[1]张跃华,张其平,胡兰萍,等.三乙胺/吡啶催化合成硫代磷酸三(4-氨基苯)酯及类似物[J].南京理工大学学报(自然科学版),2011,(03):397-401.
 ZHANG Yue-hua,ZHANG Qi-ping,HU Lan-ping,et al.Catalytic Synthesis of Tris(4-aminophenyl)thiophosphate and Its Analogues by Triethylamine/Pyridine[J].Journal of Nanjing University of Science and Technology,2011,(03):397-401.
点击复制

三乙胺/吡啶催化合成硫代磷酸三(4-氨基苯)酯及类似物
分享到:

《南京理工大学学报》(自然科学版)[ISSN:1005-9830/CN:32-1397/N]

卷:
期数:
2011年03期
页码:
397-401
栏目:
出版日期:
2011-06-30

文章信息/Info

Title:
Catalytic Synthesis of Tris(4-aminophenyl)thiophosphate and Its Analogues by Triethylamine/Pyridine
作者:
张跃华12张其平1胡兰萍1雷武2陈勇2夏明珠2王风云2
1. 南通大学化学化工学院,江苏南通226007; 2. 南京理工大学工业化学研究所,江苏南京210094
Author(s):
ZHANG Yue-hua12ZHANG Qi-ping1HU Lan-ping1LEI Wu2CHEN Yong2XIA Ming-zhu2WANG Feng-yun2
1.School of Chemistry and Chemical Engineering,Nantong University,Nantong 226007,China;2.Industrial Chemistry Institute,NUST,Nanjing 210094,China
关键词:
三乙胺/吡啶 硫代磷酸三(4-氨基苯)酯 缚酸剂 催化 合成
Keywords:
triethylamine/pyridine tris(4-aminophenyl)thiophosphate acid binding agent catalysis synthesis
分类号:
O621.3
摘要:
为提高硫代磷酸三(4-氨基苯)酯(TPTA)的产率,以对氨基酚和三氯硫磷为原料,三乙胺/吡啶为缚酸剂催化合成TPTA。通过实验得到了合成的最佳工艺条件:n(对氨基酚)∶n(三乙胺/吡啶)∶n(三氯硫磷)=3.05∶3.65∶1.00,n(三乙胺)∶n(吡啶)=1.00∶0.02,丙酮为溶剂,反应时间为4 h。在三乙胺中加入少量的吡啶,组成复式缚酸剂能有效地提高反应的产率。在此优化工艺条件下,TPTA的产率可达到69.6%。用类似的缚酸剂体系合成了硫代磷酸三(4-硝基苯)酯,硫代磷酸三(4-甲基苯)酯,通过红外光谱、核磁共振谱、质谱等手段对各产物进行了表征。
Abstract:
With the acid binding agent of triethylamine and pyridine,tris(4-aminophenyl)thiophosphate(TPTA)is catalyzed and synthesized from p-aminophenol and phosphorus thiochloride to improve the yield.The optimum reaction conditions are obtained by experiments,i.e.,the mole ratio of p-aminophenol to triethylamine/pyridine to phosphorus thiochloride is 3.05∶3.65∶1.00,the mole ratio of triethylamine to pyridine is 1.00∶0.02,the reaction solvent is acetone and the reaction time is 4 h.The complex acid binding agent by adding a small amount of pyridine into triethylamine can improve the yield effectively.Under the optimum reaction conditions,the yield of TPTA is 69.6%.Tris(4-nitrophenyl)thiophosphate and tris(4-methylphenyl)thiophosphate are synthesized by the similar acid binding agent system.The structure of the products is characterized by infrared spectrum,nuclear magnetic resonance and mass spectrometry.

参考文献/References:

[1] Renner A,Haug T. Storage stable mixtures of bis or tris imides and polyamines[P]. US: 3 849 374,1974 - 11 -19.
[2] Roger L. Photographic elements exhibiting improved stability[P]. EP: 0 721 145 A1, 1996 - 10 - 07.
[3] Makoto A. Preparation of organic isocyanate by twostage process comprising cooling and heating steps [P]. JP: 57 040 451, 1982 - 03 - 06.
[4] Heitkaemper P. Cold-hot phosgenation procedure for the manufacture of isocyanates from primary amines hardly soluble in chlorobenzene or o-dichlorobenzene [P]. DE: 19 651 041A1, 1998 - 10 - 06.
[5] 陈勇,雷武,夏明珠,等. 硫代磷酸三( 4 - 氨基苯酯) 的合成及应用进展[J]. 中国胶粘剂,2005,14( 9) : 42 - 45.
[6] 夏亦丹,梅继香. 对三异氰酸三苯基硫代磷酸酯交联聚乙烯醇乳胶[J]. 中国胶粘剂. 2003,12 ( 5) : 16 - 20.
[7] Yamashita R. Laminate and manufacturing method[P]. JP: 200 498 409A, 2004 - 04 - 02.
[8] Hirobumi Y,Toshihisa T. Silver salt photothermographic imaging material[P]. US: 0 175 630A1, 2003 - 09 - 18.
[9] Holtschmidt H, Stammheim K. Isocyanato substituted aryl phosphorus esters[P]. US: 3 013 048, 1961 -12 -12.
[10] Holtschmidt H,Stammheim C. Polyphosphate phenyl esters containing isocyanate radicals[P]. US: 3 136 806, 1964 - 06 - 09.
[11] Ciba. Process for the manufacture of aminoaryl phosphates and phosphonates[P]. GB: 1 027 059,1966 - 04 - 20.
[12] Ryuichi Y,Masaaki T. Process for the preparation of aminoaryl thiophosphates and aminoaryl phosphates [P]. US: 4 279 838, 1981 - 07 - 21.
[13] Ryuichi Y,Masaaki T. Process for the preparation of phosphoric esters and thiophosphoric esters[P]. GB: 2 034 314A, 1980 - 06 - 04.
[14] Otsuka I. Phosphoric or thiophosphoric esters[P]. JP: 60 152 492, 1985 - 08 - 10.
[15] 王新龙. 有机磷阻燃剂的合成和表征[D]. 南京: 南京理工大学化工学院, 2001.
[16] Jiang G H,Wang L,Chen T, et al. Synthesis and macroscopic self-assembly of multiarm hyperbranched polyethers with benzoyl-terminated groups[J]. Polymer, 2005, 46( 14) : 5351 - 5357. 401

备注/Memo

备注/Memo:
基金项目:国家自然科学基金( 20906052) ; 江苏省教育厅项目( 08KJB610007) ; 南通市科技项目( S2009010) 作者简介:张跃华( 1969 - ) ,男,副教授,主要研究方向: 水处理化学品的合成与开发,E-mail: zhangyuehua969@ 126. com; 通讯作者: 张其平( 1968 - ) ,男,副教授,主要研究方向: 精细化学品的合成与开发,E-mail: zqp@ ntu. edu. cn。
更新日期/Last Update: 2012-06-30