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三氯萘 | 1321-65-9

中文名称
三氯萘
中文别名
卤蜡(Β-氯代萘)
英文名称
1,2,3-trichloro-naphthalene
英文别名
1,2,3-trichloronaphthalene;1,2,3-Trichlor-naphthalin
三氯萘化学式
CAS
1321-65-9
化学式
C10H5Cl3
mdl
——
分子量
231.509
InChiKey
QEPTXDCPBXMWJC-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    92.8°C
  • 沸点:
    301.08°C (rough estimate)
  • 密度:
    1.5800
  • 物理描述:
    Trichloronaphthalene is a colorless to pale-yellow solid with an aromatic odor. mp: 93°C; bp: 304-354°C. Used in lubricants and in the manufacture of insulation for electrical wire. Presents an environmental danger. If released into the environment, bioaccumulation takes place in fish. Will persist in the environment causing long-term adverse effects. The halowaxes are technical-grade chlorinated naphthalenes containing trichloronaphthalene in its various isomers together with (mainly) tetrachloro-, pentachloro-, and hexa-chloronapthalenes in their various isomers.
  • 颜色/状态:
    Colorless to pale-yellow solid.
  • 气味:
    Aromatic odor
  • 闪点:
    (200 °C) (OPEN CUP)
  • 溶解度:
    Water solubility: 0.017-0.064 mg/l at 25 °C /Trichloronaphthalene isomers/
  • 蒸汽密度:
    8.0 (Air= 1 at boiling point of trichloronaphthalene)
  • 蒸汽压力:
    LESS THAN 1 TORR @ 20 °C
  • 分解:
    The substance decomposes on heating and on burning producing toxic and corrosive fumes including hydrogen chloride and phosgene.
  • 相对蒸发率:
    Much less than 1. (Butyl Acetate= 1)
  • 保留指数:
    1823.7

计算性质

  • 辛醇/水分配系数(LogP):
    5.1
  • 重原子数:
    13
  • 可旋转键数:
    0
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.0
  • 拓扑面积:
    0
  • 氢给体数:
    0
  • 氢受体数:
    0

ADMET

毒理性
  • 毒性总结
识别:氯代萘共有75种可能的同系物。商业产品通常是几种同系物的混合物,从稀薄液体到硬蜡到高熔点固体不等。高氯代萘产品曾被用作冷凝器和电容器的浸渍剂,在电子和汽车应用中作为浸渍封装化合物,以及在制造陶瓷部件时作为临时粘合剂,在纸张涂层和合金的精密铸造中,在电镀、止焊剂、作为齿轮油和切削液的添加剂,在电线电缆和导体的防火和绝缘以及防潮密封剂中作为隔离剂,在电池中作为分离器,在折射率测试油中,电镀中的遮蔽化合物以及在磨轮润滑剂中。人类暴露:氯代萘进入环境的主要来源可能是废物焚烧和处理含有氯代萘的物品到垃圾填埋场。过去,工作场所中氯代萘的浓度曾达到14.5毫克/立方米,而在制造场地附近室外空气中的水平记录为25-2900纳克/立方米。最近的研究监测表明,在半农村地区氯代萘的浓度高达150皮克/立方米,而在偏远地区的浓度为1-40皮克/立方米。室外空气中的主要同系物是三氯和四氯萘。最近的监测研究氯代萘可以通过口服、吸入和皮肤途径吸收,口服给药后在全身吸收和分布。氯代萘,特别是多氯二苯并对位二噁烷(多氯联苯)样同系物,已经在普通人群的脂肪组织、肝脏、血液和母乳样本中以纳克/千克脂肪的浓度被检测到。职业暴露于氯代萘后报告了严重的皮肤反应(氯痤疮)和肝病。在20世纪30年代至40年代处理氯代萘的工人中氯痤疮很常见。在一项针对电缆制造厂接触氯代萘的工人的队列研究中,发现死于肝硬化的死亡人数过多。然而,与没有氯痤疮的其他工人相比,有氯痤疮的个体并没有显示出更高的因肝硬化死亡的风险。所有接触男性的癌症总死亡率略有但显著升高(标准化死亡率=1.18),但在有氯痤疮的亚队列中并没有更高。这个亚队列显示出食管癌和良性及未指明肿瘤的死亡率有统计学意义的过多。接触氯代萘的工人描述的症状包括眼睛刺激、疲劳、头痛、贫血、血尿、阳痿、厌食、呕吐和严重的腹痛。动物研究:氯代萘在鱼类中已被证明具有高度生物累积性,但在虾类和藻类中则较少。观察到的生物累积量随着氯代萘氯化程度的增加而增加。最高氯代的萘似乎不生物累积。鱼类中氯代萘的浓度高达大约300微克/千克脂肪重量。1,2,3,4-四氯萘在沙门氏菌Ames试验中没有表现出致突变性。对海鸟蛋的监测研究显示,1974年至1987年间氯代萘水平有所下降。羟基代谢物主要在实验动物中为低氯代萘(单体到四体)所识别。还有初步迹象表明,在老鼠的粪便中存在甲基硫代或甲基亚砜氯萘代谢物。父母化合物和/或代谢物的消除通过粪便和尿液进行。较高氯代的同系物似乎比较低氯代的毒性更大。氯代萘的长期和致癌性研究尚未进行。像相关化合物一样,氯代萘已被证明是细胞色素p450(CYP)依赖性微粒体酶的诱导剂。氯代萘还发现会改变大鼠的脂质过氧化和抗氧化酶活性,表现出氧化应激的特征。至少氯代萘的一些生物学和毒性反应被认为是通过细胞质Ah受体介导的,类似于2,3,7,8-四氯二苯并对位二噁烷(TCDD)和相关化合物的反应。所有测试的氯代萘都会在实验室动物中引起皮肤刺激。氯代萘对水生生物的急性毒性似乎为中等至高度。四氯和五氯萘同系物在生物群中往往占主导地位。/氯代萘,更高氯代的萘/
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. Predominant cogners in out door air were tri- and tetrachloronaphthalenes. Recent monitoring studies 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 in the Salmonella Ames test. 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. Longterm 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, 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)
毒理性
  • 暴露途径
吸入,皮肤吸收,吞食,皮肤和/或眼睛接触
inhalation, skin absorption, ingestion, skin and/or eye contact
来源:The National Institute for Occupational Safety and Health (NIOSH)
毒理性
  • 症状
厌食、恶心;眩晕;黄疸、肝脏损伤
anorexia, nausea; dizziness; jaundice, liver injury
来源:The National Institute for Occupational Safety and Health (NIOSH)
毒理性
  • 皮肤症状
Redness.
Redness.
来源:ILO-WHO International Chemical Safety Cards (ICSCs)

安全信息

  • 职业暴露等级:
    B
  • 职业暴露限值:
    TWA: 5 mg/m3 [skin]
  • 立即威胁生命和健康浓度:
    Unknown

制备方法与用途

类别:易燃液体
毒性分级:中毒
可燃性危险特性:易燃;燃烧时产生有毒氯化物气体
储运特性:库房通风、低温干燥
灭火剂:干粉、泡沫、砂土、水
职业标准:TLV-TWA 5 毫克/立方米

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    三氯萘 在 sodium amalgam 、 乙醇 作用下, 生成 2,3-二氯萘
    参考文献:
    名称:
    Armstrong; Wynne, Chemical news and journal of industrial science, 1890, vol. 61, p. 273
    摘要:
    DOI:
  • 作为产物:
    描述:
    苯并[ghi]苝copper(l) chloride 氧气甲烷 作用下, 反应 2.0h, 生成 三氯萘
    参考文献:
    名称:
    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.
    DOI:
    10.1021/es980857k
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文献信息

  • 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
  • The kinetics and mechanisms of aromatic halogen substitution. Part XXV. The chlorination of 2-methylnaphthalene
    作者:G. Cum、P. B. D. de la Mare、J. S. Lomas、M. D. Johnson
    DOI:10.1039/j29670000244
    日期:——
    The chlorination of 2-methylnaphthalene in acetic acid is generally similar to that of naphthalene, in that products of substitution are accompanied by those of addition. The main components of the reaction mixture have been separated, and the structures of a crystalline tetrachloride, m.p. 99–99·5°, and of an acetoxytrichloride, m. p. 130°, have been deduced from studies of their proton magnetic resonance
    2-甲基萘在乙酸中的氯化通常类似于萘的氯化,因为取代的产物伴随着加成的产物。已分离了反应混合物的主要成分,并从对质子磁共振波谱及其质子磁共振光谱的研究中得出了晶体四氯化物的熔点为99-99·5°,乙酰氧基三氯化物的熔点为130°。碱脱氯化氢的行为。将它们的性质与1-氯-2-甲基萘四氯化物(熔点153°)和各种相关化合物的性质进行比较。描述了1,4-二氯-2-甲基萘的合成。
  • 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.
    一种聚芳砜树脂组合物,包括100份重量部的基本线性直链聚芳砜树脂,1至50份重量部的具有在330°C下测得的熔融粘度为11.0×104至27.0×104Pa·s和平均粒径为50至2,000μm以及在310°C下测得的熔融粘弹性tan δ为0.10至0.30的分支聚芳砜树脂,以及1至400份重量部的无机填料,以及其生产工艺。
  • The photochemistry of three tetrachloronaphthalenes
    作者:Peter K. Freeman、Gary E. Clapp、Brian K. Stevenson
    DOI:10.1016/s0040-4039(00)93535-4
    日期:1991.10
    The regiochemistry of the photolysis of three tetrachloronaphthalenes is sharply dependent upon the presence of triethylamine. Analysis of the steady state kinetics in the presence and absence of quenchers and triethylamine provides a mechanistic rationale in terms of triplet, triplet excimer, and singlet exciplex.
    三种四氯萘的光解反应的区域化学反应严重取决于三乙胺的存在。在存在和不存在淬灭剂和三乙胺的情况下,对稳态动力学的分析提供了有关三重态,三重态准分子和单重态激基复合物的机械原理。
  • Verfahren zur Herstellung von hochmolekularen, gegebenenfalls verzweigten Polyarylensulfiden
    申请人:BAYER AG
    公开号:EP0092723A2
    公开(公告)日:1983-11-02
    Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung von hochmolekularen, gegebenenfalls verzweigten Polyarylensulfiden, das dadurch gekennzeichnet ist, daß cyclische phosphororganische Verbindungen als organische Lösungsmittel eingesetzt werden.
    本发明的目的是一种制备高分子量、可选择支化的聚芳基硫醚的工艺,其特点是使用环状有机磷化合物作为有机溶剂。
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