Temperature-responsive self-separation ionic liquid system of zwitterionic-type quaternary ammonium-KI for CO2 fixation

doi:10.1016/S1872-2067(18)63101-8

Abstract

Abstract:

A series of zwitterionic-type quaternary ammoniums (ZTQAs) with varying lengths of alkyl chains combined with KI were synthesized and considered as catalysts for the coupling reaction of CO₂ and various terminal epoxides. The prolonged alkyl chain of ZTQAs exhibited temperature-responsive self-separation in propylene carbonate (PC). The interaction between ZTQAs and KI was confirmed by X-ray photoelectron spectroscopy and quantum chemical calculations. This interaction strengthened the nucleophilicity of the I^- ion, favoring the catalytic reaction. The 3-(dimethyltetradecylammonium) propane sulfonate (DTPS)/KI showed an excellent yield of PC (95.1%) at 125℃, 1.5 MPa, and 1 mol% loading of catalyst. The precipitate formed spontaneously from the catalytic system, providing high catalytic activity of the homogeneous catalyst, as well as easy recovery of the heterogeneous catalyst.

Key words: Carbon dioxide, Self-separation, Cyclic carbonate, Zwitterionic-type quaternary ammonium, KI

Xiying Fu, Pengtao Xie, Yiwei Lian, Leqin He, Wei Zhao, Tao Chang, Shenjun Qin. Temperature-responsive self-separation ionic liquid system of zwitterionic-type quaternary ammonium-KI for CO₂ fixation[J]. Chinese Journal of Catalysis, 2018, 39(11): 1854-1860.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(18)63101-8

https://www.cjcatal.com/EN/Y2018/V39/I11/1854

References

[1] M. Alves, B. Grignard, R. Mereau, C. Jerome, T. Tassaing, C. Detrembleur, Catal. Sci. Technol., 2017, 7, 2651-2684.
[2] Q. W. Song, Z. H. Zhou, L. N. He, Green Chem., 2017, 19, 3707-3728.
[3] J. Artz, T. E. Müller, K. Thenert, J. Kleinekorte, R. Meys, A. Sternberg, A. Bardow, W. Leitner, Chem. Rev., 2018, 118, 434-504.
[4] M. Aresta, A. Dibenedetto, A. Angelini, Chem. Rev., 2014, 114, 1709-1742.
[5] X. B. Lu, D. J. Darensbourg, Chem. Soc. Rev., 2012, 41, 1462-1484.
[6] F. D. Meylan, V. Moreau, S. Erkman, J. CO₂ Util., 2015, 12, 101-108.
[7] G. Q. Yuan, C. R. Qi, W. Q. Wu, H. F. Jiang, Curr. Opin. Green Sustain. Chem., 2017, 3, 22-27.
[8] H. Arakawa, M. Aresta, J. N. Armor, J. N. Armor, M. A. Barteau, E. J. Beckman, A. T. Bell, J. E. Bercaw, C. Creutz, E. Dinjus, D. A. Dixon, K. Domen, D. L. DuBois, J. Eckert, E. Fujita, D. H. Gibson, W. A. Goddard, D. W. Goodman, J. Keller, G. J. Kubas, H. H. Kung, J. E. Lyons, L. E. Manzer, T. J. Marks, K. Morokuma, K. M. Nicholas, R. Periana, L. Que, J. Rostrup-Nielson, W. M. H. Sachtler, L. D. Schmidt, A. Sen, G. A. Somorjai, P. C. Stair, B. R. Stults, W. Tumas, Chem. Rev., 2001, 101, 953-996.
[9] P. P. Pescarmona, M. Taherimehr, Catal. Sci. Technol., 2012, 2, 2169-2187.
[10] B. H. Xu, J. Q. Wang, J. Sun, Y. Huang, J. P. Zhang, X. P. Zhang, S. J. Zhang, Green Chem., 2015, 17, 108-122.
[11] C. Martín, G. Fiorani, A. W. Kleij, ACS Catal., 2015, 5, 1353-1370.
[12] J. M. Comerford, Ian D. V. Ingram, M. North, X. Wu, Green Chem., 2015, 17, 1966-1987.
[13] D. W. Kim, R. Roshan, J. Tharun, A. Cherian, D.W. Park, Korean J. Chem. Eng., 2013, 30, 1973-1984.
[14] M. Mikkelsen, M. Jørgensen, F. C. Krebs, Energy Environ. Sci., 2010, 3, 43-81.
[15] Q. Li, J. Chen, L. Fan, X. Q. Kong, Y. Y. Lu, Green Energy Environ., 2016, 1, 18-42.
[16] B. Schäffner, F. Schäffner, S. P. Verevkin, A. Börner, Chem. Rev., 2010, 110, 4554-4581.
[17] P. Goodrich, H. Q. N. Gunaratne, J. Jacquemin, L. L. Jin, Y. T. Lei, K. R. Seddon, ACS Sustain. Chem. Eng., 2017, 5, 5635-5641.
[18] V. B. Saptal, B. M. Bhanage, ChemSusChem, 2016, 10, 1145-1151.
[19] L. Wang, K. Kodama, T. Hirose, Catal. Sci. Technol., 2016, 6, 3872-3877.
[20] M. Alves, B. Grignard, S. Gennen, R. Mereau, C. Detrembleur, C. Jerome, S. Tassaing, Catal. Sci. Technol., 2015, 5, 4636-4643.
[21] B. S. Wang, Z. J. Luo, E. H. M. Elageed, S. Wu, Y. Y. Zhang, X. P. Wu, F. Xia, G. R. Zhang, G. H. Gao, ChemCatChem, 2016, 8, 830-838.
[22] M. Adolph, T. A. Zevaco, C. Altesleben, S. Staudt, E. Dinjus, J. Mol. Catal. A, 2015, 400, 104-110.
[23] M. Taherimehr, J. P. C. C. Sertã, A. W. Kleij, C. J. Whiteoak, P. P. Pescarmona, ChemSusChem, 2015, 8, 1034-1042.
[24] T. Chang, L. L. Jin, H. W. Jing, ChemCatChem, 2009, 1, 379-383.
[25] C. Maeda, T. Taniguchi, K. Ogawa, T. Ema, Angew. Chem. Int. Ed., 2015, 54, 134-138.
[26] H. Büttner, K. Lau, A. Spannenberg, T. Werner, ChemCatChem, 2015, 7, 459-467.
[27] M. S. Liu, K. Q. Gao, L. Liang, F. X. Wang, L. Shi, J. M. Sun, Phys. Chem. Chem. Phys., 2015, 17, 5959-5965.
[28] T. Chang, X. R. Gao, L. Bian, X. Y. Fu, M. X. Yuan, H. W. Jing, Chin. J. Catal., 2015, 36, 408-413.
[29] M. S. Liu, B. Liu, S. F. Zhong, L. Shi, L. Liang, J. M. Sun, Ind. Eng. Chem. Res., 2015, 54, 633-640.
[30] R. C. Luo, X. T. Zhou, W. Y. Zhang, Z. X. Liang, J. Jiang, H. B. Ji, Green Chem., 2014, 16, 4179-4189.
[31] T. Werner, H. Büttner, ChemSusChem, 2014, 7, 3268-3271.
[32] A. M. Hardman-Baldwin, A. E. Mattson, ChemSusChem, 2014, 7, 3275-3278.
[33] A. J. Chen, C. Chen, Y. H. Xiu, X. R. Liu, J. Z. Chen, L. Guo, R. Zhang, Z. S. Hou, Green Chem., 2015, 17, 1842-1852.
[34] T. Ema, K. Fukuhara, T. Sakai, M. Ohbo, F. Q. Bai, J. Y. Hasegawa, Catal. Sci. Technol., 2015, 5, 2314-2321.
[35] M. H. Anthofer, M. E. Wilhelm, M. Cokoja, M. Drees, W. A. Herrmann, F. E. Kühn, ChemCatChem, 2015, 7, 94-98.
[36] S. Gennen, M. Alves, R. Méreau, T. Tassaing, B. Gilbert, C. Detrebleur, C. Jerome, B. Grignard, ChemSusChem, 2015, 8, 1845-1849.
[37] X. Y. Fu, X. Y. Jing, L. L. Jin, L. L. Zhang, X. F. Zhang, B. Hu, H. W. Jing, Chin. J. Catal., 2018, 39, 997-1003.
[38] X. Jiang, F. L. Gou, F. J. Chen, H. W. Jing, Green Chem., 2016, 18, 3567-3576.
[39] J. Steinbauer, L. Longwitz, M. Frank, J. Epping, U. Kragl, T. Werner, Green Chem., 2017, 19, 4435-4445.
[40] V. Besse, N. Illy, G. David, S. Caillol, B. Boutevin, ChemSusChem, 2016, 9, 2167-2173.
[41] S. Verma, R. I. Kureshy, T. Roy, M. Kumar, A. Das, N. H. Khan, S. H. R. Abdi, H. C. Bajaj, Catal. Commun., 2015, 61, 78-82.
[42] M. I. Kim, S. J. Choi, D. W. Kim, D. W. Park, J. Ind. Eng. Chem., 2014, 20, 3102-3107.
[43] L. C. Luo, X. T. Zhou, Y. X. Fang, H. B. Ji, Carbon, 2015, 82, 1-11.
[44] A. R. Hajipour, Y. Heidari, G. Kozehgary, RSC Adv., 2015, 5, 22373-22379.
[45] J. Sun, W. G. Cheng, Z. F. Yang, J. Q. Wang, T. T. Xu, J. Y. Xin, S. J. Zhang, Green Chem., 2014, 16, 3071-3078.
[46] J. Tharun, D. W. Kim, R. Roshan, Y. Hwang, D. W. Park, Catal. Commun., 2013, 31, 62-65.
[47] Y. Y. Zhang, S. F. Yin, S. L. Luo, C. T. Au, Ind. Eng. Chem. Res., 2012, 51, 3951-3957.
[48] J. Tharun, Y. Hwang, R. Roshan, S. Ahn, A. C. Kathalikkattil, D. W. Park, Catal. Sci. Technol., 2012, 2, 1674-1680.
[49] K. R. Roshan, G. Mathai, J. Kim, J. Tharun, G. A. Park, D. W. Park, Green Chem., 2012, 14, 2933-2940.
[50] M. S. Liu, B. Liu, L. Shi, F. X. Wang, L. Liang, J. M. Sun, RSC Adv., 2015, 5, 960-966.
[51] M. Sankar, T. G. Ajithkumar, G. Sankar, P. Manikandan, Catal. Commun., 2015, 59, 201-205.
[52] X. M. Yan, X. Ding, Y. Pan, X. W. Xu, C. Hao, W. J. Zheng, G. H. He, Chin. J. Catal., 2017, 38, 862-871.
[53] S. Jayakumar, H. Li, Y. P. Zhao, J. Chen, Q. H. Yang, Chem. Asian J., 2017, 12, 577-585.
[54] L. He, C. Z. Li, J. Chen, L. N. Liu, Q. H. Yang, Chem. Asian J., 2017, 12, 1095-1103.
[55] M. L. Ding, H. L. Jiang, Chem. Commun., 2016, 52, 12294-12297.
[56] Q. Y. Deng, G. H. He, Y. Pan, X. H. Ruan, W. J. Zheng, X. M. Yan, RSC Adv., 2016, 6, 2217-2224.
[57] Y. Leng, D. Lu, P. P. Jiang, C. J. Zhang, J. W. Zhao, W. J. Zhang, Catal. Commun., 2016, 74, 99-103.
[58] M. S. Liu, K. Q. Gao, L. Liang, J. M. Sun, L. Sheng, M. Arai, Catal. Sci. Technol., 2016, 6, 6406-6416.
[59] T. Merner, N. Tenhumberg, H. Büttner, ChemCatChem, 2014, 6, 3493-3500.
[60] S. Ravi, D. H. Kang, R. Roshan, J. Tharun, A. C. Kathalikkattil, D. W. Park, Catal. Sci. Technol., 2015, 5, 1580-1587.
[61] M. S. Liu, B. Liu, L. Shi. F. X. Wang, L. Liang, J. M. Sun, RSC Adv., 2015, 5, 960-966.
[62] S. G. Liang, H. Z. Liu, T. Jiang, J. L. Song, G. Y. Yang, B. X. Han, Chem. Commun., 2011, 47, 2131-2133.
[63] Y. Y. Song, C. Cheng, H. W. Jing, Chem. Eur. J., 2014, 20, 12894-12900.
[64] X. Liu, S. Zhang, Q. W. Song, X. F. Liu, R. Ma, L. N. He, Green Chem., 2016, 18, 2871-2876.
[65] J. Steinbauer, T. Werner, ChemSusChem, 2017, 10, 3025-3030.
[66] J. L. Song, B. B. Zhang, P. Zhang, J. Ma, J. L. Liu, H. L. Fan, T. Jiang, B. X. Han, Catal. Today, 2012, 183, 130-135.
[67] Z. F. Yang, J. Sun, W. G. Cheng, J. Q. Wang, Q. Li, S. J. Zhang, Catal. Commun., 2014, 44, 6-9.
[68] Y. Kohno, H. Ohno, Phys. Chem. Chem. Phys., 2014, 14, 5063-5070.
[69] Y. Kohno, S. Saita, Y. J. Men, J. Y. Yuan, H. Ohno, Polym. Chem., 2015, 6, 2163-2178.
[70] Y. X. Qiao, W. B. Ma, N. Theyssen, C. Chen, Z. S. Hou, Chem. Rev., 2017, 117, 6881-6928.
[71] X. Jin, D. X. Yang, X. F. Xu, Z. Q. Yang, Chem. Commun., 2012, 48, 9017-9019.
[72] Y. P. Hao, J. Y. Jiang, Y. H. Wang, Z. L. Jin, Catal. Commun., 2015, 71, 106-110.
[73] M. D. Zhou, M. J. Liu, L. L. Huang, J. Zhang, J. Y. Wang, X. B. Li, F. E. Kühn, S. L. Zang, Green Chem., 2015, 17, 1186-1193.
[74] Z. Sun, L. F. Xue, S. T. Wang, X. H. Wang, J. Y. Shi, Green Chem., 2016, 18, 742-752.
[75] J. Luo, T. T. Xin, Y. L. Wang, New J. Chem., 2013, 37, 269-273.
[76] X. X. Duan, G. R. Sun, Z. Sun, J. X. Li, S. T. Wang, X. H. Wang, S. W. Li, Z. J. Jiang, Catal. Commun., 2013, 42, 125-128.
[77] X. L. Meng, H. Y. He, Y. Nie, X. P. Zhang, S. J. Zhang, J. J. Wang, ACS Sustain. Chem. Eng., 2017, 5, 3081-3086.
[78] L. Q. He, S. J. Qin, T. Chang, Y. Z. Sun, X. R. Gao, Catal. Sci. Technol., 2013, 3, 1102-1107.
[79] T. Chang, L. Q. He, L. Bian, H. Y. Han, M. X. Yuan, X. R. Gao, RSC Adv., 2014, 4, 727-731.
[80] J. Peng, S. Wang, H. J. Yang, B. R. Ban, Z. D. Wei, L. H. Wang, B. Lei, Fuel, 2018, 224, 481-488.
[81] J. Peng, Y. C. Geng, H. J. Geng, H. J. Yang, W. He, Z. D. Wei, J. K. Yang, C. Y. Guo, Mol. Catal., 2017, 432, 37-46.
[82] J. Peng, H. J. Yang, S. Wang, B. R. Ban, Z. D. Wei, B. Lei, C. Y. Guo, J. CO₂ Util., 2018, 24, 1-9.
[83] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, F. Toyota, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroveroe, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Raga, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Comperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, Revision D.01, Gaussian, Inc., Wallingford, CT, 2009.
[84] I. Mayer, J. Comput. Chem., 2007, 28, 204-221.
[85] T. Lu, F. W. Chen, J. Comput. Chem., 2012, 33, 580-592.

Temperature-responsive self-separation ionic liquid system of zwitterionic-type quaternary ammonium-KI for CO₂ fixation

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