Lipase catalyzed synthesis of ester-based surfactants from biomass derivatives

Biofuels, Bioproducts and Biorefining

Volumn 2, Issue 2, 2008, Pages 144-154

  Karmee, Sanjib Kumar ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Esterification; Monoglycerides; Sugar fatty esters; Transesterification; Vitamin C fatty esters

Indexed keywords

COSMETIC INDUSTRY; L-ASCORBIC ACID; LIPASE-CATALYZED SYNTHESIS; LOW COSTS; MEDIUM-CHAIN FATTY ACIDS; MIXTURE OF SOLVENTS; MONOGLYCERIDES; POLAR SUBSTRATES; REGIOSELECTIVE REACTIONS; T-BUTANOL; VITAMIN-C FATTY ESTERS;

ACETONE; AROMATIC HYDROCARBONS; BIOMASS; ESTERIFICATION; FATTY ACIDS; GLYCEROL; IONIC LIQUIDS; IONIZATION OF LIQUIDS; LIPASES; OILS AND FATS; ORGANIC ACIDS; ORGANIC SOLVENTS; SUGAR (SUCROSE); SUGARS; SURFACE ACTIVE AGENTS;

ESTERS;

EID: 46849110667     PISSN: 1932104X     EISSN: None     Source Type: Journal    
DOI: 10.1002/bbb.60     Document Type: Review

References (84)

1. Patel M, Surfactants based on renewable raw materials; carbon dioxide reduction potential and policies and measures for the European Union. J Ind Ecol 7:47-62 (2004).
2. Johansson I and Svensson M, Surfactants based on fatty acids and other natural hydrophobes. Curr Opin Coll Int Sci 6:178-188 (2001).
3. Biermann U, Friedt W, Lang S, Lühs W, Machmüller G, Metzger JO et al. New syntheses with oils and fats as renewable raw materials for the chemical industry. Angew Chem Int Ed 39:2206-2224 (2000).
4. Hill K, Fats and oils as oleochemical raw materials. Pure Appl Chem 72:1255-1264 (2000).
5. Bornscheuer UT, Enzymes in lipid modification, Wiley-VCH, Weinheim (2000).
6. Rahman MBA, Basri M, Hussein, MZ, Idris MNH, Rahman RNZRA and Salleh AB, Immobilisation of lipase from Candida rugosa on layered double hydroxides of Mg/Al and its nanocomposite as biocatalyst for the synthesis of ester. Catal Today 93-95(1):405-410 (2004).
7. Bornscheuer UT, Lipase catalyzed synthesis of monoacyglycerols. Enz Microb Technol 17:578-586 (1995).
8. Berger M and Schneider MP, Enzymic esterification of glycerol II. Lipase catalyzed synthesis of regioisomerically pure 1(3)-rac-monoacylglycerols. J Am Oil Chem Soc 69(10):961-965 (1992).
9. Berger M and Schneider MP. Regioisomerically pure mono and diacylglycerols as synthetic building blocks. Fat Sci Technol 95:169-175 (1993).
10. Waldinger C and Schneider MP, Enzymic esterification of glycerol III. Lipase-catalyzed synthesis of regioisomerically pure 1,3-sn-diacylglycerols and 1(3)-rac-monoacylglycerols derived from unsaturated fatty acids. J Am Oil Chem Soc 73:1513-1519 (1996).
11. Berger M and Schneider MP, Regioselectivity of lipases in organic solvents. Biotechnol Lett 13:333-338 (1991).
12. Yamane T, Hoq M M, Shimizu S, Ishida S and Funada T, Continuous synthesis of glycerides by lipase in a microporous membrane bioreactor. Ann N Y Acad Sci 434:558-568 (1984).
13. Hoq MM, Tagami H, Yamane T and Shimizu S, Bioreactor for enzymic reaction of fat and fatty acid derivatives. Part II. Some characteristics of continuous glyceride synthesis by lipase in a microporous hydrophobic membrane bioreactor. Agric Biol Chem 49:335-342 (1985).
14. Yamaguchi S and Mase T, High-yield synthesis of monoglyceride by mono-and diacylglycerol lipase from Penicillium camembertii U-150. J Ferment Bioeng 72:162-167 (1991).
15. Gancet C, Catalysis by Rhizopus arrhizus mycelial lipase. Ann N Y Acad Sci 613:600-604 (1990)
16. Otero C, Pastor E, Rua ML and Ballesteros A, Hydrolysis and synthesis of butyryl glycerols by lipases. Ann N Y Acad Sci 613:523-528 (1990).
17. Hayes DG and Gulari E, Formation of polyol-fatty acid esters by lipases in reverse micellar media. Biotechnol Bioeng 40:110-118 (1992).
18. Singh CP, Shah DO and Holmberg K, Synthesis of mono-and diglycerides in water-in-oil microemulsions. J Am Oil Chem Soc 71:538-587(1994).
19. Omar IC, Nishio N and Nagai S, Fat hydrolysis and esterification by a lipase from Humicola lanuginosa. Agric Biol Chem 51:2153-2159 (1987).
20. Hee-Guk B, Tae-Kil E, Won-Kyo J and Se-Kwon K, Lipase catalyzed production of monoacylglycerols by the esterification of fish oil fatty acids with glycerol. Biotechnol Biopro Eng 12(5):491-496 (2007).
21. Tripathi V, Trivedi R and Singh RP, Lipase-catalyzed synthesis of diacylglycerol and monoacylglycerol from unsaturated fatty acid in organic solvent system. J Oleo Sci 55(2):65-69 (2006).
22. Watanabe Y, Nagao T, Kanatani S, Kobayashi T, Terai T and Shimada Y, Purification of monoacylglycerol with conjugated linoleic acid synthesized through a lipase-catalyzed reaction by solvent winterization. J Oleo Sci 55(10):537-543 (2006).
23. Linde DM, Soren K, Degn JA, Vang SF and Xuebing X, Process development of continuous glycerolysis in an immobilized enzymepacked reactor for industrial monoacylglycerol production. J Agric Food Chem 55(19):7786-7792 (2007).
24. Chong FC, Tey BT, Dom ZM, Cheong KH, Satiawihardja B, Ibrahim MN et al., Rice bran lipase catalyzed esterification of palm oil fatty acid distillate and glycerol in organic solvent. Biotechnol Biopro Eng 12 (3):250-256 (2007).
25. Pawongrat AK, Xu RX and Aran H.-K, Synthesis of monoacylglycerol rich in polyunsaturated fatty acids from tuna oil with immobilized lipase. Food Chem 104(1):251-258 (2007).
26. Tripathi V and Singh RP, Production of mono-and diacylglycerols by lipase-catalyzed hydrolysis of rice bran oil. J Lipid Sci Technol 38(3): 122-123 (2006).
27. Yang Ti, Rebsdorf M, Engelrud U and Xu X, Monoacylglycerol synthesis via enzymatic glycerolysis using a simple and efficient reaction system. J Food Lipids 12(4):299-312 (2005).
28. Guo Z and Xu X, Lipase-catalyzed glycerolysis of fats and oils in ionic liquids:a further study on the reaction system. Green Chem 8(1):54-62 (2006).
29. Nandi S, Gangopadhyay S and Ghosh S, Production of medium chain glycerides and monolaurin from coconut acid oil by lipase-catalyzed reactions. J Oleo Sci 53(10):497-501 (2004).
30. Kaewthong W and H-Kittikun A, Glycerolysis of palm olein by immobilized lipase PS in organic solvents. Enz Microb Technol 35 (2-3):218-222 (2004).
31. Wongsakul S, Prasertsan P, Bornscheuer UT and H-Kittikun A, Synthesis of 2-monoglycerides by alcoholysis of palm oil and tuna oil using immobilized lipases. Eur J Lipid Sci Technol 105(2):68-73 (2003).
32. Ferreira-Dias S, Correia AC, Baptista FO and Fonseca da MMR, Contribution of response surface design to the development of glycerolysis systems catalyzed by commercial immobilized lipases. J Mol Catal B:Enzymatic 11(4-6):699-711(2001).
33. Rezaei K and Temelli F, Lipase-catalyzed hydrolysis of canola oil in supercritical carbon dioxide. J Am Oil Chem Soc 77(8):903-909 (2000).
34. Tuter M and Aksoy HA, Solvent-free glycerolysis of palm and palm kernel oils catalyzed by commercial 1,3-specific lipase from Humicola lanuginosa and composition of glycerolysis products. Biotechnol Lett 22 (1):31-34 (2000).
35. Elfman-Borjesson I and Harrod M, Synthesis of monoglycerides by glycerolysis of rapeseed oil using immobilized lipase. J Am Oil Chem Soc 76 (6):701-707 (1999).
36. Tuter M, Babali B, Kose O, Dural S and Aksoy HA, Solvent-free glycerolysis of palm and palm kernel oils catalyzed by a 1,3-specific lipase and fatty acid composition of glycerolysis products. Biotechnol Lett 21(3):245-248 (1999).
37. Fan H-L, Chu Y, Yang G-X, Zhang W, Liu J-L, Wu Z-S et al., Lipase-catalyzed syntheses of monoglycerides by hydrolysis of soybean oil in AOT/isooctane reversed micelles. Ann N Y Acad Sc 864 (Enzyme Engineering XIV), 267-272 (1998).
38. Thude S, Shukun L, Said MB and Bornscheuer UT, Lipase-catalyzed synthesis of monoacylglycerides by glycerolysis of camphor tree seed oil and cocoa-butter. Fett/Lipid 99 (7):246-250 (1997).
39. Rosu R, Uozaki Y, Iwasaki Y and Yamane T, Repeated use of immobilized lipase for monoacylglycerol production by solid-phase glycerolysis of olive oil. J Am Oil Chem Soc 74(4):445-450 (1997).
40. Jackson MA and King JW, Lipase-catalyzed glycerolysis of soybean oil in supercritical carbon dioxide. J Am Oil Chem Soc 74(2):103-106 (1997).
41. Adamczak M and Bednarski W, Application of enzymic glycerolysis for production of monoglycerides from waste fats. Pol J Food Nutr Sci 3 (1):129-33 (1994).
42. Akoh CC, Lipase-catalyzed synthesis of partial glyceride. Biotechnol Lett 15 (9):949-54 (1993).
43. Pecnik S and Knez Z, Enzymic fatty ester synthesis. J Am Oil Chem Soc 69 (3):261-265 (1992).
44. Papendorf O, Steffen B, Lang S and Wagner F, Monoacylglycerols:(bio) chemical production and interfacial properties. Chimica Oggi 13(10): 17-20 (1995).
45. Steffen B, Ziemann A, Lang S and Wagner F, Enzymic monoacylation of trihydroxy compounds. Biotechnol Lett 14:773-778 (1992).
46. Steffen B, Lang S, Hamann D, Schneider P, Cammenga HK and Wagner F, Enzymic formation and physico-chemical behaviour of uncommon monoglycerides. J Fat Sc Technol 97:132-136 (1995).
47. Guo Z and Xu X, New opportunity for enzymatic modification of fats and oils with industrial potentials, Org Biomol Chem 3:2615-2619 (2005).
48. Liu XY, Guo FL, Wu LM, Liu YC and Liu ZL, Remarkable enhancement of antioxidant activity of vitamin C in an artificial bilayer by making it lipo-soluble. Chem Phys Lipids 83:39-43 (1996).
49. Humeau C, Girardin M, Rovel B and Miclo A, Effect of thermodynamic water activity and the reaction medium hydrophobicity on the enzymatic synthesis of acorbyl palmitate. J Biotechnol 63:1-8 (1998).
50. Humeau C, Girardin M, Rovel B and Miclo A, Enzymatic synthesis of fatty acid acorbyl esters. J Mol Catal B:Enzymatic 5:19-23 (1998).
51. Bradoo S, Saxena RK and Gupta R, High yields of ascorbyl palmitate by thermostable lipase-mediated esterification. J Am Oil Chem Soc 76 (11):1291-1295 (1999).
52. Yan Y, Bornscheuer UT and Schmid RD, Lipase catalyzed synthesis of vitamin-C fatty acid esters. Biotechnol Lett 21:1051-1054 (1999).
53. Watanabe Y, Minemoto S, Adachi S, Nakanishi K, Shimada Y and Matsuno R, Lipase-catalyzed synthesis of 6-O-eicosapentaenoyl L-ascorbic acid and its autoxidation. Biotechnol Lett 22:637-640 (1999).
54. Park S, Viklund F, Hult K and Kazlauskas RJ, Vacuum driven lipase-catalyzed direct condensation of L-ascorbic acid and fatty acids in ionic liquids:synthesis of a natural surface active antioxidant. Green Chem 5:715-719 (2003).
55. Hui Y, Xueju X and Paul SA, Lipase-catalyzed synthesis of C-6 saturated and unsaturated fatty acid esters of L-ascorbic acid. J Appl Glycosci 50 (3):373-378 (2003).
56. Hsieh H-J, Chen J-W, Giridhar R and Wu W-T, Synthesis of mixed esters of ascorbic acid using methyl esters of palm and soybean oils. Prep Biochem Biotechnol 35(2):113-118 (2005).
57. Adamczak M and Bornscheuer UT and Bednarski W, Synthesis of ascorbyloleate by immobilized Candida antarctica lipases. Process Biochem 40:3177-3180 (2005).
58. Feuge RO, Zeringue J, Weiss TJ and Brown M, Preparation of sucrose esters by interesterification. J Am Oil Chem Soc 47:56-60 (1970).
59. Sarney DB, Kapeller H, Fregapane G and Vulfson EN, Chemo-enzymatic synthesis of disaccharide fatty acid esters. J Am Oil Chem Soc 71:711-714 (1994).
60. Ferrer M, Cruces MA, Bernabe M, Ballesteros A and Plou FJ, Lipase-catalyzed regioselective acylation of sucrose in two-solvent mixtures. Biotechnol Bioengg 65(1):10-16 (1999).
61. Plou FJ, Cruces MA, Ferrer M, Fuentes G, Pastor E, Bernabe M et al., Enzymatic acylation of di-and trisaccharides with fatty acids:choosing the appropriate enzyme, support and solvent. J Biotechnol 96:55-66 (2002).
62. Chopineau J, McCafferty FD, Therisod M and Klibanov AM, Production of bio-surfactants from sugar alcohols and vegetable oils catalyzed by lipases in a nonaqueous medium. Biotechnol Bioeng 31:208-214 (1988).
63. Janssen AEM, Lefferts AG and Riet K, Enzymatic synthesis of carbohydrate esters in aqueous media. Biotechnol Lett 12:711-716 (1990).
64. Riva S, Chopineau J, Kieboom APG and Klibanov AM, Protease-catalyzed regioselective esterification of sugars and related compounds in anhydrous dimethylformamide. J Am Oil Chem Soc 110:584-589 (1988).
65. Sharma A and Chattopadhyay S, Lipase catalysed acylation of carbohydrates. Biotechnol Lett 15:1145-1193 (1993).
66. Fregapane G, Sarney DB and Vulfson EN, Enzymatic solvent-free synthesis of sugar acetal fatty acid esters. Enz Microb Technol 13: 796-800 (1991).
67. Adelhorst K, Björkling F, Godtfredsen SE and Kirk O, Enzyme catalysed preparation of 6-O-acylglucopyranosides. Synthesis 2:112-115 (1990).
68. Ikeda I, Klibanov AM, Lipase-catalyzed acylation of sugars solubilized in hydrophobic solvents by complexation. Biotechnol Bioeng 42(6):788-791(1993).
69. Pulido R, López FO and Gotor V, Enzymatic regioselective acylation of hexoses and pentoses using oxime esters. J Chem Soc Perkin Trans 1:2981-2988 (1992).
70. Björkling F, Godtfredsen SE and Kirk O, The future impact of industrial lipases. Trends Biotech 9:360-363 (1991).
71. Cao L, Bornscheuer UT and Schmid RD, Lipase-catalyzed solid phase synthesis of sugar esters. Fat Sci Technol 98:332-335 (1996).
72. Cao L, Bornscheuer UT and Schmid RD, Lipase-catalyzed solid phase synthesis of sugar esters, IV:Selectivity of lipases towards primary and secondary hydroxyl groups in carbohydrates. Biocatal Biotransform 16:249-257 (1998).
73. Cao L, Bornscheuer UT and Schmid RD, Lipase-catalyzed solid-phase synthesis of sugar esters. Influence of immobilization on productivity and stability of the enzyme. J Mol Catal B:Enzymatic 6:279-285 (1999).
74. Cao L, Fischer A, Bornscheuer UT and Schmid RD, Lipase-catalyzed solid phase synthesis of sugar fatty acid esters. Biocatal Biotransform 14:269-283 (1997).
75. Saxena RK, Isar J, Saran S, Kaushik R and Davidson WS, Efficient microwave-assisted hydrolysis of triolein and synthesis of bioester, bio-surfactant and glycerides using Aspergillus carneus lipase. Curr Sc 89 (6):1000-1003 (2005).
76. Šabeder S, Habulin M and Knez Ž, Lipase-catalyzed synthesis of fatty acid fructose esters. J Food Eng 77(4):880-886 (2006)
77. Ganske F and Bornscheuer UT, Lipase-catalyzed glucose fatty acid ester synthesis in ionic liquids. Org Lett 7:3097-3098 (2005).
78. Arcos JA, Bernabe M and Otero C, Quantitative enzymatic production of 1,6-diacyl sorbitol esters. Biotechnol Bioeng 60(1):53-60 (1998).
79. Arcos JA, Bernabe M and Otero C, Quantitative enzymatic production of 6-O-acylglucose esters. Biotechnol Bioeng 57(5):505-509 (1998).
80. Ferrer M, Cruces MA, Plou FJ, Bernabe M and Ballesteros A, A simple procedure for the regioselective synthesis of fatty acid esters of maltose, leucrose, maltotriose and n-dodecyl maltosides. Tetrahedron 56:4053-4061 (2000).
81. Peter D, Pedersen, LH, Duus J and Zimmermann W, Lipase-catalysed synthesis of glucose fatty acid esters in tert-butanol. Biotechnol Lett 21:275-280 (1999).
82. Tsuzuki W, Kitamura Y, Suzuki T and Kobayashi S, Synthesis of sugar fatty acid esters by modified lipase Biotechnol Bioeng 64(3):267-271 (1999).
83. Ferrer M, Soliveri J, Plou FJ, Lopez-Cortes N, Reyes-Duarte D, Christensen M et al., Synthesis of sugar esters in solvent mixtures by lipases from thermomyces lanuginosus and Candida antarctica-B, and their antimicrobial properties. Enz Microb Technol 36:391-398 (2005).
84. Polat T, Bazin HG and Linhardt RJ, Enzyme catalyzed regioselective synthesis of sucrose fatty acid ester surfactants. J Carbohydr Chem 16:1319-1325 (1997).