Containing Alicyclic Ring Having At Least Seven Members Patents (Class 568/821)
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Patent number: 4506105Abstract: A process for preparing cyclooctene-4-ol-1 with a content in excess of 70% by reacting cyclooctadiene-1,5 with formic acid and then saponifying or transesterifying the cyclooctenyl formate with an alcohol of low boiling point.In the absence of a catalyst, formic acid is reacted with cyclooctadiene-1,5 at 50.degree. to 200.degree. C., preferably 95.degree. to 105.degree. C. The reaction product without further processing is directly distilled, and the formic acid ester so obtained is transesterified with an alcohol of low boiling point into the formate of that alcohol and into cyclooctene-4-ol-1.Type: GrantFiled: August 4, 1983Date of Patent: March 19, 1985Assignee: Chemische Werke Huls AGInventor: Manfred Kaufhold
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Patent number: 4499313Abstract: An improved process for producing an alcohol by hydrating an olefin, wherein the improvement comprises hydrating an olefin in the presence of hydrogen-type mordenite or hydrogen-type zeolite Y as a catalyst each having a silica/alumina molar ratio of 20 to 500.Type: GrantFiled: April 30, 1984Date of Patent: February 12, 1985Assignee: Toa Nenryo Kogyo Kabushiki KaishaInventors: Yoshiharu Okumura, Setsuo Kamiyama, Toshihiro Hosokawa, Katsumi Kaneko
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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: 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: 4496777Abstract: Production of halohydrins; in particular, chlorohydrins by reaction of tertiary alkyl hypohalite and olefinically unsaturated compound in the presence of water and a water soluble salt of an amphoteric metal; in particular, a salt of tin, aluminum, zinc, zirconium, magnesium, or titanium, which provides a pH of from 2 to 5 under reaction conditions.Type: GrantFiled: November 9, 1983Date of Patent: January 29, 1985Assignee: The Lummus CompanyInventors: George D. Suciu, Joon T. Kwon, Atef M. Shaban
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Patent number: 4487972Abstract: This specification discloses a process for the production of oxygenated compounds, more specifically aldehydes and alcohols, by reacting an olefin with hydrogen and carbon monoxide in the presence of, as a ctalyst, an insoluble polymer containing a functional group, which may be an amine, thiol, phosphine, or arsine group, having chemically bonded thereto a metal of Group VIII of the Periodic Table. The metal can be, for example, rhodium, cobalt, or ruthenium. The olefin can contain more than one carbon-to-carbon double bond, may be an open chain or a cyclic olefin, and may be substituted. Further, the olefin may be contained in a refinery stream such as a cracked gasoline. The reaction may be carried out in the presence of a polar solvent.Type: GrantFiled: April 22, 1980Date of Patent: December 11, 1984Assignee: Mobil Oil CorporationInventors: Werner O. Haag, Darrell D. Whitehurst
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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: 4479020Abstract: Production of halohydrins; in particular, chlorohydrins by reaction of tertiary alkyl hypohalite and olefinically unsaturated compound in the presence of water and a metal selected from Group II-A, II-B, III-A, III-B, IV-A, IV-B, or V-A of the Periodic Table. The use of such metals improves the production of halohydrin.Type: GrantFiled: November 12, 1982Date of Patent: October 23, 1984Assignee: The Lummus CompanyInventors: George D. Suciu, Joon T. Kwon, Atef M. Shaban
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Patent number: 4438287Abstract: Alcohols may be prepared in a combination process by subjecting an aliphatic paraffinic hydrocarbon feed stream to a dehydrogenation reaction and thereafter subjecting the reaction product mix comprising a mixture of aliphatic paraffinic hydrocarbons and aliphatic olefinic hydrocarbons, without separating the olefins in the product mix from the paraffins, to a hydroformylation reaction. The hydroformylation reaction is effected by treating said product mix with carbon monoxide and hydrogen in the presence of a catalyst comprising a rhodium-containing compound and a promoter comprising a trialkyl-substituted monoamine, all three of said alkyl moieties being substituted to the nitrogen of said amine to selectively prepare the desired alcohols.Type: GrantFiled: August 25, 1982Date of Patent: March 20, 1984Assignee: UOP Inc.Inventor: Tamotsu Imai
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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: 4393245Abstract: New 1-acyl- and 1-hydroxymethyl-cyclododecanes and -cyclododecenes. The new 1-acyl-cyclododecenes and -cyclododecanes are obtained by a Rupe or Meyer-Schuster rearrangement, with or without subsequent hydrogenation in the presence of Ni, Pd and Pt catalysts. The 1-acyl-cyclododecenes and -cyclododecanes are valuable scents of the basic type of the sought-after macrocyclic musk scents. Furthermore, they are used for the manufacture of numerous other new 1-substituted or 1-and 2-substituted cyclododecenes and cyclododecanes having good scent characteristics.Type: GrantFiled: December 2, 1981Date of Patent: July 12, 1983Assignee: BASF AktiengesellschaftInventors: Werner Hoffman, Karl von Fraunberg, Manfred Baumann
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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: 4385185Abstract: Compounds of the general formula I: ##STR1## wherein R.sub.1 and R.sub.2 are equal or different alkyl-, alkoxyalkyl-, or aryl groups, or together form a ring; R.sub.3 is an allyl or benzyl radical; and R.sub.4 and R.sub.5 represent hydrogen, alkyl, alkoxyalkyl, alkenyl or further compounds of the formula II: ##STR2## wherein R.sub.1, R.sub.2, R.sub.4 and R.sub.5 have the meaning indicated above and R.sub.6 stands for hydrogen or methyl or to compounds which are modified by the addition of hydrogen to at least one olefinic or carbonylic double bond of compounds of the general formula I or II. The invention also relates to a process for preparing the new compounds. The compounds of the general formula II are obtained by thermal treatment of a selection of compounds of formula I, for which R.sub.3 stands for the allyl or methallyl radical. The compounds according to the invention are used as fragrant and flavoring substances.Type: GrantFiled: March 20, 1981Date of Patent: May 24, 1983Assignee: Consortium fur Elektrochemische Industrie GmbHInventors: Helmut Gebauer, Walter Hafner
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Patent number: 4370257Abstract: A process for producing a magnesium containing support for titanium comprising contacting magnesium metal, a halogenated hydrocarbon and a compound represented by the formula X'.sub.m C(OR').sub.4-m wherein X' is a hydrogen atom, a halogen atom or a C.sub.1 -C.sub.10 alkyl, aryl, cycloalkyl or halogenated alkyl, aryl, cycloalkyl group, R' is a C.sub.1 -C.sub.20 alkyl, aryl or cycloalkyl group and m is 0, 1 or 2 to form a magnesium-containing solid represented by the formula R'OMgX and thereafter contacting the magnesium-containing solid with a Lewis base or a compound which can form an ester such as benzoyl chloride and a titanium compound such as titanium tetrachloride. The obtained magnesium supported titanium composition is useful as a catalyst component in combination with a co-catalyst organoaluminum compound for the polymerization of olefins.Type: GrantFiled: August 11, 1980Date of Patent: January 25, 1983Assignee: Toa Nenryo Kogyo Kabushiki KaishaInventors: Masafumi Imai, Hiroshi Ueno, Naomi Inaba, Makoto Yoda, Shozo Wada
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Patent number: 4346240Abstract: A novel class of heterogeneous catalysts, containing Group VIII transition metals in combination with alkali organic compounds is prepared, such as potassium naphthalene on ruthenium on carbon. The catalysts are useful as heterogeneous catalysts in the hydrogenation of carboxylic acid esters. A process for producing the materials is described. The catalysts permit the process of the hydrogenation of carboxylic acid esters to primary alcohols to be conducted with the ester in the liquid phase at a temperature not exceeding about 150.degree. C. with high selectivity. Catalysts of Group VIII transition metals and alkali metal on carbon are also useful in such processes.Type: GrantFiled: September 29, 1981Date of Patent: August 24, 1982Assignee: Allied CorporationInventors: Roger A. Grey, Guido P. Pez
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Patent number: 4341907Abstract: A process is disclosed for the catalytic oxidation of a cycloparaffin, e.g., cyclohexane, to partial oxidation products thereof, especially for the production of mixtures of cycloalkanols and cycloalkanones. In the process, molecular oxygen, usually in the presence of an inert gas, is introduced into the cycloparaffin at elevated pressure and a temperature of 130.degree.-180.degree. C., in the presence of an oxidation catalyst comprising a heavy metal compound along with an N-heterocyclic compound. The heavy metal of the heavy metal compound may be cobalt, vanadium, manganese, copper, iron or nickel. The heavy metal compound may have ligands of alkanoate, dialkylphosphate, dicycloalkylphosphate or alkylcycloalkylphosphate. The N-heterocyclic compound may be dipyridyl, pyrimidine, pyrazine, pyridine and pyridine substituted with --CN, --R, and/or --OR where R is alkyl. A preferred catalyst is cobalt bis[di(2-ethylhexyl)phosphate] in combination with pyridine.Type: GrantFiled: January 30, 1981Date of Patent: July 27, 1982Assignee: Du Pont Canada Inc.Inventor: Ronald A. Zelonka
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Patent number: 4338290Abstract: Glycols are readily and conveniently prepared by hydrolysis of halohydrins and/or dihaloalkanes in the presence of a catalytically effective amount of a strong acid.Type: GrantFiled: June 16, 1980Date of Patent: July 6, 1982Assignee: National Distillers & Chemical Corp.Inventors: Jawad H. Murib, John M. Inskeep
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Patent number: 4310709Abstract: The process for the manufacture of but-2-en-1-ol compounds by isomerizing but-3-en-1-ol compounds in the presence of a palladium catalyst and of hydrogen is improved by modifying the palladium catalyst with selenium or tellurium.The but-2-en-1-ols manufactured according to the invention are either solvents or valuable starting materials for the manufacture of solvents, dyes, surface coatings, paints and pesticides.Type: GrantFiled: April 23, 1980Date of Patent: January 12, 1982Assignee: BASF AktiengesellschaftInventor: Walter Rebafka
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Patent number: 4285820Abstract: A process for the treatment of a waste liquid containing boron compounds and organic compounds, such as resulting from the oxidation of paraffins with oxygen in the presence of boron compounds, includes combusting the waste liquid in a furnace at a temperature higher than 1000.degree. C. in the presence of a large amount of steam. The combustion gas may be introduced into a heat recovery zone, preferably a boiler, to recover the heat thereof and then into a contacting vessel to bring same into contact with water and to recover the boron components contained in the gas. Since substantially all the boron components contained in the combustion gas are present in the form of gaseous metaboric acid, there is caused no deposition of boron oxide onto the interior walls of the combustion furnace or gas passages in the boiler.Type: GrantFiled: December 11, 1979Date of Patent: August 25, 1981Assignee: Nittetu Chemical Engineering Ltd.Inventor: Mikio Akune
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Patent number: 4271091Abstract: Cyclohexanone and/or cyclohexanol can be oxidized in the vapor phase to phenol by contacting the cyclohexanone and/or cyclohexanol with a suitable oxidation catalyst in the presence of molecular oxygen. Suitable catalysts are solids comprising Mo, W, Sb and/or V oxides or complexes thereof. The catalysts may be promoted with additional elements.Type: GrantFiled: June 17, 1978Date of Patent: June 2, 1981Assignee: Standard Oil CompanyInventors: Robert K. Grasselli, Dev D. Suresh
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Patent number: 4268443Abstract: This invention is directed to 13,15-dioxabicyclo[10.5.0]heptadecanes having the structural formula ##STR1## wherein R and R.sup.1 are independently hydrogen or a methyl radical. The invention is also directed to their preparation, their use as perfuming agents and as olefactant components in perfume compositions and as an odorant agent for technical products.Type: GrantFiled: June 14, 1979Date of Patent: May 19, 1981Assignee: Henkel Kommanditgesellschaft auf Aktien (Henkel KGaA)Inventors: Klaus Bruns, Peter Meins
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Patent number: 4263447Abstract: Allylic cycloalkenols and/or allylic cycloalkenol esters are prepared by autoxidation of the corresponding cycloolefins using elemental oxygen contacted with solutions of cycloolefins containing catalytic amounts of soluble cobalt and copper compounds with a carboxylic acid activator.Type: GrantFiled: July 16, 1979Date of Patent: April 21, 1981Assignee: Union Carbide CorporationInventors: Benjamin Phillips, Walter J. Skraba, Daniel W. McNeil
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Patent number: 4255595Abstract: Optically active compounds are prepared from optically inactive unsaturated hydrocarbons by reacting at least one unsaturated hydrocarbon in the presence of a catalyst prepared by combining a nickel compound, a Lewis acid and an optically active phosphine of the general formulaPR'R"R'"in which R', R" and R'" are hydrocarbon radicals, thereby forming optically active compounds having chiral centers formed by the carbon-to-carbon linkages. The optically active compounds can be polymerized to provide optically active polymers.Type: GrantFiled: October 10, 1979Date of Patent: March 10, 1981Assignee: Studiengesellschaft Kohle mbHInventors: Gunther Wilke, Borislav Bogdanovic, Horst Pauling
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Patent number: 4214098Abstract: Novel cyclooctene derivatives of the formula: ##STR1## in which R.sup.1 and R.sup.2 each represents an alkyl group and R.sup.3 is hydrogen or an acyl group are disclosed along with their use as aroma chemicals and/or aroma chemical precursors and processes for their preparation.Type: GrantFiled: October 25, 1977Date of Patent: July 22, 1980Assignee: Shell Oil CompanyInventors: Aaldert J. de Jong, Hendricus J. Heijmen
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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: 4183904Abstract: A method for the recovery of boron compounds from waste streams containing boric acid and combustible organic materials in water by incineration of the combustible organic materials and dehydration of the boric acid to boric oxide. Quenching of the boric oxide, depending upon temperature and water content, yields orthoboric and/or metaboric acids in vapor phase and polyboric acid in liquid phase which is cooled along with the products of the combustion of the organic materials and, in the presence of water, converted to a mixture of boric acids in solid and liquid phase leaving the products of combustion in vapor phase. The mixture of boric acids is then separated from the products of combustion.Type: GrantFiled: October 3, 1977Date of Patent: January 15, 1980Assignee: Monsanto CompanyInventor: Oscar A. Meyer
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Patent number: 4181810Abstract: A process for the preparation of a propane-1,3-diol, disubstituted in the 2-position, which comprises contacting an ethanal disubstituted in the 2-position, which ethanal has the formula ##STR1## wherein R.sup.1 and R.sup.2 are identical or different and denote optionally substituted alkyl, cycloalkyl, aralkyl or aryl radicals or an optionally substituted heterocyclic radical, or together denote an optionally substituted divalent hydrocarbon radical with formaldehyde in the presence of an acid ion exchanger and thereafter contacting the resultant reaction product with hydrogen under hydrogenation conditions.Type: GrantFiled: November 16, 1977Date of Patent: January 1, 1980Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Hans-Helmut Schwarz, Oskar Weissel
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Patent number: 4163865Abstract: An improvement in a process for the preparation of a pinacol of the formula ##STR1## wherein R.sup.1 and R.sup.2 are identical or different and represent optionally substituted aliphatic, cycloaliphatic, araliphatic or an aromatic hydrocarbon radical by reducing a ketone of the formula ##STR2## wherein R.sup.1 and R.sup.2 have the abovementioned meanings with a base metal, the improvement comprising carrying out the reduction in the presence of an organic halogen compound and in the presence of a phosphoric acid amide, phosphoric acid ester and/or carboxylic acid amide.Type: GrantFiled: April 3, 1978Date of Patent: August 7, 1979Assignee: Bayer AktiengesellschaftInventors: Heinrich Wolfers, Hans Rudolph, Hans-Jurgen Rosenkranz
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Patent number: 4152366Abstract: Optically active compounds are prepared from optically inactive unsaturated hydrocarbons by reacting at least one unsaturated hydrocarbon in the presence of a catalyst prepared by combining a nickel compound, a Lewis acid and an optically active phosphine of the general formulaPR'R"R"'in which R', R" and R"' are hydrocarbon radicals, thereby forming optically active compounds having chiral centers formed by the carbon-to-carbon linkages. The optically active compounds can be polymerized to provide optically active polymers.Type: GrantFiled: September 22, 1977Date of Patent: May 1, 1979Assignee: Studiengesellschaft Kohle mbHInventors: Gunther Wilke, Borislav Bogdanovic, Horst Pauling
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Patent number: 4117246Abstract: A process for the preparation of cycloalkanol by way of a two stage reaction from cycloalkene. The first reaction stage consists of reacting cycloalkene with sulphuric acid. The resultant adduct which is cycloalkyl hydrogen sulphate is separated from the reaction mixture by use of an inert solvent. The adduct is then hydrolyzed in the second reaction stage to product the cycloalkanol.Type: GrantFiled: December 9, 1977Date of Patent: September 26, 1978Assignee: Stamicarbon, B.V.Inventor: Otto G. Plantema
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Patent number: 4113968Abstract: When 1-halogeno-3-alkene-2-ol is reacted with an ortho-carboxylic ester and/or a ketene acetal, a .gamma.-halogeno-.delta.-unsaturated-carboxylic ester is obtained as a main reaction product. When this intermediate is treated with a basic substance, a substituted cyclopropane-carboxylic ester is formed. This ester can be used as an insecticide or an agricultural chemical as it is or after the alcohol residue of the ester has been converted to other alcohol residue.Type: GrantFiled: September 26, 1975Date of Patent: September 12, 1978Assignee: Kuraray Co., Ltd.Inventors: Fumio Mori, Yoshiaki Omura, Takashi Nishida, Kazuo Itoi
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Patent number: 4087472Abstract: An olefinic hydrocarbon is isomerized utilizing a catalyst system consisting essentially of a mixture of a nickel complex of the formula (R.sub.3 P).sub.2 NiX.sub.2 and an alkali metal borohydride.Type: GrantFiled: August 16, 1976Date of Patent: May 2, 1978Assignee: Phillips Petroleum CompanyInventor: William B. Hughes