Dichloroisocyanuric Acid Sodium Salt에 의한 p-Nitrophenyl Diphenyl Phosphate의 가수분해 반응

이용한; 박훈; 최귀남; 장성일; 김태흥

Journal of the Korean Industrial and Engineering Chemistry, Vol.5, No.1, 114-120, February, 1994

Export Citation

Dichloroisocyanuric Acid Sodium Salt에 의한 p-Nitrophenyl Diphenyl Phosphate의 가수분해 반응

Hydrolysis of p-N itrophenyldipheny1phosphate by Dichloroisocyanuric Acid Sodium Salt

이용한, 박훈, 최귀남, 장성일, 김태흥

초록

DCI (dichlorolsocyanuric acid sodium salt)에 의한 PNPDPP (p-nitrophenyldiphenylphosphate)의 미셀 내에서의 분해 반응을 pH 8.0 borate완충용액에서 속도론적으로 살펴보았다. 양이온성 계면활성제인 CTAC (cetyltrimethylammonium chloride) 또는 CTAB (cetyltrimethylammonium bromide)를 첨가하면 반응은 빠르게 촉진되었으며, 특히 CTAB의 경우는 DCI의 N-Cl 결합이 N-Br 결합으로 전환되어 반응이 진행되었다.

Esterolysis reactions of PNPDPP (p-nitrophenyldiphenylphosphate) by DCI ( dichloroisocyanuric acid sodium salt) in borate buffer pH8.0 micellar phase were studied. The rate of hydrolysis reaction was rapidly increased by adding cationic surfactants, CTAC (cetyltrimethylammonium chloride) or CTAB (cetyltrimethylammonium bromide), to the DCI solution. Especially in CTAB micellar system, the N-Cl bond of DCI was transformed to the N-Br bond during the reaction.

[References]

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[1] Menger FM, Gan LH, Johnson E, Durst DH, J. Am. Chem. Soc., 109, 2800 (1987)

[2] Hammond PS, Forster JS, Lieske CN, Durst HD, J. Am. Chem. Soc., 111, 7860 (1989)

[3] Moss RA, Kim KY, Swarup S, J. Am. Chem. Soc., 108, 788 (1986)

[4] Epstein J, Bauer VE, Saxe M, Demek MM, J. Am. Chem. Soc., 78, 4068 (1956)

[5] Gulick WM, Geske DH, J. Am. Chem. Soc., 88, 2928 (1966)

[6] Connors KA, "Chemical Kinetics," The VCH Publishers, New York (1990)

[7] Bunton CA, Robinson L, J. Org. Chem., 34, 773 (1969)

[8] Menger FM, Portnoy CE, J. Am. Chem. Soc., 89, 4698 (1967)

[9] Bunton CA, Fendler EJ, Sepulveda L, Yang KU, J. Am. Chem. Soc., 90, 5512 (1968)

[10] Mark HF, "Kirk-Othmer Encyclopedia of Chemical Technology," 3rd ed., Vol. 3, pp. 567-570, John Wiley & Sons, New York (1978)

[11] Farkas L, Lewin M, J. Am. Chem. Soc., 72, 5766 (1950)

[12] Morris JC, J. Phys. Chem., 70, 3798 (1966)

[13] Cheek CH, LinnenbomVJ, J. Phys. Chem., 67, 1856 (1963)

[14] Soulard M, Bock F, Hatter A, J. Chem. Soc.-Dalton Trans., 2300 (1981)

[15] Park BD, Lee YS, Bull. Korean Chem. Soc., 13, 1 (1992)

[16] Park BD, Lee YS, Bull. Korean Chem. Soc., 13, 5 (1992)

[17] Hartman WW, Dickey JB, "Org. Synth," Coll. Vol. II, p. 173 (1957)

[18] Swain CG, Crist DR, J. Am. Chem. Soc., 94, 3195 (1972)