Of Aldehyde Or Ketone Patents (Class 568/862)
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Patent number: 5235118Abstract: Disclosed is a continuous process for the manufacture of 2-ethyl-2-(hydroxymethyl)hexanal wherein 2-ethylhexanal, formaldehyde and a tertiary amine are continuously fed to a reaction zone and crude product comprising an aqueous phase and an organic phase containing 2-ethyl-2-(hydroxymethyl)hexanal and 2-ethylhexanal is continuously removed from the reaction zone Also disclosed are processes for (1) the azeotropic distillation of the organic phase of the crude product whereby unreacted 2-ethylhexanal is recovered and (2) the catalytic hydrogenation of the refined, organic phase of the crude product to produce 2-butyl-2-ethyl-1,3-propanediol.Type: GrantFiled: August 31, 1992Date of Patent: August 10, 1993Assignee: Eastman Kodak CompanyInventors: Don L. Morris, William A. Beavers, William E. Choate
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Patent number: 5220020Abstract: A process is provided whereby organic carbonyl substrates, including esters, lactones, ketones, amides and imides are reduced in a reaction with a silane reducing reagent and a catalyst. Exemplary catalysts include metal alkoxides and metal aryloxides.Type: GrantFiled: November 14, 1991Date of Patent: June 15, 1993Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Alberto Gutierrez, Scott C. Berk, Kristina A. Kreutzer
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Patent number: 5210337Abstract: Rhenium has been found to be formaldehyde resistant catalyst and is thus useful in the catalytic hydrogenation of carbonyls, acetals and esters to alcohols when the reaction medium contains formaldehyde as a reactant or impurity. Also, rhenium is a useful catalyst in the hydrogenolysis of acylic acetals to alcohols.Type: GrantFiled: March 28, 1990Date of Patent: May 11, 1993Assignee: Hoechst Celanese CorporationInventor: Jerry A. Broussard
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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
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Patent number: 5171898Abstract: The hydration of acrolein in the presence of a chelate-forming ion exchange resin based on polystyrene/divinyl benzene as catalyst and on the subsequent hydrogenation of the reaction mixture freed of the non-reacted acrolein and containing 3-hydroxypropionaldehyde is disclosed. As a result of using chelate-forming ion exchangers with anchor groups of the formula ##STR1## in which Z=H, C.sub.1 -C.sub.6 -alkyl, --CH.sub.2 --CH(CH.sub.3)--Y' or --(CH.sub.2).sub.o --Y' and Y and/or Y'=--COOH, --OH, pyridyl or --P(O)(CH.sub.2 OH)OH, the hydration occurs at lower temperatures with a greater space-time yield and especially a greater selectivity than when using previously known ion exchangers. Resins with methylene imino diacetic acid anchor groups in the H form or partially doped with alkali-, alkaline-earth or earth-metal ions are especially suitable.Type: GrantFiled: November 27, 1991Date of Patent: December 15, 1992Assignee: Degussa AktiengesellschaftInventors: Dietrich Arntz, Norbert Wiegand
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Patent number: 5166370Abstract: A process for producing tetrahydrofuran, 1,4-butanediol, and 2-methyl-1,3,-propanediol is disclosed. A mixture containing 4-hydroxybutanal and 3-hydroxy-2-methylpropanal is hydrogenated in the presence of a transition metal supported on a weakly acidic ion-exchange resin or zeolite-type material to give tetrahydrofuran as the major product, and 1,4-butanediol and 2-methyl-1,3-propanediol as minor products. High yields of 2-methyl-1,3-propanediol can be obtained.Type: GrantFiled: April 12, 1991Date of Patent: November 24, 1992Assignee: Arco Chemical Technology, L.P.Inventors: Frank J. Liotta, Jr., Haven S. Kesling, Jr., Rangasamy Pitchai
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Patent number: 5162517Abstract: The sugar alcohols given in the title can be prepared in epimer-free form from the corresponding sugars by catalytic hydrogenation in aqueous solution using hydrogen, the hydrogenation being carried out continuously at 100-500 bar of H.sub.2 and 60.degree.-125.degree. C. on a fixed bed of carrier-free mouldings composed of pressed powders of the elements of the iron group of the periodic table. The mouldings have a compressive strength of above 50 N and an internal surface of 10-90 m.sup.2 /g.Type: GrantFiled: September 20, 1990Date of Patent: November 10, 1992Assignee: Bayer AktiengesellschaftInventor: Gerhard Darsow
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Patent number: 5149889Abstract: A process is disclosed for the preparation of tertiary alcohols, alpha-alkyl substituted nitriles, alkyl-substituted imines or tertiary amines by alkylation of a starting material that is a carbonyl compound or a nitrile followed by hydrolysis wherein the alkylation is carried out with the aid of a reaction system formed by suspending a mixture of:substantially 15 to 25% by weight of methyllithium or ethyllithium;substantially 35 to 45% by weight of an inorganic compound selected from the group which consists of at least one metal oxide selected from the group which consists of SiO.sub.2, Al.sub.2 O.sub.3, and CaO, and synthetic anhydrous aluminum silicate; andsubstantially 35 to 45% by weight of a paraffin oil or wax; in an organic solvent selected from the group which consists of:C.sub.5 to C.sub.10 saturated aliphatic hydrocarbons, C.sub.5 to C.sub.Type: GrantFiled: October 30, 1990Date of Patent: September 22, 1992Assignee: Metallgesellschaft AktiengesellschaftInventors: Jurgen Deberitz, Wilfried Weiss
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Patent number: 5093537Abstract: 1,3-Propanediol is manufactured by the hydration of acrolein in an aqueous solution over a fully hydrated, alumina-bound zeolite with a pore size >5 angstroms to form 3-hydroxypropanal and hydrogenation of the 3-hydroxypropanal typically in an aqueous solution in the presence of a nickel catalyst.Type: GrantFiled: July 24, 1991Date of Patent: March 3, 1992Assignee: Hoechst Celanese CorporationInventors: Jerry D. Unruh, Debra A. Ryan, Ioan Nicolau
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Patent number: 5091559Abstract: A process is disclosed for forming alkyl 4-oxobutyrates and its acetals which comprises reacting under anhydrous conditions acrolein or its acetals with carbon monoxide and an alcohol of the formula R OH wherein R is lower alkyl in the presence of a catalytically effective amount of a catalyst comprising palladium metal which is either unsupported or supported on an inert carrier and a promoting effective amount of hydrogen halide. An intermediate in the process, i.e., .beta.-halopropionaldehyde or acetal thereof can also be used in forming alkyl 4-oxobutyrates and acetals thereof by reacting under anhydrous conditions said .beta.-halopropionaldehyde or its acetals with carbon monoxide and an alcohol of the formula ROH wherein R is lower alkyl in the presence of a catalytically effective amount of a catalyst comprising palladium metal which is either unsupported or supported on an inert carrier.Type: GrantFiled: February 8, 1988Date of Patent: February 25, 1992Assignee: Quantum Chemical CorporationInventors: Jawad H. Murib, William D. Baugh
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Patent number: 5015786Abstract: In a first form, a process is provided for preparing phenol by converting acetone by-produced by the cumene process into isopropanol, and alkylating benzene with the isopropanol and optional propylene, thereby forming phenol without acetone by-product. And cumene is prepared by alkylating benzene in the presence of a zeolite catalyst using isopropanol or a mixture of isopropanol and propylene as an alkylating agent. Further provided is the continuous alkylation of benzene with isopropanol wherein a reaction mixture is divided into first and second portions, with the first portion being recycled to the reactor and the second portion being taken out as a reaction product.Type: GrantFiled: November 27, 1989Date of Patent: May 14, 1991Assignee: Mitsui Petrochemical Industries Inc.Inventors: Shintaro Araki, Fujihisa Matsunaga, Hiroshi Fukuhara
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Patent number: 5015789Abstract: A method for preparing 1,3-propanediol is disclosed which comprises the hydration of acrolein in the presence of an acidic cation exchanger resin and the hydrogenation of the 3-hydroxypropionaldehyde obtained in the first stage. The volume-time yield was able to be increased in the hydration stage by using a cation exchanger resin with phosphonic acid groups, preferably a cation exchanger with chelating aminophosphonic acid groups. The hydrogenation catalyst can be repeatedly reused without appreciable loss of activity.Type: GrantFiled: August 3, 1990Date of Patent: May 14, 1991Assignee: Degussa AktiengesellschaftInventors: Dietrich Arntz, Norbert Wiegand
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Patent number: 5008408Abstract: Mixtures which contain 1,4-butanediol and tetrahydrofuran are prepared by heating 4-hydroxybutyraldehyde of the formula ##STR1## at 20.degree.-300.degree. C. in the presence or absence of 1,4-butanediol and subjecting the resulting acetals of the formulae ##STR2## to a catalytic hydrogenation at 50.degree.-300.degree. C. and 1-350 bar.Type: GrantFiled: March 7, 1990Date of Patent: April 16, 1991Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Juergen Frank, Franz Merger, Hans-Juergen Weyer
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Patent number: 4973768Abstract: Unsaturated alcohols are prepared by hydrogenation of the corresponding carbonyl compounds in the presence of a platinum-cobalt bi-metallic catalyst having an alloy structure.Type: GrantFiled: March 6, 1989Date of Patent: November 27, 1990Assignee: Rhone-Poulenc SanteInventors: Georges Cordier, Pierre Fouilloux, Jean-Michel Grosselin
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Patent number: 4933473Abstract: A process for production of neopentyl glycol by hydrogenation of hydroxypivaldehyde in the presence of a Pt-Ru-W catalyst. This catalyst exhibits high activity and selectivity, and further has a long life. Neopentyl glycol is an important intermediate for use in production of a wide variety of chemicals.Type: GrantFiled: April 21, 1989Date of Patent: June 12, 1990Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Teruyuki Ninomiya, Tomiyoshi Furuta, Seiji Kita, Yoshimi Fujii
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Patent number: 4929776Abstract: Unsaturated alcohols are prepared by hydrogenation of the corresponding unsaturated carbonyl compounds in a homogeneous medium and in the presence of a ruthenium-based catalyst.Type: GrantFiled: November 29, 1988Date of Patent: May 29, 1990Assignee: Rhone-Poulenc SanteInventors: Jean-Michel Grosselin, Claude Mercier
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Patent number: 4929777Abstract: Disclosed are catalyst compositions comprised of chemically-mixed, copper-titanium oxides and the use of such catalyst compositions in the hydrogenation of certain esters to obtain the alcohol corresponding to the acid residue of the ester.Type: GrantFiled: February 13, 1989Date of Patent: May 29, 1990Assignee: Eastman Kodak CompanyInventors: Gether Irick, Jr., Patricia N. Mercer, Kenneth E. Simmons
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Patent number: 4929773Abstract: A method is provided for the production of 1-(4'-isobutylphenyl)ethanol (IBPE) comprising hydrogenating 4-isobutylacetophenone (IBAP) in the absence of a solvent using as a catalyst a treated activated sponge nickel catalyst, e.g., Raney nickel, obtained by subjecting such a catalyst wetted with a protective liquid composed preponderantly of water to a washing treatment with an organic washing liquid in which the aqueous protective liquid is substantially soluble and which is substantially soluble in IBAP or IBPE, e.g., a lower alkanol such as methanol, ethanol or isopropanol. The catalyst optionally may also be washed with IBAP or IBPE after the wash with the organic washing liquid and before being used in the hydrogenation reaction. The washing treatment results in substantially higher conversions IBAP and increased yields of IBPE with a practical reaction time.Type: GrantFiled: September 7, 1988Date of Patent: May 29, 1990Assignee: Hoechst Celanese CorporationInventor: Debra A. Ryan
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Patent number: 4925990Abstract: Unsaturated alcohols are prepared by the hydrogenation of an unsaturated carbonyl compound in a two-phase liquid medium and in the presence of a catalyst consisting of a ruthenium derivative associated with a water-soluble ligand or a complex of ruthenium with a water-soluble ligand.Type: GrantFiled: November 29, 1988Date of Patent: May 15, 1990Assignee: Rhone-Poulenc SanteInventors: Jean-Michel Grosselin, Claude Mercier
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Patent number: 4922032Abstract: Disclosed is the preparation of both optically active stereoisomers of 2-methyl-1,2-hexanediol, which are useful intermediates for the syntheses of several prostaglandins for peptic ulcer therapy.Type: GrantFiled: April 26, 1989Date of Patent: May 1, 1990Assignee: Centro De Investigacion Y De Estudios Avanzados Del Instituto Politecnico NacionalInventors: Pedro Joseph-Nathan, Humberto Cervantes-Cuevas
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Patent number: 4916252Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a 1,3-diketone in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.Type: GrantFiled: June 16, 1988Date of Patent: April 10, 1990Assignee: Takasago International CorporationInventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
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Patent number: 4912265Abstract: A process for the reduction of carbonyl compounds by an alkali or alkaline-earth metal borohydride in the presence of a phase transfer catalyst which is an N-benzyl-N,N-bis (2-hydroxyethyl)cocoammonium halide.Type: GrantFiled: August 26, 1988Date of Patent: March 27, 1990Assignee: Akzo America Inc.Inventor: Ralph Franklin
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Patent number: 4906795Abstract: Vitamin A containing practically no 2-cis or 6-cis isomer is prepared by hydrogenation of the aldehyde of vitamin A, optionally in the form of a complex with hydroquinone, in the presence of a ruthenium hydride catalyst.Type: GrantFiled: November 29, 1988Date of Patent: March 6, 1990Assignee: Rhone-Poulenc SanteInventors: Jean-Michel Grosselin, Claude Mercier
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Patent number: 4879420Abstract: Process for preparing 2-alkyl-1,4-butanediols and mixtures with 1,4-butanediol which comprises bringing together, at an initial alkaline pH, and at a temperature and pressure suitable for reaction, a mixture of 4-hydroxybutyraldehyde and/or its cyclic acetal, 2-hydroxytetrahydrofuran, hydrogen, an unsubstituted aliphatic aldehyde, especially formaldehyde, and a hydrogenation catalyst. Also processes for preparing mixtures of tetrahydrofuran and 3-alkyltetrahydrofuran from the diol mixtures, and copolymers from the tetrahydrofuran mixtures.Type: GrantFiled: May 6, 1988Date of Patent: November 7, 1989Assignee: E.I. du Pont de Nemours and CompanyInventor: Richard E. Ernst
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Patent number: 4877909Abstract: A process for reducing an aldehyde or ketone in the presence of a stable, highly active catalyst which is insoluble in a solvent and which can be recovered easily from the reaction system after completion of the reaction and used repeatedly, characterized in that an aldehyde or ketone having a carbonyl group is reacted with an alcohol in the presence of hydrous zirconium oxide as the catalyst.Type: GrantFiled: February 22, 1988Date of Patent: October 31, 1989Assignee: Japan Tobacco, Inc.Inventors: Sigenobu Mizusaki, Hajime Matsushita, Shigeo Ishiguro, Hiroshi Ichinose, Akira Izumi
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Patent number: 4861922Abstract: There is disclosed a method of hydroformylating 3-methyl-3-buten-1-ol and analogs thereof with carbon monoxide and hydrogen in the presence of a rhodium compound free from modification by a ligand containing an element belonging to the group V of the periodic table as well as a method of producing 3-methylpentane-1,5-diol and .beta.-methyl-.delta.-valerolactone using such hydroformylation product.Type: GrantFiled: February 11, 1987Date of Patent: August 29, 1989Assignee: Kuraray Company, Ltd.Inventors: Yasuo Tokitoh, Noriaki Yoshimura
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Patent number: 4859801Abstract: Process for preparing 2-alkyl-1,4-butanediols and mixtures with 1,4-butanediol which comprises bringing together, at an initial alkaline pH, and at a temperature and pressure suitable for reaction, 2,3-dihydrofuran, hydrogen, an unsubstituted aliphatic aldehyde, especially formaldehyde, and a hydrogenation catalyst. Also processes for preparing mixtures of tetrahydrofuran and 3-alkyltetrahydrofuran from the diol mixtures, and copolymers from the tetrahydrofuran mixtures.Type: GrantFiled: May 26, 1988Date of Patent: August 22, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventor: Richard E. Ernst
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Patent number: 4855515Abstract: A method for producing neopentyl glycol is described using tertiaryamines as a catalyst for the condensation of isobutyraldehyde and formaldehyde followed by hydrogenation of the resulting reaction mixture using a manganese oxide promoted copper chromite catalyst.Type: GrantFiled: August 12, 1987Date of Patent: August 8, 1989Assignee: Eastman Kodak CompanyInventors: Don L. Morris, Billy W. Palmer, Thomas W. McAninch
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Patent number: 4837367Abstract: Process for the hydrogenation of carbonyl-containing compounds at mild conditions of temperature and pressure to produce alcohols or amines is disclosed, employing palladium on zinc oxide catalysts. A method for the preparation of the palladium on zinc oxide catalysts useful for the desired reductive conversion is also disclosed.Type: GrantFiled: August 3, 1987Date of Patent: June 6, 1989Assignee: Eastman Kodak CompanyInventors: Bruce L. Gustafson, Paul S. Wehner, Gregory O. Nelson, Patricia N. Mercer
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Patent number: 4783559Abstract: Disclosed is a process of reduction of aldehydes or ketones by means of reaction with alcohols, in the presence of a catalyst, to produce alcohols which correspond to said respective aldehyde or ketone. A solid of partially dehydrated one or more metal hydroxides whose metal is selected from the group consists of titanium, tin, ion, aluminium, cerium, and niobium is used as the catalyst. This process can be conducted either in a gas phase or in a liquid phase.Type: GrantFiled: March 25, 1987Date of Patent: November 8, 1988Assignee: Japan Tobacco Inc.Inventors: Hajime Matsushita, Kyoko Takahashi, Makoto Shibagaki
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Patent number: 4777302Abstract: A method for hydrogenating an aldehyde and/or a ketone in the presence of a ruthenium catalyst, wherein said ruthenium catalyst is obtained by reducing an alkali metal ruthenate with a reducing agent selected from the group consisting of methanol, formaldehyde and formic acid.Type: GrantFiled: July 30, 1987Date of Patent: October 11, 1988Assignee: Mitsubishi Chemical Industries LimitedInventors: Junzo Haji, Ichiro Yokotake, Nobuyuki Murai, Toshihiro Kawakami
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Patent number: 4756840Abstract: Described is the novel compound genus, the beta-alkylidene phenethyl alcohols of our invention, defined according to the generic structure: ##STR1## (wherein R.sub.1 represents hydrogen or methyl, useful in augmenting or enhancing the aroma of consumable materials including perfumes, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener articles, fabric softener compositions, cosmetic powders and hair preparations).Type: GrantFiled: September 3, 1987Date of Patent: July 12, 1988Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Robert P. Belko
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Patent number: 4728671Abstract: The present invention relates to a process for producing alcohols comprising hydrogenating compounds selected from the group consisting of acids, esters and aldehydes under sufficient hydrogen pressure and temperature in the presence of a catalyst comprising a copper chromite first component and a second component consisting essentially of copper deposited on a support.Type: GrantFiled: April 25, 1985Date of Patent: March 1, 1988Assignee: Oleofina, S.A.Inventor: Herve Hinnekens
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Patent number: 4723047Abstract: The present invention relates to a process for the preparation of nonadecanediols by the hydroformylation of oleyl alcohol. Rhodium and salts of sulfonated or carboxylated triarylphosphines, which are soluble in organic media and insoluble in water, are used as hydroformylation catalysts. The hydroformylation product is then treated with a diluted solution of a base dissolved in water, the aqueous phase separated and the hydroformylation product treated with hydrogen at elevated temperature in the presence of a hydrogenation catalyst.Type: GrantFiled: September 23, 1986Date of Patent: February 2, 1988Assignee: Ruhrchemie AktiengesellschaftInventors: Helmut Bahrmann, Boy Cornils, Werner Konkol, Jurgen Weber, Ludger Bexten, Hanswilhelm Bach
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Patent number: 4496781Abstract: A process for the preparation and purification of a glycol aldehyde intermediate which is later hydrogenated to ethylene glycol is disclosed. The process proceeds via the catalytic reaction of formaldehyde, carbon monoxide and hydrogen and utilizes a novel class of lipophilic rhodium phosphine amide catalysts and an effective solvent mixture, which enables efficient catalyst separation and recycle without the loss of a substantial amount of the expensive catalyst.Type: GrantFiled: April 5, 1984Date of Patent: January 29, 1985Assignee: The Halcon SD Group, Inc.Inventors: Stephen E. Jacobson, Chun F. Chueh
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Patent number: 4465873Abstract: A process is disclosed for obtaining butanediols by distilling the same from an aqueous solution obtained by hydrogenation, carried out in the presence of a nickel catalyst, of a hydroformylated allyl alcohol. The invention process is characterized in that 2-methyl-1,3-propanediol, 1,4-butanediol and a high-boiling fraction are separated by distillation from a butanediol mixture obtained using the following steps:(1) the aqueous solution is treated such that the pH of the aqueous solution is adjusted to 8.5 or above, and precipitates thus formed are removed;(2) the aqueous solution is treated such that residual 4-hydroxybutyraldehyde and water are distilled off at a temperature of up to 100.degree. C.; and(3) the resulting mixture is heated at a temperature of up to 180.degree. C. to obtain a distillate consisting of 2-methyl-1,3-propanediol and 1,4-butanediol, free of the high-boiling fraction.Type: GrantFiled: July 6, 1983Date of Patent: August 14, 1984Assignees: Daicel Chemical Industried, Ltd., Kuraray Co., Ltd.Inventor: Yoshiyuki Harano
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Patent number: 4405821Abstract: In the process for producing glycolaldehyde and/or ethylene glycol by the reaction of formaldehyde, carbon monoxide and hydrogen in a non-amide solvent at elevated temperature and superatmospheric pressure in the presence of a catalytic amount of a rhodium-containing catalyst, an improvement is provided which comprises carrying out said reaction in the presence of a glycolaldehyde yield-enhancing phosphine oxide.Type: GrantFiled: August 11, 1981Date of Patent: September 20, 1983Assignee: National Distillers and Chemical CorporationInventor: Richard W. Goetz
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Patent number: 4394525Abstract: A process for hydrogenating an unsaturated organic compound which comprises contacting the same with hydrogen in the presence of a catalyst composed of a support containing (1) at least one Group IIA metal compound selected from the group consisting of magnesium, calcium, strontium and barium compounds, (2) alumina and (3) aluminum phosphate carrying nickel thereon.Type: GrantFiled: June 29, 1981Date of Patent: July 19, 1983Assignee: Gulf Research & Development CompanyInventors: Roger F. Vogel, George Marcelin, Harold E. Swift
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Patent number: 4393251Abstract: Hydrogenation catalysts which are prepared from mixed crystals of copper-zinc compounds, obtained by precipitation, of the formulaCu.sub.1.5-3 Zn.sub.1-2.5 (CO.sub.3).sub.1-2 (OH).sub.4-6.(H.sub.2 O).sub.0-1by decomposition at 200.degree.-500.degree. C., and are used for the catalytic preparation of propanediols of the formula ##STR1## where the R's may be identical or different and each is an aliphatic, araliphatic or aromatic radical, or the two R's together with the adjacent carbon atom are members of an alicyclic ring, by hydrogenating hydroxypropionaldehydes of the formula ##STR2## where R has the above meanings, and to processes for the preparation of propanediols, using such catalysts. The propane-1,3-diols obtainable by the novel process are valuable starting materials for the preparation of lubricants, plastics, surface coatings and synthetic resins, for example of polyesters derived from the propanediols.Type: GrantFiled: February 10, 1982Date of Patent: July 12, 1983Assignee: BASF AktiengesellschaftInventors: Franz J. Broecker, Leopold Hupfer, Franz Merger, Ernest Miesen, Juergen Paetsch, Guenter Zirker
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Patent number: 4386018Abstract: Hydrogenation catalysts, which have a specific surface area of from 50 to 150 square meters per gram, solely or partially contain crystals having a spinel structure and copper in the form of copper oxide, and have been obtained by precipitating copper and aluminum in a ratio of from 0.25 to 3 atoms of copper per atom of aluminum from their compounds in the presence of a carbonate at a pH of from 4.5 to 9 and calcining the resulting precipitate at from 300.degree. to 800.degree. C., for the catalytic preparation of propanediols by hydrogenating hydroxypropionaldehydes at not more than 300 bar pressure and from 50.degree. to 200.degree. C., and processes for the preparation of propanediols by the use of such catalysts.The propanediols obtainable by the process of the invention, in particular 2,2-dimethylpropane-1,3-diol, are valuable starting materials for the preparation of lubricants, plastics, surface coatings and synthetic resins, for example corresponding polyesters.Type: GrantFiled: July 6, 1981Date of Patent: May 31, 1983Assignee: BASF AktiengesellschaftInventors: Franz Merger, Ernest Miesen, Franz J. Broecker, Wolfgang Schroeder, Karl Baer, Juergen Paetsch, Leopold Hupfer
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Patent number: 4375394Abstract: The present invention provides a process for the preparation of ethylene glycol and glycerine by a selective electrolysis that cleaves the carbon-carbon bonds of carbohydrate-derived polyols into two- and three-carbon units. The intermediate products can then be reduced to the desired ethylene glycol and glycerine products using standard reduction technology. The electrolysis is conducted in the presence of an electrolysis medium which contains manganese.Type: GrantFiled: March 11, 1982Date of Patent: March 1, 1983Assignee: Eastman Kodak CompanyInventor: Thomas J. Devon
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Patent number: 4326072Abstract: A method for the synthesis of L-gulonic acid by catalytically hydrogenating D-glucuronic acid utilizing a ruthenium-based catalyst.Type: GrantFiled: July 1, 1980Date of Patent: April 20, 1982Assignee: ICI Americas Inc.Inventors: Walter M. Kruse, Makram H. Meshreki
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Patent number: 4322568Abstract: An aqueous 30 wt. % solution of formaldehyde trickled with an equal volume of NaOH solution over a zeolite (NaX, 5 A, or Na Mordenite) at 94.degree. C., 1 atm, 1.21-2.36 liquid hourly space velocity, catalytically condenses to HOCH.sub.2 CHO, glycolaldehyde, a fraction of which then converts to HOCH.sub.2 CH.sub.2 OH, ethylene glycol, by cross-Cannizzaro side reaction. Zeolite degradation is prevented by maintaining pH near 11. Selectivity can be controlled so that less than 1% byproduct formose sugars are made. Methanol and sodium formate are also byproducts. All of the remaining glycolaldehyde could, in principle, be converted to ethylene glycol in either a subsequent cross-Cannizzaro reaction or a hydrogenation step. Thus, the reaction represents a potential non-petrochemical route for either glycolaldehyde or ethylene glycol from CO+H.sub.2, via methanol and formaldehyde.Type: GrantFiled: July 24, 1980Date of Patent: March 30, 1982Inventor: Alvin H. Weiss
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Patent number: 4321414Abstract: A process is provided for catalytic hydrogenation of glycolaldehyde to form ethylene glycol in liquid phase employing a homogeneous ruthenium catalyst and a basic promoter. Ethylene glycol is produced in excellent yields and selectivities, and the process permits use of mild temperature and pressure conditions.Type: GrantFiled: August 26, 1980Date of Patent: March 23, 1982Assignee: The Halcon SD Group, Inc.Inventor: Lawrence C. Costa
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Patent number: 4317946Abstract: A process is provided for catalytic hydrogenation of glycolaldehyde to form ethylene glycol in liquid phase employing a homogeneous ruthenium carboxylate complex catalyst system. Ethylene glycol is produced in excellent yields and selectivities and the process permits use of mild temperature and pressure conditions. The formation of acetals is greatly minimized as compared to prior art ruthenium catalysts.Type: GrantFiled: June 27, 1980Date of Patent: March 2, 1982Assignee: The Halcon SD Group, Inc.Inventor: Lawrence C. Costa
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Patent number: 4299986Abstract: Mixed alkoxy-hydride derivatives of aluminum and alkaline-earth metals are disclosed having the formulaM[AlH.sub.4-n (OR).sub.n ].sub.2which may be complexed with a Lewis base wherein M is an alkaline-earth metal, R is selected from an aliphatic, cycloaliphatic or aromatic group having from 1 to 20 carbon atoms and n is a number between 0.5 and 3.5. There is also disclosed a novel process for preparing said derivatives which are useful as reducing agents.Type: GrantFiled: December 18, 1979Date of Patent: November 10, 1981Assignee: Anic, S.p.A.Inventor: Salvatore Cucinella
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Patent number: 4298766Abstract: A process for the preparation of 2-methyl-pentane-2,4-diol by hydrogenating diacetone-alcohol at an elevated temperature in the presence of a catalyst which has been obtained by calcining the compound of the formula Ni.sub.6 Al.sub.2 (OH).sub.16 CO.sub.3 . 4H.sub.2 O.Type: GrantFiled: September 17, 1979Date of Patent: November 3, 1981Assignee: BASF AktiengesellschaftInventors: Franz J. Broecker, Karl G. Baur, Rolf Platz, Joachim Stabenow
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Patent number: 4275243Abstract: An organic tri-substituted phosphine having a boiling point of at least 200.degree. C. and a reaction medium having a boiling point of at least 200.degree. C. are used in a hydroformylation of allyl alcohol with carbon monoxide and hydrogen in the presence of a rhodium complex catalyst. The concentration of the organic phosphine is 5.times.10.sup.-4 to 0.3 mol. per 1 liter of the reaction medium. The reaction medium is distilled at lower than 80.degree. C. under a reduced pressure and the bottom residue as the catalyst solution is recycled. The hydroformylation can be repeated by using the bottom residue as the catalyst solution.Type: GrantFiled: August 27, 1979Date of Patent: June 23, 1981Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Toshihiro Saito, Shoji Arai, Yukihiro Tsutsumi
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Patent number: 4273933Abstract: A modified nickel catalyst used for stereo-differentiating reduction of carbonyl compounds is provided. The modified nickel catalyst is prepared by soaking a nickel catalyst in an aqueous modifying medium having dissolved therein at least one inorganic salt, such as sodium bromide or sodium chloride, and at least one optically active substance, such as optically active hydroxy acid. The modified nickel catalyst exhibits enhanced activity for stereo-differentiating reduction and causes little or no side reactions, and thus, brings about an extremely high yield of the reaction product.Type: GrantFiled: April 25, 1979Date of Patent: June 16, 1981Assignee: Kawaken Fine Chemicals Co., Ltd.Inventors: Tadao Harada, Yoshiharu Izumi, Shinichiro Komatsu
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Patent number: RE32084Abstract: A process for preparing glycol aldehyde by reacting formaldehyde, hydrogen and carbon monoxide at elevated temperature and superatmospheric pressure in the presence of rhodium catalyst and conversion thereof to ethylene glycol as the substantially exclusive polyol product.Type: GrantFiled: October 4, 1983Date of Patent: February 18, 1986Assignee: National Distillers and Chemical CorporationInventor: Richard Goetz