Process for the synthesis of unsaturated alcohols
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.
- Inventors:
- Issue Date:
- Research Org.:
- Dow Global Technologies Inc., Midland, MI (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1176105
- Patent Number(s):
- 7176336
- Application Number:
- 10/940,403
- Assignee:
- Dow Global Technologies Inc. (Midland, MI)
- Patent Classifications (CPCs):
-
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
- DOE Contract Number:
- FC07-01ID14213
- Resource Type:
- Patent
- Resource Relation:
- Patent File Date: 2004 Sep 14
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Maughon, Bob R., Burdett, Kenneth A., and Lysenko, Zenon. Process for the synthesis of unsaturated alcohols. United States: N. p., 2007.
Web.
Maughon, Bob R., Burdett, Kenneth A., & Lysenko, Zenon. Process for the synthesis of unsaturated alcohols. United States.
Maughon, Bob R., Burdett, Kenneth A., and Lysenko, Zenon. Tue .
"Process for the synthesis of unsaturated alcohols". United States. https://www.osti.gov/servlets/purl/1176105.
@article{osti_1176105,
title = {Process for the synthesis of unsaturated alcohols},
author = {Maughon, Bob R. and Burdett, Kenneth A. and Lysenko, Zenon},
abstractNote = {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.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Tue Feb 13 00:00:00 EST 2007},
month = {Tue Feb 13 00:00:00 EST 2007}
}
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.
Works referenced in this record:
A convenient catalyst system employing RuCl3 or RuBr3 for metathesis of acyclic olefins
journal, September 1999
- Nubel, P. O.; Hunt, C. L.
- Journal of Molecular Catalysis A: Chemical, Vol. 145, Issue 1-2
Synthesis and metathesis reactions of a phosphine-free dihydroimidazole carbene ruthenium complex
journal, December 2000
- Gessler, Simon; Randl, Stefan; Blechert, Siegfried
- Tetrahedron Letters, Vol. 41, Issue 51
Catalytic activity and selectivity of Ru( CHPh)Cl 2 (PCy 3 ) 2 in the metathesis of linear alkenes
journal, December 1999
- Buchowicz, W.; Mol, J. C.
- Journal of Molecular Catalysis A: Chemical, Vol. 148, Issue 1-2
A Recyclable Ru-Based Metathesis Catalyst
journal, February 1999
- Kingsbury, Jason S.; Harrity, Joseph P. A.; Bonitatebus, Peter J.
- Journal of the American Chemical Society, Vol. 121, Issue 4
A Convenient Method for Removing All Highly-Colored Byproducts Generated during Olefin Metathesis Reactions
journal, May 2000
- Paquette, Leo A.; Schloss, Jeffrey D.; Efremov, Ivan
- Organic Letters, Vol. 2, Issue 9
Olefin metathesis in non-degassed solvent using a recyclable, polymer supported alkylideneruthenium
journal, January 2001
- Dowden, James; Savović, Jelena
- Chemical Communications, Issue 1
Purification technique for the removal of ruthenium from olefin metathesis reaction products
journal, May 1999
- Maynard, Heather D.; Grubbs, Robert H.
- Tetrahedron Letters, Vol. 40, Issue 22, p. 4137-4140
A Convenient Method for the Efficient Removal of Ruthenium Byproducts Generated during Olefin Metathesis Reactions
journal, May 2001
- Ahn, Yu Mi; Yang, KyoungLang; Georg, Gunda I.
- Organic Letters, Vol. 3, Issue 9
Polymers and surfactants on the basis of renewable resources
journal, April 2001
- Warwel, Siegfried; Brüse, Falk; Demes, Christoph
- Chemosphere, Vol. 43, Issue 1, p. 39-48
Renewable Monomer Feedstocks via Olefin Metathesis: Fundamental Mechanistic Studies of Methyl Oleate Ethenolysis with the First-Generation Grubbs Catalyst
journal, April 2004
- Burdett, Kenneth A.; Harris, Lori D.; Margl, Peter
- Organometallics, Vol. 23, Issue 9
Ruthenium-catalyzed metathesis of vegetable oils
journal, January 1999
- Refvik, M. D.; Larock, R. C.; Tian, Q.
- Journal of the American Oil Chemists' Society, Vol. 76, Issue 1