无搅拌条件下的Pickering乳液用于脂肪酶催化合成酯的反应

doi:10.13218/j.cnki.csdc.2018.04.006

Abstract

Abstract: To solve the problems currently in enzymatic reactions (such as low efficiency and the destruction of enzyme structure induced by stirring),a novel strategy of stirring-free two-phase enzymatic reaction was developed.In this strategy,the conventional two-phase enzymatic reaction was altered by a system of water-in-oil (W/O) Pickering emulsion in which a small amount of interfacial-active solid particles were used as emulsifier.In this system,a Burkholderia Cepacia lipase (BCL) enzyme was packaged within micron-sized water droplets,while organic substrates were dissolved in oil phase (outside the droplets).The experimental results show that,the reaction efficiency of BCL-catalyzed transesterification is obviously higher in the stirring-free Pickering emulsion than in the conventional two-phase system under stirring.The reasons may be that the droplets of Pickering emulsion have a large area of reaction interface and a short distance for molecular diffusion.In addition,it is found that the specific activity of enzyme depends on the size of water droplets,indicative of the importance of droplets in the reaction system.Moreover,effective recycling of BCL enzyme can be simply realized through demulsification by centrifugation.After 6 reaction cycles,the conversion is still as high as 86%,probably due to the avoidance of stirring that may cause damage to the three-dimensional structure of enzyme.This study demonstrates that the Pickering emulsion is an innovative platform for efficient enzyme-catalyzed transesterification without stirring or immobilization.

Key words: Pickering emulsion, two-phase catalysis, enzymatic reaction, transesterification, additives of skin-care cosmetics

CLC Number:

O648.2+3

BAI Pei-ling, YOU Xue-rui, HAO Ya-juan, ZHANG Xiao-ming, YANG Heng-quan. Enzymatic synthesis of esters in stirring-free Pickering emulsions[J].China Surfactant Detergent & Cosmetics, 2018, 48(4): 210-215.

References

[1] Jiménez L,Garvín A,Costa-López J.The production of butyl acetate and methanol via reactive and extractive distillation.I.chemical equilibrium,kinetics,and mass-transfer issues [J].Industrial & Engineering Chemistry Research,2002,41(26):6663-6669.
[2] Bozek-Winkler E,Gmehling J.Transesterification of methyl acetate and n-butanol catalyzed by amberlyst 15 [J].Industrial & Engineering Chemistry Research,2006,45(20):6648-6654.
[3] Jiang Y J,Shi L L,Huang Y,et al.Preparation of robust biocatalyst based on cross-linked enzyme aggregates entrapped in three-dimensionally ordered macroporous silica [J].ACS Applied Materials & Interfaces,2014,6(4):2622-2628.
[4] Dong F Y,Li L M,Lin L,et al.Transesterification synthesis of chloramphenicol esters with the lipase from bacillus amyloliquefaciens [J].Molecules,2017,22(9):1523-1533.
[5] Chen W,Chen X Y,Dai Y,et al.Sythesis of myristic acid sugar ester catalyzed by Candida antarctica lipase B displaying Pichia pastoris [J].China Surfactant Detergent & Cosmetics,2016,46(12):690-696.
[6] Lin F.Study on the synthesis of esters from aldehydes or carboxylic acids with dichloroalkane under mild conditions [D].Quanzhou:Huaqiao University,2014.
[7] Peng Y L,Guo C H,Chen Y X,et al.Inquiry on the synthesis method of ester compounds [J].Shandong Chemical Industry,2015,44(15):89-91.
[8] Ge J J.Synthesis and processing research of esterification by functionalized acid ionic liquids [D].Shijiazhuang:Hebei University of Science and Technology,2014.
[9] Heils R,Niesbach A,Wierschem M,et al.Integration of enzymatic catalysts in a continuous reactive distillation column:reaction kinetics and process simulation [J].Industrial & Engineering Chemistry Research,2014,53:19612-19619.
[10] Tang J Q,Zhu L F,Fu X,et al.Insights into the kinetics and reaction network of aluminum chloride-catalyzed conversion of glucose in NaCl-H₂O/THF biphasic system [J].ACS Catalysis,2017,7(1):256-266.
[11] Cantarella M,Mucciante C,Cantarella L.Inactivating effects of lignin-derived compounds released during lignocellulosic biomass pretreatment on the endo-glucanase catalyzed hydrolysis of carboxymethylcellulose:A study in continuous stirred ultrafiltrationmembrane reactor [J].Bioresource Technology,2014,156:48-56.
[12] Chen B,Bukhryakov K,Sougrat R,et al.Enzyme-inspired functional surfactant for aerobic oxidation of activated alcohols to aldehydes in water [J].ACS Catalysis,2015,5(2):1313-1317.
[13] Dwars T,Paetzold E,Oehme G.Reactions in micellar systems [J].Angewandte Chemie,2005,44:7174-7199.
[14] Liu J,Lan G J,Peng J,et al.Enzyme confined in silica-based nanocages for biocatalysis in a Pickering emulsion [J].Chemical Communications,2013,49:9558-9560.
[15] Egi M,Sugiyama K,Saneto M,et al.A mesoporous-silica-immobilized oxovanadium cocatalyst for the lipase-catalyzed dynamic kinetic resolution of racemic alcohols [J].Angewandte Chemie,2013,52(13):3654-3658.
[16] Zhao M J,Bai R X,Liu Q,et al.Study on preparation of Pickering emulsion on stabilized by N-TiO₂ nanoparticles and triggering enzymatic reaction [J].China Surfactant Detergent & Cosmetics,2017,47(3):137-141.
[17] Xie C Y,Meng S X,Xue L H,et al.Light and magnetic dual-responsive Pickering emulsion micro-reactors [J].Langmuir,2017,33(49):14139-14148.
[18] Zhang W J,Fu L M,Yang H Q.Micrometer-scale mixing with Pickering emulsions:biphasic reactions without stirring [J].ChemSusChem,2014,7(2):391-396.
[19] Zhang M,Wei L J,Chen H,et al.Compartmentalized droplets for continuous flow liquid-liquid interface catalysis [J].Journal of the American Chemical Society,2016,138(32):10173-10178.
[20] Zhang M,Ettelaie R,Yan T,et al.Ionic liquid droplet micro-reactor for catalysis reactions not at equilibrium [J].Journal of the American Chemical Society,2017,139(48):17387-17396.
[21] Li M,Harbron R,Weaver J,et al.Electrostatically gated membrane permeability in inorganic protocells [J].Nature Chemistry,2013(5):529-536.
[22] Gautier F,Destribats M,Perrier-Cornet R,et al.Pickering emulsions with stimulable particles:from highly-to weakly-covered interfaces [J].Physical Chemistry Chemical Physics,2007,9(48):6455-6462.
[23] Yang H Q,Fu L M,Wei L J,et al.Compartmentalization of incompatible reagents within Pickering emulsion droplets for one-pot cascade reactions [J].Journal of the American Chemical Society,2015,137:1362-1371.

Enzymatic synthesis of esters in stirring-free Pickering emulsions

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