US 12,467,015 B2
Method of making fatty acid esters
Axel Ingendoh, Odenthal (DE)
Assigned to REC Reliable Engineering Concepts GmbH, Stuttgart (DE)
Appl. No. 17/756,361
Filed by REC Reliable Engineering Concepts GmbH, Stuttgart (DE)
PCT Filed Nov. 26, 2020, PCT No. PCT/EP2020/083546
§ 371(c)(1), (2) Date May 23, 2022,
PCT Pub. No. WO2021/105305, PCT Pub. Date Jun. 3, 2021.
Claims priority of application No. 19211549 (EP), filed on Nov. 26, 2019; and application No. P00201910918 (ID), filed on Nov. 26, 2019.
Prior Publication US 2023/0348815 A1, Nov. 2, 2023
Int. Cl. C11C 3/10 (2006.01); C11C 3/00 (2006.01)
CPC C11C 3/10 (2013.01) [C11C 3/003 (2013.01)] 14 Claims
 
1. A method of transesterifying a fatty acid triglyceride with a C1-30 aliphatic alcohol, the method comprising step (A):
(A) heating the fatty acid triglyceride with the C1-30 aliphatic alcohol in the presence of an acid;
wherein
the acid is selected from the group consisting of a sulfonic acid, a disulfonic acid, a hydroxycarboxylic acid, and a mixture thereof;
the molar ratio of fatty acid triglyceride to aliphatic alcohol is less than 1:6;
the heating in step (A) is in a temperature range of from 20 to less than 100° C.;
the reaction according to step (A) is carried out in presence of water, wherein said water is controlled such to range from 0.01 weight-% to 2.0 weight-% based on the weight of the fatty acid triglyceride (=100 weight-%);
the sulfonic acid is selected from methanesulfonic acid, butanesulfonic acid, octanesulfonic acid, trifluoromethanesulfonic acid, perfluorobutanesulfonic acid, perfluorooctanesulfonic acid, benzenesulfonic acid, toluenesulfonic acid, p-trifluoromethylbenzene sulfonic acid, and a mixture of two or more thereof;
the disulfonic acid is or comprises ethane-1,2-disulfonic acid; and
the hydroxycarboxylic acid is selected from malic acid, citric acid, isocitric acid, glycolic acid, mandelic acid, lactic acid, tartronic acid, tartric acid, mevalonic acid, salicylic acid, p-hydroxybenzoic acid, and a mixture of two or more thereof;
the method further comprising:
terminating the reaction and cooling the reaction mixture to ambient temperature to obtain a phase separation resulting in a lower phase predominantly containing glycerol and the acid, and an upper phase predominantly comprising the formed fatty acid ester and excess C1-30 alcohol.