Preparing Esters From Ethers Patents (Class 560/240)
  • Patent number: 5852208
    Abstract: 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: Grant
    Filed: August 30, 1996
    Date of Patent: December 22, 1998
    Assignee: Dixie Chemical Company, Inc.
    Inventor: Joseph C. Rongione
  • Patent number: 5773648
    Abstract: 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: Grant
    Filed: March 7, 1997
    Date of Patent: June 30, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Becker, Christoph Sigwart, Michael Hesse, Rolf Fischer, Karsten Eller, Gerd Heilen, Klaus-Dieter Plitzko
  • Patent number: 5684179
    Abstract: 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: Grant
    Filed: December 14, 1995
    Date of Patent: November 4, 1997
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Suriyanarayan Dorai
  • Patent number: 5663422
    Abstract: 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: Grant
    Filed: March 1, 1996
    Date of Patent: September 2, 1997
    Assignee: Eastman Chemical Company
    Inventors: Steven Thomas Perri, Stephen Neal Falling
  • Patent number: 5659073
    Abstract: 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: Grant
    Filed: July 7, 1995
    Date of Patent: August 19, 1997
    Inventor: Jian Steven Qi
  • Patent number: 5659068
    Abstract: 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: Grant
    Filed: May 31, 1994
    Date of Patent: August 19, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Juergen Weyer, Rolf Fischer, Gerhard Jeschek, Herbert Mueller
  • Patent number: 5648558
    Abstract: 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: Grant
    Filed: March 16, 1994
    Date of Patent: July 15, 1997
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Masakatsu Hatano, Akio Nakanishi, Yoshio Kabata, Masayuki Shirado, Hiroshi Takeo, Mitsuharu Kobayashi
  • Patent number: 5641857
    Abstract: 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: Grant
    Filed: November 7, 1995
    Date of Patent: June 24, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Roman Dostalek, Rolf Fischer, Ulrich Mueller, Rainer Becker
  • Patent number: 5623086
    Abstract: 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: Grant
    Filed: December 29, 1995
    Date of Patent: April 22, 1997
    Assignee: Eastman Chemical Company
    Inventors: Steven T. Perri, Stephen N. Falling
  • Patent number: 5463020
    Abstract: 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: Grant
    Filed: June 30, 1994
    Date of Patent: October 31, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Becker, Michael Huellmann, Christof Palm, Wolfgang Franzischka
  • Patent number: 5416240
    Abstract: 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: Grant
    Filed: March 2, 1993
    Date of Patent: May 16, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Juergen Weyer, Rolf Fischer, Gerhard Jeschek, Franz Merger, Herbert Mueller
  • Patent number: 5371276
    Abstract: 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: Grant
    Filed: November 24, 1993
    Date of Patent: December 6, 1994
    Assignee: Industrial Technology Research Institute
    Inventors: Shiao-Jung Chu, Fu-Chen Liu, Ching-Tang Lin, Huey-Jiuan Yeh, Fu-Hsi Yu
  • Patent number: 5344964
    Abstract: 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: Grant
    Filed: November 24, 1993
    Date of Patent: September 6, 1994
    Assignee: Industrial Technology Research Institute
    Inventors: Shiao-Jung Chu, Fu-Chen Liu, Ching-Tang Lin, Wen-Fa Lin, Kuei-Chih Wang, Sheng-Te Yang
  • Patent number: 5298650
    Abstract: 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: Grant
    Filed: April 15, 1992
    Date of Patent: March 29, 1994
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Francis J. Waller, William F. Burgoyne, Jr.
  • Patent number: 5262562
    Abstract: 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: Grant
    Filed: February 14, 1992
    Date of Patent: November 16, 1993
    Assignee: Texaco Chemical Company
    Inventors: Donald R. Hollingsworth, John F. Knifton
  • Patent number: 5254723
    Abstract: 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: Grant
    Filed: November 23, 1992
    Date of Patent: October 19, 1993
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Lau S. Yang, Diane A. Macarevich
  • Patent number: 5225590
    Abstract: Intermediates and methods for producing intermediates for use in preparing 9-(1,3-dihydroxy-2-propoxymethyl)-guanine and esters and ethers thereof.
    Type: Grant
    Filed: April 26, 1988
    Date of Patent: July 6, 1993
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: David J. Morgans, Jr., Harlan H. Chapman
  • Patent number: 5218141
    Abstract: 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: Grant
    Filed: November 6, 1991
    Date of Patent: June 8, 1993
    Assignee: BASF Aktiengesellschaft
    Inventor: Herbert Mueller
  • Patent number: 5214200
    Abstract: 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: Grant
    Filed: April 15, 1992
    Date of Patent: May 25, 1993
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Francis J. Waller
  • Patent number: 5210325
    Abstract: 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: Grant
    Filed: August 10, 1992
    Date of Patent: May 11, 1993
    Assignee: Shell Oil Company
    Inventors: Richard A. Kemp, Paul R. Weider
  • Patent number: 5210283
    Abstract: 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: Grant
    Filed: May 18, 1992
    Date of Patent: May 11, 1993
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Andrew P. Kahn, Robert G. Gastinger, Gangfeng Cai
  • Patent number: 5208385
    Abstract: 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: Grant
    Filed: February 19, 1992
    Date of Patent: May 4, 1993
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Andrew P. Kahn, Robert G. Gastinger, Rangasamy Pitchai
  • Patent number: 5202463
    Abstract: 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: Grant
    Filed: September 10, 1991
    Date of Patent: April 13, 1993
    Assignee: ARCO Chemical Technology, L.P.
    Inventor: Jude T. Ruszkay
  • Patent number: 5189199
    Abstract: 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: Grant
    Filed: February 20, 1992
    Date of Patent: February 23, 1993
    Assignee: Eastman Kodak Company
    Inventor: Stephen A. Godleski
  • Patent number: 5180847
    Abstract: 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: Grant
    Filed: February 15, 1991
    Date of Patent: January 19, 1993
    Assignee: BASF Corporation
    Inventors: Laurance R. Thurman, James B. Harris
  • Patent number: 5162589
    Abstract: 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: Grant
    Filed: June 8, 1992
    Date of Patent: November 10, 1992
    Assignee: Shell Oil Company
    Inventors: Rudolf J. Wijngaarden, Kees Latjes
  • Patent number: 5149862
    Abstract: 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: Grant
    Filed: February 26, 1991
    Date of Patent: September 22, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Suriyanarayan Dorai, Melvin C. Baker, James A. Schultz
  • Patent number: 5126493
    Abstract: 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: Grant
    Filed: April 5, 1991
    Date of Patent: June 30, 1992
    Inventors: Wolfgang Hoelderich, Jochen Houben, Gerhard Wolf, Michael G. Kinnaird
  • Patent number: 5118870
    Abstract: 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: Grant
    Filed: April 23, 1990
    Date of Patent: June 2, 1992
    Assignee: Shell Oil Company
    Inventor: Richard A. Kemp
  • Patent number: 5104987
    Abstract: 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: Grant
    Filed: September 20, 1990
    Date of Patent: April 14, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Stephen W. King
  • Patent number: 5072029
    Abstract: 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: Grant
    Filed: April 10, 1990
    Date of Patent: December 10, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Walter R. Hertler
  • Patent number: 5059719
    Abstract: 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: Grant
    Filed: March 23, 1990
    Date of Patent: October 22, 1991
    Assignee: Shell Oil Company
    Inventor: Charles L. Edwards
  • Patent number: 5057627
    Abstract: 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: Grant
    Filed: February 20, 1990
    Date of Patent: October 15, 1991
    Assignee: Shell Oil Company
    Inventor: Charles L. Edwards
  • Patent number: 5057628
    Abstract: 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: Grant
    Filed: February 20, 1990
    Date of Patent: October 15, 1991
    Assignee: Shell Oil Company
    Inventors: Charles L. Edwards, Richard A. Kemp
  • Patent number: 5051492
    Abstract: 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: Grant
    Filed: June 19, 1990
    Date of Patent: September 24, 1991
    Assignee: Shell Oil Company
    Inventors: Olivier L. P. Andre, Henricus P. H. Scholten
  • Patent number: 5026923
    Abstract: 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: Grant
    Filed: May 29, 1990
    Date of Patent: June 25, 1991
    Assignee: Shell Oil Company
    Inventor: Richard A. Kemp
  • Patent number: 5026903
    Abstract: 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: Grant
    Filed: March 21, 1986
    Date of Patent: June 25, 1991
    Assignee: Union Carbide Chemicals and Plastics Technology Corporation
    Inventor: Edgar C. Baker
  • Patent number: 5015697
    Abstract: 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: Grant
    Filed: January 31, 1989
    Date of Patent: May 14, 1991
    Assignee: Amoco Corporation
    Inventor: Wayne T. Riddick
  • Patent number: 4970295
    Abstract: 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: Grant
    Filed: February 27, 1989
    Date of Patent: November 13, 1990
    Assignee: ARCO Chemical Technology, Inc.
    Inventor: Jonathan L. Schuchardt
  • Patent number: 4970333
    Abstract: 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: Grant
    Filed: October 29, 1987
    Date of Patent: November 13, 1990
    Assignee: The Dow Chemical Company
    Inventors: James A. Rabon, Jr., William C. Pike, Clinton J. Boriack
  • Patent number: 4967016
    Abstract: 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: Grant
    Filed: January 29, 1990
    Date of Patent: October 30, 1990
    Assignee: Shell Oil Company
    Inventor: Richard A. Kemp
  • Patent number: 4960952
    Abstract: 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: Grant
    Filed: August 31, 1989
    Date of Patent: October 2, 1990
    Assignee: Shell Oil Company
    Inventor: Richard A. Kemp
  • Patent number: 4843170
    Abstract: 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: Grant
    Filed: February 15, 1983
    Date of Patent: June 27, 1989
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tomiya Isshiki, Yasuhiko Kijima, Akira Ito, Kenji Ishii
  • Patent number: 4803299
    Abstract: 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: Grant
    Filed: April 6, 1987
    Date of Patent: February 7, 1989
    Assignee: BASF Aktiengesellschaft
    Inventor: Herbert Mueller
  • Patent number: 4780565
    Abstract: 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: Grant
    Filed: March 4, 1987
    Date of Patent: October 25, 1988
    Assignee: BP Chemicals Limited
    Inventor: John E. Hamlin
  • Patent number: 4749808
    Abstract: 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: Grant
    Filed: June 18, 1986
    Date of Patent: June 7, 1988
    Assignee: British Petroleum Company p.l.c.
    Inventors: James A. Ballantine, John H. Purnell, John M. Thomas
  • Patent number: 4734521
    Abstract: .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: Grant
    Filed: August 5, 1987
    Date of Patent: March 29, 1988
    Assignee: The Dow Chemical Company
    Inventor: Kevin A. Frazier
  • Patent number: 4727199
    Abstract: 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: Grant
    Filed: July 10, 1985
    Date of Patent: February 23, 1988
    Assignee: Union Carbide Corporation
    Inventor: Stephen W. King
  • Patent number: 4722811
    Abstract: 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: Grant
    Filed: July 21, 1986
    Date of Patent: February 2, 1988
    Assignee: Exxon Research & Engineering Co.
    Inventor: Allen D. Godwin
  • Patent number: 4699998
    Abstract: 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: Grant
    Filed: September 4, 1984
    Date of Patent: October 13, 1987
    Assignee: BP Chemicals Limited
    Inventor: Michael J. Green