Supported Hydrogenation Catalyst Utilized Patents (Class 568/883)
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Patent number: 5463147Abstract: Mixtures of isomeric decyl alcohols prepared by hydroformylation of mixtures of butene-1 and butene-2 in two stages to give aldehyde mixtures, and condensation of the aldehyde mixtures to form an aldol mixture, followed by separation and hydrogenation. The first stage of the hydroformylation proceeds in the presence of rhodium catalysts dissolved in water, the second stage in the presence of cobalt catalysts homogeneously dissolved in the reaction medium. The mixture of isomeric decyl alcohols, when esterified with phthalic acid, yields a mixture of isomeric decyl phthalates which are useful as plasticizers.Type: GrantFiled: September 23, 1994Date of Patent: October 31, 1995Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Wolfgang Greb, Peter Heymanns, Peter Lappe, Thomas Muller, Jurgen Szameitat, Ernst Wiebus
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Patent number: 5457240Abstract: A method for starting a preformer reactor disposed within a hydroformylation system which comprises an oxo reactor, a stripper reactor and a preformer reactor, wherein the bottoms from the stripper reactor comprise at least a water soluble cobaltous salt and wherein the overhead from the stripper reactor comprises entrained volatile cobalt compounds, wherein at least a portion of the entrained volatile cobalt compounds from the stripper reactor are recycled to the preformer reactor to act an initiator in the conversion of the cobaltous salt to cobalt carbonyl.Type: GrantFiled: December 14, 1994Date of Patent: October 10, 1995Assignee: Exxon Chemical Patents, Inc.Inventors: Stephen W. Beadle, Claude A. Poulin
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Patent number: 5446213Abstract: The present invention is directed to a method of dimerizing lower olefins which comprises dimerizing a lower olefins in the presence of a catalyst, wherein the catalyst used comprises a nickel compound, an organic aluminum compound, and a phosphite compound having the general formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are phenyl groups optionally substituted by substituents and may be different from each other, at least two of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 have a hydrocarbon group as a substituent in the ortho position; A is a divalent aliphatic, alicyclic or aromatic hydrocarbon group which optionally has a substituent; and n is 0 or 1. The present invention is also directed a method of producing alcohol by means of hydroformylating and hydrogenating the newly formed olefins obtained through the said dimerization method of the lower olefins.Type: GrantFiled: June 3, 1994Date of Patent: August 29, 1995Assignee: Mitsubishi Kasei CorporationInventors: Keiichi Sato, Yuuji Kawaragi, Yasuko Higashino
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Patent number: 5434318Abstract: Noble metal or other preformer catalysts used to convert cobalt salts to hydrido cobalt carbonyl for use in the oxonation of olefins are reactivated or regenerated by treatment with a mixture of an aqueous organic acid solution and an alcohol at a temperature of about 120.degree. C. to 170.degree. C. and a pressure of about 13.78 MPa to 31.00 MPa for about 2 to 50 hours.Type: GrantFiled: March 23, 1994Date of Patent: July 18, 1995Assignee: Exxon Chemical Patents Inc.Inventors: Ronald R. Hill, Patricia B. Roussel
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Patent number: 5434312Abstract: 1,3-Butadiene is hydroformylated at 60.degree. to 150.degree. C. and 1 to 20 MPa in the presence of an aqueous solution which contains, as catalyst, at least one water-soluble rhodium compound and at least one water-soluble organic phosphine. A pH of 8 to 11 is maintained in the aqueous catalyst solution to increase the selectivity of the reaction with respect to the formation of n-five carbon aldehydes and their secondary products. The latter, in particular, can be hydrogenated to 2-propylheptanol, useful as the alcohol component of phthalic ester plasticizers.Type: GrantFiled: September 2, 1994Date of Patent: July 18, 1995Assignee: Hoechst AktiengesellschaftInventors: Bernhard Fell, Peter Hermanns
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Patent number: 5414160Abstract: A method for dimerizing an n-butene wherein a catalyst system is used which is produced in situ from an organonickel compound having no nickel-halogen bond, a triarylphosphine and/or a monoalkyldiarylphosphine, an organoaluminum compound and hydrogen. The resulting octenes are excellent as a raw material of alcohols for a plasticizer, and an excellent plasticizer can be obtained from alcohols having 9 carbon atoms produced by using the octenes.Type: GrantFiled: June 16, 1994Date of Patent: May 9, 1995Assignee: Mitsubishi Kasei CorporationInventors: Keiichi Sato, Yuuji Kawaragi, Yasuko Higashino
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Patent number: 5399793Abstract: The hydrogenation steps and hydrofinishing steps of the cobalt catalyst oxo process for preparation of the alcohols by the hydroformylation of olefin are carried out using a catalyst containing Ni/Mo on alumina or silica alumina prepared by depositing an organic acid solution of Ni and Mo salts on the support, the acid being phosphorous free.Type: GrantFiled: November 29, 1993Date of Patent: March 21, 1995Assignee: Exxon Chemical Patents Inc.Inventors: Jose M. Vargas, Magdiel Agosto, Kenneth L. Riley
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Patent number: 5382716Abstract: Mixtures of isomeric decyl alcohols obtained by hydroformylation of butadiene to produce aldehyde mixtures, condensation of the aldehyde mixtures, isolated from the reaction product, to form an aldol mixture, and isolation and hydrogenation of the aldol mixture. The mixture of isomeric decyl alcohols, esterified using phthalic acid, gives a mixture of isomeric decyl phthalates which are plasticizers having excellent cold properties.Type: GrantFiled: March 23, 1993Date of Patent: January 17, 1995Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Wolfgang Greb, Peter Heymanns, Peter Lappe, Jurgen Szameitat, Thomas Muller, Ernst Wiebus
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Patent number: 5321168Abstract: Noble metal or other preformer catalysts used to convert cobalt salts to hydrido cobalt carbonyl for use in the oxonation of olefins are activated or regenerated by treatment with H.sub.2 O at 120.degree. to 170.degree. C., 13.78 MPa (2,000 psig) to 31.00 MPa (4,500 psig) for 2-50 hours.Type: GrantFiled: September 16, 1993Date of Patent: June 14, 1994Assignee: Exxon Chemical Patents Inc.Inventors: Patricia B. Roussel, William H. Summerlin
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Patent number: 5306848Abstract: The hydrogenation steps and hydrofinishing steps of the cobalt catalyst oxo process for the preparation of alcohols by the hydroformylation of olefin are carried out using a trimetallic catalyst composed of metal oxides, particularly nickel oxide, molybdenum oxide and cobalt oxide supported on alumina or an alumina-silica in sulfided and non-sulfided form.Type: GrantFiled: October 16, 1992Date of Patent: April 26, 1994Assignee: Exxon Chemical Patents Inc.Inventor: Jose M. Vargas
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Patent number: 5268514Abstract: Mixtures of isomeric decyl alcohols are obtained by hydroformylation of 1-butene- and 2-butene-containing mixtures in two stages to give aldehyde mixtures, condensation of the isolated and combined aldehyde mixtures to form an aldol mixture, and isolation and hydrogenation of the aldol mixture. The mixture of isomeric decyl alcohols, esterified with phthalic acid, gives a mixture of isomeric decyl phthalates which are useful as plasticizers.Type: GrantFiled: March 22, 1993Date of Patent: December 7, 1993Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Wolfgang Greb, Peter Lappe, Peter Heymanns, Jurgen Szameitat, Thomas Muller, Ernst Wiebus
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Patent number: 5071572Abstract: In the the oxo process for alcohol production the heavy component left after enriching and recycling is itself recycled to oxonation to give yield improvement.Type: GrantFiled: September 1, 1989Date of Patent: December 10, 1991Assignee: Exxon Chemical Patents Inc.Inventor: Nicolaas A. De Munck
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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: 4709105Abstract: Preparation of C.sub.3 - to C.sub.25 -alkanols by catalytic hydrogenation of corresponding crude C.sub.3 - to C.sub.25 -alkanols, as obtained in the cobalt-catalyzed hydroformylation of C.sub.2 - to C.sub.24 -olefins, by partial 80-95% hydrogenation conversion in a first stage using a silica supported nickel and molybdenum oxide catalyst and then completing the conversion in a second stage using a cobalt catalyst containing copper, manganese, molybdenum and,optionally other activating additives. The process is especially adapted to the economic preparation of C.sub.9 -C.sub.11 - and C.sub.13 -C.sub.15 -alkanols which are used to prepare high-grade plasticizer esters.Type: GrantFiled: November 19, 1986Date of Patent: November 24, 1987Assignee: BASF AktiengesellschaftInventors: Armin V. Grenacher, Max Strohmeyer, Herwig Hoffmann, Heinrich Elliehausen
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Patent number: 4684750Abstract: A process for the production of 2-ethyl-hexanol comprising reacting propene with carbon monoxide and hydrogen, in the presence of an aqueous catalyst containing rhodium and at least one sulfonated triarylphosphine, to form an aqueous phase and an organic phase, said organic phase comprising a mixture of materials having boiling points lower than that of n-butanal and substances having boiling points equal to or higher than that of n-butanal, said materials including i-butanal, separating said material from said substances, subjecting said substances to aldol condensation, in the presence of aqueous alkali, to form 2-ethyl hexenal, first hydrogenating said 2-ethyl-hexenal in a gas phase in the presence of a first hydrogenation catalyst and thereafter hydrogenating said 2-ethyl-hexenal in a liquid phase to form 2-ethyl-hexanol in the presence of a second hydrogenation catalyst.Type: GrantFiled: August 26, 1986Date of Patent: August 4, 1987Assignee: Ruhrchemie AktiengesellschaftInventors: Gunther Kessen, Boy Cornils, Wilhelm Gick, Ernst Wiebus, Joseph Hibbel, Hanswilhelm Bach, Wolfgang Zgorzelski
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Patent number: 4658068Abstract: The higher alcohol yield of a hydroformylation process comprising catalytic hydroformylation of olefinic feedstock and hydrogenation of the crude product is improved by separating light materials and desired alcohols from the hydrogenated product, and then subjecting the remaining heavy materials to catalytic steam cracking at 260.degree.-380.degree. C. The fraction of the cracked product which is rich in alcohol/aldehyde is then separated and recycled, preferably to the hydrogenation stage.Type: GrantFiled: November 27, 1985Date of Patent: April 14, 1987Assignee: Exxon Research & Engineering Co.Inventor: Jean A. A. Hanin
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Patent number: 4647708Abstract: A method of controlling metal leaching in heterogeneous catalysis conducted in the presence of a solid-supported, metal complex catalyst with liquid feed subject to inclusion of ligands competitive with the solid support for the metal complex. The method is specifically applicable where the heterogeneous catalysis reaction is a combined hydroformylation/reduction reaction producing aldehydes and alcohols from olefins.Type: GrantFiled: November 25, 1985Date of Patent: March 3, 1987Assignee: The Dow Chemical CompanyInventors: Douglas L. Hunter, Stanley E. Moore, Gordon G. Willis
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Patent number: 4642395Abstract: A combined hydroformylation/reduction reaction is enhanced by the control of halide concentration in the feed olefin, solvent and solid supported transition metal complex catalyst to produce higher initial reaction rate and longer catalyst life.Type: GrantFiled: November 18, 1985Date of Patent: February 10, 1987Assignee: The Dow Chemical CompanyInventors: Douglas L. Hunter, Stanley E. Moore
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Patent number: 4608444Abstract: A process and accompanying catalyst for the hydroformylation of formaldehyde to glycol aldehyde is disclosed. The process features the utilization of (1) a class of transition metal phosphine-amide complexes, (2) a class of transition metal phosphine-amine complexes, and (3) mixtures of 1 and 2 as particularly suitable for use.Type: GrantFiled: March 1, 1985Date of Patent: August 26, 1986Assignee: The Halcon SD Group, Inc.Inventor: Stephen E. Jacobson
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Patent number: 4518809Abstract: A novel, liquid mixture of C.sub.14 isomeric alcohols is described which is suitable for use in forming effective and biodegradable detergents, the alcohols being characterized by a 5-carbon branch at the 2-position and moderate additional branching in most isomers; the alcohols are prepared by a novel economic route from propylene dimer, involving oxo, aldol and hydrogenation reactions with the oxo reaction conducted in such a way as to give a high percentage of aldolable product and preferably with a base-catalyzed aldol reaction conducted under particular conditions to make high conversions attainable.Type: GrantFiled: June 1, 1983Date of Patent: May 21, 1985Assignee: Monsanto CompanyInventors: Denis Forster, George F. Schaefer
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Patent number: 4511743Abstract: Process for the homologation of an alcohol wherein a ketal of the alcohol is reacted with hydrogen and carbon monoxide in the presence of a cobalt carbonyl complex and the resultant product is hydrolyzed to yield the aldehyde with one more carbon atom.Type: GrantFiled: November 4, 1983Date of Patent: April 16, 1985Assignee: Institut Francais du PetroleInventors: Claude Seite, Dominique Commereuc, Yves Chauvin
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Patent number: 4481375Abstract: The present invention relates to hydrogenation and hydroformylation catalysts based on a binuclear rhodium complex having the formula: ##STR1## wherein X and X' can be the same or different; when X and X' are the same they are organic tertiary phosphite groups and when different X is a CO group and X' is an organic tertiary phosphite group or an aromatic phosphine group, and SY and SY' are thiolato groups. The invention also comprises the processes of hydroformylation and hydrogenation using such catalytic complex.Type: GrantFiled: November 16, 1979Date of Patent: November 6, 1984Assignee: Produits Chimiques Ugine KuhlmannInventors: Philippe Kalk, Rene Poilblanc, Antoine Gaset
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Patent number: 4454353Abstract: Described is a carbonylation process using novel homogeneous trihydrocarbyl silyl-substituted alkyl diaryl phosphine transition metal complexes of the general formula:[(Ar.sub.2 PQ).sub.y SiR.sub.4 -y].sub.g (MX.sub.n).sub.swherein Ar is a C.sub.6 to C.sub.10 aromatic hydrocarbyl radical, Q is a C.sub.1 to C.sub.30 saturated straight chain divalent radical, R is a C.sub.1 to C.sub.10 hydrocarbyl, wherein Ar, Q and R, can be substituted or unsubstituted, y is 1 to 4, g times y is 1 to 6, M is a transition metal selected from the group consisting of Group VIII transition metals, X is an anion or organic ligand excluding halogen satisfying the valence and coordination sites of the metal, n is 2 to 6 and s is 1 to 3, are disclosed. These materials exhibit high thermal stability and are superior catalysts for the selective hydroformylation of olefins, particularly in the presence of excess quantities of ligand of the formula:(Ar.sub.2 PQ)ySiR.sub.4-ywherein Ar, Q, R, and y are as previously defined.Type: GrantFiled: September 29, 1982Date of Patent: June 12, 1984Assignee: Exxon Research and Engineering Co.Inventors: Alexis A. Oswald, Torris G. Jermansen, Andrew A. Westner, I-Der Huang
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Patent number: 4451673Abstract: Described is a carbonylation process using novel homogeneous trihydrocarbyl silyl-substituted alkyl diaryl phosphine transition metal complexes of the general formula:[(Ar.sub.2 PQ).sub.y SiR.sub.4 --y].sub.g (MX.sub.n).sub.swherein Ar is a C.sub.6 to C.sub.10 aromatic hydrocarbyl radical, Q is a C.sub.1 to C.sub.30 saturated straight chain divalent radical, R is a C.sub.1 to C.sub.10 hydrocarbyl, wherein Ar, Q and R, can be substituted or unsubstituted, y is 1 to 4, g times y is 1 to 6, M is a transition metal selected from the group consisting of Group VIII transition metals, X is an anion or organic ligand excluding halogen satisfying the valence and coordination sites of the metal, n is 2 to 6 and s is 1 to 3, are disclosed. These materials exhibit high thermal stability and are superior catalysts for the selective hydroformylation of olefins, particularly in the presence of excess quantities of ligand of the formula:(Ar.sub.2 PQ)ySiR.sub.4-ywherein Ar, Q, R, and y are as previously defined.Type: GrantFiled: September 29, 1982Date of Patent: May 29, 1984Assignee: Exxon Research and Engineering Co.Inventors: Alexis A. Oswald, Torris G. Jermansen, Andrew A. Westner, I-Der Huang
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Patent number: 4426542Abstract: A preparation of a plasticizer alcohol, consisting of predominantly 2-propylheptanol, from linear butenes is described in which oxo product of the butenes is aldoled to condense n-pentaldehyde therein with very little cross-aldolization followed by hydrogenation to obtain the 2-propylheptanol with very small 2-propyl-4-methyl hexanol content. The alcohol product as phthalate ester has excellent plasticizer properties. Also processes are described for converting other olefins to alcohols by oxo, aldol and hydrogenation reactions, with particular attention to converting hexenes obtained by propylene dimerization to C.sub.14 alcohols suitable for preparation of detergents.Type: GrantFiled: June 11, 1981Date of Patent: January 17, 1984Assignee: Monsanto CompanyInventors: George E. Barker, Denis Forster
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Patent number: 4426541Abstract: Aliphatic alcohols are produced by an improved hydrogenation of the corresponding saturated aliphatic aldehydes in the presence of organo-sulfur impurities by partially hydrogenating the aldehydes in a first hydrogenation zone in the presence of a sulfided hydrogenation catalyst at a temperature within the range of from about 180.degree. to 260.degree. C., followed by completion of the hydrogenation in the second hydrogenation zone in the presence of a metallic nickelcontaining hydrogenation catalyst. The second hydrogenation zone employs a lower temperature than is used in the first and is selected within the range of from about 175.degree. to 250.degree. C.Type: GrantFiled: March 16, 1982Date of Patent: January 17, 1984Assignee: Exxon Research & Engineering Co.Inventor: Terry S. King
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Patent number: 4401834Abstract: An improved process for producing alcohols which comprises passing a demetalled hydroformylation liquid effluent comprising aldehyde and alcohol and containing acetal impurities to a thermal treatment zone; subjecting the demetalled hydroformylation effluent in the thermal treatment zone in the absence of added acidic compounds and in the presence of water to a temperature of from about 350.degree. to 500.degree. F. for a time sufficient to convert at least a major portion of the acetal impurities to the corresponding aldehydes and alcohols and to form an aldehyde-containing liquid containing substantially reduced levels of the acetal impurities; withdrawing the aldehyde-containing liquid from the thermal treatment zone and rapidly cooling the liquid to a temperature of about 300.degree. F.Type: GrantFiled: June 1, 1982Date of Patent: August 30, 1983Assignee: Exxon Research & Engineering Co.Inventor: Terry S. King
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Patent number: 4324695Abstract: Transition metal carbonyl clusters intercalated with lamellar material such as graphite or smectites are prepared by reacting an intercalate of a transition metal halide with carbon monoxide at elevated temperature and at ambient to superatmospheric pressure. The intercalated complexes are useful in the catalysis of a variety of organic reactions including the water gas shift reaction, hydrogenation, hydroformylation, methanation, and so forth.Type: GrantFiled: November 17, 1980Date of Patent: April 13, 1982Assignee: National Distillers & Chemical Corp.Inventor: James A. Hinnenkamp
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Patent number: 4307248Abstract: Supported coprecipitated catalysts comprised of one or more metals of Group VIII, one or more metals of Group IIA, and aluminum are used for hydrogenating hydrogenatable organic compounds. The catalysts are produced by preparing, under agitation; an aqueous mixture containing ions of Group VIII, Group IIA, and aluminum, as well as solid porous particles to form a coprecipitate of the metal ions and aluminum ions with the solid porous support particles; heating the aqueous reaction mixture; and adding precipitating agent to precipitate the metal ions and aluminum ions onto the solid support.Type: GrantFiled: November 28, 1980Date of Patent: December 22, 1981Assignee: Exxon Research & Engineering Co.Inventors: Allan E. Barnett, Albert P. Halluin
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Patent number: 4273939Abstract: Supported coprecipitated non-ferrous Group VIII metal aluminum catalysts are used for hydrogenating hydrogenatable organic compounds. The catalysts are produced by preparing an aqueous mixture containing the metal ions, aluminum ions and solid porous support particles under agitation to form a coprecipitate of the metal ions and aluminum ions with the solid porous support particles; heating the aqueous reaction mixture; and adding precipitating agent to further precipitate the metal ions and aluminum ions onto the solid support.Type: GrantFiled: November 6, 1979Date of Patent: June 16, 1981Assignee: Exxon Research & Engineering Co.Inventors: Allan E. Barnett, Albert P. Halluin
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Patent number: 4263449Abstract: An alcohol is produced from a compound having an alkenyl group by a hydroformylation of said compound having an alkenyl group in a substantially water immiscible solvent in the presence of a hydroformylation catalyst which is soluble in said solvent and a hydrogenation of the reaction mixture in the presence of a hydrogenation catalyst.Water is added at a ratio of 0.5 to 30 times by weight base on an aldehyde produced by said hydroformylation before said hydrogenation, and an organic phase containing the hydroformylation catalyst component is separated from a water phase containing the alcohol produced by said hydrogenation and said organic phase is recycled into said hydroformylation.The compound having an alkenyl group is an aliphatic olefin, a hydroxyolefin, and olefin ether or an olefin ester and the corresponding saturated alcohol having one more carbon atom is produced.Type: GrantFiled: March 24, 1980Date of Patent: April 21, 1981Assignee: Toyoda Soda Manufacturing Co., Ltd.Inventors: Toshihiro Saito, Yukihiro Tsutsumi, Shoji Arai
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Patent number: 4225458Abstract: Contacting the saponified heavy oxygenated bottoms product obtained from an oxo distillation unit with demet water containing a cobaltous compound in a continuous flow, preferably countercurrent extractor results in the efficient production of an oil-soluble cobalt catalyst on a continuous basis.Type: GrantFiled: January 30, 1979Date of Patent: September 30, 1980Assignee: Exxon Research & Engineering Co.Inventors: I-Der Huang, Catherine McCooey
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Patent number: 4144191Abstract: Olefins are converted to alcohols by a one-step, hydroformylation process comprising contacting an olefin, such as 1-hexene, with a gaseous mixture of carbon monoxide and hydrogen in the presence of a catalyst prepared by loading a bimetallic cluster of the formula: Rh.sub.x Co.sub.y CO.sub.12 wherein both x and y are independently integers 1-3 with the proviso that .SIGMA. (x+y)=4, onto an amine resin, such as Dowex.RTM. MWA-1.Type: GrantFiled: June 6, 1977Date of Patent: March 13, 1979Assignee: The Dow Chemical CompanyInventors: George E. Hartwell, Philip E. Garrou