Synthesis of Trimethylolpropane Esters by Base‐Catalyzed Transesterification

Abstract

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.

Microwave-assisted synthesis of trimethylolpropane triester (bio-lubricant) from camelina oil

“…The reaction yield of the reaction was calculated using Mestrenova 11.0.4 software and Eq. ( 1 ) 29 : which, A is the area under the peak with a chemical displacement of 4.02 ppm and B is the area under the peak with a chemical displacement of 4 ppm. The Box Behnken design used in this study and yield obtained by H-NMR are tabulated in Table 3 .…”

“…In another study, optimal conditions of the process for maximum yield (96.4%), were K 2 CO 3 catalyst concentration of 1 wt%, the reaction time of 2 h, methyl ester to TMP molar ratio of 3.9, the temperature of 130 °C and vacuum pressure of 3.87 kPa 29 .…”

Impact of Vegetable Oil Type on the Rheological and Tribological Behavior of Montmorillonite-Based Oleogels

“…The biodegradability of vegetable oils (90–98%) is much higher than that of mineral oil-based lubricants (20–40%) [ 21 ]. However, vegetable oils also have drawbacks such as poor thermal oxidative stability, with a tendency for hydrolysis, oxidation, and thermal decomposition [ 22 ] as well as a high melting point that restricts their use in some critical applications [ 23 , 24 ]. Since the double bonds in the fatty acid chains in vegetable oils quickly react with oxygen, and a high content of double bonds is found in vegetable oils, such as sunflower, soybean, olive, linseed, and palm.…”

Photo-on-Demand Base-Catalyzed Phosgenation Reactions with Chloroform: Synthesis of Arylcarbonate and Halocarbonate Esters

“…Although it is known that an alcohol serves as a stabilizer to inhibit decomposition of CHCl 3 , in situ reaction of the alcohol and COCl 2 generated through oxidative photodecomposition of CHCl 3 allowed formation of the chloroformate in high yield. By taking advantage of using CHCl 3 , which bifunctionally serves as a reactant and a solvent, the photochemical synthesis of chloroformate was further extended to the one-pot synthesis of carbonate esters upon subsequent addition of an alcohol with or without an organic base, which works as a catalyst as well as HCl scavenger . Since organic bases such as triethylamine and pyridine absorb UV light, further difficulties were expected in the direct photochemical synthesis of the carbonate with a CHCl 3 solution containing the mixture of alcohol and organic base, both of which inhibit the photodecomposition of CHCl 3 .…”