Preparing Esters From Acid Or From Nitrile And Diol Patents (Class 560/94)
  • Patent number: 7772417
    Abstract: Supported heterogeneous organotin catalysts of the formula X1, X2, or X3: wherein Z is a spacer group; Y is an insoluble phenyl-group containing copolymer; R1, R2, R3, R5, and R6 are independently selected from halogen, alkyl, alkylene, phenyl, vinyl, allyl, naphthyl, aralkyl, and Z; and R4 is alkyl, alkylene, phenyl, vinyl, allyl, naphthyl, or aralkyl.
    Type: Grant
    Filed: February 19, 2010
    Date of Patent: August 10, 2010
    Assignee: Chemtura Corporation
    Inventors: Uwe Schneider, Bernard Jousseaume, Karine Darriet, Thierry Toupance
  • Patent number: 6100374
    Abstract: The process for preparing polyethylene naphthalate according to the invention is intended to obtain polyethylene naphthalate having a low impurity content from naphthalenedicarboxylic acid containing impurities.
    Type: Grant
    Filed: March 9, 1999
    Date of Patent: August 8, 2000
    Assignee: Mitsui Chemicals Inc.
    Inventors: Hiroshi Iwasaki, Satoshi Inoki, Hiromi Ueki
  • Patent number: 5847070
    Abstract: New compounds including bis-.beta.-hydroxy ethyl bibenzoate containing less than 2.5%, and preferably less than 1%, diethylene glycol and a process for the production of the bis-.beta.-hydroxy ethyl bibenzoate by the condensation of 4,4'-biphenyl dicarboxylic acid and ethylene glycol at low temperature and pressure in the presence of a catalyst are disclosed. Use of the compounds to produce polyesters is also disclosed.
    Type: Grant
    Filed: December 1, 1994
    Date of Patent: December 8, 1998
    Assignee: Monsanto Company
    Inventors: Jawed Asrar, David J. Weinkauff, A. Hameed Bhombal
  • Patent number: 5455025
    Abstract: Non-aqueous compositions for topical application comprising one or more active ingredients and a fatty alkoxylate ester emollient agent comprising a diester or triester of an aliphatic or aromatic tricarboxylic acid formed by reacting the acid with a stoichiometric excess of one or more polyalkoxylated fatty alcohols.
    Type: Grant
    Filed: April 12, 1994
    Date of Patent: October 3, 1995
    Assignee: Croda, Inc.
    Inventors: Abel G. Pereira, Kevin F. Gallagher, Phillip G. Abend, John C. Carson, Jr.
  • Patent number: 5364956
    Abstract: The compound described in the present invention is represented by the following general formula: R.sub.1 (OCH.sub.2 CH.sub.2).sub.n O(COACOOXO).sub.m COACO(OCH.sub.2 CH.sub.2).sub.k OR.sub.2 wherein A is C.sub.2 -C.sub.4 alkylene group or a residual group of aromatic dicarboxylic acid, namely a group formed by removing two carboxylic groups from an aromatic dicarboxylic acid,X is straight or branched chain alkylene group, a residual group of glycols (namely a group formed by removing two hydroxyl groups from a glycol) selected from the group consisting of diethylene glycol, triethylene glycol, dipropylene glycol, and tripropylene glycol, or a residual group of thiodiethanol,n is 1 to 3,R.sub.1 is selected from the group consisting of C.sub.1 -C.sub.10 alkyl or benzyl,R.sub.2 is C.sub.1 -C.sub.8 alkyl or benzyl,m is 0 to 13 andk is 0 to 3.
    Type: Grant
    Filed: November 18, 1992
    Date of Patent: November 15, 1994
    Inventor: Satoshi Matsumoto
  • Patent number: 5302377
    Abstract: Fatty alkoxylate esters which are diesters or triesters of an aliphatic or aromatic dicarboxylic or tricarboxylic acid formed by reacting the acid with a stoichiometric excess of one or more polyalkoxylated fatty alcohols. Compositions for topical application are also disclosed including one or more active ingredients, water and an emollient agent of the fatty alkoxylate esters of the present invention.
    Type: Grant
    Filed: April 2, 1992
    Date of Patent: April 12, 1994
    Assignee: Croda, Inc.
    Inventors: Abel G. Pereira, Kevin F. Gallagher, Phillip G. Abend, John C. Carson, Jr.
  • Patent number: 5243013
    Abstract: The new polyester polyols, which have an acid value below 10, a hydroxyl value of 50 to 200, a hydroxyl functionality above 2 and a number average molecular weight M.sub.n of 800 to 5,000 and which are liquid at C. or are homogeneously soluble in di-2-ethylhexyl phthalate in a concentration of at least 70% by weight, the viscosity of the 70% solution being from 1 to 35 Pa.s, are used as anchoring agents for polymer systems and as polymeric plasticizers.
    Type: Grant
    Filed: April 27, 1992
    Date of Patent: September 7, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Helmut Hurnik, Gerhard Trummelmeyer, Adolf Winkler
  • Patent number: 5204454
    Abstract: Prepolymer polyols containing mesogenic moieties useful as reactants for the preparation of resinous materials are disclosed. Synthesized by condensing a polyether polyol with bifunctional mesogenic diacids, or diesters, the compounds of the invention are characterized by their reasonably low melt temperature which renders them suitable as additive materials in polymeric molding compositions and as precursors for the preparation of resinous materials.The liquid crystalline properties of the prepolymers of the invention were found to depend on the type and molecular weight of the glycols and on the molar ratio between the glycols and the mesogenic reactant.
    Type: Grant
    Filed: July 19, 1991
    Date of Patent: April 20, 1993
    Assignee: Miles Inc.
    Inventors: Randall A. Rodenhouse, Dittmar K. Nerger, Douglas A. Wicks
  • Patent number: 5015759
    Abstract: A process for increasing the direct esterification reaction rate between a diacid and 1,4-butanediol and for directly esterifying greater than 95% of the acid ends of the diacid by mixing in any order the diacid, the 1,4-butanediol and a catalyst compound selected from organo-titanium, organo-tin, and organo-zirconium compounds, to form a reaction mixture wherein the ratio of diol:diacid is at least 2:1 and then reacting the reaction mixture at an average temperature ranging between C. to C. for a period of time no longer than sixty minutes. The same process may be followed substituting ethylene glycol for 1,4-butanediol, provided the catalyst compound is added neat, further provided that the average reaction temperature ranges from C. to C., and also provided that the reaction mixture be reacted for a period of time no longer than seventy minutes.
    Type: Grant
    Filed: December 8, 1989
    Date of Patent: May 14, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: David J. Lowe
  • Patent number: 4745211
    Abstract: A process for preparation of a purified bis(2-hydroxyethyl) ester of 2,6-naphthalenedicarboxylic acid wherein 2,6-naphthalenedicarboxylic acid is reacted with a catalyst comprised of a tertiary amine and a titanium-containing compound in order to produce the ester.
    Type: Grant
    Filed: September 15, 1987
    Date of Patent: May 17, 1988
    Assignee: Eastman Kodak Company
    Inventors: Winston J. Jackson, Jr., Thomas H. Wicker, Jr.
  • Patent number: 4681975
    Abstract: A polyester being liquid at C. comprises a polybasic acid and a polyhydric alcohol as its monomer constituents, wherein the polyhydric alcohol is composed at least partially of 1,2-butanediol.
    Type: Grant
    Filed: March 13, 1986
    Date of Patent: July 21, 1987
    Assignee: Mitsubishi Monsanto Chemical Company
    Inventors: Ryuichi Hasegawa, Kohji Hayashi
  • Patent number: 4670580
    Abstract: The invention provides a process for the preparation of a polyester oligomer capable of being further polymerized to a high polymer wherein a glycol-dicarboxylic acid ester feed is treated in a secondary esterification zone under conditions such that the partial vapor pressures of water and glycol are maintained at a cumulative level of less than 740 Torr, with water and glycol vapors being continuously removed from the secondary esterification zone, and free glycol being added to the secondary esterification zone in an amount sufficient to maintain a stable amount of liquid glycol in the secondary esterification zone.
    Type: Grant
    Filed: March 31, 1986
    Date of Patent: June 2, 1987
    Assignee: Celanese Corporation
    Inventor: Charles J. Maurer
  • Patent number: 4615822
    Abstract: A new and highly useful resin prepolymer blend of (a) polyester polyols prepared by esterifying phthalic anhydride bottoms with aliphatic polyols; (b) aliphatic polyol, (c) compatibilizing polyalkoxylated compound, and (d) (optionally) polyalkoxylated amine or amide diol. This blend can be reacted with organic isocyanates in the presence of fluorocarbon blowing agent and preferably catalysts to produce cellular polymeric structures.
    Type: Grant
    Filed: March 13, 1985
    Date of Patent: October 7, 1986
    Assignee: Stepan Company
    Inventor: George Magnus
  • Patent number: 4596886
    Abstract: A polyester being liquid at C. comprises a polybasic acid and a polyhydric alcohol as its monomer constituents, wherein the polyhydric alcohol is composed at least partially of 1,2-butanediol.
    Type: Grant
    Filed: March 23, 1983
    Date of Patent: June 24, 1986
    Assignee: Mitsubishi Monsanto Chemical Company
    Inventors: Ryuichi Hasegawa, Kohji Hayashi
  • Patent number: 4585889
    Abstract: The present invention provides a process for the preparation of monoesters of dicarboxylic acids by the carbonylation of carboxyphenyl-triarylphosphonium salts. The carboxyphenyl-triarylphosphonium salts are reacted with carbon monoxide and an alcohol in a base reaction medium having a pK.sub.b greater than about 8.
    Type: Grant
    Filed: January 28, 1985
    Date of Patent: April 29, 1986
    Assignee: Eastman Kodak Company
    Inventors: Carl M. Lentz, James R. Overton, David D. Cornell
  • Patent number: 4560788
    Abstract: A process for producing an oligoester which comprises:(a) the step of reacting isophthalic acid and propylene oxide in a reaction medium in the presence of a specific catalyst comprising a tetraalkyl ammonium compound to prepare an oligoester, and(b) the step of removing volatile components from the resulting oligoester by heating the oligoester at a temperature of C. is disclosed. The oligoester is used as an intermediate for preparing unsaturated polyesters.
    Type: Grant
    Filed: August 8, 1983
    Date of Patent: December 24, 1985
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Akira Miyamoto, Senzo Shimizu, Masayoshi Okamura, Hiroka Tanisake, Yasumitsu Higuchi, Toshio Hidaka, Koji Yamamoto, Toshiyuki Abe
  • Patent number: 4511708
    Abstract: Polytetramethylene terephthalate is manufactured from terephthalic acid and 1,4-butanediol in two stages, a first stage comprising an esterification reaction employing an esterification catalyst and a second stage comprising a condensation-polymerization reaction. The esterification reaction is carried out in the presence of at least one acid amide compound, preferably selected from urea, a derivative thereof, mono- or poly-carboxylic acid amides having 1 to 9 carbon atoms, polyamides, phosphoric acid amides and sulfonic acid amides, whereby the production of tetrahydrofuran as a by-product is appreciably inhibited and the time required for the esterification reaction is reduced.
    Type: Grant
    Filed: January 31, 1984
    Date of Patent: April 16, 1985
    Assignee: Polyplastics Company, Ltd.
    Inventors: Takuzo Kasuga, Katsuhiko Takahashi, Kunio Suzuki
  • Patent number: 4506090
    Abstract: Mixtures of aromatic polyols containing ester functionalities suitable for use as polyol extenders in rigid foams prepared by reacting aromatic carbonyl-containing compounds with an alkylene glycol, the reaction product of which is reacted with recycled polyethylene terephthalate are described. Surprisingly, the process is non-catalytic. These novel polyols may be blended with conventional polyols to yield excellent rigid foams, thus serving as useful polyol extenders.
    Type: Grant
    Filed: July 15, 1983
    Date of Patent: March 19, 1985
    Assignee: Texaco Inc.
    Inventors: Michael E. Brennan, George P. Speranza
  • Patent number: 4506091
    Abstract: A process for preparing esters which comprises reacting a polycarboxylic acid with an excess of alcohol and in the presence of an organotitanate catalyst, treating the crude mixture with a suitable chelate compound, removing the unreacted alcohol and hydrolyzing the treated titanium catalyst residues with steam, and recovering the purified ester by filtration.
    Type: Grant
    Filed: September 1, 1983
    Date of Patent: March 19, 1985
    Inventor: Donald L. Deardorff
  • Patent number: 4450112
    Abstract: Reaction of a nitrile, an alcohol and water in the presence of a catalyst comprising rhodium, iridium or platinum complexed with hydroxo and tertiary phosphine moieties, to produce the corresponding carboxylic ester.
    Type: Grant
    Filed: November 25, 1981
    Date of Patent: May 22, 1984
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Stanley S. Wreford
  • Patent number: 4374263
    Abstract: The invention relates to an esterification process employing as a heterogeneous catalyst an inorganic oxide, e.g. silica, to which there is bonded by reaction with surface hydroxyl groups a sulphonic acid-functionalized silane.
    Type: Grant
    Filed: October 24, 1980
    Date of Patent: February 15, 1983
    Assignee: The British Petroleum Company Limited
    Inventors: Ronald D. Hancock, Robert Mackison
  • Patent number: 4365054
    Abstract: A glycol and terephthalic and other aromatic acids are esterified using alkali metal titanates as catalysts and the catalysts are used in polymerization of the ester.
    Type: Grant
    Filed: August 11, 1975
    Date of Patent: December 21, 1982
    Assignee: The Firestone Tire & Rubber Company
    Inventor: Bernard D. Stabley, Jr.
  • Patent number: 4365078
    Abstract: This invention concerns a method of charging dry terephthalic acid into a reactor which may contain glycol and be under elevated pressure and elevated temperature. According to the invention a suspension of terephthalic acid in a gas such as nitrogen is formed and this suspension is charged into the reactor.
    Type: Grant
    Filed: May 14, 1979
    Date of Patent: December 21, 1982
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Lawrence E. Shelley
  • Patent number: 4346229
    Abstract: Described is a process for producing unique reaction products from DMT process residue. In the process of this invention DMT process residue is reacted with an excess of dipropylene glycol to give normally liquid, aromatic polyester polyols which are compatible with Freon 11 blowing agent and with glycerol and hence have outstanding utility in the production of blown polyurethane and polyisocyanurate-polyurethane foams.
    Type: Grant
    Filed: May 1, 1980
    Date of Patent: August 24, 1982
    Assignee: Hercules Incorporated
    Inventors: Leighton K. Derr, Lyle B. Hawkins, Marlene J. Jones
  • Patent number: 4204070
    Abstract: A process for preparing bis(hydroxyethyl)terephthalate and its low molecular weight oligomers in a reactor equipped with a rectifying column which comprises suspending or dissolving terephthalic acid in molten bis(hydroxyethyl)terephthalate and its low molecular weight oligomers at a temperature above the dew point of ethylene glycol and feeding gaseous or liquid ethylene glycol into the suspension or the solution to react it with the terephthalic acid, where the amount of ethylene glycol fed into the reactor is controlled so as to maintain the temperature inside the rectifying column at a temperature at which the ethylene glycol does not substantially distill off from the rectifying column and the partial pressure of the ethylene glycol is maximized.
    Type: Grant
    Filed: April 23, 1976
    Date of Patent: May 20, 1980
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Fumiyuki Suzuki, Toshimitu Okutu, Keitaro Ohe
  • Patent number: 4146729
    Abstract: A continuous process is disclosed for direct esterification of terephthalic acid with ethylene glycol to form low molecular weight polyester with recovery of excess glycol from reaction off-gases. The terephthalic acid is mixed with an excess of glycol, the mixture is reacted at C. in reaction product circulated from a reactor through an external heater and back to the reactor, and reaction product is withdrawn from the reactor for polymerization to high molecular weight polyester. Vapors formed in the reactor are fed into the bottom of a rectification column where the excess glycol is recovered for direct reuse. The vapor feed is sprayed with condensate at C. in the bottom of the column to remove solids and maintain conditions suitable for obtaining less than 0.05 percent glycol in overhead distillate and 0.3 to 10 percent water in glycol condensate.
    Type: Grant
    Filed: April 7, 1977
    Date of Patent: March 27, 1979
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: George R. Goodley, Donald A. Shiffler
  • Patent number: 4097468
    Abstract: In a process for the preparation of high molecular weight linear polyesters of terephthalic acid which comprises partially esterifying terephthalic acid with an alkylene glycol under direct esterification conditions and then further esterifying and polycondensing the partially esterified product, the molecular weight distribution of the polyester is narrowed by correlating the carboxyl conversion with the reacted glycol to terephthalic acid mol ratio in various steps of a multistep process.
    Type: Grant
    Filed: March 15, 1977
    Date of Patent: June 27, 1978
    Assignee: Allied Chemical Corporation
    Inventors: Leonard Evans James, Laszlo Joseph Balint, Stanley David Lazarus
  • Patent number: 4096124
    Abstract: Terephthalic acid is esterified with an alkylene glycol by heating in a first stage one mole of the acid with at least about 1.2 moles of the glycol and 0.01 to 1.0% based on the weight of the acid of a volatile organic base at a temperature between and C and at a pressure above the vapor pressure of the glycol at the reaction temperature until about 75-85% of the acid groups initially present in the terephthalic acid have been esterified, and then maintaining the reaction mixtures from the first stage in a second stage at a temperature between to at a pressure less than that of the said first stage until at least about 95% of the acid groups initially present in the terephthalic acid have been esterified.
    Type: Grant
    Filed: January 12, 1976
    Date of Patent: June 20, 1978
    Assignee: Mobil Oil Corporation
    Inventors: William C. L. Wu, Raymond Eichenbaum