A STATISTICAL APPROACH FOR OPTIMIZING THE HIGH YIELD GREEN PRODUCTION OF THE FLAVOR ESTER BUTYL BUTYRATE

Authors

  • Ida Nurhazwani Abd Rahman Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia
  • Fatin Myra Abd Manan Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia
  • Nur Haziqah Che Marzuki Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia
  • Naji A. Mahat Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia
  • Nursyafreena Attan Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia
  • Aemi Syazwani Abdul Keyon Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia
  • Joazaizulfazli Jamalis Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia
  • Hassan Y. Aboul-Enein Pharmaceutical and Medicinal Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki, Giza 12622, Egypt
  • Roswanira Abdul Wahab Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia

DOI:

https://doi.org/10.11113/jt.v79.10194

Keywords:

Esterification, butyl butyrate, response surface methodology, Box‒Behnken design

Abstract

Being the prevailing approach for producing esters such as butyl butyrate, the use of chemical route has been linked to numerous disadvantages. Hence, a green alternative method for higher yield production of butyl butyrate by esterification reaction utilizing Novozyme 435 as biocatalysts in a solvent-less system may prove useful. Such approach can be further improved by optimizing the relevant reaction parameters using the Response Surface Methodology by the Box-Benkhen Design attempted in this present study. The reaction parameters evaluated were: substrate molar ratio, time and temperature, and the response of each parameter was measured as percentage conversion yield. Using the Design Expert 7.1.6 optimization functions, the two sets of optimum conditions selected viz. [i] molar ratio butyric acid:butanol 1:3.93, 9.93 h at 56.09°C and [ii] molar ratio butyric acid:butanol 1:3.35, 9.79 h at 53.90°C had afforded the highest yield of butyl butyrate i.e. 99.62% and 99.55%, respectively. The ester product obtained from the reaction were confirmed as butyl butyrate by FTIR and GC. Therefore, the results substantiated the applicability of the RSM prediction technique as well as efficacy of Novozyme 435 as biocatalysts in the high yield solvent-less synthesis of butyl butyrate, adhering to the philosophy of Green Chemistry.

Author Biographies

  • Ida Nurhazwani Abd Rahman, Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia

    Dept. of Chemistry

    Student

  • Fatin Myra Abd Manan, Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia

    Department of Chemistry

    Student

  • Nur Haziqah Che Marzuki, Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia

    Department of Chemistry

    Student

  • Naji A. Mahat, Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia

    Department of Chemistry

    Senior Lecturer

  • Nursyafreena Attan, Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia

    Department of Chemistry

    Senior Lecturer

  • Aemi Syazwani Abdul Keyon, Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia

    Department of Chemistry

    Senior Lecturer

  • Joazaizulfazli Jamalis, Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia

    Department of Chemistry

    Senior Lecturer

  • Hassan Y. Aboul-Enein, Pharmaceutical and Medicinal Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki, Giza 12622, Egypt

    Pharmaceutical and Drug Industries Research Division

    Professor

  • Roswanira Abdul Wahab, Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia

    Department of Chemistry

    Senior Lecturer

References

Ju, I. B., Lim, H-W., Jeon, W., Suh, D. J., Park M-J. & Suh, Y-W. 2011. Kinetic Study of Catalytic Esterification of Butyric Acid and n-butanol over Dowex 50W x 8-400. Chemical Engineering. 168: 293-302.

Mohamad, N. R., Buang, N. A., Mahat, N. A., Huyop, F., Jamalis, J., Aboul-Enein, H. Y. & Wahab, R. A. 2015a. Simple Adsorption of Candida rugosa Lipase Onto Multi-walled Carbon Nanotubes for an Economical and Sustainable Production of the Flavor Ester Geranyl Propionate. Journal of Industrial and Engineering Chemistry. 32: 99-108.

Mohamad, N. R., Mahat, N. A., Lok, Y. Y., Huyop, F., Aboul-Enein, H.Y. & Wahab, R. A. 2015b. A Facile Enzymatic Synthesis of Geranyl Propionate by Physically Adsorbed Candida rugosa Lipase onto Multi-walled Carbon Nanotubes. Enzyme and Microbial Technology 72: 49-55.

Marzuki, N. H. C., Mahat, N. A., Buang, N. A., Huyop, F. & Wahab, R. A. 2015a. Candida rugosa Lipase Immobilized Onto Acid-functionalized Multi Walled Carbon Nanotubes for Sustainable Production of Methyl Oleate. Applied Biochemistry and Biotechnology. 177(4): 967-984.

Chowdhury, A., Mitra, D. & Biswas, D. 2014. Synthesis of Biolubricant Components from Wastes of Cooking Oil Using Biocatalytic Route. Env Prog Sust Ener. 33(3): 933-940.

Rajendran, A., Palaisamy, A. & Thangavelu, V. 2009. Lipase Catalysed Ester Synthesis for Food Processing Industries. Brazilian Archive Biology and Technology. 52: 207-219.

Skoronski, E., Padoin, N., Soares, C. & Furigo Jr. A. 2014. Stability of Immobillized Rhizomucor miehei Lipase for the Synthesis of Pentyl Octanoate in a Continuous Packed Bed Bioreactor. Brazilian Journal of Chemical Engineering. 31(3): 633-641.

Ferraz, L.I.R., Possebom, G., Valandro, A., Luiz, E., Cansian, R., Paroul, N., de Oliveira, D. & Treichel, H. 2015. Application of Home-made Lipase in the Production of Geranyl Propionate by Esterification of Geraniol and Propionic Acid in Solvent-Free System. Biocatal Agri Biotechnol. 4(1): 44-48.

Talebi, M., Vaezifar, S., Jafary, F., Fazilati, F. & Motamedi, S. 2016. Stability Improvement of Immobilized Α-Amylase Using Nano Pore Zeolite. Iranian Journal of Biotechnology. 14(1): e1261.

Zou, B., Hu, Y. & Yu, D. 2010. Immobilization of Porcine Pancreatic Lipase onto Ionic Liquid Modified Mesoporous Silica SBA-15. Biochemical Engineering Journal. 53(1): 150-153.

Kharrat. N., Ali, Y. B., Marzouk, S., Gargouri, Y-T. & Karra-Châabouni, M. 2011. Immobilization of Rhizopus oryzae Lipase on Silica Aerogels by Adsorption: Comparison with the Free Enzyme. Process Biochemistry. 46(5):1083-1089.

Wahab, R., Abdul Rahman, M. B., Chaibakhsh, N., Leow, T. C., Basri, M., Abdul Rahman, R. N. Z. Salleh, A. B. 2014. Enzymatic Production of a Solvent-free Menthyl Butyrate via Response Surface Methodology Catalyzed by a Novel Thermostable Lipase from Geobacillus zalihae. Biotechnology and Biotechnological Equipment. 28(6): 1310-2818.

Marzuki, N. H. C., Mahat, N. A., Aboul-Enein H., Huyop F. & Wahab, R. A. 2015b. Modeling and Optimization of Candida rugosa Nanobioconjugates Catalysed Synthesis of Methyl Oleate by Response Surface Methodology. Biotechnology and Biotechnological Equipment. 29(6): 1113-1127.

Wu, W-J. & Ahn, B-Y. 2014. Statistical Optimization of Ultraviolet Irradiate Conditions for Vitamin D2 Synthesis in Oyster Mushrooms [Pleurotus ostreatus] using Response Surface Methodology. PLoSOne 9[4]: e95359. doi:10.1371/journal.pone.0095359.

Bas¸ D. & Boyacı. I. H. 2007. Modelling and Optimization I: Usability of Response Surface Methodology. Journal of Food and Engineering. 78: 836-845.

Martins, A. B., Graebin, N. G., Lorenzoni, A. S. G., Fernandez-Lafuente, R., Ayub, M. A. Z. & Rodrigues, R. C. 2011. Rapid and High Yields of Synthesis of Butyl Acetate Catalyzed by Novozym 435: Reaction Optimization by Response Surface Methodology. Process Biochemistry. 46(12): 2311-2316.

Mohamad, N. R., Mahat, N. A., Huyop, F., Aboul-Enein, H. Y. & Wahab, R. A. 2015c. Response Surface Methodological Approach for Optimizing Production of Geranyl Propionate Catalysed by Carbon Nanotubes Nanobioconjugates. Biotechnology and Biotechnological Equipment. 29(4): 732-739.

Raghavendra, T., Panchal, N., Divecha, J., Shah, A. & Madamwar, D. 2014. Biocatalytic Synthesis of Flavor Ester “pentyl valerate†using Candida rugosa Lipase Immobilized in Microemulsion based Organogels: Effect of Parameters and Reusability. BioMed Research International. 353845;doi:10.1155/2014/353845.

Low, C. T., Mohamad, R., Tan, C. P., Long, K., Ismail, R., Lo, S. K. & Lai, O. M. 2007. Lipaseâ€catalyzed Production of Mediumâ€Chain Triacylglycerols from Palm Kernel Oil Distillate: Optimization Using Response Surface Methodology. European Journal of Lipid Science and Technology. 109(2): 107-119.

Gunawan, E. R., Basri, M., Abd Rahman, M. B., Salleh, A. B. & Abd Rahman, R. N. Z. 2005. Study on Response Surface Methodology [RSM] of Lipase-catalyzed Synthesis of Palm-based Wax Ester. Enzyme and Microbial Technology. 37: 739-744.

Deepika, K. V., Kalam, S., Sridhar, P. R., Podile, A. R. & Bramchari, P. V. 2016. Optimization of Rhamnolipid Biosurfactant Production by Mangrove Sediment Bacterium Pseudomonas aeruginosa KVD-HR42 Using Response Surface Methodology. Biocatalysis and Agricultural Biotechnology. 5: 38-47.

Liu, W., Yin, P., Liu, X. & Qu, R. 2014. Design of an Effective Bifunctional Catalyst Organotriphosphonic Acid-functionalized Ferric Alginate [ATMP-FA] and Optimization by Box–Behnken Model for Biodiesel Esterification Synthesis of Oleic Acid Over ATMP‒FA. Bioresource Technology. 173: 266-271.

Abdul Rahman, M. B., Chaibakhsh, N., Basri, M., Rahman, R. N. Z. A. & Salleh, A. B. 2008. Modelling and Optimization of Lipase-catalyzed Synthesis of Dilauryl Adipate Ester by Response Surface Methodology. Journal of Chemical Technology and Biotechnology. 83: 1534-1540.

Pujari, V. & Chandra, T. 2000. Statistical Optimization of Medium Components for Enhanced Riboflavin Production by a UV Mutant of Eremothycium ashbyii. Process Biochemistry. 36(1): 31-37.

Nuthalapati, V., Ramalingam, C., Dasgupta, N., Ranjan, S., Varghese, L. R. & Mandal, S. K. 2014. Optimization of Growth Medium Using a Statistical Approach for the Production of Plant Gallic Acid from a Newly Isolated Aspergillus tubingenesis NJA-1. Journal of Pure and Applied Microbiology. 8: 3313-3324.

Salihu, A., Alam, M. Z., Karim, M. I. A. & Salleh, H. M. 2014. Esterification for Butyl Butyrate Formation using Candida cylindracea Lipase Produced from Palm Oil Mill Effluent Supplemented Medium. Arabian Journal of Chemistry. 7(6): 1159-1165.

Chaibakhsh, N., Rahman, M. B. A., Abd-Aziz, S., Basri, M., Salleh, A. B. & Rahman, R. N. Z. R. A. 2009. Optimized Lipase-catalyzed Synthesis of Adipate Ester in a Solvent-free System. Journal of Industrial Microbiology and Biotechnology. 36(9): 1149-1155.

Dwivedi, G. & Sharma, M.P. 2015. Application of Box–Behnken Design in Optimization of Biodiesel Yield from Pongamia Oil and Its Stability Analysis. Fuel. 145: 256-262.

Abdul Rahman, M. B., Chaibakhsh, N. & Basri, M. 2011. Effect of Alcohol Structure on the Optimum Condition for Novozyme 435-catalyzed Synthesis of Adipate Esters. Biotechnol Research International. doi:10.4061/2011/162987.

Isah, A. A., Mahat, N. A., Jamalis, J., Attan. N., Zakaria, I.I., Huyop, F. & Wahab. R. A. 2016. Synthesis of Geranyl Propionate in a Solvent-free Medium using Rhizomucor miehei Lipase Covalently Immobilized on Chitosan-graphene Oxide Beads. Preparative Biochemistry and Biotechnology. DOI:10.1080/10826068.2016.1201681.

Verissimo, L. A. A., Soares, W. C. L., Mol, P. C. G., Minim, V. P. R., da Silva, M. C. H. &Minim, L. A. 2015. Optimization of Flavor Ester Synthesis Catalysed by Aspergillus niger Lipase. African Journal of Microbial Research. 9(13): 922-928.

Paroul, N., Grzegozeski, L.P., Ciaradia, V., Treichel, H., Cansian, R. L., de Oliveira. V. & de Olivera, D. 2010. Production of Geranyl Propionate by Enzymatic Esterification of Geraniol and Propionic in Solvent Free System. Journal of Chemical Technology and Biotechnology. 85(12): 1636-1641.

Couto, R., Vidinha, P., Peres, C., Ribeiro, A. S., Ferreira, O., Oliveira, M. V. & Barreiros, S. 2011. Geranyl Acetate Synthesis in a Packed-bed Reactor Catalyzed by Novozyme in Supercritical Carbon Dioxide and in Supercritical Ethane. Industrial Engineering Chemistry Research. 50(4): 1938-1946.

Manan, F. M. A., Rahman, I. N. A., Marzuki, N. H. C., Mahat, N. A., Huyop, F. & Wahab, R. A. 2016. Statistical Modelling of Eugenol Benzoate Synthesis using Rhizomucor miehei Lipase Reinforced Nanobioconjugates. Process Biochemistry. 51(2): 249-262.

Soyer, A., Bayraktar, E. & Mehmetoglu, Ü. 2010. Optimization of Lipase-catalyzed Enantioselective Production of 1‒phenyl 1‒propanol using Response Surface Methodology. Preparative Biochemistry Biotechnology. 40(4): 389-404.

Yadav, G. D. & Lathi, P. S. 2004. Synthesis of Citronellol Laurate in Organic Media Catalyzed by Immobilized Lipases: Kinetic Studies. Journal of Molecular Catalysis B: Enzymatic. 27: 113-119.

Chen, X.; Yin, P.; Du, W.; Liu, D. 2008. Effect of Several Factors on Soluble Lipase-mediated Biodiesel Preparation in the Biphasic Aqueous-oil Systems. World J Microbiol Biotechnol. 24: 2097-2102.

Wade Jr, L. G. 2013. Organic Chemistry. 8th Edition. Pearson Publishing, Boston, MA.

Stuart, B. H., George, W. O., McIntyre, P. S. 1996. Modern Infrared Spectroscopy. John Wiley and Sons, Inc., Chichester. 200.

Bruno, L. M., de Lima Filho, J. L. & de Castro, H. F. 2008. Comparative Performance of Microbial Lipases Immobilized on Magnetic Polysiloxane Polyvinyl Alcohol Particles. Brazilian Archive of Biololgy and Technology. doi.org/10.1590/S1516-89132008000500003.

Downloads

Published

2017-10-22

Issue

Section

Science and Engineering

How to Cite

A STATISTICAL APPROACH FOR OPTIMIZING THE HIGH YIELD GREEN PRODUCTION OF THE FLAVOR ESTER BUTYL BUTYRATE. (2017). Jurnal Teknologi, 79(7). https://doi.org/10.11113/jt.v79.10194