US 12,030,852 B2
Method for producing fatty alcohol esters of hydroxycarboxylic acids
Dirk Lochmann, Witten (DE); Sebastian Reyer, Witten (DE); and Michael Stehr, Witten (DE)
Assigned to IOI Oleo GmbH, (DE)
Appl. No. 17/378,967
Filed by IOI Oleo GmbH, Witten (DE)
PCT Filed Jan. 23, 2019, PCT No. PCT/EP2019/051546
§ 371(c)(1), (2) Date Jul. 19, 2021,
PCT Pub. No. WO2020/147982, PCT Pub. Date Jul. 23, 2020.
Claims priority of application No. PCT/EP2019/051125 (WO), filed on Jan. 17, 2019.
Prior Publication US 2023/0159430 A1, May 25, 2023
Int. Cl. C07C 67/02 (2006.01); C07C 67/03 (2006.01); C07C 67/08 (2006.01); C07C 69/675 (2006.01); C07C 69/732 (2006.01); C12P 7/62 (2022.01)
CPC C07C 69/675 (2013.01) [C07C 67/02 (2013.01); C07C 67/03 (2013.01); C07C 67/08 (2013.01); C07C 69/732 (2013.01); C12P 7/62 (2013.01); C12Y 301/01 (2013.01)] 14 Claims
 
1. A method for producing fatty alcohol esters of 3-hydroxybutyric acid,
(A) wherein, according to a first synthesis route (A), at least one compound of the general formula (Ia)
CH3—CH(OH)—CH2—C(O)OR1  (Ia)
wherein, in the general formula (Ia), the radical R1 represents hydrogen or C1-C4-alkyl,
is reacted with at least one fatty alcohol (II) selected from C10-C30-fatty alcohols,
wherein the reaction is carried out in the absence of any solvents,
wherein the reaction is carried out in the presence of an enzyme as a catalyst, wherein the catalyst is recycled after the reaction, and
wherein during the reaction, the compound according to the general formula (IVa)
R1—OH  (IVa)
is formed simultaneously, wherein, in general formula (IVa), the radical R1 represents hydrogen or C1-C4-alkyl, wherein the compound according to the general formula (IVa) is continuously withdrawn from the reaction;
or else
(B) wherein, according to a second synthesis route (B), which is alternative to synthesis route (A), at least one compound of the general formula (Ib)
CH3—CH(OR2)—CH2—C(O)—O—C(O)—CH2—CH(OR2)—CH3  (Ib)
wherein, in the general formula (Ib), the radical R2 represents an acyl group selected from an acetyl group of formula —C(O)—CH3 or a propionyl group of formula —C(O)—C2H5,
is reacted with at least one fatty alcohol (II) selected from C10-C30-fatty alcohols, followed by hydrolysis of the acyl group;
so that, as a reaction product (III), in each case a C10-C30-fatty alcohol ester of 3-hydroxybutyric acid is obtained.