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.
Similar content being viewed by others
References
Choi Y. J., Cho K. W., Cho B. W., Yeo Y. K., Ind. Eng. Chem. Res., 2002, 41(22), 5504
Lin W., Tsai T., Lin T., Yang C., J. Chem. Eng. Data, 2008, 53(3), 760
Cassell G. W., Hassan M. M., Hines A. L., J. Chem. Eng. Data, 1989, 34(4), 434
Al-jimaz A. S., Fandary M. S., Al-kandary J. A., Fahim M. A., Fluid Phase Equilibria, 2005, 231(2), 163
Saha M., Rawat B. S., Khanna M. K., Nautiyal B. R., J. Chem. Eng. Data, 1998, 43(3), 422
Naidcoo R. D., Letcher T. M., Ramjugernath D., J. Chem. Eng. Data, 2001, 46(6), 1375
Ashour I., Abdelkarim M. A., J. Chem. Eng. Data, 2005, 50(3), 924
Pereiro A. B., Rodriguez A., J. Chem. Thermodynamics, 2009, 41(8), 951
Yan R., Shao M., Liang Z., Zhang H., Yu A., Chem. Res. Chinese Universities, 2013, 29(2), 218
Arce A., Earle M., Rodriguez H., J. Phys. Chem. B, 2007, 111(18), 4732
Meindersma G. W., Podt A., Haan A. B., Fuel Processing Technology, 2005, 87(1), 59
Freeman B. D., Macromolecules, 1999, 32, 375
Yamasaki A., Shinbo T., Mizoguchi K., J. Appl. Polym. Sci., 1997, 64(6), 1061
Smitha B., Suhanya D., Sridhar S., Ramakrishna M., J. Membr. Sci., 2004, 241(1), 1
Garcia-arcia-villaluenga J. P., Tabe-mohammadi A., J. Membr. Sci., 2000, 169(2), 159
Yoshikawa M., Tsubouchi K., Sep. Purif. Technol., 1999, 17(3), 213
Ren J., Staudt-bickel C., Lichtenthaler R. N., Sep. Purif. Technol., 2001, 22/23, 31
Tanihara N., Tanaka K., Kita H., Okamoto K., J. Membr. Sci., 1994, 95(2), 161
Suding M. T. H., Staudt C., J. Appl. Polym. Sci., 2013, 127(6), 5065
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
Ribeiro C. P., Freeman B. D., Kalika D. S., Kalakkunnath S., J. Membr. Sci., 2012, 390/391, 182
Maji S., Banerjee S., Pradhan N. C., Sep. Purif. Technol., 2009, 70(1), 128
Qin L., He X., Zhang W., Li W., Zhang Y., Journal of Chromatography A, 2009, 1216(5), 807
Yun Y. H., Shon H. K., Yoon S. D., J. Mater. Sci., 2009, 44(22), 6206
Mizutani A., Nagase K., Kikuchi A., Kanazawa H., Akiyama Y., Kobayashi J., Annaka M., Okano T., Journal of Chromatography A, 2010, 1217(4), 522
Zhang X., Shen S., Fan L., J. Mater. Sci., 2007, 42(18), 7621
Jun B. H., Bynu J. W., Kim J. Y., Kang H., Park H., Yoon J., Lee Y., J. Mater. Sci., 2010, 45(11), 3106
Yu H., Cui Y., Liu X., Shi Z., Chem. J. Chinese Universities, 2014, 35(1), 186
Nara S. J., Harjani J. R., Salunkhe M. M., J. Org. Chem., 2001, 66, 8616
Wang H., Ugomori T., Tanaka K., Kita H., Okamoto K., Suma Y., J. Polym. Sci., Part B: Polym. Phys., 2000, 38(22), 2954
Yu H., Cai Z., Liu X., Li M., Shi Z., Cui Z., J. Appl. Polym. Sci., 2014, 131(8), 40156
Frahn J., Malsch G., Matuschewski H., J. Membr. Sci., 2004, 234(1/2), 55
Author information
Authors and Affiliations
Corresponding author
Additional information
Supported by the National Natural Science Foundation of China(Nos.21204028, 51173063).
Rights and permissions
About this article
Cite this article
Yu, H., Cai, Z., Guan, J. et al. Crosslinked polystyrene beads modified with sulfonyl groups and their application in aromatic/aliphatic hydrocarbons separation. Chem. Res. Chin. Univ. 30, 1066–1070 (2014). https://doi.org/10.1007/s40242-014-4156-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s40242-014-4156-1