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Enhanced synthesis of isoamyl acetate using liquid-gas biphasic system by the transesterification reaction of isoamyl alcohol obtained from fusel oil

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Abstract

In this work, the transesterification reaction of isoamyl alcohol obtained from fusel oil and leading to the synthesis of isoamyl acetate was conducted simultaneously with in situ ethanol removal, which allows to shift the reaction equilibrium toward ester synthesis. The extracellular Aspergillus oryzae lipase was immobilized into calcium alginate. Effects of immobilization conditions on the loading efficiency and on the specific activity of entrapped lipase were investigated. The kinetic transfer of volatile reactants from the reactor was investigated using an experimentally first order kinetic model, in order to approve the feasibility of the liquid-gas system with continuous ethanol removal in the ester synthesis. The effects of the most influent parameters affecting the reaction have been also investigated using a Doehlert matrix design. The better operating conditions for isoamyl acetate synthesis were: a temperature of 68.5°C and a respective isoamyl alcohol and A. oryzae lipase concentration of 0.72 M and 2.39 g/L. At these conditions, the resulting reaction conversion and ethanol extraction yields were of 89.55 and 69.60%, respectively. The use of the fluidized bed reactor with continuous ethanol removal has allowed to improve the reaction conversion which was two times than the conversion higher obtained in batch reactor. Furthermore, under the optimized conditions in the fluidized bed reactor, the reaction conversion and the ethanol extraction yields were increased by 44.8 and 36.2%, respectively.

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References

  1. Hari Krishna, S., S. Divikar, S. G. Prapulle, and N. G. Karanth (2001) Enzymatic synthesis of isoamyl acetate using immobilized lipase from Rhizomucor miehei. J. Biotechnol. 87: 193–201.

    Article  CAS  Google Scholar 

  2. Romero, M. D., L. Calvo, C. Alba, and A. Daneshfar (2007) A kinetic study of isoamyl acetate synthesis by immobilized lipase-catalyzed acetylation in n-hexane. J. Biotechnol. 127: 269–277.

    Article  CAS  Google Scholar 

  3. Bi, F., S. Iqbal, A. Ali, M. Arman, and M. Ul-Hassan (2009) Synthesis of isoamyl acetate of isoamyl alcohol obtained from fusel oil using immobilized Candida Antarctica lipase. J. Chem. Soc. Pak. 31: 485–491.

    CAS  Google Scholar 

  4. Kirdi, R., N. Ben Akacha, and M. Gargouri (2016) Biosynthesis coupled to the extraction of geranyl acetate in a liquid-gas system: Optimization of the transesterification reaction and modeling of the transfer. Chem. Biochem. Eng. Q. 30: 117–125.

    Article  CAS  Google Scholar 

  5. Sun, J., B. Yu, P. Curran, and S.-Q. Liu (2012) Optimisation of flavour ester biosynthesis in an aqueous system of coconut cream and fusel oil catalysed by lipase. Food Chem. 135: 2714–2720.

    Article  CAS  Google Scholar 

  6. Romero, M. D., L. Calvo, C. Alba, A. Daneshfar, and H. S. Ghaziaskar (2005) Enzymatic synthesis of isoamyl acetate with immobilized Candida antaractica lipase in n-hexane. Enz. Microb. Tech. 37: 42–48.

    Article  CAS  Google Scholar 

  7. Knezevic, Z., S. Bobic, A. Milutinovic, B. Obradovic, L. Mojovic, and B. Bugarski (2002) Alginate-immobilized lipase by electrostatic extrusion for the purpose of palm oil hydrolysis in lecithin/isooctane system. Proc. Biochem. 38: 313–318.

    Article  CAS  Google Scholar 

  8. Yadav, G. D. and S. R. Jadhav (2005) Synthesis of reusable lipases by immobilization on hexagonal mesoporous silica and encapsulation in calcium alginate: Transesterification in nonaqueous medium. Micropor. Mesopor. Mater. 86: 215–222.

    Article  CAS  Google Scholar 

  9. Yang, C. H., C. H. Yen, J. J. Jheng, C. Y. Wang, S. S. Chen, P. Y. Huang, K. S. Huang, and J. F. Shaw (2014) Immobilization of Brassica oleracea Chlorophyllase 1 (BoCLH1) and Candida rugosa lipase (CRL) in magnetic alginate beads: An enzymatic evaluation in the corresponding proteins. Molecules 19: 11800–11815.

    Article  Google Scholar 

  10. Kumar, S., K. R. Yadav, and S. Negi (2014) A comparative study of immobilized lipase produced from Penicillium chrysogenum SNP5 on two different anionic carriers for its pH and thermostability. Ind. J. Biotechnol. 13: 301–305.

    CAS  Google Scholar 

  11. Zhang, S., W. Shang, X. Yang, S. Zhang, X. Zhang, and J. Chen (2013) Immobilization of lipase using alginate hydrogel beads and enzymatic evaluation in hydrolysis of p-Nitrophenol butyrate. Bull. Kor. Chem. Soc. 34: 2741–2746.

    Article  Google Scholar 

  12. Vu, H. and V. V. M. Le (2008) Biochemical studies on the immobilization of the enzyme invertase (EC.3.2.1.26) in alginate gel and its kinetics. Asian Food J. 15: 73–78.

    CAS  Google Scholar 

  13. Ozyilmaz, G. and E. Gezer (2010) Production of aroma esters by immobilized Candida rugosa and porcine pancreatic lipase into calcium alginate gel. J. Mol. Catal. B: Enz. 64: 140–145.

    Article  CAS  Google Scholar 

  14. Ferraz, L. I. R., G. Possebom, E. V. Alvez, R. L. Cansian, N. Paroul, D. De Oliveira, and H. Treichel (2015) Application of home-made lipase in the production of geranyl propionate by esterification of geraniol and propionic acid in solvent-free system. Biocatal. Agric. Biotechnol. 4: 44–48.

    Google Scholar 

  15. Padilha, G. S., M. Barros, R. M. Alegre, and E. B. Tambourgi (2013) Production of ethyl valerate from Burkholderia cepacia lipase immobilized in alginate. Chem. Eng. Trans. 32: 1063–1068.

    Google Scholar 

  16. Hiol, A., M. D. Jonzo, N. Rugani, D. Druet, L. Sarda, and L. C. Comeau (2000) Purification and characterization of an extracellular lipase from a thermophilic Rhizopus oryzae strain isolated from palm fruit. Enz. Microb. Tech. 26: 421–430.

    Article  CAS  Google Scholar 

  17. Molinari, F., R. Gandolfi, A. Converti, and M. Zilli (2000) Mycelium-bound carboxylesterase from Aspergillus oryzae: An efficient catalyst for acetylation in organic solvent. Enz. Microb. Tech. 27: 626–630.

    Article  CAS  Google Scholar 

  18. Wehtje, E., J. Kaur, P. Adlercreutz, S. Chand, and B. Mattiasson (1997) Water activity control in enzymatic esterification processes. Enz. Microb. Tech. 2: 502–510.

    Article  Google Scholar 

  19. Kumari, A., P. Mahapatra, V. K. Garlapati, R. Banerjee, and S. Dasgupta (2009) Lipase mediated isoamyl acetate synthesis in solvent-free system using vinyl acetate as acyl donor. Food Technol. Biotechnol. 47: 13–18.

    CAS  Google Scholar 

  20. Ben Akacha, N. and M. Gargouri (2015) Microbial and enzymatic technologies used for the production of natural aroma compounds: Synthesis, recovery modelling, and bioprocesses. Food Bioprod. Proc. 94: 675–706.

    Article  Google Scholar 

  21. Gubicza, L., A. Kabiri-Badr, E. Keoves, and K. Belafi-Bako (2000) Large-scale enzymatic production of natural flavour esters in organic solvent with continuous water removal. J. Biotechnol. 84: 193–196.

    Article  CAS  Google Scholar 

  22. Figueiredo, K. C. S., V. M. M. Salim, and C. P. Borges (2010) Ethyl oleate production by means of pervaporation-assisted esterification using heterogeneous catalysis. Braz. J. Chem. Eng. 27: 609–617.

    Article  CAS  Google Scholar 

  23. Ben Akacha, N., O. E. Guizani, and M. Gargouri (2007) Improvement and modeling of hexenal transfer in liquid-gas reactor. Appl. Biochem. Biotechnol. 14: 276–283

    Article  Google Scholar 

  24. Bartling, K., J. U. S. Thompson, P. H. Pfromm, P. Czermak, and M. E. Rezac (2001) Lipase-catalyzed synthesis of geranyl acetate in n-hexane with membrane-mediated water removal. Biotechnol. Bioeng. 75: 676–681.

    Article  CAS  Google Scholar 

  25. Hermann, R., M. Lehmann, and Büchs (2002) Characterization of gas-liquid mass transfer phenomena in microtiter plates. Biotechnol. Bioeng. 81: 178–186.

    Article  Google Scholar 

  26. Converti, A., A. Del Borghi, R. Gandolfi, F. Molinari, E. Palazzi, P. Perego, and M. Zilli (2002) Simplified kinetics and thermodynamyics of geraniol acetylation by lyophilized cells of Aspergillus oryzae. Enz. Microb. Tech. 30: 216–223.

    Article  CAS  Google Scholar 

  27. Adham, N. Z. and E. M. Ahmed (2009) Extracellular lipase of Aspergillus niger NRRL3; production, partial purification and properties. Ind. J. Microbiol. 49: 77–83.

    Article  CAS  Google Scholar 

  28. Bradford, M. M. (1976) A rapid and sensitive method for the quantitation of microgram quantitation of microgram of protein utilizing the principale of protein-Dye-binding. Anal. Biochem. 72: 248–254.

    Article  CAS  Google Scholar 

  29. Amenaghawon, N. A., K. E. Okhueleigbe, S. E. Ogbeide, and C. O. Okieimen (2014) Modelling the kinetics of steam distillation of essential oils from lemon grass (Cymbopogon Spp.). Int. J. Appl. Sci. Eng. 12: 107–115.

    Google Scholar 

  30. Murphy, G. M. (1960) Ordinary Differential Equations and Their Solutions. pp. 25–26. Van Nostrand, Princeton. New Jersey, USA.

    Google Scholar 

  31. Won, K., S. Kim, K. Kim, H. W. Park, and S. Moon (2005) Optimization of lipase entrapment in Ca-alginate gel beads. Proc. Biochem. 40: 2149–2154.

    Article  CAS  Google Scholar 

  32. Cheirsilp, B., P. Jeamjounkhaw, and A. H. Kittikun (2009) Optimizing an alginate immobilized lipase for monoacylglycerol production by the glycerolysis reaction. J. Mol. Catal. B: Enz. 59: 206–211.

    Article  CAS  Google Scholar 

  33. Bhushan, I., R. Parshad, G. N. Qazi, and V. K. Gupta (2008) Immobilization of lipase by entrapement in Ca-alginate beads. J. Bioact. Compact. Polym. 23: 552–562.

    Article  CAS  Google Scholar 

  34. Wolfson, A., A. Atyya, C. Dlugy, and D. Tavor (2010) Glycerol triacetate as solvent and acyl donor in the production of isoamyl acetate with Candida antarctica lipase B. Bioproc. Biosyst. Eng. 33: 363–366.

    Article  CAS  Google Scholar 

  35. Rizzi, M., P. Stylos, A. Riek, and M. Reuss (1992) A kinetic study of immobilized lipase catalysing the synthesis of isoamyl acetate by transesterification in n-hexane. Enz. Microb. Tech. 14: 709–714.

    Article  CAS  Google Scholar 

  36. Ganapati, D. Y. and H. Archana (2003) Kinetic modeling of immobilized-lipase catalyzed transesterification of n-octanol with vinyl acetate in non-aqueous media. Enz. Microb. Tech. 32: 783–789.

    Article  Google Scholar 

  37. Jin, Z., J. Ntwali, S. Y. Han, S. P. Zheng, and Y. Lin (2012) Production of flavor esters catalyzed by CALB-displaying Pichia pastoris whole-cells in a batch reactor. J. Biotechnol. 159: 108–114.

    Article  CAS  Google Scholar 

  38. Damnjanović, J. J., M. G. Žuža, J. K. Savanović, D. I. Bezbradica, D. Ž. Mijin, N. Bošković-Vragolović, and Z. D. Knežević-Jugović (2012) Covalently immobilized lipase catalyzing highyielding optimized geranyl butyrate synthesis in a batch and fluidized bed reactor. J. Mol. Catal. B: Enz. 75: 50–59.

    Article  Google Scholar 

  39. Ghamgui, H., M. Karra-Chaâbouni, S. Bezzine, N. Miled, and Y. Gargouri (2006) Production of isoamyl acetate with immobilized Staphylococcus simulans lipase in a solvent-free system. Enz. Microb. Tech. 38: 788–794.

    Article  CAS  Google Scholar 

  40. Yadav, G. D. and P. S. Lathi (2004) Synthesis of citronellol laurate in organic media catalyzed by immobilized lipases: Kinetic studies. J. Mol.Catal. B: Enz. 27: 113–119.

    Article  CAS  Google Scholar 

  41. Rodrigues, D. S., G. P. Cavalcante, A. L. O. Ferreira, and L. R. B. Gonçalves (2008) Immobilization of Candida antarctica lipase type B by adsorption on activated carbon. Chem. Biochem. Eng. Q. 22: 125–133.

    CAS  Google Scholar 

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Authors and Affiliations

  1. Biocatalysis and Industrial Enzymes Group, Laboratory of Microbial Ecology and Technology, National Institute of Applied Sciences and Technology, (INSAT) Tunis, University of Carthage Tunis, Tunis, Tunisia

    Rachida Kirdi, Yosra Messaoudi & Mohamed Gargouri

  2. Laboratory of Natural Substances, National Institute of Research and Physical and Chemical Analysis (INRAP), Biotechnopôle Sidi Thabet, 2020, Ariana, Tunisia

    Najla Ben Akacha

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  1. Rachida Kirdi
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  2. Najla Ben Akacha
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  4. Mohamed Gargouri
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Correspondence to Rachida Kirdi.

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Kirdi, R., Ben Akacha, N., Messaoudi, Y. et al. Enhanced synthesis of isoamyl acetate using liquid-gas biphasic system by the transesterification reaction of isoamyl alcohol obtained from fusel oil. Biotechnol Bioproc E 22, 413–422 (2017). https://doi.org/10.1007/s12257-016-0616-4

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  • DOI: https://doi.org/10.1007/s12257-016-0616-4

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