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Synthesis of n-butyl acetate via reactive distillation column using Candida Antarctica lipase as catalyst

  • Honghai WangEmail author
  • Wenjing Liu
  • Liya Gao
  • Yifan Lu
  • Erxuan Chen
  • Yuchao Xu
  • Hongli Liu
Research Paper

Abstract

The reactive distillation process for the synthesis of n-butyl acetate via transesterification of ethyl acetate with n-butyl alcohol catalyzed by immobilized lipase was simulated and experimentally tested in this work. Based on the reaction kinetics, a reactive distillation process model was developed. The effects of theoretical stages number in the reaction section, the rectifying section and stripping section, reflux ratio, feed molar ratio and relative feed position on the transesterification distillation process were investigated. The transesterification of ethyl acetate with n-butyl alcohol was carried out in a small-scale reactive distillation column. The results showed that the optimal operating conditions are as follows: reaction section stages were 13, rectifying section stages were six, stripping section stages were five, reflux ratio was 1, mole ratio of ethyl acetate and n-butanol was 3:1, the feeding positions of n-butanol and ethyl acetate were at the top and bottom of the reaction section, respectively. Compared to the batch reaction with only 60% conversion of n-butanol, the reactive distillation column can improve the conversion of n-butanol (up to 93.6%).At the same time, the experiment verified that the conversion of n-butanol could still reach 72.5%, after the lipase-loaded packing storage in the reaction system at 70 °C for 120 days.

Keywords

Lipase Reactive distillation Transesterification Simulation 

Notes

Acknowledgements

This work was supported by the National Natural Science Foundation of China (Grant no. 21878066) and the Special Correspondent Project of Tianjin(Grant no. 18JCTPJC56500). The authors wish to thank all the partners of our laboratory.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

References

  1. 1.
    An WZ, Lin ZX, Jiang Y, Chen F, Zhou LP, Zhu JM (2013) Design and optimization of an internally heat integrated reactive distillation column for ethylene glycol production. CIESC J 64:4634–4640Google Scholar
  2. 2.
    Gao X, Zhao Y, Li H, Li XG (2018) Review of basic and application investigation of reactive distillation technology for process intensification. CIESC J 69:218–238Google Scholar
  3. 3.
    Arpornwichanop A, Wiwittanaporn C, Authayanun S, Assabumrungrant S (2008) The use of dilute acetic acid for butyl acetate production in a reactive distillation: simulation and control studies. Korean J Chem Eng 25(1252–1266):xGoogle Scholar
  4. 4.
    Liu JJ, Yang BL, Lu SQ (2013) Multi-scale study of reactive distillation. Chem Eng J 225:280–291CrossRefGoogle Scholar
  5. 5.
    Mauro B, Kusumaningtyas Dewi R, Gozzelino Giuseppe (2014) Reactive distillation in the intensification of oleic acid esterification with methanol-A simulation case-study. J Ind Eng Chem 20(6):4242–4249CrossRefGoogle Scholar
  6. 6.
    Zuo CC, Ge TT, Li CS, Cao SS, Zhang SJ (2016) Kinetic and reactive distillation for acrylic acid synthesis via transesterification. Ind Eng Chem Res 55:8281–8291CrossRefGoogle Scholar
  7. 7.
    Suo XM, Ye Q, Li R, Dai X, Yu H (2016) The partial heat-integrated pressure-swing reactive distillation process for transesterification of methyl acetate with isopropanol. Chem Eng Process 107:42–57CrossRefGoogle Scholar
  8. 8.
    Tong LW, Chen LF, Ye YM (2015) Kinetic studies on the dimerization of isobutene with Ni/Al2O3 as a catalyst for reactive distillation process. Chin J Chem Eng 23:520–527CrossRefGoogle Scholar
  9. 9.
    Wang WT, Lu P, Ma YM (2017) Solid acid catalyst for the esterification of high free fatty acids of Zanthoxylum bungeanum seed oil. Chem Ind Eng Prog 36:2504–2510Google Scholar
  10. 10.
    Zhou SL, Jiang DB, Liu XX, Chen YP, Yin DL (2018) Titanate nanotubes-bonded organosulfonic acid as solid acid catalyst for synthesis of butyl levulinate. RSC Adv 28:3657–3662CrossRefGoogle Scholar
  11. 11.
    Jie HM, Cui XB, Peng YM, Li XB, Xu L, Lin RR (2016) Synthesis of ethyl acetate via reactive and extractive distillation column using ionic liquids as catalyst and entrainer. CIESC J 67:606–613Google Scholar
  12. 12.
    Wohlgemuth R (2010) Biocatalysis: key to sustainable industrial chemistry. Curr Opin Biotechnol 21:713–724CrossRefGoogle Scholar
  13. 13.
    Sanchez S, Demain A (2011) Enzymes and bioconversions of industrial, pharmaceutical, and biotechnological significance. Org Process Res Dev 15:224–230CrossRefGoogle Scholar
  14. 14.
    Wierschem M, Boll S, Lutze P, Gorak A (2016) Evaluation of the enzymatic reactive distillation for the production of chiral compounds. Chem Ing Tec 88:147–157CrossRefGoogle Scholar
  15. 15.
    Santos JC, Nunes GFM, Moreira ABR, Perez VH, Castro HFD (2010) Characterization of Candida rugosa lipase immobilized on poly(N-methylolacrylamide) and its application in butyl butyrate synthesis. Chem Eng Technol 30:1255–1261CrossRefGoogle Scholar
  16. 16.
    Jiang YJ, Wen Q, Wang WQ, Zhou LY, Gao J (2012) Preparation of immobilized lipase through combination of cross-linked enzyme aggregates and biomimetic silicification. Catal J 33:857–862Google Scholar
  17. 17.
    Gao J, Kong WX, Zhou LY, He Y, Ma L, Wang Y, Yin LY, Jiang YJ (2017) Monodisperse core-shell magnetic organosilica nanoflowers with radial wrinkle for lipase immobilization. Chem Eng J 309:70–79CrossRefGoogle Scholar
  18. 18.
    Li H, Xiao CC, Li XG, Gao X (2017) Synthesis of n-amyl acetate in a pilot plant catalytic distillation column with seepage catalytic packing internal. Ind Eng Chem Res 56:12726–12737CrossRefGoogle Scholar
  19. 19.
    Paiva AL, van Rossum D, Malcata FX (2003) Lipase-catalyzed synthesis of butyl butyrate by alcoholysis in an integrated liquid–vapor system. Biotechnol Prog 19:750–754CrossRefGoogle Scholar
  20. 20.
    Heils R, Sont A, Bubenheim P, Liese A, Smirnova I (2012) Integration of enzymatic catalysts in a reactive distillation column with structured packings. Ind Eng Chem Res 51:11482–11489CrossRefGoogle Scholar
  21. 21.
    Heils R, Niesbach A, Wierschem M, Claus D, Soboll S, Lutze P, Smirnova I (2014) Integration of enzymatic catalysts in a continuous reactive distillation column: reaction kinetics and process simulation. Ind Eng Chem Res 50:19612–19619CrossRefGoogle Scholar
  22. 22.
    Heils R, Jensen J-H, Wichert S, Behrens N, Fabuel-Ortega M, Liese A, Smirnova I (2015) Enzymatic reactive distillation: kinetic resolution of rac-2-pentanol with biocatalytic coatings on structured packings. Ind Eng Chem Res 54:9458–9467CrossRefGoogle Scholar
  23. 23.
    Heils R, Hu X, Liese A, Smirnova I (2016) In situ production and renewal of biocatalytic coatings for use in enzymatic reactive distillation. Chem Eng J 306:992–1000CrossRefGoogle Scholar
  24. 24.
    Wierschem M, Schlimper S, Heils R, Smirnova I, Kiss AA, Skiborowski M, Lutze P (2017) Pilot-scale validation of enzymatic reactive distillation for butyl butyrate production. Chem Eng J 312:106–117CrossRefGoogle Scholar
  25. 25.
    Kühn S, Sluyter G, Christlieb MA, Heils R, Stöbener A, Kleber J, Smirnova I, Liese A (2017) In situ separation of the chiral target compound (s)–2-pentanol in biocatalytic reactive distillation. Ind Eng Chem Res 56:6451–6461CrossRefGoogle Scholar
  26. 26.
    Wang HH, Li X, Li CL, Liu WJ (2017) Kinetics of n-butyl acetate prepared by immobilized enzyme. CIESC J 68:4685–4690Google Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  • Honghai Wang
    • 1
    • 2
    Email author
  • Wenjing Liu
    • 1
    • 2
  • Liya Gao
    • 2
  • Yifan Lu
    • 1
    • 2
  • Erxuan Chen
    • 3
  • Yuchao Xu
    • 3
  • Hongli Liu
    • 1
    • 2
  1. 1.School of Chemical EngineeringHebei University of TechnologyTianjinChina
  2. 2.National-Local Joint Engineering Laboratory for Energy Conservation of Chemical Process Integration and Resources UtilizationHebei University of TechnologyTianjinChina
  3. 3.Tianjin Tianou Zhengan Detection Technology Co., LtdTianjinChina

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