Synthesis of Trimethylolpropane Esters by Base‐Catalyzed Transesterification

• Published in: European journal of lipid science and technology Vol. 122; no. 3
• Main Authors: Nie, Jieyu, Shen, Jianheng, Shim, Youn Young, Tse, Timothy J., Reaney, Martin J. T.
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 01.03.2020
• Subjects: 1H‐NMR; Biomedical materials; Catalysts; Chemical synthesis; Crude oil; Edible oils; Esters; Fatty acid methyl esters; Fatty acids; Lubricants; NMR; Nuclear magnetic resonance; Oils & fats; Optimization; Potassium; Potassium carbonate; Potassium hydroxide; Potassium hydroxides; Stability; synthesis; Temperature; Transesterification; triacylglycerides; Triglycerides; trimethylolpropane esters; Vacuum; Vegetable oils; Vegetables
• ISSN: 1438-7697; 1438-9312
• DOI: 10.1002/ejlt.201900207

Trimethylolpropane (TMP) esters are synthesized from fatty acid methyl esters (FAMEs) and TMP to produce a fluid with properties suitable for use as a lubricant base oil, exhibiting good stability, and low‐temperature performances. In this study, triacylglyceride (TAG) molecules are modified to produce FAME and then linked to TMP. Initially, vegetable oil is transesterified with excess methanol, and potassium hydroxide to produce crude FAME. The FAMEs are then refined and further transesterified with TMP and heating, under vacuum, using potassium carbonate catalyst. The conversion of TMP is successfully achieved by adding an excess of FAME to a reaction mixture of base and polyol in the second step. All reactions are monitored and confirmed using 1H‐NMR. The reactions proceed quickly as an efficient production of FAME and TMP to TMP triesters is successfully achieved by adding an excess of FAME slowly to a mixture of TMP and catalyst. Practical Applications: The major objective is to develop and optimize a reverse addition reaction method for TMP‐based biolubricant production. The highly enriched TMP biolubricant is prepared by reverse phase chromatography and these biolubricant products are characterized for oxidative stability index and low‐temperature performance. The optimum conditions are applied to different vegetable oils. The aim of this study was to develop and optimize a reverse addition reaction method for trimethylolpropane (TMP)‐based biolubricant production. The highly enriched TMP biolubricant was separated and prepared by reverse phase chromatography and these biolubricant products were characterized to determine both the oxidative stability index and low‐temperature performance. The optimum conditions are applied to different vegetable oils.