Improved Synthesis of Monopalmitin on a Large Scale by Two Enzymatic Methods
2013
Wang, Xiaosan | Xingguo Wang, | Jin, Qingzhe | Wang, Tong
Monoacylglycerols (MAG) are precursors for the synthesis of symmetrical and unsymmetrical triacylglycerols (TAG). In the present study, we improved two methods for synthesizing MAG. One method involved the enzymatic transesterification of vinyl palmitate with glycerol catalyzed by Novozym 435 lipase, and the other method was an enzymatic esterification of 1,2-acetonide glycerol with palmitic acid catalyzed by Novozym 435 lipase and then the cleavage of 1,2-acetonide-3-palmitoyl glycerol in methanol catalyzed by Amberlyst-15 to produce monopalmitin. Pure monopalmitin was obtained after repeated crystallization. The main novelties of this study are twofold: Novozym 435 proved to be very effective in catalyzing the transesterification between vinyl palmitate and glycerol without absorbing glycerol onto silica gel; and the enzyme catalyzed reaction between 1,2-acetonide glycerol and palmitic acid was simpler and safer than the typical method of using 4-dimethyl aminopyridine and N-ethyl-N′-(3-dimethylaminopropyl)-carbodiimide hydrochloride as catalysts. Our methods for the synthesis of monopalmitin are much simpler and environmentally friendlier than the reported methods, and they are economical and scalable to larger quantity production.
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