2-硝基-1,3-苯二酚制备实验改革
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摘要
2-硝基-1,3-苯二酚是二苯甲酮类抗紫外线染料的合成中间体,该化合物的制备需要使用机械搅拌装置,因此2-硝基-1,3-苯二酚的合成实验在很多"双一流"、"985"高校中均有开设。但由于原料间苯二酚极易氧化,浓硫酸、浓硝酸都属于强腐蚀性的强酸,水蒸气蒸馏又操作繁琐,导致很多同学在实验过程中有畏惧心理,产率较低。本文对该实验中的试剂仪器要求、操作细节、每步反应机理、实验装置改良都进行了深入研究和改进,并对产物进行了NMR表征确认。教学方案经过同学们验证实验后,取得了很好的教学效果。
2-Nitro-1,3-benzenediol is a intermediate of anti-UV radiation dyes containing a built-in benzophenone. The experimental preparation of 2-nitro-1,3-benzenediol in many "Double First-Class" and "985 Project" universities are carried out due to need to use mechanical stirring device. However, many college students are fear to do this experiment because there are so many difficulties such as resorcinol is easily oxidized; the concentrated sulfuric acid and the concentrated nitric acid are strong corrosive acid; the operation of steam distillation is terrible. The requirements of reagent and instrument, operation of details and reaction mechanism are studied in the present paper. A good teaching result is achieved after students finished this experiment by new methods.
2-Nitro-1,3-benzenediol is a intermediate of anti-UV radiation dyes containing a built-in benzophenone. The experimental preparation of 2-nitro-1,3-benzenediol in many "Double First-Class" and "985 Project" universities are carried out due to need to use mechanical stirring device. However, many college students are fear to do this experiment because there are so many difficulties such as resorcinol is easily oxidized; the concentrated sulfuric acid and the concentrated nitric acid are strong corrosive acid; the operation of steam distillation is terrible. The requirements of reagent and instrument, operation of details and reaction mechanism are studied in the present paper. A good teaching result is achieved after students finished this experiment by new methods.
引文
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[2]Sarasin A.The molecular path ways of ultraviolet-induced carcinogenesis.Mutat.Res.,1999,428(1/2):5-10.
[3]王克昌,宁培森,丁著明.二苯甲酮类紫外线吸收剂的研究进展[J].化工文摘,2008,1:48-53.
[4]王云明,唐炳涛,马威,等.紫外吸收染料研究进展[J].有机化学,2010,30(3):330-337.
[5]Merritt C.,Scott G.W.Transient absorption spectra of 2-hydroxy-benzophenone photostabilizers.Chem.Phys.Lett.,1980,69:169-177.
[6]尹志刚,石薇云,李占才,等.有机化学[M].郑州:河南科学技术出版社,2009.
[7]李占才,尹志刚,蒋玲,等.转移催化法合成2-硝基-1,3-苯二乙醚[J].精细石油化工,2011,28(6):17-19.
[8]尹志刚,费宗雷,李占才,等.2-硝基-1,3-苯二甲醚的合成[J].精细化工,2011,28(1):101-103.
[9]王清廉,沈凤嘉.有机化学实验[M].北京:高等教育出版社,1994.
[10]罗一鸣,唐瑞仁.高等院校规划教材.有机化学实验[M].长沙:中南大学出版社,2012.