Optimization of lipase-catalyzed synthesis of cetyl octanoate in supercritical carbon dioxide

JAOCS, Journal of the American Oil Chemists' Society

Volumn 89, Issue 1, 2012, Pages 103-110

  Kuo, Chia Hung ^a   Ju, Hen Yi ^b   Chu, Shuan Wei ^b   Chen, Jiann Hwa ^a   Chang, Chieh Ming J ^a   Liu, Yung Chuan ^a   Shieh, Chwen Jen ^a  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

^b DA YEH UNIVERSITY   (Taiwan)

Author keywords

Cetyl octanoate; Esterification; Lipase catalyzed; Response surface methodology (RSM); Supercritical carbon dioxide (SC CO 2)

Indexed keywords

BASE OIL; BOX-BEHNKEN DESIGN; CETYL ALCOHOL; COSMETIC INDUSTRY; IMMOBILIZED LIPASE; LIPASE-CATALYZED; LIPASE-CATALYZED SYNTHESIS; MOLAR CONVERSION; NOVOZYMES; OCTANOATE; OCTANOIC ACIDS; OPTIMAL CONDITIONS; OPTIMUM CONDITIONS; REACTION CONDITIONS; REACTION PRESSURE; REACTION TEMPERATURE; RESPONSE SURFACE METHODOLOGY; SHORT REACTION TIME; SUPERCRITICAL CARBON DIOXIDES; SYNTHESIS PARAMETERS; WAX ESTERS;

CARBON; CARBON DIOXIDE; CATALYSIS; ESTERIFICATION; ESTERS; FATTY ACIDS; LIPASES; OPTIMIZATION; SURFACE PROPERTIES; SYNTHESIS (CHEMICAL);

SUPERCRITICAL FLUID EXTRACTION;

EID: 84862912855     PISSN: 0003021X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11746-011-1895-8     Document Type: Article

References (27)

1. Patel S, Nelson DR, Gibbs AG (2001) Chemical and physical analyses of wax ester properties. J Insect Sci 1:1-7 (Pubitemid 39080860)
2. Salis A, Solinas V, Monduzzi M (2003) Wax esters synthesis from heavy fraction of sheep milk fat and cetyl alcohol by immobilised lipases. J Mol Catal B Enzym 21:167-174 (Pubitemid 36057134)
3. Petersson AEV, Gustafsson LM, Nordblad M, Börjesson P, Mattiasson B, Adlercreutz P (2005) Wax esters produced by solvent-free energy-efficient enzymatic synthesis and their applicability as wood coatings. Green Chem 7:837-843 (Pubitemid 41802834)
4. Hunter KW Jr, Gault RA, Stehouwer JS, Tam-Chang SW (2003) Synthesis of cetyl myristoleate and evaluation of its therapeutic efficacy in a murine model of collagen-induced arthritis. Pharmacol Res 47:43-47 (Pubitemid 36259621)
5. Gunawan ER, Basri M, Rahman MBA, Salleh AB, Rahman RNZA (2005) Study on response surface methodology (RSM) of lipase-catalyzed synthesis of palm-based wax ester. Enzyme Microb Technol 37:739-744 (Pubitemid 41368048)
6. Kawabata T, Mizugaki T, Ebitani K, Kaneda K (2003) Highly efficient esterification of carboxylic acids with alcohols by montmorillonite-enwrapped titanium as a heterogeneous acid catalyst. Tetrahedron Lett 44:137-140 (Pubitemid 37445162)
7. 2. Tetrahedron Lett 48:6962-6965 (Pubitemid 47331564)
8. Ieda N, Mantri K, Miyata Y, Ozaki A, Komura K, Sugi Y (2008) Esterification of long-chain acids and alcohols catalyzed by ferric chloride hexahydrate. Ind Eng Chem Res 47:8631-8638
9. Isono Y, Nabetani H, Nakajima M (1995) Wax ester synthesis in a membrane reactor with lipase-surfactant complex in hexane. J Am Oil Chem Soc 72:887-890
10. Hadzir NM, Basri M, Rahman MBA, Razak CNA, Rahman RNZA, Salleh AB (2001) Enzymatic alcoholysis of triolein to produce wax ester. J Chem Technol Biotechnol 76:511-515 (Pubitemid 32435557)
11. Dianóczki C, Recseg K, Kovári K, Poppe L (2007) Convenient enzymatic preparation of conjugated linoleic acid alkyl esters with C6-C22 alcohols. J Mol Catal B Enzym 45:45-49 (Pubitemid 46343632)
12. Hobbs HR, Thomas NR (2007) Biocatalysis in supercritical fluids, in fluorous solvents, and under solvent-free conditions. Chem Rev 107:2786-2820 (Pubitemid 47033773)
13. Wimmer Z, Zarevúcka M (2010) A review on the effects of supercritical carbon dioxide on enzyme activity. Int J Mol Sci 11:233-253
14. Knez Z, Laudani CG, Habulin M, Reverchon E (2007) Exploiting the pressure effect on lipase-catalyzed wax ester synthesis in dense carbon dioxide. Biotechnol Bioeng 97:1366-1375 (Pubitemid 47204015)
15. Leitner W (2002) Supercritical carbon dioxide as a green reaction medium for catalysis. Acc Chem Res 35:746-756
16. Laudani CG, Habulin M, Knez Z, Porta GD, Reverchon E (2007) Immobilized lipase-mediated long-chain fatty acid esterification in dense carbon dioxide: bench-scale packed-bed reactor study. J Supercrit Fluid 41:74-81 (Pubitemid 46441775)
17. Habulin M, Šabeder S, Sampedro MA, Knez Z (2008) Enzymatic synthesis of citronellol laurate in organic media and in supercritical carbon dioxide. Biochem Eng J 42:6-12
18. Chen HC, Ju HY, Twu YK, Chen JH, Chang CM, Liu YC, Chang C, Shieh CJ (2010) Optimized enzymatic synthesis of caffeic acid phenethyl ester by RSM. N Biotechnol 27:89-93
19. Ju HY, Huang KC, Chen JH, Liu YC, Chang CMJ, Lee CC, Chang C, Shieh CJ (2010) Optimization of the extraction of Alpinia oxyphylla essence oil in supercritical carbon dioxide. J Am Oil Chem Soc 87:1063-1070
20. AS S (1990) SAS user guide. SAS Institute, Cary
21. Sun S, Shan L, Liu Y, Jin Q, Song Y, Wang X (2009) Solvent-free enzymatic synthesis of feruloylated diacylglycerols and kinetic study. J Mol Catal B Enzym 57:104-108
22. Yadav GD, Dhoot SB (2009) Immobilized lipase-catalysed synthesis of cinnamyl laurate in non-aqueous media. J Mol Catal B Enzym 57:34-39
23. Lystvet SM, Hoff BH, Anthonsen T, Jacobsen EE (2010) Chemoenzymatic synthesis of enantiopure 1-phenyl-2-haloethanols and their esters. Biocatal Biotransform 28:272-278
24. Varma MN, Madras G (2010) Effect of chain length of alcohol on the lipase-catalyzed esterification of propionic acid in supercritical carbon dioxide. Appl Biochem Biotechnol 160:2342-2354
25. Habulin M, Šabeder S, Knez Z (2008) Enzymatic synthesis of sugar fatty acid esters in organic solvent and in supercritical carbon dioxide and their antimicrobial activity. J Supercrit Fluid 45:338-345
26. Olsen T, Kerton F, Marriott R, Grogan G (2006) Biocatalytic esterification of lavandulol in supercritical carbon dioxide using acetic acid as the acyl donor. Enzyme Microb Technol 39:621-625
27. Peterson J (1993) A general approach to ridge analysis with confidence intervals. Technometrics 35:204-214