Enzymatic acrylation of 2-hydroxy-γ-butyrolactone to synthesize the gamma butyrolactone methacrylate (GBLMA) for photoresist

Biotechnology and Bioprocess Engineering

Volumn 15, Issue 2, 2010, Pages 208-212

  Kim, Sang Cheol ^b   Nam, Dong Hyun ^a   Kim, Yong Hwan ^a   Song, Bong Keun ^b  

^a Kwangwoon University   (South Korea)

^b Korea Research Institute of Chemical Technology   (South Korea)

Author keywords

2 Hydroxy butyrolactone; Acrylates; Candida antarctica lipase B; Novozym 435

Indexed keywords

ACRYLATIONS; ACYL DONORS; BUTYROLACTONES; CANDIDA ANTARCTICA LIPASE B; CHEMICAL PROCESS; CONVERSION RATES; IMMOBILIZED LIPASE B FROM CANDIDA ANTARCTICA; LOG P-VALUE; METHYL TERT BUTYL ETHER; NOVOZYM435; OPTIMIZED CONDITIONS; REACTION TEMPERATURE;

ETHERS; ISOMERS; RESINS; SALTS; SOLVENTS; YEAST;

SYNTHESIS (CHEMICAL);

2 HYDROXY GAMMA BUTYROLACTONE; ACRYLIC ACID; BUTYROLACTONE; ETHER DERIVATIVE; GAMMA BUTYROLACTONE METHACRYLATE; LIPASE B; TERT BUTYL ETHER; UNCLASSIFIED DRUG; VINYL METHACRYLATE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ENZYME IMMOBILIZATION; SOLVATION; SYNTHESIS; TEMPERATURE SENSITIVITY;

CANDIDA ANTARCTICA;

EID: 77953608098     PISSN: 12268372     EISSN: None     Source Type: Journal    
DOI: 10.1007/s12257-009-0190-0     Document Type: Article

References (16)

1. Ohrui, T., Y. Sakakibara, Y. Aono, M. Kato, H. Takao, and T. Kawaguchi (1975) Process for continuously synthesizing acrylic acid esters. US patent 3875212.
2. Kumar, R., R. Tyagi, V. S. Parmar, L. A. Samuelson, J. Kumar, and A. C. Watterson (2003) Enzymatic synthesis of multicomponent copolymers and their structural characterization. Mol. Diversity. 6: 287-295.
3. Gotor-Fernández, V., R. Brieva, and V. Gotor (2006) Lipases: useful biocatalysts for the preparation of pharmaceuticals. J. Mol. Catal. B: Enzym. 40: 111-120.
4. Torres, C. and C. Otero (2001) Part III. Direct enzymatic esterification of lactic acid with fatty acids. Enzym. Microb. Technol. 29: 3-12.
5. Berger, M., K. Laumen, and M. P. Schneider (1992) Enzymatic esterification of glycerol I. lipase-catalyzed synthesis of regioisomerically pure 1,3-sn-diacylglycerols. J. Am. Oil Chem. Soc. 69: 955-960.
6. Hajjar, A. B., P. F. Nicks, and C. J. Knowles (1990) Preparation of monomeric acrylic ester intermediates using lipase catalyzed transesterifications in organic solvents. Biotehcnol. Lett. 12: 825-830.
7. Warwel, S., G. Steinke, and M. R. Klass (1996) An efficient method for lipase-catalyzed preparation of acrylic and methacrylic acid esters. Biotechnol. Tech. 10: 283-286.
8. Park, D. W., S. Haam, I. S. Ahn, T. G. Lee, H. S. Kim, and W. S. Kim (2004) Enzymatic esterification of beta-methylglucoside with acrylic/methacrylic acid in organic solvent. J. Biotechnol. 107: 151-160.
9. Nordblad, M. and P. Adlercreutz (2007) Efficient enzymatic acrylation through transesterification at controlled water activity. Biotechnol. Bioeng. 55: 798-806.
10. Nordblad, M. and P. Adlercreutz (2008) Effects of acid concentration and solvent choice on enzymatic acrylation by Candida antarctica lipase B. J. Biotechnol. 133: 127-133.
11. Kim, J. B., J. S. Ko, J. H. Choi, J. H. Jang, T. H. Oh, H. W. Kim, and B. W. Lee (2004) Synthesis and lithographic evaluation of poly((methacrylic acid tert-butyl cholate ester)-co-(γ-butyrolactone-2-yl methacrylate)). Polymer 45: 5397-5401.
12. Wang, M., N. D. Jarnagin, C. T. Lee, C. L. Henderson, W. Yueh, J. M. Roberts, and K. E. Gonsalves (2006) Novel polymeric anionic photoacid generators (PAGs) and corresponding polymers for 193 nm lithography. J. Mater. Chem. 16: 3701-3707. (Pubitemid 44414710)
13. Kim, H. W., S. Y. Lee, K. Y. Kwon, D. W. Jung, S. J. Choi, and S. G. Woo (2003) Alicyclic photosensitive polymer, resist composition containing the same and method of preparing the resist composition. US Patent 6503687.
14. Nakamura, K., M. Kinoshita, and A. Ohno (1994) Effect of solvent on lipase-catalyzed transesterification in organic media. Tetrahedron 50: 4681-4690.
15. Akoh, C. C. and L. N. Yee (1998) Lipase-catalyzed transesterification of primary terpene alcohols with vinyl esters in organic media. J. Mol. Catal. B: Enzym. 4: 149-153.
16. Kim, S. C., Y. H. Kim, H. Lee, D. Y. Yoon, and B. K. Song (2007) Lipase-catalyzed synthesis of glycerol carbonate from renewable glycerol and dimethyl carbonate through transesterification. J. Mol. Catal. B: Enzym. 49: 75-78.