Bioconversion of Renewables-Plant Oils

Biocatalysis for Green Chemistry and Chemical Process Development

Volumn , Issue , 2011, Pages 391-427

  Schneider, Manfred P ^a  

^a UNIVERSITY OF WUPPERTAL   (Germany)

Author keywords

"monoglycerides"; Bioconversion of renewables plant oils; Emulsifiers for food processing cosmetical applications, excipients for pharmaceuticals; Having a long tradition; Lipase catalyzed transformations for lipid modification dietary applications

Indexed keywords

EID: 84886033306     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781118028308.ch15     Document Type: Chapter

References (104)

1. USDA. http://www.fas.usda.gov/oilseeds/circular/Current.asp. Accessed year: 13/12/2009
2. Schneider M. Review: plant-oil-based lubricants and hydraulic fluids. J Sci Food Agric 2006;86:1769-1780.
3. Metzger JO. Fats and oils as renewable feedstock for chemistry. Eur J Lipid Technol 2009;111:865-876.
4. Berger M, Schneider MP. Regioselectivity of Lipases in organic Solvents. Biotechnol Lett 1991;13:333-338.
5. Schmid RD, Verger R. Lipases: interfacial enzymes with attractive applications. Angew Chem Int Ed 1998;37:1608-1633.
6. Berger M, Schneider MP. Enzymatic esterification of glycerol II. Lipase-catalyzed synthesis of regioisomerically pure 1(3) - rac-monoacylglycerols. J Am Oil Chem Soc 1992;69:961-965.
7. Berger M, Schneider MP. Lipases in organic solvents: the fatty acid chain length profile. Biotechnol Lett 1991;13:641-645.
8. Berger M, Laumen K, Schneider MP. Enzymatic esterification of glycerol I. Lipasecatalyzed synthesis of regioisomerically pure 1,3-sn-diacylglycerols. J Am Oil Chem Soc 1992;69:955-960.
9. Waldinger C, Schneider MP. Enzymatic esterification of glycerol III. Lipase catalyzed synthesis of regioisomerically pure 1,3-sn-diacylglycerols and 1(3)-racmonoacylglycerols derived from unsaturated fatty acids. J Am Oil Chem Soc 1996;73:1513-1519.
10. Wongsakul S, H-Kittikun A, Bornscheuer UT. Lipase-catalyzed synthesis of structured triacylglycerides from 1,3-diacylglycerides. J Am Oil Chem Soc 2004;81:151-155.
11. Halldorsson A, Magnusson CD, Haraldsson GG. Chemoenzymatic synthesis of structured triacylglycerols. Tetrahedron Lett 2001;42:7675-7677.
12. Kristensen JB, Xu X, Mu H. Diacylglycerol synthesis by enzymatic glycerolysis: screening of commercially available lipases. J Am Oil Chem Soc 2005;82:329-334.
13. Castillo E, Dossat V, Marty A, Condoret JS, Combes D. The role of silica gel in lipase-catalyzed esterifcation reactions of high polar substrates. J Am Oil Chem Soc 1997;74:77-85.
14. Lobell M, Schneider M. Synthesis of hydroxycarboxylic acid vinyl esters. Synthesis 1994:375-377.
15. Rosu R, Yasui M, Iwasaki Y, Yamane T. Enzymatic synthesis of symmetrical 1,3-diacylglycerols by direct esterification of glycerol in solvent-free system. J Am Oil Chem Soc 1999;76:839-843;
16. Hobbs HR, Thomas NR. Biocatalysis in supercritical fluids, in fluorous solvents, and under solvent-free conditions. Chem Rev 2007;107:2786-2820;
17. van Rantwijk F, Sheldon RA. Biocatalysis in ionic liquids. Chem Rev 2007;107:2757-2785;
18. Hilterhaus L, Thum O, Liese A. Reactor concept for lipase-catalyzed solvent-free conversion of highly viscous reactants forming two-phase systems. Org Process Res Dev 2008;12:618-625.
19. Berger M, Schneider MP. Regioisomerically pure mono- and diacylglycerols as synthetic building blocks. Fat Sci Technol 1993;95:169-175.
20. Haftendorn R, Ulbrich-Hofmann R. Synthesis of 2-modified diacylglycerols. Tetrahedron 1995;51:1177-1186. 18. Haftendorn R, Schwarze G, Ulbrich-Hofmann R. 1,3-Diacylglycero-2-phosphocholines- synthesis, aggregation behavior and properties as inhibitors of phospholipase D. Chem Phys Lipids 2000;104:57-66.
21. Haftendorn R, Schwarze G, Ulbrich-Hofmann R. 1,3-Diacylglycero-2-phosphocholines- synthesis, aggregation behavior and properties as inhibitors of phospholipase D. Chem Phys Lipids 2000;104:57-66.
22. Ulbrich-Hofmann R. Phospholipases used in lipid transformations. In: Bornscheuer UT, editor. Enzymes in lipid modification. Weinheim, Germany: Wiley-VCH; 2000. pp. 219-262.
23. El Kihel L, Bourass J, Richomme P, Petit JY, Letourneux P. Synthesis and evaluation of the anti-inflammatory effects of niflumic acid lipophilic prodrugs in brain edema. Drug Res 1996;46:1040-1044.
24. Mantelli S, Speiser P, Hauser H. Phase behavior of diglyceride prodrugs: spontaneous formation of unilamellar vesicles. Chem Phys Lipids 1985;37:329-343.
25. Scriba GKE. Phenytoin-lipid conjugates as potential prodrugs of phenytoin. Arch Pharm 1993;326:477-481.
26. Baumann H, Bühler M, Fochem H, Hirsinger F, Zoebelein H, Falbe J. Natural fats and oils-renewable raw materials for the chemical industry. Angew Chem Int Ed Engl 1988;27:41-62.
27. Kato Y, Fujiwara I Asano Y. Synthesis of optically active a-monobenzoyl glycerol by asymmetric transesterification of glycerol. J Molec Catal B Enzym 2000;9:193-200;
28. Heidt M, Bornscheuer U, Schmid RD. Studies on the enantioselectivity in the lipase-catalyzed synthesis of monoacyl glycerols from isopropylidene glycerol. Biotechnol Tech 1996;10:25-50.
29. Breitgoff D, Laumen K, Schneider MP. Enzymatic differentiation of the enantiotopic hydroxymethyl groups of glycerol; synthesis of chiral building blocks. J Chem Soc, Chem Commun 1986:1523-1524;
30. Breitgoff D, dissertation Wuppertal. 1989.
31. Schneider M, Laumen K, Breitgoff D, Wullbrandt D, Schlingmann M, Keller R. Chiral synthetic building blocks from prochiral glycerol. 3624703 A1. 1986.
32. Soumanou MM, Bornscheuer UT, Schmid RD. Two-step enzymatic reaction for the synthesis of pure structured triacylglycerols. J Am Oil Chem Soc 1998;75:703-710.
33. Irimescu R, Iwasaki Y, Hou CT. Study of TAG ethanolysis to 2-MAG by immobilized Candida antarctica lipase and synthesis of symmetrically structured TAG. J Am Oil Chem Soc 2002;79:879-883.
34. Millquist A, Adlercreutz P, Mattiason B. Lipase catalyzed alcoholysis of triglycerides for the preparation of 2-monoglycerides. Enzyme Microb Technol 1994;16:1042-1047.
35. Millquist A, Virto C, Adlercreutz P, Mattiason B. Acyl group migration in 2- monoolein. Biocatalysis 1996;14:89-111.
36. Wongsakul S, Prasertsan P, Bornscheuer UT, H-Kittikun A. Synthesis of 2- monoglycerides by alcoholysis of palm oil and tuna oil using immobilized lipases. Eur J Lipid Sci Technol 2003;105:68-73.
37. Diks RMM, Bosley JA. The exploitation of lipase selectivities for the production of acyl glycerols. In: Bornscheuer UT, editor. Enzymes in Lipid Modifications. Wiley- VCH; 2000. pp 3-22 and references therein.
38. Bornscheuer U. Lipase-catalyzed syntheses of mono acylglycerols (in German). Fat Sci Technol 1995;97:241-249.
39. Bornscheuer UT. Lipase-catalyzed syntheses of mono acylglycerols. Enzyme Microb Technol 1995;17:578-586.
40. Steffen B, Ziemann A, Lang S, Wagner F. Enzymatic monoacylation of trihydroxy compounds. Biotechnol Lett 1992;14:773-778.
41. Steffen B, Lang S, Hamann D, Schneider P, Cammenga HK, Wagner F. Enzymatic formation and physico-chemical behaviour of uncommon monoglycerides. Fat Sci Technol 1995;97:132-136.
42. Akoh CC. Lipase-catalyzed synthesis of partial glyceride. Biotechnol Lett 1993;15:949-954.
43. McNeill GP, Shimizu S, Yamane T. High-yield enzymatic glycerolysis of fats and oils. J Am Oil Chem Soc 1991;68:1-5.
44. McNeill GP, Yamane T. Further improvement in the yield of monoglycerides during enzymatic glycerolysis of fats and oils. J Am Oil Chem Soc 1991;68:6-10.
45. Bornscheuer UT, Yamane T. Activity and stability of lipase in the solid-phase glycerolysis of triolein. Enzyme Microb Technol 1994;16:864-869.
46. Watanabe Y, Yamauchi-Sato Y, Nagao T, Yamamoto T, Tsutsumi K, Sugihara A, Shimada Y. Production of MAG of CLA in a solvent-free system at low temperature with Candida rugosa lipase. J Am Oil Chem Soc 2003;80:909-914.
47. Pinsirodom P, Watanabe Y, Nagao T, Sugihara A, Koayashi T, Shimada Y. Critical temperature for production of MAG by esterification of different FA with glycerol using Penicillium camembertii lipase. J Am Oil Chem Soc 2004;81:543-547.
48. Elfman-Börjesson I, Härröd M. Synthesis of monoglycerides by glycerolysis of rapeseed oil using immobilized lipase. J Am Oil Chem Soc 1999;76:701-707;
49. see also: Selmi B, Gontier E, Ergan F, Thomas D. Enzymatic synthesis of tricaprylin in a solvent-free system: lipase regiospecificity as controlled by glycerol absorption on silica gel. Biotechnol Tech 1997;11:543-547, and many others.
50. Waldinger C. dissertation Wuppertal; 1995.
51. Berger M, Laumen K, Schneider MP. Lipase-catalyzed esterification of hydrophilic diols in organic solvents. Biotechnol Lett 1992;14:553-558.
52. For detailed discussions see: Xu X. Modification of oils and fats by lipasecatalyzed interesterification: aspects of process engineering. In: Bornscheuer UT, editor. Enzymes in Lipid Modifications. Weinheim, Germany: Wiley-VCH; 2000. pp. 190-215.
53. Matsuo N, Tokimitsu I. Metabolic characteristics of diacylglycerol. Inform 2001;12:1098-1102.
54. Hara K, Onizawa K, Honda T, Ide T, Otsuji K, Murata M. Dietary diacylglycerol - dependent reduction in serum triacylglycerol concentrations in rats. Ann Nutr Metab 1993;37:185-191.
55. Nagao T, Watanabe H, Goto N, Onizawa K, Taguchi H, Matsuao N, Yasukawa T, Tsushima R, Shimazaki H, Itakura H. Dietary diacylglycerol suppresses accumulation of body fat compared to triacylglycerol in men in a double blind trial. J Nutr 2000;130:792-797.
56. Sonntag NOV. New developments in the fatty acid industry in America. J Am Oil Chem Soc 1984;61:229-232.
57. Yokomichi H, Okauchi Y, Oka T, Okisaka M, Kokumai H, Koike S, Mori K, Tabeta M. Frying oil or fat composition. 5,514,405. 1996.
58. Watanabe T, Shimizu M, Sugiura M, Sato M, Kohori J, Yamada N, Nakanishi K. Optimization of reaction conditions for the production of DAG using immobilized, 1,3-regiospecific lipase Lipozyme RM IM. J Am Oil Chem Soc 2003;80:1201-1207.
59. Flickinger BD, Matsuo N. Nutritional characteristics of DAG oil. Lipids 2003;38:129-132.
60. Kristensen JB, Xu X, Hu M. Diacylglycerol synthesis by enzymatic glycerolysis: screening of commercially available lipases. J Am Oil Chem Soc 2005;82:329-334.
61. Jandacek RJ, Whitesides JA, Holcombe BN, Volpenheim RA, Taulbee JD. The rapid hydrolysis and efficient absorption of triglycerides with octanoic acid in the 1- and 3-positions and long chain fatty acids in the 2-position. Am J Clin Nutr 1997;45:940-945.
62. Bornscheuer UT, Adamczak M, Soumanou MM. In: Gunstone FD, Barnes PJ, associates, editors. Lipase-catalyzed synthesis of modified lipids. UK: Bridgewater; 2002. pp. 149-182;
63. Akoh CC. Structured lipids-enzymatic approach. Inform 1995;6:1055-1061.
64. Xu X. Review: Production of structured triacylglycerols by lipase-catalyzed reactions. Eur J Lipid Sci Technol 2000;102:287-303.
65. Soumanou MM, Bornscheuer UT, Schmid U, Schmid RD. Synthesis of structured triglycerides by lipase catalysis. Fett/Lipid 1998;100:156-160.
66. Wongsakul S, H-Kiikun A, Bornscheuer UT. Lipase-catalyzed synthesis of structured triacylglycerides from 1,3-diacylglycerides. J Am Oil Chem Soc 2004;81:151-155.
67. Christensen MS, Höy C-E, Becker CC, Redgrave TG. Intestinal absorption and lymphatic transport of eicosapentaenoic (EPA), docosahexaenoic (DHA) and decanoic acids: dependence on intramolecular triacylglycerol structure. Am J Clin Nutr 1995;61:56-61.
68. Haraldsson GG, Halldorsson A, Kulas E. Chemoenzymatic synthesis of structured triacylglycerols containing eicosapentaenoic and docosahexaenoic acids. J Am Oil Chem Soc 2000;77:1139-1145.
69. Haraldsson GG. Enrichment of lipids with EPA and DHA by lipase. In: Bornscheuer UT, editor. Enzymes in Lipid Modification. Weinheim, Germany: Wiley-VCH; 2000. pp. 170-189.
70. Yamane T. Lipase-catalyzed synthesis of structured triacylglycerols containing polyunsaturated fatty acids: monitoring the reaction and increasing the yield. In: Bornscheuer UT, editor. Enzymes in Lipid Modification. Weinheim, Germany: Wiley- VCH; 2000. pp. 148-169.
71. Adamczak M, Bornscheuer UT, Bednarski W. Review: properties and biotechnological methods to produce lipids containing conjugated linoleic acid. Eur J Lipid Sci Technol 2008;110:491-504.
72. Kennedy JF, Kumar H, Panesar PS, Marwaha SS, Goyal R, Parmar A, Kaur S. Review: Enzyme-catalyzed regioselective synthesis of sugar esters and related compounds. J Chem Technol Biotechnol 2006;81:866-876.
73. Tsuzuki W, Kitamura Y, Suzuki T, Kobayashi S. Synthesis of sugar fatty acid esters by modified lipase. Biotechnol Bioeng 1999;64:267-271.
74. Schlottterbeck A, Lang S, Wray V, Wagner F. Lipase-catalyzed monoacylation of fructose. Biotechnol Lett 1993;15:61-64.
75. Yan Y, Bornscheuer UT, Stadler G, Lutz-Wahl S, Otto RT, Reuss M, Schmid RD. Regioselective glucose ester synthesis on a preparative scale. Eur J Lipid Sci Technol 2001;103:583-587, and literature cited therein.
76. Schneider MP, Haase B, Machmüller G. Enzyme-catalyzed procedure for the preparation of mono esters of mono-, di- and oligosaccharides. DE 19626943.1. 1996;
77. Schneider M, Haase B, Machmueller G, Chem Abstr 1998;128:127145t; (c) Machmüller G. dissertation Wuppertal; 2004;
78. for studies of the gel properties see also: John G, Zhu G, Li J, Dordick JS. Enzymatically derived sugar-containing self-assembled organogels with nanostructured morphologies. Angew Chem Int Ed 2006;45:4772-4775.
79. Yan Y, Bornscheuer UT, Schmid RD. Lipase-catalyzed synthesis of vitamin C fatty acid esters. Biotechnol Lett 1999;21:1051-1054.
80. Adamczak M, Bornscheuer UT, Bednarski W. Synthesis of ascorbyloleate by immobilized Candida Antarctica lipases. Process Biochem 2005;40:3177-3180.
81. Park S, Kazlauskas RJ. Improved preparation and use of room-temperature ionic liquids in lipase-catalyzed enantio- and regioselective acylations. J Org Chem 2001;66:8395-8401.
82. Adamczak M, Bornscheuer UT. Improving ascorbyl oleate synthesis catalyzed by Candida antarctica lipase B in ionic liquids and water activity control by salt hydrates. Process Biochem 2009;44:257-261.
83. Infante MR, Perez L, Pinazo A, Clapes P, Moran MC, Angelet M, Garcia MT, Vinardell MP. Amino acid-based surfactants. C R Chimie 2004;7:583-592.
84. Müller S. dissertation Wuppertal. 2000.
85. Goujard L, Figuera MC, Villeneuve P. Chemo-enzymatic synthesis of N-arachidonyl glycine. Biotechnol Lett 2004;26:1211-1216.
86. Godtfredsen SE, Björkling F. An enzyme-catalyzed process for preparing N-acyl amino acids and N-acyl amino acid amides. WO 90/14429. 1990.
87. Biermann U, Friedt W, Lang S, Lühs W, Machmüller G, Metzger JO, Rüsch gen Klass M, Schäfer HJ, Schneider MP. New syntheses with oils and fats as renewable raw materials for the chemical industry. Angew Chem Int Ed 2000;39:2206-2224.
88. Björkling F, Godtfredsen SE, Kirk O. Lipase - mediated formation of peroxycarboxylic acids used in catalytic epoxidations of alkenes. J Chem Soc, Chem Commun 1990:1301-1303.
89. Björkling F, Frykman SE, Godtfredsen SE, Kirk O. Lipase-catalyzed synthesis of peroxy carboxylic acids and lipase-mediated epoxidations. Tetrahedron 1992;48:4587-4592.
90. Rüsch gen Klaas M,Warwel S. Lipase-catalyzed peroxy fatty acid generation and lipid oxidation. In: Bornscheuer UT, editor. Enzymes in Lipid Modification. Weinheim, Germany: Wiley-VCH; 2000. pp. 116-127.
91. Warwel S, Rüsch gen Klaas M. New peroxycarbonic acids by enzyme catalysis-syntheses and oxidation properties. In: Adam W, editor. Peroxide chemistry, mechanistic and preparative aspects of oxygen transfer. Wiley-VCH: 2001.
92. Iacazio G, Martini-Iacazio D. Properties and applications of lipoxygenases. In: Bornscheuer U, editor. Enzymes in Lipid Modification. Weinheim, Germany: Wiley-VCH; 2000. pp. 337-359.
93. Fussner I, Kühn H. Application of lipoxygenases and related enzymes for the preparation of oxygenated lipids. In: Bornscheuer U, editor. Enzymes in Lipid Modification. Weinheim, Germany: 2000; Wiley-VCH. pp. 309-336.
94. http://www.emerging-markets.com/biodiesel. Access year: 10/12/2009
95. Echim C, Verhe R, De Greyt W, Stevens C. Production of biodiesel from side-stream refining products. Energy Environ Sci 2009;2:1131-1141.
96. Nielsen PM, Brask J, Fjerbaeck L. Enzymatic biodiesel production: technical and economical considerations. Eur J Lipid Sci Technol 2008;110:692-700.
97. Adamczak M, Bornscheuer UT, Bednarski W. Review: the application of biotechnological methods for the synthesis of biodiesel. Eur J Lipid Sci Technol 2009;111:808-813, and literature cited therein.
98. Fjerbaeck L, Christensen KK, Norddahl B. A Review of current state of biodiesel production using enzymatic transesterification. Biotechnol Bioeng 2009;102:1298-1315.
99. Mittelbach M. Lipase catalyzed alcoholysis of sunflower oil. J Am Oil Chem Soc 1990;67:168-170.
100. Shimada Y, Watanabe Y, Sugihara A, Tominaga Y. Enzymatic alcoholysis for biodiesel production and application of the reaction to oil processing. J Mol Catal B Enzym 2002;17:133-142.
101. Du W, Li W, Sun T, Chen X, Liu D. Perspectives for biotechnological production of biodiesel and impacts. Appl Microbiol Biotechnol 2008;79:331-337.
102. http://www.biodieselmagazine.com/article.jsp?articleid_2416and2537. Accessed year: 9/12/2009
103. Kalscheuer R, Stolting T, Steinbüchel A. Microdiesel:Escherichia coli engineered for fuel production. Microbiology 2006;152:2529-2536.
104. Steen EJ, Kang Y, Bokinsky G, Hu Z, Schirmer A, McClure A, del Cardayre SB, Keasling JD. Microbial production of fatty acid derived fuels and chemicals from plant biomass. Nature 2010;463:559-563.