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KMID : 0382420030290020050
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Korean Journal of Environmental Health Society
2003 Volume.29 No. 2 p.50 ~ p.55
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Synthesis and Isolation of Monoacetyl-DCB and Diacetyl-DCB from 3,3’ -dichlorobenzidine(DCB)
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Lee Jin-Heon
Lee Beom-Gyu
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Abstract
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3.3-dichlorobenzidine is suspected to be cancinogenic in experimental animal and human. Several studies have investigated excretion of metabolites in urine. hemoglobin adduction and cancer incidence among workers occupationally exposed to 3.3’-dichlorobenzidine. In these researches. metabolites of 3.3’-dichlorobenzidine had a very important role. and were required as highly purity. The purpose of this study was synthesis and isolation of its metabolites from 3.3’dichlorobenzidine. 3.3’-dichlorobenzidine was partially dissolved in benzene. ether. ethanol and methanol. and completely dissolved in 70% acetic acid on mixtures of citric acid containing less than 1% DCB. pyridine. a mixture of 0.5N NaOH and toluene( 1:2). and phenol saturated with 20 mM TRIZA base. DCB, monoacetyl-DCB and diacetyl-DCB were measured by using gas chromatography/mass spectrometry(GC/MS). Detection for checking them was nitrogen phosphorous detection mode(NPD). and for identifying them was selected ion monitoring mode(SIM). The base peaks were 252 m/z in DCB. 252. and 294 m/z in monoacetyl-DCB. and 252. 294 and 336 m/z in diacetyl-DCB. respectively. Diacetyl-DCB was synthesized by titrating DCB solution of pyridine with sufficient acetyl chloride. Precipitation was diacetyl-DCB. which was purity of 98.7%. And its supernatant was composed of DCB. monoacetyl-DCB and diacetyl-DCB. By using acetic acid as controller of acetylation, monoacetyl-DCB was isolated from diacetyl-DCB. And residual pyridine was removed by using acetone. The purity of monoacetyl-DCB was 98.8%.
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