Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
권호 표지

Synthesis of Furfural Derivatives (II). Oxime Formation of 2-Furfural and Some 5-Substituted Furfurals

Furfural 유도체 합성에 관한 연구 (제2보). 2-Furfural 및 5-치환 Furfural의 Oxime 생성반응

  • Yong In Kim (Department of Chemical Engineering, Hong Ik University) ;
  • Joo Hwan Sohn (Department of Chemical Engineering, Inha University)
  • 김용인 (홍익대학교 이공대학 화학공학과) ;
  • 손주환 (인하대학교 공과대학 화학공학과)
  • Published : 1977.04.30
Download PDF
⟨ Previous Next ⟩

Abstract

The rate of oxime formation of 2-furfural and 5-substituted-2-furfurals such as 5-methyl-2-furfural, 5-isopropyl-2-furfural, 5-tert-butyl-2-furfural, 5-isoamyl-2-furfural and 5-nitro-2-furfural have been measured at 15∼$45^{\circ}C$ in aqueous solution buffered at pH 7. Oxime formation for all the compounds investigated is second-order reaction and their activation energies observed are 5.50, 7.22, 7.03, 7.49, 7.78 and 4.97 kcal/mole, respectively. Hammett equation is obtained for 5-alkyl-2-furfurals and the reaction constants (${\rho}$) calculated at 15, 25, 35 and $45^{\circ}C$ are 2.010, 1.756, 1.541, and 1.311 respectively.

2-푸르푸랄과 5-알킬-2-푸르푸랄류 가운데 5-메틸-2-푸르푸랄, 5-이소프로필-2-푸르푸랄, 5-삼차부틸-2-푸르푸랄, 5-이소아밀-2-푸르푸랄, 그리고 5-니트로-2-푸르푸랄 등의 옥심 생성반응 속도 정수를 pH 7인 완충용액내 반응온도 15∼$45^{\circ}C$에서 구하였다. 이 반응은 2차반응이며 활성화 에너지는 각각 5.50, 7.22, 7.03, 7.49, 7.78 그리고 4.97 kcal/mole이다. 5-알킬-2-푸르푸랄류에 대하여는 Hammett식이 성립되고 반응온도 15, 25, 35, $45^{\circ}C$에서 반응정수는 각각 2.010, 1.756, 1.541, 1.311 등이 계산되었다.

Keywords

References

  1. Ber. v.15 A. Janny
  2. Z. Physik. Chem. v.129 A. Olander
  3. J. Amer. Chem. Soc. v.66 G. H. Stemple;G. S. Schaffel
  4. J. Amer. Chem. Soc. v.78 F. W. Fitzpatrick;J. D. Gettler
  5. J. Amer. Chem. Soc. v.81 W. P. Jencks
  6. J. Pharm. Sci. v.59 T. J. Mikkelson;J. R. Robinson
  7. Anal. Chin. Acta v.70 W. A. De Olivera;Meites Lous
  8. Org. Synth. Coll. v.II I. J. Rinkes
  9. J. Amer. Chem. Soc. v.15 Hill;Jennings
  10. J. Amer. Chem. Soc. v.55 H. Gilman;N. O. Calloway
  11. J. Amer. Chem. Soc. v.57 H. Gilman;R. R. Burtner
  12. J. Amer. Chem. Soc. v.52 H. Gilman;G. F. Wright
  13. J. Amer. Chem. Soc. v.63 F. P. Price, Jr.;L. P. Hammett
  14. Anal. Chem. v.23 G. R. Lappin;L. C. Clark
  15. Theory of Rate Process Chem.4 S. Glasstone;K. J. Laidler;H. Eyring
  16. J. Chem. Soc. R. A. Fairclough;C. N. Hinsbelwood
  17. 日化 v.77 井木英二;大迂吉男;井上博夫
  18. 日化 v.80 井木英二;大迂吉男
  19. The chemistry of The Carbonyl Group P. Patai;R. L. Reeves
  20. J. Amer. Chem. Soc v.75 B. Gutbezahl;E. Grunwald
  21. J. Amer. Chem. Soc. v.74 H. Kloosterziel;H. J. Baker