From Alkylene Oxide Patents (Class 568/867)
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Patent number: 5072059Abstract: A two-step reaction process for converting ethylene oxide with high selectivity into monoethylene glycol which comprises firstly reacting ethylene oxide with acetone in the presence of a solid acid catalyst to form 2,2-dimethyl-1,3-dioxolane and secondly hydrolyzing the 2,2-dimethyl-1,3-dioxolane with water in the presence of a solid acid catalyst to form monoethylene glycol.Type: GrantFiled: November 14, 1990Date of Patent: December 10, 1991Assignee: Shell Oil CompanyInventor: Johan Van Gogh
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Patent number: 5053562Abstract: A process for manufacturing 1,3-glycols is disclosed. The process comprises reacting an epoxide with synthesis gas in the presence of rhodium, a phosphine, and a lower-alkyl iodide or .beta.-hydroxy lower-alkyl iodide.Type: GrantFiled: July 31, 1990Date of Patent: October 1, 1991Assignee: Hoechst Celanese CorporationInventor: Kwoliang D. Tau
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Patent number: 5043480Abstract: A process for producing a .beta.-hydroxyester product or a .beta.-hydroxyaldehyde product from ethylene oxide, carbon monoxide, and, optionally, hydrogen, is disclosed. This process uses, as a catalyst, a catalyst comprising rhodium, ruthenium, and a Group Va promoter.Type: GrantFiled: August 16, 1990Date of Patent: August 27, 1991Assignee: Eastman Kodak CompanyInventor: William A. Beavers
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Catalysts for producing 1,3-diols and/or 3-hydroxyaldehydes, and processes for making and using same
Patent number: 5030766Abstract: A process for producing a 1,3-diol, e.g., 1,3-propanediol, or a 3-hydroxyaldehyde is disclosed which comprises contacting a combination of an epoxide, carbon monoxide and hydrogen in the present of a rhodium-containing catalyst 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 contacting occurring in the substantial absence of a promoting amount of alkali metal ions, and at least a portion of the rhodium-containing catalyst being formed substantially without incorporation of the epoxide. A process for producing such rhodium-containing compositions is also disclosed.Type: GrantFiled: May 4, 1990Date of Patent: July 9, 1991Assignee: Technology CorporationInventors: John R. Briggs, John M. Maher, Arnold M. Harrison -
Patent number: 5001283Abstract: Aromatic alkanols are provided by reacting an aromatic compound with a 1,2-alkylene oxide in the presence of a synthetic porous crystalline material possessing a Constraint Index of not greater than about 3. Thus, for example, isobutylbenzene is reacted with propylene oxide in the presence of zeolite Beta, ZSM-12 or MCM-22 to provide 2-(4-isobutylphenyl)propanol which can thereafter be oxidized to the corresponding carboxylic acid, the widely utilized anti-inflammatory agent ibuprofen (i.e., 2-(4-isobutylphenyl)-propionic acid).Type: GrantFiled: January 24, 1990Date of Patent: March 19, 1991Assignee: Mobil Oil Corp.Inventors: Lawrence J. Altman, Philip J. Angevine, John P. McWilliams
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Patent number: 4983260Abstract: A process for the concentration of ethylene oxide in an impure solution thereof including adding the solution and steam to a distillation column, recovering the gaseous stream therefrom containing ethylene oxide, and progressively condensing the steamed solution in at least two heat exchangers arranged in series, with the absolute pressure of the distillation column and of the exchangers being between about 1.5 and 6 bars and the temperature of the cooling fluid of the last exchanger being between about 5.degree. C. and a maximum temperature 5.degree. C. below the temperature of condensation of pure ethylene oxide at the pressure used.Type: GrantFiled: April 3, 1989Date of Patent: January 8, 1991Inventors: Henri Neel, Francis DeLannoy
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Patent number: 4982021Abstract: Alkylene glycols are produced by the reaction of alkylene oxide with water in the presence of a metalate-containing solid wherein the metalate is in association with electropositive complexing sites on a solid support such as an anion exchange resin.Type: GrantFiled: June 8, 1988Date of Patent: January 1, 1991Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventors: Robert D. Best, Joseph A. Collier, Brian T. Keen, John H. Robson
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Patent number: 4967018Abstract: A process for the catalytic hydrolysis of alkylene oxide to alkylene glycol using a hydrothermally stable, mixed metal framework catalyst composition selected from(a) material having the formulaM.sub.x.sup.2+ Q.sub.y.sup.3+ (OH) 2x+3y-nz A.sub.z.sup.n-. a 1 H.sub.2 O (I)wherein M is at least one divalent metal cation; Q is at least one trivalent metal cation; and A is at least one anion providing a valence (n.sup.31), wherein n is at least 1, and wherein a is a positive number, M, Q, and A are provided in a proportion such that x/y is a number equal to or greater than 1, z has a value greater than zero and 2x+3y-nz is a positive number, and M, Q and A are selected to provide a layered structure, and(b) material prepared by calcining the material of formula (I) having the formulaM.sub.x.sup.2+ Q.sub.y.sup.3+ (O).sub.(2x+3y-nz)/2D.sub.z.sup.n-(II)wherein M, Q, x, y, z and n have the same meanings defined above in connection with formula (I) and D is at least one nonvolatile anion.Type: GrantFiled: October 18, 1989Date of Patent: October 30, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventors: Hwaili Soo, Bernard C. Ream, John H. Robson
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Patent number: 4960754Abstract: Described are 3,7-dimethyl-6,7-dioxo-1,3-octadienes or mixtures of same defined according to the structure: ##STR1## wherein R is hydrogen or ethyl and X is one of the moieties: ##STR2## and wherein the wavy lines represent a "E" or "Z" configuration of the methyl and vinyl moiety about the 3,4-pi-bond of the molecule, as well as methods for methods for augmenting or enhancing the aroma of consumable materials including perfumes, colognes and perfumed articles by adding thereto an aroma augmenting or enhancing quantity of at least one of said 3,7-dimethyl-6,7-dioxo-1,3-octadienes.Type: GrantFiled: December 8, 1989Date of Patent: October 2, 1990Assignee: International Flavors & Fragrances Inc.Inventors: Richard A. Wilson, Michael J. Zampino, Braja D. Mookherjee, Robert W. Trenkle, Anton Van Ouwerkerk, Myrna L. Hagedorn, Michael G. Monteleone
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Patent number: 4937393Abstract: In the manufacturing method of ethylene glycol and/or propylene glycol, these glycols can be prepared with a highly selectivity and at a high yield by applying the catalyst comprising a carboxylic acid and a carboxylic acid salt or a metal salt of formic acid alone.Type: GrantFiled: May 17, 1988Date of Patent: June 26, 1990Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Takayoshi Masuda, Katuyoshi Asano, Naomi Hori, Shinji Ando
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Patent number: 4935554Abstract: A process for manufacturing 1,3-glycols is disclosed. The process comprises reacting an epoxide with synthesis gas in the presence of rhodium and a phosphine.Type: GrantFiled: July 17, 1989Date of Patent: June 19, 1990Assignee: Hoechst Celanese CorporationInventors: Mark A. Murphy, Brad L. Smith, Adolfo' Aguilo', Kwoliang D. Tau
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Patent number: 4873378Abstract: A process for manufacturing 1,3-glycols is disclosed. The process comprises reacting an epoxide with synthesis gas in the presence of rhodium and a phosphine.Type: GrantFiled: December 15, 1987Date of Patent: October 10, 1989Assignee: Hoechst Celanese CorporationInventors: Mark A. Murphy, Brad L. Smith, Adolfo Aguilo', Kwoliang D. Tau
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Patent number: 4873379Abstract: A process for manufacturing 1,3-glycols is disclosed. The process comprises reacting an epoxide with synthesis gas in the presence of rhodium in the presence of an alkali metal compound.Type: GrantFiled: May 25, 1988Date of Patent: October 10, 1989Assignee: Hoechst Celanese CorporationInventor: Mark A. Murphy
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Patent number: 4870208Abstract: A process of preparing chiral alcohols by the asymmetric catalytic hydrogenolysis of epoxides using rhodium or ruthenium catalysts containing chiral phosphine ligands.Type: GrantFiled: June 3, 1988Date of Patent: September 26, 1989Assignee: Monsanto CompanyInventors: Albert S. C. Chan, James P. Coleman, Grace M. Wagner
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Patent number: 4831196Abstract: A high efficiency process for removal and detoxification of olefin oxides from gas compositions is described. The process consists of olefin oxide absorption at ambient pressure in an absorber using an aqueous liquid as the absorbing medium and subsequent hydrolysis of the olefin oxide to products including an alkylene glycol in a chemical reactor operating at a controlled temperature and pH in the presence of an acid catalyst. The absorption stage is favored by low temperature and high liquid to gas ratios. More than 99% of an olefin oxide contained in a gas stream can be effectively removed in the absorption stage. The hydrolysis stage is favored by low pH conditions. More than 99% of the incoming olefin oxide to the reactor can be converted to alkylene glycols. The process has a capability of removing and detoxifying olefin oxide from gas streams with an overall effectiveness exceeding 98%. The process also provides for recovering inert diluent contained in the gas compositions.Type: GrantFiled: April 5, 1988Date of Patent: May 16, 1989Assignee: Chemrox, Inc.Inventors: Anthony J. Buonicore, Pankaj R. Desai
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Patent number: 4822925Abstract: Novel vicinal dioxyalkylene organometalates comprising a cation having a hydrocarbyl-containing substituent are disclosed. The vicinal dioxyalkylene organometalates can be reacted with water to yield alkylene glycols.Type: GrantFiled: February 6, 1987Date of Patent: April 18, 1989Assignee: Union Carbide CorporationInventors: John R. Briggs, John H. Robson
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Patent number: 4822926Abstract: A process for the recovery of a low concentration of ethylene oxide from an aqueous solution comprising salts, ethylene oxide and glycol which comprises the steps of:(1) passing the aqueous solution comprising salts and ethylene oxide through a hydrolyzing zone at elevated temperature and elevated pressure for a sufficient length of time to insure the conversion of at least the greater portion of the ethylene oxide to glycols to obtain a dilute aqueous glycol solution;(2) passing the dilute aqueous glycol solution through at least one flasher, wherein water is evaporated in the form of steam thereby producing at the bottom of the (last) flasher a solid-liquid two-phase slurry stream comprising salt-containing solids and a liquid phase comprising glycol, salt and water;(3) sending said slurry-containing stream coming out of the (last) flasher to a centrifuge and centrifuging such stream to produce a solid phase and a liquid phase; and(4) passing said centrifuged liquid phase to a flasher wherein glycols are seType: GrantFiled: February 29, 1988Date of Patent: April 18, 1989Assignee: Shell Oil CompanyInventor: Robert F. Dye
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Patent number: 4812292Abstract: Chemical sterilants such as ethylene oxide are recovered from sterilization processes and converted into safer chemical compounds by non-catalytic hydrolysis.Type: GrantFiled: October 26, 1987Date of Patent: March 14, 1989Assignee: Joslyn Valve CorporationInventor: Larry Joslyn
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Patent number: 4801759Abstract: A method for the continuous saponification of epoxides with 3-8 carbon atoms at low pressures, preferably atmospheric pressure, and low boiling temperatures with small amounts of water. Yields and selectivities are very high.Type: GrantFiled: August 7, 1987Date of Patent: January 31, 1989Assignee: Degussa AktiengesellschaftInventors: Rainer Siegmeier, Gu Prescher, Helmut Maurer
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Patent number: 4762954Abstract: The continuous production of 1,2-diols by means of saponification of aliphatic, linear or branched epoxides with 8-30 carbon atoms or high molecular weight cycloaliphatic epoxides with water and acidic catalyst at pressures of 1-5 bar using a vapor-liquid mixture of a solubilizing agent which is stationary in a column. The yields obtained are high and exhibit a high degree of purity. The water added can be recycled as such.Type: GrantFiled: August 7, 1987Date of Patent: August 9, 1988Assignee: Degussa AktiengesellschaftInventors: Rainer Siegmeier, Gunther Prescher, Helmut Maurer
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Patent number: 4760200Abstract: The process for the liquid-phase hydration of a vicinal alkylene oxide(s) to the corresponding alkylene glycol(s) comprising carrying out such hydration in an aqueous medium containing a water miscible alkylene glycol ether co-solvent.Type: GrantFiled: December 31, 1985Date of Patent: July 26, 1988Assignee: Union Carbide CorporationInventors: Brian T. Keen, John H. Robson, George E. Keller, II
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Patent number: 4701571Abstract: An improved process for the hydrolysis of alkylene oxide to produce alkylene glycol which comprises:(a) reacting alkylene oxide and water in the presence of a selectivity-enhancing metalate-containing solid until about 90-95% of the alkylene oxide is converted to alkylene glycol; and(b) completing the hydrolysis reaction of (a) in the absence of the selectivity-enhancing metalate-containing solid.Type: GrantFiled: June 30, 1986Date of Patent: October 20, 1987Assignee: Union Carbide CorporationInventors: Hwaili Soo, John H. Robson
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Patent number: 4626603Abstract: Aliphatic or cyclic epoxides containing 3 to 8 carbon atoms which are present in aromatic hydrocarbons or halohydrocarbons are saponified continuously and directly to vicinal diols without the use of high temperatures and pressures which would otherwise be necessary. The saponification is acid catalyzed.Type: GrantFiled: November 15, 1985Date of Patent: December 2, 1986Assignee: Degussa AktiengesellschaftInventors: Rainer Siegmeier, Gunter Prescher, Helmut Maurer
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Patent number: 4605795Abstract: There is provided a process for the continuous production of pentanediol-1,2 comprising epoxidizing pentene in a completely homogeneous phase with perpropionic acid in benzene to 1-pentene oxide and directly saponifying the pentene oxide-1 without isolation. High yields and a high degree of purity of pentanediol-1,2 are obtained.Type: GrantFiled: November 15, 1985Date of Patent: August 12, 1986Assignee: Degussa AktiengesellschaftInventors: Rainer Siegmeier, Gunter Prescher, Helmut Maurer, Gunter Hering
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Patent number: 4599467Abstract: A process is provided for production of vicinal alkylene glycols by hydrolysis of an epoxyalkane having from 6 to 24 carbon atoms in the presence of water and a basic catalyst and under carbon dioxide pressures of from 100 to 300 bars and temperatures of from about 200.degree. C. to 350.degree. C. Also disclosed are homogeneous mixtures of epoxyalkanes and/or vicinal alkylene glycols having from 6 to 24 carbon atoms, water, a basic catalyst and carbon dioxide in an amount corresponding to a carbon dioxide partial pressure of from about 100 to 300 bars, provided at temperatures from about 200.degree. C. to 350.degree. C. The process provides high yields, selectivities and reaction velocities and the resulting products are of high purity.Type: GrantFiled: April 10, 1985Date of Patent: July 8, 1986Assignee: AKZO NVInventors: Hilde Kersten, Gerhard Meyer
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Patent number: 4579982Abstract: Alkylene oxides are hydrolyzed in a reaction menstruum containing an aqueous phase, a water-immiscible liquid phase, and a selectivity-enhancing, dissociatable metalate anion-containing material. The concentration of the metalate anion-containing material is greater in the water-immiscible liquid phase than that in the aqueous phase. The water-immiscible liquid phase can be separated from the aqueous phase to recover metalate anion-containing material.Type: GrantFiled: March 28, 1984Date of Patent: April 1, 1986Assignee: Union Carbide CorporationInventors: John R. Briggs, John H. Robson
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Patent number: 4579983Abstract: In processes for the hydrolysis of alkylene oxide to form alkylene glycols in the presence of selectivity-enhancing organometalate wherein the organometalate is provided in a water-insoluble phase, a stabilizing material is used to enhance the stability of the organometalate. The stabilizing material is water-soluble and comprises a cation and a selectivity-enhancing metalate anion.Type: GrantFiled: March 28, 1984Date of Patent: April 1, 1986Assignee: Union Carbide CorporationInventor: Brian T. Keen
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Patent number: 4578524Abstract: The process for the liquid-phase hydration of a vicinal alkylene oxide(s) to the corresponding alkylene glycol(s) comprising carrying out such hydration in the presence of vanadate anion and a selectivity-enhancing amount of carbon dioxide.Type: GrantFiled: March 28, 1984Date of Patent: March 25, 1986Assignee: Union Carbide CorporationInventor: Brian T. Keen
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Patent number: 4571440Abstract: A continuous process for making alkylene glycols by the hydrolysis of alkylene oxides in the presence of selectivity-enhancing organometalate wherein the alkylene glycol-containing hydrolysis product contains organometalate comprises recovering organometalate by extraction with a water-immiscible solvent, separating the resulting organometalate-containing solvent into an organometalate-lean stream for reuse in the extraction and an organometalate-rich stream for reuse in the hydrolysis.Type: GrantFiled: October 23, 1984Date of Patent: February 18, 1986Assignee: Union Carbide CorporationInventors: Brian T. Keen, John H. Robson
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Patent number: 4564715Abstract: High selectivity to monoalkylene glycol is obtained by contacting in an associated moiety-forming zone alkylene oxide and a selectivity enhancing, dissociatable metalate anion under conditions sufficient to associate at least a portion of the alkylene oxide with metalate anion, and then contacting the associated moiety with water in a glycol-forming zone to form alkylene glycol. The alkylene glycol can be separated from metalate anion. Desirably, the metalate anion can be recycled to the associated moiety-forming zone.Type: GrantFiled: October 23, 1984Date of Patent: January 14, 1986Assignee: Union Carbide CorporationInventors: John R. Briggs, George L. O'Connor, John H. Robson
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Patent number: 4560813Abstract: In processes for making alkylene glycols by the hydrolysis of alkylene oxides in the presence of selectivity-enhancing metalate anion-containing material, metalate anion can be recovered from the alkylene glycol-containing hydrolysis product by contact with a solid having electropositive complexing sites thereon such as anion exchange resins.Type: GrantFiled: March 28, 1984Date of Patent: December 24, 1985Assignee: Union Carbide CorporationInventor: Joseph A. Collier
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Patent number: 4551566Abstract: The process for the liquid-phase hydration of a vicinal alkylene oxide(s) to the corresponding alkylene glycol(s) comprising carrying out such hydration in the presence of a vanadate salt wherein the pH of the liquid phase is between about 5 and 12.Type: GrantFiled: September 8, 1983Date of Patent: November 5, 1985Assignee: Union Carbide CorporationInventors: John H. Robson, George E. Keller, II
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Patent number: 4504685Abstract: Hydroxyl compounds are oxyalkylated by contacting them with an alkylene oxide, such as ethylene oxide or propylene oxide, in the presence of a perfluorocarbon polymer containing pendant sulfonic acid groups.Type: GrantFiled: August 19, 1980Date of Patent: March 12, 1985Assignee: Varen TechnologyInventor: Ronald J. Vaughan
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Patent number: 4487854Abstract: The invention relates to polyols prepared by reacting ethylene oxide with an initiator followed by additional alkylene oxide. The ethylene oxide blocks at the initiator ranges from 1 to 30 weight percent based on the weight of the polyol. Polyurethane foams prepared from these polyols exhibit good air flow and improved load bearing properties.Type: GrantFiled: December 27, 1983Date of Patent: December 11, 1984Assignee: BASF Wyandotte CorporationInventor: Robert J. Hartman
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Patent number: 4434105Abstract: A process for preparing a dialkyl carbonate which comprises contacting an alkylene oxide with an aliphatic or cycloaliphatic alcohol and carbon dioxide in the presence of a catalyst at an elevated temperature.Type: GrantFiled: June 27, 1980Date of Patent: February 28, 1984Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Buysch, Heinrich Krimm, Hans Rudolph
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Patent number: 4409403Abstract: This invention relates to oxyalkylations which take place in the presence of solid acid catalysts. More particularly this invention relates to increasing the selectivity of such processes employing a solid acid catalyst, preferably a polyfluorosulfonic acid catalyst, in which an hydroxylic compound reactant reacts with an alkylene oxide reactant to produce a desired mono-oxyalkylated product which tends to react with the alkylene oxide to produce an undesired second product.Type: GrantFiled: September 28, 1981Date of Patent: October 11, 1983Assignee: Varen TechnologyInventor: Ronald J. Vaughan
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Patent number: 4393254Abstract: A process for the production of alkylene glycols is disclosed which comprises hydrating alkylene oxide in the presence of a partially amine-neutralized sulfonic acid catalyst.Type: GrantFiled: January 12, 1981Date of Patent: July 12, 1983Assignee: Texaco Inc.Inventors: Fred L. Johnson, Jr., Lewis W. Watts, Jr.
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Patent number: 4390738Abstract: Olefine oxides or derivatives thereof such as glycols are produced by reacting an olefinic compound e.g. ethylene, propylene or butadiene with oxygen in the presence of a catalyst containing copper bonded to a peroxo group.Type: GrantFiled: June 18, 1981Date of Patent: June 28, 1983Assignee: Imperial Chemical Industries PLCInventors: Dhafir Y. Waddan, Derek Williams
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Patent number: 4359589Abstract: An improved process for making linear polyethers having a relatively narrow molecular weight distribution comprises contacting a monoepoxide with a salt selected from the group consisting of fluoborate, fluophosphate, fluoantimonate and fluoarsenate salts of a metal selected from the group consisting of alkali metals, alkaline earth metals, lead, nickel, aluminum, cadmium, cobalt, tin, zinc and copper in the presence of a hydroxyl-containing compound at a controlled temperature of about -78.degree. C. to less than +20.degree. C. and in the absence of any additional acid.Type: GrantFiled: July 27, 1981Date of Patent: November 16, 1982Assignee: Shell Oil CompanyInventor: Thomas F. Brownscombe
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Patent number: 4358625Abstract: A method is disclosed for obtaining high-purity ethylene glycols in which the improvement consists in reducing the oxygen-containing organic impurities by treating their aqueous solutions as obtained during the processing of ethylene oxide with a solution of an alkali metal borohydride, sodium borohydride being preferred.A definitely alkaline environment is preferred. Ethylene glycols can thus be obtained which are particularly suitable for use in the fibre-manufacturing industry. Such glycols have extremely low UV-absorbance values.Type: GrantFiled: March 9, 1979Date of Patent: November 9, 1982Assignee: Snamprogetti, S.p.A.Inventors: Alberto Paggini, Ugo Romano, Donato Furlone, Domenico Sanfilippo
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Patent number: 4349417Abstract: Ethylene oxide and water are reacted in a reactor and the reaction product is subjected to distillation in a plurality of distillation columns, in the first columns water and components having a boiling point below that of monoethylene glycol and higher ethylene glycols, if any, being distilled off. To obtain extremely pure monoethylene glycol alkali metal compounds are added at a point between the reactor and the monoethylene glycol distillation column in an amount to adjust the pH of the product entering the latter column to a value of from 7 to 10. The monoethylene glycol obtained in this manner is especially pure and has very low UV absorption values. It is, therefore, especially suitable for the manufacture of polyester fibers.Type: GrantFiled: January 9, 1981Date of Patent: September 14, 1982Assignee: Hoechst AktiengesellschaftInventors: Siegfried Rebsdat, Sigmund Mayer, Josef Alfranseder, Iwo Schaffelhofer
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Patent number: 4339616Abstract: A process for the preparation of 1,2-diols having at least 4 carbon atoms by hydrolysis of the corresponding 1,2-epoxide compound with water in the presence of catalysts at elevated temperatures characterized in that salts of primary, secondary and/or tertiary amines with organic and/or inorganic acids, and/or quaternary ammonium salts, are used as catalysts.Type: GrantFiled: September 15, 1980Date of Patent: July 13, 1982Assignees: Henkel Kommanditgesellschaft auf Aktien, Deutsche Gold-und Silberscheide Anstalt Vormals RoesslerInventors: Horst Rutzen, Wolfgang Rupilius
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Patent number: 4307256Abstract: A process for the preparation of alkylene glycols starting from the corresponding alkylene oxide, which is reacted with water in the presence of carbon dioxide, wherein the reaction catalyst is selected amongst the organic bases, preferably a tertiary amine, whereby the conversion rate and the selectivity are improved.Type: GrantFiled: April 8, 1976Date of Patent: December 22, 1981Assignee: Anic S.p.A.Inventors: Gioacchino Cipriani, Carlo Neri, Ugo Romano
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Patent number: 4277632Abstract: A process for the production of alkylene glycols, which comprises causing a corresponding alkylene oxide to react with water in the presence of a catalyst of at least one member selected from the group consisting of molybdenum and tungsten.Type: GrantFiled: September 19, 1979Date of Patent: July 7, 1981Assignee: Nippon Shokubai Kaguku Kogyo Co., Ltd.Inventors: Toshihiko Kumazawa, Takeshi Yamamoto, Hiroshi Odanaka
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Patent number: 4272455Abstract: A method for the formation of monoalkyleneglycols, monoalkanolamines and alkylenediamines, comprising the steps of: (a) reacting ammonia or ammonium carbonate with an alkylenecarbonate to form a carbamate, (b) heating the carbamate to form a monoalkyleneglycol, an alkyleneurea and a 2-oxazolidinone, (c) further reacting the alkyleneurea and the 2-oxazolidinone with ammonium hydroxide to form ammonia or ammonium carbonate, a monoalkanolamine, and an alkylenediamine, (d) separating the ammonia or ammonium carbonate, the monoalkyleneglycol, the alkylenediamine, and the monoalkanolamine, and (e) recycling the ammonia or ammonium carbonate to reaction step (a).Type: GrantFiled: December 26, 1979Date of Patent: June 9, 1981Assignee: The Dow Chemical CompanyInventors: Frank T. Cook, Daniel W. Baugh, Jr., Robert V. Chambers, Jr.
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Patent number: 4229378Abstract: The present invention provides a novel process for the production of 1-phenyl-3-(3-trifluoromethylphenyl)-2-propanone. The process comprises the steps of:(a) condensing 3-trifluoromethylbenzaldehyde with acetophenone under basic conditions to form a substituted chalcone,(b) epoxidation of the substituted chalcone to produce the corresponding epoxide,(c) converting the epoxide to a chlorohydrin,(d) catalytic hydrogenolysis of the chlorohydrin to produce a diol and subsequently converting the diol into the corresponding alcohol, and(e) oxidizing the alcohol to produce 1-phenyl-3-(3-trifluoromethylphenyl)-2-propanone.Type: GrantFiled: May 14, 1979Date of Patent: October 21, 1980Assignee: Hooker Chemicals & Plastics Corp.Inventors: David Y. Tang, Arthur M. Foster
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Patent number: 4165440Abstract: An improved process for the low temperature preparation of ethylene glycol by the catalytic hydration of ethylene oxide using a fluorinated alkyl sulfonic acid ion exchange resin is described.Type: GrantFiled: October 3, 1977Date of Patent: August 21, 1979Assignee: Shell Oil CompanyInventor: Leo Kim
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Patent number: 4160116Abstract: Process for the production of an alkylene glycol in which the hydration of an alkylene oxide is carried out in the presence of carbon dioxide using a quaternary phosphonium salt as a catalyst.Type: GrantFiled: August 28, 1978Date of Patent: July 3, 1979Assignee: Showa Denko K.K.Inventors: Michihiro Mieno, Hideki Mori, Jun Nakanishi, Juichi Kasai
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Patent number: 4141922Abstract: A method is provided for the removal of 2-chloroethanol from 1,2-dichloroethane (EDC) mixtures containing chloral comprising(1) placing the EDC/2-chloroethanol mixture at a pH of at least 10,(2) partially distilling said basic mixture to remove ethylene oxide from the resulting mixture of (1),(3) mixing the distillate with water in contact with a strong non-halogen acid catalyst to form an aqueous and organic phase, and(4) recovering the reaction product of (3) while separating and disposing the aqueous phase.Type: GrantFiled: February 21, 1978Date of Patent: February 27, 1979Assignee: Continental Oil CompanyInventor: Ronald J. Convers
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Patent number: 4123444Abstract: 2-Alkoxytetrahydrofurans are prepared by hydroformylation of an allylic alcohol in the presence of an alkanol and a rhodium hydroformylation catalyst. The products are useful, inter alia, as intermediates in the preparation of butanediols and substituted derivatives thereof.Type: GrantFiled: June 13, 1977Date of Patent: October 31, 1978Assignee: General Electric CompanyInventor: William E. Smith