Methods of Refining Natural Oil Feedstocks

Patent metadata

Field	Value
Publication number	US-2015240186-A1
Application number	US-201514590737-A
Country	US
Kind code	A1
Filing date	Jan 6, 2015
Priority date	Oct 12, 2009
Publication date	Aug 27, 2015
Grant date	—

Abstract

Methods are provided for refining natural oil feedstocks. The methods comprise reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters. In certain embodiments, the methods further comprise separating the olefins from the esters in the metathesized product. In certain embodiments, the methods further comprise hydrogenating the olefins under conditions sufficient to form a fuel composition. In certain embodiments, the methods further comprise transesterifying the esters in the presence of an alcohol to form a transesterified product.

First claim

1 - 31 . (canceled)

32 . A method of refining a natural oil, comprising:
providing (a) a feedstock comprising natural oil glycerides, and (b) low-molecular-weight alpha-olefins, wherein the low-molecular-weight alpha-olefins comprise 1-butene; cross-metathesizing the natural oil glycerides with the low-molecular-weight alpha-olefins in a metathesis reactor in the presence of a metathesis catalyst to provide a metathesized product comprising alpha-olefins and metathesized glycerides; separating at least a portion of the alpha-olefins of the metathesized product to provide a first stream comprising separated alpha-olefins; and recycling at least a portion of the separated alpha-olefins of the first stream to the metathesis reactor.

33 . The method of claim 32 , comprising treating the feedstock, prior to cross-metathesizing the natural oil glycerides with the low-molecular-weight alpha-olefins, to diminish catalyst poisons in the feedstock.

34 . The method of claim 33 , wherein the treating comprises chemically treating the feedstock through a chemical reaction with a reducing agent or a cation-inorganic base composition to diminish the catalyst poisons, wherein the reducing agent is selected from the group consisting of bisulfites, borohydrides, phosphines, thiosulfates, and phosphates.

35 . The method of claim 33 , wherein the treating comprises heating the feedstock to a temperature greater than 150° C. in the absence of oxygen.

36 . The method of claim 32 , wherein the metathesis catalyst is dissolved in a solvent.

37 . The method of claim 36 , wherein the solvent comprises toluene.

38 . The method of claim 32 , comprising transesterifying the metathesized glycerides of in the presence of an alcohol to provide a transesterified product comprising glycerin and fatty acid esters having no glycerin backbone.

39 . The method of claim 38 , comprising separating the glycerin from the transesterified product through a liquid-liquid separation; and, after separating the glycerin, washing the transesterified product; and, after the washing, drying the transesterified product.

40 . The method of claim 38 , comprising distilling the transesterified product to separate a specialty chemical composition, wherein the specialty chemical composition comprises a 9-decenoic acid ester, a 9-dodecenoic acid ester, or any combinations thereof.

41 . The method of claim 32 , wherein the natural oil glycerides comprise a natural oil triglyceride selected from the group consisting of vegetable oils, algae oils, animal fats, and combinations thereof.

42 . The method of claim 32 , wherein the natural oil glycerides comprise a vegetable oil selected from the group consisting of: canola oil, rapeseed oil, coconut oil, corn oil, cottonseed oil, olive oil, palm oil, peanut oil, safflower oil, sesame oil, soybean oil, sunflower oil, linseed oil, palm kernel oil, tung oil, jatropha oil, mustard oil, pennycress oil, camelina oil, castor oil, and combinations thereof.

43 . The method of claim 32 , wherein the natural oil glycerides comprise a vegetable oil selected from the group consisting of: soybean oil, palm oil, canola oil, and combinations thereof.

44 . The method of claim 38 , wherein the alcohol is methanol or ethanol.

45 . The method of claim 32 , wherein the portion of the separated alpha-olefins of the first stream recycled to the metathesis reactor comprises C2-C6 recycle alpha-olefins.

46 . The method of claim 32 , wherein the portion of the separated alpha-olefins of the first stream recycled to the metathesis reactor comprises C3-05 recycle alpha-olefins.

47 . The method of claim 32 , wherein the portion of the separated alpha-olefins of the first stream recycled to the metathesis reactor comprises C3-C8 recycle alpha-olefins.

Assignees

• Elevance Renewable Sciences

Inventors

• Cohen Steven A
• Luetkens Jr Melvin L
• Balakrishnan Chander
• Snyder Robert

Classifications

• C11C1/08 Primary

  Refining · CPC title

• Y02E50/10

  Biofuels, e.g. bio-diesel · CPC title

• C11C3/003

  by esterification of fatty acids with alcohols (C11C3/02 takes precedence) · CPC title

• C11B3/00

  Refining fats or fatty oils · CPC title

• C10L1/08

  for compression ignition · CPC title