Pentachloronaphthalene appears as pale-yellow to white solid or powder with an aromatic odor. Bp: 327-371°C; mp: 120°C. Density 1.7 g cm-3. Used in lubricants and in the manufacture of insulation for electrical wire. Presents an environmental danger. If released into the environment, bioaccumulation takes place, specifically in fish. Will persist in the environment causing long-term adverse effects. The halowaxes are technical-grade chlorinated naphthalenes containing pentachloronaphthalene in its various isomers together with (mainly) trichloro- tetrachloro- and hexa-chloronapthalenes in their various isomers.
颜色/状态：
White powder
气味：
Aromatic odor
溶解度：
Insoluble (NIOSH, 2016)
蒸汽密度：
Relative vapor density (air = 1): 10.4
蒸汽压力：
< 1 torr at 20 °C
分解：
When heated to decomposition it emits highly toxic fumes of /hydrogen chloride/.
A single oral dose (1 g) of pentachloronaphthalene to rabbits was not metabolised into the phenolic and conjugated urinary metabolites that are common for the lower chlorinated naphthalenes. Moreover, not more than 20 percent of unchanged pentachloronaphthalene was excreted via feces and urine over the 4-day period following dosing, indicating a possible bioaccumulation.
IDENTIFICATION: There are 75 possible congeners of chlorinated naphthalenes. Commercial products are generally mixtures of several congeners and range from thin liquids to hard waxes to high melting point solids. The higher chlorinated naphthalene products have been used as impregnants for condensers and capacitors and dipping encapsulating cmpd in electronic and automotive applications and as temporary binders in the manufacture of ceramic components, in paper coating and in precision casting of alloys, in electroplating, stop-off cmpd, as additive in gear oils and cutting cmpd, in flame proofing and insulation of electrical cable and conductors and moisture proof sealants, as separators in batteries, in refractive index testing oils, masking cmpd in electroplating and in grinding wheel lubricants. HUMAN EXPOSURE: The major sources of release of chlorinated naphthalenes into the environment are likely from waste incineration and disposal of items containing chlorinated naphthalenes to landfill. In the past, chlorinated naphthalene concn of up to 14.5 mg/cu m have been measured in the workplace, while levels of 25-2900 ng/cu m have been recorded in out door air in vicinity of manufacturing sites. More recently, monitoring studies have revealed chlorinated naphthalene concn up to 150 pg/cu m at semirural sites and 1-40 pg/cu m at remote sites. Chlorinated naphthalenes can be absorbed via oral, inhalative and dermal routes, with absorption and distribution over the whole body after oral admin. Chlorinated naphthalenes, especially the dioxin-like congeners, have been detected in adipose tissue, liver, blood and breast milk samples from the general population at concn in the ng/kg lipid range. Severe skin reactions (chloracne) and liver disease have been reported after occupational exposure to chlorinated naphthalenes. Chloracne was common among workers who handling chlorinated naphthalenes in the 1930's to 1940's. A cohort study on workers exposed to chlorinated naphthalenes at a cable manufacturing plant found an excess of deaths from cirrhosis of the liver. However, individuals with chloracne did not show a higher mortality due to liver cirrhosis compared with other workers. The mortality from all cancers was slightly but significantly elevated among all exposed men (standardized mortality ratio =1.18, but was not more elevated in the subcohort with chloracne. This subcohort showed statistically significant excess mortality from cancer of the esophagus and from benign and unspecified neoplasms. Symptoms described in workers exposed to chlorinated naphthalenes included irritation of the eyes, fatigue, headache, anemia, hematuria, impotency, anorexia, vomiting and severe abdominal pain. Halowax 1014 containing penta- and hepta- chloronaphthalenes containing did induce chloracne to individuals after dermal application. The polychlorinated naphthalenes congener/isomer pattern found in human samples was significanntly different from the commercial polychlorinatednaphthalenes mixtures. Two dominating congeners were 1,2,3,5,7/1,2,3,5,6,7-pentachloronaphthalene. ANIMAL STUDIES: Chlorinated naphthalenes can be absorbed via oral, inhalative and dermal routes, with absorption and distribution over the whole body after oral admin. The main target organs are the liver and fat tissue (besides the kidney and lung) showing a high retention, especially for the higher chlorinated congeners The amount of bioaccumulation observed incr with the degree of chlorination of the chlorinated naphthalenes. Elimination of the parent compounds and/or metabolites occurs via feces and urine. Lower chlorinated naphthalenes are less toxic than the higher chlorinated naphthalenes. Long term and carcinogenicity studies with chlorinated naphthalenes have not been performed. Like related cmpd, chlorinated naphthalenes have been demonstrated to be inducers of the cytochrome p450 (CYP) dependent microsomal enzymes. Cattle developed severe systemic disease (bovine hyperkeratosis) during a 5 to 10 day oral exposure of pentachlorinated naphthalenes. Pentachlorinated naphthalenes showed hyperkeratoic activity in the rabbit ear test and in hairless mice. Rats fed a mixture of penta/hexachloronaphthalenes dosed on alternate days for 26 days showed moderate liver changes (swollen and vacuolated liver cells, as well as necrosis and degeneration of scattered cells. Chlorinated naphthalenes were also found to change lipid peroxidation and antioxidant enzyme activities in rats in a manner indicative of oxidative stress. At least some of the biological and toxic responses of chlorinated naphthalenes are believed to be mediated via the cytosolic Ah receptor, resembling those of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) and related cmpd. Short term exposure to higher chlorinated naphthalenes resulted in mortality, liver damage, degeneration of the kidneys etc in rats, rabbits and cattle. Inhalation of a penta/hexachloronaphthalene mixture for 143 days resulted in a slight to moderate histological liver damage in rats. All chlorinated naphthalenes tested cause skin irritations in laboratory animals. Chlorinated napthalenes appear to be of moderate to high acute toxicity to aquatic organisms. /Chlorinated naphthalenes, Halowaxes, Higher Chlorinated Naphthalenes/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
暴露途径
该物质可以通过吸入烟雾和透过皮肤被身体吸收。
The substance can be absorbed into the body by inhalation of fume and through the skin.
来源:ILO-WHO International Chemical Safety Cards (ICSCs)
De Novo Synthesis Mechanism of Polychlorinated Dibenzofurans from Polycyclic Aromatic Hydrocarbons and the Characteristic Isomers of Polychlorinated Naphthalenes
摘要：
Polychlorinated dibenzofurans (PCDFs) and polychlorinated naphthalenes (PCNs) are known to be emitted from municipal waste incinerators (MWIs) with polychlorinated dibenzo-p-dioxins (PCDDs). Two formation paths for PCDD/Fs could mainly work, which are condensation of the precursors such as chlorophenols and "de novo" formation from carbon. However the correlation between the chemical structure of carbon and the resulting PCDD/Fs still remains unknown. In this study, the PCDD/Fs formation from polycyclic aromatic hydrocarbons (PAHs) and CuCl was examined at 400 under 10% O-2. Coronene among the PAHs characteristically gave 1,2,8,9-T4CDF and the derivatives. These isomers clearly indicate that chlorination causes the cleavage of the C-C bonds in a coronene molecule and also that oxygen is easily incorporated from its outside to form 1,2,8,9-T4CDF. The symmetrical preformed structures in the coronene molecule enabled to amplify the de novo formation of the isomer. PCNs are also formed directly from these PAHs. Since there have been few reports on the formation mechanism of PCNs, this study will be a first step to know the whole formation paths. We also define the de novo synthesis as the breakdown reaction of a carbon matrix, since the word has been used without the precise definition.
Emission Factors and Importance of PCDD/Fs, PCBs, PCNs, PAHs and PM<sub>10</sub> from the Domestic Burning of Coal and Wood in the U.K.
作者：Robert G. M. Lee、Peter Coleman、Joanne L. Jones、Kevin C. Jones、Rainer Lohmann
DOI：10.1021/es048745i
日期：2005.3.1
fuels. However, their combined emissions from the domestic burning of coal and wood would contribute only a few percent to annual U.K.emission estimates. Emissions of PAHs and PM10 were major contributors to U.K. national emission inventories. Major emissions were found from the domestic burning for Cl1,2,3DFs, while the contribution of PCDD/F-sigmaTEQ to total U.K.emissions was minor.
本文介绍了当煤和木材经过受控燃烧实验时针对一系列持久性有机污染物（POPs）得出的排放因子（EFs），旨在模拟空间供暖的家庭燃烧。排放了各种各样的持久性有机污染物，煤炭的排放量高于木材的排放量。对于颗粒物，PM10（大约10 g / kg燃料）和多环芳烃（对于sigmaPAHs大约100 mg / kg燃料）获得了最高的EF。对于氯化物，多氯联苯（PCB）的EF最高，而多氯萘（PCN），二苯并-对-二恶英（PCDD）和二苯并呋喃（PCDF）的丰度较低。对于sigmaPCB，EF大约为1000 ng / kg燃料，对于sigmaPCNs大约为100s ng / kg燃料，对于sigmaPCDD / Fs大约为100 ng / kg燃料。该研究证实，一氯化至三氯化二苯并呋喃Cl1,2,3DFs是低温燃烧过程（如煤炭和木材的国内燃烧）的有力指标。结论是，在固体燃料燃烧期间通常形成许多PCB和PC
