From Alkylene Oxide Patents (Class 568/867)
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Patent number: 6362276Abstract: 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: GrantFiled: January 6, 1999Date of Patent: March 26, 2002Assignee: Debio Recherche Pharmaceutique S.A.Inventors: J. Milton Harris, Xuan Zhao
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Patent number: 6348632Abstract: 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: GrantFiled: May 12, 2000Date of Patent: February 19, 2002Assignee: Samsung Electronics Co. Ltd.Inventors: Byeong-No Lee, Byung-Soon Chen
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Publication number: 20020010378Abstract: 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: ApplicationFiled: April 27, 2001Publication date: January 24, 2002Inventors: Yukihiko Kakimoto, Yoshihisa Oka
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Patent number: 6329558Abstract: 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: GrantFiled: June 23, 2000Date of Patent: December 11, 2001Assignee: BASF AktiengesellschaftInventors: Jürgen Mohr, Toni Dockner
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Patent number: 6323374Abstract: Ethylene oxide is hydroformylated to 3-hydroxypropanal using a non-phosphine-ligated cobalt catalyst and an amide promoter.Type: GrantFiled: June 15, 2001Date of Patent: November 27, 2001Assignee: Arco Chemical Technology, L.P.Inventor: Yuan-Zhang Han
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Patent number: 6316571Abstract: 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: GrantFiled: August 24, 2000Date of Patent: November 13, 2001Assignee: Shell Oil CompanyInventor: Eugene Marie Godfried Andre Van Kruchten
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Publication number: 20010016624Abstract: 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: ApplicationFiled: April 2, 2001Publication date: August 23, 2001Applicant: Debio Recherche Pharmaceutique S.A.Inventors: J. Milton Harris, Xuan Zhao
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Publication number: 20010011147Abstract: 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: ApplicationFiled: January 12, 2001Publication date: August 2, 2001Inventors: Andrzej Krueger, Boguslaw Tkacz, Winicjusz Stanik, Leszek Ziemianski, Kazimierz Chlobowski, Kazimierz Szymanski, Ryszard Kosciuk, Wladyslaw Millan, Anna Rzodeczko, Jan Poskrobko, Wojciech Balcerowiak, Jerzy Jasienkiewicz
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Patent number: 6265625Abstract: 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: GrantFiled: December 1, 1999Date of Patent: July 24, 2001Assignee: BASF AktiengesellschaftInventors: Frans Vansant, Jozef de Hert, Dieter Köffer, Gerhard Theis, Winfried Terjung
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Patent number: 6242655Abstract: 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: GrantFiled: July 11, 2000Date of Patent: June 5, 2001Assignee: Scientific Design Company, Inc.Inventor: Mansoor Husain
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Patent number: 6211419Abstract: 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: GrantFiled: April 24, 2000Date of Patent: April 3, 2001Assignee: The Dow Chemical CompanyInventors: Gary R. Strickler, Von G. Landon, Guo-Shuh John Lee
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Patent number: 6160187Abstract: 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: GrantFiled: December 8, 1998Date of Patent: December 12, 2000Assignee: The Dow Chemical CompanyInventors: Gary R. Strickler, Von G. Landon, Guo-shuh John Lee, William J. Rievert
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Patent number: 6156942Abstract: 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: GrantFiled: December 14, 1998Date of Patent: December 5, 2000Assignee: Shell Oil CompanyInventors: Michael Francis Lemanski, Eugene Marie Godfried Andre Van Kruchten, Robert Kunin
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Patent number: 6153801Abstract: 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: GrantFiled: December 9, 1999Date of Patent: November 28, 2000Assignee: Shell Oil CompanyInventor: Eugene Marie Godfried Andre Van Kruchten
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Patent number: 6147265Abstract: 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: GrantFiled: April 27, 1998Date of Patent: November 14, 2000Assignee: Mitsubishi Chemical CorporationInventors: Tomoatsu Iwakura, Hidekazu Miyagi
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Patent number: 6137015Abstract: 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: GrantFiled: December 8, 1998Date of Patent: October 24, 2000Assignee: The Dow Chemical CompanyInventors: Gary R. Strickler, Von G. Landon, Guo-shuh John Lee, William J. Rievert
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Patent number: 6137014Abstract: 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: GrantFiled: October 30, 1998Date of Patent: October 24, 2000Assignee: Shell Oil CompanyInventor: Eugene Marie Godfried Andre Van Kruchten
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Patent number: 6124508Abstract: 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: GrantFiled: December 9, 1999Date of Patent: September 26, 2000Assignee: Shell Oil CompanyInventor: Eugene Marie Godfried Andre Van Kruchten
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Patent number: 6103941Abstract: 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: GrantFiled: September 6, 1995Date of Patent: August 15, 2000Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Christoph Sigwart
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Patent number: 5945570Abstract: 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: GrantFiled: October 29, 1998Date of Patent: August 31, 1999Inventors: Juan Pedro Arhancet, Paul Himelfarb, Joseph Broun Powell, Robert Alfred Plundo, Mohammed Shahjahan Kazi, William Joseph Carrick
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Patent number: 5874653Abstract: 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: GrantFiled: November 25, 1996Date of Patent: February 23, 1999Assignee: Shell Oil CompanyInventor: Eugene Marie Godfried Andre Van Kruchten
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Patent number: 5844070Abstract: 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: GrantFiled: May 16, 1997Date of Patent: December 1, 1998Assignee: Arco Chemical Technology, L.P.Inventors: John E. Hayes, Leah J. Langsdorf, Bruce H. Isaacs, Fred J. Armellini
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Patent number: 5841003Abstract: 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: GrantFiled: July 23, 1996Date of Patent: November 24, 1998Assignee: Shell Oil CompanyInventors: Lynn Henry Slaugh, Paul Richard Weider, Joseph Broun Powell
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Patent number: 5763691Abstract: 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: GrantFiled: November 26, 1996Date of Patent: June 9, 1998Assignee: Mitsubishi Chemical CorporationInventors: Kazuki Kawabe, Kazuhiko Murata, deceased, Toshiyuki Furuya
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Patent number: 5731478Abstract: 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: GrantFiled: October 15, 1996Date of Patent: March 24, 1998Assignee: Shell Oil CompanyInventors: Lynn Henry Slaugh, Paul Richard Weider, Joseph Broun Powell, Juan Pedro Arhancet
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Patent number: 5728796Abstract: 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: GrantFiled: May 31, 1996Date of Patent: March 17, 1998Assignee: The Dow Chemical CompanyInventors: Zeng K. Liao, James L. Bertram
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Patent number: 5723389Abstract: 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: GrantFiled: October 15, 1996Date of Patent: March 3, 1998Assignee: Shell Oil CompanyInventors: Lynn Henry Slaugh, Paul Richard Weider, Joseph Broun Powell, Juan Pedro Arhancet
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Patent number: 5561217Abstract: 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: GrantFiled: April 24, 1995Date of Patent: October 1, 1996Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Weyer, Rolf Fischer, Rolf Pinkos
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Patent number: 5545767Abstract: 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: GrantFiled: September 30, 1994Date of Patent: August 13, 1996Assignee: Shell Oil CompanyInventors: Paul R. Weider, Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Thomas C. Semple
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Patent number: 5545712Abstract: 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: GrantFiled: August 23, 1995Date of Patent: August 13, 1996Assignee: Mitsu Toatsu Chemicals, Inc.Inventors: Tomoki Tsutsui, Tsukuru Izukawa, Kazuhiko Ohkubo, Yoshitsugu Sakaki
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Patent number: 5493035Abstract: 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: GrantFiled: March 24, 1995Date of Patent: February 20, 1996Assignee: Arco Chemical Technology, L.P.Inventors: Ahmad Soltani-Ahmadi, Thomas C. Mullin
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Patent number: 5488184Abstract: 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: GrantFiled: January 31, 1995Date of Patent: January 30, 1996Assignee: Shell Oil CompanyInventors: Willem G. Reman, Eugene M. G. A. Van Kruchten
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Patent number: 5468840Abstract: 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: GrantFiled: August 29, 1994Date of Patent: November 21, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tomoki Tsutsui, Tsukuru Izukawa, Kazuhiko Ohkubo, Yoshitsugu Sakaki
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Patent number: 5463145Abstract: 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: GrantFiled: September 30, 1994Date of Patent: October 31, 1995Assignee: Shell Oil CompanyInventors: Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Thomas C. Semple, Paul R. Weider
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Patent number: 5463144Abstract: 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: GrantFiled: September 30, 1994Date of Patent: October 31, 1995Assignee: Shell Oil CompanyInventors: Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Terry B. Thomason, Thomas C. Semple, Paul R. Weider, Juan P. Arhancet
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Patent number: 5401888Abstract: 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: GrantFiled: February 9, 1993Date of Patent: March 28, 1995Assignee: Iowa State University Research Foundation, Inc.Inventor: Richard C. Larock
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Patent number: 5397810Abstract: 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: GrantFiled: February 19, 1993Date of Patent: March 14, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Satoshi Ozaki, Tsukuru Izukawa, Haruhiko Kawakami, Takayoshi Masuda, Masayuki Kimura, Toshio Nozawa, Masahiko Hashiba
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Patent number: 5349110Abstract: 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: GrantFiled: August 2, 1993Date of Patent: September 20, 1994Assignee: Texaco Chemical CompanyInventor: John F. Knifton
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Patent number: 5342903Abstract: 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: GrantFiled: April 30, 1993Date of Patent: August 30, 1994Assignee: Ciba-Geigy CorporationInventors: Heinz Wolleb, Andreas Hafner, William M. Rolfe
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Patent number: 5304691Abstract: 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: GrantFiled: July 13, 1993Date of Patent: April 19, 1994Assignee: Shell Oil CompanyInventors: Juan P. Arhancet, Lynn H. Slaugh
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Patent number: 5304686Abstract: 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: GrantFiled: July 13, 1993Date of Patent: April 19, 1994Assignee: Shell Oil CompanyInventors: Lynn H. Slaugh, Juan P. Arhancet
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Patent number: 5268493Abstract: 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: GrantFiled: December 3, 1992Date of Patent: December 7, 1993Assignee: Nippon Peroxide Co., Ltd.Inventors: Ryuichi Kayama, Hiroshi Igarashi, Toshio Suzuki
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Patent number: 5260046Abstract: 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: GrantFiled: September 14, 1990Date of Patent: November 9, 1993Inventor: David J. Pierotti
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Patent number: 5260495Abstract: 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: GrantFiled: August 4, 1992Date of Patent: November 9, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Matthew W. Forkner
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Patent number: 5256827Abstract: 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: GrantFiled: February 5, 1993Date of Patent: October 26, 1993Assignee: Shell Oil CompanyInventors: Lynn H. Slaugh, Paul R. Weider
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Patent number: 5250743Abstract: 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: GrantFiled: December 31, 1992Date of Patent: October 5, 1993Assignee: Eastman Kodak CompanyInventor: Neil W. Boaz
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Patent number: 5218135Abstract: 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: GrantFiled: February 12, 1992Date of Patent: June 8, 1993Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Buysch, Alexander Klausener
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Patent number: 5216181Abstract: 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: GrantFiled: August 26, 1991Date of Patent: June 1, 1993Assignee: GenCorp Inc.Inventors: I. Glen Hargis, Hubert J. Fabris, John A. Wilson, Russell A. Livigni
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Patent number: 5210318Abstract: 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: GrantFiled: March 18, 1991Date of Patent: May 11, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: John R. Briggs, John M. Maher, Arnold M. Harrison
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Patent number: 5196601Abstract: 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: GrantFiled: June 17, 1992Date of Patent: March 23, 1993Assignee: Kao CorporationInventors: Tomohito Kitsuki, Yoshiaki Fujikura