Kanetoshi A, Ogawa H, Katsura E, Kaneshima H
J Chromatogr. 1987 Feb 27;389(1):139-53. doi: 10.1016/s0021-9673(01)94418-8.
Irgasan DP300 (2,4,4'-trichloro-2'-hydroxydiphenyl ether) (I), an antimicrobial agent for use with fabrics, was easily chlorinated with sodium hypochlorite to give 2',3,4,4'-tetrachloro-2-hydroxydiphenyl ether (II), 2',4,4',5-tetrachloro-2-hydroxydiphenyl ether (III) and 2',3,4,4',5-pentachloro-2-hydroxydiphenyl ether (IV). Irgasan DP300 and its chlorinated derivatives were readily converted into polychlorinated dibenzo-p-dioxins (PCDDs) by heating: Irgasan DP300 was converted into dichlorodibenzo-p-dioxin(s) (di-CDD, 42%); II into two trichlorodibenzo-p-dioxins (tri-CDDs, 22%) and three tetrachlorodibenzo-p-dioxins (tetra-CDDs, 46%); III into two tri-CDDs (44%), more than two tetra-CDDs (25%) and pentachlorodibenzo-p-dioxin(s) (penta-CDD, 1%); and IV into two tetra-CDDs (16%), trace amounts of penta-CDD(s) and four hexachlorodibenzo-p-dioxins (hexa-CDDs, 40%). Although UV irradiation of Irgasan DP300, II and III gave PCDDs, the amounts of PCDDs formed were much smaller than those obtained by heating. Moreover, PCDD was not detected in the UV irradiation of IV. The identified products suggested that disproportionation of chlorine atom(s) occurred in the photolysis.
益康唑DP300（2,4,4'-三氯-2'-羟基二苯醚）（I）是一种用于织物的抗菌剂，它很容易被次氯酸钠氯化，生成2',3,4,4'-四氯-2-羟基二苯醚（II）、2',4,4',5-四氯-2-羟基二苯醚（III）和2',3,4,4',5-五氯-2-羟基二苯醚（IV）。益康唑DP300及其氯化衍生物通过加热很容易转化为多氯代二苯并对二噁英（PCDDs）：益康唑DP300转化为二氯代二苯并对二噁英（二氯代二噁英，42%）；II转化为两种三氯代二苯并对二噁英（三氯代二噁英，22%）和三种四氯代二苯并对二噁英（四氯代二噁英，46%）；III转化为两种三氯代二苯并对二噁英（44%）、两种以上四氯代二苯并对二噁英（25%）和五氯代二苯并对二噁英（五氯代二噁英，1%）；IV转化为两种四氯代二苯并对二噁英（16%）、痕量五氯代二苯并对二噁英和四种六氯代二苯并对二噁英（六氯代二噁英，40%）。虽然对益康唑DP300、II和III进行紫外线照射会生成PCDDs，但生成的PCDDs量比加热时少得多。此外，在IV的紫外线照射中未检测到PCDD。鉴定出的产物表明，光解过程中发生了氯原子的歧化反应。
