Process evaluation of solvent‐free lipase‐catalyzed esterification schemes in the synthesis of structured triglycerides from oleic and palmitic acids

Abstract

Different schemes in the production of structured triglycerides based on solvent‐free esterification of oleic acid and palmitic acid with glycerol were evaluated in terms of reactant conversion, product composition, and yield. Two‐step processes, with or without glycerol dosing, were compared with one‐step versions carried out at temperature conditions within 40°C–60°C to a final oleic acid/palmitic acid/glycerol ratio of 2:1:1, the stoichiometric ratio in 1,3‐dioleoyl‐2‐palmitoyl glycerol (OPO). Substantial amounts of C52 triglycerides, including OPO, were produced in all schemes at 34.98–39.55 wt.% of the total triglycerides and triglyceride yields of 50.10–56.56 wt.% based on the raw materials. The two‐step process with glycerol dosing at 60°C showed the highest palmitic acid incorporation at the sn‐2 position of 46.46%, but the same process carried out with a step increase in temperature from 40°C to 60°C gave the highest OPO yield at 19.30 wt.%. These results demonstrate the possibility of manipulating regioselectivity and triglyceride specificity by varying reactant feeding schemes without the use of solvents and sn‐1,3‐specific lipases common in conventional acidolysis‐based processes.

Progress and perspectives of enzymatic preparation of human milk fat substitutes

“…3c. Agapay et al [47] explored the esterification-esterification process for OPO production using Novozym 435 as the biocatalyst. Although the regioselectivity can be manipulated by varying reactant feeding scheme, the use of nonspecific lipase resulted in relatively low OPO yield.…”

Preparation of Human Milk Fat Substitutes: A Review

“…This can be attributed t large steric hindrance of LC-PUFAs and the higher catalytic activity of lipase for o fatty acids. [135] used two-step esterifica for the preparation of OPO, with oleic acid, palmitic acid and glycerol as reaction strates. The OPO content in the prepared product was 34.98-39.55 wt%, which mat that of acidolysis products in several studies.…”

“…Two-step esterification has been used to synthesize DAGs and TAGs step by step, which includes adding FFAs in batches. Agapay et al [135] used two-step esterification for the preparation of OPO, with oleic acid, palmitic acid and glycerol as reaction substrates. The OPO content in the prepared product was 34.98-39.55 wt%, which matched that of acidolysis products in several studies.…”