Novel biocatalytic tandem reaction for estolides synthesis from natural oils.

Boeriu, C. (Speaker), Anamaria Todea (Contributor), Linda Otten (Contributor), Isabel Arends (Contributor), Francisc Peter (Contributor)

Activity: Talk or presentationOral presentationAcademic


Oral presentation, abstract and conference paper
Estolides are branched polyesters derived from oils and fats, and represent an evolving class of natural and synthetic compounds with numerous industrial applications. Except ricinoleic estolides, that are obtained by lipase-catalyzed esterification, all other estolides are commercially produced in energy intensive chemocatalytic processes, that usually take place at T > 200 oC. Recently, we showed that enzymatic synthesis is a viable alternative for the synthesis of estolides [1] and hydroxyfatty acids [2]. Here we report a novel enzymatic tandem procedure for the synthesis of oleic acid estolides starting from triolein. The process consists of a simple one-pot enzymatic cascade using two enzymes to catalyse three consecutive reactions - a single lipase to catalyse both the hydrolysis of the triglyceride substrate (1st reaction) and the ester synthesis (3rd reaction) coupled with the oleate hydratase from Elizabethkingia meningoseptica (OHase) to catalyse the in situ synthesis of 10-hydroxystearic acid, 10-HAS, (2nd reaction). We showed that 1,3-nonspecific lipases can catalyse the formation of estolides of 10-HSA under aqueous conditions suitable for OHase activity, i.e. buffered solution at pH 6-8.5 and at low temperatures, e.g. 30 oC. Various lipases were tested and the reaction conditions were tuned regarding the enzymes ratio, pH and temperature. The progress of the reaction and the reaction intermediates and products were confirmed and characterized by GC-MS and MALDI-TOF-MS. Under optimal conditions, total conversion of triolein into mono- and di-estolides of oleic acid was obtained [3]. This work opens up for the first time the possibility of a simple low energy one-pot enzymatic process to produce fatty acid estolides from natural plant oils, for many industrial applications including use as biodegradable lubricants and coatings and for use in the food and cosmetic industries.
Period16 May 201719 May 2017
Event titleInternational Symposium on Green Chemistry 2017
Event typeConference
LocationLa Rochelle, France
Degree of RecognitionInternational