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Electrophilic aromatic substitution. Part 34. Nitration of 1-chloro-4-nitro-benzene, 1,3-dichloro-2-nitrobenzene, 1,3-dinitrobenzene, 1-chloro-2,4-dinitro-benzene, and 2-chloro-1,3-dinitrobenzene in sulphuric acid and oleum
J. Chem. Soc., Perkin Trans. 2 Pub Date : 1988 , DOI: 10.1039/p29880001637
Martin W. Melhuish , Roy B. Moodie , Malcolm A. Payne , Kenneth Schofield

Yields of the expected nitro products from 1-chloro-4-nitrobenzene and 1,3-dichloro-2-nitrobenzene nitrated at 25 °C in sulphuric acid or oleum containing 1 mol dm–3 nitric acid were quantitative. The rate profile for nitration of 1,3-dichloro-2-nitrobenzene is normal, but sulphonation is a competing process when the concentration of nitric acid is low. Kinetics of nitration of 1,3-dinitrobenzene at 150 °C are reported; yields of 1,3,5-trinitrobenzene, the only detected aromatic product, are low. The title chlorodinitrobenzenes each give, on nitration at 130 °C, a dichlorodinitrobenzene as well as a chlorotrinitrobenzene. The kinetics and yields of the two products from 1-chloro-2,4-dinitrobenzene under a variety of conditions are reported and discussed in relation to a previously proposed mechanism.

中文翻译:

亲电芳族取代。第34部分:1-氯-4-硝基苯,1,3-二氯-2-硝基苯,1,3-二硝基苯,1-氯-2,4-二硝基苯和2-氯-1的硝化,硫酸和发烟硫酸中的3-二硝基苯

在25°C的硫酸或含1 mol dm –3硝酸的发烟硫酸中硝化的1-氯-4-硝基苯和1,3-二氯-2-硝基苯的预期硝基产物的产率是定量的。1,3-二氯-2-硝基苯的硝化速率曲线是正常的,但是当硝酸浓度低时,磺化是一个竞争过程。报道了在150℃下1,3-二硝基苯的硝化动力学。仅检测到的芳族产品1,3,5-三硝基苯的收率很低。标题的氯二硝基苯各自在130℃下硝化时得到二氯二硝基苯以及氯三硝基苯。报道并讨论了在各种条件下1-氯-2,4-二硝基苯的两种产物的动力学和收率。
更新日期:2017-01-31
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