Process for the synthesis of unsaturated alcohols

Details Process for the synthesis of unsaturated alcohols Process for the synthesis of unsaturated alcohols

2007-02-13

2007-02-13

Davis, Brian (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

C568S857000, C568S875000, C568S877000, C568S909500

Reexamination Certificate

active

10940403

ABSTRACT:
A process of preparing an unsaturated alcohol (olefin alcohol), such as, a homo-allylic mono-alcohol or homo-allylic polyol, involving protecting a hydroxy-substituted unsaturated fatty acid or fatty acid ester, such as methyl ricinoleate, derived from a seed oil, to form a hydroxy-protected unsaturated fatty acid or fatty acid ester; homo-metathesizing or cross-metathesizing the hydroxy-protected unsaturated fatty acid or fatty acid ester to produce a product mixture containing a hydroxy-protected unsaturated metathesis product; and deprotecting the hydroxy-protected unsaturated metathesis product under conditions sufficient to prepare the unsaturated alcohol. Preferably, methyl ricinoleate is converted by cross-metathesis or homo-metathesis into the homo-allylic mono-alcohol 1-decene-4-ol or the homo-allylic polyol 9-octadecene-7,12-diol, respectively.

REFERENCES:
patent: 4545941 (1985-10-01), Rosenburg
patent: 4560792 (1985-12-01), Banasiak
patent: 4772758 (1988-09-01), Kaufhold
patent: 4943397 (1990-07-01), Johnson
patent: 5143885 (1992-09-01), Warwel et al.
patent: 5218131 (1993-06-01), Warwel et al.
patent: 5312940 (1994-05-01), Grubbs et al.
patent: 5342985 (1994-08-01), Herrmann et al.
patent: 5352812 (1994-10-01), Feldman et al.
patent: 5539060 (1996-07-01), Tsunogae et al.
patent: 5932664 (1999-08-01), Chen et al.
patent: 6060572 (2000-05-01), Gillis et al.
patent: 6111149 (2000-08-01), Schwab et al.
patent: 6156692 (2000-12-01), Nubel et al.
patent: 6191324 (2001-02-01), Guram et al.
patent: 6197894 (2001-03-01), Sunaga et al.
patent: 6369283 (2002-04-01), Guram et al.
patent: 6635768 (2003-10-01), Herrmann et al.
patent: A1-281594 (1990-08-01), None
patent: 4107056 (1992-09-01), None
patent: 100 41 345 (2002-03-01), None
patent: 0 084 437 (1983-07-01), None
patent: 0 099 572 (1984-02-01), None
patent: 0 328 230 (1989-08-01), None
patent: J 56 077243 (1981-06-01), None
patent: J 03 066725 (1991-03-01), None
patent: WO 91/14665 (1991-10-01), None
patent: WO 93/20111 (1993-10-01), None
patent: WO 96/04289 (1996-02-01), None
patent: WO 97/06185 (1997-02-01), None
patent: WO 99/00397 (1999-01-01), None
patent: WO 99/22866 (1999-05-01), None
patent: WO 00/15339 (2000-03-01), None
patent: WO 00/58322 (2000-10-01), None
patent: WO 00/71554 (2000-11-01), None
patent: WO 02/076920 (2002-10-01), None
patent: WO 03/093215 (2003-11-01), None
patent: WO 04/037754 (2004-05-01), None
Database CAPLUS on STN, Acc. No. 1992:567369, Brodowsky et al., Journal of Biological Chemistry (1992), 267(21), p. 14738-45 (abstract).
Ahn, Yu Mi et al., “A Convenient Method for the Efficient Removal of Ruthenium Byproducts Generated During Olefin Metathesis Reactions”, Organic Letters, vol. 3, pp. 1411-1413 (2001).
Biermann, Ursula et al., “New Synthesis with Oils and Fats as Renewable Raw Materials for the Chemical Industry”, Angewandte Chemie Int. Ed., vol. 39, pp. 2207-2224 (2000).
Buchowicz, W. et al., “Catalytic Activity and Selectivity of Ru(=CHPh)Cl2(PCy3)2in the Metathesis of Linear Alkenes”, Journal of Molecular Catalysis A; Chemical, vol. 148, pp. 97-103 (1999).
Derwent Abstract, AN 1991-015326 (DD 281594) (1991).
Dowden, James et al., “Olefin Metathesis in Non-Degassed Solvent Using a Recyclable, Polymer Supported Alkylideneruthenium”, Chemical Communications, pp. 37-38 (2001).
Gessler, Simon et al., “Synthesis and Metathesis Reactions of a Phosphine-Free Dihydroimidazole carbine Ruthenium Complex”, Tetrahedron Letters, vol. 41, pp. 9973-9976 (2000).
Kingsbury, Jason et al., “A Recyclable Ru-Based Metathesis Catalyst”, Journal of the American Chemical Society, vol. 121, pp. 791-799 (1999).
Mandelli, Dalmo et al., “Ethenolysis of Esters of Vegetable Oils: Effect of B2O3Addition to Re2O7/SiO2O3-SnBu4and CH3ReO3/SiO2Al2Al2O3Metathesis Catalysts”, Journal of the American Oil Chemical Society, vol. 73, pp. 229-232 (1996).
Maynard, Heather et al., “Purification Technique for the Removal of Ruthenium from Olefin Metathesis Reaction Products”, Tetrahedron Letters, vol. 40, pp. 4137-4140 (1999).
Nubel, P.O. et al., “A Convenient Catalyst System Employing RuCl3or RuBr3for Metathesis of Acyclic Olefins”, Journal of Molecular Catalysis A: Chemical, vol. 145, pp. 323-327 (1999).
Paquette, Leo et al., “A Convenient Method for Removing All Highly-Colored Byproducts Generated During Olefin Metathesis Reactions”, Organic Letters, vol. 2, pp. 1259-1261 (2000).
Refvik, M.D. et al., “Ruthenium-Catalyzed Metathesis of Vegetable Oils”, Journal of the American Oil Chemical Society, vol. 76, pp. 93-98 (1999).
Warwel, Siegfried et al., “Polymers and Surfactants on the Basis of Renewable Resources”, CHEMOSPHERE, vol. 43, pp. 39-48 (2001).
Yao, Qingwei, “A Soluble Polymer-Bound Ruthenium Carbene Complex: A Robust and Reusable Catalyst for Ring-Closing Olefin Metathesis”, Angewandte Chemie Intl. Ed., vol. 39, pp. 3896-3898 (2000); (German version: Yao; Qingwei, “Ein löslicher, polymergebundener rutheniumcarbenkomplex: ein robuster und wiederverwendbarer Katalysator für Ringschluss-Olefinmetathesen”, Angewandte Chemie, vol. 112, pp. 4060-4063 (2000).
“Integrated Chemical Processes for Industrial Utilization of Seed Oils”, filed in the United States of America on Apr. 17, 2003, U.S. Appl. No. 10/508,805; Applicant; Zenon Lysenko, et al.
“Metathesis of Unsaturated Fatty Acid Esters or Unsaturated Fatty Acids with Lower Olefins”, filed in the United States of America on Feb. 27, 2002, U.S. Appl. No. 10/469,321; Applicant; Thomas H. Newman, et al.
Burdett, Kenneth A., “Renewable Monomer Feedstocks via Olefin Metathesis: Fundamental Mechanistic Studies of Methyl Oleate Ethenolysts with the First-Generation Grubbs Catalyst”, ORGANOMETALLICS, vol. 23, pp. 2027-2047, 2004.
Burdett, Kenneth A., et al., “Stabilization of Olefin Metathesis Product Mixtures”, filed in the United States of America on Mar. 21, 2005, U.S. Appl. No. 10/528,472.

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