Preparing By Hydroxylation At Point Of Ethylenic Unsaturation Patents (Class 568/860)
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Patent number: 4824969Abstract: A process for reacting in admixture, an olefin with oxygen, CO, and water, to form a cyclic alkylene carbonate, in the presence of a catalyst composition comprising a catalytically active osmium compound, copper containing co-catalyst I (e.g. CuBr.sub.2) and a co-catalyst II (e.g. pyridine) is disclosed.Type: GrantFiled: December 24, 1984Date of Patent: April 25, 1989Assignee: Exxon Research & Engineering Co.Inventors: Richard G. Austin, Robert C. Michaelson, Richard S. Myers
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Patent number: 4825004Abstract: A process for the production of alkane polyols and especially alkane triols where mono- and/or poly-epoxidized fatty acids and/or fatty acid esters and mixtures thereof, especially derivates of natural fatty acids, are reacted with short-chain alkane-carboxylic acids such as formic or acetic acids; and the ester alcohols produced are hydrogenated on a hydrogenation catalyst such as those containing copper chromite at elevated temperature and pressure. The maximum possible number of alcohols groups per molecule can be formed in this way thus producing alkane triols, for example, which are useful in cosmetic formulations as well as in polyurethanes.Type: GrantFiled: June 13, 1988Date of Patent: April 25, 1989Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Horst Rutzen, Gerhard Stoll
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Patent number: 4683347Abstract: The level of impurities such as glycerol-based acetals and/or ketals in glycerine, particularly glycerol-dimethylketal, is reduced by extraction of the glycerine with supercritical or near critical carbon dioxide.Type: GrantFiled: June 23, 1986Date of Patent: July 28, 1987Assignee: Shell Oil CompanyInventors: Zaida Diaz, James H. Miller
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Patent number: 4562299Abstract: A process for the preparation of water-soluble vicinal diols by means of a direct catalytic hydroxylation of the corresponding olefines with H.sub.2 O.sub.2. An olefine possibly carrying functional groups inert under the reaction conditions, and whose corresponding vicinal diol is soluble in water, is made to react, under vigorous stirring, with H.sub.2 O.sub.2 at a temperature between 0.degree. and 120.degree. C. and at a pressure between 1 and 100 atmospheres, in a two-phase aqueous liquid/organic liquid system consisting or consisting essentially of an acid aqueous phase containing H.sub.2 O.sub.2 and of an organic phase containing (1) said olefine; (2) possibly a solvent immiscible with the aqueous phase; and (3) a catalyst of the formula:Q.sub.3 XW.sub.4 O.sub.24-2nwherein Q represents an onium (RR.sub.1 R.sub.2 R.sub.3 M).sup.+ cation, wherein M is chosen from among N, P, As and Sb, and R, R.sub.1, R.sub.2 and R.sub.Type: GrantFiled: December 12, 1984Date of Patent: December 31, 1985Assignee: Montedison S.p.A.Inventors: Carlo Venturello, Mario Gambaro
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Patent number: 4533772Abstract: The process for hydroxylating olefins with oxygen in the presence of water, an osmium-halide (e.g., OsBr.sub.3) catalyst and transition metal containing co-catalyst (CuBr.sub.2) is disclosed.Type: GrantFiled: August 29, 1983Date of Patent: August 6, 1985Assignee: Exxon Research & Engineering Co.Inventors: Robert C. Michaelson, Richard G. Austin
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Patent number: 4533773Abstract: A process for hydroxylating olefins, such as ethylene or propylene, using an osmium oxide catalyst such as OsO.sub.4, a carboxylate salt co-catalyst, such as sodium acetate, and organic hydroperoxide oxidant is disclosed.Type: GrantFiled: March 22, 1984Date of Patent: August 6, 1985Assignee: Exxon Research & Engineering Co.Inventors: Robert C. Michaelson, Richard G. Austin
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Patent number: 4496779Abstract: A process directed to the hydroxylation of olefins by reacting said olefins in the presence of oxygen, water, and a catalyst composition comprising (i) a catalytically active osmium containing compound, (ii) a Co-catalyst I comprising a copper containing compound such as CuBr.sub.2, and (iii) a Co-catalyst II capable of increasing the rate and/or selectivity of the hydroxylation reaction, such as 1,4-diazabicyclo [2.2.2.] octane is disclosed.Type: GrantFiled: April 26, 1984Date of Patent: January 29, 1985Assignee: Exxon Research & Engineering Co.Inventors: Richard S. Myers, Robert C. Michaelson, Richard G. Austin
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Patent number: 4496778Abstract: A process directed to the hydroxylation of olefins by reacting said olefins in the presence of oxygen, water, and a catalyst composition comprising (i) a catalytically active osmium containing compound, (ii) a Co-catalyst I comprising a copper containing compound such as CuBr.sub.2, and (iii) a Co-catalyst II capable of increasing the rate and/or selectivity of the hydroxylation reaction, such as pyridine is disclosed.Type: GrantFiled: October 3, 1983Date of Patent: January 29, 1985Assignee: Exxon Research & Engineering Co.Inventors: Richard S. Myers, Robert C. Michaelson, Richard G. Austin
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Patent number: 4486613Abstract: A process for hydroxylating olefins, such as ethylene or propylene, using an oxidant selected from organic hydroperoxides, H.sub.2 O.sub.2, and oxygen and a catalyst composition comprising at least one osmium carbonyl catalyst, such as Os.sub.3 (CO).sub.12, and optionally at least one cocatalyst such as NaI, is disclosed.Type: GrantFiled: September 20, 1982Date of Patent: December 4, 1984Assignee: Exxon Research & Engineering Co.Inventors: Robert C. Michaelson, Richard G. Austin, Donald A. White
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Patent number: 4482763Abstract: A process for hydroxylating olefins with an organic hydroperoxide and water in the presence of an osmium containing catalyst (e.g. OsO.sub.4) and an organic halogenated hydrocarbon co-catalyst (e.g., n-butyl iodide) is disclosed.Type: GrantFiled: July 19, 1982Date of Patent: November 13, 1984Assignee: Exxon Research & Engineering Co.Inventors: Richard G. Austin, Robert C. Michaelson
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Patent number: 4413151Abstract: A process for hydroxylating olefins using a supported osmium catalyst such as Os.sub.3 (CO).sub.12 adsorbed on a support, such as MgO, and optionally in conjunction with a co-catalyst such as NaI, is disclosed.Type: GrantFiled: July 14, 1982Date of Patent: November 1, 1983Assignee: Exxon Research & Engineering Co.Inventors: Robert C. Michaelson, Richard G. Austin, Donald A. White
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Patent number: 4410743Abstract: 2,3-Dimethylbutane-2,3-diol is prepared by a process in which 2,3-dimethylbutenes are reacted with oxygen or an oxygen-containing gas, in the presence of 0.01 to 20 parts by weight of water (relative to 2,3-dimethylbutenes employed), at temperatures of from 40.degree. to 180.degree. C. and residence times of 5 to 150 minutes, without the addition of catalysts.Type: GrantFiled: April 1, 1982Date of Patent: October 18, 1983Assignee: Bayer AktiengesellschaftInventors: Klaus G. Wilms, Helmut Waldmann, Johann Grolig
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Patent number: 4393253Abstract: A method for preparing polyols such as diols by catalytic hydroxylation of an olefinic compound by reacting the olefinic compound with an organic hydroperoxide and water in the presence of a catalyst comprising osmium compound and a specific halide co-catalyst is disclosed.Type: GrantFiled: October 9, 1981Date of Patent: July 12, 1983Assignee: Exxon Research & Engineering Co.Inventors: Robert C. Michaelson, Richard G. Austin
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Patent number: 4390739Abstract: A process directed to the hydroxylation of olefins by reacting said olefins with an oxygen containing gas and water in the presence of a catalyst composition comprising (i) a catalytically active metal oxide such as OsO.sub.4, (ii) as a co-catalyst I a transition metal salt such as CuBr.sub.2, and (iii) optionally a co-catalyst II salt such as tetra ethyl ammonium bromide is disclosed.Type: GrantFiled: October 9, 1981Date of Patent: June 28, 1983Assignee: Exxon Research & Engineering Co.Inventors: Robert C. Michaelson, Richard G. Austin
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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: 4387255Abstract: Process for production of ethylene glycol comprising contacting a nonflammable feed comprising ethylene, molecular oxygen and water with a catalyst comprising iodine under reaction conditions in a reaction zone in which there is maintained a partial pressure of ethylene that is effective to yield ethylene glycol without substantial acetaldehyde generation. In a preferred embodiment, ethylene glycol is removed from the reaction zone at a rate effective to minimize formation of condensed glycol by-products.Type: GrantFiled: September 25, 1981Date of Patent: June 7, 1983Assignee: Standard Oil Company (Indiana)Inventor: George R. Wood
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Patent number: 4324909Abstract: In the process for catalytically reacting olefin and oxygen to provide glycol or a mixture of glycol and glycol ester, higher rates of reaction and/or higher selectivities for the desired product(s) are obtained employing as catalyst, a composition comprising a mixture of molecular iodine and hydrobromic acid; hydriodic acid and hydrobromic acid; or, at least one oxide of antimony, bismuth or tellurium in admixture with at least one member of the group consisting of hydriodic acid; molecular iodine; hydriodic acid and molecular iodine; molecular iodine and hydrobromic acid; and, hydriodic acid and hydrobromic acid in a water or water-carboxylic acid reaction medium.Type: GrantFiled: July 17, 1980Date of Patent: April 13, 1982Assignee: National Distillers & Chemical Corp.Inventors: David Horvitz, Thomas S. Brima
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Patent number: 4314088Abstract: Method for preparing polyols such as diols and triols by the homogeneous catalytic hydroxylation of an olefinic compound by contacting the olefinic compound with an organic hydroperoxide in an inert polar solvent containing catalytic amounts of an osmium compound and a halide and at least a stoichiometric amount of water based on the amount of said olefinic compound.Type: GrantFiled: November 24, 1980Date of Patent: February 2, 1982Assignee: Exxon Research & Engineering Co.Inventors: Richard G. Austin, Robert C. Michaelson
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Patent number: 4308409Abstract: Propylene is converted to propylene glycol at high selectivity in a process in which ethylbenzene hydroperoxide and water are reacted with propylene in the presence of osmium tetroxide catalyst and a base at a pH of about 14.Type: GrantFiled: July 28, 1980Date of Patent: December 29, 1981Assignee: Gulf Research & Development CompanyInventors: Ching-Yong Wu, Thaddeus P. Kobylinski, John E. Bozik
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Patent number: 4293717Abstract: Aldehydes and diols are prepared by reacting an olefine with hydrogen peroxide in the presence of a Group Va or VIa metal compound, such as molybdenum-(III)-acetylacetonate.Type: GrantFiled: February 5, 1979Date of Patent: October 6, 1981Assignee: Bayer AktiengesellschaftInventors: Helmut Waldmann, Wulf Schwerdtel, Wolfgang Swodenk
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Patent number: 4280924Abstract: A catalyst residue containing osmium catalyst having a substantial component with a valency state less than +5 is regenerated to a valency state greater than +5 by contacting the residue with an organic hydroperoxide at a pH greater than 7 and the regenerated catalyst residue is recycled to a hydroxylation reactor containing ethylene or propylene, a polar organic solvent, an aqueous solution of cesium, rubidium, potassium or tetraalkylammonium hydroxide and an organic hydroperoxide.Type: GrantFiled: December 28, 1979Date of Patent: July 28, 1981Assignee: Gulf Research & Development CompanyInventors: Ching-Yong Wu, Thaddeus P. Kobylinski
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Patent number: 4278517Abstract: A process for producing glycols by the catalytic oxidation of olefinic compounds which comprises contacting an olefinic compound with an organic selenoxide in an aqueous alkaline medium in the presence of a catalytic amount of octavalent osmium to form the corresponding glycol.Type: GrantFiled: June 26, 1980Date of Patent: July 14, 1981Assignee: Union Carbide CorporationInventor: Anthony G. Abatjoglou
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Patent number: 4255596Abstract: Ethylene is converted to ethylene glycol at high selectivity in a process in which ethylbenzene hydroperoxide and water are reacted with ethylene in the presence of osmium tetroxide catalyst and a base at a pH of about 14.Type: GrantFiled: February 25, 1980Date of Patent: March 10, 1981Assignee: Gulf Research & Development CompanyInventors: Ching-Yong Wu, Thaddeus P. Kobylinski, John E. Bozik
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Patent number: 4229601Abstract: Ethylene or propylene is converted to the corresponding glycol at high selectivity in a process in which t.butyl hydroperoxide is reacted with the olefin in a two-phase liquid, organic-aqueous reaction system in the presence of osmium tetroxide and cesium, rubidium or potassium hydroxide.Type: GrantFiled: December 26, 1978Date of Patent: October 21, 1980Assignee: Gulf Research & Development CompanyInventors: Ching-Yong Wu, Thaddeus P. Kobylinski
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Patent number: 4217291Abstract: Osmium (III) or (IV) in an anionic complex with oxygen and having an alkali metal, ammonium or tetra(lower)alkylammonium cation is oxidized to a valency state higher than 5 by reaction with an organic hydroperoxide, such as ethylbenzene hydroperoxide, at a temperature less than 30.degree. C.Type: GrantFiled: December 26, 1978Date of Patent: August 12, 1980Assignee: Gulf Research & Development CompanyInventors: Ching-Yong Wu, Thaddeus P. Kobylinski
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Patent number: 4209650Abstract: Ethylene glycol is prepared by the reaction of ethylene, molecular oxygen and water in the presence of an iodine catalyst and in the presence of a copper co-catalyst or promoter.Type: GrantFiled: May 28, 1976Date of Patent: June 24, 1980Assignee: Halcon International, Inc.Inventors: Olav T. Onsager, Peter L. Szecsi
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Patent number: 4203926Abstract: Ethylbenzene hydroperoxide and ethylene or propylene are converted to acetophenone, 1-phenylethanol and the corresponding glycol at high selectivity in a process in which ethylbenzene hydroperoxide is reacted with the olefin in a two-phase liquid, organic-aqueous reaction system in the presence of osmium tetroxide and cesium, rubidium or potassium hydroxide.Type: GrantFiled: December 18, 1978Date of Patent: May 20, 1980Assignee: Gulf Research & Development CompanyInventors: Ching-Yong Wu, Thaddeus P. Kobylinski
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Patent number: 4202995Abstract: A glycol is produced by reacting an olefine with oxygen in an aqueous solution which comprises copper or iron ions, bromide ions, and iodide ions. The catalyst may be recycled to the reaction in the heavy ends of the process.Type: GrantFiled: March 27, 1979Date of Patent: May 13, 1980Assignee: Imperial Chemical Industries LimitedInventor: Alec Mee
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Patent number: 4200766Abstract: An improved process for the preparation of hydroxycitronellol by an addition reaction of water with citronellol. This reaction takes place directly on heating a homogeneous solution of citronellol in a mixture of water and an .alpha.-methyl-branched lower alkanol in the presence of a strongly acid ion exchanger.Hydroxycitronellol may be used as a fragrance material and is an important intermediate for the preparation of the highly desired scent hydroxycitronellal.Type: GrantFiled: November 17, 1978Date of Patent: April 29, 1980Assignee: BASF AktiengesellschaftInventor: Werner Hoffmann
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Patent number: 4195190Abstract: Ethylene glycol is produced by the liquid phase reaction of ethylene, oxygen and water in the presence of a catalyst comprising iodine or an iodine-containing compound and bromine or a bromine-containing compound.Type: GrantFiled: April 3, 1978Date of Patent: March 25, 1980Assignee: PPG Industries, Inc.Inventors: Thomas R. Bierschenk, Rowland Pettit, Donald R. Nielsen
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Patent number: 4191696Abstract: A new liquid phase oxidation process in which a metal nitro complex transfers an oxygen atom from the nitro ligand to a substrate; especially such process conducted cyclically or catalytically using molecular oxygen as the oxygen source. Metal nitrosyl complex is formed as a coproduct together with an oxidation product of the substrate. In a catalytic process, molecular oxygen maintains a concentration of nitro ligand in the reaction mixture. In a cyclic process, nitrosyl ligand of the metal nitrosyl coproduct is reoxidized by molecular oxygen in presence of a monodentate base such as pyridine to nitro ligand; and the nitro complex, thus regenerated, can be used again to oxidize the substrate, In particular the metal is a Group VIII metal, especially cobalt and the nitro complex is pyridine cobalt nitro saloph. To accelerate oxidation of the substrate at given temperature, a cocatalyst is included in the reaction mixture, e.g.Type: GrantFiled: July 24, 1978Date of Patent: March 4, 1980Assignee: Allied Chemical CorporationInventors: Benjamin S. Tovrog, Steven E. Diamond, Frank Mares
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Patent number: 4171313Abstract: A catalytic system for oxidation of organic compounds including olefins, cyclic ketones and secondary alcohols. Soluble peroxo or solid supported oxo or peroxo complexes of molybdenum or tungsten are used in the presence of hydrogen peroxide to effect the oxidation. The resulting products include lactones, hydroxy acids, ketoacids, hydroxy esters and ketoesters from cyclic ketones; ketones from secondary alcohols and polyols or derivatives thereof from allylic alcohols.Type: GrantFiled: October 14, 1977Date of Patent: October 16, 1979Assignee: Allied Chemical CorporationInventors: Frank Mares, Stephen E. Jacobson, Reginald T. Tang