Abstract
This study investigated the glycerolysis of babassu oil by Burkholderia cepacia lipase immobilized on SiO2–PVA particles in a continuous packed bed reactor. Experiments were conducted in a solvent-free system at 273.15 K either in an inert atmosphere or in the presence of cocoa butter to prevent lipid oxidation. The reactor (15 × 55 mm) was run at a fixed space time of 9.8 h using different molar ratios of babassu oil to glycerol (1:3, 1:6, 1:9, 1:12, and 1:15) to assess the effects of reactant molar ratio on monoacylglycerol productivity and selectivity. Nitrogen atmosphere and cocoa butter were equally effective in inhibiting lipid oxidation, indicating that addition of cocoa butter to glycerolysis reactions may be an interesting cost-reduction strategy. An oil/glycerol molar ratio of 1:9 resulted in the highest productivity (52.3 ± 2.9 mg g−1 h−1) and selectivity (31.5 ± 1.8%). Residence time distribution data were fitted to an axial dispersion model for closed-vessel boundary conditions, giving a mass transfer coefficient (kc) of 3.4229 × 10−6 m s−1. A kinetic model based on elementary steps of the studied reaction was written in Scilab and compared with experimental data, providing standard deviations in the range of 5.5–7.5%.
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References
Palacios D, Ortega N, Rubio-Rodríguez N, Busto MD (2019) Lipase-catalyzed glycerolysis of anchovy oil in a solvent-free system: simultaneous optimization of monoacylglycerol synthesis and end-product oxidative stability. Food Chem 271:372–379
Choi JM, Han SS, Kim HS (2015) Industrial applications of enzyme biocatalysis: current status and future aspects. Biotechnol Adv 33(7):1443–1454
Palomo JM, Filice M (2015) New emerging bio-catalysts design in biotransformations. Biotechnol Adv 33(5):605–613
Sánchez DA, Tonetto GM, Ferreira ML (2018) Burkholderia cepacia lipase: a versatile catalyst in synthesis reactions. Biotechnol Bioeng 115(1):6–24
Barriuso J, Vaquero ME, Prieto A, Martínez MJ (2016) Structural traits and catalytic versatility of the lipases from the Candida rugosa-like family: a review. Biotechnol Adv 34(5):874–885
Anobom CD, Pinheiro AS, De-Andrade RA, Aguieiras EC, Andrade GC, Moura MV, Freire DM (2014) From structure to catalysis: recent developments in the biotechnological applications of lipases. Biomed Res Int . https://doi.org/10.1155/2014/684506
Birolli WG, Ferreira IM, Alvarenga N, Santos DDA, de Matos IL, Comasseto JV, Porto AL (2015) Biocatalysis and biotransformation in Brazil: an overview. Biotechnol Adv 33(5):481–510
Daiha KDG, Angeli R, de Oliveira SD, Almeida RV (2015) Are lipases still important biocatalysts? A study of scientific publications and patents for technological forecasting. PLoS ONE 10(6):e0131624
Boas RNV, Ceron AA, Bento HB, de Castro HF (2018) Application of an immobilized Rhizopus oryzae lipase to batch and continuous ester synthesis with a mixture of a lauric acid and fusel oil. Biomass Bioenerg 119:61–68
Teixeira LF, Bôas RV, Oliveira PC, de Castro HF (2014) Effect of natural antioxidants on the lipase activity in the course of batch and continuous glycerolysis of babassu oil. Bioprocess Biosyst Eng 37(9):1717–1725
Solaesa ÁG, Sanz MT, Falkeborg M, Beltrán S, Guo Z (2016) Production and concentration of monoacylglycerols rich in omega-3 polyunsaturated fatty acids by enzymatic glycerolysis and molecular distillation. Food Chem 190:960–967
Christopher LP, Kumar H, Zambare VP (2014) Enzymatic biodiesel: challenges and opportunities. Appl Energy 119:497–520
Xia Q, Akanbi TO, Li R, Wang B, Yang W, Barrow CJ (2019) Lipase-catalysed synthesis of palm oil-omega-3 structured lipids. Food Funct 10(6):3142–3149
Singh AK, Mukhopadhyay M (2016) Enzymatic synthesis of mono-and diglyceride using lipase from candida rugosa immobilized onto cellulose acetate-coated Fe2O3 nanoparticles. Arab J Sci Eng 41(7):2553–2561
He Y, Li J, Kodali S, Chen B, Guo Z (2016) The near-ideal catalytic property of Candida antarctica lipase A to highly concentrate n-3 polyunsaturated fatty acids in monoacylglycerols via one-step ethanolysis of triacylglycerols. Bioresour Technol 219:466–478
Rarokar NR, Menghani S, Kerzare D, Khedekar PB (2017) Progress in synthesis of monoglycerides for use in food and pharmaceuticals. J Exp Food Chem 3:1–6
Liu W, Yang S, Gang H, Mu B, Liu J (2019) Efficient emulsifying properties of monoglycerides synthesized via simple and green route. J Dispers Sci Technol 41:1–9
Hu DJ, Chen JM, Xia YM (2013) A comparative study on production of middle chain diacylglycerol through enzymatic esterification and glycerolysis. J Ind Eng Chem 19(5):1457–1463
De Freitas L, Dos Santos JC, Zanin GM, De Castro HF (2010) Packed-bed reactor running on babassu oil and glycerol to produce monoglycerides by enzymatic route using immobilized Burkholderia cepacia lipase. Appl Biochem Biotechnol 161(1):372–381
Zeng FK, Yang B, Wang YH, Wang WF, Ning ZX, Li L (2010) Enzymatic production of monoacylglycerols with camellia oil by the glycerolysis reaction. J Am Oil Chem Soc 87(5):531–537
Kirana S, Arshada Z, Nosheenb S, Kamala S, Gulzara T, Majeeda MS, Rafiquec MA (2016) Microbial lipases: production and applications: a review. J Biochem Biotechnol Biomater 1(2):7–20
Aguedo M, Giet JM, Hanon E, Lognay G, Wathelet B, Destain J, Brasseur R, Vandenbol M, Danthine S, Blecker C, Wathelet JP (2009) Calorimetric study of milk fat/rapeseed oil blends and their interesterification products. Eur J Lipid Sci Tech 111(4):376–385
Saeed R, Naz S (2019) Effect of heating on the oxidative stability of corn oil and soybean oil. Grasas Aceites 70(2):303
Ramiro-Puig E, Castell M (2009) Cocoa: antioxidant and immunomodulator. Br J Nutr 101(7):931–940
Choong TSY, Yeoh CM, Phuah ET, Siew WL, Lee YY, Tang TK, Abdullah LC (2018) Kinetic study of lipase-catalyzed glycerolysis of palm olein using lipozyme TLIM in solvent-free system. PLoS ONE 13:e0192375
Voll F, Kruger RL, De Castilhos F, Filho LC, Cabral V, Ninow J, Corazza ML (2011) Kinetic modeling of lipase-catalyzed glycerolysis of olive oil. Biochem Eng J 56:107–115
Moquin PHL, Temelli F, King JW, Palcic MM (2005) Kinetic modeling of the glycerolysis reaction for soybean oils in supercritical carbon dioxide media. J Am Oil Chem Soc 82:613–617
Valério A, Krüger RL, Ninow J, Corazza FC, De Oliveira D, Vladimir Oliveira J, Corazza ML (2009) Kinetics of solvent-free lipase-catalyzed glycerolysis of olive oil in surfactant system. J Agric Food Chem 57:8350–8356
Suarez PA, Santos AL, Rodrigues JP, Alves MB (2009) Biocombustíveis a partir de óleos e gorduras: desafios tecnológicos para viabilizá-los. Quím Nova 32(3):768–775
Freitas L, Da Ros PC, Santos JC, De Castro HF (2009) An integrated approach to produce biodiesel and monoglycerides by enzymatic interestification of babassu oil (Orbinya sp.). Process Biochem 44(10):1068–1074
Da Rós PC, Silva GA, Mendes AA, Santos JC, De Castro HF (2010) Evaluation of the catalytic properties of Burkholderia cepacia lipase immobilized on non-commercial matrices to be used in biodiesel synthesis from different feedstocks. Bioresour Technol 101(14):5508–5516
Cheirsilp B, Kaewthong W, Aran H (2007) Kinetic study of glycerolysis of palm olein for monoacylglycerol production by immobilized lipase. Biochem Eng J 35(1):71–80
Noureddini H, Harkey DW, Gutsman MR (2004) A continuous process for the glycerolysis of soybean oil. J Am Oil Chem Soc 81:203–207
Martin LS, Ceron A, Oliveira PC, Zanin GM, De Castro HF (2018) Different organic components on silica hybrid matrices modulate the lipase inhibition by the glycerol formed in continuous transesterification reactions. J Ind Eng Chem 62:462–470
Levenspiel O (2000) Engenharia das reações químicas, São Paulo: Edgard Blucher. Cap 5:74–98
AOCS (2004) Official methods and recommended practices of the American Oil Chemists’ Society. AOCS, Champaign
Fogler HS (2016) Elementos de Engenharia das Reações Químicas, 5th edn. LTC, Rio de Janeiro
Al-Muftah AE, Abu-Reesh IM (2005) Effects of simultaneous internal and external mass transfer and product inhibition on immobilized enzyme-catalyzed reactor. Biochem Eng J 27:167–178
Wilke CR, Chang P (1955) Correlation of diffusion coefficients in dilute solutions. AIChe J 1(2):264–270
Treybal RE (1980) Mass-transfer operations. McGraw-Hill, New York, p 784
Santana JL, Oliveira JMD, Carvalho NB, Osório NMFDM, Mattedi S, Freitas LDS, Soares CMF (2018) Analysis of the performance of a packed bed reactor to production ethyl esters from crude vegetable oil using lipase immobilized in silica modified with protic ionic liquid. Quím Nova 41(8):891–898
Seguin D, Montillet A, Brunjail D, Comiti J (1996) Liquid–solid mass transfer in packed beds of variously shaped particles at low Reynolds numbers: experiments and model. Chem Eng J Biochem Eng J 63(1):1–9
Fogler HS (2016) Elements of chemical reaction engineering, 5th edn, New Jersey, USA
Stauch B, Fisher SJ, Cianci M (2015) Open and closed states of Candida antarctica lipase B: protonation and the mechanism of interfacial activation. J Lipid Res 56(12):2348–2358
Kruger RL, Sychoski M, Balen M, Ninow JL, Corazza ML (2011) Estudo da glicerólise enzimática na produção de mono e diacilgliceróis utilizando óleo de oliva. Rev Ciênc Exatas Nat 13(3):331–351
Choong TSY, Yeoh CM, Phuah ET, Siew WL, Lee YY, Tang TK, Chuah Abdullah L (2018) Kinetic study of lipase-catalyzed glycerolysis of palm olein using Lipozyme TLIM in solvent-free system. PLoS ONE 13(2):e0192375
Van Der Laan ET (1958) Chem Eng Sci 7:187
Simões A, Ramos L, Freitas L, Santos JC, Zanin GM, De Castro HF (2015) Performance of an enzymatic packed bed reactor running on babassu oil to yield fatty ethyl esters (FAEE) in a solvent-free system. Biofuel Res J 2(2):242
Gorfferjé G, Stäbler A, Herfellner T, Schweiggert-Weisz U, Flöter E (2014) Kinetics of enzymatic esterification of glycerol and free fatty acids in crude Jatropha oil by immobilized lipase from Rhizomucor miehei. J Mol Catal B Enzym 107:1–7
Cristancho DM, Delgado DR, Martínez F, Abolghassemi Fakhree MA, Jouyban A (2011) Volumetric properties of glycerol + water mixtures at several temperatures and correlation with the Jouyban-Acree model. Rev Colomb Cienc Quim Farm 40(1):92–115
Acknowledgements
This study was supported by the São Paulo State Research Foundation (FAPESP, grant nos. 2016/17833-3 and 2016/10636-8), the Brazilian National Council for Scientific and Technological Development (CNPq, process no. 433248/2018-1), and the Brazilian Federal Agency for Support and Evaluation of Graduate Education (CAPES, Finance Code 001).
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Vilas Bôas, R.N., Lima, R., Silva, M.V.C. et al. Continuous production of monoacylglycerol via glycerolysis of babassu oil by immobilized Burkholderia cepacia lipase in a packed bed reactor. Bioprocess Biosyst Eng 44, 2205–2215 (2021). https://doi.org/10.1007/s00449-021-02596-6
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DOI: https://doi.org/10.1007/s00449-021-02596-6