1,6-己二氨基甲酸酯合成的研究进展
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摘要
综述了1,6-己二氨基甲酸酯(HDC)合成所用的羰基化试剂及其相关的各类催化剂。对CO、CO2、碳酸二甲酯(DMC)和氨基甲酸酯等羰基化试剂合成HDC的优缺点进行了系统评述。指出氨基甲酸酯的低毒、高活性、来源广等优点使其发展为合成HDC最具工业化前景的羰基化试剂;同时对碳酸二甲酯和氨基甲酸酯制备HDC的催化剂进行了介绍、分类、评述和总结,以期为开发高效HDC合成催化剂提供指导。最后表明制备廉价、易分离回收和循环利用的环境友好催化剂是推动HDC产业化的关键。
Various carbonyl reagents and catalysts employed in the synthesis of dialkyl hexamethylene-1,6-diyldicarbamate(HDC) were reviewed.The advantages and disadvantages of carbonyl reagents such as CO,CO2,dimethyl carbonate(DMC) and alkyl carbamate in the synthesis of HDC were analyzed systematically.The low toxicity,high activity and wide raw material sources make alkyl carbamate the most industrialized carbonyl reagent for HDC synthesis.The catalysts for the preparation of HDC from dimethyl carbonate and alkyl carbamate were introduced,classified,reviewed and summarized in the aim of providing a guide for the development of efficient catalyst for HDC synthesis.Preparation of cheap,easy recovered and recyclable environmentally friendly catalyst would be the key to promote the industrialization of HDC synthesis.
Various carbonyl reagents and catalysts employed in the synthesis of dialkyl hexamethylene-1,6-diyldicarbamate(HDC) were reviewed.The advantages and disadvantages of carbonyl reagents such as CO,CO2,dimethyl carbonate(DMC) and alkyl carbamate in the synthesis of HDC were analyzed systematically.The low toxicity,high activity and wide raw material sources make alkyl carbamate the most industrialized carbonyl reagent for HDC synthesis.The catalysts for the preparation of HDC from dimethyl carbonate and alkyl carbamate were introduced,classified,reviewed and summarized in the aim of providing a guide for the development of efficient catalyst for HDC synthesis.Preparation of cheap,easy recovered and recyclable environmentally friendly catalyst would be the key to promote the industrialization of HDC synthesis.
引文
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[27]邓友全,石峰,顾彦龙,等.胺和碳酸二甲酯反应制氨基甲酸酯的方法:中国,1424309[P].2003-06-18.
[28]李芳,赵熙,王延吉,等.ZrO2/SiO2催化合成1,6-六亚甲基二氨基甲酸甲酯的研究[J].石油化工,2004,33:1695-1697.
[29]卢玲,康仕芳,李国兵.固体碱催化剂上HDC的洁净合成[J].化学工业与工程,2006,23(1):25-28.
[30]邓友全,石峰,郭晓光,等.催化制备六亚甲基二氨基甲酸甲酯的方法:中国,101195591[P].2008-06-11.
[31]Shang J,Guo X,Deng Y,et al.N-substituted carbamates syntheseswith alkyl carbamates as carbonyl source over Ni-promoted Fe3O4catalyst[J].Journal of Catalysis,2011,279:328-336.
[32]Sun D,Deng J,Chao Z.Catalysis over zinc-incorporated berlinite(ZnAlPO4)of the methoxycarbonylation of 1,6-hexanediamine withdimethyl carbonate to form dimethylhexane-1,6-dicarbamate[J].Chemistry Central Journal,2007,1:27.
[2]马德强,尚永华,李宝军.脂肪族异氰酸酯的生产状况及技术进展[J].涂料化工,2005,35(12):35-40.
[3]周昱,程杰,王公应,等.六亚甲基-1,6-二异氰酸酯的合成工艺[J].聚氨酯工业,2006,21(4):44-46.
[4]孙大雷,谢顺吉,邓剑如,等.HDI合成工艺研究进展[J].化学工业与工程,2010,27(3):271-277.
[5]Franz M,Gerhard N,Friedrich T,et al.Preparation of hexamethylene1,6-diisocyanate and/or isomer diisocyanates where alkylene is of 6carbon atoms:US,4613466[P].1986-09-23.
[6]石峰,周瀚成,陈楠,等.非光气含氮化合物催化羰化研究进展[J].化学进展,2004,16(6):940-948.
[7]魏东,王越,王公应,等.1,6-六亚甲基二氨基甲酸甲酯合成研究进展[J].工业催化,2008,16(4):13-18.
[8]张俊,夏春谷.硝基苯还原羰基化反应制备氨基甲酸酯选择性的研究[J].化学学报,2003,61(3):427-429.
[9]Shi F,Deng Y.A novol PdCl2/ZrO2-SO42 catalyst for synthesis ofcarbamates by oxidative carbonylation of amines[J].Journal ofCatalysis,2001,203:525-528.
[10]Shi F,He Y,Deng Y,et al.Developing effective catalyst system forreductive carbonylation of nitrobenzene based on the diversity of ionliquids[J].Journal of Molecoular Catalysis A,2006,244:64-67.
[11]Mcghee W,Riley D,Chist K,et al.Carbon dioxide as a phosgenereplacement:Synthesis and mechanistic studies of urethanes fromamines,CO2,and alkyl chlorides[J].Journal of Organic Chemistry,1995,60(9):2820-2830.
[12]许景秀,赵金武.1,6-六亚甲基二氨基甲酸乙酯的绿色合成[J].应用化工,2010,39(1):144-146.
[13]Guo X,Shang J,Deng Y,et al.Synthesis of dialkylhexamethylene-1,6-dicarbamate from 1,6-hexamethylenediamine andalkyl carbamate over FeCl3as catalyst[J].Catalysis Communication,2009,10:1248-1251.
[14]邱志燕,杨勇,崔咪芬,等.无溶剂法合成1,6-六亚甲基二氨基甲酸甲酯[J].精细石油化工,2010,27(5):25-28.
[15]张名凯,邓剑如,孙大雷,等.以尿素为羰化剂合成六亚甲基二氨基甲酸酯的工艺研究[J].化工进展,2005,24(10):1151-1154.
[16]李晓楠.尿素醇解法合成HDC工艺及中间体的热力学性质的研究[D].上海:华东理工大学,2012.
[17]王天立,王贺玲.1,6-六亚甲基二氨基甲酸甲酯的清洁合成研究[J].江苏化工,2006(7):14-16.
[18]Deleon R G,Kobayshi A,Baba T,et al.Catalyticmethoxycarbonylation of 1,6-hexanediamine with dimethyl carbonateto dimethylhexane-1,6-dicarbamate using Bi(NO3)3[J].AppliedCatalysis A:General,2002,225:43-49.
[19]孙大雷,谢顺吉,邓剑如,等.醋酸锌催化碳酸二甲酯胺解合成六亚甲基二氨基二甲酸甲酯[J].精细石油化工,2010,27(6):9-13.
[20]周昱,李建国,王公应,等.合成六亚甲基1,6-二氨基甲酸甲酯的新方法[J].合成化学,2007,15(3):342-346.
[21]程杰.DMC和1,6-己二胺合成六亚甲基二氨基甲酸甲酯催化剂的研究[D].成都:中科院成都有机化学研究所,2005.
[22]Zhang H,Guo X,Deng Y.Synthesis of dialkylhexamethylenedicarbamate from 1,6-hexamethylenediamineand alkylcarbamate over Y(NO3)3.6H2O catalyst[J].Journal of MolecularCatalysis A:Chemical,2008,296:36-41.
[23]薛为岚,赵萍,曾作祥,等.一种六亚甲基二氨基甲酸丁酯的制备方法:中国,102391153[P].2012-03-28.
[24]邓友全,郭晓光,尚建鹏,等.一种合成二氨基甲酸酯的方法:中国,101468957[P].2009-07-01.
[25]王公应,程杰,姚洁.一种六亚甲基-1,6-二氨基甲酸甲酯的合成方法:中国,1727330[P].2006-02-01.
[26]王越,魏冬,王公应,等.一种用氧化物催化合成六亚甲基-1,6-二氨基甲酸甲酯的方法:中国,101565389[P].2009-10-28.
[27]邓友全,石峰,顾彦龙,等.胺和碳酸二甲酯反应制氨基甲酸酯的方法:中国,1424309[P].2003-06-18.
[28]李芳,赵熙,王延吉,等.ZrO2/SiO2催化合成1,6-六亚甲基二氨基甲酸甲酯的研究[J].石油化工,2004,33:1695-1697.
[29]卢玲,康仕芳,李国兵.固体碱催化剂上HDC的洁净合成[J].化学工业与工程,2006,23(1):25-28.
[30]邓友全,石峰,郭晓光,等.催化制备六亚甲基二氨基甲酸甲酯的方法:中国,101195591[P].2008-06-11.
[31]Shang J,Guo X,Deng Y,et al.N-substituted carbamates syntheseswith alkyl carbamates as carbonyl source over Ni-promoted Fe3O4catalyst[J].Journal of Catalysis,2011,279:328-336.
[32]Sun D,Deng J,Chao Z.Catalysis over zinc-incorporated berlinite(ZnAlPO4)of the methoxycarbonylation of 1,6-hexanediamine withdimethyl carbonate to form dimethylhexane-1,6-dicarbamate[J].Chemistry Central Journal,2007,1:27.
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