From Alkylene Oxide Patents (Class 568/867)
  • Patent number: 6362276
    Abstract: A heterobifunctional poly(ethylene glycol) is provided having a hydrolytically degradable linkage, a first terminus comprising an acrylate group, and a second terminus comprising a target such as a protein or pharmaceutical agent or a reactive moiety capable of coupling to a target. Hydrogels can be prepared. The hydrogels can be used as a carrier for a protein or a pharmaceutical agent that can be readily released in a controlled fashion.
    Type: Grant
    Filed: January 6, 1999
    Date of Patent: March 26, 2002
    Assignee: Debio Recherche Pharmaceutique S.A.
    Inventors: J. Milton Harris, Xuan Zhao
  • Patent number: 6348632
    Abstract: A process for preparing an 1,3-alkanediol through carbonylation of an epoxide derivative includes the steps of (a) reacting an epoxide derivative with alcohol and carbon monoxide in a solvent at a temperature from about 30 to about 150° C. and at a pressure from about 50 to about 3000 psig in the presence of a catalyst system including an effective amount of a cobalt catalyst and an effective amount of a promoter to afford a reaction mixture including a 3-hydroxyester or derivative thereof in an amount of from 2 to about 95% by weight, (b) separating the reaction product and solvent from the catalyst and promoter, (c) reacting said reaction product and solvent with hydrogen at a temperature from about 30 to about 350° C. and at a pressure from about 50 to about 5000 psig in the presence of a catalyst system for hydrogenation to prepare a hydrogenation product mixture including a 1,3-alkanediol, and (d) recovering the 1,3-alkanediol from the hydrogenation product mixture.
    Type: Grant
    Filed: May 12, 2000
    Date of Patent: February 19, 2002
    Assignee: Samsung Electronics Co. Ltd.
    Inventors: Byeong-No Lee, Byung-Soon Chen
  • Publication number: 20020010378
    Abstract: In a composite process for subjecting ethylene to catalytic gas phase oxidation thereby obtaining ethylene oxide and causing this ethylene oxide to react with water thereby obtaining ethylene glycol, a method for producing the ethylene glycol is provided which permits effective utilization of the energy at the step for dehydrating and concentrating the resultant aqueous ethylene glycol solution. In the production of ethylene glycol by the supply of the aqueous ethylene glycol solution to a concentrating treatment at the multi-effect evaporator, the method contemplated by this invention for the production of ethylene glycol comprises utilizing as the source of heating at least one specific step the steam generated in the multi-effect evaporator.
    Type: Application
    Filed: April 27, 2001
    Publication date: January 24, 2002
    Inventors: Yukihiko Kakimoto, Yoshihisa Oka
  • Patent number: 6329558
    Abstract: In a process for isolating alkylene glycol having a low aldehyde content, in which a mixture comprising alkylene glycol is subjected to a final distillation, formic acid or a formate or a mixture of two or more formates or a mixture of formic acid and one or more formates is present in the mixture comprising alkylene glycol.
    Type: Grant
    Filed: June 23, 2000
    Date of Patent: December 11, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Jürgen Mohr, Toni Dockner
  • Patent number: 6323374
    Abstract: Ethylene oxide is hydroformylated to 3-hydroxypropanal using a non-phosphine-ligated cobalt catalyst and an amide promoter.
    Type: Grant
    Filed: June 15, 2001
    Date of Patent: November 27, 2001
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Yuan-Zhang Han
  • Patent number: 6316571
    Abstract: The present invention relates to a process for the preparation of alkylene glycols by reacting an alkylene oxide with water in the presence of a catalytic composition including a polycarboxylic acid derivative, having in its chain molecule one or more carboxyl groups and one or more carboxylate groups, the individual carboxyl and/or carboxylate groups being separated from each other in the chain molecule by a separating group consisting of at least one atom. Preferably the polycarboxylic acid derivative is immobilised on a solid support.
    Type: Grant
    Filed: August 24, 2000
    Date of Patent: November 13, 2001
    Assignee: Shell Oil Company
    Inventor: Eugene Marie Godfried Andre Van Kruchten
  • Publication number: 20010016624
    Abstract: A heterobifunctional poly(ethylene glycol) is provided having a hydrolytically degradable linkage, a first terminus comprising an acrylate group, and a second terminus comprising a target such as a protein or pharmaceutical agent or a reactive moiety capable of coupling to a target. Hydrogels can be prepared. The hydrogels can be used as a carrier for a protein or a pharmaceutical agent that can be readily released in a controlled fashion.
    Type: Application
    Filed: April 2, 2001
    Publication date: August 23, 2001
    Applicant: Debio Recherche Pharmaceutique S.A.
    Inventors: J. Milton Harris, Xuan Zhao
  • Publication number: 20010011147
    Abstract: Method for obtaining components of a packet of additives for engine fuels by oxyalkylenation of organic compounds containing hydroxyl groups by means of alkylene oxide at the presence of basic catalysts, at the temperature 80-170° C., characteristic in that the mixture containing 94.5-99.9% by mass of alkyl phenols of the general formula according to FIG. 1, where R1-alkyl group of the carbon atoms number from 6 to 16 and not more than 0.1% by mass of water (H2O) and not more than 5.0% by mass (preferably from 0.1 to 1.0 by mass) of monohydroxyl alcohols of the general formula R2—OH, where R2-alkyl group of the carbon atoms number from 1 to 4, is oxyalkylenated with ethylene oxide or propylene oxide up to the moment of obtaining the molecular mass of oxyalkylenated alcohol not lower than 100 daltons and the hydroxyl number not higher than 150 mg of KOH/g, and next the product of synthesis is contacted at the temperature not higher than 150° C.
    Type: Application
    Filed: January 12, 2001
    Publication date: August 2, 2001
    Inventors: Andrzej Krueger, Boguslaw Tkacz, Winicjusz Stanik, Leszek Ziemianski, Kazimierz Chlobowski, Kazimierz Szymanski, Ryszard Kosciuk, Wladyslaw Millan, Anna Rzodeczko, Jan Poskrobko, Wojciech Balcerowiak, Jerzy Jasienkiewicz
  • Patent number: 6265625
    Abstract: This invention relates to a process for preparing and isolating glycols and to a thin-film evaporator which is used in carrying out the process.
    Type: Grant
    Filed: December 1, 1999
    Date of Patent: July 24, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Frans Vansant, Jozef de Hert, Dieter Köffer, Gerhard Theis, Winfried Terjung
  • Patent number: 6242655
    Abstract: High purity ethylene glycol containing 2000 ppm or less aldehyde is contacted with a solid strong acid cation exchange resin and an ethylene glycol product reduced in aldehydes content is recovered.
    Type: Grant
    Filed: July 11, 2000
    Date of Patent: June 5, 2001
    Assignee: Scientific Design Company, Inc.
    Inventor: Mansoor Husain
  • Patent number: 6211419
    Abstract: A method for operating an epoxide containing system which contains a catalyst is disclosed. The method comprises feeding carbon dioxide to the epoxide containing system at an amount of from 0.01 to 5.0 weight percent; and maintaining the epoxide containing system at a temperature of from 100° C. to 150° C. The catalyst has a half life of at least 40 days at 120° C. The present invention allows anion exchange resins in the bicarbonate form to be used for the hydrolysis of ethylene oxide at temperatures exceeding 100° C. The rate of catalyst swelling is minimized and lifetime of the catalyst enhanced.
    Type: Grant
    Filed: April 24, 2000
    Date of Patent: April 3, 2001
    Assignee: The Dow Chemical Company
    Inventors: Gary R. Strickler, Von G. Landon, Guo-Shuh John Lee
  • Patent number: 6160187
    Abstract: A method for making glycol in an adiabatic reactor system including feeding water and an epoxide into at least one adiabatic reactor under conditions such that epoxide and the water react to form a glycol product stream. The adiabatic reactor contains a catalyst bed which undergoes swelling during its useful lifetime, and the adiabatic reactor operates under conditions sufficient to reduce the rate of catalyst swelling relative to a non-adiabatic reactor system. Other aspects of the invention include the combination of splitting the feed between multiple adiabatic reactors in combination with the cross exchange of heat between feeds and products with heat exchangers, such that an energy efficient process that provides long catalyst stability and minimal catalyst swelling results.
    Type: Grant
    Filed: December 8, 1998
    Date of Patent: December 12, 2000
    Assignee: The Dow Chemical Company
    Inventors: Gary R. Strickler, Von G. Landon, Guo-shuh John Lee, William J. Rievert
  • Patent number: 6156942
    Abstract: A process for the preparation of an alkylene glycol by reacting an alkylene oxide with water in the presence of a solid catalytic composition which includes a strongly basic ion exchange resin coordinated with one or more anions, and a stabilising additive which is an acidic ion exchange resin. Preferably the acidic ion exchange resin is of the weakly acidic methacrylate type.
    Type: Grant
    Filed: December 14, 1998
    Date of Patent: December 5, 2000
    Assignee: Shell Oil Company
    Inventors: Michael Francis Lemanski, Eugene Marie Godfried Andre Van Kruchten, Robert Kunin
  • Patent number: 6153801
    Abstract: The present invention relates to a process for the preparation of alkylene glycols by reacting an alkylene oxide with water in the presence of a catalytic composition including a polycarboxylic acid derivative, having in its chain molecule one or more carboxyl groups and one or more carboxylate groups, the individual carboxyl and/or carboxylate groups being separated from each other in the chain molecule by a separating group consisting of at least one atom. Preferably the polycarboxylic acid derivative is immobilised on a solid support.
    Type: Grant
    Filed: December 9, 1999
    Date of Patent: November 28, 2000
    Assignee: Shell Oil Company
    Inventor: Eugene Marie Godfried Andre Van Kruchten
  • Patent number: 6147265
    Abstract: A process for producing an alkylene glycol which comprises a step of reacting an alkylene oxide with water in the presence of a catalyst, wherein the catalyst comprises an anion-exchange resin comprising: a polymer of a vinylaromatic compound as a substrate; and quaternary ammoniums group each bonded to the respective aromatic groups of the polymer substrate via a connecting group having a chain length of three or more atoms.
    Type: Grant
    Filed: April 27, 1998
    Date of Patent: November 14, 2000
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Tomoatsu Iwakura, Hidekazu Miyagi
  • Patent number: 6137015
    Abstract: A process for preparing alkylene glycols including reacting an alkylene oxide with water in the presence of a combination of additives and an anion exchange resin, wherein the combination of additives comprises carbon dioxide and an organic or inorganic base provided in an amount sufficient to maintain a pH of the reaction mixture between about 5.0 and 9.0, with the proviso that, when the base is bicarbonate or carbonate, then the anion exchange resin is a trimethyl benzyl ammonium anion exchange resin. A particularly preferred method of this invention is to react ethylene oxide with water in the presence of a halogenate or bicarbonate-type anionic exchange resin (such as a DOWEX.TM. MSA-1 type resin), carbon dioxide, and sodium hydroxide. Some advantages of this invention are that it provides desirable catalyst lifetime and activity, minimizes resin swelling, and provides a desirable, sustained selectivity to alkylene glycol.
    Type: Grant
    Filed: December 8, 1998
    Date of Patent: October 24, 2000
    Assignee: The Dow Chemical Company
    Inventors: Gary R. Strickler, Von G. Landon, Guo-shuh John Lee, William J. Rievert
  • Patent number: 6137014
    Abstract: A process for the preparation of alkylene glycols by reacting an alkylene oxide with water in the presence of a catalytic composition comprising a macrocyclic chelating compound complexed with an ionic compound the anion of which is catalytically effective under the reaction conditions. Preferably, the macrocycle is a crown ether or a cryptate and the anion is selected from the group of halogenides, carboxylates having from 1-20 carbon atoms, hydrogen carbonate, hydrogen sulphite, hydrogen phosphate and metalates.
    Type: Grant
    Filed: October 30, 1998
    Date of Patent: October 24, 2000
    Assignee: Shell Oil Company
    Inventor: Eugene Marie Godfried Andre Van Kruchten
  • Patent number: 6124508
    Abstract: A process for the preparation of alkylene glycols by reacting an alkylene oxide with water in the presence of at least one ionic composition of a quaternary phosphonium cation of the general formulaR.sub.1 R.sub.2 R.sub.3 R.sub.4 P.sup.+Whereby each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4, independently, may be an alkyl, cycloalkyl, aryl, alkylaryl or arylalkyl group having from 1 to 10 carbon atoms, each of which may carry one or more substituents, or be attached to a polymer and an anion other than metalate or halogen.
    Type: Grant
    Filed: December 9, 1999
    Date of Patent: September 26, 2000
    Assignee: Shell Oil Company
    Inventor: Eugene Marie Godfried Andre Van Kruchten
  • Patent number: 6103941
    Abstract: 1,4-Butanediol is prepared by a process which comprises converting 1,3-butadiene diepoxide in the presence of hydrogen over a hydrogenation catalyst whose active component is not elemental Pd and/or Pt. The hydrogenation catalyst preferably contains at least one element from the group Ib, VIIb or VIIIb of the Periodic Table of Elements.
    Type: Grant
    Filed: September 6, 1995
    Date of Patent: August 15, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Christoph Sigwart
  • Patent number: 5945570
    Abstract: A solid, particulate catalyst composition is provided containing an active nickel component in which the nickel constitutes from about 25 to about 60 wt % of the catalyst composition; a molybdenum component in which the molybdenum constitutes from about 5 to about 20 wt % of the catalyst composition; and a binder component comprising at least one of oxides of silica, zirconium, aluminum, zinc and calcium, each of the calcium, aluminum and zinc being present in an amount no greater than about 2 wt %, preferably about 0 to 1 wt %. The catalyst is designed for the selective hydrogenation of 3-hydroxypropanal to 1,3-propanediol in aqueous solution.
    Type: Grant
    Filed: October 29, 1998
    Date of Patent: August 31, 1999
    Inventors: Juan Pedro Arhancet, Paul Himelfarb, Joseph Broun Powell, Robert Alfred Plundo, Mohammed Shahjahan Kazi, William Joseph Carrick
  • Patent number: 5874653
    Abstract: A process is disclosed for preparing an alkylene glycol by reacting an alkylene oxide with water in the presence of a catalyst comprising a polymeric organosiloxane ammonium salt having a silica-like skeleton and comprising units of the general formula (I) ##STR1## wherein R.sup.1 to R.sup.4, Y and x are as specified in claim 1. Preferred are the catalysts wherein the anion Y is selected from the group of carboxylates having from 1-20 carbon atoms, hydrogen carbonate, hydrogen sulphite, hydrogen phosphate and metalate. These catalysts exhibit an enhanced selectivity stability.
    Type: Grant
    Filed: November 25, 1996
    Date of Patent: February 23, 1999
    Assignee: Shell Oil Company
    Inventor: Eugene Marie Godfried Andre Van Kruchten
  • Patent number: 5844070
    Abstract: A process for activating double metal cyanide catalysts is disclosed. A polyol starter or starter/catalyst mixture is heated under vacuum under conditions effective to achieve improved stripping compared with that which can be achieved through conventional vacuum stripping. Coupling vacuum stripping with inert gas sparging or stripping in the presence of an organic solvent gives a starter/catalyst mixture that activates rapidly in an epoxide polymerization process. Rapid activation makes process start-ups reliable and reduces cycle time. The process gives polyols with lower viscosity, lower polydispersity, and lower unsaturation for better polyurethanes.
    Type: Grant
    Filed: May 16, 1997
    Date of Patent: December 1, 1998
    Assignee: Arco Chemical Technology, L.P.
    Inventors: John E. Hayes, Leah J. Langsdorf, Bruce H. Isaacs, Fred J. Armellini
  • Patent number: 5841003
    Abstract: An alkanediol such as 1,3-propanediol is prepared in a process which involves reacting an alkylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of a non-phosphine-ligated cobalt catalyst and a lipophilic ruthenium promoter to produce an intermediate product mixture containing a hydroxyalkanal in an amount less than 15 wt %; extracting the hydroxyalkanal from the intermediate product mixture into an aqueous liquid at a temperature less than about 100.degree. C. and separating the aqueous phase containing hydroxyalkanal from the organic phase containing cobalt catalyst; hydrogenating the hydroxyalkanal in the aqueous phase to an alkanediol; and recovering the alkanediol.The process enables the production of an alkanediol such as 1,3-propanediol in high yields and selectivity without the use of a phosphine ligand-modified cobalt catalyst.
    Type: Grant
    Filed: July 23, 1996
    Date of Patent: November 24, 1998
    Assignee: Shell Oil Company
    Inventors: Lynn Henry Slaugh, Paul Richard Weider, Joseph Broun Powell
  • Patent number: 5763691
    Abstract: The present invention relates to a process for producing ethylene glycol from ethylene oxide wherein ethylene oxide in a gas resulting from oxidation of ethylene is absorbed in a specific absorbing solution, is allowed to react with carbon dioxide, converted into ethylene carbonate, and then subjected to hydrolysis to produce ethylene glycol.According to the present invention, a large energy consuming step such as stripping of ethylene oxide and separation of excess amounts of water during the ethylene glycol production becomes unnecessary and the process can be greatly simplified by combining the ethylene oxide absorption step and the carbonation step.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: June 9, 1998
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Kazuki Kawabe, Kazuhiko Murata, deceased, Toshiyuki Furuya
  • Patent number: 5731478
    Abstract: An alkanediol such as 1,3-propanediol is prepared in a process which involves reacting an alkylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of a non-phosphine-ligated cobalt or rhodium catalyst and a manganese porphyrine promoter to produce an intermediate product mixture containing a hydroxyalkanal in an amount less than 15 wt %; extracting the hydroxyalkanal from the intermediate product mixture into an aqueous liquid at a temperature less than about 100.degree. C. and separating the aqueous phase containing hydroxyalkanal from the organic phase containing cobalt catalyst; hydrogenating the hydroxyalkanal in the aqueous phase to an alkanediol; and recovering the alkanediol.The process enables the production of an alkanediol such as 1,3-propanediol in high yields and selectivity without the use of a phosphine ligand with the cobalt or rhodium catalyst.
    Type: Grant
    Filed: October 15, 1996
    Date of Patent: March 24, 1998
    Assignee: Shell Oil Company
    Inventors: Lynn Henry Slaugh, Paul Richard Weider, Joseph Broun Powell, Juan Pedro Arhancet
  • 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: 5723389
    Abstract: An alkanediol such as 1,3-propanediol is prepared in a process which involves reacting an alkylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of a non-phosphine-ligated cobalt or rhodium catalyst and a cobalt or rhodium porphyrin promoter to produce an intermediate product mixture containing a hydroxyalkanal in an amount less than 15 wt %; extracting the hydroxyalkanal from the intermediate product mixture into an aqueous liquid at a temperature less than about 100.degree. C. and separating the aqueous phase containing hydroxyalkanal from the organic phase containing cobalt catalyst; hydrogenating the hydroxyalkanal in the aqueous phase to an alkanediol; and recovering the alkanediol.The process enables the production of an alkanediol such as 1,3-propanediol in high yields and selectivity without the use of a phosphine ligand with the cobalt or rhodium catalyst.
    Type: Grant
    Filed: October 15, 1996
    Date of Patent: March 3, 1998
    Assignee: Shell Oil Company
    Inventors: Lynn Henry Slaugh, Paul Richard Weider, Joseph Broun Powell, Juan Pedro Arhancet
  • Patent number: 5561217
    Abstract: A process for the preparation of polyoxyalkylene glycols or polyoxyalkylene glycol copolymers from polyoxyalkylene glycol formates or the formates of polyoxyalkylene glycol copolymers comprises reacting the formates of polyoxyalkylene glycols or of polyoxyalkylene glycol copolymers in the liquid phase in the presence of a heterogeneous catalyst which contains, as catalytically active component, rhenium and/or at least one element from sub-group VIII of the Periodic Table of the Elements.
    Type: Grant
    Filed: April 24, 1995
    Date of Patent: October 1, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Juergen Weyer, Rolf Fischer, Rolf Pinkos
  • Patent number: 5545767
    Abstract: 1,3-propanediol is prepared in a process comprising the steps of:contacting ethylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of an effective amount of a non-phosphine-ligated cobalt catalyst and an effective amount of a lipophilic phenol at a temperature within the range of about 50.degree. to about 100.degree. C. and a pressure within the range of about 500 to about 5000 psig, under reaction conditions effective to produce an intermediate product mixture comprising less than about 15 wt % 3-hydroxypropanal;adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid at a temperature less than about 100.degree. C.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: August 13, 1996
    Assignee: Shell Oil Company
    Inventors: Paul R. Weider, Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Thomas C. Semple
  • Patent number: 5545712
    Abstract: An alkali metal compound such as metallic cesium, cesium hydroxide, cesium hydroxide monohydrate, metallic rubidium, rubidium hydroxide or rubidium hydroxide monohydrate is used as a catalyst, crude polyoxyalkylene polyol containing the catalyst is neutralized with a mineral acid or an organic acid, an aqueous solution layer containing an alkali metal salt is brought into contact with an anion exchange resin to adsorb mineral acid anion or organic acid anion, the alkali metal compound catalyst is recovered, alkylene oxide undergoes ring-opening addition polymerization on an active hydrogen compound in the presence of the recovered alkali metal compound catalyst to prepare polyoxyalkylene polyol, the catalyst is thereafter separated, recovered and reused, and such recycle of the alkali metal compound catalyst provides an economical process.
    Type: Grant
    Filed: August 23, 1995
    Date of Patent: August 13, 1996
    Assignee: Mitsu Toatsu Chemicals, Inc.
    Inventors: Tomoki Tsutsui, Tsukuru Izukawa, Kazuhiko Ohkubo, Yoshitsugu Sakaki
  • Patent number: 5493035
    Abstract: Activated carbon to be used in the removal of impurities from propylene oxide is first pre-wetted with a glycol such as propylene glycol; after bed deactivation, water containing a basic catalyst is added to hydrolyze propylene oxide and to form a non-hazardous slurry of carbon, propylene glycol and water.
    Type: Grant
    Filed: March 24, 1995
    Date of Patent: February 20, 1996
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Ahmad Soltani-Ahmadi, Thomas C. Mullin
  • Patent number: 5488184
    Abstract: A process for the preparation of alkylene glycols comprising reacting an alkylene oxide with water in the presence of a catalyst composition comprising a solid material having one or more electropositive sites, which are coordinated with one or more anions other than metalate or halogen anions, with the proviso that when the solid material is an anionic exchange resin of the quaternary ammonium type and the anion is bicarbonate, the process is performed in the substantial absence of carbon dioxide.
    Type: Grant
    Filed: January 31, 1995
    Date of Patent: January 30, 1996
    Assignee: Shell Oil Company
    Inventors: Willem G. Reman, Eugene M. G. A. Van Kruchten
  • Patent number: 5468840
    Abstract: An alkali metal compound such as metallic cesium, cesium hydroxide, cesium hydroxide monohydrate, metallic rubidium, rubidium hydroxide or rubidium hydroxide monohydrate is used as a catalyst, crude polyoxyalkylene polyol containing the catalyst is neutralized with a mineral acid or an organic acid, an aqueous solution layer containing an alkali metal salt is brought into contact with an anion exchange resin to adsorb mineral acid anion or organic acid anion, the alkali metal compound catalyst is recovered. alkylene oxide undergoes ring-opening addition polymerization on an active hydrogen compound in the presence of the recovered alkali metal compound catalyst to prepare polyoxyalkylene polyol, the catalyst is thereafter separated, recovered and reused, and such recycle of the alkali metal compound catalyst provides an economical process.
    Type: Grant
    Filed: August 29, 1994
    Date of Patent: November 21, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Tomoki Tsutsui, Tsukuru Izukawa, Kazuhiko Ohkubo, Yoshitsugu Sakaki
  • Patent number: 5463145
    Abstract: 1,3-Propanediol is prepared in a process comprising the steps of:contacting, in an essentially non-water-miscible organic solvent, ethylene oxide with carbon monoxide and hydrogen in the presence of a catalytic amount of a non-phosphine-ligated cobalt compound and an effective amount of a lipophilic quaternary phosphonium salt promoter at a temperature within the range of about 50.degree. to about 100.degree. C. and a pressure within the range of about 500 to about 5000 psig, to produce an intermediate product mixture comprising less than 15 wt % 3-hydroxypropanal;adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid a major portion of the 3-hydroxypropanal at a temperature less than about 100.degree. C.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: October 31, 1995
    Assignee: Shell Oil Company
    Inventors: Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Thomas C. Semple, Paul R. Weider
  • Patent number: 5463144
    Abstract: 1,3-propanediol is prepared in a process comprising the steps of:contacting ethylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of an effective amount of a non-phosphine-ligated cobalt catalyst and an effective amount of a lipophilic quaternary ammonium salt at a temperature within the range of about 50.degree. to about 100.degree. C. and a, pressure within the range of about 500 to about 5000 psig, under reaction conditions effective to produce an intermediate product mixture comprising less than 15 wt % 3-hydroxypropanal;adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid at a temperature less than about 100.degree. C.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: October 31, 1995
    Assignee: Shell Oil Company
    Inventors: Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Terry B. Thomason, Thomas C. Semple, Paul R. Weider, Juan P. Arhancet
  • Patent number: 5401888
    Abstract: The present invention provides a method for preparing allylic alcohols by the palladium-catalyzed cross-coupling of vinylic epoxides and aryl halides, vinylic halides or vinylic triflates.
    Type: Grant
    Filed: February 9, 1993
    Date of Patent: March 28, 1995
    Assignee: Iowa State University Research Foundation, Inc.
    Inventor: Richard C. Larock
  • Patent number: 5397810
    Abstract: The present invention relates to a novel polyol obtained by using a specified polyhydric alcohol, polyoxyalkylene polyol, aliphatic amine and/or alkamlamine as a raw material and adding an organic polycarboxylic acid or its anhydride and an alkylene oxide; a polyurethane resin prepared from said novel polyol and an organic polyisocyanate; a rigid polyurethane foam prepared by using a hydrochlorofluorocarbon or hydrofluorocarbon foaming agent which has very low public hazards; and a composite utilizing thereof.The production of rigid polyurethane foam by using the polyol of the invention can be carried out in good operation efficiency and low public hazards. Additionally, properties of the foam thus obtained is equivalent to those of rigid polyurethane foams obtained by using conventional chlorofluorocarbons. Consequently, the rigid polyurethane foam of the invention is very useful for insulation materials and structural insulation materials.
    Type: Grant
    Filed: February 19, 1993
    Date of Patent: March 14, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Satoshi Ozaki, Tsukuru Izukawa, Haruhiko Kawakami, Takayoshi Masuda, Masayuki Kimura, Toshio Nozawa, Masahiko Hashiba
  • Patent number: 5349110
    Abstract: Disclosed is a process for preparation of monoalkyl ethers by reacting low molecular weight olefins and the corresponding oxiranes, in the presence of a catalyst comprising an acidic heterogeneous or homogeneous catalyst, generally represented by the equation: ##STR1## where R, R', R" may be hydrogen or an alkyl radical.
    Type: Grant
    Filed: August 2, 1993
    Date of Patent: September 20, 1994
    Assignee: Texaco Chemical Company
    Inventor: John F. Knifton
  • Patent number: 5342903
    Abstract: A process for the preparation of adducts by reacting an alcohol with an epoxy compound in the presence of a catalyst, which comprises reacting an alcohol of formula I ##STR1## wherein A is an aliphatic, cycloaliphatic or araliphatic radical and r is a number from 1 to 10, with a mono- or diepoxide in the equivalent ratio of 1:20 to 20:1, based on the hydroxyl and epoxy groups, in the presence of a metal complex of formula II as catalyst[M.sup.n+ (L.sub.1).sub.x (L.sub.2).sub.y (L.sub.3.sup.m-).sub.z ][X.sup.k- ].sub.(n-zm)/k (II),whereinM is a metal of the main groups or subgroups of the Periodic Table of the Elements,L.sub.1 and L.sub.2 are weakly bonded, neutral, unidentale or multidentate ligands,L.sub.3 is a strongly bonded, non-replaceable neutral or anionic unidentale or multidentate ligand,X is an anion of the following formulae BF.sub.4.sup.-, PF.sub.6.sup.-, AsF.sub.6.sup.-, SbF.sub.6.sup.-, ClO.sub.4.sup.-, IO.sub.4.sup.-, NO.sub.3.sup.
    Type: Grant
    Filed: April 30, 1993
    Date of Patent: August 30, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Heinz Wolleb, Andreas Hafner, William M. Rolfe
  • Patent number: 5304691
    Abstract: This invention relates to a process for making 1,3-propanediol and 3-hydroxypropanal by intimately contacting(a) ethylene oxide,(b) tertiary phosphine-complexed cobalt carbonyl catalyst(c) ruthenium catalyst,(c) carbon monoxide, and(d) hydrogen, the molar ratio of carbon monoxide to hydrogen being from about 4:1 to about 1:6,in liquid-phase solution in an inert reaction solvent, at a temperature of from about 30.degree. C. to about 150.degree. C. and a pressure of from about 50 psi to about 10,000 psi.
    Type: Grant
    Filed: July 13, 1993
    Date of Patent: April 19, 1994
    Assignee: Shell Oil Company
    Inventors: Juan P. Arhancet, Lynn H. Slaugh
  • Patent number: 5304686
    Abstract: This invention relates to a process for making 3-hydroxypropanal by intimately contacting(a) ethylene oxide,(b) ditertiary phosphine-modified cobalt carbonyl catalyst, said phosphine being a hydrocarbylene-bis(monophosphabicyclononane) in which each phosphorus atom is joined to hydrocarbylene and is a member of a bridge linkage without being a bridgehead atom and which hydrocarbylene-bis(monophosphabicyclononane) has 18 to 50 carbon atoms, 8 carbon atoms thereof together with a phosphorus atom being members of each of the two bicyclic skeletal structures,(c) a catalyst promoter comprising an acid and a metal salt promoter selected from a salt of a metal of Group IIA, Group IIB, Group IIIB and the Rare Earth Series of the Periodic Table of the Elements (CAS version),(d) carbon monoxide, and(e) hydrogen, the molar ratio of carbon monoxide to hydrogen being from about 4:1 to about 1:6,in liquid-phase solution in an inert reaction solvent, at a temperature of from about 30.degree. C. to about 150.degree. C.
    Type: Grant
    Filed: July 13, 1993
    Date of Patent: April 19, 1994
    Assignee: Shell Oil Company
    Inventors: Lynn H. Slaugh, Juan P. Arhancet
  • Patent number: 5268493
    Abstract: An .alpha.-olefin oxide is produced with an enhanced reaction selectivity by a method in which an .alpha.-olefin having 6 to 30 carbon atoms is epoxidized in an aqueous solution containing hydrogen peroxide, acetic acid, an acid catalyst, for example, sulfuric acid, and a side reaction-inhibiting agent consisting of a water-soluble neutral salt, for example, sodium sulfate, in an amount of 2 to 30% based on the total weight of the aqueous solution, by an in-situ method, while maintaining the pH of the aqueous solution at a level of 0 to 1, and the resultant reaction product is collected.
    Type: Grant
    Filed: December 3, 1992
    Date of Patent: December 7, 1993
    Assignee: Nippon Peroxide Co., Ltd.
    Inventors: Ryuichi Kayama, Hiroshi Igarashi, Toshio Suzuki
  • Patent number: 5260046
    Abstract: A method and apparatus for removal of gaseous epoxides from effluent gas streams is described. The method comprises contacting a gaseous sample suspected of containing gaseous epoxides with a polymer barrier. The polymer barrier is comprised of a superactidic perfluorinated alyl sulfonic acid polymer that is capable of converting a gaseous epoxides to gaseous non-epoxide products. Specifically, the method is capable of removing ethylene oxide and propylene oxide from effluent gas streams with greater than 90% efficiency.
    Type: Grant
    Filed: September 14, 1990
    Date of Patent: November 9, 1993
    Inventor: David J. Pierotti
  • Patent number: 5260495
    Abstract: The invention relates to highly selective, heterogeneous hydrotalcite-type catalysts for the production of monoalkylene glycol by hydrolysis of the corresponding alkylene oxide. The invention also relates to method of preparing these catalysts using large organic anion spacers, and a process for producing monoalkylene glycol.
    Type: Grant
    Filed: August 4, 1992
    Date of Patent: November 9, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Matthew W. Forkner
  • Patent number: 5256827
    Abstract: This invention relates to a process for making 3-hydroxypropanal and 1,3-propanediol which by intimately contacting(a) ethylene oxide,(b) tertiary phosphine-complexed cobalt carbonyl catalyst, wherein said phosphine, prior to being complexed with said cobalt carbonyl catalyst, is partially oxidized to provide an oxygen to phosphorus ratio no greater than about 0.5,(c) carbon monoxide, and(d) hydrogen, the molar ratio of carbon monoxide to hydrogen being from about 4:1 to about 1:6,in liquid-phase solution in an inert reaction solvent, at a temperature of from about 30.degree. C. to about 150.degree. C. and a pressure of from about 50 psi to about 10,000 psi. The use of the partially oxidized tertiary phosphine ligand enhances the activity of the catalyst.
    Type: Grant
    Filed: February 5, 1993
    Date of Patent: October 26, 1993
    Assignee: Shell Oil Company
    Inventors: Lynn H. Slaugh, Paul R. Weider
  • Patent number: 5250743
    Abstract: In accordance with the present invention, a method for the interconvertion of the enantiomers of acyclic 1,2-dihydroxy-3-alkenes or for converting either enantiomer of acylic 1,2-dihydroxy-3-alkenes to the corresponding antipodal 1-hydroxy-2-alkoxy-3-alkene compounds has been discovered, comprising reacting in an acidic reaction media either enantiomer of an acylic vinyl epoxide (which can be derived from the corresponding acyclic 1,2-dihydroxy-3-alkene) with water, alcohol, or a mixture thereof. When substantially optically pure acyclic vinyl epoxide compounds are employed in the inventive method, the interconverted acyclic 1,2-dihydroxy-3-alkene or 1-hydroxy-2-alkoxy-3-alkene compound products are also substantially optically pure.
    Type: Grant
    Filed: December 31, 1992
    Date of Patent: October 5, 1993
    Assignee: Eastman Kodak Company
    Inventor: Neil W. Boaz
  • Patent number: 5218135
    Abstract: A process for the preparation of dialkyl carbonates is described in which an alkylene carbonate is first formed from alkylene oxides and CO.sub.2 and this alkylene carbonate is then transesterified with alkanols. Both reaction steps are carried out in the presence of a bifunctional catalyst of the formula[A.sub.a -X.sub.b ].sub.m .multidot.[B.sub.c Y.sub.d ].sub.n (I)wherein A, B, X, Y and the indices a, b, c, d, m and n have the meaning indicated in the description.
    Type: Grant
    Filed: February 12, 1992
    Date of Patent: June 8, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Josef Buysch, Alexander Klausener
  • Patent number: 5216181
    Abstract: Liquid telechelic polymers are made from dienes and are produced via anionic polymerization. While having low molecular weight, for example less than 15,000, the telechelic polymers are generally gel-free, have high amounts of trans-1,4 structure, low vinyl unsaturation and low bulk viscosities. The liquid telechelic polymers are made utilizing a trimetallic initiator comprised of (1) an organopolylithium compound and (2) a complex of a trialiphatic substituted aluminum compound or derivative thereof and a barium salt of an organic alcohol.
    Type: Grant
    Filed: August 26, 1991
    Date of Patent: June 1, 1993
    Assignee: GenCorp Inc.
    Inventors: I. Glen Hargis, Hubert J. Fabris, John A. Wilson, Russell A. Livigni
  • Patent number: 5210318
    Abstract: A process for producing a 1,3-diol, e.g., 1,3-propanediol, and/or a 3-hydroxyaldehyde, e.g., 3-hydroxypropionaldehyde, is disclosed which comprises contacting a combination of an epoxide, carbon monoxide and hydrogen in the presence of a rhodium-containing catalyst composition effective to promote the hydroformylation of the epoxide at conditions effective to form at least one of a 1,3-diol and a 3-hydroxyaldehyde. The rhodium-containing catalyst composition comprises an anionic rhodium-containing complex. A promoter component is preferably provided to enhance at least one of the rate and selectivity of the epoxide hydroformylation reaction Rhodium-containing compositions and a processes for producing rhodium-containing compositions are also disclosed.
    Type: Grant
    Filed: March 18, 1991
    Date of Patent: May 11, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John R. Briggs, John M. Maher, Arnold M. Harrison
  • Patent number: 5196601
    Abstract: Disclosed herein is a process for producing an alcohol or an amine by reducing a compound having a formyl, keto, nitro, oxirane, ester, nitrile, amide or halogenated carboxyl group with an alkali metal boro-hydride in the presence of a compound having a hydroxyl group and ether linkage. According to the present invention, a functional group having a great steric hindrance can be reduced, and a corresponding alcohol or amine can efficiently be produced under very mild conditions on an industrial scale.
    Type: Grant
    Filed: June 17, 1992
    Date of Patent: March 23, 1993
    Assignee: Kao Corporation
    Inventors: Tomohito Kitsuki, Yoshiaki Fujikura