Yaoyao Feng1, Ting Qiu1, Jinbei Yang1,2, Ling Li1, Xiaoda Wang1, Hongxing Wang1
Yaoyao Feng1, Ting Qiu1, Jinbei Yang1,2, Ling Li1, Xiaoda Wang1, Hongxing Wang1
摘要： The transesterification of palm oil and methanol catalyzed by Brønsted acidic ionic liquids was investigated. Four eco-friendly Brønsted acidic ionic liquids were prepared and their structures were characterized by NMR, FT-IR and TG-DTG. The results demonstrated that[CyN1,1 PrSO3H] [p-TSA] was more efficient than the other ionic liquids and chosen as catalyst for further research. The influences of various reaction parameters on the conversion of palm oil to biodiesel were performed, and the orthogonal test was investigated to seek the optimum reaction conditions, which were illustrated as follows:methanol to oil mole ratio of 24:1, catalyst dosage of 3.0 wt% of oil, reaction temperature of 120℃, reaction time of 150 min, and the biodiesel yield achieved 98.4%. In addition, kinetic study was established for the conversion process, with activation energy and preexponential factor of 122.93 kJ·mol-1 and 1.83×1015, respectively. Meanwhile, seven-time recycling runs of ionic liquid were completed with ignorable loss of its catalyst activity. The refined biodiesel met the biodiesel standard EN 14214.
|  O.E. Ajala, F. Aberuagba, T.E. Odetoye, A.M. Ajala, Biodiesel:sustainable energy replacement to petroleum-based diesel fuel-A review, ChemBioEng. Rev. 2(2015) 145-156.
 F.R. Ma, M.A. Hanna, Biodiesel production:A review, Bioresour. Technol. 70(1999) 1-15.
 J.Y. Yong, J.J. Klemes, P.S. Varbanov, D. Huisingh, Cleaner energy for cleaner production:Modelling, simulation, optimisation and waste management, J. Clean. Prod. 111(2016) 1-16.
 S. Ramkumar, V. Kirubakaran, Biodiesel from vegetable oil as alternate fuel for C.I engine and feasibility study of thermal cracking:A critical review, Energy Convers. Manag. 118(2016) 155-169.
 J.M. Bergthorson, M.J. Thomson, A review of the combustion and emissions properties of advanced transportation biofuels and their impact on existing and future engines, Renew. Sust. Energ. Rev. 42(2015) 1393-1417.
 N.L. Panwar, S.C. Kaushik, S. Kothari, Role of renewable energy sources in environmental protection:A review, Renew. Sust. Energ. Rev. 15(2011) 1513-1524.
 D.Y.C. Leung, X. Wu, M.K.H. Leung, A review on biodiesel production using catalyzed transesterification, Appl. Energy 87(2010) 1083-1095.
 M.R. Anuar, A.Z. Abdullah, Challenges in biodiesel industry with regards to feedstock, environmental, social and sustainability issues:A critical review, Renew. Sust. Energ. Rev. 58(2016) 208-223.
 C.Y. Yang, Z. Fang, B. Li, Y.F. Long, Review and prospects of Jatropha biodiesel industry in China, Renew. Sust. Energ. Rev. 16(2012) 2178-2190.
 J.C. Kurnia, S.V. Jangam, S. Akhtar, A.P. Sasmito, A.S. Mujumdar, Advances in biofuel production from oil palm and palm oil processing wastes:A review, Biofuel Res. J. 3(2016) 332-346.
 H.C. Ong, T.M.I. Mahlia, H.H. Masjuki, R.S. Norhasyima, Comparison of palm oil, Jatropha curcas and Calophyllum inophyllum for biodiesel:A review, Renew. Sust. Energ. Rev. 15(2011) 3501-3515.
 Y. Syamsuddin, M.N. Murat, B.H. Hameed, Synthesis of fatty acid methyl ester from the transesterification of high-and low-acid-content crude palm oil (Elaeis guineensis) and karanj oil (Pongamia pinnata) over a calcium-lanthanum-aluminum mixedoxides catalyst, Bioresour. Technol. 214(2016) 248-252.
 E. Lotero, Y.J. Liu, D.E. Lopez, K. Suwannakarn, D.A. Bruce, J.G. Goodwin, Synthesis of biodiesel via acid catalysis, Ind. Eng. Chem. Res. 44(2005) 5353-5363.
 M. Tubino, J.G. Rocha, G.F. Bauerfeldt, Biodiesel synthesis:A study of the triglyceride methanolysis reaction with alkaline catalysts, Catal. Commun. 75(2016) 6-12.
 J.M. Dias, M.C.M. Alvim-Ferraz, M.F. Almeida, Comparison of the performance of different homogeneous alkali catalysts during transesterification of waste and virgin oils and evaluation of biodiesel quality, Fuel 87(2008) 3572-3578.
 K.G. Georgogianni, M.G. Kontominas, P.J. Pomonis, D. Avlonitis, V. Gergis, Conventional and in situ transesterification of sunflower seed oil for the production of biodiesel, Fuel Process. Technol. 89(2008) 503-509.
 L. Wu, T.Y. Wei, Z.F. Tong, Y. Zou, Z.J. Lin, J.H. Sun, Bentonite-enhanced biodiesel production by NaOH-catalyzed transesterification of soybean oil with methanol, Fuel Process. Technol. 144(2016) 334-340.
 T.T.V. Tran, S. Kaiprommarat, S. Kongparakul, P. Reubroycharoen, G.Q. Guan, M.H. Nguyen, C. Samart, Green biodiesel production from waste cooking oil using an environmentally benign acid catalyst, Waste Manag. 52(2016) 367-374.
 Y.Y. Liu, H.F. Lu, W. Jiang, D.S. Li, S.J. Liu, B. Liang, Biodiesel production from crude Jatropha curcas L. oil with trace acid catalyst, Chin. J. Chem. Eng. 20(2012) 740-746.
 M.R.W. Moussavou, C. Brunschwig, B. Barea, P. Villeneuve, J. Blin, Assessing the enzyme activity of different plant extracts of biomasses from sub-Saharan Africa for ethyl biodiesel production, Energy Fuel 30(2016) 2356-2364.
 P.M. Nielsen, J. Brask, L. Fjerbaek, Enzymatic biodiesel production:Technical and economical considerations, Eur. J. Lipid Sci. Technol. 110(2008) 692-700.
 R.C. Rodrigues, G. Volpato, K. Wada, M.A.Z. Ayub, Enzymatic synthesis of biodiesel from transesterification reactions of vegetable oils and short chain alcohols, J. Am. Oil Chem. Soc. 85(2008) 925-930.
 A.S. Amarasekara, Acidic ionic liquids, Chem. Rev. 116(2016) 6133-6183.
 J.C. Kuschnerow, K. Titze-Frech, P.S. Schulz, P. Wasserscheid, S. Scholl, Continuous transesterification with acidic ionic liquids as homogeneous catalysts, Chem. Eng. Technol. 36(2013) 1643-1650.
 J. Li, X. Peng, M. Luo, C.J. Zhao, C.B. Gu, Y.G. Zu, Y.J. Fu, Biodiesel production from Camptotheca acuminata seed oil catalyzed by novel Brønsted-Lewis acidic ionic liquid, Appl. Energy 115(2014) 438-444.
 T. Welton, Ionic liquids in catalysis, Coord. Chem. Rev. 248(2004) 2459-2477.
 N. Muhammad, Y.A. Elsheikh, M.I.A. Mutalib, A.A. Bazmi, R.A. Khan, H. Khan, S. Rafiq, Z. Man, I. Khan, An overview of the role of ionic liquids in biodiesel reactions, J. Ind. Eng. Chem. 21(2015) 1-10.
 M. Vafaeezadeh, H. Alinezhad, Brønsted acidic ionic liquids:Green catalysts for essential organic reactions, J. Mol. Liq. 218(2016) 95-105.
 T. Qiu, W.L. Tang, C.G. Li, C.M. Wu, L. Li, Reaction kinetics for synthesis of sec-butyl alcohol catalyzed by acid-functionalized ionic liquid, Chin. J. Chem. Eng. 23(2015) 106-111.
 H.X. Wang, C.M. Wu, X.W. Bu, W.L. Tang, Q. Ting, A benign preparation of secbutanol via transesterification from sec-butyl acetate using the acidic Imidazolium ionic liquids as catalysts, Chem. Eng. J. 246(2014) 366-372.
 J.B. Yang, L.H. Zhou, X.T. Guo, L. Li, P. Zhang, R.Y. Hong, T. Qiu, Study on the esterification for ethylene glycol diacetate using supported ionic liquids as catalyst:Catalysts preparation, characterization, and reaction kinetics, process, Chem. Eng. J. 280(2015) 147-157.
 T. Qiu, X.T. Guo, J.B. Yang, L.H. Zhou, L. Li, H.X. Wang, Y. Niu, The synthesis of biodiesel from coconut oil using novel Brønsted acidic ionic liquid as green catalyst, Chem. Eng. J. 296(2016) 71-78.
 M.L. Pisarello, B.O. Dalla Costa, N.S. Veizaga, C.A. Querini, Volumetric method for free and total glycerin determination in biodiesel, Ind. Eng. Chem. Res. 49(2010) 8935-8941.
 M. Olkiewicz, N.V. Plechkova, M.J. Earle, A. Fabregat, F. Stüber, A. Fortuny, J. Font, C. Bengoa, Biodiesel production from sewage sludge lipids catalysed by Brønsted acidic ionic liquids, Appl. Catal. B Environ. 181(2016) 738-746.
 L. Zhang, M. Xian, Y.C. He, L.Z. Li, J.M. Yang, S.T. Yu, X. Xu, A Brønsted acidic ionic liquid as an efficient and environmentally benign catalyst for biodiesel synthesis from free fatty acids and alcohols, Bioresour. Technol. 100(2009) 4368-4373.
 B. Aghabarari, N. Dorostkar, M.V. Martinez-Huerta, Synthesis of biodiesel from Nigella sativa seed oil using surfactant-Brønsted acidic-combined ionic liquid as catalyst, Fuel Process. Technol. 118(2014) 296-301.
 A.H.M. Fauzi, N.A.S. Amin, Optimization of oleic acid esterification catalyzed by ionic liquid for green biodiesel synthesis, Energy Convers. Manag. 76(2013) 818-827.
 X. Wu, D.Y. Leung, Optimization of biodiesel production from camelina oil using orthogonal experiment, Appl. Energy 88(2011) 3615-3624.
 P.K.K.S. Heer, D.D. Chabukswar, V.G. Gaikar, Intrinsic kinetics of esterification of fatty acids catalyzed by supported ionic liquid catalysts, Chem. Eng. Technol. 38(2015) 1416-1424.
 K. Li, Z. Yang, J. Zhao, J. Lei, X. Jia, S.H. Mushrif, Y. Yang, Mechanistic and kinetic studies on biodiesel production catalyzed by an efficient pyridinium based ionic liquid, Green Chem. 17(2015) 4271-4280.
 A.H. Mohammad Fauzi, N.A.S. Amin, R. Mat, Esterification of oleic acid to biodiesel using magnetic ionic liquid:Multi-objective optimization and kinetic study, Appl. Energy 114(2014) 809-818.
 G.D. Yadav, A.R. Yadav, Synthesis of ethyl levulinate as fuel additives using heterogeneous solid superacidic catalysts:Efficacy and kinetic modeling, Chem. Eng. J. 243(2014) 556-563.
 Y. Li, S. Hu, J. Cheng, W. Lou, Acidic ionic liquid-catalyzed esterification of oleic acid for biodiesel synthesis, Chin. J. Catal. 35(2014) 396-406.
 M. Han, W. Yi, Q. Wu, Y. Liu, Y. Hong, D. Wang, Preparation of biodiesel from waste oils catalyzed by a Brønsted acidic ionic liquid, Bioresour. Technol. 100(2009) 2308-2310.
 M. Ghiaci, B. Aghabarari, S. Habibollahi, A. Gil, Highly efficient Brønsted acidic ionic liquid-based catalysts for biodiesel synthesis from vegetable oils, Bioresour. Technol. 102(2011) 1200-1204.
|||Xiaomei Wang, Chun Li, Hairong Yue, Shaojun Yuan, Changjun Liu, Siyang Tang, Bin Liang . Effects of mechanical activation on the digestion of ilmenite in dilute H2SO4[J]. Chinese Journal of Chemical Engineering, 2019, 27(3): 575-586.|
|||Miljana S. Marković, Svetomir Ž. Milojević, Nevenka M. Bošković-Vragolović, Vladimir P. Pavićević, Ljiljana М. Babincev, Vlada B. Veljković. A new kinetic model for the common juniper essenstial oil extraction by microwave hydrodistillation[J]. Chinese Journal of Chemical Engineering, 2019, 27(3): 605-612.|
|||Barış Şimşek. TOPSIS based Taguchi design optimization for CVD growth of graphene using different carbon sources: Graphene thickness, defectiveness and homogeneity[J]. Chinese Journal of Chemical Engineering, 2019, 27(3): 685-694.|
|||Yong Liu, Guodong Wang, Lu Wang, Xianlong Li, Qiong Luo, Ping Na. Zeolite P synthesis based on fly ash and its removal of Cu(Ⅱ) and Ni (Ⅱ) ions[J]. Chinese Journal of Chemical Engineering, 2019, 27(2): 341-348.|
|||Miao Liu, Zhengming Gao, Yongjiu Yu, Zhipeng Li, Jing Han, Ziqi Cai, Xiongbing Huang. PIV experiment and large eddy simulation of turbulence characteristics in a confined impinging jet reactor[J]. Chinese Journal of Chemical Engineering, 2019, 27(1): 10-20.|
|||Aju Mathew George, Ajay R. Tembhurkar. Analysis of equilibrium, kinetic, and thermodynamic parameters for biosorption of fluoride from water onto coconut (Cocos nucifera Linn.) root developed adsorbent[J]. Chinese Journal of Chemical Engineering, 2019, 27(1): 92-99.|
|||Mohd Nasrullah, A. W. Zularisam, Santhana Krishnan, Mimi Sakinah, Lakhveer Singh, Yap Wing Fen. High performance electrocoagulation process in treating palm oil mill effluent using high current intensity application[J]. Chinese Journal of Chemical Engineering, 2019, 27(1): 208-217.|
|||Ying Qing, Houfang Lu, Yingying Liu, Changjun Liu, Bin Liang, Wei Jiang. Production of glycerol carbonate using crude glycerol from biodiesel production with DBU as a catalyst[J]. Chinese Journal of Chemical Engineering, 2018, 26(9): 1912-1919.|
|||Baohe Wang, Baomin Ge, Jing Zhu, Lina Wang. Process optimization study on the carbonylation of methyl acetate[J]. Chinese Journal of Chemical Engineering, 2018, 26(9): 1937-1942.|
|||Ze Dong, Liping Chen, Yingying Ma, Haoliang Peng, Wanghua Chen. Adiabatic correction for the esterification of acetic anhydride by methanol via accurate kinetics[J]. Chinese Journal of Chemical Engineering, 2018, 26(9): 1954-1959.|
|||Xiuhui Huang, Zeqiu Li, Ying Tian. Process optimization of an industrial acetic acid dehydration progress via heterogeneous azeotropic distillation[J]. Chinese Journal of Chemical Engineering, 2018, 26(8): 1631-1643.|
|||Yu Li, Tong Qiu. Logarithm-transform piecewise linearization method for the optimization of fasoline blending processes[J]. Chinese Journal of Chemical Engineering, 2018, 26(8): 1684-1691.|
|||Ying Chen, Zhihong Yuan, Bingzhen Chen. Process optimization with consideration of uncertainties-An overview[J]. Chinese Journal of Chemical Engineering, 2018, 26(8): 1700-1706.|
|||Chonglin Zhong, Yi Zheng, Shenghu Xu, Shaoyuan Li. Enhanced exergy cost optimization of operating conditions in FCCU main fractionator[J]. Chinese Journal of Chemical Engineering, 2018, 26(8): 1750-1757.|
|||Yulei Ge, Shurong Li, Xiaodong Zhang. Optimization for ASP flooding based on adaptive rationalized Haar function approximation[J]. Chinese Journal of Chemical Engineering, 2018, 26(8): 1758-1765.|