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Lipase-catalyzed esterification of ferulic Acid with oleyl alcohol in ionic liquid/isooctane binary systems.

Journal of agricultural and food chemistry (2011-01-22)
Bilian Chen, Huanzhen Liu, Zheng Guo, Jian Huang, Minzi Wang, Xuebing Xu, Lifei Zheng
ABSTRACT

Lipase-catalyzed synthesis of ferulic acid oleyl alcohol ester in an ionic liquid (IL)/isooctane system was investigated. Considerable bioconversion and volumetric productivity were achieved in inexpensive 1-hexyl-3-methylimidazolium hexafluorophosphate ([Hmim][PF(6)]) and 1-methyl-3-octylimidazolium hexafluorophosphate ([Omim][PF(6)]) mediated systems, and thus, the two types of ILs were selected for further optimization of variables. The results showed that, before reaching a maximum, the increase of ferulic acid concentration, temperature, or enzyme dosage led to an increase in volumetric productivity. Variations of the ratios of IL/isooctane and concentrations of oleyl alcohol also profoundly affected the volumetric productivity. To a higher extent, [Hmim][PF(6)]/isooctane and [Omim][PF(6)]/isooctane show similar reaction behaviors. Under the optimized reaction conditions (60 °C, 150 mg of Novozym 435 and 100 mg of molecular sieves), up to 48.50 mg/mL productivity of oleyl feruleate could be achieved for the [Hmim][PF(6)]/isooctane (0.5 mL/1.5 mL) system with a substrate concentration of ferulic acid of 0.08 mmol/mL and oleyl alcohol of 0.32 mmol; while an optimum volumetric productivity of 26.92 mg/mL was obtained for the [Omim][PF(6)]/ isooctane (0.5 mL/1.5 mL) system under a similar reaction condition other than the substrate concentrations of ferulic acid at 0.05 mmol/mL and oleyl alcohol at 0.20 mmol.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
2,2,4-三甲基戊烷, anhydrous, 99.8%
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2,2,4-三甲基戊烷, ACS reagent, ≥99.0%
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2,2,4-三甲基戊烷, HPLC Plus, for HPLC, GC, and residue analysis, ≥99.5%
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2,2,4-三甲基戊烷, suitable for HPLC, ≥99%
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2,2,4-三甲基戊烷, puriss. p.a., ≥99.5% (GC)
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油醇, ≥99% (GC)
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油醇, technical grade, 85%
Supelco
2,2,4-三甲基戊烷, analytical standard
Sigma-Aldrich
2,2,4-三甲基戊烷, ReagentPlus®, ≥99%
Sigma-Aldrich
2,2,4-三甲基戊烷, puriss. p.a., ACS reagent, ≥99.5% (GC)
Supelco
密度标准品 692kg/m3, H&D Fitzgerald Ltd. Quality