Abstract
This work aimed at the kinetic modeling of enzymatic reactions for the production of sugar fatty esters type biosurfactants. The production of biosurfactants by esterification (72 h, 250 rpm stirring and 1.5 g of molecular sieve) of oleic and lauric acids with fructose and lactose, in the presence of tert-butanol and 2-methyl-2-butanol, has already been evaluated experimentally using Candida antarctica lipase B immobilized (CALB-IM-T2-350) and Pseudomonas fluorescens lipase (PFL) immobilized on octyl-silica. Acid conversion against time assays were carried out changing the following parameters: acid:sugar molar ratio (1:1 and 1:2), sugar concentration (25 and 50 mM), temperature (45 and 55 °C) and mass of biocatalyst (0.25 and 0.5 g). The Ping Pong Bi Bi kinetic model was fitted to data selected from the above-cited assays, assuming the production of only monoesters (relating the consumption of sugar and acid by an equimolar relation). The values for Vmax, Ksugar and Kacid were estimated. When CALB-IM-T2-350 was used, at 55 °C, Vmax = 1133 ± 221 mmol/Lh, Ksugar = 1378 ± 1696 mmol/L and Kacid = 3298 ± 1015 mmol/L. In the syntheses with PFL-octyl-silica, the results indicated lower conversions, with Vmax varying between 124 ± 13 and 221 ± 34 mmol/Lh (depending on reaction conditions) and K = 10,241 ± 1526 mmol/L (in average). A very good fit of the proposed model to the experimental data was obtained. For validation purpose, a different set of experimental data was used. The validation concentration profile showed an excellent prediction capability of the model.
Similar content being viewed by others
References
Lima LN, Mendes AA, Fernandez-Lafuente R, Tardioli PW, de Camargo Giordano RL (2018) Performance of different immobilized lipases in the syntheses of short- and long-chain carboxylic acid esters by esterification reactions in organic media. Molecules 23(4):766
Vescovi V, Santos JBC, Tardioli PW (2017) Porcine pancreatic lipase hydrophobically adsorbed on octyl-silica: a robust biocatalyst for syntheses of xylose fatty acid esters. Biocatal Biotransform 35(4):298–305
Colla LM, Rizzardi J, Pinto MH, Reinehr CO, Bertolin TE, Costa JAV (2010) Simultaneous production of lipases and biosurfactants by submerged and solid-state bioprocesses. Bioresour Technol. https://doi.org/10.1016/j.biortech.2010.05.086
Khan NR, Rathod VK (2015) Enzyme catalyzed synthesis of cosmetic esters and its intensification: a review. Process Biochem. https://doi.org/10.1016/j.procbio.2015.07.014
Nitschke M, Pastore GM (2002) Biossurfactantes: propriedades e aplicações. Quim Nova 25(5):772–776
Pacwa-Płociniczak M, Płaza GA, Piotrowska-Seget Z, Cameotra SS (2011) Environmental applications of biosurfactants: recent advances. Int J Mol Sci 12(1):633–654
Sachdev DP, Cameotra SS (2013) Biosurfactants in agriculture. Appl Microbiol Biotechnol 97(3):1005–1016
Saharan BS, Sahu RK, Sharma D (2011) A review on biosurfactants: fermentation, applications, current. Genet Eng Biotechnol J 29:1–42
van den Broek LAM, Boeriu CG (2013) Enzymatic synthesis of oligo- and polysaccharide fatty acid esters. Carbohydr Polym. https://doi.org/10.1016/j.carbpol.2012.05.051
Mustafa A, Karmali A, Abdelmoez W (2016) Optimisation and economic assessment of lipase-catalysed production of monoesters using Rhizomucor miehei lipase in a solvent-free system. J Clean Prod. https://doi.org/10.1016/j.jclepro.2016.07.056
Nitschke M, Silva SS (2018) Recent food applications of microbial surfactants. Crit Rev Food Sci Nutr. https://doi.org/10.1080/10408398.2016.1208635
Silva ACB, Rodrigues MS, de Sousa JR, de Resende MM (2019) An experimental and computational study of biosurfactant production from soy molasses. React Kinet Mech Catal. https://doi.org/10.1007/s11144-019-01657-y
Costa SGVADO, Nitschke M, Contiero J (2008) Produção de biotensoativos a partir de resíduos de óleos e gorduras. Cienc e Tecnol Aliment 28(1):34–38
Liu G, Zhong H, Yang X, Liu Y, Shao B, Liu Z (2018) Advances in applications of rhamnolipids biosurfactant in environmental remediation: a review. Biotechnol Bioeng 115(4):796–814
Kennedy JF, Kumar H, Panesar PS, Marwaha SS, Goyal R, Parmar A, Kaur S (2006) Enzyme-catalyzed regioselective synthesis of sugar esters and related compounds. J Chem Technol Biotechnol 81(October):866–876
Gumel AM, Annuar MSM, Heidelberg T, Chisti Y (2011) Lipase mediated synthesis of sugar fatty acid esters. Process Biochem 46(11):2079–2090
An D, Zhang X, Liang F, Xian M, Feng D, Ye Z (2019) Synthesis, surface properties of glucosyl esters from renewable materials for use as biosurfactants. Colloids Surf A Physicochem Eng Asp. https://doi.org/10.1016/j.colsurfa.2019.05.079
Dang HT, Obiri O, Hayes DG (2005) Feed batch addition of saccharide during saccharide-fatty acid esterification catalyzed by immobilized lipase: time course, water activity, and kinetic model. JAOCS 82(7):487–493
Zaidan UH, Abdul Rahman MB, Othman SS, Basri M, Abdulmalek E, Rahman RNZRA, Salleh AB (2011) Kinetic behaviour of free lipase and mica-based immobilized lipase catalyzing the synthesis of sugar esters. Biosci Biotechnol Biochem. https://doi.org/10.1271/bbb.110117
Reis P, Miller R, Krägel J, Leser M, Fainerman V, Watzke H, Holmberg K (2008) Lipases at interfaces: unique interfacial properties as globular proteins. Langmuir 24(13):6812–6819
Thangaraj B, Solomon PR (2019) Immobilization of lipases—a review. Part I: enzyme immobilization. ChemBioEng Rev 6(5):157–166
Jaeger KE, Reetz MT (1998) Microbial lipases form versatile tools for biotechnology. Trends Biotechnol 16(9):396–403
Paiva AL, Balcao VM, Malcata FXX, Balcão VM, Malcata FXX (2000) Kinetics and mechanisms of reactions catalyzed by immobilized lipases. Enzym Microb Technol 27(3–5):187–204
Stergiou P-Y, Foukis A, Filippou M, Koukouritaki M, Parapouli M, Theodorou LG, Pandey A, Papamichael EM (2013) Advances in lipase-catalyzed esterification reactions. Biotechnol Adv 31:1846–1859
Cajal Y, Svendsen A, De Bolós J, Patkar SA, Alsina MA (2000) Effect of the lipid interface on the catalytic activity and spectroscopic properties of a fungal lipase. Biochimie 82(11):1053–1061
Kazlauskas RJ (1994) Elucidating structure-mechanism relationships in lipases: prospects for predicting and engineering catalytic properties. Trends Biotechnol 12(11):464–472
Hernandez K, Garcia-Galan C, Fernandez-Lafuente R (2011) Simple and efficient immobilization of lipase B from Candida antarctica on porous styrene-divinylbenzene beads. Enzym Microb Technol. https://doi.org/10.1016/j.enzmictec.2011.03.002
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 56:2348–2358
Dandekar PP, Patravale VB (2009) Enzymatic synthesis of fructose ester from Mango Kernel Fat. Indian J Chem Technol 16(4):317–321
Enayati M, Gong Y, Goddard JM, Abbaspourrad A (2018) Synthesis and characterization of lactose fatty acid ester biosurfactants using free and immobilized lipases in organic solvents. Food Chem. https://doi.org/10.1016/j.foodchem.2018.06.051
Li X, Hai YW, Ma D, Chen J, Banwell MG, Lan P (2019) Fatty acid ester surfactants derived from raffinose: synthesis, characterization and structure-property profiles. J Colloid Interface Sci 556:616–627
Marathe SJ, Shah NN, Singhal RS (2020) Enzymatic synthesis of fatty acid esters of trehalose: process optimization, characterization of the esters and evaluation of their bioactivities. Bioorg Chem. https://doi.org/10.1016/j.bioorg.2019.103460
do Neta NAS, dos Santos JCS, de Sancho SO, Rodrigues S, Gonçalves LRB, Rodrigues LR, Teixeira JA (2012) Enzymatic synthesis of sugar esters and their potential as surface-active stabilizers of coconut milk emulsions. Food Hydrocoll. https://doi.org/10.1016/j.foodhyd.2011.10.009
Nguyen PC, Nguyen MTT, Lee CK, Oh IN, Kim JH, Hong ST, Park JT (2019) Enzymatic synthesis and characterization of maltoheptaose-based sugar esters. Carbohydr Polym. https://doi.org/10.1016/j.carbpol.2019.04.079
Soultani S, Engasser JM, Ghoul M (2001) Effect of acyl donor chain length and sugar/acyl donor molar ratio on enzymatic synthesis of fatty acid fructose esters. J Mol Catal B Enzym 11(4–6):725–731
Li L, Ji F, Wang J, Jiang B, Li Y, Bao Y (2015) Efficient mono-acylation of fructose by lipase-catalyzed esterification in ionic liquid co-solvents. Carbohydr Res 416:51–58
Arcos JA, Hill CG, Otero C (2001) Kinetics of the lipase-catalyzed synthesis of glucose esters in acetone. Biotechnol Bioeng 73(2):104–110
Chávez-Flores L, Beltran H, Arrieta-Baez D, Reyes-Duarte D (2017) Regioselective synthesis of lactulose esters by Candida antarctica and Thermomyces lanuginosus lipases. Catalysts. https://doi.org/10.3390/catal7090263
Woudenberg-Van Oosterom M, Van Rantwijk F, Sheldon RA (1996) Regioselective acylation of disaccharides in tert-butyl alcohol catalyzed by Candida antarctica lipase. Biotechnol Bioeng 49(3):328–333
Nelles O (2001) Nonlinear system identification. Springer, Berlin
Voet D, Voet JG (2013) Bioquímica. Artmed, Porto Alegre
Russel JB (1994) Química Geral, vol 2. Makron Books, São Paulo
Shuler ML, Kargi F (2001) Bioprocess engineering basic concepts. Prentice Hall PTR, Upper Saddle River
Acknowledgements
São Paulo Research Foundation (FAPESP, Grant #2016/10636–8), Conselho Nacional de Desenvolvimento Científico e Tecnológico – Brasil (CNPq), and Coordenação de Aperfeiçoamento de Pessoal de Nível Superior – Brasil (CAPES – Finance Code 001).
Funding
The researched was supported by São Paulo Research Foundation (FAPESP), Conselho Nacional de Desenvolvimento Científico e Tecnológico – Brasil (CNPq), and Coordenação de Aperfeiçoamento de Pessoal de Nível Superior – Brasil (CAPES).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflicts of interest
The authors declare that they have no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
de Carvalho Lima Torres, A., de Lima, L.N., Tardioli, P.W. et al. Mathematical modeling of enzymatic syntheses of biosurfactants catalyzed by immobilized lipases. Reac Kinet Mech Cat 130, 699–712 (2020). https://doi.org/10.1007/s11144-020-01812-w
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11144-020-01812-w