By Reduction (e.g., By Hydrogenation, Etc.) Patents (Class 568/914)
  • Patent number: 10787406
    Abstract: This invention provides a composition that contains PFOB with a PFOA content lower than that of known PFOB, and that is less likely to have an adverse effect on the environment; and provides a method for producing PFOB. The composition contains C8F17Brand further contains C7F15COOH, wherein C7F15COOH is present in a concentration of 25 ppb or less based on the total weight of C8F17Br. The method for producing C8F17Br comprises reacting C8F17I and a brominating agent to obtain C8F17Br, and alkali-washing the obtained C8F17Br to reduce the C7F15COOH content to 25 ppb or less based on the total weight of C8F17Br.
    Type: Grant
    Filed: July 3, 2018
    Date of Patent: September 29, 2020
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Yoshichika Kuroki, Masahiro Higashi, Yoshihiro Yamamoto
  • Patent number: 9035110
    Abstract: The present invention relates to a process for heat integration in the preparation of saturated C3-C20-alcohols, in which a hydrogenation feed comprising at least one C3-C20-aldehyde is hydrogenated in the presence of a hydrogen-comprising gas in a hydrogenation zone and a discharge is taken off from the hydrogenation zone and subjected to distillation in at least one distillation column to give a fraction enriched in saturated C3-C20-alcohols.
    Type: Grant
    Filed: March 6, 2013
    Date of Patent: May 19, 2015
    Assignee: BASF SE
    Inventors: Roland Krokoszinski, Karl-Heinz Walczuch
  • Patent number: 9000236
    Abstract: Process for the purification of an alcohol in the course of a process comprising: (1) providing a reaction zone (C) comprising an acid type catalyst; (2) providing a reaction zone (B) comprising an acid adsorbent material; (3) providing an alcohol stream comprising impurities; (4) introducing the alcohol stream of (3) into the reaction zone (B) and bringing said stream into contact with the acid adsorbent material at conditions effective to reduce the amount of impurities having an adverse effect on the acid type catalyst of the reaction zone (C); (5) recovering from step (4) an alcohol stream and introducing it into the reaction zone (C); (6) optionally introducing one or more reactants (R) into the reaction zone (C); (7) operating said reaction zone (C) at conditions effective to recover a valuable effluent.
    Type: Grant
    Filed: November 27, 2009
    Date of Patent: April 7, 2015
    Assignee: Total Research & Technology Feluy
    Inventors: Delphine Minoux, Walter Vermeiren, Nikolai Nesterenko, Sander Van Donk, Jean-Pierre Dath
  • Publication number: 20140350308
    Abstract: A crude product stream of 1,4-butandiol and one or more of ?-butyrolactone, 2-(4-hydroxybutoxy)-tetrahydrofuran, 4-hydroxybutyl(4-hydroxybutyrate), and 3-(4-hydroxybutoxy)-tetrahydrofuran is supplied to a first distillation column. A side-draw of 1,4-butanediol and light components is removed, with the light components including at least some of those produced by reaction in the first distillation column. The stream is passed to a hydrogenation zone and subjected to hydrogenation in the presence of a hydrogenation catalyst. A 1,4-butanediol product stream having a reduced content of 2-(4-hydroxybutoxy)-tetrahydrofuran is recovered and passed to a second distillation column operated such that (4-hyroxybutyl)-4-hydroxybutyrate is removed as a bottom stream and a 1,4-butanediol stream is removed as overhead. The overhead stream removed is passed to a third distillation column and a purified 1,4-butanediol stream is recovered.
    Type: Application
    Filed: August 21, 2012
    Publication date: November 27, 2014
    Inventors: Graham Reed, Paul Gordon
  • Patent number: 8816137
    Abstract: The invention provides for a method for processing heavy oil from any sources including tar sands, oil shales, varied residues in a bi-reforming process utilizing reaction conditions with steam and carbon dioxide sufficient to form a mixture of hydrogen and carbon monoxide to form methanol. Methanol produced can be dehydrated to form dimethyl ether, with water produced being recycled back to the bi-reforming process.
    Type: Grant
    Filed: April 7, 2010
    Date of Patent: August 26, 2014
    Assignee: University of Southern California
    Inventors: George A. Olah, G.K. Surya Prakash
  • Patent number: 8581010
    Abstract: A process is disclosed for the production of ethanol from methanol whereby methanol is condensed in the gas phase over a heterogeneous catalyst to produce ethanol and water.
    Type: Grant
    Filed: May 4, 2011
    Date of Patent: November 12, 2013
    Inventor: John E. Stauffer
  • Patent number: 8426654
    Abstract: Method for producing fatty alcohols includes splitting vegetable oils and animal fats under pressure into fatty acids and glycerol in counterflow to steam. The reaction product is physically separated into fatty acids and sweet water containing glycerol. The fatty acids are subjected to a distillation, and the separated fatty acid fraction is mixed together with fatty alcohol at 230 to 270° C. and atmospheric pressure. The wax esters obtained by esterification are hydrogenated to fatty alcohols by adding hydrogen on a fixed-bed catalyst, and the reaction product is separated into fatty alcohols and hydrogen. The wax esters are hydrogenated on a fixed bed of uniformly shaped catalyst bodies produced by extrusion, which consist of the main components copper and copper-chromium oxide and the secondary components zinc, aluminum, iron, silicon and alkaline earth elements, at 180 to 220° C. and 70 to 100 bar(a).
    Type: Grant
    Filed: February 12, 2009
    Date of Patent: April 23, 2013
    Assignee: Lurgi GmbH
    Inventors: Rudolf Boensch, Klaus Noweck
  • Publication number: 20110054225
    Abstract: Method for producing fatty alcohols includes splitting vegetable oils and animal fats under pressure into fatty acids and glycerol in counterflow to steam. The reaction product is physically separated into fatty acids and sweet water containing glycerol. The fatty acids are subjected to a distillation, and the separated fatty acid fraction is mixed together with fatty alcohol at 230 to 270° C. and atmospheric pressure. The wax esters obtained by esterification are hydrogenated to fatty alcohols by adding hydrogen on a fixed-bed catalyst, and the reaction product is separated into fatty alcohols and hydrogen. The wax esters are hydrogenated on a fixed bed of uniformly shaped catalyst bodies produced by extrusion, which consist of the main components copper and copper-chromium oxide and the secondary components zinc, aluminum, iron, silicon and alkaline earth elements, at 180 to 220° C. and 70 to 100 bar(a).
    Type: Application
    Filed: February 12, 2009
    Publication date: March 3, 2011
    Applicant: LURGI GMBH
    Inventors: Rudolf Boensch, Klaus Noweck
  • Patent number: 7659433
    Abstract: 1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) substantially free of 1,1,1-trifluoroacetone (TFA) can be separated from a mixture containing both compounds by A) catalytic reduction with hydrogen followed by fractional distillation; B) cooling to a temperature at which HFIP freezes and TFA remains liquid; C) forming a high boiling complex comprising HF and TFA followed by fractional distillation; or D) producing HF-free conditions to yield a HFIP/TFA azeotrope followed by fractional distillation. It is emphasized that this abstract is provided to comply with the rules requiring an abstract, which will allow a searcher or other reader to quickly ascertain the subject matter of the technical disclosure. It is submitted with the understanding that it will not be used to interpret or limit the scope or meaning of the claims. 37 CFR § 1.72(b).
    Type: Grant
    Filed: February 4, 2005
    Date of Patent: February 9, 2010
    Assignee: Halocarbon Products Corporation
    Inventors: Paul Mazzell, Jr., Joel Swinson, Barry Jones, Daniel Graham
  • Patent number: 7569735
    Abstract: A method for producing alcohols which comprises reducing esters or lactones with hydrogen gas in the presence of a catalyst comprising (i) a ruthenium compound, (ii) a monodentate monophosphine or a bidentate bisphosphine, and (iii) an amine. Examples of the catalyst include a ruthenium (Ru) complex represented by the formula:RuX1X2(LP)m(LN)n [X1 and X2 each represent an anionic ligand, LP represents a phosphine ligand, m is 1 when LP is bidentate, while m is 2 when LP is monodentate, LN represents an amine ligand, and n is 1 when LN is bidentate, while n is 2 when LN is monodentate.] and a catalyst comprising an amine and a ruthenium (Ru) complex of the formula: RuX1X2(LP1)r [LP1 represents a monophosphine ligand and r is 3 or 4.].
    Type: Grant
    Filed: March 14, 2008
    Date of Patent: August 4, 2009
    Assignee: Takasago International
    Inventors: Yasunori Ino, Akifumi Yoshida, Wataru Kuriyama
  • Publication number: 20080058560
    Abstract: 1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) substantially free of 1,1,1-trifluoroacetone (TFA) can be separated from a mixture containing both compounds by A) catalytic reduction with hydrogen followed by fractional distillation; B) cooling to a temperature at which HFIP freezes and TFA remains liquid; C) forming a high boiling complex comprising HF and TFA followed by fractional distillation; or D) producing HF-free conditions to yield a HFIP/TFA azeotrope followed by fractional distillation. It is emphasized that this abstract is provided to comply with the rules requiring an abstract, which will allow a searcher or other reader to quickly ascertain the subject matter of the technical disclosure. It is submitted with the understanding that it will not be used to interpret or limit the scope or meaning of the claims. 37 CFR § 1.72(b).
    Type: Application
    Filed: February 4, 2005
    Publication date: March 6, 2008
    Applicant: Halocarbon Products Corporation
    Inventors: Paul Massell, Joel Swinson, Barry Jones, Daniel Graham
  • Patent number: 7335800
    Abstract: The present invention provides a hydrogenation catalyst effective for hydrogenating 3-hydroxypropionaldehyde to 1,3-propanediol. The hydrogenation catalyst comprises an ?-alumina support, nickel, ruthenium, and a promoter. The nickel is deposited on the ?-alumina support, and the ruthenium and the promoter are deposited on the nickel and the ?-alumina support. The ?-alumina support comprises at least 92 wt. % of the catalyst, and the nickel comprises from 1 wt. % to 6 wt. % of the catalyst. The present invention also provides a process of hydrogenating 3-hydroxypropionaldehyde to 1,3-propanediol with the catalyst.
    Type: Grant
    Filed: April 21, 2006
    Date of Patent: February 26, 2008
    Assignee: Shell Oil Company
    Inventors: Glenn Charles Komplin, John Anthony Smegal
  • Patent number: 7217848
    Abstract: This invention comprises a process for hydrogenation of aldehydes to alcohols using novel homogeneous catalysts. The catalysts are generated in situ under hydrogen and carbon monoxide gases in a suitable solvent, by mixing a rhodium catalyst precursor, such as Rh(CO)2 acetoacetonate and a defined ligand.
    Type: Grant
    Filed: November 29, 2004
    Date of Patent: May 15, 2007
    Assignee: Dow Global Technologies Inc.
    Inventor: Wei-Jun Peng
  • Patent number: 7183443
    Abstract: Process for the preparation of enantiomerically enriched amino aldehydes and amino alcohols, wherein a corresponding enantiomerically enriched amino nitrile is subjected to hydrogenation in the presence of hydrogen, a hydrogenation catalyst, preferably a Pd-catalyst and a mineral acid. For the preparation of an amino aldehyde hydrogen preferably is present at a hydrogen-pressure between 0.1 and 2 MPa, in particular between 0.5 and 1 MPa. The amino aldehyde preferably is isolated in the form of a chemically and configurationally stable derivative. For the preparation of an amino alcohol, preferably at least during part of the hydrogenation hydrogen is present at a hydrogen-pressure between 2 and 10 MPa, in particular between 4 and 6 MPa. In a preferred embodiment the hydrogen-pressure initially is between 0.5 and 2 MPa and subsequently, after most of the nitrile starting material is converted, the hydrogen pressure is increased to a value between 2 and 10 MPa.
    Type: Grant
    Filed: April 7, 2003
    Date of Patent: February 27, 2007
    Assignee: DSM IP Assets B.V.
    Inventors: Bernardus Henricus Nicolaas Dassen, Bernardus Kaptein, Quirinus Bernardus Broxterman
  • Patent number: 7138552
    Abstract: The present invention relates to a process for preparing a C13-alcohol mixture which is suitable, in particular, as precursor for the preparation of compounds having surfactant properties and of plasticizers.
    Type: Grant
    Filed: March 25, 2003
    Date of Patent: November 21, 2006
    Assignee: OXENO Olefinchemie GmbH
    Inventors: Alfred Kaizik, Walter Tötsch, Wilhelm Droste, Wilfried Büschken, Dirk Röttger, Klaus-Diether Wiese
  • Patent number: 6770790
    Abstract: The invention is a method to purify tertiary butyl alcohol by contact with at least two solid adsorbents comprising aluminum oxide and a large pore zeolite such as zeolite X. The purification method successfully improves product quality and reduces the amount of impurities in the tertiary butyl alcohol.
    Type: Grant
    Filed: October 17, 2003
    Date of Patent: August 3, 2004
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Xiangmin Li, Lawrence M. Candela, Yuan-Zhang Han, Andrew P. Kahn
  • Patent number: 6657092
    Abstract: Process for the preparation of a highly linear alcohol composition is provided comprising the steps of: (a) reacting carbon monoxide with hydrogen under Fischer-Tropsch reaction conditions in the presence of a Fischer-Tropsch catalyst comprising cobalt; (b) separating from the product of step (a) at least one hydrocarbon fraction comprising between 10 and 50% by weight of olefins containing 6 or more carbon atoms; (c) contacting one or more of the hydrocarbon fractions obtained in step (b) with carbon monoxide and hydrogen under hydroformylation conditions in the presence of a hydroformylation catalyst based on a source of cobalt and one or more alkyl phosphines; and (d) recovering the alcohol composition.
    Type: Grant
    Filed: June 11, 2002
    Date of Patent: December 2, 2003
    Assignee: Shell Oil Company
    Inventors: Hendrik Dirkzwager, Laurent Alain Fenouil, Joannes Ignatius Geijsel, Arend Hoek, Frederik Hendrik Van Der Steen
  • Patent number: 6441255
    Abstract: Carrier-bound ruthenium catalysts are used to produce alcohols by the catalytic hydrogenation of aldehydes and ketones. The problem of deactivation of the catalyst is solved by the use of a ruthenium catalyst on an oxide carrier of the series TiO2, SiO2, ZrO2, MgO, mixed oxides thereof and silicates thereof. In particular, Ru on TiO2 or SiO2 results in a long service life of the catalyst.
    Type: Grant
    Filed: September 27, 1999
    Date of Patent: August 27, 2002
    Assignee: Degussa -Huls AG
    Inventors: Thomas Haas, Bernd Jaeger, Jörg Sauer, Rudolf Vanheertum
  • Patent number: 6329558
    Abstract: In a process for isolating alkylene glycol having a low aldehyde content, in which a mixture comprising alkylene glycol is subjected to a final distillation, formic acid or a formate or a mixture of two or more formates or a mixture of formic acid and one or more formates is present in the mixture comprising alkylene glycol.
    Type: Grant
    Filed: June 23, 2000
    Date of Patent: December 11, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Jürgen Mohr, Toni Dockner
  • Patent number: 6232512
    Abstract: Reduction in the content of acetals or ketone acetals in a reaction mixture containing at least 10 moles alcohol per mole acetal or ketone acetal can be achieved hydrogenolytically when the reaction mixture is hydrogenated at 80° to 250° C. at a hydrogen partial pressure of 0.5 to 30 MPa in the presence of activated carbon charged with noble metal as catalyst.
    Type: Grant
    Filed: August 31, 1999
    Date of Patent: May 15, 2001
    Assignee: Degussa-Huls AG
    Inventors: Thomas Haas, Bernd Jäger, Jörg Sauer, Rudolf Vanheertum
  • Patent number: 6187970
    Abstract: 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: Grant
    Filed: April 15, 1997
    Date of Patent: February 13, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: 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
  • 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: 6172269
    Abstract: 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: Grant
    Filed: April 15, 1997
    Date of Patent: January 9, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Anil Sakharam Guram, John Robert Briggs, Diane Lee Packett, Kurt Damar Olson, Thomas Carl Eisenschmid, Erik Bruce Tjaden
  • Patent number: 6133489
    Abstract: A process for obtaining glycols of low aldehyde content in which the plant used to obtain the glycol(s) is surface-treated, in whole or in part, with at least one reductive phosphorus compound.
    Type: Grant
    Filed: July 16, 1998
    Date of Patent: October 17, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Jurgen Mohr, Frans Vansant
  • Patent number: 6034284
    Abstract: High quality trimethylolalkane can be easily and efficiently produced at a high yield through a reaction between n-alkanal and formaldehyde in the presence of tertiary amine and water, in which a reaction mixture obtained after the reaction is heated up to a temperature at which a salt of tertiary amine with formic acid produced as a by-product can be thermally dissociated so as to distill tertiary amine and water from the reaction mixture, and a formate of trimethylolalkane produced in the distillation of tertiary amine and contained in a residue is reacted with water, ammonia, primary amine or secondary amine; and the tertiary amine distilled from the reaction mixture is reused in producing trimethylolalkane.
    Type: Grant
    Filed: October 20, 1998
    Date of Patent: March 7, 2000
    Assignee: Koei Chemical Company, Limited
    Inventors: Kenji Doi, Takuhiko Jinno, Ayao Moriyama, Shingo Uji
  • Patent number: 5865957
    Abstract: A method for producing butyraldehydes, by separating and purifying mixed butyraldehyde products formed by hydroformylation of propylene, into n-butyraldehyde and isobutyraldehyde by using a distillation column, wherein the distillation column is operated under such conditions that the pressure at the top of the distillation column is within a range of from 0.001 to 0.5 kg/cm.sup.2 G, and the pressure at the bottom of the column is within a range of from 0.05 to 1.0 kg/cm.sup.2 G.
    Type: Grant
    Filed: November 6, 1995
    Date of Patent: February 2, 1999
    Assignee: Mitsubishi Chemical Company
    Inventors: Akio Ueda, Kuninori Sadaie
  • Patent number: 5741952
    Abstract: An MTBE recycle stream (which consists mainly of TBA and methanol) contaminated with residual amounts of tertiary butyl hydroperoxide, ditertiary butyl peroxide and allyl tertiary butyl peroxide can be effectively catalytically treated under mild conversion conditions with a silica-supported nickel, copper, chromium, iron catalyst in order to substantially completely decompose the peroxide contaminants and to thereby provide a treated MTBE recycle stream which is not only substantially free from contaminating quantities of such peroxides, but which also contains an enhanced amount of methyl tertiary butyl ether.
    Type: Grant
    Filed: January 11, 1993
    Date of Patent: April 21, 1998
    Assignee: Huntsman Specialty Chemicals Corporation
    Inventors: John Ronald Sanderson, John Frederick Knifton
  • Patent number: 5545712
    Abstract: An alkali metal compound such as metallic cesium, cesium hydroxide, cesium hydroxide monohydrate, metallic rubidium, rubidium hydroxide or rubidium hydroxide monohydrate is used as a catalyst, crude polyoxyalkylene polyol containing the catalyst is neutralized with a mineral acid or an organic acid, an aqueous solution layer containing an alkali metal salt is brought into contact with an anion exchange resin to adsorb mineral acid anion or organic acid anion, the alkali metal compound catalyst is recovered, alkylene oxide undergoes ring-opening addition polymerization on an active hydrogen compound in the presence of the recovered alkali metal compound catalyst to prepare polyoxyalkylene polyol, the catalyst is thereafter separated, recovered and reused, and such recycle of the alkali metal compound catalyst provides an economical process.
    Type: Grant
    Filed: August 23, 1995
    Date of Patent: August 13, 1996
    Assignee: Mitsu Toatsu Chemicals, Inc.
    Inventors: Tomoki Tsutsui, Tsukuru Izukawa, Kazuhiko Ohkubo, Yoshitsugu Sakaki
  • Patent number: 5543564
    Abstract: This invention embodies a process for releasing acidic organic compounds in high yield and good purity from aqueous solutions of their salts which comprises converting the salts by carbon dioxide to their corresponding free acidic organic compounds and metal hydrogen carbonates, removing the acidic organic compounds from the mixture by extraction with an essentially water-insoluble organic solvent, and re-extracting the organic phase with carbon dioxide containing water. Using this process, the acidic organic compounds are completely released from their corresponding salts, i.e., the organic solution is free of salt. The acidic organic compounds released by the claimed process are organic compounds which contain acidic protons which can be replaced by metals. Some examples are carboxylic acids, sulfonic acids, phosphonic acids, phenols, naphthols, and aliphatic alcohols.
    Type: Grant
    Filed: January 11, 1995
    Date of Patent: August 6, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: J urgen Kulpe, Heinz Strutz, Hans-Martin R uffer, Siegbert Rittner
  • Patent number: 5468840
    Abstract: An alkali metal compound such as metallic cesium, cesium hydroxide, cesium hydroxide monohydrate, metallic rubidium, rubidium hydroxide or rubidium hydroxide monohydrate is used as a catalyst, crude polyoxyalkylene polyol containing the catalyst is neutralized with a mineral acid or an organic acid, an aqueous solution layer containing an alkali metal salt is brought into contact with an anion exchange resin to adsorb mineral acid anion or organic acid anion, the alkali metal compound catalyst is recovered. alkylene oxide undergoes ring-opening addition polymerization on an active hydrogen compound in the presence of the recovered alkali metal compound catalyst to prepare polyoxyalkylene polyol, the catalyst is thereafter separated, recovered and reused, and such recycle of the alkali metal compound catalyst provides an economical process.
    Type: Grant
    Filed: August 29, 1994
    Date of Patent: November 21, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Tomoki Tsutsui, Tsukuru Izukawa, Kazuhiko Ohkubo, Yoshitsugu Sakaki
  • Patent number: 5399793
    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 catalyst containing Ni/Mo on alumina or silica alumina prepared by depositing an organic acid solution of Ni and Mo salts on the support, the acid being phosphorous free.
    Type: Grant
    Filed: November 29, 1993
    Date of Patent: March 21, 1995
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Jose M. Vargas, Magdiel Agosto, Kenneth L. Riley
  • Patent number: 5397439
    Abstract: A method for recovering 1,4-butanediol from a hydrolysate obtained by hydrolyzing diacetoxybutane, by (1) supplying the hydrolysate to a first distillation column, distilling off substantially all the amounts of water and acetic acid as the top stream from the first distillation column, and supplying a bottom liquid to a second distillation column, (2) distilling off diacetoxybutane and hydroxyacetoxybutane as the top or upper side stream from of the second distillation column, and circulating the distillates to a hydrolysis zone, while withdrawing crude 1,4-butanediol as a lower side stream in vapor phase from the second distillation column, (3) supplying the crude 1,4-butanediol and hydrogen gas to a hydrogenation reaction zone packed with a hydrogenation catalyst, and (4) supplying the hydrogenation reaction product to a third distillation column, distilling off low boiling point components and withdrawing 1,4-butanediol as the bottom or side stream from the third distillation column.
    Type: Grant
    Filed: December 9, 1993
    Date of Patent: March 14, 1995
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Hiroaki Kandori, Ken Siraga
  • 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: 5306848
    Abstract: The hydrogenation steps and hydrofinishing steps of the cobalt catalyst oxo process for the preparation of alcohols by the hydroformylation of olefin are carried out using a trimetallic catalyst composed of metal oxides, particularly nickel oxide, molybdenum oxide and cobalt oxide supported on alumina or an alumina-silica in sulfided and non-sulfided form.
    Type: Grant
    Filed: October 16, 1992
    Date of Patent: April 26, 1994
    Assignee: Exxon Chemical Patents Inc.
    Inventor: Jose M. Vargas
  • Patent number: 5220020
    Abstract: A process is provided whereby organic carbonyl substrates, including esters, lactones, ketones, amides and imides are reduced in a reaction with a silane reducing reagent and a catalyst. Exemplary catalysts include metal alkoxides and metal aryloxides.
    Type: Grant
    Filed: November 14, 1991
    Date of Patent: June 15, 1993
    Assignee: Massachusetts Institute of Technology
    Inventors: Stephen L. Buchwald, Alberto Gutierrez, Scott C. Berk, Kristina A. Kreutzer
  • Patent number: 5196603
    Abstract: This invention relates to a process for removing impurities contained in a teritary butyl alcohol feedstock. The process involves contacting the feedstock with an iron (II) compound such as iron (II) chloride, under an inert atmosphere at elevated pressures and temperatures for a time sufficient to reduce the peroxides to alcohols and oxidize the iron (II) to iron (III). The iron (II) compound is added in a homogeneous phase which, after reaction has occurred, gives a mixture of the treated teritary butyl alcohol, iron (III) compound and any residual iron (II) compound. The iron (III) and any iron (II) compounds are separated from the product by contacting the mixture with a cation exchange column.
    Type: Grant
    Filed: January 30, 1992
    Date of Patent: March 23, 1993
    Assignee: UOP
    Inventors: Chwu-Ching Jan, Thomas P. Malloy
  • Patent number: 5185480
    Abstract: Methanol contaminated with residual amounts of peroxide contaminants such as tertiary butyl hydroperoxide, ditertiary butyl peroxide, allyl tertiary butyl peroxide, etc., can be effectively catalytically treated with a catalyst consisting essentially of titania-supported transition metals to substantially completely decompose the peroxide contaminants to thereby provide a treated methanol product substantially free from contaminating quantities of such peroxides.
    Type: Grant
    Filed: July 28, 1992
    Date of Patent: February 9, 1993
    Assignee: Texaco Chemical Company
    Inventors: John R. Sanderson, John F. Knifton
  • Patent number: 5124492
    Abstract: This invention relates to a process for removing peroxide impurities contained in a tertiary butyl alcohol feedstock. The process involves contacting the feedstock with an iron (II) compound such as iron (II) chloride, under an inert atmosphere at elevated pressures and temperatures for a time sufficient to reduce the peroxides to alcohols and oxidize the iron (II) to iron (III). The iron (II) compound may be added in a homogeneous phase or it may be deposited on a support. When the iron (II) is added as a homogeneous phase, it is separated from the product by contacting the mixture with a cation exchange column. Finally, when a supported iron (II) compound is used, the process may be run in a batch or continuous mode.
    Type: Grant
    Filed: February 12, 1991
    Date of Patent: June 23, 1992
    Assignee: UOP
    Inventors: Chwu-Ching Jan, Thomas P. Malloy
  • Patent number: 5004845
    Abstract: Aliphatic aldehydes are hydrogenated to alcohols containing by product ester which ester is removed and separately hydrogenated to provide additional product.
    Type: Grant
    Filed: June 27, 1988
    Date of Patent: April 2, 1991
    Assignee: Davy McKee (London) Limited
    Inventors: Michael W. Bradley, Norman Harris, Keith Turner
  • Patent number: 4922033
    Abstract: A tertiary butyl hydroperoxide feedstock, such as one prepared by the reaction of isobutane with molecular oxygen comprising tertiary butyl hydroperoxide dissolved in tertiary butyl alcohol, is charged to a catalytic decomposition zone where the tertiary butyl hydroperoxide is catalytically decomposed in the presence of a soluble ruthenium catalyst compound promoted with a bidentate ligand to provide a decomposition reaction product characterized by a high conversion rate and a high selectivity of tertiary butyl hydroperoxide to tertiary butyl alcohol.
    Type: Grant
    Filed: September 8, 1987
    Date of Patent: May 1, 1990
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, John F. Knifton, Edward T. Marquis
  • Patent number: 4922034
    Abstract: Tertiary butyl alcohol is prepared by the catalytic decomposition of tertiary butyl hydroperoxide, preferably in solution in tertiary butyl alcohol, in the presence of a metal porphine catalyst, optionally promoted with a C.sub.1 to C.sub.18 alkyl thiol and an amine, such as an iron (III) or manganese (III) porphine and, optionally, a thiol such as dodecane thiol and an amine, such as a heterocyclic amine (e.g., pyridine, quinoline, isoquinoline, imidazole or a 1-alkyl or 2-alkyl imidazole).
    Type: Grant
    Filed: September 8, 1987
    Date of Patent: May 1, 1990
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Edward T. Marquis, Mark A. Mueller
  • Patent number: 4922035
    Abstract: Tertiary butyl alcohol is prepared by the catalytic decomposition of tertiary butyl hydroperoxide, preferably in solution in tertiary butyl alcohol, in the presence of a metal phthalocyanine catalyst promoted with a C.sub.1 to C.sub.18 thiol and a free radical inhibitor, such as a phthalocyanine of a metal of Group IB, Group VIIB or Group VIIIB of the Periodic Table (e.g., chloroferric phthalocyanine, dodecane thiol and 2,3-dihydroxynaphthalene).
    Type: Grant
    Filed: September 8, 1987
    Date of Patent: May 1, 1990
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Edward T. Marquis
  • Patent number: 4922036
    Abstract: Tertiary butyl alcohol is prepared by the catalytic decomposition of tertiary butyl hydroperoxide, preferably in solution in tertiary butyl alcohol, in the presence of a borate-promoted metal phthalocyanine catalyst such as a Group IB, VIIB or VIIIB metal phthalocyanine and a Group IA, IIA or IIB metal borate, for example, chloroferric phthalocyanine and lithium borate, barium borate, zinc borate or sodium metaborate.
    Type: Grant
    Filed: September 8, 1987
    Date of Patent: May 1, 1990
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Edward T. Marquis, John F. Knifton
  • Patent number: 4912267
    Abstract: Tertiary butyl alcohol is prepared by the catalytic decomposition of tertiary butyl hydroperoxide, preferably in solution in tertiary butyl alcohol, in the presence of a base-promoted metal phthalocyanine catalyst, such as a phthalocyanine of a metal of Group IB, Group VIIB or Group VIIIB of the Periodic Table (e.g., chloroferric phthalocyanine and a base having a pH greater than about 7.5 when 0.10 mole is dissolved in one liter of water, such as sodium carbonate, sodium acetate, sodium phosphate, ammonium hydrogen phosphate, lithium carbonate, etc.).
    Type: Grant
    Filed: September 8, 1987
    Date of Patent: March 27, 1990
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, John F. Knifton
  • Patent number: 4912266
    Abstract: In order to prepare a feedstock, isobutane is reacted with oxygen in an oxidation zone to provide an oxidation product comprising a solution of tertiary butyl hydroperoxide in unreacted isobutane. A catalyst may be present to catalyze the reaction of the oxygen with the isobutane if desired.The feedstock is charged to a catalytic decomposition zone wherein the tertiary butyl hydroperoxide is decomposed in the presence of an imidazole-promoted metal phthalocyanine catalyst to provide a decomposition reaction product characterized by a compartively high conversion rate and a compartively high selectively of tertiary butyl hydroperoxide to tertiary butyl alcohol.
    Type: Grant
    Filed: September 8, 1987
    Date of Patent: March 27, 1990
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, John F. Knifton, Edward T. Marquis, Mark A. Mueller
  • Patent number: 4910349
    Abstract: Tertiary butyl alcohol is prepared by the catalytic decomposition of tertiary butyl hydroperoxide, preferably in solution in tertiary butyl alcohol, in the presence of a metal phthalocyanine catalyst promoted with a rhenium compound, such as a phthalocyanine of a metal of Group IB, Group VIIB or Group VIIIB of the Periodic Table (e.g., chloroferric phthalocyanine and rhenium heptoxide-p-dioxane or oxotrichloro-bis-(triphenylphosphine) rhenium V).
    Type: Grant
    Filed: September 8, 1987
    Date of Patent: March 20, 1990
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, John F. Knifton, Edward T. Marquis
  • Patent number: 4873380
    Abstract: Motor-fuel grade tertiary butyl alcohol contaminated with residual amounts of tertiary butyl hydroperoxide and ditertiary butyl peroxide (which is prepared, for example, by reacting propylene with tertiary butyl hydroperoxide to form propylene oxide and a motor fuel grade tertiary butyl alcohol reaction product) can be effectively catalytically treated under mild conversion conditions including a temperature of about 80.degree. to 200.degree. C. with a catalyst consisting essentially of nickel, copper, chromium and barium to substantially selectively convert the two peroxide contaminants to tertiary butyl alcohol and to thereby provide a treated tertiary butyl alcohol product substantially free from contaminating quantities of such peroxides.
    Type: Grant
    Filed: January 20, 1987
    Date of Patent: October 10, 1989
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, John M. Larkin
  • Patent number: 4742179
    Abstract: Motor-fuel grade tertiary butyl alcohol contaminated with residual amounts of tertiary butyl hydroperoxide and ditertiary butyl peroxide (which is prepared, for example, by reacting propylene with tertiary butyl hydroperoxide to form propylene oxide and a motor fuel grade tertiary butyl alcohol reaction product) can be effectively catalytically treated under mild conversion conditions including a temperature of about 80.degree. to 180.degree. C. with a base-treated hydrogenation catalyst from groups VIB or VIIIB of the Periodic Table in order to substantially selectively convert the two peroxide contaminants to tertiary butyl alcohol and to thereby provide a treated tertiary butyl alcohol product substantially free from contaminating quantities of such peroxides.
    Type: Grant
    Filed: November 3, 1986
    Date of Patent: May 3, 1988
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Robert M. Gipson, Kenneth P. Keating, Edward T. Marquis
  • Patent number: 4443638
    Abstract: A process for preparing alcohols from internal olefins is disclosed. Briefly, the process comprises (a) hydroformylation of internal olefins to aldehydes using a small amount of a ligand modified recycled rhodium catalyst, (b) separating the reaction product from the catalyst by flash vacuum distillation, (c) hydrogenating the aldehydes to form a product containing alcohols, and (d) removing impurities and recovering the desired alcohol product. An important feature of this process, centers around the use of internal olefins to make an alcohol product which has a large amount of linear alcohol and 2-methyl-branched alcohol in the product.
    Type: Grant
    Filed: April 19, 1982
    Date of Patent: April 17, 1984
    Assignee: Conoco, Inc.
    Inventor: James A. Yates
  • Patent number: 4401834
    Abstract: An improved process for producing alcohols which comprises passing a demetalled hydroformylation liquid effluent comprising aldehyde and alcohol and containing acetal impurities to a thermal treatment zone; subjecting the demetalled hydroformylation effluent in the thermal treatment zone in the absence of added acidic compounds and in the presence of water to a temperature of from about 350.degree. to 500.degree. F. for a time sufficient to convert at least a major portion of the acetal impurities to the corresponding aldehydes and alcohols and to form an aldehyde-containing liquid containing substantially reduced levels of the acetal impurities; withdrawing the aldehyde-containing liquid from the thermal treatment zone and rapidly cooling the liquid to a temperature of about 300.degree. F.
    Type: Grant
    Filed: June 1, 1982
    Date of Patent: August 30, 1983
    Assignee: Exxon Research & Engineering Co.
    Inventor: Terry S. King