Kinetic study on the reaction of palmitic acid with ethanol catalyzed by deep eutectic solvent based on dodecyl trimethyl ammonium chloride

Shan Jiang; Zuoxiang Zeng; Weilan Xue; Wei Zhang; Zhiyuan Zhou

Korean Journal of Chemical Engineering, Vol.37, No.9, 1482-1489, September, 2020

DOI10.1007/s11814-020-0557-7 Export Citation

Kinetic study on the reaction of palmitic acid with ethanol catalyzed by deep eutectic solvent based on dodecyl trimethyl ammonium chloride

Shan Jiang, Zuoxiang Zeng^†, Weilan Xue, Wei Zhang, and Zhiyuan Zhou

Institute of Chemical Engineering, East China University of Science and Technology, 200237 Shanghai, China

E-mail:

This study explored the direct esterification of palmitic acid and ethanol using a deep eutectic solvent (DES) as catalyst to produce biodiesel. Three novel deep eutectic solvents (DTAC-PTSA, DTAC-2PTSA, DTAC-3PTSA) were successfully prepared by mixing dodecyl trimethyl ammonium chloride (DTAC) and p-toluenesulfonic acid monohydrate (PTSA) in a molar ratio of 1: z (z=1, 2, 3). After testing, DTAC-3PTSA was found to have the best catalytic performance among the three types of DESs and was therefore selected as the catalyst for subsequent experiments. The effects of agitation speed, ethanol to palmitic acid molar ratio (α), temperature and catalyst dosage were studied by investigating the change of palmitic acid conversion rate with time under different conditions, respectively. Then, the pseudo-homogeneous (PH) model was utilized to describe the kinetic behavior of this reaction between 328.15-348.15 K and it was found to work well for the experimental data obtained. Moreover, the catalytic performance of DTAC-3PTSA was detected to have no significant change in the cycle test. Therefore, DTAC-3PTSA can be considered as a substitute for traditional catalysts to produce biodiesel and the kinetic data obtained here can be used for further up-scaling study.

Keywords:Deep Eutectic Solvent;Biodiesel;Ethyl Palmitate;Esterification;Kinetics

[References]

Rafael L, Jon CL, Bipasa D, Joy C, Juan MC, Antonio AR, Energy Environ. Sci., 3, 1706 (2010)
Renata SA, Leonardo ST, Fabio RR, Anal. Methods, 7, 4396 (2015)
Sazzad BS, Fazal MA, Haseeb AA, Masjuki HH, RSC Adv., 6, 60244 (2016)
Singh D, Sharma D, Soni SL, Sharma S, Kumari D, Fuel, 253, 60 (2019)
Adam FL, James AB, Jinesh CM, Karen W, Chem. Soc. Rev., 43, 7887 (2014)
Ana LL, Celia MR, Claudio JM, Catal. Sci. Technol., 6, 2877 (2016)
Lillah Z, Toh AN, Li Z, Green Chem., 16, 1202 (2014)
Juan AM, Jose I, Gabriel M, Green Chem., 11, 1285 (2009)
Pedro L, Juana MB, Eduardo GV, Gregorio SG, Michel V, Burguete MI, Santiago VL, Green Chem., 17, 3706 (2015)
Avinash GK, Prashant NM, Pundlik RB, RSC Adv., 6, 105087 (2016)
Su F, Guo Y, Green Chem., 16, 2934 (2014)
Lillah Z, Tan G, Li Z, Green Chem., 14, 3077 (2012)
Shibasaki-Kitakawa N, Hiromori K, Ihara T, Nakashima K, Yonemoto T, Fuel, 139, 11 (2015)
Liu P, Hao JW, Mo LP, Zhang ZH, RSC Adv., 5, 48675 (2015)
Chantamanee P, Noriaki S, Nut S, Tawatchai C, Hajime T, Green Chem., 16, 4936 (2014)
Siew HS, Kian FY, Keat TL, Bhatia S, Soon HT, RSC Adv., 3, 9070 (2013)
Zhang Q, Karine DV, Sebastien R, Francois J, Chem. Soc. Rev., 41, 7108 (2012)
Liu F, Karine DV, Marc PT, Yannick P, Clacens JM, Floryan D, Francois J, Green Chem., 15, 901 (2013)
Sunanda BP, Ganapati SS, Green Chem., 12, 458 (2010)
Hai TN, Phuong HT, RSC Adv., 6, 98365 (2016)
Cao J, Qi B, Liu J, Shang Y, Liu H, Wang W, Lv J, Chen Z, Zhang H, Zhou X, RSC Adv., 6, 21612 (2016)
Lee YR, Lee YJ, Ma W, Row KH, Korean J. Chem. Eng., 33(8), 2337 (2016)
Tran PH, Hang AT, RSC Adv., 8, 11127 (2018)
Gu L, Huang W, Tang SK, Tian SJ, Zhang XW, Chem. Eng. J., 259, 647 (2015)
Swapnendu C, Sourav B, Rajat C, RSC Adv., 6, 74278 (2016)
Michael PH, Amrit V, Scott LC, Julie LC, Joseph WL, Eric JM, Aaron JR, Phys. Chem. Chem. Phys., 19, 28153 (2017)
Marek T, Stefan T, Vasil S, Jacek N, Green Chem., 15, 1615 (2013)
Sergey PV, Andreas H, J. Chem. Soc., 2, 728 (2002)
Fredenslund A, Rasmussen P, AIChE J., 25(1), 203 (1979)
Reid C, Prausnitz JM, The properties of gases and liquids, McGraw-Hill, New York (1987).
Fredenslund A, Russell LJ, Prausnitz JM, AIChE J., 21(6), 1086 (1975)
Barrie PJ, Phys. Chem. Chem. Phys., 14, 318 (2012)

[Referenced By]

[1] Rafael L, Jon CL, Bipasa D, Joy C, Juan MC, Antonio AR, Energy Environ. Sci., 3, 1706 (2010)

[2] Renata SA, Leonardo ST, Fabio RR, Anal. Methods, 7, 4396 (2015)

[3] Sazzad BS, Fazal MA, Haseeb AA, Masjuki HH, RSC Adv., 6, 60244 (2016)

[4] Singh D, Sharma D, Soni SL, Sharma S, Kumari D, Fuel, 253, 60 (2019)

[5] Adam FL, James AB, Jinesh CM, Karen W, Chem. Soc. Rev., 43, 7887 (2014)

[6] Ana LL, Celia MR, Claudio JM, Catal. Sci. Technol., 6, 2877 (2016)

[7] Lillah Z, Toh AN, Li Z, Green Chem., 16, 1202 (2014)

[8] Juan AM, Jose I, Gabriel M, Green Chem., 11, 1285 (2009)

[9] Pedro L, Juana MB, Eduardo GV, Gregorio SG, Michel V, Burguete MI, Santiago VL, Green Chem., 17, 3706 (2015)

[10] Avinash GK, Prashant NM, Pundlik RB, RSC Adv., 6, 105087 (2016)

[11] Su F, Guo Y, Green Chem., 16, 2934 (2014)

[12] Lillah Z, Tan G, Li Z, Green Chem., 14, 3077 (2012)

[13] Shibasaki-Kitakawa N, Hiromori K, Ihara T, Nakashima K, Yonemoto T, Fuel, 139, 11 (2015)

[14] Liu P, Hao JW, Mo LP, Zhang ZH, RSC Adv., 5, 48675 (2015)

[15] Chantamanee P, Noriaki S, Nut S, Tawatchai C, Hajime T, Green Chem., 16, 4936 (2014)

[16] Siew HS, Kian FY, Keat TL, Bhatia S, Soon HT, RSC Adv., 3, 9070 (2013)

[17] Zhang Q, Karine DV, Sebastien R, Francois J, Chem. Soc. Rev., 41, 7108 (2012)

[18] Liu F, Karine DV, Marc PT, Yannick P, Clacens JM, Floryan D, Francois J, Green Chem., 15, 901 (2013)

[19] Sunanda BP, Ganapati SS, Green Chem., 12, 458 (2010)

[20] Hai TN, Phuong HT, RSC Adv., 6, 98365 (2016)

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

[22] Lee YR, Lee YJ, Ma W, Row KH, Korean J. Chem. Eng., 33(8), 2337 (2016)

[23] Tran PH, Hang AT, RSC Adv., 8, 11127 (2018)

[24] Gu L, Huang W, Tang SK, Tian SJ, Zhang XW, Chem. Eng. J., 259, 647 (2015)

[25] Swapnendu C, Sourav B, Rajat C, RSC Adv., 6, 74278 (2016)

[26] Michael PH, Amrit V, Scott LC, Julie LC, Joseph WL, Eric JM, Aaron JR, Phys. Chem. Chem. Phys., 19, 28153 (2017)

[27] Marek T, Stefan T, Vasil S, Jacek N, Green Chem., 15, 1615 (2013)

[28] Sergey PV, Andreas H, J. Chem. Soc., 2, 728 (2002)

[29] Fredenslund A, Rasmussen P, AIChE J., 25(1), 203 (1979)

[30] Reid C, Prausnitz JM, The properties of gases and liquids, McGraw-Hill, New York (1987).

[31] Fredenslund A, Russell LJ, Prausnitz JM, AIChE J., 21(6), 1086 (1975)

[32] Barrie PJ, Phys. Chem. Chem. Phys., 14, 318 (2012)