Preparing By Carbonylation (e.g., By Hydroformylation, Etc.) Patents (Class 568/909)
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Patent number: 6225507Abstract: A process for the preparation of aldehydes or aldehydes and alcohols by hydroformylation of olefins containing more than 3 carbon atoms, comprising a hydroformylation stage, in which the olefin is hydroformylated under a pressure of form 50 to 1000 bar and at a temperature of from 50° to 180° C. by means of a rhodium catalyst dissolved in a homogenous reaction medium and a catalyst recovery stage comprising extraction of the rhodium catalyst with an aqueous solution of chelating agent, isolation of alcohols and/or aldehyde from the extracted hydroformylation product steam, precarbonylation of the aqueous rhodium-containing extract in the presence of carbon monoxide, synthesis gas as, or a gas mixture containing carbon monoxide under a pressure of from 50 to 1000 bar and at a temperature of from 50° to 180° C.Type: GrantFiled: August 4, 1998Date of Patent: May 1, 2001Assignee: BASF AktiengesellschaftInventors: Bernhard Giessler, Heinz-Josef Kneuper, Michael Röper, Rocco Paciello, Knut Oppenländer, Wolfgang Günther
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Patent number: 6222077Abstract: There is provided an alcohol composition obtained by dimerizing an olefin feed comprising C6-C10 linear olefins to obtain C12-C20 olefins, followed by conversion to alcohols, such as by hydroformylation. The composition has an average number of branches ranging from 0.9 to 2.0 per molecule. The linear olefin feed preferably comprises at least 85% of C6-C8-olefins. The primary alcohol compositions are then converted to anionic or nonionic surfactants, preferably sulfated or oxyalkylated or both. The sulfated compositions are biodegradable and possess good cold water detergency.Type: GrantFiled: April 2, 1998Date of Patent: April 24, 2001Assignee: Shell Oil CompanyInventor: David M. Singleton
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Patent number: 6191324Abstract: This invention relates in part to processes for producing one or more substituted or unsubstituted unsaturated alcohols which comprise reacting one or more substituted or unsubstituted alkadienes with carbon monoxide and hydrogen in the presence of a metal-ligand complex catalyst and a promoter and optionally free ligand to produce said one or more substituted or unsubstituted unsaturated alcohols. The substituted and unsubstituted unsaturated alcohols produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted unsaturated alcohols as principal product(s) of reaction.Type: GrantFiled: April 15, 1997Date of Patent: February 20, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Anil Sakharam Guram, John Robert Briggs, Kurt Damar Olson, Thomas Carl Eisenschmid, Diane Lee Packett, Erik Bruce Tjaden
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Patent number: 6187970Abstract: This invention relates in part to processes for producing one or more substituted or unsubstituted 1,6-hexanediols which comprise subjecting one or more substituted or unsubstituted penten-1-ols to reductive hydroformylation in the presence of a reductive hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce said one or more substituted or unsubstituted 1,6-hexanediols. The substituted and unsubstituted 1,6-hexanediols produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof, e.g., epsilon caprolactone. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted 1,6-hexanediols as principal product(s) of reaction.Type: GrantFiled: April 15, 1997Date of Patent: February 13, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: John Robert Briggs, Diane Lee Packett, David Robert Bryant, Ailene Gardner Phillips, David James Schreck, Anil Sakharam Guram, Kurt Damar Olson, Thomas Carl Eisenschmid, Eric Bruce Tjaden
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Patent number: 6184424Abstract: A process for the hydrogenation of reaction mixtures from the hydroformylation of C5 to C24 olefins using hydrogen on fixed catalysts at elevated temperature, in which the aldehydes, alcohols, formates and low-boilers are evaporated from the reaction mixture and passed in the vapor state over a support-free Cu/Cr catalyst.Type: GrantFiled: September 15, 1999Date of Patent: February 6, 2001Assignee: Oxeno Olefinchemie GmbHInventors: Wilfried Bueschken, Dietmar Gubisch
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Patent number: 6172269Abstract: This invention relates to processes for producing one or more substituted or unsubstituted 1,6-hexanediols, e.g., 1,6-hexanediol, which comprise subjecting one or more substituted or unsubstituted alkadienes to hydrocarbonylation in the presence of a hydrocarbonylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, and a promoter and optionally free ligand to produce said one or more substituted or unsubstituted 1,6-hexanediols. The substituted and unsubstituted 1,6-hexanediols produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof, e.g., epsilon caprolactone. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted 1,6-hexanediols as principal product(s) of reaction.Type: GrantFiled: April 15, 1997Date of Patent: January 9, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Anil Sakharam Guram, John Robert Briggs, Diane Lee Packett, Kurt Damar Olson, Thomas Carl Eisenschmid, Erik Bruce Tjaden
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Patent number: 6127432Abstract: This invention relates in part to a processes and catalysts for the conversion of a feedstock comprising carbon monoxide and hydrogen to a product stream comprising at least one of an ester, acid, acid anhydride and mixtures thereof. This invention also relates in part to processes and catalysts for converting an alcohol, ether and/or ether alcohol feedstock to oxygenated products, e.g., esters, acids, acid anhydrides and mixtures thereof. The processes and catalysts are especially suitable for the production of acetic acid and methyl acetate from a synthesis gas feedstock or from an alcohol, ether or ether alcohol feedstock.Type: GrantFiled: December 24, 1998Date of Patent: October 3, 2000Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Richard William Wegman, David Michael Minahan, William J. Bartley, Chinsoo Stephen Lee, David McNeill Somerville
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Patent number: 6103908Abstract: Nonaqueous ionic ligand liquids of the formula (Q.sup..sym.)a A.sup.a-, where Q.sup..sym. is a singly charged quaternary ammonium and/or phosphonium cation or the equivalent of a multiply charged ammonium and/or phosphonium cation and A.sup.a- is a sulfonated triarylphosphine, a process for preparing them and their use as catalyst constituents.Type: GrantFiled: December 16, 1998Date of Patent: August 15, 2000Assignee: Celanese GmbHInventors: Helmut Bahrmann, Markus Schulte
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Patent number: 6037506Abstract: A process is presented in which ethylenically unsaturated compounds are reacted with carbon monoxide and hydrogen to form reaction products. The reactants are contacted in the presence of a catalyst system made by combining: (a) a source of palladium, platinum, or nickel,(b) a bidentate ligand of the formula R.sub.1 R.sub.2 M.sub.1 RM.sub.2 R.sub.3 R.sub.4 in which M.sub.1 and M.sub.2 independently may be phosphorus, arsenic, or antimony atoms, R is a bivalent organic bridging group and R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are unsubstituted or substituted aliphatic groups, wherein one or more combinations of R.sub.1, R.sub.2, R.sub.3, and R.sub.4 form a bivalent cyclic group, and(c) an acid,and a promoter which is a formate, formic acid, or formic acid forming reagent provided that it is not an orthoformate.Type: GrantFiled: September 18, 1998Date of Patent: March 14, 2000Assignee: Shell Oil CompanyInventor: Cornelius Mark Bolinger
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Patent number: 6034286Abstract: This invention relates in part to processes for producing one or more substituted or unsubstituted saturated alcohols which comprise reacting one or more substituted or unsubstituted alkadienes with carbon monoxide and hydrogen in the presence of a metal-ligand complex catalyst and a promoter and optionally free ligand to produce said one or more substituted or unsubstituted saturated alcohols. The substituted and unsubstituted saturated alcohols produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted saturated alcohols as principal product(s) of reaction.Type: GrantFiled: October 16, 1997Date of Patent: March 7, 2000Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Anil Sakharam Guram, John Robert Briggs, Kurt Damar Olson, Thomas Carl Eisenschmid, Diane Lee Packett, Erik Bruce Tjaden
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Patent number: 6013816Abstract: Process for the preparation of a linear .omega.-formyl-carboxylic acid or a corresponding linear formylnitrile compound starting from an internally unsaturated C.sub.4 -C.sub.12 carboxylic acid or a corresponding ester or nitrile by means of hydroformylation in the presence of carbon monoxide, hydrogen and a catalyst system, wherein the hydroformylation is carried out in an aqueous medium and in that the catalyst system comprises platinum and a water-soluble organic bidentate ligand.Type: GrantFiled: July 5, 1996Date of Patent: January 11, 2000Assignee: DSM NVInventors: Onko J. Gelling, Imre Toth
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Patent number: 5998685Abstract: A highly flexible process for preparing butene oligomers from field butanes. The process can be controlled to produce the desired oligomerization products by appropriate selection of the starting materials.Type: GrantFiled: July 24, 1997Date of Patent: December 7, 1999Assignee: Huels AktiengesellschaftInventors: Franz Nierlich, Paul Olbrich, Wilhelm Droste, Richard Mueller, Walter Toetsch
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Patent number: 5962744Abstract: A process comprising subjecting at least one compound containing at least one carbon--carbon double bond or at least one carbon--carbon triple bond, hydrogen and carbon monoxide, to a hydrocarbonylation reaction in supercritical carbon dioxide, in the presence of a Group VIII transition metal catalyst precursor, and a phosphite ligand.Type: GrantFiled: March 27, 1998Date of Patent: October 5, 1999Assignees: The Research Foundation of State University of New York, Mitsubishi Chemical CorporationInventors: Iwao Ojima, Hisao Urata
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Patent number: 5856585Abstract: Process of catalytic partial oxidation of natural gas in order to obtain synthesis gas and formaldehyde, integrated with processes of hydrogenation of the resulting CO, such as Fischer-Tropsch and methanol syntheses. Such an oxidation is carried out by means of a catalyst constituted by one or more compounds of metals form Platinum Group, which is given the shape of wire meshes, or is deposited on a carrier made from inorganic compounds, in such a way that the level of metal or metals from Platinum Group, as percent by weight, is comprised within the range of from 0.1 to 20% of the total weight of catalyst and carrier, by operating at temperatures comprised within the range of from 300.degree. to 950.degree. C., under pressures comprised within the range of from 0.5 to 50 Atm, at space velocities comprised within the range of from 20,000 to 1,500,000 h.sup.-1.Type: GrantFiled: August 8, 1994Date of Patent: January 5, 1999Assignee: Snamprogetti S.p.A.Inventors: Domenico Sanfilippo, Luca Basini, Mario Marchionna
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Patent number: 5849960Abstract: There is provided a new branched primary alcohol composition and the sulfates thereof exhibiting good cold water detergency and biodegradability. The branched primary alcohol composition has an average number of branches per chain of at least 0.7, having at least 8 carbon atoms and contianing both methyl and ethyl branches. The primary alcohol composition may also contain less than 0.5 atom % of quaternary carbon atoms, and a significant number ethyl branches, terminal isopropyl branches, and branching it the C.sub.3 position relative to the hydroxyl carbon. The process for its manufacture is by skeletally isomerizing an olefin feed having at least 7 carbon atoms followed by conversion to an alcohol, as by way of hydroformylation, and ultimately, sulfation to obtain a detergent surfactant. Useful catalysts include the zeolites having at least one channel with a crystallographic free diameter along the x and/or y planes of the ?001! view ranging from greater than 4.2 .ANG. and less than 7 .ANG.Type: GrantFiled: November 26, 1996Date of Patent: December 15, 1998Assignee: Shell Oil CompanyInventors: David M. Singleton, Louis Kravetz, Brendan Dermot Murray
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Patent number: 5840993Abstract: The invention relates to cobalt carbonyl catalysts of the formula (I) ##STR1## where R is --CH(CH.sub.2 OCH.sub.2 CH.sub.3).sub.2 or --C.sub.2 H.sub.4 (OCH.sub.2 CH.sub.2).sub.n OY, with n=1 to 12 and Y=H or CH.sub.3, and also a process for their preparation and their use as hydroformylation catalysts.Type: GrantFiled: February 26, 1998Date of Patent: November 24, 1998Assignee: Hoechst AGInventors: Uwe Ritter, Norbert Winkhofer, Herbert Roesky
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Patent number: 5780694Abstract: There is provided an alcohol composition obtained by dimerizing an olefin feed comprising C.sub.6 -C.sub.10 linear olefins to obtain C.sub.12 -C.sub.20 olefins, followed by conversion to alcohols, such as by hydroformylation. The composition has an average number of branches ranging from 0.9 to 2.0 per molecule. The linear olefin feed preferably comprises at least 85% of C.sub.6 -C.sub.8 -olefins. The primary alcohol compositions are then converted to anionic or nonionic surfactants, preferably sulfated or oxyalkylated or both. The sulfated compositions are biodegradable and possess good cold water detergency. The process for making the dimerized primary alcohol comprises dimerizing, in the presence of a homogeneous dimerization catalyst under dimerization conditions, an olefin feed comprising C.sub.6 -C.sub.10 olefins and preferably at least 85 weight % of linear olefins based on the weight of the olefin feed, to obtain a C.sub.12 -C.sub.20 ; optionally double bond isomerizing said C.sub.12 -C.sub.Type: GrantFiled: November 26, 1996Date of Patent: July 14, 1998Assignee: Shell Oil CompanyInventor: David M. Singleton
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Patent number: 5703133Abstract: The invention provides for a method of making isoalcohols using syngas-to-alcohol catalyst and method of making it. The catalyst is a highly dispersed, alkali promoted, La stabilized, microcrystalline Cu.sub.2 O having a particle size of .ltoreq.6 nm in the presence of an alumina structural promoter, wherein on a mole % alkali free metals-only basis Cu is present in from 45 to 55%, Zn from 10 to 20%, Al from 10 to 25%, La from 5 to 15%, and wherein the alkali is from 0.01 to 0.91% K and from 3 to 6.5% Cs. The method of making it involves coprecipitation at a constant pH from a solution of soluble metal salts of copper, zinc, lanthanum and aluminum with an alkali hydroxide, washing the coprecipitate in the essential absence of CO.sub.2, drying and calcining it, then contacting it with K and Cs to form the promoted catalyst. The promoted catalyst is dried and recalcining to produce a catalyst precursor with highly dispersed CuO crystallites. The catalyst is activated in flowing hydrogen.Type: GrantFiled: December 8, 1995Date of Patent: December 30, 1997Assignee: Exxon Research and Engineering CompanyInventors: Thomas Henry Vanderspurt, Russell John Koveal
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Patent number: 5659090Abstract: The invention concerns steps in a process for the synthesis of at least one alkyl tertiobutyl ether, preferably respectively MTBE or ETBE, from at least one alcohol and from isobutene, each synthesized at least partially from natural gas. The alcohol, preferably methanol or ethanol respectively, is synthesized at least partially from synthesis gas, a portion of said synthesis gas being prepared in a natural gas steam prereforming zone. The isobutene is synthesized in a series of processes which includes direct transformation of natural gas to ethylene, known as oxidative coupling of methane (OCM), dimerisation of ethylene to normal butene, isomerisation of n-butene to isobutene, and the separation units associated therewith.Type: GrantFiled: October 19, 1995Date of Patent: August 19, 1997Assignees: Institut Francais Du Petrole, Elf Aquitaine ProductionInventors: Charles Cameron, Patrick Chaumette, Quang Dang Vu, Jacques Bousquet, Jacques Tournier-Lasserve, Guy Desgrandchamps
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Patent number: 5530168Abstract: A process is set forth for the synthesis of a C.sub.2 + aliphatic alcohol from hydrogen and carbon oxides in the presence of a copper-based catalyst which has been impregnated with an alkali metal compound. The process differs from the prior art in that the catalyst is impregnated with the alkali metal compound in the same slurry reactor which is used for reacting the hydrogen and carbon oxides. By contrast, in the prior art C.sub.2 + aliphatic alcohol synthesis, impregnation of the copper-based catalyst with the alkali metal compound is accomplished by a separate step in a separate vessel. By eliminating this separate step, the present invention realizes a savings in processing and equipment costs.Type: GrantFiled: October 3, 1994Date of Patent: June 25, 1996Assignee: Air Products and Chemicals, Inc.Inventors: Richard P. Underwood, Bernard A. Toseland, Thomas A. Dahl, Janet F. Hugo
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Patent number: 5468419Abstract: A C.sub.9 alcohol mixture for plasticizer obtained by the hydroformylation and hydrogenation of a C.sub.8 olefin mixture as the starting material obtained by the dimerization of a butene fraction, said alcohol mixture comprising from 8 to 50% by weight of a first group component having a retention time not longer than the retention time of isobutyl n-caprylate, from 8 to 40% by weight of a second group component having a retention time longer than that of isobutyl n-caprylate and not longer than that of methyl n-caprate and from 20 to 80% by weight of a third group component having a retention time longer than that of methyl n-caprate, as divided into such three components by gas chromatography using a capillary column packed with a polyethylene glycol having a number average molecular weight of 15,000 to 20,000 as an isomer separating agent.Type: GrantFiled: August 5, 1991Date of Patent: November 21, 1995Assignee: Mitsubishi Chemical CorporationInventors: Chihiro Miyazawa, Souichi Orita, Akio Tsuboi
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Patent number: 5406006Abstract: Carbonaceous 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 an aqueous cobalt salt solution in the presence of a light alcohol having from about 4 to 7 carbon atoms and syn gas prior to exposure to or processing with any other organic stream at a temperature of about 120.degree. C. to 190.degree. C. and a pressure of about 13 MPa to 32 MPa for about 2 to 50 hours.Type: GrantFiled: May 24, 1994Date of Patent: April 11, 1995Assignee: Exxon Chemical Patents IncInventors: Ronald R. Hill, Patricia B. Roussel
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Patent number: 5304675Abstract: An ester product consisting essentially of the acylation product of a mixture of near linear aliphatic 1-alkanols, said alkanols containing six to twenty carbon atoms and having a methyl to methylene branch ratio less than 0.25. These novel esters can be further converted to valuable 1-alkenes by pyrrolysis. In the preferred embodiments, esters are derived by acylation of C.sub.9 -C12 1-alkanols having a methyl to methylene branch ratio less than 0.18.In the preferred method of synthesizing the esters, acylation is carried out using aliphatic carboxylic acid, anhydride, halide or ester as acylating agent, wherein the agent has 2 to 20 carbon atoms. For instance, the acylating agent may comprise acetic anhydride and to produce acetate esters.Type: GrantFiled: December 11, 1990Date of Patent: April 19, 1994Assignee: Mobil Oil CorporationInventor: Catherine S. H. Chen
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Patent number: 5245072Abstract: This invention relates to processes for making biodegradable surfactant. The process comprises several steps including an optional step. The first step is directed to reacting olefins with ZSM-23 catalyst to form oligomers having the formula -(C.sub.3).sub.x, (C.sub.4).sub.x or mixtures thereof. Second, the oligomer is hydroformylated to form a saturated alcohol, for example, tridecanol. Next, the saturated alcohol is ethoxylated. Thereafter a nonionic biodegradable surfactant is recovered. This surfactant can be used in detergent formulations. A process is also taught for making esters which can be used as lubricants or plasticizers. A specific hydroformylation process is taught which utilizes modified cobalt carbonyl catalyst. Also, a specific ethoxylation process is taught. Products formed according to the latter two processes as well as their uses are also taught.Type: GrantFiled: February 24, 1992Date of Patent: September 14, 1993Assignee: Mobil Oil CorporationInventors: Thomas J. Giacobbe, George A. Ksenic
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Patent number: 5198589Abstract: A method of olefin hydroformylation is provided wherein an olefin reacts with a carbonyl catalyst and with reaction gases such as hydrogen and carbon monoxide in the presence of a supercritical reaction solvent, such as carbon dioxide. The invention provides higher yields of n-isomer product without the gas-liquid mixing rate limitation seen in conventional Oxo processes using liquid media.Type: GrantFiled: April 28, 1992Date of Patent: March 30, 1993Assignee: The United States of America as represented by the United States Department of EnergyInventors: Jerome W. Rathke, Robert J. Klingler
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Patent number: 5189105Abstract: A C.sub.9 alcohol mixture used to make a plasticizer obtained by the hydroformylation and hydrogenation of a C.sub.8 olefin mixture as the starting material obtained by the dimerization of a butene fraction, said alcohol mixture comprising from 8 to 50% by weight of a first group component having a retention time not longer than the retention time of isobutyl n-caprylate, from 8 to 40% by weight of a second group component having a retention time longer than that of isobutyl n-caprylate and not longer than that of methyl n-caprate and from 20 to 80% by weight of a third group component having a retention time longer than that of methyl n-caprate, as divided into such three components by gas chromatography using a capillary column packed with a polyethylene glycol having a number average molecular weight of 15,000 to 20,000 as an isomer separating agent.Type: GrantFiled: August 1, 1991Date of Patent: February 23, 1993Assignee: Mitsubishi Chemical Industries LimitedInventors: Chihiro Miyazawa, Souichi Orita, Akio Tsuboi
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Patent number: 5130107Abstract: Cobalt is recovered from the oil/water mixed reaction product of oxonation by increasing the carbon dioxide level in the reaction product and adjusting the temperature to enhance the carbon dioxide level in the oil water phase to promote the formation of cobalt carbonate which is allowed to settle and may be removed and/or recycled increasing cobalt utilization and reducing environmental problems.Type: GrantFiled: December 21, 1990Date of Patent: July 14, 1992Assignee: Exxon Chemical Patents Inc.Inventors: Nicolaas A. De Munck, Mattheus D. Olijve, Raf Caers, Arie Van Vliet, Jean A. A. Hanin, Eddy Van Driessche
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Patent number: 5112519Abstract: This invention relates to processes for making biodegradable surfactant. The process comprises several steps including an optional step. The first step is directed to reacting olefins with ZSM-23 catalyst to form oligomers having the formula (C.sub.3).sub.x, (C.sub.4).sub.x or mixtures thereof. Second, the oligomer is hydroformylated to form a saturated alcohol, for example, tridecanol. Next, the saturated alcohol is ethoxylated. Thereafter a nonionic biodegradable surfactant is recovered. This surfactant can be used in detergent formulations. A process is also taught for making esters which can be used as lubricants or plasticizers. A specific hydroformylation process is taught which utilizes modified cobalt carbonyl catalyst. Also, a specific ethoxylation process is taught. Products formed according to the latter two processes as well as their uses are also taught.Type: GrantFiled: June 5, 1989Date of Patent: May 12, 1992Assignee: Mobil Oil CorporationInventors: Thomas J. Giacobbe, George A. Ksenic
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Patent number: 5113022Abstract: This invention relates to novel ionic phosphites and the use thereof as ligands in homogenous transition metal catalyzed processes, especially hydroformylation.Type: GrantFiled: August 8, 1991Date of Patent: May 12, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Anthony G. Abatjoglou, David R. Bryant
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Patent number: 4908477Abstract: Organic iodine compounds are separated from carbonylation products of methanol, methyl acetate and dimethyl ether and from mixtures of such carbonylation products by a process wherein the iodine compounds are removed by liquid phase extraction with a non-aromatic hydrocarbon.Type: GrantFiled: March 9, 1987Date of Patent: March 13, 1990Assignee: BASF AktiengesellschaftInventors: Horst Hartmann, Waldhelm Hochstein, Gerd Kaibel, Franz-Josef Mueller
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Patent number: 4900462Abstract: A polar lubricating fluid comprising aliphatic molecules having hydroxy or ester functional groups. The alcohol lubricant molecules have at least 20 carbon atoms and the ester molecule comprises between 26 and 100 carbon atoms. The oxygenate content of both molecules is at least 0.2 mmoles per gram of lubricant. The alcohol lubricating fluid is produced by a process comprising hydroformylating olefins having at least 20 carbon atoms in the presence of a hydroformylating catalyst and synthesis gas comprising H.sub.2 and CO. The ester lubricating fluid is produced by a subsequent acylation. The reaction is carried out between 150.degree. C. and 300.degree. C.Type: GrantFiled: January 13, 1988Date of Patent: February 13, 1990Assignee: Mobil Oil Corp.Inventors: Werner O. Haag, Robert E. Palermo
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Patent number: 4900850Abstract: It has been discovered in accordance with the present invention that a tertiary butyl alcohol/ditertiary butyl peroxide azeotrope may be recovered from a product containing tertiary butyl alcohol and ditertiary butyl perioxide by distilling the tertiary butyl alcohol product to obtain an overhead fraction containing substantially all of the ditertiary butyl peroxide as a ditertiary butyl peroxide/tertiary butyl alcohol azeotrope and other contaminants.It has been further discovered in accordance with the present invention that the ditertiary butyl peroxide can be recovered from the distillate fraction by extraction with water (e.g., in a countercurrent water extraction tower) to provide a ditertiary butyl peroxide product of any desired degree of purity.Type: GrantFiled: December 23, 1986Date of Patent: February 13, 1990Assignee: Texaco Inc.Inventors: John R. Sanderson, Robert A. Meyer
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Patent number: 4782188Abstract: The invention is a process for the hydroformylation of C.sub.2-4 alkenes, formyl-substituted C.sub.2-4 alkenes, aryl-substituted alkenes, unsaturated norbornane ring-containing compounds, and .alpha.-unsaturated acetals which comprises contacting a C.sub.2-4 alkene, a formyl-substituted C.sub.2-4 alkene, aryl-substituted alkene, an unsaturated norbornane ring-containing compound or an .alpha.-unsaturated acetal in a polar organic solvent with water and carbon monoxide in the presence of a catalytic amount of a catalyst which comprises a mixture of (a) an alkali metal iron carbonyl or alkaline earth metal iron carbonyl which corresponds to the formula M.sub.a Fe.sub.x (CO).sub.y and (b) iron pentacarbonyl under conditions such that an alcohol or aldehyde derivative of a C.sub.2-4 alkene, a formyl-substituted C.sub.2-4 alkene, an aryl-substituted alkene, unsaturated norbornane ring-containing compound or an .alpha.Type: GrantFiled: November 14, 1983Date of Patent: November 1, 1988Assignee: The Dow Chemical CompanyInventor: Susan B. Butts
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Patent number: 4777320Abstract: A two step process for producing isobutylene from propylene and synthesis gas. In the first step, propylene is contacted with synthesis gas at elevated temperature in the presence of a catalyst system containing a mixture of monometal compounds M.sub.4 (CO).sub.12 and M'.sub.4 (CO).sub.12 and/or bimetal compound M.sub.2 M'.sub.2 (CO).sub.12 where M and M' are different metals of the cobalt group. The alcohol mixture thus-obtained is dehydrated in the second step, to produce a product fraction containing a large amount of isobutylene.Type: GrantFiled: March 17, 1987Date of Patent: October 11, 1988Assignee: Neste OyInventors: Leila Alvila, Tapani Pakkanen, Outi Krause, Matteus Joutsimo
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Patent number: 4711968Abstract: This invention is a catalytic process for the hydroformylation of olefinic, sulfur-containing thermally cracked petroleum streams to produce aldehydes and/or alcohols. The catalysts are homogeneous transition metal carbonyl complexes. Especially preferred catalysts for low and medium pressure hydroformylation are cobalt and rhodium carbonyl hydride complexes in which some of the carbonyl ligands have been replaced by trivalent phosphorus ligands. In a preferred high pressure hydroformylation, the sulfur-containing gas oil distillate feed is produced from vacuum residua by high temperature thermal cracking. Such a feed contains more than 20% olefins with 1-n-olefins as the single major types. These olefin components are hydroformylated in the presence of a cobalt carbonyl complex to produce a novel type of semilinear aldehyde or alcohol product containing an average of less than one alkyl branch per molecule.Type: GrantFiled: October 3, 1986Date of Patent: December 8, 1987Assignee: Exxon Research & Engineering Co.Inventors: Alexis A. Oswald, Ram N. Bhatia
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Patent number: 4710587Abstract: A process for selectively removing alkyl substituted phosphine from an organic liquid containing same and triarylphosphine by treating said liquid with phosphoric acid.Type: GrantFiled: August 2, 1985Date of Patent: December 1, 1987Assignee: Union Carbide Corp.Inventors: David R. Bryant, Richard A. Galley
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Patent number: 4678857Abstract: A process is disclosed for preparing products such as 4-hydroxybutanal which comprises contacting unsaturated compounds such as allyl alcohol with carbon monoxide and hydrogen in the presence of a rhodium carbonyl-phosphine catalyst and an aromatic solvent. The solvent is an aromatic which causes a large density difference between the resulting aqueous phase and organic phase so that the soluble rhodium catalyst can be easily separated from the 4-hydroxybutanal product and starting material without appreciable loss of the metal. This allows for easy recycle of the catalyst solution.Type: GrantFiled: March 31, 1986Date of Patent: July 7, 1987Assignee: Texaco Inc.Inventors: Roger G. Dureanleau, John F. Knifton
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Patent number: 4678860Abstract: A continuous thermochemical indirect liquefaction process to convert various biomass materials into diesel-type transportation fuels which fuels are compatible with current engine designs and distribution systems comprising feeding said biomass into a circulating solid fluidized bed gasification system to produce a synthesis gas containing olefins, hydrogen and carbon monoxide and thereafter introducing the synthesis gas into a catalytic liquefaction system to convert the synthesis gas into liquid hydrocarbon fuel consisting essentially of C.sub.7 -C.sub.17 paraffinic hydrocarbons having cetane indices of 50+.Type: GrantFiled: October 4, 1985Date of Patent: July 7, 1987Assignee: Arizona Board of RegentsInventor: James L. Kuester
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Patent number: 4658053Abstract: A process for the production of an ester comprises reacting an olefin with carbon monoxide, hydrogen and another ester at elevated temperature and pressure in the presence of a catalyst comprising (1) a rhodium source, (2) a ruthenium source, and (3) cobalt or zinc iodide. The product ester comprises the acid group of the ester used as reactant esterified with a hydrocarbyl group derived from the olefin, hydrogen and carbon monoxide.Type: GrantFiled: February 25, 1985Date of Patent: April 14, 1987Assignee: BP Chemicals LimitedInventor: Michael J. Green
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Patent number: 4652539Abstract: A catalyst for directly converting olefins to alcohols by hydroformylation in a single step, the catalys comprising a mixture of two monometal cluster compounds M.sub.4 (CO).sub.12 and M'.sub.4 (CO).sub.12 where M and M' are compounds of the cobalt group.Type: GrantFiled: November 22, 1985Date of Patent: March 24, 1987Assignee: Neste OYInventors: Leila Alvila, Outi Krause, Tapani Pakkanen, Matteus Joutsimo
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Patent number: 4625067Abstract: Cobalt values are removed from the crude product of a cobalt-catalyzed hydroformylation reaction by contacting the product with stripping gas to entrain volatile cobalt compounds, in the presence of water or aqueous acid to dissolve cobalt values not so entrained.Type: GrantFiled: November 27, 1985Date of Patent: November 25, 1986Assignee: Exxon Research & Engineering Co.Inventor: Jean A. A. Hanin
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Patent number: 4625068Abstract: Internal olefins are rapidly hydroformylated in high selectivity to aldehyde product using homogeneous rhodium catalysts modified with highly sterically hindered tricycloalkyl phosphine ligands under mild process conditions.Type: GrantFiled: March 20, 1985Date of Patent: November 25, 1986Assignee: Exxon Chemical Patents Inc.Inventor: David A. Young
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Patent number: 4612403Abstract: A process is provided for the hydroformylation of an olefinic compound with carbon monoxide and hydrogen in the presence of cobalt catalyst and a promoter comprised of an organic nitrile. In one aspect, the olefinic compounds are olefinic fatty compounds with at least 4 carbon atoms. In another aspect, the cobalt catalyst consists of only a soluble cobalt salt and a promoter consisting of an organic nitrile such as acetonitrile. In another aspect of the invention, the olefinic compound to be hydroformylated contains a cyano substituent such that the reaction is self promoted.Type: GrantFiled: June 20, 1985Date of Patent: September 16, 1986Assignee: Henkel CorporationInventor: Michael J. Virnig
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Patent number: 4605793Abstract: Described is a process for preparing at least one secondary alcohol of the class of methyl substituted pinyl hydroxy pentenes comprising the step of:(i) reacting alpha pinene or beta pinene with a mixture of carbon monoxide and hydrogen in the presence of a hydroformalation catalyst in order to produce at least one methyl substituted pinyl carboxyaldehyde;(ii) reacting the resulting methyl substituted pinyl carboxyaldehyde with methyl ethyl ketone in the presence of a basic catalyst; and(iii) reacting the resulting product with a reducing agent selected from the group consisting of alkali metal borohydrides and lithium aluminum hydride.Type: GrantFiled: July 13, 1984Date of Patent: August 12, 1986Assignee: International Flavors & Fragrances, Inc.Inventors: Braja D. Mookherjee, Robert W. Trenkle, Robin K. Wolff, Richard M. Boden, Takao Yoshida
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Patent number: 4590314Abstract: A process is disclosed for the production, selectively, of C.sub.n+1 alcohols from a C.sub.n olefin. The process comprises reacting the C.sub.n olefin with carbon monoxide and hydrogen in the presence of a catalyst consisting essentially of molybdenum sulfide and an alkali metal or alkaline earth metal compound.Type: GrantFiled: November 19, 1984Date of Patent: May 20, 1986Assignee: Union Carbide CorporationInventor: Nancy E. Kinkade
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Patent number: 4585891Abstract: Dihydrocarbyl oxalates are produced by reacting under substantially anhydrous conditions a dihydrocarbyl peroxide with carbon monoxide in the presence of a catalyst comprising a platinum group metal in compound or elemental form and a copper compound, optionally in the presence as promoter of a heterocyclic aromatic nitrogen compound.Type: GrantFiled: July 20, 1984Date of Patent: April 29, 1986Assignee: The British Petroleum Company P.L.C.Inventor: George E. Morris
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Patent number: 4584411Abstract: This invention relates to a process for improving the hydroformylation of Dimersol oligomers by first contacting the catalyst with a tantalum (V) halide/oxide-inorganic oxide catalyst before hydroformylating.Type: GrantFiled: February 25, 1985Date of Patent: April 22, 1986Assignee: Shell Oil CompanyInventor: Thomas H. Johnson
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Patent number: 4568653Abstract: Reaction mixtures which are obtained on hydroformylation or carbonylation of olefinically unsaturated compounds and which contain dissolved non-volatile complex compounds of metals of group VIII of the periodic table are worked up by a method wherein the products, after distillative removal of low-boiling constituents alone, or of these constituents plus a part of the high-boiling residue, or a part of the high-boiling residue after distillative removal of the desired products, are or is extracted with carbon dioxide, a C.sub.2 -C.sub.4 -paraffin, a C.sub.2 -C.sub.4 -olefin or a normally gaseous halohydrocarbon at above the critical temperature and above the critical pressure of these (extractant) compounds.Type: GrantFiled: January 6, 1981Date of Patent: February 4, 1986Assignee: BASF AktiengesellschaftInventors: Kurt Schwirten, Rudolf Kummer, Wolfgang Richter
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Patent number: 4567305Abstract: Allyl alcohol is hydroformylated with a gaseous mixture of hydrogen and carbon monoxide, in an aromatic hydrocarbon, in the presence of a rhodium complex and a trisubstituted phosphine, to form hydroxybutyraldehydes which are separated from the reaction mixture within an aqueous medium. The carbon monoxide partial pressure, the rate of consumption of carbon monoxide, the rate at which the carbon monoxide is dissolved in the reaction mixture, reaction temperature and the viscosity of the reaction mixture are selected and controlled in an interrelated way to give a high yield of 4-hydroxybutyraldehyde and reduced catalyst consumption.Type: GrantFiled: June 15, 1984Date of Patent: January 28, 1986Assignees: Kuraray Company, Ltd., Daicel Chemical Industries, Ltd.Inventors: Mitsuo Matsumoto, Shinichi Miura, Koichi Kikuchi, Masuhiko Tamura, Hidetaka Kojima, Kunio Koga, Shigeru Yamashita
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Patent number: 4547595Abstract: A method of reactivating anionic Group VIII hydroformylation catalysts to maintain high selectivity towards linear products. In the process of manufacturing aldehydes and alcohols from olefins, hydrogen, carbon monoxide and a catalyst, the selectivity for linear products is extremely high when an anionic Group VIII catalyst is used. This selectivity, after prolonged use of a catalyst, falls off along with the turnover number. The catalyst is reactivated to increase the selectivity towards linear products as well as the turnover number by subjecting the catalyst to a reducing agent which is strong enough under treatment conditions to reduce the anionic Group VIII catalyst. Reactivation of anionic iron, ruthenium, osmium, and mixed transition metal complex catalysts are particularly described and claimed.Type: GrantFiled: April 16, 1984Date of Patent: October 15, 1985Assignee: Ashland Oil, Inc.Inventor: Biau-Hung Chang