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Thiol-functionalization of acrylic ester monomers catalyzed by immobilized Humicola insolens cutinase

Paper ID Volume ID Publish Year Pages File Format Full-Text
17312 42659 2012 7 PDF Available
Title
Thiol-functionalization of acrylic ester monomers catalyzed by immobilized Humicola insolens cutinase
Abstract

Immobilized cutinase HiC from the ascomycete Humicola insolens was applied as a novel biocatalyst for the synthesis of functionalized acryclic esters by transesterification. As a model reaction, transesterification of methyl acrylate with 6-mercapto-1-hexanol at a high molar ratio in a solvent free system was chosen. Besides two minor Michael-addition by-products, 6-mercaptohexyl acrylic ester was identified as the main product with the thiol as the functional end group. Reaction conditions were optimized regarding the influence of water (0–1.72 M), temperature (22–50 °C), product inhibition and addition of the radical inhibitor butylated hydroxytoluol (BHT; 0.14–0.71 M) on conversion and by-product formation. Highest conversion of 6-mercapto-1-hexanol to 6-mercaptohexyl acrylic ester (95.4 ± 0.3%) was achieved after 6 h at 40 °C in the presence of 0.025% (w/w) water without formation of by-products in a solvent free system. Applying methyl methacrylate, transesterification with 6-mercapto-1-hexanol was significantly lower (43.6 ± 0.1%) compared to transesterification of methyl acrylate with 6-mercapto-1-hexanol.

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Keywords
Cutinase; Humicola insolens; Functional monomers; Immobilization; Methyl acrylate; Transesterification
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Thiol-functionalization of acrylic ester monomers catalyzed by immobilized Humicola insolens cutinase
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Publisher
Database: Elsevier - ScienceDirect
Journal: Enzyme and Microbial Technology - Volume 51, Issue 1, 10 June 2012, Pages 9–15
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us