Methods of making high-weight esters, acids, and derivatives thereof

Patent metadata

Field	Value
Publication number	US-9856189-B2
Application number	US-201615186784-A
Country	US
Kind code	B2
Filing date	Jun 20, 2016
Priority date	Oct 9, 2012
Publication date	Jan 2, 2018
Grant date	Jan 2, 2018

Abstract

Methods and compositions are provided for refining natural oils and for producing high-weight esters, high-weight acids, and/or high-weight derivatives thereof, wherein the compositions are made by cross-metathesizing low-weight unsaturated esters or low-weight unsaturated acids having hydrocarbon chain lengths less than or equal to C24 with an olefin feedstock, thereby forming a metathesized product composition including high-weight esters or high-weight acids having hydrocarbon chain lengths greater than C18, wherein at least a portion of the hydrocarbon chain lengths in the metathesized product are larger than the hydrocarbon chain lengths in the starting feedstock.

First claim

What is claimed is:

1. A method of making high-weight esters, high-weight acids, or high-weight derivatives thereof, comprising:
providing a starting feedstock comprising unsaturated fatty acid esters or unsaturated fatty acids, wherein a majority of the fatty acid chain lengths in the feedstock are less than or equal to C24;
optionally hydrolyzing the unsaturated fatty acid esters in the starting feedstock to form a hydrolyzed feedstock comprising hydrolyzed unsaturated fatty acids;
optionally transesterifying the unsaturated fatty acid esters or the unsaturated fatty acids of the starting feedstock or the hydrolyzed unsaturated fatty acids of the hydrolyzed feedstock to form a transesterified feedstock comprising transesterified unsaturated fatty acid esters;
cross-metathesizing the unsaturated fatty acid esters or the unsaturated fatty acids of the starting feedstock, the hydrolyzed unsaturated fatty acids of the hydrolyzed feedstock, or the transesterified unsaturated fatty acid esters of the transesterified feedstock with an olefin feedstock in the presence of a metathesis catalyst, thereby forming a metathesized product comprising high-weight fatty acid esters or high-weight fatty acids having fatty acid chain lengths greater than C18, wherein at least a portion of the fatty acid chain lengths in the metathesized product are larger than the fatty acid chain lengths in the starting feedstock; and
either (i) reducing the high-weight fatty acid esters or the high-weight fatty acids to form a high-weight alcohol, or (ii) transesterifying the high-weight fatty acid esters or the high-weight fatty acids with an alcohol.

2. The method of claim 1 , comprising reducing the high-weight fatty acid esters or the high-weight fatty acids to form a high-weight alcohol.

3. The method of claim 2 , further comprising transesterifying the high-weight alcohol with a fatty acid ester.

4. The method of claim 3 , wherein the starting feedstock comprises an unsaturated fatty acid ester having an unsaturated carbon-carbon bond at the C9-C10 position of the unsaturated fatty acid ester, wherein the olefin feedstock comprises a mixture of C16-C26 alpha-olefins, such that the metathesized product comprises a C24-C34 fatty acid ester, which is reduced to a C24-C34 alcohol, which is reacted with a C16-C18 fatty acid methyl ester, thereby forming a C40-C52 high-weight ester composition.

5. The method of claim 4 , further comprising blending the C40-C52 high-weight ester composition with a hydrocarbon feedstock and a free fatty acid feedstock, thereby forming a beeswax-like composition.

6. The method of claim 1 , comprising transesterifying the high-weight fatty acid esters or the high-weight fatty acids with an alcohol to form transesterified high-weight fatty acid esters.

7. The method of claim 6 , wherein the starting feedstock comprises an unsaturated fatty acid ester having an unsaturated carbon-carbon bond at the C9-C10 position of the unsaturated fatty acid ester, wherein the olefin feedstock comprises a mixture of C16-C26 alpha-olefins, such that the metathesized product comprises a C24-C34 fatty acid ester, which is transesterified to a transesterified C24-C34 fatty acid, which is reacted with a C16-C18 alcohol, thereby forming a C40-C52 high-weight ester composition.

8. The method of claim 7 , further comprising blending the C40-C52 high-weight ester composition with a hydrocarbon feedstock and a free fatty acid feedstock, thereby forming a beeswax-like composition.

9. The method of claim 1 , further comprising at least partially hydrogenating the high-weight fatty acid esters or the high-weight fatty acids.

Assignees

• Elevance Renewable Sciences

Inventors

• Firth Bruce
• Pease Brian M
• Ilseman Alexander D
• Zopp Garrett
• Murphy Timothy A
• Weitkamp Robin
• Morie-Bebel Michelle

Classifications

• C10G3/42 Primary

  Catalytic treatment · CPC title

• C10L1/026

  for compression ignition · CPC title

• C07C67/02

  by interreacting ester groups, i.e. transesterification · CPC title

• C10G2300/1088

  Olefins · CPC title

• C10G2400/04

  Diesel oil · CPC title