Title: Methods of refining and producing dibasic esters and acids from natural oil feedstocks

Abstract

Methods are provided for refining natural oil feedstocks and producing dibasic esters and/or dibasic acids. The methods comprise reacting a terminal olefin with an internal olefin in the presence of a metathesis catalyst to form a dibasic ester and/or dibasic acid. In certain embodiments, the olefin esters are formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having olefin esters.

Inventors:

Snead, Thomas E; Cohen, Steven A; Gildon, Demond L

Issue Date:

2015-04-07

Research Org.:

Elevance Renewable Sciences, Inc., Woodridge, IL (United States)

Sponsoring Org.:

USDOE

OSTI Identifier:

1177513

Patent Number(s):

9000246

Application Number:

13/647,809

Assignee:

Elevance Renewable Sciences, Inc. (Woodridge, IL)

Patent Classifications (CPCs):

C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10G - CRACKING HYDROCARBON OILS

C - CHEMISTRY C11 - ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES C11C - FATTY ACIDS FROM FATS, OILS OR WAXES

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C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10G - CRACKING HYDROCARBON OILS

C10G2300/308 - Gravity, density, e.g. API

C - CHEMISTRY C11 - ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES C11C - FATTY ACIDS FROM FATS, OILS OR WAXES

C11C3/00 - Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y02 - TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE Y02P - CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

Y02P20/582 - of unreacted starting or intermediate materials

C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10L - FUELS NOT OTHERWISE PROVIDED FOR

C10L2200/0476 - Biodiesel, i.e. defined lower alkyl esters of fatty acids first generation biodiesel

C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10G - CRACKING HYDROCARBON OILS

C10G45/00 - Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
C10G45/58 - to change the structural skeleton of some of the hydrocarbon content without cracking the other hydrocarbons present, e.g. lowering pour point
C10G50/00 - Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation
C10G2400/08 - Jet fuel

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C67/333 - by isomerisation

C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10G - CRACKING HYDROCARBON OILS

C10G65/043 - {at least one step being a change in the structural skeleton}
C10G2400/02 - Gasoline
C10G2400/04 - Diesel oil

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C67/475 - by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of [IMAGE cpc-sch-C07C-0963.gif] groups between different molecules

C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10L - FUELS NOT OTHERWISE PROVIDED FOR

C10L1/026 - {for compression ignition}

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C69/593 - Dicarboxylic acid esters having only one carbon-to-carbon double bond

C - CHEMISTRY C11 - ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES C11C - FATTY ACIDS FROM FATS, OILS OR WAXES

C11C3/003 - {by esterification of fatty acids with alcohols

C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10G - CRACKING HYDROCARBON OILS

C10G2300/1018 - of animal origin
C10G2400/22 - Higher olefins
C10G2300/307 - Cetane number, cetane index

C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10L - FUELS NOT OTHERWISE PROVIDED FOR

C10L2200/0469 - Renewables or materials of biological origin

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y02 - TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE Y02P - CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

Y02P30/20 - Bio-feedstock

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C67/03 - by reacting an ester group with a hydroxy group

C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10G - CRACKING HYDROCARBON OILS

C10G2300/30 - Physical properties of feedstocks or products
C10G2400/20 - C2-C4 olefins

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C69/533 - Monocarboxylic acid esters having only one carbon-to-carbon double bond

C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10G - CRACKING HYDROCARBON OILS

C10G2300/1088 - Olefins

C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10L - FUELS NOT OTHERWISE PROVIDED FOR

C10L1/08 - for compression ignition

C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10G - CRACKING HYDROCARBON OILS

C10G2300/44 - Solvents

C - CHEMISTRY C11 - ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES C11B - PRODUCING

C11B3/00 - Refining fats or fatty oils

C - CHEMISTRY C10 - PETROLEUM, GAS OR COKE INDUSTRIES C10G - CRACKING HYDROCARBON OILS

C10G2300/1014 - of vegetal origin
C10G2300/301 - Boiling range
C10G3/42 - {Catalytic treatment}

C - CHEMISTRY C11 - ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES C11B - PRODUCING

C11B3/02 - by chemical reaction {

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DOE Contract Number:  

EE0002872/001

Resource Type:

Patent

Resource Relation:

Patent File Date: 2012 Oct 09

Country of Publication:

United States

Language:

English

Subject:

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 09 BIOMASS FUELS