磺化多氯联苯(磺化多氯联苯)是一类新发现的PCB代谢产物。它们首次在北极熊血清中被观察到,最近,在土壤中,以及羟基磺化的多氯联苯。它们在土壤中无处不在,它们估计的物理化学性质在水中显示出高流动性,与母体化合物相比。然而,到目前为止,还没有单一的纯标准,因此它们在环境矩阵中的量化是不准确的。此外,需要纯标准来通过实验确定它们的物理化学性质,以及生态毒理学和毒理学特征。在目前的工作中,探索不同的合成方法,实现了制备多氯联苯单磺酸的挑战性目标,起始材料的选择导致了一个关键点。使用PCB-153(2,2'-4,4'-5,5'-六氯-1,1'-联苯)合成,作为主要物种,一个侧面化合物。相反,使用PCB-155(2,2'-4,4'-6,6'-六氯-1,1'-联苯),一种对称的六氯联苯衍生物,在所有邻位都显示氯原子,得到目标磺化PCB化合物。在这种情况下,磺化通过两步程序成功进行,涉及氯磺酰化和随后的氯磺酰基中间体的水解。
Sulfonated-polychlorinated biphenyls (sulfonated-PCBs) are a newly discovered class of PCB metabolites. They were observed for the first time in polar bear serum and lately, in soil, together with hydroxy-sulfonated-PCBs. Their presence is ubiquitous in soils, and their estimated physical chemical properties show high mobility in water, compared to the parent compounds. However, no single pure standards exist so far and therefore their quantification in the environmental matrices is not accurate. Additionally, pure standards are needed to experimentally determine their physical chemical properties, as well as the ecotoxicological and toxicological characteristics. In the present work, the challenging goal of preparing a polychlorinated biphenyl monosulfonic acid was achieved exploring different synthetic approaches, along which the selection of the starting material resulted in a crucial point. Using PCB-153 (2,2\'-4,4\'-5,5\'-hexachloro-1,1\'-biphenyl) the synthesis afforded, as the major species, a side compound. On the contrary, the use of PCB-155 (2,2\'-4,4\'-6,6\'-hexachloro-1,1\'-biphenyl), a symmetric hexachlorobiphenyl derivative showing chlorine atoms at all the ortho positions, gave the target sulfonated-PCB compound. In this case, sulfonation was successfully carried out through a two-step procedure, involving chlorosulfonylation and the subsequent hydrolysis of the chlorosulfonyl intermediate.