New biofuel integrating glycerol into its composition through the use of covalent immobilized pig pancreatic lipase

International Journal of Molecular Sciences

Volumn 13, Issue 8, 2012, Pages 10091-10112

  Luna, Diego ^a   Posadillo, Alejandro ^b   Caballero, Verónica ^a   Verdugo, Cristóbal ^c   Bautista, Felipa M ^a   Romero, Antonio A ^a   Sancho, Enrique D ^a   Luna, Carlos ^a   Calero, Juan ^a  

^a UNIVERSITY OF CÓRDOBA   (Spain)

^b Seneca Green Catalyst SL Campus de Rabanales ^*  (Spain)

^c LABORATORIO DE ESTUDIOS CRISTALOGRÁFICOS   (Spain)

Author keywords

Biofuels; Covalent immobilization; Monoglyceride; Pig pancreatic lipase (PPL); Sepiolite; Sunflower oil transesterification

Indexed keywords

ALCOHOL; ALUMINUM PHOSPHATE; BIODIESEL; FATTY ACID ESTER; GLYCEROL; MAGNESIUM TRISILICATE; MONOACYLGLYCEROL; SUNFLOWER OIL; TRIACYLGLYCEROL LIPASE; ALCOHOL DERIVATIVE; BIOFUEL; FATTY ACID; IMMOBILIZED ENZYME; VEGETABLE OIL;

ARRHENIUS PARAMETER; ARTICLE; BIOCATALYST; CHEMICAL COMPOSITION; CHEMICAL PARAMETERS; COMPARATIVE STUDY; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; COVALENT BOND; ENZYME IMMOBILIZATION; ENZYME STABILITY; FACILE RECYCLABILITY; INTERMETHOD COMPARISON; MOLECULAR WEIGHT; NONHUMAN; PHYSICAL CHEMISTRY; REACTION ANALYSIS; RECYCLING; TRANSESTERIFICATION; ANIMAL; CHEMISTRY; ESTERIFICATION; GAS CHROMATOGRAPHY; METABOLISM; PIG; TEMPERATURE; VISCOSITY;

ALCOHOLS; ANIMALS; BIOFUELS; CHROMATOGRAPHY, GAS; ENZYMES, IMMOBILIZED; ESTERIFICATION; FATTY ACIDS; GLYCEROL; LIPASE; PLANT OILS; SWINE; TEMPERATURE; VISCOSITY;

EID: 84865007049     PISSN: 16616596     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms130810091     Document Type: Article

References (80)

1. Vyas, A.P.; Verma, J.L.; Subrahmanyam, N. A review on FAME production processes. Fuel 2010, 89, 1-9.
2. Meher, L.C.; Vidya Sagar, D.; Naik, S.N. Technical aspects of biodiesel production by transesterification-A review. Renew. Sustain. Energy Rev. 2006, 10, 248-268.
3. Fukuda, H.; Kondo, A.; Noda, H. Biodiesel fuel production by transesterification of oils. J. Biosci. Bioeng. 2001, 92, 405-416.
4. Faria, E.A.; Ramalho, H.F.; Marques, J.S.; Suarez, P.A.Z.; Prado, A.G.S. Tetramethylguanidine covalently bonded onto silica gel surface as an efficient and reusable catalyst for transesterification of vegetable oil. Appl. Catal. A Gen. 2008, 338, 72-78.
5. Cerce, T.; Peter, S.; Weidner, E. Biodiesel-transesterification of biological oils with liquid catalysts: Thermodynamic properties of oil-methanol-amine mixtures. Ind. Eng. Chem. Res. 2005, 44, 9535-9541.
6. Viola, E.; Blasi, A.; Valerio, V.; Guidi, I.; Zimbardia, F.; Braccioa, G.; Giordano, G. Biodiesel from fried vegetable oils via transesterification by heterogeneous catalysis. Catal. Today 2012, 179, 185-190.
7. Semwal, S.; Arora, A.K.; Badoni, R.P.; Tuli, D.K. Review: Biodiesel production using heterogeneous catalysts. Bioresour. Technol. 2011, 102, 2151-2161.
8. Lee, D.W.; Park, Y.M.; Lee, K.Y. Heterogeneous base catalysts for transesterification in biodiesel synthesis. Catal. Surv. Asia 2009, 13, 63-77.
9. Melero, J.A.; Iglesias, J.; Morales, J. Heterogeneous acid catalysts for biodiesel production: Current status and future challenges. Green Chem. 2009, 11, 1285-1308.
10. Andrijanto, E.; Dawson, E.A.; Brown, D.R. Hypercrosslinked polystyrene sulphonic acid catalysts for the esterification of free fatty acids in biodiesel synthesis. Appl. Catal. B Environ. 2012, 115, 261-268.
11. Arancon, R.A.; Barros, H.R., Jr.; Balu, A.M.; Vargas, C.; Luque, R. Valorisation of corncob residues to functionalised porous carbonaceous materials for the simultaneous esterification/transesterification of waste oils. Green Chem. 2011, 13, 3162-3167.
12. Borges, M.E.; Díaz, L. Recent developments on heterogeneous catalysts for biodiesel production by oil esterification and transesterification reactions: A review. Renew. Sustain. Energy Rev. 2012, 16, 2839-2849.
13. Ranganathan, S.V.; Narasimhan, S.L.; Muthukumar, K. An overview of enzymatic production of biodiesel. Bioresour. Technol. 2008, 99, 3975-3981.
14. Nielsen, P.M.; Rancke-Madsen, A. Enzymatic large-scale production of biodiesel. Lipid Technol. 2011, 23, 230-233.
15. Fan, X. Enzymatic biodiesel production-The way of the future. Lipid Technol. 2012, 24, 31-32.
16. Gog, A.; Roman, M.; Tos, M.; Paizs, C.; Irimie, F.D. Biodiesel production using enzymatic transesterification-Current state and perspectives. Renew. Energy 2012, 39, 10-16.
17. Behr, A.; Eilting, J.; Leschinski, J.; Lindner, F. Improved utilisation of renewable resources: New important derivatives of glycerol. Green Chem. 2008, 10, 13-30.
18. Corma, A.; Huber, G.W.; Sauvanaud, L.; O'Connor, P. Processing biomass-derived oxygenates in the oil refinery: Catalytic cracking (FCC) reaction pathways and role of catalyst. J. Catal. 2007, 247, 307-327.
19. Adamczak, M.; Bornscheuer, U.T.; Bednarski, W. The application of biotechnological methods for the synthesis of biodiesel. Eur. J. Lipid Sci. Technol. 2009, 111, 808-813.
20. Luque, R.; Herrero-Davila, L.; Campelo, J.M.; Clark, J.H.; Hidalgo, J.M.; Luna, D.; Marinas, J.M.; Romero, A.A. Biofuels: A technological perspective. Energy Environ. Sci. 2008, 1, 513-596.
21. Vasudevan, P.T.; Briggs, M. Biodiesel production-Current state of the art and challenges. J. Ind. Microbiol.Biotechnol. 2008, 35, 421-430.
22. Fabbri, D.; Bevoni, V.; Notari, M.; Rivetti, F. Properties of a potential biofuel obtained from soybean oil by transmethylation with dimethyl carbonate. Fuel 2007, 86, 690-697.
23. Kenar, J.A.; Knöthe, G.; Dunn, R.O.; Ryan, T.W.; Matheaus, A. Physical properties of oleochemical carbonates. J. Am. Oil Chem. Soc. 2005, 82, 201-205.
24. Su, E.Z.; Zhang, M.J.; Zhang, J.G.; Gao, J.F.; Wei, D.Z. Lipase-catalyzed irreversible transesterification of vegetable oils for fatty acid methyl esters production with dimethyl carbonate as the acyl acceptor. Biochem. Eng. J. 2007, 36, 167-173.
25. Ilham, Z.; Saka, S. Two-step supercritical dimethyl carbonate method for biodiesel production from Jatropha curcas oil. Bioresour. Technol. 2010, 101, 2735-2740.
26. Zhang, L.; Sheng, B.; Xin, Z.; Liu, Q.; Sun, S. Kinetics of transesterification of palm oil and dimethyl carbonate for biodiesel production at the catalysis of heterogeneous base catalyst. Bioresour. Technol. 2010, 101, 8144-8150.
27. Xu, Y.; Du, W.; Liu, D.; Zeng, J. A novel enzymatic route for biodiesel production from renewable oils in a solvent-free medium. Biotechnol. Lett. 2003, 25, 1239-1241.
28. Xu, Y.; Du, W.; Liu, D. Study on the kinetics of enzymatic interesterification of triglycerides for biodiesel production with methyl acetate as the acyl acceptor. J. Mol. Catal. B Enzym. 2005, 32, 241-245.
29. Du, W.; Xu, Y.; Liu, D.; Zeng, J. Comparative study on lipase-catalyzed transformation of soybean oil for biodiesel production with different acyl acceptors. J. Mol. Catal. B Enzym. 2004, 30, 125-129.
30. Akoh, C.C.; Chang, S.W.; Lee, G.C.; Shaw, J.F. Enzymatic approach to biodiesel production. J. Agric. Food Chem. 2007, 55, 8995-9005.
31. Ognjanovic, N.; Bezbradica, D.; Knezevic-Jugovic, Z. Enzymatic conversion of sunflower oil to biodiesel in a solvent-free system: Process optimization and the immobilized system stability Bioresour. Technol. 2009, 100, 5146-5154.
32. Modi, M.K.; Reddy, J.R.C.; Rao, B.; Prasad, R.B.N. Lipase-mediated conversion of vegetable oils into biodiesel using ethyl acetate as acyl acceptor. Bioresour. Technol. 2007, 98, 1260-1264.
33. Kim, S.J.; Jung, S.M.; Park, Y.C.; Park, K. Lipase catalyzed transesterification of soybean oil using ethyl acetate, an alternative acyl acceptor. Biotechnol. Bioprocess Eng. 2007, 12, 441-445.
34. Casas, A.; Ruiz, J.R.; Ramos, M.J.; Pérez, A. Effects of triacetin on biodiesel quality. Energy Fuels 2010, 24, 4481-4489.
35. Sangsri, P.; Ratanawilai, S.; Meyer, P.; Tongurai, C. Feasibility of Biodiesel Production from Transmethylation of Used Cooking Oil. In Proceedings of the 5th PSU-UNS International Conference on Engineering and Technology (ICET-2011), Phuket, Prince of Songkla University, Faculty of Engineering Hat Yai, Songkhla, Thailand, 2-3 May 2011; pp. 92-95.
36. Caballero, V.; Bautista, F.M.; Campelo, J.M.; Luna, D.; Marinas, J.M.; Romero, A.A.; Hidalgo, J.M.; Luque, R.; Macario, A.; Giordano, G. Sustainable preparation of a novel glycerol-free biofuel by using pig pancreatic lipase: Partial 1,3-regiospecific alcoholysis of sunflower oil. Process Biochem. 2009, 44, 334-342.
37. Verdugo, C.; Luque, R.; Luna, D.; Hidalgo, J.M.; Posadillo, A.; Sancho, E.; Rodríguez, S.; Ferreira-Días, S.; Bautista, F.M.; Romero, A.A. A comprehensive study of reaction parameters in the enzymatic production of novel biofuels integrating glycerol into their composition. Bioresour. Technol. 2010, 101, 6657-6662.
38. Luna, D.; Bautista, F.M.; Caballero, V.; Campelo, J.M.; Marinas, J.M.; Romero, A.A. Method for producing biodiesel using porcine pancreatic lipase as an enzymatic catalyst. European Patent EP 2 050 823 A1; 22 April 2009.
39. Verdugo, C.; Luna, D.; Posadillo, A.; Sancho, E.; Rodríguez, S.; Bautista, F.M.; Luque, R.; Marinas, J.M.; Romero, A.A. Production of a new second generation biodiesel with a low cost lipase derived from Thermomyces lanuginosus: Optimization by response surface methodology. Catal. Today 2011, 167,107-112.
40. Knöthe, G.; Steidley, K.R. Kinematic viscosity of biodiesel components (fatty acid alkyl esters) and related compounds at low temperatures. Fuel 2007, 86, 2560-2567.
41. Wadumesthrige, K.; Ara, M.; Salley, S.O.; Ng, K.Y.S. Investigation of lubricity characteristics of biodiesel in petroleum and synthetic fuel. Energy Fuels 2009, 23, 2229-2234.
42. Xu, Y.; Wnag, Q.; Hu, X.; Li, C.; Zhu, X. Characterization of the lubricity of bio-oil/diesel fuel blends by high frequency reciprocating test rig. Energy 2010, 35, 283-287.
43. Sarin, R.; Arora, A.K.; Ranjan, R.; Gupta, A.A.; Malhotra, R.K. Biodiesel lubricity: Correlation study with residual acidity. Lubr. Sci. 2007, 19, 151-157.
44. Haseeb, A.S.M.A.; Sia, S.Y.; Fazal, M.A.; Masjuki, H.H. Effect of temperature on tribological properties of palm biodiesel. Energy 2010, 35, 1460-1464.
45. Tan, T.; Lu J.; Nie, K.; Deng, L.; Wang, F. Biodiesel production with immobilized lipase: A review. Biotechnol. Adv. 2010, 28, 628-634.
46. Diego, T.; Manjón, A.; Lozano, P.; Iborra, J.L. A recyclable enzymatic biodiesel production process in ionic liquids. Bioresour. Technol. 2011, 102, 6336-6339.
47. Bautista, F.M.; Bravo, M.C.; Campelo, J.M.; Garcia, A.; Luna, D.; Marinas, J.M.; Romero, A.A. Covalent immobilization of porcine pancreatic lipase on amorphous AlPO4 and other inorganic supports. J. Chem. Technol. Biotechnol. 1998, 72, 249-254.
48. Macario, A.; Giordano, G.; Setti, L.; Parise, A.; Campelo, J.M.; Marinas, J.M.; Luna, D. Study of lipase immobilization on zeolitic support and transesterification reaction in a solvent free-system. Biocatal. Biotransform. 2007, 25, 328-335.
49. Nunes, P.A.; Pires-Cabral, P.; Guillen, M.; Valero, F.; Luna, D.; Ferreira-Dias, S. Production of MLM-Type structured lipids catalyzed by immobilized heterologous rhizopus oryzae lipase. J. Am. Oil Chem. Soc. 2011, 88, 473-480.
50. Osorio, N.; Maeiro, I.; Luna, D.; Ferreira-Dias, S. Interesterification of fat blends rich in Ω-3 polyunsaturated fatty acids catalyzed by immobilized lipase on modified sepiolite. New Biotechnol. 2009, 255, 5111-5112.
51. Bautista, F.M.; Bravo, M.C.; Campelo, J.M.; Garcia, A.; Luna, D.; Marinas, J.M.; Romero, A.A. Covalent immobilization of acid phosphatase on amorphous AlPO4 support. J. Mol. Catal. B Enzym. 1999, 6, 473-481.
52. Bautista, F.M.; Campelo, J.M.; Garcia, A.; Jurado, A.; Luna, D.; Marinas, J.M.; Romero, A.A. Properties of a glucose oxidase covalently immobilized on amorphous AlPO4 support. J. Mol. Catal. B Enzym. 2001, 11, 567-577.
53. Luna, D.; Bautista, F.M.; Garcia, A.; Campelo, J.M.; Marinas, J.M.; Romero, A.A., Llobet, A.; Romero, I.; Serrano, I. Method for the chemical binding of homogeneous catalysts to inorganic solids supports, products thus obtained and application of same. International Publication No. WO 2004/096442 A1, 11 November 2004.
54. Bautista, F.M.; Caballero, V.; Campelo, J.M.; Luna, D.; Marinas, J.M.; Romero, A.A.; Romero, I.; Serrano, I.; Llobet, A. Heterogeneization of a new Ru(II) homogeneous asymmetric hydrogenation catalyst containing BINAP and the N-tridentate BPEA ligand, through covalent attachment on amorphous AlPO4 support. Topics Catal. 2006, 40, 193-205.
55. Mateo, C.; Palomo, J.M.; Fernandez-Lorente, G.; Guisan J.M. Improvement of enzyme activity, stability and selectivity via immobilization techniques. Enzym. Microb. Technol. 2007, 40, 1451-1463.
56. Sheldon, R.A. Enzyme immobilization: The quest for optimum performance. Adv. Synth. Catal. 2007, 349, 1289-1307.
57. Gutarra, M.L.E.; Romero, O.; Abian, O.; Torres, F.A.G.; Freire, D.M.G.; Castro, A.M.; Guisan, J.M.; Palomo, J.M. Enzyme surface glycosylation in the solid phase: Improved activity and selectivity of Candida Antarctica Lipase B. ChemCatChem 2011, 3, 1902-1910.
58. Wang, Z.G.; Wan, L.S.; Liu, Z.M.; Huang, X.J.; Xu, Z.K. Enzyme immobilization on electrospun polymer nanofibers: An overview. J. Mol. Catal. B Enzym. 2009, 56, 189-195.
59. Wang, Y.; Caruso, F. Mesoporous silica spheres as supports for enzyme immobilization and encapsulation. Chem. Mater. 2005, 17, 953-961.
60. Reshmi, R.; Sanjay, G.; Sugunan, S. Immobilization of α-amylase on zirconia: A heterogeneous biocatalyst for starch hydrolysis. Catal. Commun. 2007, 8, 393-399.
61. Jung, D.; Streb, C.; Hartmann, M. Covalent anchoring of chloroperoxidase and glucose oxidase on the mesoporous molecular sieve SBA-15. Int. J. Mol. Sci. 2010, 11, 762-778.
62. Maria Chong, A.S.; Zhao, X.S. Functionalized nanoporous silicas for the immobilization of penicillin acylase. Appl. Surf. Sci. 2004, 237, 398-404.
63. Šulek, F.; Drofenik, M.; Habulin, M.; Knez, Ž. Surface functionalization of silica-coated magnetic nanoparticles for covalent attachment of cholesterol oxidase. J. Magn. Magn. Mater. 2010, 322, 179-185.
64. Wilson, S.T.; Lok, B.M.; Messina, C.A.; Cannan, T.R.; Flanigen, E.M. Aluminophosphate molecular sieves: A new class of microporous crystalline inorganic solids. J. Am. Chem. Soc. 1982, 104, 1146-1147.
65. Elanany, M.; Koyama, M.; Kubo, M.; Selvam, P.; Miyamoto, A. Periodic density functional investigation of Brønsted acidity in isomorphously substituted chabazite and AlPO-34 molecular sieves. Micropor. Mesopor. Mater. 2004, 71, 51-56.
66. Liu, G.; Jia, M.; Zhou, Z.; Wang, L.; Zhang, W.; Jiang, D. Synthesis and pore formation study of amorphous mesoporous aluminophosphates in the presence of citric acid. J. Colloid Interface Sci. 2006, 302, 278-286.
67. Campelo, J.M.; Jaraba, M.; Luna, D.; Luque, R.; Marinas, J.M.; Romero, A.A. The effect of phosphate precursor and organic additives on the structural and catalytic properties of amorphous mesoporous AlPO4 materials. Chem. Mater. 2003, 15, 3352-3364.
68. Rodrigues, R.C.; Pessela, B.C.C.; Volpato, G.; Fernandez-Lafuente, R.; Guisan, J.M.; Ayub, M.A.Z. Two step ethanolysis: A simple and efficient way to improve the enzymatic biodiesel synthesis catalyzed by an immobilized-stabilized lipase from Thermomyces lanuginosus. Process Biochem. 2010, 45, 1268-1273.
69. Yesiloglu, Y. Immobilized lipase-catalyzed ethanolysis of sunflower oil. J. Am. Oil Chem. Soc. 2004, 81, 157-160.
70. Stamenković, O.S.; Veličković, A.V.; Veljković, V.B. The production of biodiesel from vegetable oils by ethanolysis: Current state and perspectives. Fuel 2011, 90, 3141-3155.
71. Bornscheuer, U.T. Lipase-catalyzed syntheses of monoacylglycerols. Enzym. Microb. Technol. 1995, 17, 578-586.
72. Li, W.; Du, W.; Liu, D. Rhizopus oryzae whole-cell-catalyzed biodiesel production from oleic acid in tert-butanol medium. Energy Fuels 2008, 22, 155-158.
73. Tüter, M.; Babali, B.; Köse, Ö.; Dural S.; Aksoy, H.A. 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. 1999, 21, 245-248.
74. Rathore, V.; Madras, G. Synthesis of biodiesel from edible and non-edible oils in supercritical alcohols and enzymatic synthesis in supercritical carbon dioxide. Fuel 2007, 8, 2650-2659.
75. Hernández-Martín, E.; Otero, C. Different enzyme requirements for the synthesis of biodiesel: Novozym-435 and Lipozyme TL IM. Bioresour. Technol. 2008, 99, 277-286.
76. Graebin, N.G.; Martins, A.B.; Lorenzoni, A.S.G.; Garcia-Galan, C.; Fernandez-Lafuente, R.; Ayub, M.A.Z.; Rodrigues, R.C. Immobilization o flipase B from Candida Antarctica on porous styrene-divinylbenzene beads improves butyl acetate synthesis. Biotechnol. Prog. 2012, 28, 406-412.
77. Rekondo, A.; Irusta, L.; Fernandez-Berridi, M.J. Characterization of silanized poly(ether-urethane) hybrid systems using thermogravimetric analysis (TG). J. Therm. Anal. Calorim. 2010, 101, 331-337.
78. Fukushima, H.; Kohri, M.; Kojima, T.; Taniguchi, T.; Saito, K.; Nakahira, T. Surface-initiated enzymatic vinyl polymerization: Synthesis of polymer-grafted silica particles using horseradish peroxidase as catalyst. Polym. Chem. 2012, 3, 1123-1125.
79. Galvin, C.J.; Genzer, I. Applications of surface-grafted macromolecules derived from post-polymerization modification reactions. Prog. Polym. Sci. 2012, 37, 871-906.
80. David, A.E.; Wang, N.S.; Yang, V.C.; Yang, A.J. Chemically surface modified gel (CSMG): An excellent enzyme-immobilization matrix for industrial processes J. Biotechnol. 2006, 125, 395-407.