Abstract：
Substituted p-phenylenediamines (PPDs), a class of antioxidants, have been widely used to extend the lifespan of rubber products, such as tires and pipes. During use, PPDs will generate their quinone derivatives (PPD-Qs). In recent years, PPDs and PPD-Qs have been detected in the global environment. Among them, N-(1,3-dimethylbutyl)-N\'-phenyl-p-phenylenediamine quinone (6PPD-Q), the oxidation product of N-(1,3-dimethylbutyl)-N\'-phenyl-p-phenylenediamine (6PPD), has been identified as highly toxic to coho salmon, with the lethal concentration of 50 % (LC50) being 95 ng/L, highlighting it as an emerging pollutant of great concern. This review summarizes the physicochemical properties, global environmental distribution, bioaccessibility, potential toxicity, human exposure risk, and green measures associated with PPDs and PPD-Qs. These chemicals exhibit lipophilicity, bioaccumulation potential, and poor aqueous stability. They have been found in water, air, dust, soil, and sediment worldwide, indicating their significance as emerging pollutants. Notably, current studies have identified electronic waste, such as discarded wires and cables, as a non-negligible source of PPDs and PPD-Qs, in addition to tire wear. PPDs and PPD-Qs exhibit strong bioaccumulation in aquatic organisms and mammals, with a tendency for biomagnification within the food web, posing health threats to humans. Available toxicity data indicate that PPDs and PPD-Qs have negative effects on aquatic organisms, mammals, and invertebrates. Acute exposure leads to death and acute damage, while long-term exposure can cause a series of adverse effects, including growth and development toxicity, reproductive toxicity, neurotoxicity, intestinal toxicity, and multi-organ damage. This paper discusses current research gaps and offers recommendations to understand better the occurrence, behavior, toxicity, and environmental exposure risks of PPDs and PPD-Qs.
摘要：
取代的对苯二胺（PPD），一类抗氧化剂，已被广泛用于延长橡胶制品的使用寿命，如轮胎和管道。在使用过程中,PPD将产生它们的醌衍生物(PPD-Qs)。近年来,已经在全球环境中检测到PPD和PPD-Qs。其中,N-(1,3-二甲基丁基)-N'-苯基-对苯二胺醌(6PPD-Q),N-(1,3-二甲基丁基)-N'-苯基-对苯二胺(6PPD)的氧化产物，已被确认对银鲑鱼有剧毒,50％的致死浓度（LC50）为95ng/L，强调它是一种备受关注的新兴污染物。这篇综述总结了物理化学性质，全球环境分布,生物可及性，潜在毒性,人类暴露风险，以及与PPD和PPD-Qs相关的绿色措施。这些化学物质表现出亲脂性，生物累积潜力，和差的水稳定性。它们在水中被发现，空气,灰尘,土壤,和世界各地的沉积物，表明它们作为新兴污染物的重要性。值得注意的是,目前的研究已经确定了电子废物，例如废弃的电线和电缆，作为PPD和PPD-Qs的不可忽略的来源，除了轮胎磨损。PPD和PPD-Qs在水生生物和哺乳动物中表现出很强的生物蓄积性，随着食物网内生物放大的趋势，对人类健康构成威胁。现有的毒性数据表明，PPD和PPD-Qs对水生生物有负面影响，哺乳动物,和无脊椎动物。急性暴露会导致死亡和急性损伤，虽然长期接触会造成一系列不良影响，包括生长和发育毒性，生殖毒性，神经毒性，肠道毒性，和多器官损伤。本文讨论了当前的研究空白，并提出了更好地理解这种情况的建议，行为，毒性,以及PPD和PPD-Qs的环境暴露风险。
