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Remarkable effects of deep eutectic solvents on the esterification of lactic acid with ethanol over Amberlyst-15

  • Catalysis, Reaction Engineering
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Abstract

Deep eutectic solvents (DESs) are widely used in numerous reactions both as a solvent and a catalyst. In this study, different types of DESs were investigated as a supplementary component for Amberlyst-15 to enhance its catalytic activity in the esterification reaction of lactic acid with ethanol. The effects of the following parameters such as DES type, choline chloride: glycerol (ChCl-Gly) (1 : 2) amount, molar ratio of reactants, temperature and agitation rate on the initial rate of reaction and yield of ethyl lactate were investigated. According to the results, DESs alone did not have any catalytic effect on the esterification; however, DESs together with Amberlyst-15 provided a significant increase in the initial rate of reaction and yield. The activation energy of the reaction decreased significantly with the combined use of Amberlyst-15 and ChCl-Gly (1 : 2). Internal and external mass transfer limitations were found to be negligible under optimum reaction conditions.

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References

  1. E. L. Smith, A. P. Abbott and K. S. Ryder, Chem. Rev., 114, 11060 (2014).

    Article  CAS  PubMed  Google Scholar 

  2. M. H. Zainal-Abidin, M. Hayyan, A. Hayyan and N. S. Jayakumar, Anal. Chim. Acta, 979, 1 (2017).

    Article  CAS  PubMed  Google Scholar 

  3. A. Shishov, A. Bulatov, M. Locatelli, S. Carradori and V. Andruch, Microchem. J., 135, 33 (2017).

    Article  CAS  Google Scholar 

  4. M. Hadj-Kali, Green Process. Synth, 4, 117 (2015).

    CAS  Google Scholar 

  5. J. S. Lee, Nanotechnol. Rev., 6, 271 (2017).

    Article  CAS  Google Scholar 

  6. R. J. Isaifan and A. Amhamed, Adv. Chem., 2018, 1 (2018).

    Article  CAS  Google Scholar 

  7. R. M. Musale and S. R. Shukla, Int. J. Plast. Technol., 20, 106 (2016).

    Article  CAS  Google Scholar 

  8. U. B. Patil, A. S. Singh and J. M. Nagarkar, RSC Adv., 4, 1102 (2014).

    Article  CAS  Google Scholar 

  9. L. Wang, M. Zhou, Q. Chen and M.-Y. He, J. Chem. Res., 37, 598 (2013).

    Article  CAS  Google Scholar 

  10. P. H. Tran, H. T. Nguyen, P. E. Hansen and T. N. Le, RSC Adv., 6, 37031 (2016).

    Article  CAS  Google Scholar 

  11. V. De Santi, F. Cardellini, L. Brinchi and R. Germani, Tetrahedron Lett., 53, 5151 (2012).

    Article  CAS  Google Scholar 

  12. D. Mondal, M. Sharma, C.-H. Wang, Y.-C. Lin, H.-C. Huang, A. Saha, S. K. Nataraj and K. Prasad, Green Chem., 18, 2819 (2016).

    Article  CAS  Google Scholar 

  13. B. Singh, H. Lobo and G. Shankarling, Catal. Lett., 141, 178 (2011).

    Article  CAS  Google Scholar 

  14. F. Keshavarzipour and H. Tavakol, Catal. Lett., 145, 1062 (2015).

    Article  CAS  Google Scholar 

  15. S. Aparicio and R. Alcalde, Green Chem., 11, 65 (2009).

    Article  CAS  Google Scholar 

  16. C. S. M. Pereira, V. M. T. M. Silva and A. E. Rodrigues, Green Chem., 13, 2658 (2011).

    Article  CAS  Google Scholar 

  17. K. Tanaka, R. Yoshikawa, C. Ying, H. Kita and K. I. Okamoto, Chem. Eng. Sci., 57, 1577 (2002).

    Article  CAS  Google Scholar 

  18. E. W. Flick, Industrial Solvents Handbook, New Jersey, Noyes Data Corporation (1985).

    Google Scholar 

  19. J. S. Bennett, K. L. Charles, M. R. Miner, C. F. Heuberger, E. J. Spina, M. F. Bartels and T. Foreman, Green Chem., 11, 166 (2009).

    Article  CAS  Google Scholar 

  20. J. Lilja, J. Aumo, T. Salmi, D. Y. Murzin, P. Mäki-Arvela, M. Sundell, K. Ekman, R. Peltonen and H. Vainio, Appl. Catal. A Gen., 228, 253 (2002).

    Article  CAS  Google Scholar 

  21. K. Wasewar, S. Patidar and V. K. Agarwal, Desalination, 243, 305 (2009).

    Article  CAS  Google Scholar 

  22. S. Hasegawa, M. Azuma and K. Takahashi, J. Chem. Technol. Biotechnol., 83, 1503 (2008).

    Article  CAS  Google Scholar 

  23. H. Zhihong, G. Jing, Z. Tiantao, L. Weijie, Z. Liya and H. Ying, 3rd Int. Conf. Bioinforma. Biomed. Eng. iCBBE 2009, 1 (2009).

  24. J. Sun, Y. Jiang, L. Zhou and J. Gao, Biocatal. Biotransform., 28, 279 (2010).

    Article  CAS  Google Scholar 

  25. M. Koutinas, C. Yiangou, N. M. Osório, K. Ioannou, A. Canet, F. Valero and S. Ferreira-Dias, Bioresour. Technol., 247, 496 (2018).

    Article  CAS  PubMed  Google Scholar 

  26. N. Asthana, A. Kolah, D. T. Vu, C. T. Lira and D. J. Miller, Org. Process Res. Dev., 9, 599 (2005).

    Article  CAS  Google Scholar 

  27. J. Gao, X. M. Zhao, L. Y. Zhou and Z. H. Huang, Chem. Eng. Res. Des., 85, 525 (2007).

    Article  CAS  Google Scholar 

  28. P. Delgado, M. T. Sanz, S. Beltrán and L. A. Nunez Chem. Eng. J., 165, 693 (2010).

    Article  CAS  Google Scholar 

  29. F. U. Nigiz and N. D. Hilmioglu, React. Kinet. Mech. Catal., 118, 557 (2016).

    Article  CAS  Google Scholar 

  30. R. Pal, T. Sarkar and S. Khasnobis, Arkivoc, 2012, 570 (2012).

    Article  Google Scholar 

  31. I. J. Dijs, H. L. F. van Ochten, A. J. M. van der Heijden, J. W. Geus and L. W. Jenneskens, Appl. Catal. A Gen., 241, 185 (2003).

    Article  CAS  Google Scholar 

  32. G. Sampath and S. Kannan, Catal. Commun., 37, 41 (2013).

    Article  CAS  Google Scholar 

  33. Y. Dai, J. van Spronsen, G. J. Witkamp, R. Verpoorte and Y. H. Choi, Anal. Chim. Acta, 766, 61 (2013).

    Article  CAS  PubMed  Google Scholar 

  34. Y. L. Loow, E. K. New, G. H. Yang, L. Y. Ang, L. Y. W. Foo and T. Y.. Wu, Cellulose, 24, 3591 (2017).

    Article  CAS  Google Scholar 

  35. I. M. Aroso, A. Paiva, R. L. Reis and A. R. C. Duarte, J. Mol. Liq., 241, 654 (2017).

    Article  CAS  Google Scholar 

  36. K. Shahbaz, F. S. Mjalli, M. A. Hashim and I. M. Al Nashef, J. Appl. Sci., 10, 3349 (2010).

    Article  CAS  Google Scholar 

  37. Q. Wen, J. X. Chen, Y. L. Tang, J. Wang and Z. Yang, Chemosphere, 132, 63 (2015).

    Article  CAS  PubMed  Google Scholar 

  38. A. P. Abbott, R. C. Harris, K. S. Ryder, C. D’Agostino, L. F. Gladden and M. D. Mantle, Green Chem., 13, 82 (2011).

    Article  CAS  Google Scholar 

  39. C. D’Agostino, R. C. Harris, A. P. Abbott, L. F. Gladden and M. D. Mantle, Phys. Chem. Chem. Phys., 13, 21383 (2011).

    Article  PubMed  CAS  Google Scholar 

  40. G. Garda, S. Aparicio, R. Ullah and M. Atilhan, Energy Fuels, 29, 2616 (2015).

    Article  CAS  Google Scholar 

  41. A. Hayyan, M. Ali Hashim, F. S. Mjalli, M. Hayyan and I. M. AlNashef, Chem. Eng. Sci., 92, 81 (2013).

    Article  CAS  Google Scholar 

  42. B. Y. Zhao, P. Xu, F. X. Yang, H. Wu, M. H. Zong and W. Y. Lou, ACS Sustain. Chem. Eng., 3, 2746 (2015).

    Article  CAS  Google Scholar 

  43. L. S. Longo Jr. and M. V. Craveiro, J. Braz. Chem. Soc., 29, 1999 (2018).

    Google Scholar 

  44. R. Craveiro, I. Aroso, V. Flammia, T. Carvalho, M. T. Viciosa, M. Dionisio, S. Barreiros, R. L. Reis, A. R. C. Duarte and A. Paiva, J. Mol. Liq., 215, 534 (2016).

    Article  CAS  Google Scholar 

  45. Y. Marcus, in Deep Eutectic Solvents, Springer International Publishing, 45 (2019).

  46. A. Hayyan, F. S. Mjalli, I. M. Alnashef, T. Al-Wahaibi, Y. M. Al-Wahaibi and M. A. Hashim, Thermochim. Acta, 541, 70 (2012).

    Article  CAS  Google Scholar 

  47. Y. R. Lee, Y. J. Lee, W. Ma and K. H. Row, Korean J. Chem. Eng., 33, 2337 (2016).

    Article  CAS  Google Scholar 

  48. M. B. Taysun, E. Sert and F. S. Atalay, J. Chem. Eng. Data, 62, 1173 (2017).

    Article  CAS  Google Scholar 

  49. S. T. Williamson, K. Shahbaz, F. S. Mjalli, I. M. AlNashef and M. M. Farid, Renew. Energy, 114, 480 (2017).

    Article  CAS  Google Scholar 

  50. J. Cao, B. Qi, J. Liu, Y. Shang, H. Liu, W. Wang, J. Lv, Z. Chen, H. Zhang and X. Zhou, RSC Adv., 6, 21612 (2016).

    Article  CAS  Google Scholar 

  51. M. Zuo, K. Le, Y. Feng, C. Xiong, Z. Li, X. Zeng, X. Tang, Y. Sun and L. Lin, Ind. Crops Prod., 112, 18 (2018).

    Article  CAS  Google Scholar 

  52. Y. Hu, N. Li, G. Li, A. Wang, Y. Cong, X. Wang and T. Zhang, Green Chem., 19, 1663 (2017).

    Article  CAS  Google Scholar 

  53. Y. Pan, M. A. Alam, Z. Wang, J. Wu, Y. Zhang and Z. Yuan, Bioresour. Technol., 220, 543 (2016).

    Article  CAS  PubMed  Google Scholar 

  54. X. Zhang, Y. Zhao, S. Xu, Y. Yang, J. Liu, Y. Wei and Q. Yang, Nat. Commun., 5, 1 (2014).

    Google Scholar 

  55. N. Azizi and S. Dezfooli, Environ. Chem. Lett., 14, 201 (2016).

    Article  CAS  Google Scholar 

  56. D.-Y. Dai, L. Wang, Q. Chen and M.-Y. He, J. Chem. Res., 38, 183 (2014).

    Article  CAS  Google Scholar 

  57. D. A. Alonso, A. Baeza, R. Chinchilla, G. Guillena, I. M. Pastor and D. J. Ramón, Eur. J. Org. Chem., 2016, 612 (2016).

    Article  CAS  Google Scholar 

  58. B. S. Singh, H. R. Lobo, D. V. Pinjari, K. J. Jarag, A. B. Pandit and G. S. Shankarling, Ultrason. Sonochem., 20, 287 (2013).

    Article  CAS  PubMed  Google Scholar 

  59. J. T. Gorke, F. Srienc and R. J. Kazlauskas, in Ionic Liquid Applications: Pharmaceuticals, Therapeutics, and Biotechnology, Edited by S. V. Malhotra, ACS Publications, 169 (2010).

  60. E. Durand, J. Lecomte, B. Baréa, G. Piombo, E. Dubreucq and P. Villeneuve, Process Biochem., 47, 2081 (2012).

    Article  CAS  Google Scholar 

  61. R. Stefanovic, M. Ludwig, G. B. Webber, R. Atkin and A. J. Page, Phys. Chem. Chem. Phys., 19, 3297 (2017).

    Article  CAS  PubMed  Google Scholar 

  62. A. E. Ünlü, B. Prasad, K. Anavekar, P. Bubenheim and A. Liese, Prep. Biochem. Biotechnol, 47, 918 (2017).

    Article  CAS  Google Scholar 

  63. J. E. Bailey and D. F. Ollis, Biochemical Engineering Fundamentals, New York, McGraw Hill College (1986).

    Google Scholar 

  64. H. Scott Fogler, Elements of Chemical Reaction Engineering, Prentice Hall (2004).

  65. A. Takagaki, Catal. Sci. Technol., 6, 791 (2016).

    Article  CAS  Google Scholar 

  66. Sigma Aldrich, Webpage, (2019). at <https://www.sigmaaldrich.com/catalog/product/sial/216380?lang=en&region=TR>.

  67. G. Duan, C. B. B. Ching, E. Lim and C. H. H. Ang, Biotechnol. Lett., 19, 1051 (1997).

    Article  CAS  Google Scholar 

  68. R. H. Perry and D. W. Green, Perry’s Chemical Engineers’ Handbook, McGraw Hill Education (2007).

  69. B. Yu, D. G. Bansal, J. Qu, X. Sun, H. Luo, S. Dai, P. J. Blau, B. G. Bunting, G. Mordukhovich and D. J. Smolenski, Wear, 289, 58 (2012).

    Article  CAS  Google Scholar 

  70. R. E. Mapless, Petroleum refinery process economics, Oklahoma, PennWell Corporation (2000).

    Google Scholar 

  71. J. A. Dean, Langes Handbook of Chemistry, 15th ed. (1999).

  72. A. I. Simion, C. G. Grigoraç, L. E. Bardaçu and A. Dabija, Food Environ. Saf., 11, 49 (2012).

    CAS  Google Scholar 

  73. P.M. Doran, Bioprocess engineering principles, Elsevier Science Limited (1995).

  74. P. Delgado, M. T. Sanz and S. Beltrán, Chem. Eng. J., 126, 111 (2007).

    Article  CAS  Google Scholar 

  75. Y. Zhang, L. Ma and J. Yang, React. Funct. Polym, 61, 101 (2004).

    Article  CAS  Google Scholar 

  76. D. A. G. Aranda, R. T. P. Santos, N. C. O. Tapanes, A. L. D. Ramos and O. A. C. Antunes, Catal. Lett., 122, 20 (2008).

    Article  CAS  Google Scholar 

  77. F. F. Roman, A. E. Ribeiro, A. Queiroz, G. G. Lenzi, E. S. Chaves and P. Brito, Fuel, 239, 1231 (2019).

    Article  CAS  Google Scholar 

  78. G. Fan, C. Liao, T. Fang, S. Luo and G. Song, Carbohydr. Polym., 112, 203 (2014).

    Article  CAS  PubMed  Google Scholar 

  79. L. M. T. Frija and C. A. M. Afonso, Tetrahedron, 68, 7414 (2012).

    Article  CAS  Google Scholar 

  80. A. Kumar, M. Dixit, S. P. Singh, R. Raghunandan, P. R. Maulik and A. Goel, Tetrahedron Lett., 50, 4335 (2009).

    Article  CAS  Google Scholar 

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Acknowledgements

The authors acknowledge the Scientific and Technological Research Council of Turkey (TÜBITAK) who started the studies on EL production in our laboratory by Project No: 117M884.

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Correspondence to Ayşe Ezgi Ünlü.

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Ünlü, A.E., Arikaya, A., Altundağ, A. et al. Remarkable effects of deep eutectic solvents on the esterification of lactic acid with ethanol over Amberlyst-15. Korean J. Chem. Eng. 37, 46–53 (2020). https://doi.org/10.1007/s11814-019-0385-9

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  • DOI: https://doi.org/10.1007/s11814-019-0385-9

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