Biofuel Research Journal

Biofuel Research Journal

Lipase immobilized on polydopamine-coated magnetite nanoparticles for biodiesel production from soybean oil

Document Type : Research Paper

Authors
Marcos F. C. Andrade
Andre L. A. Parussulo
Caterina G. C. M. Netto
Leandro H. Andrade
Henrique E. Toma
Instituto de Química, Universidade de São Paulo, 05508-000, São Paulo, Brazil
10.18331/BRJ2016.3.2.5
Abstract
Lipase from Pseudomonas cepacia was covalently attached to magnetite nanoparticles coated with a thin polydopamine film, and employed in the enzymatic conversion of soybean oil into biodiesel, in the presence of methanol.  The proposed strategy explored the direct immobilization of the enzyme via Michael addition and aldolic condensation reactions at the catechol rings, with no need of using specific coupling agents. In addition, a larger amount of enzymes could be bound to the magnetic nanoparticles, allowing their efficient recycling with the use of an external magnet. In the biodiesel conversion, the transesterification reaction was carried out directly in soybean oil by the stepwise addition of methanol, in order to circumvent its inactivation effect on the enzyme. A better yield was  obtained in relation to the free enzyme, achieving 90% yield at 37 oC.  However, the catalysis became  gradually less effective after the third cycle, due to its prolonged exposition to the denaturating methanol medium.

Graphical Abstract

Lipase immobilized on polydopamine-coated magnetite nanoparticles for biodiesel production from soybean oil

Highlights

  • Lipase attached to polydopamine magnetite nanoparticle converted soybean oil into biodiesel with high efficiency.

  • The polydopamine film allowed direct binding of the enzyme.

  • Polydopamine also promoted immobilization of a large amount of enzymes onto the magnetic nanoparticles.

  • The enzyme could be magnetically recycled.

Keywords
Biodiesel
Soybean oil
Lipase
Immobilization
Magnetic nanoparticles
polydopamine
[1] Atabani, A.E., Silitong, A.S., Badruddin, I.A., Mahlia, T.M.I., Masjuki, H.H., Mekhilef, S.A., 2012. Comprehensive review on biodiesel as an alternative energy source and its characteristics. Renew. Sust. Energy Rev. 16, 2070-2093.
[2] Bisen, P.S., Sanodiya, B.S., Thakur, G.S., Baghed, R.K., Prasad, G.B., 2010. Biodiesel production with special emphasis on lipase-catalised transesterification. Biotechnol. Lett. 32, 1019-1030.
[3] Black, K.C., Yi, J., Rivera, J.G., Zelasko-Leon, D.C., Messersmith, P.B., 2013. Polydopamine-enabled surface functionalization of gold nanorods for cancer cell-targeted imaging and phothermal therapy. Nanomedicine. 8, 17-28.
[4] Bose, S., Armstrong, D.W., Petrich, J.W., 2010. Enzyme-catalyzed hydrolysis of cellulose in ionic liquids: a green approach toward the production of biofuels. J. Phys. Chem. B. 114, 8221-8227.
[5] Dumri, K., Hung-Anh, D., 2014. Immobilization of lipase on silver nanoparticles via adhesive polydopamine for biodiesel production. Enzyme Res. Article ID 389739.
[6] Garcia-Galan, C., Berenguer-Murcia, A., Fernandez-Lafuente, R., Rodrigues, R.C., 2011. Potential of different enzyme immobilization strategies to improve enzyme performance. Adv. Synth. Catal. 353, 2885-2904.
[7] Hama, S., Yamaji, H., Fukumizu, T., Numata, T., Tamalampudi, S., Kondo, A., Noda, H., Fukuda, H., 2007. Biodiesel-fuel production in a packed-bed reactor using lipase-producing Rhizopus oryzae cells immobilized within biomass support particles. Biochem Eng. J. 34, 273-278.
[8] Hanefeld, U., Gardossi, L., Magner, E., 2009. Understanding enzyme immobilization. Chem. Soc. Rev. 38, 453-468.
[9] Katchalski-Katzir, E., 1993. Immobilized enzymes learning from past successes and failures. Trends Biotechnol. 11, 471-478.
[10] Kim, J., Jia, J., Wang, P., 2006. Challenges in biocatalysis for enzyme based biofuel cells. Biotechnol. Adv. 24, 296-308.
[11] Lee, H., Dellatore, S.M., Miller, W.M., Messersmith, P.B., 2007. Mussel inspired surface chemistry for multifunctional coatings. Science. 318, 426-430.
[12] Lee, H., Rho, J., Messersmith, P.B., 2009. Facile conjugation of biomolecules onto surfaces via mussel adhesive protein inspired coatings.  Adv. Mat. 21, 431-434.
[13] Liebscher, J., Mrowczynski, R., Scheidt, H.A., Filip, C., Hadade, N.D., Turcu, R., Bende, A., 2013. Structure of polydopamine: a never-ending story?. Langmuir.  29, 10539-10548.
[14] Li, S.F., Fan, Y.H., Hu, R.F., Wu, W.T., 2011. Pseudomonas cepacia lipase immobilized onto the electrospun pan nanofibrous membranes for biodiesel production from soybean oil. J. Mol. Catal. B: Enzym. 72, 40-45.
[15] Mahamuni, N.N., Adewuyi, Y.G., 2009. Fourier transform infrared spectroscopy (FTIR) method to monitor soy biodiesel and soybean oil in transesterification reactions, petrodiesel-biodiesel blends and blend adulteration with soy oil. Energy Fuels. 23, 3773-3782.
[16] Mateo, C., Palomo, J.M., Fernandes-Lorente, G., Guisan, J.M., Fernanes-Lafuente, R., 2007. Improvement of enzyme activity, stability and selectivity via immobilization techniques. Enzyme Microb. Tech. 40, 1451-1463.
[17] Moser, B.R., 2011. Biodiesel production, properties, and feedstocks, in: Tomes, D., Lakshmanan, P., Sonstad, D. (Eds.), Biofuels. New York, Springer, pp. 285-347.
[18] Netto, C.G.C.M., Andrade, L.H., Toma, H.E., 2009. Enantioselective transesterification catalysis by Candida antarctica lipase immobilized on superparamagnetic nanoparticles. Tetrahedron: Asymmetry. 20, 2299-2304.
[19] Netto, C.G.C.M., Nakamatsu, E.H., Netto, L.E.S., Novak, M.A., Zuin, A., Nakamura, M., Araki, K., Toma, H.E., 2011. Catalytic properties of thioredoxin immobilized on superparamagnetic nanoparticles. J. Inorg. Biochem. 105, 738-744.
[20] Netto, C.G.C.M., Nakamura, M., Andrade, L.H., Toma, H. E., 2012. Improving the catalytic activity of formate dehydrogenase from Candida boidinii by using magnetic nanoparticles. J. Mol. Catal. B: Enzym. 84, 139-143.
[21] Netto, C.G.C.M., Toma, H.E., Andrade, L.H., 2013. Superparamagnetic nanoparticles as versatile and supporting materials for enzymes. J. Mol. Catal. B: Enzym. 85-86, 71-92.
[22] Netto, C.G.C.M., Andrade, L.H., Toma, H.E., 2015. Association of Pseudomonas putida formaldehyde dehydrogenase with superparamagnetic nanoparticles: an effective way of improving the enzyme stability, performance and recycling. New J. Chem. 39, 2162-2167.
[23] Rebelo, L.P., Netto, C.G., Toma, H.E., Andrade, L.H., 2010. Enzymatic kinetic resolution of (rs)-1-(phenyl)ethanols by Burkholderia cepacia lipase immobilized on magnetic nanoparticles. J. Braz. Chem. Soc. 21, 1537-1542.
[24] Ren, Y., Rivera, J.G., He, L., Kulkarni, H., Lee, D.K., Messersmith, P.D., 2011. Facile, high efficiency immobilization of lipase enzyme on magnetic iron oxide nanoparticles via a biomimetic coating. BMC Biotech. 11, 63. DOI: 10.1186/1472-6750-11-63.
[25] Rodrigues, R.C., Ortiz, C., Berenguer-Murcia, A., Torres, R., Fernandez-Lafuente, R., 2013. Modifying enzyme activity and selectivity by immobilization. Chem. Soc. Rev. 42, 6290-6307.
[26] Sharp, C.A., Howell, S.A., Jobe, J., 2000. The effect of biodiesel fuels on transient emissions from modern diesel engines, Part II, unregulated emissions and chemical characterization. SAE Technical Paper. No. 2000-01-1968.
[27] Srivastava, A., Prasad, A.R., 2000. Triglycerides-based diesel fuels. Renew. Sust. Energy Rev. 4, 111-133.
[28] Straathof, A.J., Panke, S., Schmid, A., 2002.  The production of fine chemicals by biotransformations. Curr. Opin. Biotechnol. 13, 548-556.
[29] Tan, T., Lu, J.K., Nie, K.L., Deng, L., Wang, F., 2010. Biodiesel production with immobilised lipase: a review.  Biotechnol. Adv. 26, 628-634.  
[30] Verma, M.L., Barrow, C.J., Puri, M., 2013. Nanobiotechnology as a novel paradigm for enzyme immobilisation and stabilisation with potential applications in biodiesel production. Appl. Microbiol. Biotechnol. 97, 23-39.
[31] Wang, X., Liu, X., Zhao, C., Ding, Y., Xu, P., 2011. Biodiesel production in packed-bed reactors using lipase-nanoparticle biocomposite.  Bioresour. Technol. 102, 6352-6355.
[32] Xu, C., Xu, K., Gu, H., Zheng, R., Liu, H., Zhang, X., Guo, Z., Xu, B., 2004. Dopamine as a robust anchor to immobilize functional molecules on the iron oxide shell of magnetic nanoparticles. J. Am. Chem. Soc. 126, 9938-9939.
[33] Yamaura, M., Camilo, R.L., Sampaio, L.C., Macedo, M.A., Nakamura, M., Toma, H.E., 2004.  Preparation and characterization of (3-aminopropyl) triethoxysilane coated magnetite nanoparticles. J. Magn. Magn. Mater. 279, 210-217.
[34] Yücel, Y., Demir, C., Dizge, N., Keskinler, B., 2011. Lipase immobilization and production of fatty acid methyl esters from canola oil using immobilized lipase. Biomass Bioenergy. 35, 1496-1501.
[35] Zhang, F., Adachi, D., Tamalampudi, S., Kondo, A., Tominaga, K., 2013.  Real-time monitoring of the transesterification of soybean oil and methanol by fourier transform infrared spectroscopy. Energy Fuels. 27, 5957-5961.
Biofuel Research Journal
Volume 3, Issue 2 - Serial Number 2
Spring 2016
Pages 403-409