Including Hydroformylation Patents (Class 568/882)
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Patent number: 6228829Abstract: This invention relates to granular detergent products which include mid-chain branched surfactants.Type: GrantFiled: April 4, 2000Date of Patent: May 8, 2001Assignee: The Procter & Gamble CompanyInventors: Phillip Kyle Vinson, Thomas Anthony Cripe, Kenneth William Willman, Robert Emerson Stidham, Daniel Stedman Connor
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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: 6087309Abstract: This invention relates to a liquid cleaning composition comprising a surfactant system containing selected mid-chain branched surfactant and co-surfactants.Type: GrantFiled: November 4, 1999Date of Patent: July 11, 2000Assignee: The Procter & Gamble CompanyInventors: Phillip Kyle Vinson, Peter Robert Foley, Thomas Anthony Cripe, Daniel Stedman Connor
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Patent number: 6060443Abstract: Mixtures of mid-chain branched primary alkyl sulfate surfactants useful in cleaning compositions, especially for lower water temperature applications, alone or formulated with other surfactants for the purpose of modifying the low temperature cleaning properties of the cleaning formulations. The present invention also relates to novel mid-chain branched primary alkyl sulfate surfactants suitable for use in surfactant mixtures.Type: GrantFiled: October 13, 1998Date of Patent: May 9, 2000Assignee: The Procter & Gamble CompanyInventors: Thomas Anthony Cripe, Daniel Stedman Connor, Phillip Kyle Vinson, James Charles Theophile Roger Burckett-St. Laurent, Kenneth William Willman, Jeffrey Scott Dupont
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Patent number: 6051743Abstract: For the preparation of predominantly unbranched higher primary alcohols, olefins from the Fischer-Tropsch synthesis are reacted with hydrogen and carbon monoxide in the presence of water and a catalyst which is rhodium, in metallic form or as a compound, and a water-soluble phosphine. The reaction product obtained is hydrogenated. The water-soluble phosphines employed are compounds whose anion is a phosphine containing at least one sulfonated or carboxylated aromatic radical and whose cation is a quaternary ammonium or phosphonium ion.Type: GrantFiled: December 7, 1993Date of Patent: April 18, 2000Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Gregor Deckers, Wolfgang Greb, Peter Heymanns, Peter Lappe, Thomas Muller, Jurgen Szameitat, Ernst Wiebus
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Patent number: 6049011Abstract: A dilute ethylene stream, e.g., one produced by steam cracking, is oxonated to yield propanal, without the need to separate other lower hydrocarbons.Type: GrantFiled: October 15, 1997Date of Patent: April 11, 2000Assignee: Exxon Chemical Patents Inc.Inventors: Gabor Kiss, Michael G Matturro, Harry William Deckman, Frank Hershkowitz, David R. Lumgair, Jr., Gary F Janda, Daniel N King
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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: 6015928Abstract: A single-stage process is described that includes simultaneously, in a mixture containing an olefin; synthesis gas; a cobalt catalyst in an organic phase; and an aqueous cobalt salt solution; hydroformylating the olefin, and forming and extracting into the organic phase the cobalt catalyst from the aqueous cobalt salt solution. An apparatus is also described that includes a means for carrying out the process. The process is particularly suitable for preparing aldehydes and alcohols.Type: GrantFiled: December 15, 1997Date of Patent: January 18, 2000Assignee: Huels AktiengesellschaftInventors: Dietmar Gubisch, Klaus Armbrust, Alfred Kaizik, Bernhard Scholz, Rudolf Nehring
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Patent number: 6008181Abstract: Mid-chain branched primary alkyl alkoxylated sulfate surfactants useful in laundry and cleaning compositions, especially granular and liquid detergent compositions. These surfactant mixtures are also suitable for formulation with other surfactants for the purpose of providing improved surfactant systems, especially for use in detergent compositions which will be used in laundry processes involving low water temperature wash conditions. The present invention also relates to novel mid-chain branched primary alkyl alkoxylated sulfate surfactants suitable for use in the surfactant mixtures.Type: GrantFiled: October 13, 1998Date of Patent: December 28, 1999Assignee: The Procter & Gamble CompanyInventors: Thomas Anthony Cripe, Daniel Stedman Connor, Phillip Kyle Vinson, James Charles Theophile Roger Burckett-St. Laurent, Kenneth William Willman
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Patent number: 6005148Abstract: A supported catalyst comprising a support, an anchoring agent such as a heteropoly acid or anion, and a metal complex which is useful in a wide variety on organic reactions, especially the hydrogenation of substituted .alpha.,.beta. unsaturated acids and esters, is provided. Various methods of preparing the supported catalyst of the present invention is also disclosed.Type: GrantFiled: November 17, 1998Date of Patent: December 21, 1999Assignee: Seton Hall UniversityInventors: Setrak K. Tanielyan, Robert L. Augustine
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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: 5922921Abstract: Disclosed is the use of a Raney cobalt catalyst in the hydrogenation process for the production of n-butanol.A process for the production of purified n-butanol comprising contacting in a hydrogenation zone n-butyraldehyde and hydrogen with an active porous cobalt catalyst under hydrogenation conditions of temperature and pressure for the production of alcohols from aldehydes, either in the substantial absence of water, or in the presence of water in an amount up to about 6 wt % based on the weight of the liquid hydrogenation reaction product to produce said reaction product comprising n-butanol, and purifying said reaction product by fractional distillation in the presence of about 0.01 to about 6 wt % of water, based on the total weight of feed to the fractionating column.Type: GrantFiled: October 27, 1997Date of Patent: July 13, 1999Assignee: Celanese International CorporationInventors: Jerry D. Unruh, Debra A. Ryan, Shannon L. Dugan
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Patent number: 5877358Abstract: In the process of hydrogenating a crude aldehyde product formed from the oxo process into a crude alcohol product, which process includes: feeding the crude aldehyde product into a first reactor which contains a hydrogenation catalyst, thereby forming a first hydrogenated product; feeding the first hydrogenated product from the first reactor through at least one intermediate reactor, each intermediate reactor being connected in series and containing a hydrogenation catalyst, thereby forming at least one intermediate hydrogenated product; and feeding the intermediate hydrogenated product from a last intermediate reactor to a final reactor which contains a hydrogenation catalyst, thereby forming the crude alcohol product; the improvement including a step wherein: at least a portion of the first hydrogenated product is recycled to the first hydrogenation reactor; or at least a portion of the intermediate hydrogenated product is recycled to the first hydrogenation reactor or an intermediate reactor upstream of thType: GrantFiled: September 23, 1996Date of Patent: March 2, 1999Assignee: Exxon Chemical Patents Inc.Inventors: Ronald D. Garton, Donald Q. Brown, Magdiel Agosto
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Patent number: 5866725Abstract: A process for the production of purified n-propanol comprising contacting in a hydrogenation zone propionaldehyde and hydrogen with an active porous cobalt catalyst under hydrogenation conditions of temperature and pressure for the production of alcohols from aldehydes, either in the substantial absence of water, or in the presence of water in an amount up to about 3 wt % based on the weight of the liquid hydrogenation reaction product, to produce said reaction product comprising n-propanol, and purifying said reaction product by fractional distillation in the substantial absence of water, or in the presence of water in an amount up to about 3 wt % based on the total weight of feed to the fractionating column.Type: GrantFiled: December 11, 1997Date of Patent: February 2, 1999Assignee: Celanese International CorporationInventors: Jerry D. Unruh, Debra A. Ryan, Shannon L. Dugan
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Patent number: 5661204Abstract: Mixtures of isomeric decyl alcohols obtained by oligomerization of propylene in the presence of deactivated zeolites as catalysts, followed by separation of the nine carbon olefins from the oligomer mixture, then hydroformylation of the 9 carbon olefins to 10 carbon aldehydes, and hydrogenation of the aldehydes to the corresponding alcohols. The mixtures, when esterified with phthalic acid, or anhydride, provide a mixture of isomeric di-decyl phthalates that can be used as plasticizers.Type: GrantFiled: June 7, 1995Date of Patent: August 26, 1997Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Wolfgang Greb, Peter Heymanns, Peter Lappe, Thomas Muller, Jurgen Szameitat, Ernst Wiebus
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Patent number: 5600031Abstract: A process for preparing oxo alcohols and aldehydes by the cobalt catalyzed hydroformylation of C.sub.2 to C.sub.17 linear or branched monoolefins with subsequent hydrogenation of the hydroformylation product, in which oxo process aqueous solutions of cobalt salts are converted to active hydrido cobalt carbonyl species in a preformer reactor under preforming reaction conditions, the improvement characterized by the preformer reactor containing a shell-type, metal on substrate, preformer catalyst.Type: GrantFiled: August 18, 1995Date of Patent: February 4, 1997Assignee: Exxon Chemical Patents, Inc.Inventor: Patricia B. Roussel
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Patent number: 5583250Abstract: Mixtures of isomeric decyl alcohols obtained by oligomerization of propylene in the presence of deactivated zeolites as catalysts, followed by separation of the nine carbon olefins from the oligomer mixture, then hydroformylation of the 9 carbon olefins to 10 carbon aldehydes, and hydrogenation of the aldehydes to the corresponding alcohols. The mixtures, when esterified with phthalic acid, or anhydride, provide a mixture of isomeric di-decyl phthalates that can be used as plasticizers.Type: GrantFiled: June 7, 1995Date of Patent: December 10, 1996Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Wolfgang Greb, Peter Heymanns, Peter Lappe, Thomas M uller, J urgen Szameitat, Ernst Wiebus
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Patent number: 5545767Abstract: 1,3-propanediol is prepared in a process comprising the steps of:contacting ethylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of an effective amount of a non-phosphine-ligated cobalt catalyst and an effective amount of a lipophilic phenol at a temperature within the range of about 50.degree. to about 100.degree. C. and a pressure within the range of about 500 to about 5000 psig, under reaction conditions effective to produce an intermediate product mixture comprising less than about 15 wt % 3-hydroxypropanal;adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid at a temperature less than about 100.degree. C.Type: GrantFiled: September 30, 1994Date of Patent: August 13, 1996Assignee: Shell Oil CompanyInventors: Paul R. Weider, Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Thomas C. Semple
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Patent number: 5516948Abstract: Mixtures of isomeric decyl alcohols obtained by oligomerization of propylene in the presence of deactivated zeolites as catalysts, followed by separation of the nine carbon olefins from the oligomer mixture, then hydroformylation of the 9 carbon olefins to 10 carbon aldehydes, and hydrogenation of the aldehydes to the corresponding alcohols. The mixtures, when esterified with phthalic acid, or anhydride, provide a mixture of isomeric di-decyl phthalates that can be used as plasticizers.Type: GrantFiled: June 7, 1995Date of Patent: May 14, 1996Assignee: Hoechst AGInventors: Helmut Bahrmann, Wolfgang Greb, Peter Heymanns, Peter Lappe, Thomas Muller, Jurgen Szameitat, Ernst Wiebus
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Patent number: 5504261Abstract: A process for producing a hydroxy compounds such as butanol or butanediol by hydroformylation of an olefin using a precious metal and phosphorus compound catalyst system, water extraction of the aldehyde product and hydrogenation of the extracted aldehyde where the aqueous extract is treated with an ion exchange resin before hydrogenation to increase hydrogenation catalyst life.Type: GrantFiled: August 1, 1994Date of Patent: April 2, 1996Assignee: ARCO Chemical Technology, L.P.Inventors: Thomas C. Mullin, Nicholas Triantafillou
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Patent number: 5463144Abstract: 1,3-propanediol is prepared in a process comprising the steps of:contacting ethylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of an effective amount of a non-phosphine-ligated cobalt catalyst and an effective amount of a lipophilic quaternary ammonium salt at a temperature within the range of about 50.degree. to about 100.degree. C. and a, pressure within the range of about 500 to about 5000 psig, under reaction conditions effective to produce an intermediate product mixture comprising less than 15 wt % 3-hydroxypropanal;adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid at a temperature less than about 100.degree. C.Type: GrantFiled: September 30, 1994Date of Patent: October 31, 1995Assignee: Shell Oil CompanyInventors: Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Terry B. Thomason, Thomas C. Semple, Paul R. Weider, Juan P. Arhancet
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Patent number: 5463145Abstract: 1,3-Propanediol is prepared in a process comprising the steps of:contacting, in an essentially non-water-miscible organic solvent, ethylene oxide with carbon monoxide and hydrogen in the presence of a catalytic amount of a non-phosphine-ligated cobalt compound and an effective amount of a lipophilic quaternary phosphonium salt promoter at a temperature within the range of about 50.degree. to about 100.degree. C. and a pressure within the range of about 500 to about 5000 psig, to produce an intermediate product mixture comprising less than 15 wt % 3-hydroxypropanal;adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid a major portion of the 3-hydroxypropanal at a temperature less than about 100.degree. C.Type: GrantFiled: September 30, 1994Date of Patent: October 31, 1995Assignee: Shell Oil CompanyInventors: Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Thomas C. Semple, Paul R. Weider
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Patent number: 5463147Abstract: Mixtures of isomeric decyl alcohols prepared by hydroformylation of mixtures of butene-1 and butene-2 in two stages to give aldehyde mixtures, and condensation of the aldehyde mixtures to form an aldol mixture, followed by separation and hydrogenation. The first stage of the hydroformylation proceeds in the presence of rhodium catalysts dissolved in water, the second stage in the presence of cobalt catalysts homogeneously dissolved in the reaction medium. The mixture of isomeric decyl alcohols, when esterified with phthalic acid, yields a mixture of isomeric decyl phthalates which are useful as plasticizers.Type: GrantFiled: September 23, 1994Date of Patent: October 31, 1995Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Wolfgang Greb, Peter Heymanns, Peter Lappe, Thomas Muller, Jurgen Szameitat, Ernst Wiebus
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Patent number: 5462986Abstract: Mixtures of isomeric decyl alcohols prepared by hydroformylation of mixtures of butene-1 and butene-2 in two stages to give aldehyde mixtures, and condensation of the aldehyde mixtures to form an aldol mixture, followed by separation and hydrogenation. The first stage of the hydroformylation proceeds in the presence of rhodium catalysts dissolved in water, the second stage in the presence of cobalt catalysts homogeneously dissolved in the reaction medium. The mixture of isomeric decyl alcohols, when esterified with phthalic acid, yields a mixture of isomeric decyl phthalates which are useful as plasticizers.Type: GrantFiled: February 14, 1995Date of Patent: October 31, 1995Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Wolfgana Greb, Peter Heymanns, Peter Lappe, Thomas Muller, Jurgen Szameitat, Ernst Wiebus
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Patent number: 5463146Abstract: 1,3-propanediol is prepared in a process comprising the steps of:(a) contacting ethylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of an effective amount of a non-phosphine-ligated cobalt catalyst and an effective amount of a lipophilic arsine at a temperature within the range of about 50 to about 100.degree. C. and a pressure within the range of about 500 to about 5000 psig, under reaction conditions effective to produce an intermediate product mixture comprising less than about 15 wt % 3-hydroxypropanal;(b) adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid at a temperature less than about 100.degree. C.Type: GrantFiled: September 30, 1994Date of Patent: October 31, 1995Assignee: Shell Oil CompanyInventors: Lynn H. Slaugh, Joseph B. Powell, Thomas C. Forschner, Thomas C. Semple, Paul R. Weider
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Patent number: 5463137Abstract: A propylene stream which contains propane as an impurity is contacted with carbon monoxide and hydrogen in the presence of a hydroformylation catalyst thereby producing a product stream containing butyraldehyde and/or n-butyl alcohol, unreacted propylene and propane. A gas mixture containing propylene and propane is separated from the product stream and subjected to adsorption at a temperature of 0.degree. to 250.degree. C. in a bed of adsorbent which selectively adsorbs propylene, thereby adsorbing substantially all of the propylene from the gas mixture. The propylene is desorbed from the adsorbent and recycled to the reaction zone. The process is operated on a low per pass conversion with recycle of unreacted propylene. In the system of the invention the propylene adsorption unit may be upstream or downstream of the hydroformylation reactor.Type: GrantFiled: April 22, 1994Date of Patent: October 31, 1995Assignee: The BOC Group, Inc.Inventors: Ramakrishnan Ramachandran, Loc H. Dao
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Patent number: 5457240Abstract: A method for starting a preformer reactor disposed within a hydroformylation system which comprises an oxo reactor, a stripper reactor and a preformer reactor, wherein the bottoms from the stripper reactor comprise at least a water soluble cobaltous salt and wherein the overhead from the stripper reactor comprises entrained volatile cobalt compounds, wherein at least a portion of the entrained volatile cobalt compounds from the stripper reactor are recycled to the preformer reactor to act an initiator in the conversion of the cobaltous salt to cobalt carbonyl.Type: GrantFiled: December 14, 1994Date of Patent: October 10, 1995Assignee: Exxon Chemical Patents, Inc.Inventors: Stephen W. Beadle, Claude A. Poulin
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Patent number: 5434318Abstract: Noble metal or other preformer catalysts used to convert cobalt salts to hydrido cobalt carbonyl for use in the oxonation of olefins are reactivated or regenerated by treatment with a mixture of an aqueous organic acid solution and an alcohol at a temperature of about 120.degree. C. to 170.degree. C. and a pressure of about 13.78 MPa to 31.00 MPa for about 2 to 50 hours.Type: GrantFiled: March 23, 1994Date of Patent: July 18, 1995Assignee: Exxon Chemical Patents Inc.Inventors: Ronald R. Hill, Patricia B. Roussel
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Patent number: 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: 5382716Abstract: Mixtures of isomeric decyl alcohols obtained by hydroformylation of butadiene to produce aldehyde mixtures, condensation of the aldehyde mixtures, isolated from the reaction product, to form an aldol mixture, and isolation and hydrogenation of the aldol mixture. The mixture of isomeric decyl alcohols, esterified using phthalic acid, gives a mixture of isomeric decyl phthalates which are plasticizers having excellent cold properties.Type: GrantFiled: March 23, 1993Date of Patent: January 17, 1995Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Wolfgang Greb, Peter Heymanns, Peter Lappe, Jurgen Szameitat, Thomas Muller, Ernst Wiebus
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Patent number: 5382715Abstract: The hydrogenation steps and hydrofinishing steps of the cobalt catalyst oxo process for preparation of the alcohols by the hydroformylation of olefin are carried out using a nickel-molybdenum catalyst on an alumina or silica alumina support which has a phosphorous content of O.1 wt. % to 1.0 wt. % phosphorus.Type: GrantFiled: November 29, 1993Date of Patent: January 17, 1995Assignee: Exxon Chemical Patents Inc.Inventors: Jose M. Vargas, Kenneth L. Riley
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Patent number: 5364970Abstract: A process for the hydroformylation of .alpha.-substituted, .alpha.-.beta.-unsaturated carbonyl compounds in the presence of a catalyst system based ona) a source of rhodium cations andb) a source of ligands of the formula MR.sub.1 R.sub.2 R.sub.3 wherein M represents a phosphorus, arsenic or antimony atom and R.sub.1, R.sub.2, and R.sub.3 independently represent substituted or non-substituted hydrocarbyl groups, together containing not more than 24 carbon atoms. At least one of R.sub.1, R.sub.2, and R.sub.3 is linked to M via an aliphatic carbon atom. The process is selective for the generation of alpha reaction products.Type: GrantFiled: January 25, 1994Date of Patent: November 15, 1994Assignee: Shell Oil CompanyInventors: Eit Drent, Eric Kragtwijk
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Patent number: 5321168Abstract: Noble metal or other preformer catalysts used to convert cobalt salts to hydrido cobalt carbonyl for use in the oxonation of olefins are activated or regenerated by treatment with H.sub.2 O at 120.degree. to 170.degree. C., 13.78 MPa (2,000 psig) to 31.00 MPa (4,500 psig) for 2-50 hours.Type: GrantFiled: September 16, 1993Date of Patent: June 14, 1994Assignee: Exxon Chemical Patents Inc.Inventors: Patricia B. Roussel, William H. Summerlin
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Patent number: 5268514Abstract: Mixtures of isomeric decyl alcohols are obtained by hydroformylation of 1-butene- and 2-butene-containing mixtures in two stages to give aldehyde mixtures, condensation of the isolated and combined aldehyde mixtures to form an aldol mixture, and isolation and hydrogenation of the aldol mixture. The mixture of isomeric decyl alcohols, esterified with phthalic acid, gives a mixture of isomeric decyl phthalates which are useful as plasticizers.Type: GrantFiled: March 22, 1993Date of Patent: December 7, 1993Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Wolfgang Greb, Peter Lappe, Peter Heymanns, Jurgen Szameitat, Thomas Muller, Ernst Wiebus
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Patent number: 5177228Abstract: Hydroformylation process, wherein an olefinic compound is reacted with hydrogen and carbon dioxide in the presence of a Group VIII precious metal complex catalyst containing an organic phosphorus compound as a ligand, the process being characterized by use of trialkyl phosphine, as the organic phosphorus compound, having the total carbon atom number of 27 or more in its alkyl groups.Type: GrantFiled: August 5, 1991Date of Patent: January 5, 1993Assignee: Mitsubishi Kasei CorporationInventors: Keiichi Sato, Yuji Kawaragi, Masaki Takai
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Patent number: 5091599Abstract: Cobalt is recovered from the oil/water mixed reaction product of an oxonation reaction by converting the cobalt in the oil/water product to carbonyls and absorption of the carbonyls in the residue obtained from the upgrading of the heavy fraction of a hydroformylation reaction.Type: GrantFiled: April 4, 1990Date of Patent: February 25, 1992Assignee: Exxon Chemical Patents Inc.Inventors: Nicolaas A. De Munck, Mattheus D. Olijve
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Patent number: 5041685Abstract: The present invention concerns a procedure for preparing alcohols and aldehydes from alkenes and synthesis gas by a heterogeneous reaction in which the catalyst system is composed of Ru.sub.3 (CO).sub.12 and a heterocyclic base in suspension or absorbed in a fixed carrier.Type: GrantFiled: October 25, 1989Date of Patent: August 20, 1991Assignee: Neste OyInventors: Leila Alvila, Outi Krause, Tapani Pakkanen, Tapani Venalainen
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Patent number: 5030774Abstract: A catalytic process for the hydroformylation of olefinic, sulfur containing thermally cracked petroleum streams to produce aldehydes and/or alcohols is disclosed. 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 naphtha and gas oil distillate feeds are proudced from vacuum residue by high temperature thermal cracking. Such feeds contain more than 20% olefins with 1-n-olefins as the single major types. These olefin components are hydroformylated in the presence of a cobalt cabonyl complex to produce a novel type of semilinear aldehyde and/or alcohol product containing an average of less than one alkyl branch per molecule.Type: GrantFiled: January 4, 1990Date of Patent: July 9, 1991Assignee: Exxon Research and Engineering Co.Inventors: Alexis A. Oswald, Ram N. Bhatia, Edmund J. Mozeleski, Alexandr P. Glivicky, Barry G. Brueggeman, John R. Hooton, Charles M. Smith, Chang S. Hsu
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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: 4684750Abstract: A process for the production of 2-ethyl-hexanol comprising reacting propene with carbon monoxide and hydrogen, in the presence of an aqueous catalyst containing rhodium and at least one sulfonated triarylphosphine, to form an aqueous phase and an organic phase, said organic phase comprising a mixture of materials having boiling points lower than that of n-butanal and substances having boiling points equal to or higher than that of n-butanal, said materials including i-butanal, separating said material from said substances, subjecting said substances to aldol condensation, in the presence of aqueous alkali, to form 2-ethyl hexenal, first hydrogenating said 2-ethyl-hexenal in a gas phase in the presence of a first hydrogenation catalyst and thereafter hydrogenating said 2-ethyl-hexenal in a liquid phase to form 2-ethyl-hexanol in the presence of a second hydrogenation catalyst.Type: GrantFiled: August 26, 1986Date of Patent: August 4, 1987Assignee: Ruhrchemie AktiengesellschaftInventors: Gunther Kessen, Boy Cornils, Wilhelm Gick, Ernst Wiebus, Joseph Hibbel, Hanswilhelm Bach, Wolfgang Zgorzelski
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Patent number: 4647707Abstract: The higher alcohol yield of a hydroformylation process including hydroformylation, catalyst removal, hydrogenation and higher alcohol separation stages is improved by subjecting the Heavy Oxo Fraction (HOF) obtained following higher alcohol separation to steam cracking in the presence of a catalyst system comprising a dehydration-catalytic metal on an acidic support. The resultant cracked HOF mixture comprising a major proportion of olefin and saturated hydrocarbon is recycled to the hydroformylation stage.Type: GrantFiled: November 27, 1985Date of Patent: March 3, 1987Assignee: Exxon Research & Engineering Co.Inventor: Arie van Vliet
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Patent number: 4608444Abstract: A process and accompanying catalyst for the hydroformylation of formaldehyde to glycol aldehyde is disclosed. The process features the utilization of (1) a class of transition metal phosphine-amide complexes, (2) a class of transition metal phosphine-amine complexes, and (3) mixtures of 1 and 2 as particularly suitable for use.Type: GrantFiled: March 1, 1985Date of Patent: August 26, 1986Assignee: The Halcon SD Group, Inc.Inventor: Stephen E. Jacobson
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Patent number: 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: 4511743Abstract: Process for the homologation of an alcohol wherein a ketal of the alcohol is reacted with hydrogen and carbon monoxide in the presence of a cobalt carbonyl complex and the resultant product is hydrolyzed to yield the aldehyde with one more carbon atom.Type: GrantFiled: November 4, 1983Date of Patent: April 16, 1985Assignee: Institut Francais du PetroleInventors: Claude Seite, Dominique Commereuc, Yves Chauvin
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Patent number: 4491675Abstract: A rhodium catalyzed hydroformylation process carried out in the presence of free triarylphosphine ligand and free organic tertiary bisphosphine monooxide ligand, and catalytic precursor solutions for said process.Type: GrantFiled: August 17, 1981Date of Patent: January 1, 1985Assignee: Union Carbide CorporationInventors: Anthony G. Abatjoglou, David R. Bryant
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Patent number: 4481375Abstract: The present invention relates to hydrogenation and hydroformylation catalysts based on a binuclear rhodium complex having the formula: ##STR1## wherein X and X' can be the same or different; when X and X' are the same they are organic tertiary phosphite groups and when different X is a CO group and X' is an organic tertiary phosphite group or an aromatic phosphine group, and SY and SY' are thiolato groups. The invention also comprises the processes of hydroformylation and hydrogenation using such catalytic complex.Type: GrantFiled: November 16, 1979Date of Patent: November 6, 1984Assignee: Produits Chimiques Ugine KuhlmannInventors: Philippe Kalk, Rene Poilblanc, Antoine Gaset
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Patent number: 4480137Abstract: Described is a carbonylation process using novel homogeneous trihydrocarbyl silyl-substituted alkyl diaryl phosphine transition metal complexes of the general formula:[(Ar.sub.2 PQ).sub.y SiR.sub.4 --y].sub.g (MX.sub.n).sub.swherein Ar is a C.sub.6 to C.sub.10 aromatic hydrocarbyl radical, Q is a C.sub.1 to C.sub.30 saturated straight chain divalent radical, R is a C.sub.1 to C.sub.10 hydrocarbyl, wherein Ar, Q and R, can be substituted or unsubstituted, y is 1 to 4, g times y is 1 to 6, M is a transition metal selected from the group consisting of Group VIII transition metals, X is an anion or organic ligand excluding halogen satisfying the valence and coordination sites of the metal, n is 2 to 6 and s is 1 to 3, are disclosed. These materials exhibit high thermal stability and are superior catalysts for the selective hydroformylation of olefins, particularly in the presence of excess quantities of ligand of the formula:(Ar.sub.2 PQ).sub.y SiR.sub.4 -.sub.ywherein Ar, Q, R, and y are as previously defined.Type: GrantFiled: September 29, 1982Date of Patent: October 30, 1984Assignee: Exxon Research & Engineering CompanyInventors: Alexis A. Oswald, Torris G. Jermansen, Andrew A. Westner, I-Der Huang
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Patent number: 4469895Abstract: This invention concerns an improved process of preparing predominantly linear alcohols which comprises the steps of contacting a mixture of terminal and/or internal olefins and synthesis gas with a catalyst system comprising a ruthenium-containing compound in conjunction with one or more tertiary amine promoters, dispersed in a low melting quaternary phosphonium salt and heating said resultant reaction mixture under a pressure of 100 psi or greater at a temperature of at least 50.degree. C. for a sufficient time to produce said alcohols.Type: GrantFiled: October 21, 1982Date of Patent: September 4, 1984Assignee: Texaco Inc.Inventors: John F. Knifton, Robert A. Grigsby, Jr.
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Homogeneous hydroformylation catalysis with silyl substituted alkyl diaryl phosphine metal complexes
Patent number: 4450299Abstract: Described is a carbonylation process using novel homogeneous trihydrocarbyl silyl-substituted alkyl diaryl phosphine transition metal complexes of the general formula:[(Ar.sub.2 PQ).sub.y SiR.sub.4 -y].sub.g (MX.sub.n).sub.swherein Ar is a C.sub.6 to C.sub.10 aromatic hydrocarbyl radical, Q is a C.sub.1 to C.sub.30 saturated straight chain divalent radical, R is a C.sub.1 to C.sub.10 hydrocarbyl, wherein Ar, Q and R, can be substituted or unsubstituted, y is 1 to 4, g times y is 1 to 6, M is a transition metal selected from the group consisting of Group VIII transition metals, X is an anion or organic ligand excluding halogen satisfying the valence and coordination sites of the metal, n is 2 to 6 and s is 1 to 3, are disclosed. These materials exhibit high thermal stability and are superior catalysts for the selective hydroformylation of olefins, particularly in the presence of excess quantities of ligand of the formula:(Ar.sub.2 PQ).sub.y SiR.sub.4-ywherein Ar, Q, R, and y are as previously defined.Type: GrantFiled: August 21, 1981Date of Patent: May 22, 1984Assignee: Exxon Research and Engineering Co.Inventors: Alexis A. Oswald, Torris G. Jermansen, Andrew A. Westner, I-Der Huang -
Patent number: 4447661Abstract: In a process for producing an alcohol by hydroformylation comprises reacting a straight chained, branched or alicyclic mono-olefin having from 3 to 20 carbon atoms with carbon monoxide and hydrogen to form an alcohol having carbon atoms greater in number by one than the carbon atoms of the mono-olefin, the improvement comprises(a) a fist step in which the mono-olefin is hydroformylated with use of a cobalt catalyst in the presence of a gas mixture of carbon monoxide and hydrogen at a high temperature under high pressure to selectively form an aldehyde at a conversion of the mono-olefin being from 50 to 95 mol % while suppressing the formation of an alcohol, and the cobalt catalyst is then removed from the unreacted olefin and the formed aldehyde by decomposition or extraction, and(b) a second step in which the mixture of the unreacted mono-olefin and the formed aldehyde freed from the cobalt catalyst in the first step is reacted with a gas mixture of carbon monoxide and hydrogen with use of a cobalt organophoType: GrantFiled: September 7, 1982Date of Patent: May 8, 1984Assignee: Nissan Chemical Industries Ltd.Inventors: Satoshi Hoshiyama, Hiroyuki Muto, Shuzo Shinke, Kanji Otsuka, Shinichiro Takigawa, Hiroyuki Yamazaki