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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:
; ;
Publication Date:
Research Org.:
Dow Global Technologies Inc., Midland, MI (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1176105
Patent Number(s):
7,176,336
Application Number:
10/940,403
Assignee:
Dow Global Technologies Inc. (Midland, MI) OSTI
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. doi:. 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}
}

Patent:

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  • A process is described for converting an alcohol and/or ether feed as hereinafter defined to a hydrocarbon mixture rich in olefins which comprises contacting, under conversion conditions at a conversion reaction temperature of from about 300/sup 0/ to 350/sup 0/C., a feed comprising one or more monohydric alcohols having from about 1 to about 4 carbon atoms, ethers derived therefrom, or mixtures of the alcohols and ethers, with a modified crystalline metalosilicate shape selective acidic zeolite. The metalosilicate is selected from the group consisting of aluminum, gallium, and mixtures thereof, and the zeolite, prior to modification and in the absencemore » of any coke deposited thereon, possesses: (a) the capability of catalyzing the alcohol and/or other conversion reaction; (b) a channel size and structure such as to permit (i) entry of the feed into the zeolite and diffusion to the active acid sites within the zeolite, and (ii) formation of olefin products within the zeolite and diffusion of the products out of the zeolite; and (c) hydrothermal stability at temperatures of at least about 290/sup 0/C. The modification of the zeolite is conducted in a manner sufficient to increase the catalyst life of the zeolite, relative to the absence of the modification when the zeolite is employed as a catalyst for the alcohol and/or ether conversion reaction.« less
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  • This patent describes a method of preparing a mixture of lower aliphatic alcohols which comprises reacting carbon monoxide and hydrogen in the presence of a sulfide-containing heavy metal catalyst under carbon monoxide-hydrogenation conditions. The catalyst consists of: (1) at least one sulfided heavy metal element selected from the group consisting of molybdenum; tungsten, and rhenium, (2) a sulfided heavy metal element form the group consisting of cobalt, iron, and nickel, (3) a promoter comprising an alkali or alkaline earth element in free or combined form, and optionally, (4) a support, the improvement which comprises improving the selectivity to the alcoholsmore » by treating the sulfided heavy metal elements with a nitrogen-containing base prior to treatment with the promoter, the nitrogen-containing base being selected from the group consisting of urea, dimethylolurea, cyanuric acid, melamine, melam, melem, and melon.« less
  • This patent describes a pumpable stabilized coal water slurry, having a coal content of at least about 50% by weight wherein at least 80% of the coal particles are about 200 mesh or finer, containing from about 0.01% to about 1% by weight of the slurry of a water soluble terpolymer of ethylacrylate (A), metacrylic acid (B) and a third monomer (C) selected from the group consisting of an unsaturated carboxylic acid ester of an alcohol and an ethoxylated carboxylic acid. The unsaturated carboxylic acid is a mono- or di- basic unsaturated carboxylic acid of 3 to 10 carbon atomsmore » selected from the group consisting of acrylic acid, methacrylic acid, itaconic acid, fumaric acid, and maleic acid.« less