Including Hydroformylation Patents (Class 568/882)
  • Patent number: 6228829
    Abstract: This invention relates to granular detergent products which include mid-chain branched surfactants.
    Type: Grant
    Filed: April 4, 2000
    Date of Patent: May 8, 2001
    Assignee: The Procter & Gamble Company
    Inventors: Phillip Kyle Vinson, Thomas Anthony Cripe, Kenneth William Willman, Robert Emerson Stidham, Daniel Stedman Connor
  • Patent number: 6184424
    Abstract: 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: Grant
    Filed: September 15, 1999
    Date of Patent: February 6, 2001
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Wilfried Bueschken, Dietmar Gubisch
  • Patent number: 6087309
    Abstract: This invention relates to a liquid cleaning composition comprising a surfactant system containing selected mid-chain branched surfactant and co-surfactants.
    Type: Grant
    Filed: November 4, 1999
    Date of Patent: July 11, 2000
    Assignee: The Procter & Gamble Company
    Inventors: Phillip Kyle Vinson, Peter Robert Foley, Thomas Anthony Cripe, Daniel Stedman Connor
  • Patent number: 6060443
    Abstract: 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: Grant
    Filed: October 13, 1998
    Date of Patent: May 9, 2000
    Assignee: The Procter & Gamble Company
    Inventors: Thomas Anthony Cripe, Daniel Stedman Connor, Phillip Kyle Vinson, James Charles Theophile Roger Burckett-St. Laurent, Kenneth William Willman, Jeffrey Scott Dupont
  • Patent number: 6051743
    Abstract: 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: Grant
    Filed: December 7, 1993
    Date of Patent: April 18, 2000
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Bahrmann, Gregor Deckers, Wolfgang Greb, Peter Heymanns, Peter Lappe, Thomas Muller, Jurgen Szameitat, Ernst Wiebus
  • Patent number: 6049011
    Abstract: 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: Grant
    Filed: October 15, 1997
    Date of Patent: April 11, 2000
    Assignee: 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
  • Patent number: 6034286
    Abstract: 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: Grant
    Filed: October 16, 1997
    Date of Patent: March 7, 2000
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Anil Sakharam Guram, John Robert Briggs, Kurt Damar Olson, Thomas Carl Eisenschmid, Diane Lee Packett, Erik Bruce Tjaden
  • Patent number: 6015928
    Abstract: 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: Grant
    Filed: December 15, 1997
    Date of Patent: January 18, 2000
    Assignee: Huels Aktiengesellschaft
    Inventors: Dietmar Gubisch, Klaus Armbrust, Alfred Kaizik, Bernhard Scholz, Rudolf Nehring
  • Patent number: 6008181
    Abstract: 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: Grant
    Filed: October 13, 1998
    Date of Patent: December 28, 1999
    Assignee: The Procter & Gamble Company
    Inventors: Thomas Anthony Cripe, Daniel Stedman Connor, Phillip Kyle Vinson, James Charles Theophile Roger Burckett-St. Laurent, Kenneth William Willman
  • Patent number: 6005148
    Abstract: 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: Grant
    Filed: November 17, 1998
    Date of Patent: December 21, 1999
    Assignee: Seton Hall University
    Inventors: Setrak K. Tanielyan, Robert L. Augustine
  • Patent number: 5962744
    Abstract: 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: Grant
    Filed: March 27, 1998
    Date of Patent: October 5, 1999
    Assignees: The Research Foundation of State University of New York, Mitsubishi Chemical Corporation
    Inventors: Iwao Ojima, Hisao Urata
  • Patent number: 5922921
    Abstract: 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: Grant
    Filed: October 27, 1997
    Date of Patent: July 13, 1999
    Assignee: Celanese International Corporation
    Inventors: Jerry D. Unruh, Debra A. Ryan, Shannon L. Dugan
  • Patent number: 5877358
    Abstract: 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 th
    Type: Grant
    Filed: September 23, 1996
    Date of Patent: March 2, 1999
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Ronald D. Garton, Donald Q. Brown, Magdiel Agosto
  • Patent number: 5866725
    Abstract: 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: Grant
    Filed: December 11, 1997
    Date of Patent: February 2, 1999
    Assignee: Celanese International Corporation
    Inventors: Jerry D. Unruh, Debra A. Ryan, Shannon L. Dugan
  • Patent number: 5661204
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: August 26, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Bahrmann, Wolfgang Greb, Peter Heymanns, Peter Lappe, Thomas Muller, Jurgen Szameitat, Ernst Wiebus
  • Patent number: 5600031
    Abstract: 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: Grant
    Filed: August 18, 1995
    Date of Patent: February 4, 1997
    Assignee: Exxon Chemical Patents, Inc.
    Inventor: Patricia B. Roussel
  • Patent number: 5583250
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: December 10, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Bahrmann, Wolfgang Greb, Peter Heymanns, Peter Lappe, Thomas M uller, J urgen Szameitat, Ernst Wiebus
  • Patent number: 5545767
    Abstract: 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: Grant
    Filed: September 30, 1994
    Date of Patent: August 13, 1996
    Assignee: Shell Oil Company
    Inventors: Paul R. Weider, Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Thomas C. Semple
  • Patent number: 5516948
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: May 14, 1996
    Assignee: Hoechst AG
    Inventors: Helmut Bahrmann, Wolfgang Greb, Peter Heymanns, Peter Lappe, Thomas Muller, Jurgen Szameitat, Ernst Wiebus
  • Patent number: 5504261
    Abstract: 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: Grant
    Filed: August 1, 1994
    Date of Patent: April 2, 1996
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Thomas C. Mullin, Nicholas Triantafillou
  • Patent number: 5463144
    Abstract: 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: Grant
    Filed: September 30, 1994
    Date of Patent: October 31, 1995
    Assignee: Shell Oil Company
    Inventors: Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Terry B. Thomason, Thomas C. Semple, Paul R. Weider, Juan P. Arhancet
  • Patent number: 5463145
    Abstract: 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: Grant
    Filed: September 30, 1994
    Date of Patent: October 31, 1995
    Assignee: Shell Oil Company
    Inventors: Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Thomas C. Semple, Paul R. Weider
  • Patent number: 5463147
    Abstract: 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: Grant
    Filed: September 23, 1994
    Date of Patent: October 31, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Bahrmann, Wolfgang Greb, Peter Heymanns, Peter Lappe, Thomas Muller, Jurgen Szameitat, Ernst Wiebus
  • Patent number: 5462986
    Abstract: 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: Grant
    Filed: February 14, 1995
    Date of Patent: October 31, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Bahrmann, Wolfgana Greb, Peter Heymanns, Peter Lappe, Thomas Muller, Jurgen Szameitat, Ernst Wiebus
  • Patent number: 5463146
    Abstract: 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: Grant
    Filed: September 30, 1994
    Date of Patent: October 31, 1995
    Assignee: Shell Oil Company
    Inventors: Lynn H. Slaugh, Joseph B. Powell, Thomas C. Forschner, Thomas C. Semple, Paul R. Weider
  • Patent number: 5463137
    Abstract: 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: Grant
    Filed: April 22, 1994
    Date of Patent: October 31, 1995
    Assignee: The BOC Group, Inc.
    Inventors: Ramakrishnan Ramachandran, Loc H. Dao
  • Patent number: 5457240
    Abstract: 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: Grant
    Filed: December 14, 1994
    Date of Patent: October 10, 1995
    Assignee: Exxon Chemical Patents, Inc.
    Inventors: Stephen W. Beadle, Claude A. Poulin
  • Patent number: 5434318
    Abstract: 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: Grant
    Filed: March 23, 1994
    Date of Patent: July 18, 1995
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Ronald R. Hill, Patricia B. Roussel
  • Patent number: 5406006
    Abstract: 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: Grant
    Filed: May 24, 1994
    Date of Patent: April 11, 1995
    Assignee: Exxon Chemical Patents Inc
    Inventors: Ronald R. Hill, Patricia B. Roussel
  • Patent number: 5382716
    Abstract: 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: Grant
    Filed: March 23, 1993
    Date of Patent: January 17, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Bahrmann, Wolfgang Greb, Peter Heymanns, Peter Lappe, Jurgen Szameitat, Thomas Muller, Ernst Wiebus
  • Patent number: 5382715
    Abstract: 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: Grant
    Filed: November 29, 1993
    Date of Patent: January 17, 1995
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Jose M. Vargas, Kenneth L. Riley
  • Patent number: 5364970
    Abstract: 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: Grant
    Filed: January 25, 1994
    Date of Patent: November 15, 1994
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Eric Kragtwijk
  • Patent number: 5321168
    Abstract: 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: Grant
    Filed: September 16, 1993
    Date of Patent: June 14, 1994
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Patricia B. Roussel, William H. Summerlin
  • Patent number: 5268514
    Abstract: 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: Grant
    Filed: March 22, 1993
    Date of Patent: December 7, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Bahrmann, Wolfgang Greb, Peter Lappe, Peter Heymanns, Jurgen Szameitat, Thomas Muller, Ernst Wiebus
  • Patent number: 5177228
    Abstract: 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: Grant
    Filed: August 5, 1991
    Date of Patent: January 5, 1993
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Keiichi Sato, Yuji Kawaragi, Masaki Takai
  • Patent number: 5091599
    Abstract: 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: Grant
    Filed: April 4, 1990
    Date of Patent: February 25, 1992
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Nicolaas A. De Munck, Mattheus D. Olijve
  • Patent number: 5041685
    Abstract: 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: Grant
    Filed: October 25, 1989
    Date of Patent: August 20, 1991
    Assignee: Neste Oy
    Inventors: Leila Alvila, Outi Krause, Tapani Pakkanen, Tapani Venalainen
  • Patent number: 5030774
    Abstract: 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: Grant
    Filed: January 4, 1990
    Date of Patent: July 9, 1991
    Assignee: 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
  • Patent number: 4710587
    Abstract: A process for selectively removing alkyl substituted phosphine from an organic liquid containing same and triarylphosphine by treating said liquid with phosphoric acid.
    Type: Grant
    Filed: August 2, 1985
    Date of Patent: December 1, 1987
    Assignee: Union Carbide Corp.
    Inventors: David R. Bryant, Richard A. Galley
  • Patent number: 4684750
    Abstract: 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: Grant
    Filed: August 26, 1986
    Date of Patent: August 4, 1987
    Assignee: Ruhrchemie Aktiengesellschaft
    Inventors: Gunther Kessen, Boy Cornils, Wilhelm Gick, Ernst Wiebus, Joseph Hibbel, Hanswilhelm Bach, Wolfgang Zgorzelski
  • Patent number: 4647707
    Abstract: 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: Grant
    Filed: November 27, 1985
    Date of Patent: March 3, 1987
    Assignee: Exxon Research & Engineering Co.
    Inventor: Arie van Vliet
  • Patent number: 4608444
    Abstract: 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: Grant
    Filed: March 1, 1985
    Date of Patent: August 26, 1986
    Assignee: The Halcon SD Group, Inc.
    Inventor: Stephen E. Jacobson
  • Patent number: 4605793
    Abstract: 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: Grant
    Filed: July 13, 1984
    Date of Patent: August 12, 1986
    Assignee: International Flavors & Fragrances, Inc.
    Inventors: Braja D. Mookherjee, Robert W. Trenkle, Robin K. Wolff, Richard M. Boden, Takao Yoshida
  • Patent number: 4511743
    Abstract: 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: Grant
    Filed: November 4, 1983
    Date of Patent: April 16, 1985
    Assignee: Institut Francais du Petrole
    Inventors: Claude Seite, Dominique Commereuc, Yves Chauvin
  • Patent number: 4491675
    Abstract: 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: Grant
    Filed: August 17, 1981
    Date of Patent: January 1, 1985
    Assignee: Union Carbide Corporation
    Inventors: Anthony G. Abatjoglou, David R. Bryant
  • Patent number: 4481375
    Abstract: 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: Grant
    Filed: November 16, 1979
    Date of Patent: November 6, 1984
    Assignee: Produits Chimiques Ugine Kuhlmann
    Inventors: Philippe Kalk, Rene Poilblanc, Antoine Gaset
  • Patent number: 4480137
    Abstract: 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: Grant
    Filed: September 29, 1982
    Date of Patent: October 30, 1984
    Assignee: Exxon Research & Engineering Company
    Inventors: Alexis A. Oswald, Torris G. Jermansen, Andrew A. Westner, I-Der Huang
  • Patent number: 4469895
    Abstract: 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: Grant
    Filed: October 21, 1982
    Date of Patent: September 4, 1984
    Assignee: Texaco Inc.
    Inventors: John F. Knifton, Robert A. Grigsby, Jr.
  • Patent number: 4450299
    Abstract: 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: Grant
    Filed: August 21, 1981
    Date of Patent: May 22, 1984
    Assignee: Exxon Research and Engineering Co.
    Inventors: Alexis A. Oswald, Torris G. Jermansen, Andrew A. Westner, I-Der Huang
  • Patent number: 4447661
    Abstract: 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 organopho
    Type: Grant
    Filed: September 7, 1982
    Date of Patent: May 8, 1984
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Satoshi Hoshiyama, Hiroyuki Muto, Shuzo Shinke, Kanji Otsuka, Shinichiro Takigawa, Hiroyuki Yamazaki