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Catalytic Synthesis of Tris(4-aminophenyl)thiophosphate and Its Analogues by Triethylamine/Pyridine

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

Issue:
2011年03期
Page:
397-401
Research Field:
Publishing date:

Info

Title:
Catalytic Synthesis of Tris(4-aminophenyl)thiophosphate and Its Analogues by Triethylamine/Pyridine
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
Keywords:
triethylamine/pyridine tris(4-aminophenyl)thiophosphate acid binding agent catalysis synthesis
PACS:
O621.3
DOI:
-
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.

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

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Last Update: 2012-06-30