Preparing By Carbonylation (e.g., By Hydroformylation, Etc.) Patents (Class 568/909)
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Patent number: 4374277Abstract: Described are branched chain C.sub.11 aldehydes and alcohols, processes for producing same by (i) first dimerizing isoamylene(2-methyl-2-butene) to form a mixture of diisoamylenes and (ii) reacting the resulting mixture or separated components thereof with carbon monoxide and hydrogen by means of an oxo reaction, as well as methods for augmenting or enhancing the aroma of perfumes, colognes and perfumed articles by adding thereto perfume aroma augmenting or enhancing quantities of the thus produced C.sub.11 branched chain aldehydes and alcohol compositions of matter. Also described are perfume compositions, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, dryer-added fabric softener articles, hair preparations, deodorant compositions and bleaching compositions containing such products thus produced.Type: GrantFiled: September 25, 1981Date of Patent: February 15, 1983Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, John H. Geiger, Jr.
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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
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Patent number: 4374287Abstract: Alcohol may be synthesized by treating olefinic hydrocarbons with carbon monoxide and hydrogen in a hydroformylation zone utilizing a rhodium complex catalyst to effect the reaction. Following formation of the alcohol, the catalyst may be extracted from the alcohol by treatment with an aqueous ammonium hydroxide solution. Thereafter the aqueous ammonium hydroxide solution containing the catalyst is then stripped of ammonia by treatment with carbon monoxide or carbon monoxide containing gas. The aqueous ammonium hydroxide solution containing the rhodium complex catalyst is then stripped of a portion of water and the remaining solution is thereafter recycled to the hydroformylation zone.Type: GrantFiled: February 24, 1981Date of Patent: February 15, 1983Assignee: UOP Inc.Inventors: Tamotsu Imai, Edwin H. Homeier
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Patent number: 4370258Abstract: An improved hydroformylation process for preparing aldehydes by reacting olefins with synthesis gas (H.sub.2 and CO) under heating and pressure is disclosed. The hydroformylation is carried out in the presence of a platinum catalyst, and assistant composed of a halide of a metal of the group IVb of the Periodic Table and a reaction promotor composed of a specific bidentate ligand of the formula R.sub.2 X-Z-Y-Z-X-R'.sub.2. In this reaction, the platinum catalyst exerts a high activity, and an aldehyde mixture containing a linear isomer at a very high ratio of content is obtained as a product.Type: GrantFiled: May 7, 1981Date of Patent: January 25, 1983Assignee: Agency of Industrial Science & TechnologyInventors: Ikuei Ogata, Yasuziro Kawabata, Masato Tanaka, Teruyuki Hayashi
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Patent number: 4370504Abstract: A process for producing an aldehyde containing a perfluorocarbon group, which comprises hydroformylating an olefin containing a perfluorocarbon group represented by the general formula ##STR1## wherein R.sub.f represents a monovalent perfluorocarbon group, in the presence of a rhodium catalyst.Type: GrantFiled: March 4, 1981Date of Patent: January 25, 1983Assignee: Sagami Chemical Research CenterInventors: Iwao Ojima, Takamasa Fuchikami
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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
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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
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Patent number: 4361711Abstract: Olefins, carbon monoxide and hydrogen are catalytically reacted with rhodium catalysts to produce alcohols in a single step reaction.Type: GrantFiled: December 18, 1981Date of Patent: November 30, 1982Assignee: The Standard Oil CompanyInventors: M. W. Blaskie, J. R. Fox, F. A. Pesa
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Patent number: 4356334Abstract: Alcohols may be synthesized by reacting an olefinic hydrocarbon, carbon monoxide, and hydrogen in the presence of a catalyst comprising a rhodium carbonyl or organohodium complex and a promoter comprising ammonia at temperatures in the range of from about 50.degree. to about 250.degree. C. and a pressure in the range of from about 10 to about 300 atmospheres to produce the desired alcohol.Type: GrantFiled: February 20, 1981Date of Patent: October 26, 1982Assignee: UOP Inc.Inventor: Tamotsu Imai
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Patent number: 4348539Abstract: Heteronuclear-bridged rhodium clusters useful as catalysts in the hydroformylation of olefins.Type: GrantFiled: May 6, 1981Date of Patent: September 7, 1982Assignee: Union Carbide CorporationInventors: Ernst Billig, Jackie D. Jamerson, Roy L. Pruett
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Patent number: 4342838Abstract: This invention relates to new bimetallic cluster compounds of the formulaL.sub.2 M.sub.2 Ru.sub.6 C(CO).sub.16wherein L is RCN, R being C.sub.1 to C.sub.6 alkyl, C.sub.6 to C.sub.10 aralkyl or phenyl, and M is copper, silver or gold. These compounds are useful as homogeneous catalysts for converting synthesis gas to methanol.Type: GrantFiled: March 11, 1981Date of Patent: August 3, 1982Assignee: Exxon Research & Engineering Co.Inventors: Roy L. Pruett, John S. Bradley
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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
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Patent number: 4334042Abstract: In the carbonylation of olefinic compounds in the presence of a cobalt carbonyl catalyst, the addition to the reaction system of a secondary phosphine oxide represented by the general formula ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and each is substituted or unsubstituted hydrocarbon residue having not more than about 20 carbon atoms, in an amount of 0.2 to 20 moles per gram atom of the cobalt makes it possible to separate the reaction product from the reaction mixture by direct distillation without any such special operation for the catalyst separation as required in the conventional processes. The distillation residue which contains the catalyst can be recycled for the reuse thereof in the carbonylation.Type: GrantFiled: July 23, 1979Date of Patent: June 8, 1982Assignee: Kuraray Co. Ltd.Inventors: Mitsuo Matsumoto, Masuhiko Tamura
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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
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Patent number: 4329511Abstract: In hydroformylating an olefinic compound to produce an aldehyde derivative thereof employing as catalyst a complex of a Group VIII metal and an organic ligand dissolved in an inert liquid reaction solvent with the aldehyde product being continuously stripped out of the solvent, stripping is facilitated while by-product formation is kept at a minimum by using a solvent of specially-chosen high molecular weight while also controlling the degree of stripping as desired to maintain in the reaction medium a controlled molar concentration of the aldehyde hydroformylation product.Type: GrantFiled: June 23, 1980Date of Patent: May 11, 1982Assignee: Celanese CorporationInventors: Edward B. Hackman, Larry D. Zeagler, James S. McLaughlin, Carl M. Peabody
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Patent number: 4329521Abstract: Alcohols may be synthesized by treating an olefinic hydrocarbon with carbon monoxide and hydrogen in a hydroformylation zone using a rhodium complex catalyst and an amine modifier to effect the reaction. Following the formation of the alcohol, a catalyst may be extracted from said alcohol by treatment with an aqueous ammonium hydroxide solution. Following this, the aqueous ammonium solution containing the rhodium catalyst is subjected to an extraction process utilizing the amine modifier as the extractant and thereafter recycling the rhodium complex catalyst and amine modifier to the hydroformylation zone.Type: GrantFiled: March 3, 1981Date of Patent: May 11, 1982Assignee: UOP Inc.Inventors: Edwin H. Homeier, Tamotsu Imai, David E. Mackowiak, Catherine E. Guzolek
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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
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Patent number: 4320237Abstract: Method for the hydroformylation of olefins with carbon monoxide and hydrogen in the presence of soluble cobalt compounds as the catalyst at an elevated temperature and under increased pressure, and optionally in the presence of paraffins and/or other inert diluents. The hydroformylation is conducted, in a first stage, up to a conversion of about 40-75 percent with remixing of the reaction mixture, and then, in a second stage, up to a conversion of at least 95 percent, preferably 95-98 percent, without remixing.Type: GrantFiled: April 7, 1978Date of Patent: March 16, 1982Assignee: Chemische Werke Huls AGInventors: Manfred Kaufhold, Johann Gaube
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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
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Patent number: 4312779Abstract: Metal catalyst complexes such as those containing a metal of Group VIII of the Periodic Table which have been used in organic reactions such as the hydroformylation of olefins to form alcohols may be recovered from the product alcohols by treating said alcohol with anhydrous gaseous ammonia at temperatures in the range of from about 0.degree. to about 100.degree. C. and pressures in the range of from about 5 to about 1000 psi to precipitate the solution catalyst complex and thereby enable the separation of the catalyst complex from the product to be accomplished in a relatively simple manner.Type: GrantFiled: September 25, 1980Date of Patent: January 26, 1982Assignee: UOP Inc.Inventor: Michael H. Quick
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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
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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
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Patent number: 4298499Abstract: Metallic catalysts such as Group VIII metal complexes which are used in hydroformylation reaction for the production of alcohols from olefins will be found in the product mixture. The separation and recovery of these metal catalysts from the product mixture may be accomplished by treating said product mixture with a biphyllic ligand capable of forming a soluble complex with the metallic catalyst and thus can be removed from the desired product.Type: GrantFiled: July 14, 1980Date of Patent: November 3, 1981Assignee: UOP Inc.Inventor: Tamotsu Imai
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Patent number: 4292196Abstract: Catalysts which comprise metal carbonyls or organometallic complexes in which the metal portion of the complex is selected from a Group VIII metal are useful in hydroformylation reactions. The catalysts which are homogeneous in nature may be recovered from the hydroformylation products by treating the catalyst complex with a nitrogen-containing compound in an aqueous phase whereby said catalyst may be easily separated from the hydroformylation products and recovered.Type: GrantFiled: December 10, 1979Date of Patent: September 29, 1981Assignee: UOP Inc.Inventors: Edwin H. Homeier, Alan R. Dodds, Tamotsu Imai
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Patent number: 4275252Abstract: Alcohol may be synthesized from olefinic hydrocarbons by treating the hydrocarbon with carbon monoxide and hydrogen in a hydroformylation zone using a rhodium complex catalyst to effect the reaction. Following formation of the alcohol, the catalyst may be extracted from the alcohol by treatment with an aqueous ammonium hydroxide solution. The aqueous ammonium hydroxide solution containing the catalyst is then stripped of ammonia by treatment with a stripping agent such as carbon monoxide. A major portion of the alcohol is recovered while the remaining portion is used as an extractant to recover the rhodium complex catalyst from the aqueous ammonium hydroxide solution and thereafter is recycled to the hydroformylation zone.Type: GrantFiled: February 28, 1980Date of Patent: June 23, 1981Assignee: UOP Inc.Inventors: Tamotsu Imai, Edwin H. Homeier, David E. Mackowiak
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Patent number: 4262147Abstract: Dicyclopentadiene is selectively and substantially hydroformylated to its dimethanolic derivatives by a process comprising contacting dicyclopentadiene with a gaseous mixture of carbon monoxide and hydrogen at a temperature of at least about 100.degree. C. and a pressure of at least about 1,000 psig in the presence of a catalytic amount of a catalyst consisting essentially of a rhodium-cobalt bimetallic cluster, such as Rh.sub.2 Co.sub.2 CO.sub.12, supported on an amine resin, such as DOWEX.RTM. MWA-1.Type: GrantFiled: March 16, 1979Date of Patent: April 14, 1981Assignee: The Dow Chemical CompanyInventors: Philip E. Garrou, George E. Hartwell
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Patent number: 4262142Abstract: In a rhodium-catalyzed hydroformylation process employing olefin reactants having from 3 to 20 carbon atoms to produce products rich in normal aldehydes, the efficiency of the catalyst in producing such products is substantially uneffected and propionaldehyde is also produced by employing ethylene as a coreactant along with the olefin.Type: GrantFiled: December 28, 1979Date of Patent: April 14, 1981Assignee: Union Carbide CorporationInventors: Paul D. Sherman, Jr., Stephen C. Winans, Dennis G. Morrell
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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
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Patent number: 4242283Abstract: An improved process for continuously producing oxygen-containing compounds by the oxo process from olefins, carbon monoxide and hydrogen at a pressure of 5 to 1000 bar and at a temperature of 50.degree. to 200.degree. C. in the presence of a metal of Group VIII and/or a compound thereof as catalyst is disclosed. According to the invention, the unreacted olefin carbon monoxide and hydrogen is passed to a high pressure reactor wherein unreacted olefin is reacted under oxo process conditions to form oxygen-containing compounds.Type: GrantFiled: October 13, 1978Date of Patent: December 30, 1980Assignee: Ruhrchemie AktiengesellschaftInventors: Josef Hibbel, Gunther Kessen, Josef Meis
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Patent number: 4229381Abstract: An improved hydroformylation process for preparing aldehydes by reacting olefins with synthesis gas (H.sub.2 and CO) under heating and pressure is disclosed. The hydroformylation is carried out in the presence of a platinum catalyst, and assitant composed of a halide of a metal of the group IVb of the Periodic Table and a reaction promotor composed of a specific bidentate ligand of the formula R.sub.2 X--Z--Y--Z--X--R'.sub.2. In this reaction, the platinum catalyst exerts a high activity, and an aldehyde mixture containing a linear isomer at a very high ratio of content is obtained as a product.Type: GrantFiled: March 9, 1979Date of Patent: October 21, 1980Assignee: Agency of Industrial Science & TechnologyInventors: Ikuei Ogata, Yasuziro Kawabata, Masato Tanaka, Teruyuki Hayashi
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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: 4224255Abstract: Oxygenated compounds are prepared by reacting olefinically unsaturated compounds with carbon monoxide and hydrogen in the presence of a hydroformylation catalyst with suppression of the olefin hydrogenation side reaction if an acid is used in the reaction mixture. Typically, o-phthalic acid suppresses the formation of hexane and n-propanol, respectively, when 1-hexene and allyl alcohol are hydroformylated.Type: GrantFiled: June 15, 1978Date of Patent: September 23, 1980Assignee: General Electric CompanyInventor: William E. Smith
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Patent number: 4221744Abstract: An improved process for hydroformylating an ethylenically-unsaturated compound to form an aldehyde derivative thereof in the presence of rhodium hydridocarbonyl in complex combination with an organic ligand, characterized by employing as said organic ligand a compound having two phosphino moieties, one being of the formula: ##STR1## and the other being of the formula: ##STR2## wherein R.sub.1, R.sub.2, R.sub.1 ', and R.sub.2 ' are organic radicals at least one of which contains an electronegative substituent moiety. The presence of the electronegative substituent in the ligand leads to an increased ratio of linear aldehyde to branched-chain aldehyde in the hydroformylation reaction product.Type: GrantFiled: December 1, 1978Date of Patent: September 9, 1980Assignee: Celanese CorporationInventor: Jerry D. Unruh
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Patent number: 4219684Abstract: Alcohols may be synthesized by reacting an olefinic compound, carbon monoxide and hydrogen in the presence of a Group VIII organometallic complex catalyst at reaction conditions which include a temperature in the range of from about 50.degree. to about 250.degree. C. and a pressure in the range of from about 10 to about 300 atmospheres. In addition, the reaction is also effected in the presence of a promoter compound comprising a nitrile.Type: GrantFiled: April 2, 1979Date of Patent: August 26, 1980Assignee: UOP Inc.Inventor: Tamotsu Imai
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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
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Patent number: 4213921Abstract: Organic compound conversion in the presence of a new class of heterogeneous catalyst is provided. Said new class of heterogeneous catalyst comprises a substrate having a minimum surface area of about 10 m.sup.2 /g and having pores with a minimum pore diameter of about 5 Angstrom Units, said substrate being modified by at least one amine functional member coordinated to a metal function, said amine functional member acting as a bridging member between said substrate and said metal function.Type: GrantFiled: November 22, 1976Date of Patent: July 22, 1980Assignee: Mobil Oil CorporationInventors: Thomas O. Mitchell, Darrell D. Whitehurst
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Patent number: 4210426Abstract: A process for recovering propene and propene/propane mixtures from the off-gases obtained from the hydroformylation of propene involves contacting the off-gases with a liquid absorbent comprising at least one of the liquid substances formed during the hydroformylation of propene to absorb the propene and propane and thereafter desorbing these gases from said liquid substances.Type: GrantFiled: November 7, 1978Date of Patent: July 1, 1980Assignee: Chemische Werke Huls AktiengesellschaftInventor: Srinivasan Sridhar
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Patent number: 4210608Abstract: Linear primary aldehydes and alcohols are produced from linear monoolefinic hydrocarbons. The monoolefinic hydrocarbon is treated in admixture with carbon monoxide and hydrogen and in contact with an aluminum catalyst and a Group VIII metal hydroformylation catalyst.Type: GrantFiled: December 8, 1975Date of Patent: July 1, 1980Assignee: UOP Inc.Inventor: Paul A. Pinke
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Patent number: 4209467Abstract: A hydroformylation process in which the catalyst is the reaction product of a cobalt carbonyl compound with a nitrogen-containing heterocyclic compound having an enolic hydroxyl group on the carbon atom adjacent to the ring-forming nitrogen atom or the catalyst is the reaction product of a .beta.-dioxo cobalt compound and a nitrogen-containing base having a double bonded carbon atom at the .alpha.-position, with carbon monoxide and hydrogen.Type: GrantFiled: January 2, 1979Date of Patent: June 24, 1980Assignee: Daicel Ltd.Inventors: Hidetaka Kojima, Shingo Oda, Takushi Yokoyama, Yasukazu Murakami
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Patent number: 4198353Abstract: A catalyst of the general structure P --M Cl.sub.3 wherein M is rhodium or iridium and P is a heterocyclic nitrogen-containing polymer has been found to be an effective heterogeneous hydroformylation catalyst at temperatures of from about 60.degree. to about 150.degree. C. and H.sub.2 /CO gas pressures of from about 300 to about 3500 psig for most primary and internal olefins, producing an increased amount of linear normal aldehydes. When the reactor gas is altered to hydrogen, the catalyst further converts aldehydes formed by hydroformylation to alcohols under the same reaction conditions. The catalyst is oxygen stable, heterogeneous, and easily recovered.Type: GrantFiled: December 26, 1978Date of Patent: April 15, 1980Assignee: Conoco, Inc.Inventor: John T. Carlock
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Patent number: 4197414Abstract: 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: October 18, 1978Date of Patent: April 8, 1980Assignee: The Dow Chemical CompanyInventors: George E. Hartwell, Philip E. Garrou
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Patent number: 4183872Abstract: 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: October 12, 1978Date of Patent: January 15, 1980Assignee: Conoco, Inc.Inventor: John T. Carlock
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Patent number: 4183871Abstract: Production of aldehydes and alcohols by hydroformylation of olefinically unsaturated compounds with carbon monoxide and hydrogen at elevated temperature and superatmospheric pressure in the presence of carbonyl complexes of metals of group 8 of the Periodic System which have been modified with trisubstituted phosphines in which two substituents are lower alkyl radicals and the third substituent is a higher aliphatic radical. Aldehydes and alcohols are known to be solvents; they are used on a large scale for the production of plasticizers for polyvinyl chloride.Type: GrantFiled: April 17, 1975Date of Patent: January 15, 1980Assignee: Badische Anilin-& Soda-Fabrik AktiengesellschaftInventors: Peter Tavs, Wilhelm Kniese, Hans Nienburg
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Patent number: 4179401Abstract: A process for heterogenizing a metal salt or organometallic complex catalyst of the type containing a group VIII metal comprising the steps of radiation grafting a monomer having a .alpha. unsaturated bond to a metal or an organic polymer and complexing a nitrogen, halogen or phosphorous containing group to the monomer with the metal salt or organometallic complex. The resultant catalysts being useful in the hydrogenation, hydroformylation, isomerization, cracking or dehydrogenation of organic molecules.Type: GrantFiled: July 11, 1977Date of Patent: December 18, 1979Inventors: John L. Garnett, Robert S. Kenyon
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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
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Patent number: 4142061Abstract: At a temperature in the range 100.degree. C to 225.degree. C the destructive dissociation of cobalt carbonyl compounds to cobalt metal and residue is inhibited by the action of one or more azoxy-dentated chelation ligands.Type: GrantFiled: December 12, 1977Date of Patent: February 27, 1979Assignee: Chevron Research CompanyInventor: John B. Wilkes
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Patent number: 4107079Abstract: Solid catalyst, insoluble in organic and aqueous solvents and having the general formula:A -- M (L').sub.n (L").sub.qin which A is an insoluble ligand, M is a Group VIII noble metal, L' and L" are ligands and n and q are intergers of 0 to 6 are provided for the advantageous catalysis of hydroformylation, and hydrogenation of olefins and the preparation of tertiary amines from olefins.Type: GrantFiled: January 26, 1977Date of Patent: August 15, 1978Assignee: Rhone-Poulenc IndustriesInventors: Yvonick Chevallier, Jacques-Pierre Martinaud, Francois Meiller, Jean Berthoux