Study On The Technics About The Synthesize Of Irganox 565

The synthesis of Irganox 565 is investigated in this dissertation.2,6-di-tert-butylphenol, as the initial substrate,is nitrated to 2,6-di-tert-butyl-4-nitrophenol in 95%yield. 2,6-di-tert-butyt-4-nitrophenol is reduced to 4-amion-2,6-di-tert-butylphenol with hydrogen in the presence of Raney Ni or Pd/C.To prevent decomposition of 4-amion -2,6-di-tert-butytphenol when exposed to air,4-amion-2,6-di-tert-butylphenol is allowed to react with Cyanuric chloride without separation to form 6-(3,5-di-tert-butyl-4-hydroxy)aniline-2,4-dichloro-1,3,5-triazin in 95%yield for 2 steps. Reaction of 6-(3,5-di-tert-butyl-4-hydroxy)aniline-2,4-dichloro-1,3,5-triazin with 2 equivalence of n-Octylthiol gave the final product 6-(3,5-di-tert-butyl-4-hydroxy) aniline-2,4-bis(octylthio)-1,3,5-triazin in 94%yield.The recycling and reuse of Raney Ni and Pd/C,used as catalyst in hydrogenation of 2,6-di-tert-butyl-4-nitrophenol,are discussed in the paper.The catalytic activity of Raney Ni and Pd/C have not significant loss even after being reused for several times.The yield of 6-(3,5-di-tert-butyl-4-hydroxy)aniline-2,4-dichloro-1,3,5-triazin keeps over 90%. Nucleophilic substitution on 2,4,6-trichloro-1,3,5-triazine is studied.Substitution of the three chlorine atoms requires different conditions.After improvement,the total yield of Irganox 565 is increased from literature value of 54.7%to 78%.Raney Ni and Pd/C can be reused and the conditions of the reactions are milder and safer than that reported in the literature.