Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Dehydropolycondensation of Aminopenols under the Catalytic Action of Metallic Chelate Compounds (I) Effects of the Solvents and Characteristics of the Oligomers Obtained

金屬킬레이트化合物의 觸媒作用에 依한 Aminophenol 類의 酸化的 重縮合反應 (Ⅰ) 溶媒의 效果와 生成重合體의 特性

  • Published : 19680900
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Abstract

Fe-EDTA complex, which is easily formed when Fe salt and EDTA.2Na are mixed in the aqueous medium, is found to be a very effective catalyst in the dehydropolycondensation of aminophenols. In the dehydropolycondensation of aminophenols, the catalyst, Fe(Ⅲ)-EDTA complex (higher oxidation state) is reduced to less stable Fe(Ⅱ)-EDTA complex (lower oxidation state), and the latter is easily oxidized by air to the original higher oxidation state complex, therefore the catalytic action of Fe-EDTA complex is found to be recycled effectively. Under the catalytic action of the above mentioned complex, p-aminophenol is polymerized in the aqueous medium to form the oligomers of p-aminophenol, which the degree of polymerization to be 5 or more. The oligomers formed contain partly quinone nucleus as well as amino and hydroxyl groups. In this study, the effects of the solvents and characteristics of the oligomers are discussed. These types of polymerizations catalyzed by the metallic chelate compounds are considered to be very closely related to the reactions in the living matters.

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References

  1. Chem. Ber. v.96 L. Horner;J. Dehnert
  2. J. Am. Chem. Soc. v.84 G.A. Russell
  3. J. Allg. Chem. (USSR) v.28 A.P. Terentjew
  4. J. Am. Chem. Soc. v.69 J. E. LuValle;A. Weissberger
  5. J. Am. Chem. Soc. v.70 J. E. LuValle;D.B. Glass;A. Weissberger
  6. Zh. Obsh. Khim. v.32 no.9 V.A. Simanov(et al.)
  7. J. Am. Chem. Soc. v.81 A.S. Hay;H.S. Blanchard
  8. J. Org. Chem. v.28 G. F. Endres;A.S. Hay
  9. Bull. Chem. Soc., Japan v.32 Keizo Kinoshita
  10. Zh. Obsh. Khim. v.31 A.P. Terentev
  11. J. Polymer Sci. v.58 A.S. Hay
  12. J. Polymer Sci. v.58 G.F. Endres(et al.)
  13. A.C.S. Polymer Preprints v.7 H.C. Bach
  14. Helv. Chim. Acta v.31 G. Schwarzenbach;J. Heller
  15. J. Am. Chem. Soc. v.48 J.B. Conant;M.F. Pratt
  16. Z. Naturforsch v.19b no.6 H.B. Stegmann;K. Scheffler
  17. Arbiv. Kemi., Mineral Geol. v.25A no.14 H.V. Euler;H. Hasselquist
  18. Vysokomolekul. Soedin. v.5 Y.U. Kissin;G.M. Pshenitsyna
  19. Vysokomolekul. Soedin. v.7 B.I. Liogonkii;A.V. Ragimov;Y.G. Aseev;A.A. Berlin
  20. 有機化合物의 微量確認法 杉山 登