Synthesis of trimethylolpropane esters of oleic acid by Lipoprime 50T

Abstract

The ability of the commercial lipolytic enzyme Lipoprime 50T to catalyze the biotechnologically important synthesis of the biodegradable and environmentally acceptable trimethylolpropane (2-ethyl-2-(hydroxymethyl)-1,3-propanediol) ester of oleic acid was investigated. Simple and accurate thin-layer chromatography and computer analysis methods were used that enable one to follow changes of all reaction mixture components simultaneously. The processes of transesterification and esterification were compared. The effects of the molar ratio of the substrates, reaction temperature, time, and medium on the composition of the reaction mixture were analyzed. Esterification was determined to be more preferable than transesterification in both studied solvents. Under the optimal conditions identified (15% w/w water, temperature 60°C, trimethylolpropane to oleic acid molar ratio 1:3.5, and reaction time 72 h), the highest trimethylolpropane trioleate yield of around 62% and trimethylolpropane mono-, di-, and trioleate overall yield of about 83% were obtained. Although the yields are not high enough for industrial application, the process shows the potential to be optimized for higher yields in the near future as the conversions were obtained at ambient pressure, whereas many other processes described in the literature are conducted under vacuum at a specific pressure.

Adsorption Behavior of Trimethylolpropane‐Dehydroabietic Acid Ester at the Air–water Interface

“…From Eqs. (6) and (8), v 0 s and the sum of v 1 s and v 2 s can be obtained. It can be seen from Fig.…”

“…In addition to the above-mentioned TMP esters, other esters such as a soybean oil-TMP ester [4], a Jatropha curcas oil-TMP ester and an oleic acid-TMP ester [5] have also been produced. The esterification processes were accomplished through transesterification reactions catalyzed by various enzymes [2,6] or strong inorganic acids, aromatic acids, metal oxides, etc. [7].…”

Switchable Substrates for Analyzing and Engineering Cellular Functions

“…Renewable resources have also been used to formulate synthetic esters, which feature unique qualities 60, 61 that make them distinctly better than their petroleum‐based counterparts 61, 131, 132. A majority of these synthetic esters originate from branched polyols such as TMP, NPG, and PE.…”

High Performance Protein-Coated Microcrystals of Rhizomucor miehei Lipase: Preparation and Application for Organic Synthesis

“…Lipase-based reactions are used for oil and fat processing, food industry, biodiesel and biolubricant production, synthesis of flavor esters and enantiopure pharmaceuticals, or as an ingredient for various detergents [5][6][7][8]. Therefore, numerous lipase preparations for industrial application are commercially available from several companies.…”