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. There are no known commercial uses for purified tetrachloronaphthalenes. 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. Predominant cogeners in out door air were tri- and tetrachloronaphthalene. 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. ANIMAL STUDIES: Chlorinated naphthalenes have been shown to be highly bioaccumulative in fish, but less so in shrimp and algae. The amount of bioaccumulation observed incr with the degree of chlorination of the chlorinated naphthalenes. The most highly chlorinated naphthalenes do not appear to bioaccumulate. Chlorinated naphthalene concn in fish range up to a maximum of around 300 ug/kg lipid weight. 1,2,3,4-Tetrachloronaphthalene has demonstrated no mutagenicity. Monitoring studies with seabird eggs have revealed a decr in chlorinated naphthalene levels between 1974 and 1987. Hydroxy metabolites have been identified mostly for the lower chlorinated naphthalenes (mono- to tetra-) in experimental animals. There are also preliminary indications for the occurrence of methylthio- or methyl sulfoxide chloronaphthalene metabolites in the feces of rats. Elimination of the parent compounds and/or metabolites occurs via feces and urine. The higher chlorinated congeners appeared to be more toxic than the lower chlorinated ones. 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. 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. All chlorinated naphthalenes tested cause skin irritations in laboratory animals. Chlorinated napthalenes appear to be of moderate to high acute toxicity to aquatic organisms. Tetra- and pentachloronaphthalene congeners tend to predominate in the biota. /Chlorinated naphthalenes, Tetrachloronaphthalenes and 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)
After chronic oral administration of 1,2,3,4-tetrachloronaphthalene with food to rats, accum in adipose tissue. Concentrations in blood and adipose tissue reached max in first 3 wk and reached equilibrium value within 5 wk.
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.
Degradation of one-side fully-chlorinated 1,2,3,4-tetrachloronaphthalene over Fe–Al composite oxides and its hypothesized reaction mechanism
作者：Yalu Liu、Huijie Lu、Wenxiao Pan、Qianqian Li、Guijin Su、Minghui Zheng、Lirong Gao、Guorui Liu、Wenbin Liu
DOI：10.1039/c7ra01775h
日期：——
aromatic ring, was evaluated over three of the prepared rod-like Fe–Al composite oxides (FeAl-1, FeAl-5 and FeAl-10). The results showed that their reactive activities were in the order of FeAl-5 ≈ FeAl-10 ≫ FeAl-1, which could be attributed to their different pore structural properties and reactive sites caused by the different phase interaction between iron species and the γ-Al2O3. The generation of
在制备的三种棒状Fe-Al复合氧化物（FeAl-1，FeAl- 5和FeAl-10）。结果表明，它们的反应活性约为FeAl-5≈FeAl-10≫ FeAl-1，这可能归因于它们的孔结构性质和反应位点不同，这是由于铁物种与γ-之间的不同相间相互作用引起的。 Al 2 O 3。三氯萘（1,2,3-TrCN和1,2,4-TrCN，即CN-13和CN-14），二氯萘（1,2-DiCN，1,3-DiCN，1,4-DiCN）的生成和2,3-DiCN，即CN-3，CN-4，CN-5和CN-10）和一氯萘（1-MoCN和2-MoCN，即CN-1和CN-2）提示发生了连续的加氢脱氯反应。在三个不同的系统中，CN-14的含量从CN-13的71.5％增至77.7％，这表明在β位置发生了第一个加氢脱氯步骤是优选的。这与八氯萘（CN-75）脱氯过程中在微/纳米Fe 3 O 4上观察到的在α-位置的偏好不同。。一侧和
Regiospecific fragmentation of benzene derivatives: synthetic and analytical applications
作者：Neil J Hales、Harry Heaney、John H Hollinshead、Steven V Ley
DOI：10.1016/0040-4020(95)00395-o
日期：1995.7
The cycloadducts farmed from arenes and tetrachloroand tetrafluorobenzyne have been shown to undergo specific addition-fragmentation reactions. These sequences are both simple syntheses of arenes with unusual substitution patterns and a convenient alternative to the other methods currently available for assaying the isotopic distribution in [14C]-labelled benzene derivatives.
Naphthalene and anthracene nuclei are present in several natural and synthetic compounds. Due to their unique physical and chemical properties, access to functionalized naphthalenes and anthracenes has attracted the attention of both synthetic and medicinal chemists over the decades. In this study, successive Diels–Alder/retro-Diels–Alder reactions of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate with
Poly (Arylene Sulfide) Resin Composition and Production Process Thereof
申请人：Kondo Hidemi
公开号：US20080004375A1
公开（公告）日：2008-01-03
A poly(arylene sulfide) resin composition including 100 parts by weight of a substantially linear straight-chain poly(arylene sulfide) resin, 1 to 50 parts by weight of a branched poly(arylene sulfide) resin having a melt viscosity of 11.0×10
4
to 27.0×10
4
Pa·s as measured at a temperature of 330° C. and a shear rate of 2 sec
−1
, an average particle diameter of 50 to 2,000 μm and a melt viscoelasticity tan δ of 0.10 to 0.30 as measured at a temperature of 310° C. and an angular velocity of 1 rad/sec, and 1 to 400 parts by weight of an inorganic filler, and a production process thereof.
Aryne chemistry. Part XII. Some cycloaddition reactions of tetrachlorobenzyne
作者：H. Heaney、J. M. Jablonski
DOI：10.1039/j39680001895
日期：——
Tetrachlorobenzyne has been generated from pentachlorophenyl-lithium, pentachlorophenylmagnesium chloride, and from tetrachloroanthranilic acid by aprotic diazotisation. Cycloaddition reactions with aromatic compounds occur with high yields.
