Abstract
In the present work, magnetic nanoparticles (MNPs) were prepared by chemical precipitation of trivalent and divalent iron ions which were functionalized using citric acid. The bacterial isolate Staphylococcus epidermidis KX781317 was isolated from oil-contaminated site. The isolate produced lipase, which was purified and immobilized on magnetic nanoparticles (MNPs) for ester synthesis from waste frying oil (WFO). The characterization of MNPs employed conventional TEM, XRD and FTIR techniques. TEM analysis of MNPs showed the particle size in the range of 20–50 nm. FTIR spectra revealed the binding of citric acid to Fe3O4 and lipase on citric acid-coated MNPs. The citric acid-coated MNPs and lipase-conjugated citric acid-coated MNPs had similar XRD patterns which indicate MNPs could preserve their magnetic properties. The maximum immobilization efficiency 98.21% of lipase-containing citric acid-coated MNPs was observed at ratio 10:1 of Cit-MNPs:lipase. The pH and temperature optima for lipase conjugated with Cit-MNPs were 7 and 35 °C, respectively. Isobutanol was found to be an effective solvent for ester synthesis and 1:2 ratio of oil:alcohol observed significant for ester formation. The ester formation was determined using TLC and the % yield of ester conversion was calculated. The rate of ester formation is directly proportional to the enzyme load. Formed esters were identified as isobutyl laurate ester and isobutyl myristate ester through GC–MS analysis.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Alex D, Mathew A, Sukumaran RK (2014) Esterases immobilized on aminosilane modified magnetic nanoparticles as a catalyst for biotransformation reactions. Bioresour Technol 167:547–550. https://doi.org/10.1016/j.biortech.2014.05.110
Bezbradica D, Mijin D, Siler-Marinkovic S, Knezevic Z (2006) The Candida rugosa lipase catalyzed synthesis of amyl isobutyrate in organic solvent and solvent-free system: a kinetic study. J Mol Catal B Enzym 38:11–16. https://doi.org/10.1016/j.molcatb.2005.10.004
Cadirci BH, Yasa I (2010) An organic solvents tolerant and thermotolerant lipase from Pseudomonas fluorescens P21. J Mol Catal B Enzym 64(3–4):155–161. https://doi.org/10.1016/j.molcatb.2009.09.009
Cesarini S, Pastor F, Nielsen P, Diaz P (2015) Moving towards a competitive fully enzymatic biodiesel process. Sustainability 7:7884–7903. https://doi.org/10.3390/su7067884
Chen YZ, Ching CB, Xu R (2009) Lipase immobilization on modified zirconia nanoparticles: studies on the effects of modifiers. Process Biochem 44:1245–1251. https://doi.org/10.1016/j.procbio.2009.06.023
De Lima LN, Vieira GNA, Kopp W et al (2016) Mono- and heterofunctionalized silica magnetic microparticles (SMMPs) as new carriers for immobilization of lipases. J Mol Catal B Enzym. https://doi.org/10.1016/j.molcatb.2017.04.002
Dizge N, Aydiner C, Imer DY et al (2009) Biodiesel production from sunflower, soybean, and waste cooking oils by transesterification using lipase immobilized onto a novel microporous polymer. Bioresour Technol 100:1983–1991. https://doi.org/10.1016/j.biortech.2008.10.008
Eggert T, Pencreac HG, Douchet I et al (2000) A novel extracellular esterase from Bacillus subtilis and its conversion to a monoacylglycerol hydrolase. Eur J Biochem 267:6459–6469. https://doi.org/10.1046/j.1432-1327.2000.01736.x
Florian TN (2015) Iron oxide nanoparticles with citric acid coating: properties and studies on experimental models. University of Medicine and Pharmacy of Craiova Doctoral School, PhD Thesis Summary
Ghamgui H, Karra-Chaâbouni M, Gargouri Y (2004) 1-Butyl oleate synthesis by immobilized lipase from Rhizopus oryzae: a comparative study between n-hexane and solvent-free system. Enzyme Microb Technol 35:355–363. https://doi.org/10.1016/j.enzmictec.2004.06.002
Guan F, Peng P, Wang G et al (2010) Combination of two lipases more efficiently catalyzes methanolysis of soybean oil for biodiesel production in aqueous medium. Process Biochem 45:1677–1682. https://doi.org/10.1016/j.procbio.2010.06.021
Halim SFA, Kamaruddin AH, Fernando WJN (2009) Continuous biosynthesis of biodiesel from waste cooking palm oil in a packed bed reactor: optimization using response surface methodology (RSM) and mass transfer studies. Bioresour Technol 100:710–716. https://doi.org/10.1016/j.biortech.2008.07.031
Huang SH, Liao MH, Chen DH (2003) Direct binding and characterization of lipase onto magnetic nanoparticles. Biotechnol Prog 19:1095–1100. https://doi.org/10.1021/bp025587v
Jafari A, Salouti M, Shayesteh SF et al (2015) Synthesis and characterization of Bombesin-superparamagnetic iron oxide nanoparticles as a targeted contrast agent for imaging of breast cancer using MRI. Nanotechnology 26:075101. https://doi.org/10.1088/0957-4484/26/7/075101
Joseph B, Ramteke PW, Thomas G (2008) Cold active microbial lipases: some hot issues and recent developments. Biotechnol Adv 26:457–470. https://doi.org/10.1016/j.biotechadv.2008.05.003
Karmee S, Patria R, Lin C (2015) Techno-economic evaluation of biodiesel production from waste cooking oil—a case study of Hong Kong. Int J Mol Sci 16:4362–4371. https://doi.org/10.3390/ijms16034362
Kumar D, Nagar S, Bhushan I et al (2013) Covalent immobilization of organic solvent tolerant lipase on aluminum oxide pellets and its potential application in esterification reaction. J Mol Catal B Enzym 87:51–61. https://doi.org/10.1016/j.molcatb.2012.10.002
Lettera V, Pezzella C, Cicatiello P et al (2015) Efficient immobilization of a fungal laccase and its exploitation in fruit juice clarification. Food Chem 196:1272–1278. https://doi.org/10.1016/j.foodchem.2015.10.074
Liu Y, Jia S, Wu Q et al (2011) Studies of Fe3O4-chitosan nanoparticles prepared by co-precipitation under the magnetic field for lipase immobilization. Catal Commun 12:717–720. https://doi.org/10.1016/j.catcom.2010.12.032
Lowry OH, Rosebrough NJ, Farr AL, Randall RJ (1951) Protein measurement with the Folin phenol reagent. J Biol Chem 193:265–275. https://doi.org/10.1016/0304-3894(92)87011-4
Lu AH, Salabas EL, Schüth F (2007) Magnetic nanoparticles: synthesis, protection, functionalization, and application. Angew Chemie Int Ed 46:1222–1244. https://doi.org/10.1002/anie.200602866
Mander P, Yoo HY, Kim SW et al (2014) Transesterification of waste cooking oil by an organic solvent-tolerant alkaline lipase from Streptomyces sp. CS273. Appl Biochem Biotechnol 172:1377–1389. https://doi.org/10.1007/s12010-013-0610-7
Mehrasbi MR, Mohammadi J, Peyda M, Mohammadi M (2017) Covalent immobilization of Candida antarctica lipase on core-shell magnetic nanoparticles for production of biodiesel from waste cooking oil. Renew Energy 101:593–602. https://doi.org/10.1016/j.renene.2016.09.022
Neta NDAS, Dos Santos JCS, Sancho SDO et al (2012) Enzymatic synthesis of sugar esters and their potential as surface-active stabilizers of coconut milk emulsions. Food Hydrocoll 27:324–331. https://doi.org/10.1016/j.foodhyd.2011.10.009
Ozyilmaz G, Gezer E (2010) Production of aroma esters by immobilized Candida rugosa and porcine pancreatic lipase into calcium alginate gel. J Mol Catal B Enzym 64:140–145. https://doi.org/10.1016/j.molcatb.2009.04.013
Panadare DC, Rathod VK (2015) Applications of waste cooking oil other than biodiesel: a review. Iran J Chem Eng 12:55–76
Qi H, Du Y, Hu G, Zhang L (2017) Poly(carboxybetaine methacrylate)-functionalized magnetic composite particles: a biofriendly support for lipase immobilization. Int J Biol Macromol. https://doi.org/10.1016/j.ijbiomac.2017.10.150
Racuciu M, Creanga DE, Airinei A (2006) Citric-acid-coated magnetite nanoparticles for biological applications. Eur Phys J E 21:117–121. https://doi.org/10.1140/epje/i2006-10051-y
Ren Y, Rivera JG, He L et al (2011) Facile, high efficiency immobilization of lipase enzyme on magnetic iron oxide nanoparticles via a biomimetic coating. BMC Biotechnol 11:63. https://doi.org/10.1186/1472-6750-11-63
Romero CM, Pera LM, Loto F et al (2012) Purification of an organic solvent-tolerant lipase from Aspergillus niger MYA 135 and its application in ester synthesis. Biocatal Agric Biotechnol 1:25–31. https://doi.org/10.1016/j.bcab.2011.08.013
Sharma S, Kanwar SS (2014) Organic solvent tolerant lipases and applications. Sci World J 2014:1–15
Singh D, Gautam RK, Kumar R et al (2014) Citric acid-coated magnetic nanoparticles: synthesis, characterization and application in removal of Cd(II) ions from aqueous solution. J Water Process Eng 4:233–241. https://doi.org/10.1016/j.jwpe.2014.10.005
Sui Y, Cui Y, Nie Y et al (2012) Surface modification of magnetite nanoparticles using gluconic acid and their application in immobilized lipase. Colloids Surf B Biointerf 93:24–28. https://doi.org/10.1016/j.colsurfb.2011.11.054
Thangaraj B, Jia Z, Dai L et al (2016) Lipase NS81006 immobilized on Fe3O4 magnetic nanoparticles for biodiesel production. Ovidius Univ Ann Chem 27:13–21. https://doi.org/10.1016/j.arabjc.2016.09.004
Ugur A, Sarac N, Boran R et al (2014) New lipase for biodiesel production: partial purification and characterization of LipSB 25-4. ISRN Biochem 2014:1–7. https://doi.org/10.1155/2014/289749
Wang X, Dou P, Zhao P et al (2009) Immobilization of lipases onto magnetic Fe3O4 nanoparticles for application in biodiesel production. Chemsuschem 2:947–950. https://doi.org/10.1002/cssc.200900174
Wang Y, Xia L, Xu X et al (2012) Lipase-catalyzed acidolysis of canola oil with caprylic acid to produce medium-, long- and medium-chain-type structured lipids. Food Bioprod Process 90:707–712. https://doi.org/10.1016/j.fbp.2012.02.003
Yamaura M, Camilo RL, Sampaio LC et al (2004) Preparation and characterization of (3-aminopropyl)triethoxysilane-coated magnetite nanoparticles. J Magn Magn Mater 279:210–217. https://doi.org/10.1016/j.jmmm.2004.01.094
Yu CY, Huang LY, Kuan IC, Lee SL (2013) Optimized production of biodiesel from waste cooking oil by lipase immobilized on magnetic nanoparticles. Int J Mol Sci 14:24074–24086. https://doi.org/10.3390/ijms141224074
Acknowledgements
The authors wish to acknowledge SICART, Vallabh Vidyanagar, Anand, Gujarat, for providing the necessary instrumentation facilities. This research did not receive any specific grant from funding agencies in the public, commercial or not for profit sectors.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors hereby want to declare that there is no conflict of interest whatsoever in this publication.
Rights and permissions
About this article
Cite this article
Patel, U., Chauhan, K. & Gupte, S. Synthesis, characterization and application of lipase-conjugated citric acid-coated magnetic nanoparticles for ester synthesis using waste frying oil. 3 Biotech 8, 211 (2018). https://doi.org/10.1007/s13205-018-1228-9
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s13205-018-1228-9