Method for preparing a lower alkyl ester product from vegetable oil

• US 6,127,560 A
• Filed: 12/29/1998
• Issued: 10/03/2000
• Est. Priority Date: 12/29/1998
• Status: Expired due to Term

• Current Assignee: REG Biofuels LLC (Chevron Corp.)
• Original Assignee: West Central Cooperative
• Inventors: Stidham, William D., Danzer, Myron F., Seaman, Donald W.
• Primary Examiner(s): Carr, Deborah D.
• Application Number:
  US09/223,623
• Time in Patent Office: 644 Days
• Field of Search: 554/167, 554/169, 426/417
• US Class Current: 554/167
• CPC Class Codes: C07C 67/03 by reacting an ester group with a hydroxy group
• CPC Class Codes: C07C 69/52 Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
• CPC Class Codes: C11C 3/003 by esterification of fatty acids with alcohols C11C3/02 takes precedence
• CPC Class Codes: C11C 3/04 by esterification of fats or fatty oils

Abstract

Comminuted soybeans are heated to high temperatures to condition the soybean oil contained therein. The soybean oil is extracted and filtered to remove solid fines, and then degummed and bleached. The prepared oil is introduced into a stirred reactor where lower aliphatic monohydric alcohol and an alkaline catalyst is introduced. Alcoholysis proceeds to virtual completion. A lower alkyl alcohol ester phase is separated out and washed with water to remove traces of unreacted alcohol and the alkaline catalyst.

Claims

1. A method for preparing lower alkyl esters of soybean oil fatty acids by an alcoholysis reaction of the soybean fatty acid triglycerides with a lower alcohol which comprises the successive steps of:

a) comminuting the raw soybeans to crack open their hulls and shatter their kernels;

b) heating the comminuted soybeans in a high-temperature reactor to elevated temperatures in the range of 235 to 350°

F.;

c) maintaining the soybeans at the elevated temperatures for a period of 1 to 60 minutes;

d) partially removing the oil contained in the soybeans by mechanical means;

e) degumming the crude soybean oil to reduce the concentration of phospholipid in the oil;

f) bleaching the degummed soybean oil to further reduce gums and improve color of the oil;

g) esterifying the fatty acid glycerides of the soybean oil by an alcoholysis reaction with a lower alcohol in the presence of an alkali catalyst to form fatty acid alcohol esters and glycerine, the conversion of the fatty acid glyceride being in the range of 90 to 99.5%

h) separating the glycerine from the crude fatty acid esterification products by settling or other mechanical means;

i) washing, in one or more steps, the crude fatty acid esterification products by trickling water through the products and allowing the mix of water and fatty acid esterification products to separate into two phases, washed and purified fatty acid esterification product and a water phase containing water, contaminants such as glycerine and unreacted lower alcohol and impurities from the soybean oil used.

2. A method for preparing lower alkyl fatty acid esters from soybean oil according to claim 1 in which the lower alcohol is methyl alcohol.

3. A method for preparing lower alkyl fatty acid esters from soybean oil according to claim 1 in which the alkali catalyst is substantially anhydrous sodium hydroxide.

4. A method for preparing lower alkyl fatty acid esters from soybean oil according to claim 1 in which the alcoholysis reaction in the reactor takes place at temperatures in the range of 140 to 200°

F.

5. A method for preparing lower alkyl fatty acid esters from soybean oil according to claim 1 in which the glycerine produced is purified by coalescing the dispersed alkyl fatty acid ester-alkyl alcohol phase into a continuous phase by means of a coalescing filter.

6. A method for preparing lower alkyl fatty acid esters from soybean oil according to claim 1 in which the methyl soyate product is washed in a counter-current washing column in which the methyl soyate product and the wash water in the form of droplets move in a counter-current fashion.

7. A method for preparing lower alkyl esters of soybean oil fatty acids using an alcoholysis reaction of the soybean oil fatty acid glycerides with a lower alcohol which comprises the successive steps of:

a) esterifying the fatty acid glycerides of the soybean oil by an alcoholysis reaction with a lower alcohol in the presence of an alkali catalyst to form fatty acid alcohol esters and glycerine, the conversion of the fatty acid glyceride being in the range of 90 to 99.5%;

b) separating the glycerine from the crude fatty acid esterification products by settling or other mechanical means;

c) washing, in one or more steps, the crude fatty acid esterification products by trickling water through the products and allowing the mix of water and fatty acid esterification products to separate into two phases, washed and purified fatty acid esterification product and a water phase containing water, contaminants such as glycerine and unreacted lower alcohol and impurities from the soybean oil used.

8. A method for producing lower alkyl esters of soy bean oil fatty acids according to claim 7 in which the lower alcohol is methyl alcohol.

9. A method for producing lower alkyl esters of soybean oil fatty acids according to claim 7 in which the alkaline catalyst is substantially anhydrous sodium hydroxide.

10. A method for producing lower alkyl esters of soybean oil fatty acids according to claim 7 in which the alcoholysis reaction in the reactor takes place at temperatures in the range of 140 to 200°

F.

11. A method for preparing lower alkyl fatty acid esters from soybean oil according to claim 7 in which the glycerine produced is purified by coalescing the dispersed alkyl fatty acid ester-lower alkyl alcohol phase into a continuous phase by means of a coalescing filter.

12. A method for preparing lower alkyl fatty acid esters from soybean oil according to claim 7 in which the methyl soyate produced is washed in a counter current washing column in which the methyl soyate product and the wash water in the form of droplets flow in a counter current fashion.

13. A method for preparing lower alkyl esters of soybean oil fatty acids, comprising the step of:

heating comminuted soybeans to a temperature of at least 235°

F. for up to 60 minutes to condition soybean oil contained therein;

mechanically removing soybean oil from the soybean;

esterifying the fatty acid glycerides of the soybean oil by an alcoholysis reaction with a lower alcohol in the presence of an alkali catalyst to form fatty acid alcohol esters and glycerine;

separating the glycerine from the fatty acid alcohol esters;

trickling water through the fatty acid alcohol esters; and

separating washed and purified fatty acid alcohol ester from a water phase containing water, contaminants and impurities.