From Polyhydroxy Containing Compound Patents (Class 568/619)
  • Patent number: 6620975
    Abstract: Processes are described for the preparation of glycol butyl ethers involving reaction of butadiene with saturated aliphatic glycols, separating the thus formed n- and sec-butenyl glycol ethers and hydrogenating the n-butenyl glycol ethers. Additional features are the use in the first step of heterogeneous catalyst modified by alkylpyridinium quaternary ammonium, quaternary arsonium quaternary phosphonium counterions and/or the conversion of sec-butenyl glycol ethers to butadiene and saturated aliphatic glycols.
    Type: Grant
    Filed: April 30, 2001
    Date of Patent: September 16, 2003
    Assignee: BP Chemicals Limited
    Inventor: Benjamin Patrick Gracey
  • Patent number: 6608230
    Abstract: A single-stage method for producing &agr;-hydroxy ethers by oxidizing olefinic substrates with organic hydroperoxides and opening the resultant oxirane ring by means of monovalent or polyvalent alcohols wherein a molybdenum compound in combination with a compound selected from the group consisting of boron trifluoride, aluminum oxides, 1,8-diazabicyclo-[5.4.0]-undec-7-ene or 1,4-diazabicyclo-[2.2.2]-octane, and mixtures thereof is used as a catalyst system.
    Type: Grant
    Filed: November 8, 2001
    Date of Patent: August 19, 2003
    Assignee: WE-DEA Aktiengesellschaft für Mineraloel und Chemie
    Inventors: Mark Rüsch gen. Klaas, Siegfried Warwel, Hans-Martin Zillmann, Klaus Kwetkat
  • Patent number: 6593376
    Abstract: A process for preparing amphiphilic compounds having at least two hydrophilic and at least two hydrophobic groups by reacting an olefinic substrate having at least two double bonds with an organic hydroperoxide to form an oxirane ring, opening, the oxirane ring with an alcohol in the presence of a catalyst system comprising a molybdenum compound as a first catalyst component and a second catalyst component selected from the group consisting of boron trifluoride, alumina, 1,8-diazzabicyclo-(5.4.0)-undec-7-ene, 1,4-diazabicyclo-(2,2,2)-octane.
    Type: Grant
    Filed: December 30, 1999
    Date of Patent: July 15, 2003
    Assignee: SASOL Germany GmbH
    Inventors: Mark Rüsch gen. Klaas, Klaus Kwetkat, Siegfried Warwel
  • Patent number: 6570041
    Abstract: Disclosed is a high heat resistance and low viscosity polyoxytetramethylene glycol (PTMG) having the following characteristics (1) to (4): (1) a number average molecular weight of from 500 to 3000; (2) a molecular weight distribution of 1.8 or less in terms of the Mw/Mn ratio; (3) a content of high molecular weight PTMG molecules of from 2 to 5% by weight, wherein the high molecular weight PTMG molecules are PTMG molecules having molecular weights which are at least six times as large as the number average molecular weight of all PTMG molecules; and (4) a heteropolyacid content of from 10 to 900 ppb by weight.
    Type: Grant
    Filed: January 22, 2002
    Date of Patent: May 27, 2003
    Assignee: Asahi Kasei Kabushiki Kaisha
    Inventors: Tamotsu Kodama, Takeshi Mori, Takaharu Akedo
  • Patent number: 6566563
    Abstract: A process for making OH-terminated compounds involving: (a) combining at least one CH2OH-terminated diol and a titanium-containing catalyst to form a reaction mixture; (b) heating the reaction mixture to a temperature of from 110 to 160° C. to form a heated reaction mixture; (c) continuously adding dimethyl carbonate to the heated reaction mixture; (d) continuously distilling all methanol released from the heated reaction mixture; (e) heating the reaction mixture to a temperature of from 190 to 240° C. to form an OH-terminated product; (f) removing unreleased methanol and dimethyl carbonate from the reaction mixture under a pressure of less than 100 mbar; and (g) deactivating the titanium-containing catalyst by adding from 0.8 to 2 equivalents, based on the catalyst, of a 1 to 20% by weight aqueous solution of phosphoric acid to the reaction mixture, at a temperature of from 80 to 120° C.
    Type: Grant
    Filed: May 4, 2001
    Date of Patent: May 20, 2003
    Assignee: Cognis Deutschland GmbH & Co. KG
    Inventors: Alfred Westfechtel, Roland Gruetzmacher, Elke Grundt
  • Patent number: 6555717
    Abstract: Secondary alcohols, specifically diols and polyols, are dehydroxylated to the corresponding primary alcohols using a homogeneous organometallic ruthenium complex catalyst.
    Type: Grant
    Filed: June 20, 2001
    Date of Patent: April 29, 2003
    Assignees: E. I. du Pont de Nemours and Company, Brookhaven Science Associates
    Inventors: R. Morris Bullock, Marcel Schlaf, Paul Joseph Fagan, Elisabeth M. Hauptman
  • Patent number: 6540942
    Abstract: Nonaqueous compositions comprising at least one product of the reaction between A) a linking agent of formula I R4(Y)3  (I) Wherein each Y group is a halogen atom or one Y group is a halogen atom and two Y groups represent an epoxy oxygen atom, which is attached to two adjacent carbon atoms in the R4 group to form an epoxy group, and R4 is an alkanetriyl group containing from 3 to 10 carbon atoms; and B) a compound of formula II R3(EO)n(PO)m(BO)pX  (II) Wherein R3 is substituted or unsubstituted, saturated or unsaturated, organic oxy or thio group having from 1 to 36 carbon atoms or a primary or secondary amino group having from 1 to 36 carbon atoms; n is a number of from 0 to 50; m is a number of from 0 to 50; p is a number of from 0 to 50; and X is hydrogen, or X can be a mercapto group, an amino group, or a C1-C6 alkylamino group in place of a terminal —OH group, provided that when X is mercapto, amino or a C1-C6 alkylamino, the sum of n, m, and p must be at least 1; and the
    Type: Grant
    Filed: October 15, 2001
    Date of Patent: April 1, 2003
    Assignee: Cognis Corporation
    Inventors: Miguel A. Dones, Ramesh L. Narayan
  • Patent number: 6512146
    Abstract: Improved water resistant acetal sizing agents including 1,1-octadecoxyoctadecane are provided along with methods for their synthesis including methods in which C8 to C30 alkyl bromides are reacted with a polyol under basic conditions and those in which a C8 to C30 primary alcohol is reacted with an organic base in the presence of a suitable oxidizing agent under basic conditions.
    Type: Grant
    Filed: December 20, 2000
    Date of Patent: January 28, 2003
    Assignee: Penford Corporation
    Inventors: Edward P. Pauley, Katherine Sue Neighbor
  • Patent number: 6504061
    Abstract: The present invention provides an alkoxylation solid catalyst with which an alkylene oxide adduct having a narrow adduct distribution can be produced while inhibiting formation of high molecular weight polyalkylene glycol having a molecular weight of about tens of thousands as a by-product. The alkoxylation catalyst comprises a metal oxide containing magnesium, aluminum, and at least one metal selected from the metals that belong to group VIA, group VIIA, and group VIII as a third component. The third component metal changes the structure of the active site in the catalyst, for example, by forming a metal oxide having a spinel-type structure with aluminum (e.g. when the third component metal is Mn, MnAl2O4 is formed), so that a side reaction of forming a high molecular weight polyalkylene glycol is inhibited.
    Type: Grant
    Filed: November 17, 2000
    Date of Patent: January 7, 2003
    Assignee: Lion Corporation
    Inventors: Takahiro Okamoto, Shingo Uemura, Itsuo Hama
  • Patent number: 6492565
    Abstract: The present invention relates to a process for the preparation of polyether polyols by the reaction of alkylene oxides and compounds containing active hydrogens, in the presence of specific Lewis acid metal compounds as catalysts, novel bis(perfluoroalkylsulfonic acid) compounds of Group 13 of the Periodic Table of the Elements, and to a process for the preparation thereof and the use thereof as catalysts for ring-opening polymerization of cyclic ethers.
    Type: Grant
    Filed: April 6, 2001
    Date of Patent: December 10, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Denninger, Jörg Hofmann, Pramod Gupta
  • Patent number: 6482993
    Abstract: This invention relates to a process for the production of long-chain polyether polyols without working up, in which oligomeric, alkoxylated starter compounds having molecular weights of 200 to 1000 are first obtained by catalysis with perfluoroalkylsulfonates of the metals of group III A of the periodic system of elements (in accordance with the IUPAC convention of 1970) from low molecular weight starters by reaction with alkylene oxides at reaction temperatures of 80 to 200° C. and catalyst concentrations of 5 to 200 ppm, which oligomeric, alkoxylated starter compounds are then converted without working up and removal of the catalyst by means of highly active DMC catalysts at a catalyst concentration of 30 ppm or below, relative to the quantity of polyether polyol to be produced, by reaction with alkylene oxides into higher molecular weight, long-chain polyether polyols.
    Type: Grant
    Filed: October 18, 2000
    Date of Patent: November 19, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jörg Hofmann, Pramod Gupta
  • Patent number: 6479689
    Abstract: A method for continuously producing a dialkyl carbonate and a diol, comprising: (1) continuously feeding a cyclic carbonate and an aliphatic monohydric alcohol to a continuous multi-stage distillation column, and continuously effecting a transesterification between the cyclic carbonate and the aliphatic monohydric alcohol in the presence of a transesterification catalyst in the distillation column, while continuously withdrawing a low boiling point mixture in a gaseous form containing the produced dialkyl carbonate and the unreacted aliphatic monohydric alcohol from an upper portion of the distillation column and continuously withdrawing a high boiling point mixture in a liquid form containing the produced diol and the unreacted cyclic carbonate from a lower portion of the distillation column, and (2) continuously feeding the high boiling point mixture withdrawn from the lower portion of the distillation column to a continuous etherification reactor, to thereby effect a continuous etherification reaction betw
    Type: Grant
    Filed: June 11, 2001
    Date of Patent: November 12, 2002
    Assignee: Asahi Kasei Kabushiki Kaisha
    Inventors: Masahiro Tojo, Kazuhiro Oonishi
  • Patent number: 6465605
    Abstract: Polymeric compounds useful as low foaming surfactants and defoaming and stabilizing agents for aqueous-and nonaqueous-based compositions, and to processes for the preparation of the polymeric compounds, wherein the polymeric compounds are the reaction products of reactants comprising A) at least one linking compound of formula I R1(X)3  (I) wherein each X group is a halogen atom or one X group is a halogen atom and two X groups represent an epoxy oxygen atom, which is attached to two adjacent carbon atoms in the R1 group to form an epoxy group, and R1 is an alkanetriyl group containing from 3 to 10 carbon atoms; and B) compounds of formula 11 R2(OA)nX  (II) wherein R2 is an organic group containing from 4 to 36 carbon atoms, n is a number of from 0 to 200, X is —OH, —NHR′, or —SH and each OA group is independently an ethyleneoxy, 1,2-propyleneoxy, or 1,2-butyleneoxy group.
    Type: Grant
    Filed: February 15, 2001
    Date of Patent: October 15, 2002
    Assignee: Cognis Corporation
    Inventors: Kenneth Breindel, Ronald W. Broadbent, Michael S. Wiggins, Marcie Natale
  • Publication number: 20020115577
    Abstract: A refrigerating machine oil for a carbon dioxide refrigerant according to the invention is a refrigerating machine oil comprising polyalkylene glycol represented by the following general formula (1):
    Type: Application
    Filed: October 16, 2001
    Publication date: August 22, 2002
    Inventors: Tomomasa Ohsumi, Katsuya Takigawa
  • Patent number: 6429342
    Abstract: Ethoxylations of various initiator compounds are performed in the presence of metal cyanide catalysts. The catalysts surprisingly form a wide variety of polyether products that in most cases contain only small amounts of high molecular weight poly(ethylene oxide).
    Type: Grant
    Filed: July 7, 2000
    Date of Patent: August 6, 2002
    Assignee: Dow Global Technologies Inc.
    Inventors: Katherine S. Clement, Louis L. Walker, Richard M. Wehmeyer, Robert H. Whitmarsh, David C. Molzahn, William P. Dianis, David E. Laycock
  • Patent number: 6410801
    Abstract: A continuous alkoxylation process for the production of polyether polyols is disclosed. The process comprises the use of a plurality of reaction modules each having an outer tube and an inner tube with annular chamber between them. A spiral reaction tube is spaced from the inner tube and winds around the inner tube within the annular chamber. The spiral reaction tube includes an inlet and an outlet, each of which extend through said outer tube. A heat exchange medium flows through the annular chamber and controls the reaction temperature in the spiral reaction tube. The process comprises continuously forming an initial reaction mixture of at least one alkylene oxide and an initiator having at least one reactive hydrogen which is reactive to the alkylene oxide.
    Type: Grant
    Filed: November 18, 1999
    Date of Patent: June 25, 2002
    Assignee: BASF Corporation
    Inventors: Werner Hinz, Edward Michael Dexheimer
  • Patent number: 6395938
    Abstract: A method for controlling the molecular weight distribution of polyether glycol in producing polyether glycol having a specified number average molecular weight by polymerizing tetrahydrofuran as a starting monomer with the use of a heteropoly-acid as a catalyst, which method comprises conducting the polymerization in the presence of an amount of water which can form two phases of the organic phase and a catalyst phase, sampling the polymerization product during the polymerization to determine the molecular weight distribution and, when the molecular weight distribution thus found is narrower than the specified molecular weight distribution, making the residence time distribution of the starting monomer in the catalyst phase wider, while, when the found molecular weight distribution is wider than the specified molecular weight distribution, making the residence time distribution of the starting monomer in the catalyst phase narrower.
    Type: Grant
    Filed: November 22, 2000
    Date of Patent: May 28, 2002
    Assignee: Asahi Kasei Kabushiki Kaisha
    Inventor: Takaharu Akedo
  • Patent number: 6380439
    Abstract: A single-stage method for producing &agr;-hydroxy ethers by oxidizing olefinic substrates with organic hydroperoxides and opening the resultant oxirane ring by means of monovalent or polyvalent alcohols wherein a molybdenum compound in combination with a compound selected from the group consisting of boron trifluoride, aluminum oxides, 1,8-diazabicyclo-[5.4.0]-undec-7-ene or 1,4-diazabicyclo-[2.2.2]-octane, and mixtures thereof is used as a catalyst system.
    Type: Grant
    Filed: January 25, 2000
    Date of Patent: April 30, 2002
    Assignee: RWE-DEA Aktiengesellschaft fur Mineraloel und Chemie
    Inventors: Mark Rüsch gen. Klaas, Siegfried Warwel, Hans-Martin Zillmann, Klaus Kwetkat
  • Patent number: 6365541
    Abstract: An alkoxylation catalyst is prepared by a) reaction of one mol of a dicarboxylic acid with from 1.5 to 8 mol of an alkoxylated alcohol to form the corresponding dicarboxylic monoester, b) formation of an alkaline earth metal salt of the dicarboxylic monoester by addition of water and from 0.45 to 0.55 mol of a basic alkaline earth metal compound per mol of dicarboxylic acid originally used, c) partial neutralization of the alkaline earth metal salt by addition of from 0.25 to 0.7 mol of H2SO4 per mol of basic alkaline earth metal compound originally used and d) removal of the water present at a temperature of less than 100° C. The catalyst prepared in this way makes it possible to prepare colorless alkoxylates having a narrow homologue distribution.
    Type: Grant
    Filed: February 25, 1999
    Date of Patent: April 2, 2002
    Assignee: Clariant GmbH
    Inventors: Ignaz Wimmer, Hildegard Freundl
  • Patent number: 6355846
    Abstract: A process for producing a poly(tetramethylene ether) glycol (PTMEG) or copolymer having a narrowed molecular weight ratio of 1.9 to 2.07 and a dispersity of 1.2 to 1.65 from a starting PTMEG or copolymer with a broader molecular weight distribution having a dispersity of 1.9 to 2.3 and a molecular weight ratio of 2.3 to 2.6 is provided by feeding the PTMEG or copolymer and an effective amount of an inert solvent to a stripping apparatus and stripping at a temperature of 150 to 220 degrees C. and a pressure of 0.5 to 5 mm of mercury.
    Type: Grant
    Filed: October 17, 2000
    Date of Patent: March 12, 2002
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Suri Narayan Dorai, Richard Edward Ernst
  • Publication number: 20020019572
    Abstract: The present invention provides a method for alkoxylating organic compounds comprising contacting an organic compound adapted to be alkoxylated with an alkylene oxide in a reaction vessel under conditions effective to alkoxylate the organic compound. The alkylene oxide is maintained in vapor form during transport to said reaction vessel, during discharge into said reaction vessel, and during contacting of the organic compound with the alkylene oxide. The result is an alkoxylated product containing less flocculant.
    Type: Application
    Filed: April 19, 1999
    Publication date: February 14, 2002
    Inventor: PHILIP LEUNG
  • Publication number: 20020010374
    Abstract: The invention is a continuous process for the preparation of polytrimethylene ether glycol from 1,3-propanediol reactant. In addition, the invention is directed to a continuous multi-stage process comprising reacting at least one reactant in a liquid phase in an up-flow column reactor, and forming a gas or vapor phase by-product wherein the gas or vapor phase by-product is continuously removed at the top and at least one intermediate stage.
    Type: Application
    Filed: December 15, 2000
    Publication date: January 24, 2002
    Inventors: Hari B. Sunkara, Ernest Keith Andrew Marchildon, Howard Chung-Ho Ng, Leo E. Manzer
  • Publication number: 20010056212
    Abstract: A process for producing a monoalkyl ether which comprises a first step of contacting the following components (A) and (B):(A): an aqueous liquid phase containing: (a1) a C3-6 polyol having 3 or 4 hydroxyl groups, a palladium compound, a water-soluble tertiary phosphine or phosphite, and water; or (a2) a C3-6 polyol having 3 to 4 hydroxyl groups, a complex of palladium and a water-soluble tertiary phosphine or phosphite, and water, and (B): an oily liquid phase containing a conjugated diene, to give an alkadienyl ether containing an alkadienyl group resulting from dimerization of conjugated dienes; and a second step of hydrogenating the alkadienyl group in the alkadienyl ether in a hydrogen atmosphere in the presence of a catalyst containing an element selected from the Groups 8 to 10 elements of the periodic table.
    Type: Application
    Filed: May 31, 2001
    Publication date: December 27, 2001
    Applicant: KAO CORPORATION
    Inventors: Munehisa Okutsu, Tomohito Kitsuki, Atsushi Nagasawa
  • Patent number: 6291714
    Abstract: A continuous process for the production of polyadducts of alkylene oxide on a chain initiator with at least one active hydrogen comprises the step of: (a) providing n reaction units constituted by a tubular reactor (11), and a heat exchanger (14) downstream of the tubular reaction (11); (b) supplying the preheated chain initiator and the alkylene oxide to the reactor of the first reaction unit; (c) reacting the chain initiator with the alkylene oxide to obtain a first mixture; (d) cooling the first mixture by means of the heat exchanger (14); (e) supplying the reactor of the following reaction unit with the cooled mixture and with alkylene oxide; (f) repeating the procedure until the last reaction unit and then discharging the last mixture containing the desired product. The tubular reactors are vertical and the chain initiator and alkylene oxide are sprayed into the top of the reactor where a gas liquid reaction occurs.
    Type: Grant
    Filed: October 25, 1999
    Date of Patent: September 18, 2001
    Assignee: Linde Aktiengesellschaft
    Inventor: Pasquale Fanelli
  • Publication number: 20010007047
    Abstract: The present invention provides a process for producing a (poly)alkylene glycol monoalkyl ether with high selectivity and high yield. In this process, the (poly)alkylene glycol monoalkyl ether is produced by reacting an olefin and a (poly)alkylene glycol in the presence of a catalyst, wherein: 1) a crystalline metallosilicate is used as the catalyst, and at least a portion of the used catalyst is regenerated, and the regenerated catalyst is recycled as the catalyst for the reaction; or 2) the reaction between the olefin and the (poly)alkylene glycol is carried out in the presence of either or both of a (poly)alkylene glycol dialkyl ether and an alcohol.
    Type: Application
    Filed: February 21, 2001
    Publication date: July 5, 2001
    Applicant: Nippon Shokubai Co., Ltd.
    Inventors: Yoshiyuki Onda, Masaru Kirishiki, Hideaki Tsuneki, Yukio Kadono
  • Patent number: 6239315
    Abstract: A process for preparing glycol monoethers from olefins comprises reacting the olefins with an epoxidizing reagent in the simultaneous presence of hydroxyl-containing organic compounds over a mixture of epoxidation catalysts and alkoxylation catalysts.
    Type: Grant
    Filed: October 25, 1999
    Date of Patent: May 29, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Müller, Georg Heinrich Grosch, Andreas Walch, Norbert Rieber
  • Patent number: 6218580
    Abstract: The acid-catalyzed intermolecular etherification of mono- or polyhydric alcohols and acid-catalyzed ether cleavage in the presence of water may be improved if etherification or ether cleavage is carried out in the presence of an acid catalyst and, additionally, a hydrogenation catalyst under a hydrogen atmosphere. The process relates in particular to the etherification of diols, triols and tetrols with the formation of hydroxyethers.
    Type: Grant
    Filed: November 6, 1998
    Date of Patent: April 17, 2001
    Assignee: Degussa-Huls Aktiengesellschaft
    Inventors: Marcus Morawietz, Thomas Haas, Olaf Burkhardt, Rudolf Vanheertum
  • Patent number: 6124506
    Abstract: This invention relates to a process for making glycol ethers by reacting an olefin oxide with an alcohol over a catalyst comprising a layered double hydroxide (LDH) clay with its layered structure intact and having interlamellar anions at least some of which are metal anions or (poly)oxometallate anions. In the LDH clays, the interlamellar anions present are inorganic metal anions, oxometallate or polyoxometallate anions and include inter alia one or more of the following anions: chromium, vanadium, molybdenum and phosphorus, and (poly)oxoanions thereof. A copper-chromium hydrotalcite anionic clay or a magnesium-aluminium hydrotalcite anionic clay exchanged with (poly)oxometallate anions are preferred.
    Type: Grant
    Filed: December 18, 1997
    Date of Patent: September 26, 2000
    Assignee: BP Chemicals Limited
    Inventors: Martin Philip Atkins, Corinne Laurence Depege, Claude Rene Marcel Forano
  • Patent number: 6093855
    Abstract: The divinyl ethers of diethylene glycol or triethylene glycol are separated from the monovinyl ether of the corresponding oligoethylene glycol by distillation, a metal hydroxide being added to the vinyl ether mixture.
    Type: Grant
    Filed: September 23, 1998
    Date of Patent: July 25, 2000
    Assignee: BASF Aktiengesellschaft
    Inventor: Rudolf Erich Lorenz
  • Patent number: 5965778
    Abstract: Elastomers exhibiting decreased demold times and improved green strength are prepared by reacting a di- or polyisocyanate with a monodisperse polyoxypropylene diol having ultra-low unsaturation, and preferably prepared by the double metal cyanide.t-butyl alcohol catalyzed polymerization of propylene oxide. Further improved demold times and elevated elastomer physical properties are made possible by the use of multidisperse polyoxyalkylene polyether polyol blends having an overall unsaturation of less than 0.010 meq/g and a polydispersity of about 1.4 or greater.
    Type: Grant
    Filed: August 31, 1998
    Date of Patent: October 12, 1999
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Gary L. Allen, Nigel Barksby, Stephen D. Seneker, Usama E. Younes
  • Patent number: 5962748
    Abstract: Polyether polyols having reduced terminal unsaturation are prepared in a process comprising a first step comprising reacting propylene oxide with an initiator having at least two hydroxyl groups in the presence of a basic catalyst, a second step of contacting the polyether product of the first step having allyl terminal unsaturation with an isomerization catalyst whereby the allyl terminal unsaturation of the polyether is reduced by at least 90% conversion to propenyl terminal unsaturation in one step and, in a final step, the resulting polyether product of the first step is contacted with an acid catalyst whereby a substantial amount of the propenyl terminal unsaturation of the polyether is removed and the corresponding polyether having an additional hydroxyl group is obtained.
    Type: Grant
    Filed: October 23, 1997
    Date of Patent: October 5, 1999
    Assignee: Huntsman Petrochemical Corporation
    Inventor: Timothy L. Lambert
  • Patent number: 5962749
    Abstract: This invention relates to a process for the purification of polyether polyols. This process enables the removal of residual alkaline metal catalyst from produced polyether polyol. It comprises a) adding glycerine to a polyether polyol that contains Group IA alkaline metal catalyst to form a precipitate, and b) separating the precipitate formed in a) to provide a purified polyether polyol. The present invention also relates to the purified polyether polyol produced by this process, the precipitate produced by this process, and the use of the precipitate as an alkaline metal catalyst in a process for the production of polyether polyols.
    Type: Grant
    Filed: December 24, 1997
    Date of Patent: October 5, 1999
    Assignee: Bayer Corporation
    Inventors: Harold R. Parsons, Donald C. Dunham, Steven L. Schilling, Keith J. Headley
  • Patent number: 5945393
    Abstract: Novel nonionic gemini surfactants are extremely effective emulsifiers for oil-in-water emulsions that provide improved detergency at even low concentration levels. The surfactants are characterized by the formula: ##STR1## wherein R.sub.1 is independently H or a C.sub.1 to C.sub.22 alkyl, R.sub.2 is C.sub.6 to C.sub.22 alkyl and R.sub.3 is D.sub.1 --R.sub.4 --D.sub.1 or R.sub.4 --D.sub.1 --R.sub.4 wherein R.sub.4 is independently a C.sub.1 -C.sub.10 alkyl group, --O--R.sub.5 --O--, or aryl, e.g. phenyl, and D.sub.1 is independently --O--, an amide group ?--C(O)N(R.sub.6)--!, an amino group ?--N(R.sub.6)--!, --O--R.sub.5 --O--, or aryl. (EO).sub.a (PO).sub.b is a polyether group and Z is a C.sub.1 -C.sub.4 alkyl, or an alkylaryl or hydrogen wherein EO represents ethyleneoxy radicals, PO represents propyleneoxy radicals, a and b are numbers of from 0 to 100, a is preferably from about 0 to about 30 and b is preferably from about 0 to 10, wherein a plus b is at least one, and the EO and PO alkyl or alkylaryl.
    Type: Grant
    Filed: November 7, 1997
    Date of Patent: August 31, 1999
    Assignee: Rhodia Inc.
    Inventors: David James Tracy, Ruoxin Li, Manilal S. Dahanayake, Jiang Yang
  • Patent number: 5914430
    Abstract: Ether compounds, which are useful as solvents, cosmetics, detergents, lubricants, emulsifiers and so on, are produced by reacting (a) a hydroxy compound with a carbonyl compound of (b) a carbonyl compound under hydrogen atmosphere in the presence of a catalyst with ease and at a low cost. The reaction is carried out while removing out produced water by using a dehydrating agent during the reaction; by distilling off the water by azeotropic dehydration and the like; or by blowing gases such as hydrogen gas to flow through the reaction system.
    Type: Grant
    Filed: July 5, 1996
    Date of Patent: June 22, 1999
    Assignee: Kao Corporation
    Inventors: Yasuyuki Fujii, Hisakazu Furugaki, Katsumi Kita, Mitsuru Uno, Eiko Tamura, Hiromasa Matsumoto
  • Patent number: 5877245
    Abstract: The reaction product ofA) a linking compound of formula IR.sup.1 (X).sub.3 (I)wherein each X group is a halogen or one X group is a halogen and two X groups with 2 carbon atoms from the R.sup.1 group and an oxygen atom form an epoxy group, and R.sup.1 is an alkanetriyl group containing from 3 to 10 carbon atoms;B) a compound of formula IIR.sup.2 (OA).sub.n --OH (II)wherein R.sup.2 is an aliphatic group containing from 4 to 36 carbon atoms, n is a number of from 1 to 200, and each OA group is independently an ethyleneoxy, 1,2-propyleneoxy, or 1,2-butyleneoxy group; andC) a compound of formula IIIH--(OA).sub.m --OH (III)wherein OA is as defined above, and m is a number of from 1 to 500;processes for its preparation; and methods for its use as a thickener in aqueous compositions.
    Type: Grant
    Filed: August 15, 1997
    Date of Patent: March 2, 1999
    Assignee: Henkel Corporation
    Inventors: Michael S. Wiggins, David I. Devore
  • Patent number: 5847229
    Abstract: Process for the production of end-capped nonionic surfactants by forming an alcoholate between a fatty alcohol polyglycol ether and a solid base, reacting the alcoholate with a dialkyl sulfate, adding water to initiate phase separation, and separating the organic layer from the aqueous layer.
    Type: Grant
    Filed: June 9, 1997
    Date of Patent: December 8, 1998
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Joaquim Bigorra Llosas, Nuria Bonastre, Antonio Trius Oliva, Rafael Pi Subirana
  • Patent number: 5811594
    Abstract: Methyl-end-capped alkyl and/or alkenyl polyglycol ethers; a process for their production by methylation of products of the addition of ethylene oxide and propylene oxide to primary alcohols; to formulations containing these substances; and to the use of the substances for the production of surface-active formulations.
    Type: Grant
    Filed: March 7, 1997
    Date of Patent: September 22, 1998
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Karl Schmid, Joaquim Bigorra Llosas
  • Patent number: 5777175
    Abstract: Propylene oxide is added to an active hydrogen compound in the presence of an alkali metal hydroxide catalyst in an amount of from 0.05 to 0.5 mole per mole of the active hydrogen compound at a reaction temperature of from 60.degree. to 98.degree. C. at a reaction pressure less than or equal to 4 kg/cm.sup.2 to prepare a polyoxyalkylene polyol which has a hydroxyl value of from 10 to 35 mg KOH/g, a monool content less than or equal to 15 mol %, a Head-to-Tail bond selectivity greater than or equal to 96 percent, and low viscosity. A polymer polyol is prepared by polymerizing an ethylenically unsaturated monomer in the polyoxyalkylene polyol. A flexible polyurethane foam is prepared by reacting the polyoxyalkylene polyol or the polymer polyol with an organic polyisocyanate compound in the presence of a foaming agent, a catalyst, a surfactant, a crosslinking agent and other additives.
    Type: Grant
    Filed: April 12, 1995
    Date of Patent: July 7, 1998
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Kazuhiko Ohkubo, Tomoki Tsutsui, Yoshitsugu Sakaki, Tamotsu Kunihiro, Ariko Nishikawa, Tsukuru Izukawa, Kaoru Ueno, Seijiro Sakai, Yukichi Tanaka
  • Patent number: 5773525
    Abstract: Oligomeric polyoxyalkylene polyethers are prepared by oxyalkylating a low molecular weight hydroxyl-functional starter molecule with one or more alkylene oxides in the presence of a solid, heterogeneous magnesium oxide catalyst. The catalyst is readily and rapidly removed by simple filtration to yield a polyether with minimal metal ion content suitable for use directly or as a starter molecule for further double metal cyanide complex catalyzed oxyalkylation.
    Type: Grant
    Filed: June 20, 1997
    Date of Patent: June 30, 1998
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Jose F. Pazos
  • Patent number: 5750796
    Abstract: A method of producing alkylene oxide adduct comprises reacting an organic compound having one or more active hydrogen (for example, higher alcohol, amine, etc.) with alkylene oxide in the presence of an Al.Mg composite oxide catalyst. The catalyst can be obtained by calcining and activating aluminum magnesium hydroxide shown by nMgO.Al.sub.2 O.sub.3.mH.sub.2 O. In this method, a highly active reaction can be performed, and alkylene oxide adduct having very narrow alkylene oxide adduct molar distribution can be obtained. Since the load in a catalyst separating step is reduced, the catalyst can be efficiently separated. Therefore, the alkylene oxide adduct can be produced at low cost. In addition, the reaction can be performed at high speed, and the reaction time can be reduced.
    Type: Grant
    Filed: August 23, 1996
    Date of Patent: May 12, 1998
    Assignee: Lion Corporation
    Inventors: Itsuo Hama, Takahiro Okamoto, Hisashi Sasamoto, Hirofumi Nakamura
  • Patent number: 5741948
    Abstract: There is provided a process for producing a (poly)alkylene glycol monoalkyl ether from an olefin and a (poly)alkylene glycol at a high conversion at a high selectivity. This process comprises reacting an olefin with a (poly)alkylene glycol in the presence of a crystalline metallosilicate as a catalyst.
    Type: Grant
    Filed: June 6, 1996
    Date of Patent: April 21, 1998
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Masaru Kirishiki, Yukio Kadono, Isamu Maeda, Yasuhiko Satoh, Fumiaki Morishita, Yoshiyuki Onda, Hideaki Tsuneki
  • Patent number: 5731476
    Abstract: Polyethers of polyhydric compounds are prepared by the liquid phase reaction of polyhydric compound and the reaction being carried out with separate liquid phases comprised of a polar polyhydric compound phase and an organic polyether containing phase.
    Type: Grant
    Filed: December 1, 1995
    Date of Patent: March 24, 1998
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Edward T. Shawl, Haven S. Kesling, Jr., Vijai P. Gupta
  • Patent number: 5728796
    Abstract: A process reaction between: (1) a compound that contains one or more epoxide moieties per molecule, and (2) a compound that contains one or more primary aliphatic hydroxyl groups per molecule; is catalyzed by: (3) a catalyst compound containing one or more trifluoromethanesulfonate moieties and one or more silyl moieties and run at a temperature of no more than 130.degree. C., such that the catalyst preferably catalyzes reaction at the primary aliphatic hydroxyl group, so that the resulting resin does not gel.
    Type: Grant
    Filed: May 31, 1996
    Date of Patent: March 17, 1998
    Assignee: The Dow Chemical Company
    Inventors: Zeng K. Liao, James L. Bertram
  • Patent number: 5721305
    Abstract: Glycerol, 2,2-dimethyl-1,3-dioxolane-4-methanol (Solketal), glycidol or glycerol carbonate is polymerized into preponderantly linear oligomers at 150.degree. C. to 350.degree. C. in the presence of anionic clay material, preferably hydrotalcite, as a catalyst.
    Type: Grant
    Filed: June 12, 1996
    Date of Patent: February 24, 1998
    Assignee: Unichema Chemie B.V.
    Inventors: Johan Jan W. Eshuis, Johannes Arie M. Laan, Glyn Roberts
  • Patent number: 5698746
    Abstract: Polyether polyols having reduced terminal unsaturation are prepared in a process comprising a first step of contacting a polyether having allyl terminal unsaturation with an isomerization catalyst whereby the allyl terminal unsaturation of the polyether is reduced by at least 90% conversion to propenyl terminal unsaturation in one step and, in a final step, the resulting polyether product of the first step is contacted with an acid catalyst whereby a substantial amount of the propenyl terminal unsaturation of the polyether is removed and the corresponding polyether having an additional hydroxyl group is obtained.
    Type: Grant
    Filed: November 4, 1996
    Date of Patent: December 16, 1997
    Assignee: Huntsman Petrochemical Corporation
    Inventor: Timothy L. Lambert
  • Patent number: 5693870
    Abstract: Disclosed is an apparatus and process for producing a tripropylene glycol in which alkylene oxide, water, an acid catalyst and a dipropylene glycol are contacted together under conditions suitable to form the tripropylene glycol. Water is present in the reaction mixture in the range of about 1 to about 50 weight percent of the reaction mixture. The ratio of water to alkylene oxide is less than about 9. The tripropylene glycol thus produced exhibits a higher primary hydroxyl group content generally exceeding 36 percent. Such tripropylene glycols find utility in the production of acrylics. Also disclosed is a process for making esters from such glycols.
    Type: Grant
    Filed: May 3, 1995
    Date of Patent: December 2, 1997
    Assignee: The Dow Chemical Company
    Inventors: Jeffrey David Birdwell, Philip Jay Carlberg, Micheal L. Chappell, Frank Harold Murphy, Robert Page Shirtum, Walter L. Wernli
  • Patent number: 5689012
    Abstract: A continuous process for the preparation of polyoxyalkylene polyethers using DMC catalysts as the polyoxyalkylation catalyst employs continuous addition of alkylene oxide in conjunction with continuous addition of starter and catalyst to a continuous oxyalkylation reactor. Despite the continuous introduction of starter, the molecular weight distribution of the polyether product is quite narrow, as indicated by the exceptionally low polydispersity of the product. The presence of low molecular weight species during the majority of the polyoxyalkylation also substantially eliminates extremely high molecular weight fractions having molecular weights greater than 100,000 Da, again without appreciably broadening molecular weight distribution. By withdrawing intermediate molecular weight polyether product or diverting a portion of the end product to prepare a catalyst/starter mixture, rapid and sustained reaction rates can be achieved while employing low molecular weight starters.
    Type: Grant
    Filed: July 18, 1996
    Date of Patent: November 18, 1997
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Jose F. Pazos, T. Thomas Shih
  • Patent number: 5679764
    Abstract: Oligomeric polyoxyalkylene polyethers are prepared by oxyalkylating a low molecular weight hydroxyl-functional starter molecule with one or more alkylene oxides in the presence of a solid, heterogeneous magnesium oxide catalyst. The catalyst is readily and rapidly removed by simple filtration to yield a polyether with minimal metal ion content suitable for use directly or as a starter molecule for further double metal cyanide complex catalyzed oxyalkylation.
    Type: Grant
    Filed: November 6, 1995
    Date of Patent: October 21, 1997
    Assignee: ARCO Chemical Technology, L.P.
    Inventor: Jose F. Pazos
  • Patent number: 5659089
    Abstract: A process for making poly(2-methyl-1,3-propanediol) is disclosed. The process comprises heating 2-methyl-1,3-propanediol in the presence of an etherification catalyst at a temperature within the range of about 100.degree. C. to about 210.degree. C. The resulting poly(2-methyl-1,3-propanediol) has a degree of polymerization within the range of about 2 to about 20, and a number average molecular weight within the range of about 150 to about 2000. The process enables the synthesis of dimers and trimers of 2-methyl-1,3-propanediol, which are useful as reactive diluents or chain extenders for polyurethanes and as diol components for unsaturated polyester resins and thermoplastic polyesters.
    Type: Grant
    Filed: May 22, 1996
    Date of Patent: August 19, 1997
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Gangfeng Cai, Robert G. Gastinger, Carl J. Sullivan
  • Patent number: 5648559
    Abstract: High resilience polyurethane foams exhibiting little or no shrinkage may be prepared from low unsaturation double metal cyanide catalyzed polyoxyalkylene polyols in amounts greater than 20 weight percent of the total polyol component, when low unsaturation poly(oxypropylene/oxyethylene) random polyols having less than 35 weight percent of an all polyoxypropylene block catalyzed by double metal cyanide catalysts and one or more external random polyoxypropylene/polyoxyethylene blocks each containing 2 weight percent or more oxyethylene moieties, and an unsaturation of less than 0.02 meq/g are employed.
    Type: Grant
    Filed: October 21, 1996
    Date of Patent: July 15, 1997
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Stanley L. Hager