Granted Patent B2

US 8,598,377 · App. 13/125,387 · Granted Dec 3, 2013

Inventors: Eckhard Weidner (Bochum, DE); Axel Kraft (Oer-Erkenschwick, DE); Anna Grevé (Bochum, DE); Reinhard Broucek (Aschaffenburg, DE)

Assignees: Fraunhofer-Gesellschaft zur Foerderung der angewandten Forschung e.V.; Balchem Corporation

Abstract

Claims (18)

1. A method for producing fatty acid esters of monovalent or polyvalent alcohols by means of a catalyst, comprising reacting fat and/or oil of biogenic origin with monovalent and/or polyvalent alcohols in the presence of a catalyst, wherein the catalyst is a hydroxy-functional quaternary ammonium compound of the following formula (I):

in which R1, R2 and R3 are equal or different and each represents an unsubstituted straight-chain alkyl residue having 1 to 6 carbon atoms, and

R is a straight-chain or branched hydroxyalkyl, hydroxyalkenyl or hydroxyalkynyl residue having 1 to 8 carbon atoms.

2. The method according to claim 1 , wherein R is a straight-chain hydroxyalkyl residue having 1 to 12 carbon atoms.

3. The method according to claim 1 , wherein R is 2-hydroxyethyl.

4. The method according to claim 1 , wherein choline or a salt thereof is used as the catalyst.

5. The method according to claim 1 , wherein the catalyst is used in an amount between 0.01 and 4.0% by weight, based on the weight of the employed fat and/or oil of biogenic origin.

6. The method according to claim 1 , wherein the monovalent alcohol is selected from the group consisting of methanol, ethanol, n-propanol, isopropanol, butanol and mixtures thereof and the polyvalent alcohol is a divalent alcohol selected from the group consisting of propanediol, butanediol and mixtures thereof.

7. The method according to claim 1 , wherein the employed fat and/or oil of biogenic origin contains less than 0.5% by weight of fatty acids.

8. The method according to claim 1 , wherein the molar ratio of the monovalent and/or polyvalent alcohol to the fat and/or oil of biogenic origin is at least 6:1.

9. The method according to claim 1 , further comprising the purification of the formed fatty acid ester of monovalent or polyvalent alcohols by separation of the by-products formed.

10. The method according to claim 9 , wherein the by-product formed is a glycerol product, comprising a catalyst-containing glycerol fraction.

11. The method according to claim 1 , wherein the hydroxy-functional quaternary ammonium compound used as the catalyst is employed in the form of a glycerol fraction which is obtainable according to a method as defined in claim 1 and in which the hydroxy-functional quaternary ammonium compound used as the catalyst is enriched.

12. A method of preparing a feed additive for use in the animal feed industry, the feed additive including fatty acid esters of monovalent or polyvalent alcohols produced by means of a catalyst, the method comprising:

reacting fat and/or oil of biogenic origin with monovalent and/or polyvalent alcohols in the presence of a catalyst, wherein the catalyst is a hydroxy-functional quaternary ammonium compound of the following formula (I):

in which R1, R2 and R3 are equal or different and each represents an unsubstituted straight-chain alkyl residue having 1 to 6 carbon atoms, and

R is a straight-chain or branched hydroxyalkyl, hydroxyalkenyl or hydroxyalkynyl residue having 1 to 8 carbon atoms;

purifying of the formed fatty acid esters of monovalent or polyvalent alcohols by separating the catalyst containing the glycerol faction as a by-product, wherein the catalyst is used in an amount of 0.01 to 2.0 percent by weight, based on the weight of the employed fat and/or oil of biogenic origin.

Assignments (9)

Priority Claims (1)

Continuity (1)