Crosslinked polystyrene beads modified with sulfonyl groups and their application in aromatic/aliphatic hydrocarbons separation

Abstract

The separation of aromatic hydrocarbons from aromatic/aliphatic mixtures was investigated with cross-linked polystyrene(CPS) beads modified with sulfonyl groups. Three sulfonating agents, i.e. benzenesulfonyl chloride( BsCl), 4-toluene sulfonyl chloride(TsCl) and methanesulfonyl chloride(MsCl) were used to prepare sulfonyl CPS beads by Friedel-Crafts reaction. The CPS beads modified with BsCl exhibited higher sulfonation rate than those modified with MsCl and TsCl and obtained optimum selectivity in the experiments of toluene/n-heptane separation. Further separation tests with various other aromatic/aliphatic mixtures were carried out at an initial aromatic concentration of 13%(mass fraction) with the results showing that the modified beads have preferential selectivity for aromatic hydrocarbons in all aromatic/aliphatic mixtures, and especially a separation factor of 8.21 and a swelling ratio of 30% for toluene/cyclohexane system. The thermal stability and regeneration test indicate that the used polystyrene beads can be recovered through heat-drying and reused effectively.

Keywords

Separation / Sulfonyl / Polystyrene / Swelling / Modification

References

[1] Choi Y J, Cho K W, Cho B W, Yeo Y K. Ind. Eng. Chem. Res., 2002, 41(22): 5504.

[2] Lin W, Tsai T, Lin T, Yang C. J. Chem. Eng. Data, 2008, 53(3): 760.

[3] Cassell G W, Hassan M M, Hines A L. J. Chem. Eng. Data, 1989, 34(4): 434.

[4] Al-jimaz A S, Fandary M S, Al-kandary J A, Fahim M A. Fluid Phase Equilibria, 2005, 231(2): 163.

[5] Saha M, Rawat B S, Khanna M K, Nautiyal B R. J. Chem. Eng. Data, 1998, 43(3): 422.

[6] Naidcoo R D, Letcher T M, Ramjugernath D. J. Chem. Eng. Data, 2001, 46(6): 1375.

[7] Ashour I, Abdelkarim M A. J. Chem. Eng. Data, 2005, 50(3): 924.

[8] Pereiro A B, Rodriguez A. J. Chem. Thermodynamics, 2009, 41(8): 951.

[9] Yan R, Shao M, Liang Z, Zhang H, Yu A. Chem. Res. Chinese Universities, 2013, 29(2): 218.

[10] Arce A, Earle M, Rodriguez H. J. Phys. Chem. B, 2007, 111(18): 4732.

[11] Meindersma G W, Podt A, Haan A B. Fuel Processing Technology, 2005, 87(1): 59.

[12] Freeman B D. Macromolecules, 1999, 32: 375.

[13] Yamasaki A, Shinbo T, Mizoguchi K. J. Appl. Polym. Sci., 1997, 64(6): 1061.

[14] Smitha B, Suhanya D, Sridhar S, Ramakrishna M. J. Membr. Sci., 2004, 241(1): 1.

[15] Garcia-arcia-villaluenga J P, Tabe-mohammadi A. J. Membr. Sci., 2000, 169(2): 159.

[16] Yoshikawa M, Tsubouchi K. Sep. Purif. Technol., 1999, 17(3): 213.

[17] Ren J, Staudt-bickel C, Lichtenthaler R N. Sep. Purif. Technol., 2001, 22/23: 31.

[18] Tanihara N, Tanaka K, Kita H, Okamoto K. J. Membr. Sci., 1994, 95(2): 161.

[19] Suding M T H, Staudt C. J. Appl. Polym. Sci., 2013, 127(6): 5065.

[20] Park H B, Jung C H, Lee Y M, Hill A J, Pas S J, Mudie S T, Wagner E V, Freeman B D, Cookson D J. Science, 2007, 318(5848): 254.

[21] Ribeiro C P, Freeman B D, Kalika D S, Kalakkunnath S. J. Membr. Sci., 2012, 390/391: 182.

[22] Maji S, Banerjee S, Pradhan N C. Sep. Purif. Technol., 2009, 70(1): 128.

[23] Qin L, He X, Zhang W, Li W, Zhang Y. Journal of Chromatography A, 2009, 1216(5): 807.

[24] Yun Y H, Shon H K, Yoon S D. J. Mater. Sci., 2009, 44(22): 6206.

[25] Mizutani A, Nagase K, Kikuchi A, Kanazawa H, Akiyama Y, Kobayashi J, Annaka M, Okano T. Journal of Chromatography A, 2010, 1217(4): 522.

[26] Zhang X, Shen S, Fan L. J. Mater. Sci., 2007, 42(18): 7621.

[27] Jun B H, Bynu J W, Kim J Y, Kang H, Park H, Yoon J, Lee Y. J. Mater. Sci., 2010, 45(11): 3106.

[28] Yu H, Cui Y, Liu X, Shi Z. Chem. J. Chinese Universities, 2014, 35(1): 186.

[29] Nara S J, Harjani J R, Salunkhe M M. J. Org. Chem., 2001, 66: 8616.

[30] Wang H, Ugomori T, Tanaka K, Kita H, Okamoto K, Suma Y. J. Polym. Sci., Part B: Polym. Phys., 2000, 38(22): 2954.

[31] Yu H, Cai Z, Liu X, Li M, Shi Z, Cui Z. J. Appl. Polym. Sci., 2014, 131(8): 40156.

[32] Frahn J, Malsch G, Matuschewski H. J. Membr. Sci., 2004, 234(1/2): 55.