 1990Date of Patent: September 24, 1991Assignee: Shell Oil CompanyInventors: Olivier L. P. Andre, Henricus P. H. Scholten
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Patent number: 5026923Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more of the borate salts of the rare earth elements. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: May 29, 1990Date of Patent: June 25, 1991Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 5026903Abstract: A process for the production of ethylidene diacetate by the catalytic reaction of dimethyl acetal, methyl acetate and carbon monoxide in contact with a homogeneous catalyst system containing rhodium metal atom and lithium iodide.Type: GrantFiled: March 21, 1986Date of Patent: June 25, 1991Assignee: Union Carbide Chemicals and Plastics Technology CorporationInventor: Edgar C. Baker
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Patent number: 5015697Abstract: A process is disclosed for preparing a composition comprising a polybutyl ketone and a hydroxyester of an epoxidized polybutene wherein the epoxide groups of said epoxidized polybutene are at least 70% trisubstituted. Acid compounds are reacted with epoxidized polybutenes to obtain compositions of increased reactivity as compared with polybutyl ketone compounds. These compositions are useful as chemical intermediates to modify such materials as polyesters and polyurethenes, for applications such as coatings, foams, and sealants.Type: GrantFiled: January 31, 1989Date of Patent: May 14, 1991Assignee: Amoco CorporationInventor: Wayne T. Riddick
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Patent number: 4970295Abstract: A process for the preparation of polyethers is disclosed in which an oxetane monomer, or a mixture of an oxetane monomer and an oxolane monomer, and a carboxylic acid anhydride are contacted with a bleaching earth catalyst. The process yields ester-terminated polyethers which may be saponified to obtain hydroxy-terminated polyether polyols.Type: GrantFiled: February 27, 1989Date of Patent: November 13, 1990Assignee: ARCO Chemical Technology, Inc.Inventor: Jonathan L. Schuchardt
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Patent number: 4970333Abstract: The production of esters via the reaction of an epoxide with a carboxylic acid hasbeen shown to give improved activity when a strong base macroporous anion exchange resin having an acrylic backbone is used in place of a styrene-divinylbenzene based anion exchange resin having an equivalent exchange capacity. Excellent results are obtained when acrylic acid and propylene oxide are reacted together in the presence of strong base macroporous anion exchange resins which have an acrylic backbone.Type: GrantFiled: October 29, 1987Date of Patent: November 13, 1990Assignee: The Dow Chemical CompanyInventors: James A. Rabon, Jr., William C. Pike, Clinton J. Boriack
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Patent number: 4967016Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of the compound barium phosphate. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: January 29, 1990Date of Patent: October 30, 1990Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 4960952Abstract: Alkylene oxide adducts of organic compounds having active hydrogen atoms are prepared by a process which comprises contacting and reacting an alkylene oxide reactant comprising one or more vicinal alkylene oxides with an active hydrogen containing reactant comprising one or more compounds having active hydrogen atoms in the presence of a catalytically effective amount of one or more lanthanum compounds comprising silicate, metasilicate and mixtures thereof. The product alkoxylates are known to be useful, for instance, as nonionic surfactants, wetting and emulsifying agents, solvents, and chemical intermediates.Type: GrantFiled: August 31, 1989Date of Patent: October 2, 1990Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 4843170Abstract: A process is disclosed for producing vinyl acetate from methanol, carbon monoxide and hydrogen which comprises the following five steps:(a) methanol is hydrocarbonylated in a hydrocarbonylation zone to produce ethanol, acetaldehyde, methyl acetate and dimethylacetal, and the products are separated in a separation zone;(b) methyl acetate is carbonylated in a carbonylation zone to produce acetic anhydride;(c) the acetaldehyde and dimethylacetal produced in the step (a) and the acetic anhydride produced in the step (b) are converted to ethylidene diacetate and methyl acetate; (d) the ethylidene diacetate produced in the step (c) is thermally decomposed to vinyl acetate and acetic acid, and the products are separated in a separation zone; and(e) the methyl acetate produced and separated in the step (a), (c) or (d) is supplied to the carbonylation step (b).Type: GrantFiled: February 15, 1983Date of Patent: June 27, 1989Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tomiya Isshiki, Yasuhiko Kijima, Akira Ito, Kenji Ishii
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Patent number: 4803299Abstract: Polytetramethylene ether glycol diesters having a low color number are prepared by catalytic polymerization of tetrahydrofuran in the presence of a carboxylic anhydride, a bleaching earth and from 2 to 0.2% by weight, based on the tetrahydrofuran, of an alkylene oxide.Type: GrantFiled: April 6, 1987Date of Patent: February 7, 1989Assignee: BASF AktiengesellschaftInventor: Herbert Mueller
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Patent number: 4780565Abstract: Alkylene glycol ether carboxylates are produced by reacting at elevated temperature an alkylene oxide and a carboxylate ester in the presence as catalyst of a [bis(trihydrocarbylphosphine)iminium].sub.2 MO.sub.4 compound wherein M is either molybdenum or tungsten.Type: GrantFiled: March 4, 1987Date of Patent: October 25, 1988Assignee: BP Chemicals LimitedInventor: John E. Hamlin
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Patent number: 4749808Abstract: The invention relates to the use of metal cation-exchangeable layered clays in organic reactions which are catalysed by protons in which intercalated water is not a stoichiometric reactant. Such organic reactions include the production of esters by the reaction of an olefin or an olefin oxide with a carboxylic acid, the production of ethers by reaction of an alcohol with an olefin or an olefin oxide, the production of ethers by the reaction of a primary or secondary aliphatic alcohol or an olefin oxide, the production of bis-sec-alkyl ethers from alkenes, the production of alkyl aromatic compounds by the reaction of an aromatic hydrocarbon with an olefin or alcohol and the production of alcohols by the hydration of olefins.Type: GrantFiled: June 18, 1986Date of Patent: June 7, 1988Assignee: British Petroleum Company p.l.c.Inventors: James A. Ballantine, John H. Purnell, John M. Thomas
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Patent number: 4734521Abstract: .beta.,.gamma.-Unsaturated non-epoxide ethers react with carboxylic acids, carbamates or sulfonamides to form the corresponding .beta.,.gamma.-unsaturated esters, carbamates or sulfonamides. The reaction is catalyzed with sulfonated polystyrene beads and is promoted by copper (I) chloride.Type: GrantFiled: August 5, 1987Date of Patent: March 29, 1988Assignee: The Dow Chemical CompanyInventor: Kevin A. Frazier
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Patent number: 4727199Abstract: Active-hydrogen compounds, for example, primary and secondary alcohols or diols, are alkoxylated, for example, ethoxylated, using solid anion-bound metal oxide catalysts, such as, zirconium oxysulfate catalyst. Hydrous zicronium oxide is treated with solutions of sulfate phosphate, nitrate or tetrafluoroborate and calcined in air at 300.degree. to 950.degree. C. to produce highly active heterogeneous alkoxylation catalysts. The amorphous catalysts afford narrow molecular weight products. The catalyst can be removed from the product by filtration and reused with no significant loss in activity. Reaction temperatures of 50.degree. to 140.degree. C. are employed for alkoxylation.Type: GrantFiled: July 10, 1985Date of Patent: February 23, 1988Assignee: Union Carbide CorporationInventor: Stephen W. King
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Patent number: 4722811Abstract: An improved process for preparing glycol monoesters is provided which comprises reacting an alkylene oxide with a substantially hindered carboxylic acid in the presence of a hydroxy alkyl amine catalyst.Type: GrantFiled: July 21, 1986Date of Patent: February 2, 1988Assignee: Exxon Research & Engineering Co.Inventor: Allen D. Godwin
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Patent number: 4699998Abstract: Glycol ether esters can be prepared by reaction of an epoxide with an ester of a carboxylic acid using an amidine catalyst. The reaction can be used, for example, to prepare methoxypropyl acetate propylene oxide and methyl acetate. By carrying the reaction out in the presence of an alcohol solvent the corresponding glycol ether is also formed.Type: GrantFiled: September 4, 1984Date of Patent: October 13, 1987Assignee: BP Chemicals LimitedInventor: Michael J. Green