From Alkylene Oxide Patents (Class 568/867)
  • Patent number: 5072059
    Abstract: 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: Grant
    Filed: November 14, 1990
    Date of Patent: December 10, 1991
    Assignee: Shell Oil Company
    Inventor: Johan Van Gogh
  • Patent number: 5053562
    Abstract: 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: Grant
    Filed: July 31, 1990
    Date of Patent: October 1, 1991
    Assignee: Hoechst Celanese Corporation
    Inventor: Kwoliang D. Tau
  • Patent number: 5043480
    Abstract: 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: Grant
    Filed: August 16, 1990
    Date of Patent: August 27, 1991
    Assignee: Eastman Kodak Company
    Inventor: William A. Beavers
  • Patent number: 5030766
    Abstract: 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: Grant
    Filed: May 4, 1990
    Date of Patent: July 9, 1991
    Assignee: Technology Corporation
    Inventors: John R. Briggs, John M. Maher, Arnold M. Harrison
  • Patent number: 5001283
    Abstract: 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: Grant
    Filed: January 24, 1990
    Date of Patent: March 19, 1991
    Assignee: Mobil Oil Corp.
    Inventors: Lawrence J. Altman, Philip J. Angevine, John P. McWilliams
  • Patent number: 4983260
    Abstract: 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: Grant
    Filed: April 3, 1989
    Date of Patent: January 8, 1991
    Inventors: Henri Neel, Francis DeLannoy
  • Patent number: 4982021
    Abstract: 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: Grant
    Filed: June 8, 1988
    Date of Patent: January 1, 1991
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventors: Robert D. Best, Joseph A. Collier, Brian T. Keen, John H. Robson
  • Patent number: 4967018
    Abstract: 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: Grant
    Filed: October 18, 1989
    Date of Patent: October 30, 1990
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventors: Hwaili Soo, Bernard C. Ream, John H. Robson
  • Patent number: 4960754
    Abstract: 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: Grant
    Filed: December 8, 1989
    Date of Patent: October 2, 1990
    Assignee: 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
  • Patent number: 4937393
    Abstract: 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: Grant
    Filed: May 17, 1988
    Date of Patent: June 26, 1990
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Takayoshi Masuda, Katuyoshi Asano, Naomi Hori, Shinji Ando
  • Patent number: 4935554
    Abstract: 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: Grant
    Filed: July 17, 1989
    Date of Patent: June 19, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: Mark A. Murphy, Brad L. Smith, Adolfo' Aguilo', Kwoliang D. Tau
  • Patent number: 4873378
    Abstract: 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: Grant
    Filed: December 15, 1987
    Date of Patent: October 10, 1989
    Assignee: Hoechst Celanese Corporation
    Inventors: Mark A. Murphy, Brad L. Smith, Adolfo Aguilo', Kwoliang D. Tau
  • Patent number: 4873379
    Abstract: 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: Grant
    Filed: May 25, 1988
    Date of Patent: October 10, 1989
    Assignee: Hoechst Celanese Corporation
    Inventor: Mark A. Murphy
  • Patent number: 4870208
    Abstract: A process of preparing chiral alcohols by the asymmetric catalytic hydrogenolysis of epoxides using rhodium or ruthenium catalysts containing chiral phosphine ligands.
    Type: Grant
    Filed: June 3, 1988
    Date of Patent: September 26, 1989
    Assignee: Monsanto Company
    Inventors: Albert S. C. Chan, James P. Coleman, Grace M. Wagner
  • Patent number: 4831196
    Abstract: 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: Grant
    Filed: April 5, 1988
    Date of Patent: May 16, 1989
    Assignee: Chemrox, Inc.
    Inventors: Anthony J. Buonicore, Pankaj R. Desai
  • Patent number: 4822925
    Abstract: 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: Grant
    Filed: February 6, 1987
    Date of Patent: April 18, 1989
    Assignee: Union Carbide Corporation
    Inventors: John R. Briggs, John H. Robson
  • Patent number: 4822926
    Abstract: 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 se
    Type: Grant
    Filed: February 29, 1988
    Date of Patent: April 18, 1989
    Assignee: Shell Oil Company
    Inventor: Robert F. Dye
  • Patent number: 4812292
    Abstract: Chemical sterilants such as ethylene oxide are recovered from sterilization processes and converted into safer chemical compounds by non-catalytic hydrolysis.
    Type: Grant
    Filed: October 26, 1987
    Date of Patent: March 14, 1989
    Assignee: Joslyn Valve Corporation
    Inventor: Larry Joslyn
  • Patent number: 4801759
    Abstract: 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: Grant
    Filed: August 7, 1987
    Date of Patent: January 31, 1989
    Assignee: Degussa Aktiengesellschaft
    Inventors: Rainer Siegmeier, Gu Prescher, Helmut Maurer
  • Patent number: 4762954
    Abstract: 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: Grant
    Filed: August 7, 1987
    Date of Patent: August 9, 1988
    Assignee: Degussa Aktiengesellschaft
    Inventors: Rainer Siegmeier, Gunther Prescher, Helmut Maurer
  • Patent number: 4760200
    Abstract: 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: Grant
    Filed: December 31, 1985
    Date of Patent: July 26, 1988
    Assignee: Union Carbide Corporation
    Inventors: Brian T. Keen, John H. Robson, George E. Keller, II
  • Patent number: 4701571
    Abstract: 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: Grant
    Filed: June 30, 1986
    Date of Patent: October 20, 1987
    Assignee: Union Carbide Corporation
    Inventors: Hwaili Soo, John H. Robson
  • Patent number: 4626603
    Abstract: 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: Grant
    Filed: November 15, 1985
    Date of Patent: December 2, 1986
    Assignee: Degussa Aktiengesellschaft
    Inventors: Rainer Siegmeier, Gunter Prescher, Helmut Maurer
  • Patent number: 4605795
    Abstract: 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: Grant
    Filed: November 15, 1985
    Date of Patent: August 12, 1986
    Assignee: Degussa Aktiengesellschaft
    Inventors: Rainer Siegmeier, Gunter Prescher, Helmut Maurer, Gunter Hering
  • Patent number: 4599467
    Abstract: 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: Grant
    Filed: April 10, 1985
    Date of Patent: July 8, 1986
    Assignee: AKZO NV
    Inventors: Hilde Kersten, Gerhard Meyer
  • Patent number: 4579982
    Abstract: 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: Grant
    Filed: March 28, 1984
    Date of Patent: April 1, 1986
    Assignee: Union Carbide Corporation
    Inventors: John R. Briggs, John H. Robson
  • Patent number: 4579983
    Abstract: 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: Grant
    Filed: March 28, 1984
    Date of Patent: April 1, 1986
    Assignee: Union Carbide Corporation
    Inventor: Brian T. Keen
  • Patent number: 4578524
    Abstract: 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: Grant
    Filed: March 28, 1984
    Date of Patent: March 25, 1986
    Assignee: Union Carbide Corporation
    Inventor: Brian T. Keen
  • Patent number: 4571440
    Abstract: 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: Grant
    Filed: October 23, 1984
    Date of Patent: February 18, 1986
    Assignee: Union Carbide Corporation
    Inventors: Brian T. Keen, John H. Robson
  • Patent number: 4564715
    Abstract: 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: Grant
    Filed: October 23, 1984
    Date of Patent: January 14, 1986
    Assignee: Union Carbide Corporation
    Inventors: John R. Briggs, George L. O'Connor, John H. Robson
  • Patent number: 4560813
    Abstract: 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: Grant
    Filed: March 28, 1984
    Date of Patent: December 24, 1985
    Assignee: Union Carbide Corporation
    Inventor: Joseph A. Collier
  • Patent number: 4551566
    Abstract: 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: Grant
    Filed: September 8, 1983
    Date of Patent: November 5, 1985
    Assignee: Union Carbide Corporation
    Inventors: John H. Robson, George E. Keller, II
  • Patent number: 4504685
    Abstract: 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: Grant
    Filed: August 19, 1980
    Date of Patent: March 12, 1985
    Assignee: Varen Technology
    Inventor: Ronald J. Vaughan
  • Patent number: 4487854
    Abstract: 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: Grant
    Filed: December 27, 1983
    Date of Patent: December 11, 1984
    Assignee: BASF Wyandotte Corporation
    Inventor: Robert J. Hartman
  • Patent number: 4434105
    Abstract: 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: Grant
    Filed: June 27, 1980
    Date of Patent: February 28, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Josef Buysch, Heinrich Krimm, Hans Rudolph
  • Patent number: 4409403
    Abstract: 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: Grant
    Filed: September 28, 1981
    Date of Patent: October 11, 1983
    Assignee: Varen Technology
    Inventor: Ronald J. Vaughan
  • Patent number: 4393254
    Abstract: 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: Grant
    Filed: January 12, 1981
    Date of Patent: July 12, 1983
    Assignee: Texaco Inc.
    Inventors: Fred L. Johnson, Jr., Lewis W. Watts, Jr.
  • Patent number: 4390738
    Abstract: 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: Grant
    Filed: June 18, 1981
    Date of Patent: June 28, 1983
    Assignee: Imperial Chemical Industries PLC
    Inventors: Dhafir Y. Waddan, Derek Williams
  • Patent number: 4359589
    Abstract: 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: Grant
    Filed: July 27, 1981
    Date of Patent: November 16, 1982
    Assignee: Shell Oil Company
    Inventor: Thomas F. Brownscombe
  • Patent number: 4358625
    Abstract: 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: Grant
    Filed: March 9, 1979
    Date of Patent: November 9, 1982
    Assignee: Snamprogetti, S.p.A.
    Inventors: Alberto Paggini, Ugo Romano, Donato Furlone, Domenico Sanfilippo
  • Patent number: 4349417
    Abstract: 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: Grant
    Filed: January 9, 1981
    Date of Patent: September 14, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Siegfried Rebsdat, Sigmund Mayer, Josef Alfranseder, Iwo Schaffelhofer
  • Patent number: 4339616
    Abstract: 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: Grant
    Filed: September 15, 1980
    Date of Patent: July 13, 1982
    Assignees: Henkel Kommanditgesellschaft auf Aktien, Deutsche Gold-und Silberscheide Anstalt Vormals Roessler
    Inventors: Horst Rutzen, Wolfgang Rupilius
  • Patent number: 4307256
    Abstract: 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: Grant
    Filed: April 8, 1976
    Date of Patent: December 22, 1981
    Assignee: Anic S.p.A.
    Inventors: Gioacchino Cipriani, Carlo Neri, Ugo Romano
  • Patent number: 4277632
    Abstract: 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: Grant
    Filed: September 19, 1979
    Date of Patent: July 7, 1981
    Assignee: Nippon Shokubai Kaguku Kogyo Co., Ltd.
    Inventors: Toshihiko Kumazawa, Takeshi Yamamoto, Hiroshi Odanaka
  • Patent number: 4272455
    Abstract: 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: Grant
    Filed: December 26, 1979
    Date of Patent: June 9, 1981
    Assignee: The Dow Chemical Company
    Inventors: Frank T. Cook, Daniel W. Baugh, Jr., Robert V. Chambers, Jr.
  • Patent number: 4229378
    Abstract: 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: Grant
    Filed: May 14, 1979
    Date of Patent: October 21, 1980
    Assignee: Hooker Chemicals & Plastics Corp.
    Inventors: David Y. Tang, Arthur M. Foster
  • Patent number: 4165440
    Abstract: 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: Grant
    Filed: October 3, 1977
    Date of Patent: August 21, 1979
    Assignee: Shell Oil Company
    Inventor: Leo Kim
  • Patent number: 4160116
    Abstract: 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: Grant
    Filed: August 28, 1978
    Date of Patent: July 3, 1979
    Assignee: Showa Denko K.K.
    Inventors: Michihiro Mieno, Hideki Mori, Jun Nakanishi, Juichi Kasai
  • Patent number: 4141922
    Abstract: 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: Grant
    Filed: February 21, 1978
    Date of Patent: February 27, 1979
    Assignee: Continental Oil Company
    Inventor: Ronald J. Convers
  • Patent number: 4123444
    Abstract: 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: Grant
    Filed: June 13, 1977
    Date of Patent: October 31, 1978
    Assignee: General Electric Company
    Inventor: William E. Smith