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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 16, Number 5
JKCSEZ 16(5)
October 20, 1972 

Reaction of Furfural Derivatives. Cannizzaro reaction of Furfural, 5-Bromo-and 5-Methylfurfural

Cyclitol 유도체합성을 위한 Furfural 유도체의 반응에 관한 연구. Furfural, 5-Bromo-및 5-Methylfurfural의 Cannizzaro 반응
Joo Hwan Sohn, Yong In Kim, Ki Dae Nam

손주환, 김용인, 남기대
메탄올(95%) 용매내 0∼40℃에서 푸르푸랄, 5-메틸 및 5-브로모푸르푸랄의 알코올성 수산화칼륨에 의한 Cannizzaro 반응은 4차반응이며 푸르푸랄은 5-메틸푸르푸랄보다 3배, 5-브로모푸르푸랄은 푸르푸랄보다 10배 빠르게 진행된다. 그리고 이 반응에서 푸르푸랄, 5-메틸푸르푸랄, 5-브로모푸르푸랄의 활성화에너지는 각각 10.46Kcal/mole, 16.27Kcal/mole, 9.62Kcal/mole이며 ΔH≠ 와 ΔS≠를 계산한 바 5-브로모푸르푸랄, 푸르푸랄, 5-메틸푸르푸랄의 순으로 증가되었다.

We have obtained the results of Cannizzaro reaction of furfural, 5-methylfurfural and 5-bromofurfural by using alcoholic potassium hydroxide solution in 95% (V/V) methanol solvent at 0°~ 40℃. The results are as follows: 1) Their Cannizzaro reaction is fourth-order reaction, and the reaction of furfural proceeds 3 times as rapid as that of 5-methylfurfural and 10 times as slow as that of 5-bromofurfural. 2) Their activation energies of furfural, 5-methylfurfural and 5-bromofurfural in the reaction are 10.46Kcal/mole, 16.27Kcal/mole, and 9.62Kcal/mole respectively, and the calculated activation parameters, ΔH≠ and ΔS≠, increase in the order of 5-bromofurfural, furfural and 5-methyl-furfural.

290 - 297
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