Reaction of Halonaphthalenes with SO3

Abstract

Abstract: The sulfonation of the six halonaphthalenes with SO₃ in dichloromethane as the solvent was studied by using ¹H NMRas method of analysis of the resulting mixure of sulfo derivatives. Monosulfonation of 1-fluoronaphthalene yields only the 4-S, where the other three 1-halonaphthalenes yielded in addition to some 5-S. Further sulfonation of any of the four 1-halonaphthalenes-4-S's yields a mixtures of the 2, 4-S₂, and 4, 7-S₂, and eventually also some 2, 4, 7-S₃. Sulfonation of 2-chloro-and 2-bromonaphthalenes with 1. 0 mole of SO₃ yields a mixture containing predominantly 8-S(～85%) with small amount of 4-S(～15%).The eventual products on using>4. 0 mole of SO₃ are 4, 7-S₂, and 6, 8-S₂.

Key words: Sulfonation, Sulfur trioxide, Halonaphthalenes

TrendMD:

LIN Jing, ZOU You-Si. Reaction of Halonaphthalenes with SO₃[J]. Chem. J. Chinese Universities, 1994, 15(11): 1654.

[1]	FU Zhinan, TAN Yunlong, XIAO Guyu, YAN Deyue. Synthesis and Properties of Sulfonated Poly（phthalazinone ether phosphine oxide）s with Perfluorobiphenyl Moieties for Proton Exchange Membranes [J]. Chem. J. Chinese Universities, 2021, 42(8): 2635.
[2]	CHENG Qinwen, YUAN Bo, ZHU Xiangdong, ZHANG Kai, ZHANG Xingdong. Surface Elemental Compositions and in Vitro Bioactivities of the PEEK Materials with Various Sulfonation and Alkali Treatments [J]. Chem. J. Chinese Universities, 2019, 40(8): 1757.
[3]	XIAO Lei, ZHANG Chen, HE Meiyu, CHEN Kangcheng. Precise Controllable Post-sulfonation for Preparation of Sulfonated Poly(arylene ether sulfone)s and Their Properties for Proton Exchange Membrane^† [J]. Chem. J. Chinese Universities, 2018, 39(6): 1281.
[4]	WANG Peng, WU Xian, ZHANG Hanyu, YOU Kaiyuan, LIU Zhenchao, LIU Baijun. Preparation of the Blend Membranes Based on Sulfonated Polyetheretherketoneketone and Amine-terminated Hyperbranched Polyimide^† [J]. Chem. J. Chinese Universities, 2018, 39(3): 405.
[5]	LIANG Yu, CHEN Zhihao, LIANG Baoyan, HU Zhe, YANG Xiaomin, WANG Zichen. Preparation of Rice Husk Carbon-based Solid Acid Catalyst for the Dehydration of Xylose to Furfural^† [J]. Chem. J. Chinese Universities, 2016, 37(6): 1123.
[6]	LU Miao, LIU Jianyun, WANG Shiping, CHENG Jian. Preparation of Sulfonated Graphene/Activated Carbon Composite Electrode for Asymmetric Capacitive Deionization^† [J]. Chem. J. Chinese Universities, 2014, 35(7): 1546.
[7]	ZHANG Shou-Hai, JIANG Yi-Wen, CHEN Li-Yun, JIAN Xi-Gao. Synthesis and Properties of Sulfonated Poly(phthalazinone ether ketone ketone)s Containing Pendant Phenyl Groups [J]. Chem. J. Chinese Universities, 2013, 34(8): 1993.
[8]	LI Xiu-Hua*, XIAO Dai-Li. Synthesis and Properties of Sulfonated Poly(phthalazinone ether ketone) Ionomers Containing Poly(fluorene ether ketone) Hydrophobic Moieties [J]. Chem. J. Chinese Universities, 2010, 31(10): 2074.
[9]	DOU Zhi-Yu, LIU Chen-Guang,LI Xian-Feng,ZHAO Cheng-Ji, ZHONG Shuang-Ling, NA Hui. Synthesis and Characterization of a Novel Sulfonated Polyimide Used as Proton Exchange Membrane [J]. Chem. J. Chinese Universities, 2006, 27(3): 586.
[10]	QING Sheng-Bo, HUANG Wei, YAN De-Yue. Synthesis and Characterization of Thermally Stable Sulfonated Polybenzimidazoles [J]. Chem. J. Chinese Universities, 2005, 26(11): 2145.
[11]	WANG Zhe, , LI Xian-Feng, ZHAO Cheng-Ji, LU Hui, NI Zhuo, NA Hui, QIAN Ya-Qin. Novel Proton Exchange Membranes Used for Fuel Cell──Sulfonated Poly(arylene ether sulfone) with tert-Butyl Groups [J]. Chem. J. Chinese Universities, 2005, 26(11): 2149.
[12]	LI Xian-Feng, NA Hui, LU Hui . A Novel Sulfonated Poly(ether ether ketone ketone)s Used as PEMFC [J]. Chem. J. Chinese Universities, 2004, 25(8): 1563.
[13]	LIU Chen-Guang, NA Hui, ZHAO Cheng-Ji, WU Zhong-Wen . Synthesis, Characterization and Properties of the Novel Sulfonated Poly(ether ether ketone)s [J]. Chem. J. Chinese Universities, 2004, 25(12): 2359.
[14]	LI Xian-Feng, NA Hui, LU Hui . Synthesis of a Novel Sulfonated Poly(ether ether sulfone)s Used as Proton Exchange Membrane Fuel Cell(PEMFC) [J]. Chem. J. Chinese Universities, 2004, 25(11): 2157.
[15]	XU Jian-Kuan, HE Bing-Lin . Preparation of a New Adsorbent for Binding Low Density Lipoprotein [J]. Chem. J. Chinese Universities, 2002, 23(7): 1421.

Reaction of Halonaphthalenes with SO₃

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments