Process for the synthesis of unsaturated alcohols

Maughon, Bob R.; Burdett, Kenneth A.; Lysenko, Zenon

Process for the synthesis of unsaturated alcohols

Patent · Tue Feb 13 04:00:00 EST 2007

OSTI ID:1176105

Maughon, Bob R.; Burdett, Kenneth A.; Lysenko, Zenon

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.

Research Organization:: Dow Global Technologies Inc., Midland, MI (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: FC07-01ID14213

Assignee:: Dow Global Technologies Inc. (Midland, MI)

Patent Number(s):: 7,176,336

Application Number:: 10/940,403

OSTI ID:: 1176105

Country of Publication:: United States

Language:: English

References (12)

A Convenient Method for Removing All Highly-Colored Byproducts Generated during Olefin Metathesis Reactions Paquette, Leo A.; Schloss, Jeffrey D.; Efremov, Ivan Organic Letters, Vol. 2, Issue 9 https://doi.org/10.1021/ol000036w	journal	May 2000
Polymers and surfactants on the basis of renewable resources Warwel, Siegfried; Brüse, Falk; Demes, Christoph Chemosphere, Vol. 43, Issue 1, p. 39-48 https://doi.org/10.1016/S0045-6535(00)00322-2	journal	April 2001
Ruthenium-catalyzed metathesis of vegetable oils Refvik, M. D.; Larock, R. C.; Tian, Q. Journal of the American Oil Chemists' Society, Vol. 76, Issue 1 https://doi.org/10.1007/s11746-999-0053-z	journal	January 1999
A Convenient Method for the Efficient Removal of Ruthenium Byproducts Generated during Olefin Metathesis Reactions Ahn, Yu Mi; Yang, KyoungLang; Georg, Gunda I. Organic Letters, Vol. 3, Issue 9 https://doi.org/10.1021/ol010045k	journal	May 2001
New Syntheses with Oils and Fats as Renewable Raw Materials for the Chemical Industry Biermann, Ursula; Friedt, Wolfgang; Lang, Siegmund Angewandte Chemie International Edition, Vol. 39, Issue 13 https://doi.org/10.1002/1521-3773(20000703)39:13<2206::AID-ANIE2206>3.0.CO;2-P	journal	July 2000
Purification technique for the removal of ruthenium from olefin metathesis reaction products Maynard, Heather D.; Grubbs, Robert H. Tetrahedron Letters, Vol. 40, Issue 22, p. 4137-4140 https://doi.org/10.1016/S0040-4039(99)00726-1	journal	May 1999
Olefin metathesis in non-degassed solvent using a recyclable, polymer supported alkylideneruthenium Dowden, James; Savović, Jelena Chemical Communications, Issue 1 https://doi.org/10.1039/b007304k	journal	January 2001
A Recyclable Ru-Based Metathesis Catalyst Kingsbury, Jason S.; Harrity, Joseph P. A.; Bonitatebus, Peter J. Journal of the American Chemical Society, Vol. 121, Issue 4 https://doi.org/10.1021/ja983222u	journal	February 1999
Catalytic activity and selectivity of Ru( CHPh)Cl 2 (PCy 3 ) 2 in the metathesis of linear alkenes Buchowicz, W.; Mol, J. C. Journal of Molecular Catalysis A: Chemical, Vol. 148, Issue 1-2 https://doi.org/10.1016/S1381-1169(99)00145-4	journal	December 1999
Renewable Monomer Feedstocks via Olefin Metathesis: Fundamental Mechanistic Studies of Methyl Oleate Ethenolysis with the First-Generation Grubbs Catalyst Burdett, Kenneth A.; Harris, Lori D.; Margl, Peter Organometallics, Vol. 23, Issue 9 https://doi.org/10.1021/om0341799	journal	April 2004
A convenient catalyst system employing RuCl3 or RuBr3 for metathesis of acyclic olefins Nubel, P. O.; Hunt, C. L. Journal of Molecular Catalysis A: Chemical, Vol. 145, Issue 1-2 https://doi.org/10.1016/S1381-1169(99)00150-8	journal	September 1999
Synthesis and metathesis reactions of a phosphine-free dihydroimidazole carbene ruthenium complex Gessler, Simon; Randl, Stefan; Blechert, Siegfried Tetrahedron Letters, Vol. 41, Issue 51 https://doi.org/10.1016/S0040-4039(00)01808-6	journal	December 2000

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