Title:
SPECIFIC POLYBRANCHED ALDEHYDES, ALCOHOLS SURFACTANTS AND CONSUMER PRODUCTS BASED THEREON
Document Type and Number:
WIPO Patent Application WO/2010/033976
Kind Code:
A3
Abstract:
A process for preparing a detergent alcohol mixture comprising the steps of providing one or more poly-branched poly-olefins, wherein the poly-branched poly-olefins must contain one non-branched terminal olefin and one or more additional branched olefins in the molecule; hydroformylating said poly-branched poly-olefins to produce a poly-branched olefin containing aldehyde product with one or more olefins or mixture thereof; reducing the aldehyde product of step (b) in the presence of hydrogen and a hydrogenation catalyst to form a poly-branched detergent alcohol mixture; and removing said poly-branched alcohol mixture from said catalyst and branched aldehydes, alcohols and surfactants produced from the products of this process.
Inventors:
SCHEIBEL JEFFREY JOHN (US)
SHUMATE ROBERT EDWARD (US)
SHUMATE ROBERT EDWARD (US)
Application Number:
PCT/US2009/057811
Publication Date:
May 14, 2010
Filing Date:
September 22, 2009
Export Citation:
Assignee:
PROCTER & GAMBLE (US)
SCHEIBEL JEFFREY JOHN (US)
SHUMATE ROBERT EDWARD (US)
SCHEIBEL JEFFREY JOHN (US)
SHUMATE ROBERT EDWARD (US)
International Classes:
C07C45/50; C07C29/141; C07C29/16; C07C29/17; C07C31/125; C07C41/03; C07C43/11; C07C47/02; C07C47/21; C07C305/04; C07C309/03; C11D1/14; C11D1/72; C11D1/831
Foreign References:
| US3641155A | 1972-02-08 | |||
| US4806661A | 1989-02-21 | |||
| EP0542217A2 | 1993-05-19 | |||
| US3240816A | 1966-03-15 | |||
| US4454145A | 1984-06-12 | |||
| US5510510A | 1996-04-23 | |||
| US6153577A | 2000-11-28 | |||
| US20080118443A1 | 2008-05-22 | |||
| US6150322A | 2000-11-21 | |||
| US3420898A | 1969-01-07 |
Other References:
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SOICHI SAKANE ET AL: "ASYMMETRIC CYCLIZATION OF UNSATURATED ALDEHYDES CATALYZED BY A CHIRAL LEWIS ACID", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 26, no. 45, 1 January 1985 (1985-01-01), pages 5535 - 5538, XP007911907, ISSN: 0040-4039
TAKASHI MINO ET AL: "Hydrolysis of Beta,gamma-Unsaturated Aldehyde Dimethylhydrazones with Copper Dichloride: A New Synthesis of Lavandulol", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, EASTON.; US, vol. 62, no. 3, 1 January 1997 (1997-01-01), pages 734 - 735, XP007911906, ISSN: 0022-3263
OLGA B MOROZOVA ET AL: "1H and 13C Nuclear Polarization in Consecutive Biradicals during the Photolysis of 2,2,12,12-Tetramethylcyclododecanone", JOURNAL OF PHYSICAL CHEMISTRY. A, MOLECULES, SPECTROSCOPY,KINETICS, ENVIRONMENT AND GENERAL THEORY, WASHINGTON, DC, US, vol. 101, no. 4, 1 January 1997 (1997-01-01), pages 399 - 406, XP007911901, ISSN: 1089-5639
YONGSONG H ET AL: "Novel Unsaturated Triterpenoid Hydrocarbons from Sediments of Sacred Lake, Mt.Kenya, Kenya", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 52, no. 20, 13 May 1996 (1996-05-13), pages 6973 - 6982, XP004103940, ISSN: 0040-4020
MALLYABAEVA M I ET AL: "New method for the synthesis of (3R,7R)-hexahydrofarnesyl bromide based on the microwave-activated regioselective enolization of homochiral phytone", RUSSIAN CHEMICAL BULLETIN, KLUWER ACADEMIC PUBLISHERS-PLENUM PUBLISHERS, NE, vol. 56, no. 12, 20 September 2008 (2008-09-20), pages 2443 - 2447, XP019648896, ISSN: 1573-9171
ODINOKOV V N ET AL: "New Enantiospecific Synthesis of (+)-(2R,6R)-(+)-2,6,10-Trimethylunde can-1-ol for Constructing the Side Chain of Natural (2R,4'R,8'R)-(+)-[alpha]-Tocopherol (Vitamin E)", DOKLADY CHEMISTRY, KLUWER ACADEMIC PUBLISHERS-PLENUM PUBLISHERS, NE, vol. 403, no. 4-6, 1 August 2005 (2005-08-01), pages 144 - 147, XP019296097, ISSN: 1608-3113
HIRD NICHOLAS W ET AL: "The total synthesis of 10-(R,S)-C30 botryococcene and botryococcane and a new synthesis of a general intermediate to the botryococcene family", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 30, no. 36, 1 January 1989 (1989-01-01), pages 4867 - 4870, XP002472023, ISSN: 0040-4039
UEMOTO K ET AL: "Prenyl and geranyl phenyl sulfone, a new carbon nucleophile for Mitsunobu-type alkylation", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 42, no. 5, 29 January 2001 (2001-01-29), pages 905 - 907, XP004314714, ISSN: 0040-4039
EVANS DAVID A ET AL: "Synthetic studies in the lysocellin family of polyether antibiotics. The total synthesis of ferensimyc in B", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, NEW YORK, USA, vol. 113, no. 20, 1 January 1991 (1991-01-01), pages 7613 - 7630, XP002962307, ISSN: 0002-7863
POPPE L ET AL: "CONVENIENT SYNTHETIC ROUTE TO (+)-FARANAL AND (+)-13-NORFARANAL THE TRAIL PHEROMONE OF PHARAOH'S ANT AND ITS CONGENER", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 44, no. 5, 1 January 1988 (1988-01-01), pages 1477 - 1487, XP002034539, ISSN: 0040-4020
NOAL COHEN AND BEATRICE SCHAER: "Synthesis of (2RS,4'R,8'R )-a-Tocopherol and Related Compounds via a 2-Chlorochroman", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, EASTON.; US, vol. 57, no. 21, 1 January 1992 (1992-01-01), pages 5783 - 5785, XP007911926, ISSN: 0022-3263
DIETMAR APPELHANS ET AL: "Syntheses with Aliphatic Dialdehydes, XLVI. Synthesis and Reactions of 2,2-Dialkyl-Substituted Malonaldehydes and Their Semi(Ethylene Acetals)", LIEBIGS ANNALEN: ORGANIC AND BIOORGANIC CHEMISTRY, VCH PUBLISHERS, US, vol. 11, 22 October 1997 (1997-10-22), pages 2385 - 2392, XP009129883, ISSN: 0947-3440
HIROSHI OHRUI ET AL: "Development of Highly Potent D-Glucosamine-Based Chiral Fluorescent Labeling Reagents and a Microwave-Assisted Beta-Selective Glycosidation of a Methyl Glycoside Reagent", BIOSCIENCE BIOTECHNOLOGY BIOCHEMISTRY, JAPAN SOCIETY FOR BIOSCIENCE, BIOTECHNOLOGY, AND AGROCHEMISTRY, TOKYO, JAPAN, vol. 69, no. 5, 1 May 2005 (2005-05-01), pages 1054 - 1057, XP007911909, ISSN: 0916-8451
PAULO H G ZARBIN ET AL: "SYNTHESIS AND BIOLOGICAL ACTIVITY OF METHYL 2,6,10-TRIMETHYLDODECANO ATE AND METHYL 2,6,10-TRIMETHYLTRIDECANOATE: MALE-PRODUCED SEXUAL PHEROMONES OF STINK BUGS Euschistus heros AND Piezodorus guildinii", JOURNAL OF CHEMICAL ECOLOGY, PLENUM PUBLISHING CORPORATION, US, vol. 26, no. 12, 1 January 2000 (2000-01-01), pages 2737 - 2746, XP007911904, ISSN: 0098-0331
ERWAN SAOUTER: "Natural and Synthetic Surfactants. Which one is better?", INTERNET CITATION, 23 October 2003 (2003-10-23), pages 13PP, XP007911908, Retrieved from the Internet [retrieved on 20100224]
FRANCIS J MCQUILLIN AND DAVID GEORGE PARKER: "Complexing of terpenes with transition metals. Part V. Reactions of 3,7-dimethylocta-1,6-diene and of 7-methoxy-3,7-dimethyloct-1-ene with rhodium(III) and thallium(III)", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, CHEMICAL SOCIETY, LETCHWORTH; GB, vol. 20, 1 January 1975 (1975-01-01), pages 2092 - 2096, XP009130044, ISSN: 0300-922X
FOCA C M ET AL: "Hydroformylation of myrcene: metal and ligand effects in the hydroformylation of conjugated dienes", NEW JOURNAL OF CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, GB, vol. 27, 3 February 2003 (2003-02-03), pages 533 - 539, XP007911905, ISSN: 1144-0546
CLIMENT M J ET AL: "Aldol Condensation on Solid catalysts: A Cooperative Effect between Weak Acid and Base Sites", ADVANCED SYNTHESIS & CATALYSIS, WILEY VCH VERLAG, WEINHEIM, DE, vol. 344, no. 10, 1 January 2002 (2002-01-01), pages 1090 - 1096, XP002335364, ISSN: 1615-4150
SOICHI SAKANE ET AL: "ASYMMETRIC CYCLIZATION OF UNSATURATED ALDEHYDES CATALYZED BY A CHIRAL LEWIS ACID", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 26, no. 45, 1 January 1985 (1985-01-01), pages 5535 - 5538, XP007911907, ISSN: 0040-4039
TAKASHI MINO ET AL: "Hydrolysis of Beta,gamma-Unsaturated Aldehyde Dimethylhydrazones with Copper Dichloride: A New Synthesis of Lavandulol", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, EASTON.; US, vol. 62, no. 3, 1 January 1997 (1997-01-01), pages 734 - 735, XP007911906, ISSN: 0022-3263
OLGA B MOROZOVA ET AL: "1H and 13C Nuclear Polarization in Consecutive Biradicals during the Photolysis of 2,2,12,12-Tetramethylcyclododecanone", JOURNAL OF PHYSICAL CHEMISTRY. A, MOLECULES, SPECTROSCOPY,KINETICS, ENVIRONMENT AND GENERAL THEORY, WASHINGTON, DC, US, vol. 101, no. 4, 1 January 1997 (1997-01-01), pages 399 - 406, XP007911901, ISSN: 1089-5639
YONGSONG H ET AL: "Novel Unsaturated Triterpenoid Hydrocarbons from Sediments of Sacred Lake, Mt.Kenya, Kenya", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 52, no. 20, 13 May 1996 (1996-05-13), pages 6973 - 6982, XP004103940, ISSN: 0040-4020
MALLYABAEVA M I ET AL: "New method for the synthesis of (3R,7R)-hexahydrofarnesyl bromide based on the microwave-activated regioselective enolization of homochiral phytone", RUSSIAN CHEMICAL BULLETIN, KLUWER ACADEMIC PUBLISHERS-PLENUM PUBLISHERS, NE, vol. 56, no. 12, 20 September 2008 (2008-09-20), pages 2443 - 2447, XP019648896, ISSN: 1573-9171
ODINOKOV V N ET AL: "New Enantiospecific Synthesis of (+)-(2R,6R)-(+)-2,6,10-Trimethylunde can-1-ol for Constructing the Side Chain of Natural (2R,4'R,8'R)-(+)-[alpha]-Tocopherol (Vitamin E)", DOKLADY CHEMISTRY, KLUWER ACADEMIC PUBLISHERS-PLENUM PUBLISHERS, NE, vol. 403, no. 4-6, 1 August 2005 (2005-08-01), pages 144 - 147, XP019296097, ISSN: 1608-3113
HIRD NICHOLAS W ET AL: "The total synthesis of 10-(R,S)-C30 botryococcene and botryococcane and a new synthesis of a general intermediate to the botryococcene family", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 30, no. 36, 1 January 1989 (1989-01-01), pages 4867 - 4870, XP002472023, ISSN: 0040-4039
UEMOTO K ET AL: "Prenyl and geranyl phenyl sulfone, a new carbon nucleophile for Mitsunobu-type alkylation", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 42, no. 5, 29 January 2001 (2001-01-29), pages 905 - 907, XP004314714, ISSN: 0040-4039
EVANS DAVID A ET AL: "Synthetic studies in the lysocellin family of polyether antibiotics. The total synthesis of ferensimyc in B", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, NEW YORK, USA, vol. 113, no. 20, 1 January 1991 (1991-01-01), pages 7613 - 7630, XP002962307, ISSN: 0002-7863
POPPE L ET AL: "CONVENIENT SYNTHETIC ROUTE TO (+)-FARANAL AND (+)-13-NORFARANAL THE TRAIL PHEROMONE OF PHARAOH'S ANT AND ITS CONGENER", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 44, no. 5, 1 January 1988 (1988-01-01), pages 1477 - 1487, XP002034539, ISSN: 0040-4020
NOAL COHEN AND BEATRICE SCHAER: "Synthesis of (2RS,4'R,8'R )-a-Tocopherol and Related Compounds via a 2-Chlorochroman", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, EASTON.; US, vol. 57, no. 21, 1 January 1992 (1992-01-01), pages 5783 - 5785, XP007911926, ISSN: 0022-3263
DIETMAR APPELHANS ET AL: "Syntheses with Aliphatic Dialdehydes, XLVI. Synthesis and Reactions of 2,2-Dialkyl-Substituted Malonaldehydes and Their Semi(Ethylene Acetals)", LIEBIGS ANNALEN: ORGANIC AND BIOORGANIC CHEMISTRY, VCH PUBLISHERS, US, vol. 11, 22 October 1997 (1997-10-22), pages 2385 - 2392, XP009129883, ISSN: 0947-3440
HIROSHI OHRUI ET AL: "Development of Highly Potent D-Glucosamine-Based Chiral Fluorescent Labeling Reagents and a Microwave-Assisted Beta-Selective Glycosidation of a Methyl Glycoside Reagent", BIOSCIENCE BIOTECHNOLOGY BIOCHEMISTRY, JAPAN SOCIETY FOR BIOSCIENCE, BIOTECHNOLOGY, AND AGROCHEMISTRY, TOKYO, JAPAN, vol. 69, no. 5, 1 May 2005 (2005-05-01), pages 1054 - 1057, XP007911909, ISSN: 0916-8451
PAULO H G ZARBIN ET AL: "SYNTHESIS AND BIOLOGICAL ACTIVITY OF METHYL 2,6,10-TRIMETHYLDODECANO ATE AND METHYL 2,6,10-TRIMETHYLTRIDECANOATE: MALE-PRODUCED SEXUAL PHEROMONES OF STINK BUGS Euschistus heros AND Piezodorus guildinii", JOURNAL OF CHEMICAL ECOLOGY, PLENUM PUBLISHING CORPORATION, US, vol. 26, no. 12, 1 January 2000 (2000-01-01), pages 2737 - 2746, XP007911904, ISSN: 0098-0331
ERWAN SAOUTER: "Natural and Synthetic Surfactants. Which one is better?", INTERNET CITATION, 23 October 2003 (2003-10-23), pages 13PP, XP007911908, Retrieved from the Internet
FRANCIS J MCQUILLIN AND DAVID GEORGE PARKER: "Complexing of terpenes with transition metals. Part V. Reactions of 3,7-dimethylocta-1,6-diene and of 7-methoxy-3,7-dimethyloct-1-ene with rhodium(III) and thallium(III)", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, CHEMICAL SOCIETY, LETCHWORTH; GB, vol. 20, 1 January 1975 (1975-01-01), pages 2092 - 2096, XP009130044, ISSN: 0300-922X
FOCA C M ET AL: "Hydroformylation of myrcene: metal and ligand effects in the hydroformylation of conjugated dienes", NEW JOURNAL OF CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, GB, vol. 27, 3 February 2003 (2003-02-03), pages 533 - 539, XP007911905, ISSN: 1144-0546
Attorney, Agent or Firm:
THE PROCTER & GAMBLE COMPANY (Global Patent Services299 East Sixth Street,Sycamore Building, 4th Floo, Cincinnati Ohio, US)
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