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Title: 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
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 = {2007},
month = {2}
}

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Works referenced in this record:

A convenient catalyst system employing RuCl3 or RuBr3 for metathesis of acyclic olefins
journal, September 1999


Synthesis and metathesis reactions of a phosphine-free dihydroimidazole carbene ruthenium complex
journal, December 2000


Catalytic activity and selectivity of Ru( CHPh)Cl 2 (PCy 3 ) 2 in the metathesis of linear alkenes
journal, December 1999


A Recyclable Ru-Based Metathesis Catalyst
journal, February 1999


A Convenient Method for Removing All Highly-Colored Byproducts Generated during Olefin Metathesis Reactions
journal, May 2000


Olefin metathesis in non-degassed solvent using a recyclable, polymer supported alkylideneruthenium
journal, January 2001


Purification technique for the removal of ruthenium from olefin metathesis reaction products
journal, May 1999


A Convenient Method for the Efficient Removal of Ruthenium Byproducts Generated during Olefin Metathesis Reactions
journal, May 2001


Polymers and surfactants on the basis of renewable resources
journal, April 2001


Ruthenium-catalyzed metathesis of vegetable oils
journal, January 1999