Oxirane Containing Reactant Patents (Class 554/149)
  • Patent number: 6531443
    Abstract: Improved modified monoethanolamide composition mixtures are provided which may be represented by the formula Wherein: R is an optionally substituted or unsubstituted, branched or straight chain, saturated or unsaturated hydrocarbon radical of 3-21 carbon atoms; B is CH3 or —CH2—CH3; and x is at least about 1. wherein the modified monoethanolamide compositions, which are liquid at ambient temperatures or lower, exhibit surfactant properties substantially the same as those exhibited by diethanolamides such as foam stabilization and viscosity building as well as other desirable characteristics.
    Type: Grant
    Filed: February 26, 2001
    Date of Patent: March 11, 2003
    Assignee: Mona Industries, Inc.
    Inventors: James E. Perella, Joseph A. Komor, Dennis L. Fost, Richard D. Katstra
  • Patent number: 6429324
    Abstract: Processes for preparing alkylene glycol esters of dimer fatty acids according to the general formula (I): H—(OR)n—O(O)C—R1—C(O)O—(RO)n—H  (I) wherein R1 represents a hydrocarbon radical of a dimer fatty acid having from about 24 to about 44 carbon atoms, and each R independently represents an alkyl radical having from about 2 to about 3 carbon atoms, and each n independently represents a number of from about 0.25 to about 3.0, are described. The processes include: (a) providing dimer fatty acids; (b) providing an alkylene oxide; and (c) reacting the dimer fatty acids and the alkylene oxide, in the presence of a catalytically-effective amount of at least one alkanolamine.
    Type: Grant
    Filed: August 18, 2000
    Date of Patent: August 6, 2002
    Assignee: Cognis Deutschland and GmbH
    Inventors: Hans-Christian Raths, Frank Bongardt, Ansgar Behler, Juergen Roeder
  • Patent number: 6380410
    Abstract: Fatty acid derivatives based on epoxidized unsaturated fatty acid esters or triglycerides and reacted with amines such as hydroxy- and/or amino-substituted hydrophilic amines or amino acids and/or with alkanols or with water on the epoxy group and/or the carboxylic ester groups are described. These fatty amides are suitable as surfactants in detergents and cleaners.
    Type: Grant
    Filed: October 25, 1999
    Date of Patent: April 30, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Alfred Oftring, Martin aus dem Kahmen, Christian Ott, Günter Oetter, Richard Baur
  • Patent number: 6372927
    Abstract: The process for preparing an alkylene oxide adduct, including the steps of feeding an organic compound having active hydrogen and an alkylene oxide to a reaction column packed with a solid catalyst, and carrying out addition reaction of the organic compound having active hydrogen with an alkylene oxide in a gas-liquid fixed bed reaction, wherein the alkylene oxide is in a state of gas and the organic compound having active hydrogen is in a state of liquid.
    Type: Grant
    Filed: August 10, 1998
    Date of Patent: April 16, 2002
    Assignee: Kao Corporation
    Inventors: Nobuhiro Tatsumi, Yoshikazu Ogura, Takanobu Katayama, Osamu Tabata
  • Publication number: 20020010350
    Abstract: The process for preparing an alkylene oxide adduct, including the steps of feeding an organic compound having active hydrogen and an alkylene oxide to a reaction column packed with a solid catalyst, and carrying out addition reaction of the organic compound having active hydrogen with an alkylene oxide in a gas-liquid fixed bed reaction, wherein the alkylene oxide is in a state of gas and the organic compound having active hydrogen is in a state of liquid.
    Type: Application
    Filed: August 10, 1998
    Publication date: January 24, 2002
    Inventors: NOBUHIRO TATSUMI, YOSHIKAZU OGURA, TAKANOBU KATAYAMA, OSAMU TABATA
  • Patent number: 6300508
    Abstract: Fatty acid esters of alkylene glycols corresponding to the formula R1COO(AlkO)nH are thickeners for aqueous surfactant solutions, particularly for personal care products.
    Type: Grant
    Filed: June 30, 1998
    Date of Patent: October 9, 2001
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Hans-Christian Raths, Norman Milstein, Werner Seipel
  • Patent number: 6274750
    Abstract: Mixtures of dimeric and trimeric fatty acid C1-4 alkyl esters and processes for their preparation comprising either A) epoxidizing an unsaturated or partially hydrogenated fatty acid glyceride; B) transesterifying the epoxidized glyceride with a C1-4 alkanol to obtain epoxidized fatty acid C1-4 alkyl esters; and C) ring opening and dimerizing the epoxidized fatty acid C1-4 alkyl esters; or A) transesterifying an unsaturated or partially hydrogenated glyceride with a C1-4 alkanol to obtain olefinically unsaturated fatty acid C1-4 alkyl esters; B) epoxidizing the unsaturated fatty acid C1-4 alkyl esters; and C) ring opening and dimerizing the epoxidized fatty acid C1-4 alkyl esters.
    Type: Grant
    Filed: July 21, 1998
    Date of Patent: August 14, 2001
    Assignee: Cognis Corporation
    Inventors: Setsuo Sato, Ramiro Carielo Bueno, Wanderson Bueno De Almeida
  • Patent number: 6201144
    Abstract: Fatty ether compounds and a process for their production is disclosed. The compounds possess low viscosity and low temperature melting point properties and may be used as viscosity modifiers in the creation of cosmetics and complete vegetable oil based biodegradable fluids such as hydraulic fluids and dielectric fluids. Formation of these fatty ether compounds is by reaction of the appropriate hydroxy fatty acid or lactone with a nucleophilic alcohol in the presence of an acid catalyst to produce fatty ether esters. Following their formation, the fatty ether esters may be recovered for subsequent use, or in the alternative, they may either be hydrolyzed to produce fatty ether acids or transesterified with a different nucleophilic alcohol in the presence of an acid catalyst to produce alternate ester variants.
    Type: Grant
    Filed: May 29, 1996
    Date of Patent: March 13, 2001
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Terry A. Isbell, Melissa S. Mund
  • Patent number: 6046344
    Abstract: A process for the preparation of hydroxypropylated quaternary ammonium compounds containing an ester functional group, preferably a fatty acid ester functional group, of formula (I): ##STR1## in which: R denotes a saturated or unsaturated, linear or branched C.sub.7 -C.sub.35 alkyl chain;R.sub.1, R.sub.2 and R.sub.3 independently denote a saturated or unsaturated, linear or branched C.sub.1 -C.sub.18 alkyl chain;X.sup.- denotes a halide or another anion chosen from: ##STR2## in which: R.sub.4 and R.sub.5 independently denote a saturated or unsaturated, linear or branched C.sub.1 -C.sub.8 alkyl chain, wherein the process comprises reacting, in a single step and in an alcoholic solvent at reflux, an aliphatic carboxylic acid (RCOOH) salt or an aliphatic carboxylic acid under basic catalysis conditions with a compound of formula (II): ##STR3## in which R.sub.1, R.sub.2, R.sub.3 and X.sup.- are defined as above.
    Type: Grant
    Filed: December 10, 1997
    Date of Patent: April 4, 2000
    Assignee: L'Oreal
    Inventors: Michel Philippe, Alain Campos
  • Patent number: 6008391
    Abstract: A process for making alkoxylated fatty acid alkyl esters involving: (a) providing a fatty acid alkyl ester; (b) providing an alkylene oxide component; (c) providing a catalyst component containing a mixture of: (i) a primary catalyst; and (ii) an alkylene glycol having from 2 to 6 carbon atoms; and (d) reacting (a)-(c) to make the alkoxylated fatty acid alkyl ester.
    Type: Grant
    Filed: September 25, 1998
    Date of Patent: December 28, 1999
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Rafael Pi Subirana, Joaquim Llosas Bigorra
  • Patent number: 6008392
    Abstract: A process for making alkoxylated fatty acid alkyl esters involving: (a) providing a fatty acid alkyl ester; (b) providing an alkylene oxide component; (c) providing a primary catalyst; (d) providing a co-catalyst selected from the group consisting of lithium hydroxide, an alkaline earth metal, a tin salt and mixtures thereof; and (e) reacting (a)-(d) to make the alkoxylated fatty acid alkyl ester.
    Type: Grant
    Filed: September 28, 1998
    Date of Patent: December 28, 1999
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Ansgar Behler, Almud Folge
  • Patent number: 6002030
    Abstract: A process is provided for the fatty acid esterification of propoxylated glycerin wherein fatty acids stripped from the esterifier and/or fatty acids stripped from the esterification product are scrubbed by contact with a scrubbing liquid which is maintained at a temperature above the fatty acid melting point.
    Type: Grant
    Filed: May 8, 1998
    Date of Patent: December 14, 1999
    Assignee: ARCO Chemical Technology, L.P.
    Inventor: Jon R. Valbert
  • Patent number: 5986117
    Abstract: A convenient method of obtaining useful esterified propoxylated glycerin fat substitutes from readily available triglycerides such as fats and oil is provided wherein a triglyceride is reacted with a propoxylated glycerin under conditions effective to remove glycerin during such reaction.
    Type: Grant
    Filed: June 18, 1997
    Date of Patent: November 16, 1999
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Charles F. Cooper
  • Patent number: 5936107
    Abstract: Fatty acid polyethylene glycol esters of the formula (I):R.sup.1 CO(CH.sub.2 CH.sub.2 O).sub.n H (I)wherein R.sup.1 CO is a linear or branched, aliphatic, saturated and/or unsaturated acyl group having from about 6 to about 22 carbon atoms and n is a number from 0.5 to 1.5 are made by reacting ethylene oxide and a fatty acid in the presence of an alkanolamine in a homogeneous reaction medium.
    Type: Grant
    Filed: December 9, 1996
    Date of Patent: August 10, 1999
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Hans-Christian Raths, Ansgar Behler, Norman Milstein
  • Patent number: 5872269
    Abstract: Economics of heat are achieved in a process for batch fatty acid esterification of alkoxylated polyol by transferring the reaction mixture to a holding vessel and subsequently heating fresh feed to the batch reaction by indirect heat exchange with the transferred reaction mixture.
    Type: Grant
    Filed: May 8, 1998
    Date of Patent: February 16, 1999
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Gary A. Sawyer
  • Patent number: 5849935
    Abstract: An improved process for the production of high yields of .delta.-lactones and 5-hydroxy fatty acids from unsaturated fatty acids which are free or esterified with glycerol is disclosed. The .delta.-lactones may be produced by reacting one or more .DELTA..sup.5 or .DELTA..sup.6 unsaturated fatty acids in the presence of an acid, clay or zeolite catalyst. Alternatively, the .delta.-lactones may be produced by reacting one or more triglycerides which are esters of glycerol with .DELTA..sup.5 or .DELTA..sup.6 unsaturated fatty acids with the same catalysts. Because the .delta.-lactones may be produced from the triglycerides of unsaturated fatty acids, the process may be practiced using naturally occurring plant oils directly, without the need for any preliminary steps of saponification. Optionally, the .delta.-lactones so formed may be further reacted with an alkali in an aqueous solution to produce 5-hydroxy fatty acids.
    Type: Grant
    Filed: September 27, 1995
    Date of Patent: December 15, 1998
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Terry A. Isbell, Beth A. Plattner, Robert Kleiman
  • Patent number: 5817844
    Abstract: A method of manufacturing a fatty acid ester of polyoxyalkylene alkyl ether wherein a fatty acid ester of polyoxyalkylene alkyl ether represented by the following formula (I) is produced through a reaction between a fatty acid alkyl ester with an alkylene oxide in the presence of a composite metal-oxide catalyst whose surface is modified with a metal hydroxide or a metal alkoxide: ##STR1## wherein each of R.sub.1 and R.sub.3 independently represents an alkyl group or an alkenyl group, R.sub.2 represents an alkylene group, and n is a positive number.
    Type: Grant
    Filed: April 8, 1996
    Date of Patent: October 6, 1998
    Assignee: Lion Corporation
    Inventors: Ituo Hama, Takahiro Okamoto, Hisashi Sasamoto, Hirofumi Nakamura
  • Patent number: 5741947
    Abstract: Alkoxylation products are prepared by reacting compounds having active hydrogen atoms with C.sub.2 -C.sub.4 -alkylene oxides in the presence of a mixed hydroxide built up of polycations and modified with additives and having the general formula I or II?M(II).sub.1-x M(III).sub.x (OH).sub.2 !A.sub.x/n .multidot.m L(I)?LiAl.sub.2 (OH).sub.6 !A.sub.1/n .multidot.m L (II)whereM(II) is at least one divalent metal ion,M(III) is at least one trivalent metal ion,A is at least one inorganic anion andL is an organic solvent or water,n is the valence of the inorganic anion A or in the case of a plurality of anions A is their mean valence andx can assume a value of from 0.1 to 0.5 andm can assume a value of from 0 to 10,as alkoxylation catalyst, wherein the mixed hydroxide contains additives.
    Type: Grant
    Filed: January 29, 1996
    Date of Patent: April 21, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Wolf, Bernd Burkhart, Guenter Lauth, Horst Trapp, Alfred Oftring
  • Patent number: 5646320
    Abstract: Fatty acid esters of isethionate salts are made by reacting ethylene oxide and a bisulfite salt, that may be made in situ, in aqueous ammonia while maintaining (1) the pH in the range of about 5.5 to about 6.5 and (2) the temperature in the range of 25.degree. C. to 85.degree. C. to form an isethionate salt. The isethionate salt is then esterified with a fatty acid to produce a product having little or no unwanted fatty acid esters of ethylene glycol.
    Type: Grant
    Filed: June 16, 1994
    Date of Patent: July 8, 1997
    Assignee: Henkel Corporation
    Inventors: Timothy John Cassady, Norman Milstein, Richard P. Crews
  • Patent number: 5576451
    Abstract: Esters of fatty acids with ethoxylated polyols are prepared by (a) ethoxylating polyols in the presence of basic catalysts at high temperatures with 80 to 150 moles ethylene oxide per mol polyol and then (b) reacting the reaction product with 1 to 1.3 moles fatty acids per mole of hydroxyl groups contained in the original polyol, in the presence of acid catalysts. These esters are useful as thickeners of aqueous solutions of surface active agents.
    Type: Grant
    Filed: May 13, 1994
    Date of Patent: November 19, 1996
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Antonio Trius Oliva, Oriol Ponsati Obiols, Joaquim Bigorra Llosas, Esther Prat Queralt
  • Patent number: 5571935
    Abstract: Esterified alkoxylated polyols, particularly a fatty acid-esterified propoxylated glycerol, which exhibit improved flavor and oxidative stability by the addition of antioxidants to the alkoxylated polyols, either prior to or subsequent to steam stripping, fatty acids or combinations thereof prior to fatty acid esterification, and the products thereof.
    Type: Grant
    Filed: January 14, 1994
    Date of Patent: November 5, 1996
    Assignee: CPC International Inc.
    Inventors: Bernard C. Sekula, Thaddeus R. Ziegert, Michael R. Ferenz
  • Patent number: 5539135
    Abstract: Hydrophobicized double-layer hydroxide compounds may be produced if double-layer hydroxide compounds of the general formula (I): [M.sup.(II).sub.1-x M.sup.(III).sub.x (OH).sub.2 ] A.sub.x.n H.sub.2 O, in which M.sup.(II) is a divalent metal cation, M.sup.(III) is a trivalent metal cation, A is an equivalent of a monobasic and/or multibasic inorganic acid, x is a number from 0.2 to 0.5 and n is a number from 0 to 10, are reacted at elevated temperature and under autogenous pressure with at least one carboxylic acid or its salt and the reaction product is then dried. The hydrophobicized double-layer hydroxide compounds obtained by this process are suitable as catalysts for the alkoxylation of compounds with active hydrogen atoms or of fatty acid esters.
    Type: Grant
    Filed: October 4, 1993
    Date of Patent: July 23, 1996
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Wolfgang Breuer, Claudia Mai, Hans-Christian Raths, Elvira Scholz
  • Patent number: 5523431
    Abstract: The present application relates to a method of producing an amide product mixture having a low content of secondary amines by reacting an amide product mixture having a high secondary amine content with an aliphatic alkylene oxide in the absence of an essential amount of any alkoxylation catalyst. The amide product mixture obtained contains a minor amount of tertiary amines and exhibits advantageous properties when used for the formulation of cosmetic products, such as shampoos and creams; foam cleaning compositions, e.g. for textiles and cars; and functional fluids, such as lubricants, metal working fluids and hydraulic fluids.
    Type: Grant
    Filed: October 29, 1993
    Date of Patent: June 4, 1996
    Assignees: Berol Nobel AB, Castrol Ltd.
    Inventor: Rolf Skold
  • Patent number: 5519154
    Abstract: A process for producing ethoxylated ester surfactants in high yield has been discovered which employs no halogen-containing reactants or intermediates. Allyl alcohol is reacted with ethylene oxide to give an allyl alcohol ethoxylate; the ethoxylate in turn is reacted with a bisulfite salt (e.g. sodium metabisulfite) to give an ethylene glycol propanesulfonate or polyethylene glycol propanesulfonate in high yield. The propanesulfonate is then reacted with a fatty acid to give the ethoxylated ester surfactant.
    Type: Grant
    Filed: January 10, 1994
    Date of Patent: May 21, 1996
    Assignee: Huntsman Corporation
    Inventor: Carter G. Naylor
  • Patent number: 5514368
    Abstract: The invention is a process for hydrophilicizing a mixture of triglycerides and glycerol by ethoxylation of the mixture followed by sulfonation with sulfur trioxide and neutralization.
    Type: Grant
    Filed: June 17, 1994
    Date of Patent: May 7, 1996
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Frank Wangemann, Hans-Christian Raths, Rudolf Zauns-Huber
  • Patent number: 5512313
    Abstract: Reduced calorie food compositions are prepared using fatty acid esterified alkoxylated polyol fat substitutes derived from C.sub.3 and higher epoxides and having a high proportion of primary ester linkages. The fat substitutes may be obtained by alkoxylation of a polyol such as glycerin with the epoxide in the presence of a cationic/ring-opening polymerization catalyst, followed by esterification with a fatty acid or a fatty acid equivalent.
    Type: Grant
    Filed: December 8, 1994
    Date of Patent: April 30, 1996
    Assignees: ARCO Chemical Technology, L.P., CPC International Inc.
    Inventors: Charles F. Cooper, Stephen H. Harris
  • Patent number: 5466843
    Abstract: Esterified alkoxylated polyols containing long chain saturated linear acyl groups are obtained by esterification of an alkoxylated polyol such as propoxylated glycerin with a C.sub.12 -C.sub.24 fatty acid such as behenic acid and recovery of excess fatty acid by treatment with an aliphatic hydrocarbon. Esterified alkoxylated polyols prepared in this manner are useful fat substitutes for the formulation of reduced calorie food products.
    Type: Grant
    Filed: April 29, 1994
    Date of Patent: November 14, 1995
    Assignee: ARCO Chemical Technology, L.P.
    Inventor: Charles F. Cooper
  • Patent number: 5442082
    Abstract: The invention relates to alkoxylated compounds prepared by reaction of epoxidized C.sub.10-22 carboxylic acid derivatives with C.sub.2-4 alkylene oxides in the presence of alkoxylation catalysts and mono- and/or polyhydric alcohols.
    Type: Grant
    Filed: December 16, 1994
    Date of Patent: August 15, 1995
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Guenter Uphues, Uwe Ploog, Peter Daute, Gerhard Stoll, Berthold Schreck
  • Patent number: 5399729
    Abstract: Reduced calorie food compositions are prepared using fatty acid esterified alkoxylated polyol fat substitutes derived from C.sub.3 and higher epoxides and having a high proportion of primary ester linkages. The fat substitutes may be obtained by alkoxylation of a polyol such as glycerin with the epoxide in the presence of a cationic/ring-opening polymerization catalyst, followed by esterification with a fatty acid or a fatty acid equivalent.
    Type: Grant
    Filed: August 31, 1993
    Date of Patent: March 21, 1995
    Assignees: Arco Chemical Technology, L.P., CPC International Inc.
    Inventors: Charles F. Cooper, Stephen H. Harris
  • Patent number: 5399728
    Abstract: A convenient method of obtaining useful highly esterified alkoxylated polyol fat substitutes from readily available triglycerides such as fats and oils is provided.
    Type: Grant
    Filed: April 5, 1993
    Date of Patent: March 21, 1995
    Assignees: ARCO Chemical Technology, L.P., CPC International Inc.
    Inventor: Charles F. Cooper
  • Patent number: 5391784
    Abstract: The present invention relates to derivatives of natural fats and oils that are liquid or flowable, respectively, and to a process for the production of said derivatives, in which oxalkylation is carried out at elevated temperatures in the presence of basic catalysts with at least one compound containing an epoxide group, and sulfation is carried out in a manner known per se, in which a starting material containingA) at least one C.sub.8 -C.sub.24 -fatty acid ester of an aliphatic C.sub.1 -C.sub.5 -monoalcoholThe present invention furthermore relates to the use of said derivatives, optionally in combination with other greasing substances and anionic and/or non-ionic emulsifiers, for the fatliquoring and greasing of leather.
    Type: Grant
    Filed: December 6, 1993
    Date of Patent: February 21, 1995
    Assignee: Chemische Fabrik Stockhausen GmbH
    Inventors: Helmut Brehn, Helmut Klimmek, Leonhard Strijbos
  • Patent number: 5386045
    Abstract: A process for producing alkoxylated mono-, di-, and tri-esters in which a starting material ester and an alkylene oxide are reacted in the presence of selected calcium based catalysts.
    Type: Grant
    Filed: August 5, 1992
    Date of Patent: January 31, 1995
    Assignee: Vista Chemical Company
    Inventors: Upali Weerasooriya, Donald T. Robertson, John Lin, Bruce E. Leach, Cynthia L. Aeschbacher, Tonyette S. Sandoval
  • Patent number: 5374750
    Abstract: In a method of manufacturing fatty acid esters of polyoxyalkylene alkyl ethers, fatty acid alkyl ester is reacted with alkylene oxide in the presence of a catalyst consisting essentially of a magnesium oxide added with at least one metal ion selected from the group consisting of Al.sup.3+, Ga.sup.3+, In.sup.3+, Tl.sup.3+, Co.sup.3+, Sc.sup.3+, La.sup.3+, and Mn.sup.2+ to manufacture a compound having the following formula: ##STR1## wherein each of R.sub.1 and R.sub.3 independently represents an alkyl group, R.sub.2 represents an alkylene group, and n is a positive integer.
    Type: Grant
    Filed: September 1, 1993
    Date of Patent: December 20, 1994
    Assignee: Lion Corporation
    Inventors: Hirofumi Nakamura, Itsuo Hama, Yuji Fujimori, Yuichi Nakamoto
  • Patent number: 5371251
    Abstract: The invention relates to fatty acid monoglyceride polyglycol ether sulfosuccinates of the general formula ##STR1## where R represents a straight-chain or branched alkyl or alkylene group having from 7 to 21 carbon atoms;R.sup.1 represents H or CO--R;R.sup.2 may represent, independently of each other, H or the group --CO--CH(SO.sub.3.sup.- M.sup.+)--CH.sub.2 --COO.sup.- M.sup.+ ;A represents the same or different and each is an alkylene group having from 2 to 3 carbon atoms;a,b,c,d may be the same or different, from 0 to 5,e being from 1 to 3,f is a multiplication product of c times e, and a+b+f+d is from 2 to 25; andM.sup.+ represents an alkali-metal ion or an ammonium ion, and to their preparation and use.
    Type: Grant
    Filed: October 5, 1992
    Date of Patent: December 6, 1994
    Assignee: Witco GmbH
    Inventors: Ingo Hamann, Elke Hohn, Hans-Jurgen Kohle
  • Patent number: 5371253
    Abstract: Esterified alkoxylated mono- and diglycerides suitable for use as reduced calorie fat substitutes in food products may be produced by alkoxylating a tertiary alkyl partial ether of glycerin with an epoxide and then reacting the alkoxylated glycerin tertiary alkyl partial ether thereby obtained with a fatty acid under acid-catalyzed conditions. Separate deprotection and esterification steps are not required, resulting in a considerably streamlined process as compared to alternative methods of synthesizing alkoxylated fat substitutes having one or two fatty acid acyl groups attached directly to glycerin.
    Type: Grant
    Filed: December 14, 1993
    Date of Patent: December 6, 1994
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Charles F. Cooper
  • Patent number: 5362894
    Abstract: A method of obtaining a fatty acid-esterified alkoxylated polyol useful as a reduced calorie fat substitute is provided. The method utilizes a C.sub.1 -C.sub.4 alkyl ester of a C.sub.8 -C.sub.24 fatty acid such as methyl stearate or methyl oleate and a short chain acid-esterified alkoxylated polyol such as the acetate of propoxylated glycerin as reactants.
    Type: Grant
    Filed: November 12, 1993
    Date of Patent: November 8, 1994
    Assignees: Arco Chemical Technology, L.P., CPC International, Inc.
    Inventors: Beth M. Handwerker, Charles F. Cooper, Bernard C. Sekula
  • Patent number: 5324846
    Abstract: The present invention relates to a partial ester derived from the reaction product of an oxirane containing acid or derivative thereof, and a reactive hydroxyl compound selected from the group consisting of diols, triols, di-diols and 1,4-dihydroxy butane and a halogen containing polymer compositon thereof. The oxirane compound can be derived from the group consisting of epoxidized vegetable oil, epoxidized fish oil, an aliphatic or arylaliphatic containing craboxyl compound having an oxirane group in the aliphatic chain.
    Type: Grant
    Filed: January 30, 1992
    Date of Patent: June 28, 1994
    Assignee: Elf Atochem North America, Inc.
    Inventors: Justin L. Hirshman, Dana S. Garcia, Mohammad R. Kazemizadeh
  • Patent number: 5304665
    Abstract: A convenient method of obtaining useful highly esterified alkoxylated polyol fat substitutes from readily available triglycerides such as fats and oils is provided.
    Type: Grant
    Filed: April 5, 1993
    Date of Patent: April 19, 1994
    Assignees: Arco Chemical Technology, L.P., CPC International, Inc.
    Inventors: Charles F. Cooper, Bernard C. Sekula, Stephen D. Harper
  • Patent number: 5292910
    Abstract: A process for the catalyzed ethoxylation or propoxylation of compounds selected from the group consisting of organic compounds containing active H atoms, esters of fatty acids containing 2 to 22 carbon atoms with monoalkanols containing 1-22 carbon atoms with polyols containing 2 to 12 carbon atoms and 2 to 6 hydroxyl groups, wherein the improvement comprises the use as catalyst for the ethoxylation or propoxylation of hydrophobicized hydrotalcites corresponding to the general formula I:Mg.sub.x Al(OH).sub.y (CO.sub.3).sub.m (A).sub.n.zH.sub.2 O (I),in which A is selected from the group consisting of (i) a dianion of an aliphatic dicarboxylic acid containing 4 to 44 carbon atoms and (ii) two anions of aliphatic monocarboxylic acids containing 2 to 34 carbon atoms; 1<x<5; y.ltoreq.2x+2; {y+2(m+n)}=2x+3; m+n.ltoreq.0.5; m.gtoreq.0; and 0<z<10.
    Type: Grant
    Filed: December 2, 1992
    Date of Patent: March 8, 1994
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Hans-Christian Raths, Wolfgang Breuer, Klaus Friedrich, Klaus Herrmann
  • Patent number: 5266714
    Abstract: Process for the preparation of ester polyols by conducting the ring opening of epoxidized esters and/or alcohols with carboxylic acids by the controlled addition of the epoxidized compounds to the carboxylic acids wherein the carboxylic acids are present in at least stoichiometric quantities based on epoxide groups, to minimize unreacted epoxide groups and produce ester polyols having relatively low viscosities compared to those produced by the one-pot prior art process.
    Type: Grant
    Filed: April 21, 1992
    Date of Patent: November 30, 1993
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Gerhard Stoll, Peter Daute, Rainer Hoefer, Roland Gruetzmacher, Hermann Kluth
  • Patent number: 5245062
    Abstract: Ketone compounds are obtained by rearrangement of epoxides in the presence of iodide ions providing quaternary ammonium and phosphonium salts, optionally in admixture with alkali metal or alkaline earth metal iodides, are used as the rearrangement catalysts.
    Type: Grant
    Filed: July 20, 1992
    Date of Patent: September 14, 1993
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Gerhard Stoll, Elke Grundt
  • Patent number: 5237080
    Abstract: Alkoxylation products of at least one of ethylene oxide, propylene oxide, and butylene oxide and at least one C.sub.10-22 carboxylic acid mono-, di-, or tri-glyceride which is of natural origin or is obtained from natural origin wherein in the 9, 10 position, the 13, 14 position, or in both positions of the carboxylic acid the following unit is present ##STR1## in which R is a hydrogen atom, an OH group or an OR.sup.1 group,R.sup.1 is a C.sub.9-18 alkyl group, a C.sub.9-18 alkenyl group or a ##STR2## group, and R.sup.2 is a hydrogen atom, a C.sub.1-21 alkyl group or a C.sub.2-21 alkenyl group.The invention also relates to compositions containing the above alkoxylation products in place of alkoxylated castor oil normally present in the compositions, and to a process for preparing the alkoxylation products.
    Type: Grant
    Filed: January 14, 1992
    Date of Patent: August 17, 1993
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Peter Daute, Gerhard Stoll
  • Patent number: 5220046
    Abstract: A process for producing alkoxylated methyl esters to produce a narrow homolog distribution of the alkoxylate species in which a staring material methyl ester and an alkylene oxide are reacted in the presence of selected calcium based catalysts.
    Type: Grant
    Filed: August 22, 1991
    Date of Patent: June 15, 1993
    Assignee: Vista Chemical Company
    Inventors: Bruce E. Leach, John Lin, Cynthia L. Aeschbacher, Donald T. Robertson, Tonyette S. Sandoval, Upali Weerasooriya
  • 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: 5194641
    Abstract: Alkoxidation products are prepared from amines, fatty acids and oils, which are low in alkylene oxides and 1,4-dioxane by reacting an amine, fatty acid, ester or oil with an alkylene oxide in the presence of a catalyst of an alkali fatty alkoxide obtained by reaction of an alkali hydroxide with a fatty alcohol at elevated temperature.
    Type: Grant
    Filed: May 9, 1991
    Date of Patent: March 16, 1993
    Assignee: Huels Aktiengesellschaft
    Inventors: Egbert Schroer, Klaus Schulze, Ekkehard Wienhofer
  • Patent number: 5175374
    Abstract: The invention relates to a process for the separation of colloidal barium phosphate or colloidal barium sodium phosphate, used as a heterogeneous catalyst in the alkoxylation of an active hydrogen containing organic compound, from the alkoxylated product, which process comprises contacting the alkoxylated product with an amount of water sufficient to break the colloidal state of the barium phosphate or barium sodium phosphate, and collecting the phosphate.
    Type: Grant
    Filed: June 29, 1992
    Date of Patent: December 29, 1992
    Assignee: Shell Oil Company
    Inventors: Rudolf J. Wijngaarden, Kees Latjes, Jan Van Schaik
  • Patent number: 5164124
    Abstract: Alkaline earth salts of vicinally hydroxy, alkoxy-substituted C.sub.16 -C.sub.22 fatty acids corresponding to the following general formula ##STR1## in which R represents linear or branched alkyl or alkenyl groups or hydroxyalkyl groups optionally alkylated with a C.sub.16 -C.sub.22 fatty acid, process for their preparation, and their use as catalysts. These salts give a narrow homolog distribution of the polyalkoxylation products in the catalysis of the polyalkoxylation of compounds containing active hydrogen atoms.
    Type: Grant
    Filed: February 24, 1988
    Date of Patent: November 17, 1992
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Fritz Lange, Bert Gruber, Alfred Meffert, Ansgar Behler
  • 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: 5159092
    Abstract: An alkylene oxide is reacted in a loop reactor with an organic compound having a reactive hydrogen atom, a gas circulation and a liquid circulation around the reactor being provided and being coupled with one another via an ejector mixing nozzle. To ensure completeness of the reaction and suppression of the formation of by-products such as dioxane, it is essential to reduce the temperature of the entire alkylene oxide gas phase to a temperature below that of the liquid phase, and this is effected by feeding and evaporating liquid alkylene oxide and by cooling of the gas phase on the unit walls.
    Type: Grant
    Filed: September 12, 1990
    Date of Patent: October 27, 1992
    Assignee: Buss AG
    Inventor: Gunter M. Leuteritz
  • 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