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Lipase-catalyzed synthesis of propyl-phenyl acetate: a kinetic and thermodynamic study

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Abstract

This study focuses on the synthesis of propyl-phenyl acetate via esterification reaction in the presence of immobilized Candida antartica lipase-B (CAL-B). In this work, the effect of relevant factors (kinetics and thermodynamic) on total percent conversion and process optimization was studied. The reaction was performed in heptane medium with 1:2 molar ratio of benzoic acid: n-propanol with 0.6% (w/v) biocatalyst loading at 40 °C to attain a maximum conversion of 96.1% within 40 min of reaction time. Effect of increase in temperature on ∆G values indicates that lipase is more promising at moderate temperature (40 °C). A second-order kinetic model was proposed to evaluate apparent kinetic constants that indicate a good agreement between the experimental and theoretical data (0.94 ≤ R2 ≤ 0.99) with high initial reaction rate (113.5 mM/min). Finally, the catalyst CAL-B was successfully reused eight times without any significant decrease in relative activity.

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References

  1. Nurazwa I, Lajis A, Mohamad R, Ariff A, Mohamed S, Halim M, Wasoh H (2018) Kinetics and optimization of lipophilic kojic acid derivative synthesis in polar aprotic solvent using lipozyme RMIM and its rheological study. Molecules 23:501

    Google Scholar 

  2. Basri M, Rahman A, Kassim A, Shahruzzaman R, Mokles M (2019) Lipase-catalyzed production and purification of palm esters using stirred tank reactors (STR). Biocatal Biotransform 3:56–60

    Google Scholar 

  3. Kim H, Kim T, Choi N, Kim B, Oh S, Kim I (2019) Synthesis of diethylhexyl adipate by Candida antarctica lipase-catalyzed esterification. Process Biochem 78:58–62

    CAS  Google Scholar 

  4. Dill LP, Kochepka DM, Krieger N, Ramos LP (2018) Synthesis of fatty acid ethyl esters with conventional and microwave heating systems using the free lipase B from Candida antarctica. Biocatal Biotransform 37:25–34

    Google Scholar 

  5. Kalghatgi SG, Bhanage BM (2019) Green syntheses of levulinate esters using ionic liquid 1-methyl imidazolium hydrogen sulphate [MIM][HSO4] in solvent free system. J Mol Liq 281:70–80

    CAS  Google Scholar 

  6. Lamprecht Z, Moeng MM, Liles D, Lotz S, Bezuidenhout D (2019) Thiophene site activation: synthesis and structures of Fischer carbene complexes with 3,3′- and 2,3′-bithienyl substituents. Polyhedron 158:193–207

    CAS  Google Scholar 

  7. Preczeski KP, Kamanski AB, Scapini T, Camargo AF, Modkoski TA, Rossetto V, Venturin B, Mulinari J, Golunski SM, Mossi AJ, Treichel H (2018) Efficient and low-cost alternative of lipase concentration aiming at the application in the treatment of waste cooking oils. Bioprocess Biosyst Eng 41:851–857

    CAS  PubMed  Google Scholar 

  8. Zenevicz MCP, Jacques A, Silva MJA, Agenor FJ, Vladimir O, Débora O (2018) Study of a reactor model for enzymatic reactions in continuous mode coupled to an ultrasound bath for esters production. Bioprocess Biosyst Eng 41:1589–1597

    CAS  PubMed  Google Scholar 

  9. Botton V, Piovan L, Meier HF, Mitchell DA, Cordova J, Krieger N (2018) Optimization of biodiesel synthesis by esterification using a fermented solid produced by Rhizopus microsporus on sugarcane bagasse. Bioprocess Biosyst Eng 41:573–583

    CAS  PubMed  Google Scholar 

  10. Wancura JH , Rosset DV, Brondani M, Mazutti MA, Oliveira JV, Tres MV, Jahn SL (2018) Soluble lipase-catalyzed synthesis of methyl esters using a blend of edible and nonedible raw materials. Bioprocess Biosyst Eng 41:1185–1193

    CAS  PubMed  Google Scholar 

  11. Trentin CM, Scherer RP, Dalla Rosa C, Treichel H, Oliveira D, Oliveira JV (2014) Continuous lipase-catalyzed esterification of soybean fatty acids under ultrasound irradiation. Bioprocess Biosyst Eng 37:841–847

    CAS  PubMed  Google Scholar 

  12. Encinar JM, González JF, Sánchez N, Nogales-Delgado S (2019) Sunflower oil transesterification with methanol using immobilized lipase enzymes. Bioprocess Biosyst Eng 42:157–166

    CAS  PubMed  Google Scholar 

  13. de Oliveira CT, Alves EA, Todero I, Kuhn RC, de Oliveira D, Mazutti  MA (2019) Production of cutinase by solid-state fermentation and its use as adjuvant in bioherbicide formulation. Bioprocess Biosyst Eng 3:56–60

    Google Scholar 

  14. Satyawali Y, Akemeier V, Dejonghe W, De Wever H, Van Hecke W (2019) Lipase-catalyzed solvent-free esterification of furan containing components. Waste Biomass Valoriz 10:311–317

    CAS  Google Scholar 

  15. Li Z, Yang D, Jiang L, Ji J, Ji H, Zeng X (2007) Lipase-catalyzed esterification of conjugated linoleic acid with L-carnitine in solvent-free system and acetonitrile. Bioprocess Biosyst Eng 30:331–336

    CAS  PubMed  Google Scholar 

  16. Elsayed NS, Aboshanab KM, Yassien MA, Hassouna NA (2018) Kinetic modeling, recovery, and molecular characterization of poly-beta-hydroxybutyrate polymer in Acinetobacter baumannii isolate P39. Bioprocess Biosyst Eng 41:1779–1791

    CAS  PubMed  Google Scholar 

  17. Tomke PD, Rathod VK (2016) Enzyme as biocatalyst for synthesis of octyl ethanoate using acoustic cavitation: optimization and kinetic study. Biocatal Agric Biotechnol 7:145–153

    Google Scholar 

  18. Pereira GN, Holz JP, Giovannini PP, Oliveira JV, de Oliveira D, Lerin LA (2018) Enzymatic esterification for the synthesis of butyl stearate and ethyl stearate. Biocatal Agric Biotechnol 16:373–377

    Google Scholar 

  19. Zhang XM, Ai NS, Wang J, Tong FP, Zheng BG (2016) Lipase-catalyzed modification of the flavor profiles in recombined skim milk products by enriching the volatile components. J Dairy Sci 99:8665–8679

    CAS  PubMed  Google Scholar 

  20. Tomke PD, Zhao X, Chiplunkar PP, Xu B, Wang H, Silva C, Rathod VK, Cavaco-Paulo A (2017) Lipase-ultrasound assisted synthesis of polyesters. Ultrasonic sonochem 38:496–502

    CAS  Google Scholar 

  21. Bilgiç-Keleş S, Şahin-Yeşilçubuk N, Barla-Demirkoz A, Karakaş M (2019) Response surface optimization and modelling for supercritical carbon dioxide extraction of Echium vulgare seed oil. J Supercrit Fluids 143:365–369

    Google Scholar 

  22. Laudani CG, Habulin M, Knez Z, Giovanna R (2007) Lipase-catalyzed long chain fatty ester synthesis in dense carbon dioxide: kinetics and thermodynamics. J Supercrit Fluids 41:92–101

    CAS  Google Scholar 

  23. Li K, Xue W, Zeng Z, Shi X (2018) Kinetics of the reaction of ethanol and lauric acid catalyzed by deep eutectic solvent based on benzyltrimethylammonium chloride. Can J Chem Eng 97:1144–1151

    Google Scholar 

  24. Pleiss J (2018) Thermodynamic Activity-based progress curve analysis in enzyme kinetics. Trends Biotechnol 36:234–238

    CAS  PubMed  Google Scholar 

  25. Kamaruzaman MR, Chin SY, Pui ECL, Prasetiawan H, Nurwadiah A (2019) Synthesis of biobased polyester polyol through esterification of sorbitol with azelaic acid catalyzed by Tin(II) oxide: a kinetic modeling study. Ind Eng Chem Res 58:510–516

    CAS  Google Scholar 

  26. Lima LCD, Peres DGC, Mendes AA (2018) Kinetic and thermodynamic studies on the enzymatic synthesis of wax ester catalyzed by lipase immobilized on glutaraldehyde-activated rice husk particles. Bioprocess Biosyst Eng 41:991–1002

    CAS  PubMed  Google Scholar 

  27. Zhang Y, Zhao Y, Gao X, Jiang W, Li Z, Yao Q, Yang F, Wang F, Liu J (2019) Kinetic model of the enzymatic Michael addition for synthesis of mitomycin analogs catalyzed by immobilized lipase from T. laibacchii. Mol Catal 466:146–156

    CAS  Google Scholar 

  28. Zainol MM, Amin NAS, Asmadi M (2019) Kinetics and thermodynamic analysis of levulinic acid esterification using lignin-furfural carbon cryogel catalyst. Renew Energy 130:547–557

    CAS  Google Scholar 

  29. Cha HJ, Park JB, Park S (2019) Esterification of secondary alcohols and multi-hydroxyl compounds by Candida antarctica lipase B and subtilisin. Biotechnol Bioprocess Eng 7:1–7

    Google Scholar 

  30. Yu H, Lee M, Shin H, Park K, Chang P (2018) Lipase-catalyzed solvent-free synthesis of erythorbyl laurate in a gas-solid-liquid multiphase system. Food Chem 271:445–449

    PubMed  Google Scholar 

  31. He WS, Li L, Zhao J, Xu H, Rui J, Cui D, Li H, Zang H, Liu X (2019) Candida sp. 99–125 lipase-catalyzed synthesis of ergosterol linolenate and its characterization. Food Chem 280:286–293

    PubMed  Google Scholar 

  32. Kim H, Nakyung C, Kim Y, Kim H, Leee J, Kim I (2019) Immobilized lipase-catalyzed esterification for synthesis of trimethylolpropane triester as a biolubricant. Renew Energy 130:489–494

    CAS  Google Scholar 

  33. Tomke PD, Rathod VK (2015) Ultrasound assisted lipase catalyzed synthesis of cinnamyl acetate via transesterification reaction in a solvent free medium. Ultrason Sonochem 27:241–246

    CAS  PubMed  Google Scholar 

  34. Devulapelli VG, Weng HS (2009) Synthesis of cinnamyl acetate by solid-liquid phase transfer catalysis: Kinetic study with a batch reactor. Catal Commun 10:1638–1642

    CAS  Google Scholar 

  35. Nakhjiri MT, Marandi GB, Kurdtabar M (2018) Poly(AA-co-VPA) hydrogel cross-linked with N-maleyl chitosan as dye adsorbent: Isotherms, kinetics and thermodynamic investigation. Int J Biol Macromol 117:152–166

    CAS  PubMed  Google Scholar 

  36. Angajala G, Pavan P, Subashini R (2016) Lipases: an overview of its current challenges and prospectives in the revolution of biocatalysis. Biocatal Agric Biotechnol 7:257–270

    Google Scholar 

  37. Tomke PD, Rathod VK (2018) A novel step towards immobilization of biocatalyst using agro waste and its application for ester synthesis. Int J Biol Macromol 117:366–376

    CAS  PubMed  Google Scholar 

  38. Aguieiras ECG, de Barros DSN, Fernandez-Lafuente R, Freire DMG (2019) Production of lipases in cottonseed meal and application of the fermented solid as biocatalyst in esterification and transesterification reactions. Renew Energy 130:574–581

    CAS  Google Scholar 

  39. Papamichael EM, Theodorou LG (2006) Enzyme kinetics and modeling of enzymatic systems. Biocatal Agric Biotechnol 7:25–29

    Google Scholar 

  40. Ding J, Yang Z, Zhao Y, Fang W, Lu Q (2019) Lipase-catalyzed synthesis of ethyl (R)-2-benzyloxy-2-isopropylhydrogenmalonate: a useful combination of chemical synthesis with enzymatic methods. Biosci Biotechnol Biochem 83(4):763–767

    Google Scholar 

  41. Bansode SR, Hardikar MA, Rathod VK (2017) Evaluation of reaction parameters and kinetic modelling for Novozym 435 catalysed synthesis of isoamyl butyrate. J Chem Technol Biotechnol 92:1306–1314

    CAS  Google Scholar 

  42. Pedro KCNR, Ferreira IEP, Henriques CA, Langone MAP (2019) Enzymatic fatty acid ethyl esters synthesis using acid soybean oil and liquid lipase formulation. Chem Eng Commun 207:43–55

    Google Scholar 

  43. Chen Y, Liu J, Geng S, Liu Y, Ma H, Zheng J, Liu B, Liang G (2019) Lipase-catalyzed synthesis mechanism of tri-acetylated phloridzin and its antiproliferative activity against HepG2 cancer cells. Food Chem 277:186–194

    CAS  PubMed  Google Scholar 

  44. Guldhe A, Singh P, Renuka N, Bux F (2019) Biodiesel synthesis from wastewater grown microalgal feedstock using enzymatic conversion: a greener approach. Fuel 237:1112–1118

    CAS  Google Scholar 

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Acknowledgements

The authors would like to acknowledge the University Grants Commission (UGC) of India for financial support in the research work.

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Correspondence to Virendra K. Rathod.

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Tomke, P.D., Rathod, V.K. Lipase-catalyzed synthesis of propyl-phenyl acetate: a kinetic and thermodynamic study. Bioprocess Biosyst Eng 43, 1659–1670 (2020). https://doi.org/10.1007/s00449-020-02358-w

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  • DOI: https://doi.org/10.1007/s00449-020-02358-w

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