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. 2013 May 8:12:65.
doi: 10.1186/1476-511X-12-65.

Solvent-free enzymatic synthesis of 1, 3-diacylglycerols by direct esterification of glycerol with saturated fatty acids

Nanjing Zhong, Zhongyu Gui, Li Xu, Jianrong Huang, Kun Hu, Yongqing Gao, Xia Zhang, Zhenbo Xu, Jianyu Su, Bing Li

Solvent-free enzymatic synthesis of 1, 3-diacylglycerols by direct esterification of glycerol with saturated fatty acids

Nanjing Zhong et al. Lipids Health Dis. .

Abstract

Background: Pure 1, 3-diacylglycerols (1, 3-DAG) have been considered to be significant surfactants in food, cosmetics and pharmaceutical industries, as well as the effect on obesity prevention.

Methods: In this study, a vacuum-driven air bubbling operation mode was developed and evaluated for the enzymatic synthesis of 1, 3-DAG of saturated fatty acids, by direct esterification of glycerol with fatty acids in a solvent-free system. The employed vacuum-driven air bubbling operation mode was comparable to vacuum-driven N2 bubbling protocol, in terms of lauric acid conversion and 1, 3-dilaurin content.

Results: Some operation parameters were optimized, and 95.3% of lauric acid conversion and 80.3% of 1, 3-dilaurin content was obtained after 3-h reaction at 50°C, with 5 wt% of Lipozyme RM IM (based on reactants) amount. Of the lipases studied, both Lipozyme RM IM and Novozym 435 exhibited good performance in terms of lauric acid conversion. Lipozyme TL IM, however, showed low activity. Lipozyme RM IM showed good operational stability in this operation protocol, 80.2% of the original catalytic activity remained after 10 consecutive batch applications. Some other 1, 3-DAG were prepared and high content was obtained after purification: 98.5% for 1, 3-dicaprylin, 99.2% for 1, 3-dicaprin, 99.1% for 1, 3-dilaurin, 99.5 for 1, 3-dipalmitin and 99.4% for 1, 3-disterin.

Conclusion: The established vacuum-driven air bubbling operation protocol had been demonstrated to be a simple-operating, cost-effective, application practical and efficient methodology for 1, 3-DAG preparation.

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Figures

Figure 1
Figure 1
Reaction setup. Schematic diagram of vacuum-driven air bubbling reaction system.
Figure 2
Figure 2
Time courses of lauric acid conversion and 1, 3–dilaurin content under air-bubbling and N2-bubbling reaction systems. The reaction was performed with 20 mmol lauric acid, 10 mmol glycerol, and 0.25 g Lipozyme RM IM at 50°C. Vacuum applied was at 4 mm Hg for both the systems and N2 was at 0.7 L/min for N2-bubbling reaction system.
Figure 3
Figure 3
Effect of lipase on conversion of lauric acid. Reaction conditions: lauric acid 20 mmol, glycerol 10 mmol, lipase amount 0.25 g, vacuum applied 4 mm Hg, reaction temperature 50°C.
Figure 4
Figure 4
Effect of lipase concentration on conversion of lauric acid and content of 1, 3-dilaurin. Reaction conditions: lauric acid 20 mmol, glycerol 10 mmol, vacuum applied 4 mm Hg, reaction temperature 50°C and time 3 h.
Figure 5
Figure 5
Reusability of Lipozyme RM IM. Reaction conditions: lauric acid 20 mmol, glycerol 10 mmol, lipase amount 0.25 g, vacuum applied 4 mm Hg, reaction temperature 50°C and time 3 h.
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