Synthesis of Polystyrene Modified with Sulfonyl and Extraction for Aromatics†

doi:10.7503/cjcu20130794

Abstract

Abstract:

A series of sulfonated low molecular weight polystyrene(LOPSS) was synthesized via radical polymerization, oxidation of end-group and Friedel-Crafts acylation reactions. The structures of obtained polymer were investigated by ¹H NMR, FTIR and thermal behavior of polymers was performed by differential scanning calorimetry(DSC) and thermo gravimetric analyzer(TGA). The selectivity for aromatic hydrocarbons was tested through extraction of aromatics from aromatic/aliphatic hydrocarbons. The results indicated that with the increase of sulfonylation degree, selectivity coefficient and distribution coefficient of toluene obviously increased. Polystyrene modified with polar monomer has good selectivity for aromatics from all kinds of aromatic/aliphatic hydrocarbons.

Key words: Polystyrene, Extraction, Polar, Sulfonylation, Aromatic hydrocarbon

CLC Number:

O631

TrendMD:

YU Huanyang, CUI Ying, LIU Xianying, SHI Zuosen. Synthesis of Polystyrene Modified with Sulfonyl and Extraction for Aromatics^†[J]. Chem. J. Chinese Universities, 2014, 35(1): 186.

Figures/Tables 9

Scheme 1 Synthetic routes of LOPSS

Table 1 Molecular weight(M) of modified PS

Polymer	m(TsCl)/g	Mass fraction of sulfone^*(%)	M(GPC)	M(¹H NMR)
LPS	0	0	2070	5042
LOPSS1	3.19	6.25	2100	5332
LOPSS2	6.38	14.28	2350	5695
LOPSS3	12.75	50.00	2730	6319

Fig.1 FTIR spectra of LOPSS1(a), LOPSS2(b) and LOPSS3(c)

Fig.2 1H NMR spectra of LOPSS1(a), LOPSS2(b) and LOPSS3(c)

Fig.3 DSC curves of LOPSS and LPS

Fig.4 TGA(A) and DTG(B) curves of LOPSS and LPS

Fig.5 Toluene/n-heptane separation with LOPSS and LPSSubscripts mean the sulfonation reaction time/h.

Fig.6 Aromatic/aliphatic hydrocarbons separationa. Benzene/cyclohexane; b. benzene/n-hexane; c. toluene/n-octane; d. p-xylene/n-octane; e. toluene/n-hexane; f. p-xylene/heptane; g. benzene/n-heptane.

Table 2 Regeneration of LOPSS

Times	First	Second	Third	Fourth	Fifth
S	8.10	8.02	7.95	7.89	7.82
K	1.46	1.43	1.41	1.40	1.38

References 25

[1]	Rawat B. S., Gulati I. B., J. Appl. Chem. Biotechnol., 1976, 26, 425—435
[2]	Chen J., Li Z. C., Duan L. P., J. Chem. Eng. Data, 2000, 45(4), 689—692
[3]	Choi Y. J., Cho K. W., Cho B. W., Yeo Y. K., Ind. Eng. Chem. Res., 2002, 41, 5504—5509
[4]	Mohammad D. F. S., Mohsen-Nia M., J. Chem. Eng. Data, 2006, 51(4), 1431—1435
[5]	Cassel G. W., Hassan M. M., Hines A. L., Chem. Eng. Commun., 1989, 85, 233—243
[6]	Letcher T. M., Ramjugernath D., Naidoo R. D., J. Chem. Eng. Data, 2001, 46(6), 1375—1380
[7]	Fandary M. S., Al-Jimaz A. S., Al-Kandary J. A., Fahim M. A., J. Chem. Thermodynamics, 2006, 38, 455—460
[8]	Al-Jimaz A. S., Fandary M. S., Al-Kandary J. A., J. Chem. Eng. Data, 2005, 50(5), 1740—1746
[9]	Wang W., Gou Z. M., Zhu S. L., J. Chem. Eng. Data, 1998, 43(1), 81—83
[10]	Al-Sahhaf T. A., Kapetanovic E., Fluid Phase Equilib., 1996,118(2), 271—285
[11]	Ashour I., Abdulkarim M. A., J. Chem. Eng. Data, 2005, 50(3), 924—927
[12]	Darwish N. A., Abdelkarim M. A., Hilal N., Ashour I., J. Chem. Eng. Data, 2003, 48(6), 1614—1619
[13]	Yorulmaz Y., Karpuzcu F., Chem. Eng. Res. Des., 1985, 63, 184—190
[14]	Zhang J., Huang C. P., Chen B. H., Ren P. J., Lei Z. G., Energy & Fuels, 2007, 21, 1724—1730
[15]	Yan R., Shao M., Liang Z., Zhang H., Yu A., Chem. Res. Chinese Universities, 2013, 29(2), 218—222
[16]	Calvar N., Domínguez I., Gómez E., Domínguez A., Chemical Engineering Journal, 2011, 175, 213—221
[17]	Zhu J., Chen J., Li C. Y., Fei W. Y., Sep. Purif. Technol., 2007, 56, 237—240
[18]	Li Z. S., Zhang B., Qu L. X., Ren J. Z., Li Y., J. Membr. Sci., 2011, 371, 163—170
[19]	Suding M.T. H., Staudt C., J. Appl. Polym. Sci., 2013, 5065—5074
[20]	Mandal M. K., Bhattacharya P. K., Sep. Purif. Technol., 2008, 61, 332—340
[21]	Qin L., He X., Zhang W., Li W., Zhang Y., Journal of Chromatography A, 2009, 1216, 807—814
[22]	Mizutani A., Nagase K., Kikuchi A., Kanazawa H., Akiyama Y., Kobayashi J., Annaka M., Okano T., Journal of Chromatography A, 2010, 1217, 522—529
[23]	Wang Q. H., Wang C. Z., Wei Y. M., Chem. J. Chinese Universities, 2012, 33(11), 2579—2584
	(王琴会, 王超展, 卫引茂.高等学校化学学报, 2012,33(11), 2579—2584)
[24]	Yu P. Z., Li X. Q., Li X. N., Lu X. L., Ma G. H., Su Z. G., Bioorganic & Medicinal Chemistry Letters, 2007, 17, 5605—5609
[25]	Schwarz H. H., Malsch G., J. Membr. Sci., 2005, 247, 143—152