2,5-二羧酸二乙酯-3,4-乙撑二氧噻吩的合成研究
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摘要
2,5-二羧酸二乙酯-3,4-乙撑二氧噻吩是经典五步法合成3,4-乙撑二氧噻吩工艺中的重要中间体,也是制约其路线收率的关键步骤,本文采用Williamson合成法醚化成环制备了2,5-二羧酸二乙酯-3,4-乙撑二氧噻吩,通过红外光谱、核磁共振波谱对产物的结构进行了表征分析,研究了催化剂、催化剂用量和反应原料对2,5-二羧酸二乙酯-3,4-乙撑二氧噻吩收率的影响,获得了最佳合成工艺,产物收率提高至95.1%。本合成工艺具有原料廉价易得、成本低、产率高等优点。
2,5-dicarbethoxy-3,4-ethylenedioxythiophene was the most important intermediate to synthesize 3,4-ethylenedioxythiophene(EDOT) via the classical Five-step method, as well as the key step to restrict the yield of the route. 2,5-dicarbethoxy-3,4-ethylenedioxythiophene was efficiently prepared through Williamson ether synthesis reaction. The structure of the target product was characterized by means of FTIR and NMR, respectively. The effects of the factors such as catalyst, the amount of the catalyst, and the raw materials on the yield of the product were investigated. The yield of the product reached up to 95.1% under optimum conditions. The method had some advantages such as cheaper and more available raw materials, lower cost and higher yield.
2,5-dicarbethoxy-3,4-ethylenedioxythiophene was the most important intermediate to synthesize 3,4-ethylenedioxythiophene(EDOT) via the classical Five-step method, as well as the key step to restrict the yield of the route. 2,5-dicarbethoxy-3,4-ethylenedioxythiophene was efficiently prepared through Williamson ether synthesis reaction. The structure of the target product was characterized by means of FTIR and NMR, respectively. The effects of the factors such as catalyst, the amount of the catalyst, and the raw materials on the yield of the product were investigated. The yield of the product reached up to 95.1% under optimum conditions. The method had some advantages such as cheaper and more available raw materials, lower cost and higher yield.
引文
[1]许晓俊,鲁华胜,杭颖,等.3,4-乙撑二氧噻吩的合成工艺研究进展[J].化工进展,2014,33(1):261-266.
[2]刘湘鄂,延卫,刘一流.3,4-乙撑二氧噻吩的合成研究[J].化学试剂,2009,31(8):649-651.
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[6]Fredrik V K,Fredrik A,Emma D,et a1.Simple one-step synthesis of3,4-dimethoxythiophene and its conversion into 3,4-ethylenedioxythiophene[J].Tetrahedron Letters,2004,45(31):6049-6050.
[7]Ng S C,Chan H O,Yu W L,et al.Synthesis and characterization of electrically conducting copolymers of ethylenedioxythiophene and1,3-propylenedioxythiophene withω-functional substituents[J].Journal of Materials Science Letters,1997,16(10):809-811.
[8]Coffey M,Mckellar B R,Reinhardt B A,et al.A facile synthesis of3,4-diakoxythiophenes[J].Synthetic Communicatios,1996,26(11):2205-2212.
[9]钱先峰,李寒旭,丁立明等.3,4-乙撑二氧噻吩(EDOT)的新合成方法[J].化工新型材料,2007,35(2):19-21.
[10]刑其毅.基础有机化学(第四版)[M].北京,高等教育出版社:2016.
[11]李刚.3,-乙撑二氧噻吩的合成工艺研究[D].浙江:浙江大学材料与化学工程学院,2007:29-30.
[2]刘湘鄂,延卫,刘一流.3,4-乙撑二氧噻吩的合成研究[J].化学试剂,2009,31(8):649-651.
[3]Pettersson L A,Carlsson F,Inganas O,et al.Spectroscopic ellipsometry studies of the optical properties of doped poly(3,4-ethyllenedioxythiophene):an anisotropic metal[J].Thin Solid Films,1998,313-314:356-361.
[4]Xu J K,Nie G M,ZHANG S S,et al.Electrochemical copolymerization of indole and 3,4-ethylenedioxythiophene[J].Journal of Materials science,2005,40(11):2867-2873.
[5]Stenger J D.Intrinsically electrically conducting polymers synthesis,characterization and their applications[J].Progress in Polymer Science,1998,23(1):57-79.
[6]Fredrik V K,Fredrik A,Emma D,et a1.Simple one-step synthesis of3,4-dimethoxythiophene and its conversion into 3,4-ethylenedioxythiophene[J].Tetrahedron Letters,2004,45(31):6049-6050.
[7]Ng S C,Chan H O,Yu W L,et al.Synthesis and characterization of electrically conducting copolymers of ethylenedioxythiophene and1,3-propylenedioxythiophene withω-functional substituents[J].Journal of Materials Science Letters,1997,16(10):809-811.
[8]Coffey M,Mckellar B R,Reinhardt B A,et al.A facile synthesis of3,4-diakoxythiophenes[J].Synthetic Communicatios,1996,26(11):2205-2212.
[9]钱先峰,李寒旭,丁立明等.3,4-乙撑二氧噻吩(EDOT)的新合成方法[J].化工新型材料,2007,35(2):19-21.
[10]刑其毅.基础有机化学(第四版)[M].北京,高等教育出版社:2016.
[11]李刚.3,-乙撑二氧噻吩的合成工艺研究[D].浙江:浙江大学材料与化学工程学院,2007:29-30.