Including Hydroformylation Patents (Class 568/882)
-
Patent number: 4443638Abstract: A process for preparing alcohols from internal olefins is disclosed. Briefly, the process comprises (a) hydroformylation of internal olefins to aldehydes using a small amount of a ligand modified recycled rhodium catalyst, (b) separating the reaction product from the catalyst by flash vacuum distillation, (c) hydrogenating the aldehydes to form a product containing alcohols, and (d) removing impurities and recovering the desired alcohol product. An important feature of this process, centers around the use of internal olefins to make an alcohol product which has a large amount of linear alcohol and 2-methyl-branched alcohol in the product.Type: GrantFiled: April 19, 1982Date of Patent: April 17, 1984Assignee: Conoco, Inc.Inventor: James A. Yates
-
Patent number: 4435605Abstract: The invention is a process for the preparation of a 2-phenylethyl alcohol which comprises contacting an aromatic aldehyde with carbon monoxide and hydrogen in a solvent comprising an oxygenated polar hydrocarbon and water, in the presence of a catalytic amount of a catalyst comprising a cobalt compound, a ruthenium salt and an iodine salt, at elevated temperatures and a pressure of between 600 and 45,000 psi.Type: GrantFiled: August 27, 1982Date of Patent: March 6, 1984Assignee: The Dow Chemical CompanyInventors: Susan B. Butts, George E. Hartwell
-
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
-
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
-
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
-
Patent number: 4390729Abstract: Complexes of the formula[(R.sub.2 DQ).sub.b P.sup.+ R.sup.1.sub.4-b ].sub.g.(MX.sub.n).sub.sare disclosed in which R is selected from an alkyl group containing 1 to 30 carbon atoms and an aryl group containing from 6 to 10 carbon atoms; Q is a divalent organic radical selected from an alkylene group and an alkylene group the carbon chain of which is interrupted by an ether oxygen or phenylene group, wherein the alkylene group contains from 1 to 30 carbon atoms; R.sup.1 represents an alkyl group containing from 1 to 30 carbon atoms, wherein said R.sup.1 groups can be the same or different; D is a member selected from P and N; Z.sup.- is an anion; M is a Group VIII metal; X is an anion or organic ligand satisfying the coordination sites of the metal; b times g is 1 to 6; n is 2 to 6; and s is 1 to 3. Processes of using such complexes are also disclosed.Type: GrantFiled: November 3, 1980Date of Patent: June 28, 1983Assignee: Exxon Research and Engineering Co.Inventor: Alexis A. Oswald
-
Patent number: 4374999Abstract: Acrolein acetals are selectively hydroformylated on the unsaturated carbon atom adjacent to the carbon bearing two ether groups in the presence of a supported rhodium-cobalt bimetallic cluster. The resulting internally hydroformylated product is useful as a precursor of methacrylic acid.Type: GrantFiled: January 2, 1981Date of Patent: February 22, 1983Assignee: The Dow Chemical CompanyInventor: Philip E. Garrou
-
Patent number: 4374278Abstract: Hydroformylation mediums, and a process for producing same, which are derived from a rhodium complex concentrate, as well as a hydroformylation process for producing aldehydes which employs said concentrate as a source of rhodium for the rhodium complex catalyst of said process.Type: GrantFiled: July 15, 1981Date of Patent: February 15, 1983Assignee: Union Carbide CorporationInventors: David R. Bryant, Richard A. Galley
-
Patent number: 4361707Abstract: A process for selectively producing aldehydes, particularly acetaldehyde, which comprises introducing into a reaction zone (1) methanol, (2) carbon monoxide, (3) hydrogen, (4) cobalt, (5) iodine and (6) a specific phosphorus-containing ligand and then subjecting the contents of said reaction zone to an elevated temperature and an elevated pressure for a time sufficient to convert methanol to said aldehydes.Type: GrantFiled: August 3, 1981Date of Patent: November 30, 1982Assignee: Gulf Research & Development CompanyInventors: Mohammad M. Habib, Wayne R. Pretzer
-
Patent number: 4361706Abstract: A process for selectively producing aldehydes, particularly acetaldehyde, which comprises introducing into a reaction zone (1) methanol, (2) carbon monoxide, (3) hydrogen, (4) cobalt, (5) iodine and (6) a ligand containing atoms from Group VB of the Periodic Table separated by a sterically constrained carbon-carbon bond and then subjecting the contents of said reaction zone to an elevated temperature and an elevated pressure for a time sufficient to convert methanol to said aldehydes.Type: GrantFiled: August 3, 1981Date of Patent: November 30, 1982Assignee: Gulf Research & Development CompanyInventors: Mohammad M. Habib, Wayne R. Pretzer
-
Patent number: 4334101Abstract: Metal carbonyl clusters occluded in zeolites are prepared, to be used as catalyst in certain special reactions such as hydroformylation of diene hydrocarbons.Rhodium complexes are immobilized in certain zeolites and the catalyst thus obtained can be used as a heterogeneous catalyst.Type: GrantFiled: October 19, 1979Date of Patent: June 8, 1982Assignee: Snamprogetti S.p.A.Inventors: Elvio Mantovani, Nicola Palladino, Antonio Zanobi
-
Patent number: 4330678Abstract: A process for the hydroformylation of an olefin which comprises reacting an olefin with carbon monoxide and hydrogen in the process of a complex of rhodium with a compound of the formula:L(OR.sup.1)(OR.sup.2)(OR.sup.3)wherein L is P or As and R.sup.1, R.sup.2 and R.sup.3 are (dis)similar alkyl, aryl, alkaryl or aralkyl groups, provided that at least one of R.sup.1, R.sup.2 or R.sup.3 represents a group --CH.sub.n [CFXY].sub.3-n, wherein n is 1 or 2 and either(a) X and Y both represent F, or(b) one of X and Y represents F and the other represents H or Cl or an (un)substituted (ar)alkyl group, or(c) X represents H or Cl or an (un)substituted (ar)alkyl group and Y represents an (ar)alkyl group whose connecting carbon atom carries at least one F.Type: GrantFiled: December 8, 1980Date of Patent: May 18, 1982Assignee: Shell Oil CompanyInventors: Petrus W. N. M. Van Leeuwen, Cornelis F. Roobeek
-
Patent number: 4322564Abstract: A process for hydroformylation of olefins is described which comprises a step of reacting olefins with carbon monoxide and hydrogen in the presence of a Group VIII noble metal-triarylphosphine complex catalyst, an excess amount of triarylphosphine, a reaction solvent, and organic high boiling point by-products, taking out the produced aldehyde by separating from the resulted hydroformylation reaction product, and thereafter circulating the residual liquid containing the catalyst and the organic high boiling point by-products to the reaction system as a circulating catalyst liquid, wherein the improvement comprises withdrawing at least a part of said circulating catalyst liquid as an extracted catalyst liquid, distilling off at least a part of the organic high boiling point by-products by steam distillation of said extracted catalyst liquid, and recirculating the bottoms of the steam distillation tower to the hydroformylation reaction step.Type: GrantFiled: September 22, 1980Date of Patent: March 30, 1982Assignee: Mitsubishi Chemical Industries LimitedInventors: Yoshitoshi Tsunoda, Shimpei Tomita, Chihiro Miyazawa
-
Patent number: 4317936Abstract: The hydroformylation of olefinic hydrocarbons is effected by treating the hydrocarbon with hydrogen and carbon monoxide in the presence of a catalyst comprising an ion exchange resin, a metal selected from the group consisting of cobalt, ruthenium, palladium, platinium, and rhodium bound to said resin and an organic linking compound which has at least one moiety which is ionically bonded to said resin and which further has at least one moiety which is coordinately bonded to said metal.Type: GrantFiled: August 13, 1979Date of Patent: March 2, 1982Assignee: Shell Oil CompanyInventors: Leo Kim, Timm E. Paxson, Sunny C. Tang
-
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
-
Patent number: 4307255Abstract: Disclosed are novel cyclic terpenoid amines which can be prepared by cyclizing the corresponding acyclic terpenoid amine.Type: GrantFiled: March 14, 1980Date of Patent: December 22, 1981Assignee: SCM CorporationInventors: Bernard J. Kane, Richard A. Von Genk
-
Patent number: 4306084Abstract: The present invention is an isomerically specific improvement of the oxo process reaction. It comprises the reaction of an olefin with carbon monoxide and water or hydrogen in a basic solution in the presence of a ruthenium carbonyl catalyst to preferentially produce the next higher normal aldehyde, or alcohol.Type: GrantFiled: February 25, 1980Date of Patent: December 15, 1981Assignee: The University of TexasInventor: Rowland Pettit
-
Patent number: 4306085Abstract: The hydroformylation of olefinic hydrocarbons is effected by treating the hydrocarbon with hydrogen and carbon monoxide in the presence of a catalyst comprising an ion exchange resin and an organic linking compound having at least one resin-compatible moiety ionically bonded to said resin and further having at least one metal complexible moiety selected from the group consisting of cobalt, ruthenium, palladium, platinum and rhodium.Type: GrantFiled: August 13, 1979Date of Patent: December 15, 1981Assignee: Shell Oil CompanyInventors: Leo Kim, Timm E. Paxson, Sunny C. Tang
-
Patent number: 4299990Abstract: A process is described for preparing aldehyde by hydroformylation of olefins, in which the olefins together with carbon monoxide, hydrogen and paraffins are introduced into a solution of rhodium carbonyl-triphenylphosphine complexes as catalyst and phosphines as solvent, the improvement wherein the gas stream entering the catalyst solution contains 5 to 30% by volume of paraffins with 1 to 5 carbon atoms.Type: GrantFiled: June 30, 1980Date of Patent: November 10, 1981Assignee: Ruhrchemie AGInventors: Hans Tummes, Boy Cornils, Heinz Noeske
-
Patent number: 4291179Abstract: Acetaldehyde and ethanol are produced by the catalyzed reaction of formaldehyde, carbon monoxide and hydrogen using a halogen-containing rhodium catalyst.Type: GrantFiled: April 21, 1980Date of Patent: September 22, 1981Assignee: National Distillers and Chemical Corp.Inventors: Richard W. Goetz, Lawrence D. Meixsel, David W. Smith
-
Patent number: 4278819Abstract: Improved process for the production of acetaldehyde dimethyl acetal by reacting methanol with carbon monoxide and hydrogen in the presence of a cobalt-containing catalyst, halogen or a halide as promoter and a 3-valent phosphorus compound as ligand using a nickel compound as a co-catalyst.Type: GrantFiled: April 2, 1980Date of Patent: July 14, 1981Assignee: Union Rheinische Braunkohlen Kraftstoff AktiengesellschaftInventors: Joachim Korff, Max Fremery, Johannes Zimmermann
-
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
-
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
-
Patent number: 4255279Abstract: This invention relates to a process for dual demetalling of an oxo product contaminated with cobalt-containing catalyst residues and recovering catalytically active cobalt carbonyls which comprises treating the oxo product in a first zone with an aqueous solution of a cobalt salt of an organic or inorganic acid to extract cobalt carbonyl partially from the oxo product into the aqueous phase containing Co.sup.++ ions to form Co[Co(CO).sub.4 ].sub.2 therein and in a second zone substantially completing the demetalling of the thus treated oxo product by treatment with an aqueous organic or inorganic acid in the presence of air or oxygen to form a Co.sup.++ salt and using the resulting aqueous solution as feed to the first zone; subjecting the aqueous phase obtained from the first zone to preforming in a high pressure preformer under synthesis gas to convert any excess or residual Co.sup.++ salt contained in said aqueous phase to Co[Co(CO).sub.4 ].sub.Type: GrantFiled: July 20, 1979Date of Patent: March 10, 1981Assignee: Exxon Research & Engineering Co.Inventors: Ralph J. Spohn, Paul A. Ellsworth, John Lyford, IV
-
Patent number: 4226845Abstract: In the water gas shift reaction,H.sub.2 O+CO.fwdarw.H.sub.2 +CO.sub.2and more particularly in hydroformylation of olefins, e.g. ethylene ##EQU1## and in hydrohydroxymethylation in which an alcohol, e.g. propanol, is produced, higher yields and/or fewer by-products and branched chain products and/or faster reactions are obtained using a combination of two or more Group VIII metal carbonyls one of which is ruthenium.Type: GrantFiled: December 6, 1978Date of Patent: October 7, 1980Assignee: S R I InternationalInventor: Richard M. Laine
-
Patent number: 4214109Abstract: A catalyst having the structural formula ##STR1## wherein R is zero or an alkyl having from 1 to 10 carbon atoms and wherein P is a polystyrene polymer backbone, where the 6-member ring is part of the polymer. The catalyst is useful for converting olefins to aldehydes in high yield under reaction temperatures of from about 90.degree. to 140.degree. C. and pressures of about 300 to about 5000 psig in the presence of hydrogen and carbon monoxide yielding gases, and preferably polymer swelling solvents such as benzene, THF and toluene. The catalyst is also useful in hydrogenation reactions.Type: GrantFiled: January 29, 1979Date of Patent: July 22, 1980Assignee: Conoco, Inc.Inventor: John T. Carlock
-
Patent number: 4209652Abstract: A process for the simultaneous production of gasoline blending components and a phthalate ester useful as a plasticizer. C.sub.3 to C.sub.4 olefins are reacted in an oligomerization zone to form a mixture containing C.sub.6 to C.sub.10 olefinic hydrocarbons. A three carbon number boiling range intermediate fraction is recovered from this mixture. The less highly branched olefins in this intermediate fraction are selectively hydroformylated to yield alcohols which are then reacted with an aromatic carboxylic acid or an aromatic anhydride. The unhydroformylated olefins are combined with the other olefinic hydrocarbon fractions to form a high octane motor fuel.Type: GrantFiled: January 10, 1979Date of Patent: June 24, 1980Assignee: UOP Inc.Inventor: Dennis J. Ward