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1,1-二氯乙烷 | 75-34-3

中文名称
1,1-二氯乙烷
中文别名
二氯化乙烯;亚乙基二氯;1,1-二氯乙烷;1,2-二氯乙烷;二氯乙烷;烯虫乙酯;乙叉二氯;对称二氯乙烷;二氯化亚乙基;1,2-二氯化乙烯;;乙撑二氯;1,2-二氯化乙烯;氟利昂150a
英文名称
1,1-dichloroethane
英文别名
dichloroethane
1,1-二氯乙烷化学式
CAS
75-34-3;1300-21-6
化学式
C2H4Cl2
mdl
MFCD00013673
分子量
98.9598
InChiKey
SCYULBFZEHDVBN-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

  • 沸点:
    82-84 °C
  • 密度:
    1.2521 g/cm3(Temp: 204 °C)
  • 介电常数:
    16.7(20.0℃)
  • 物理描述:
    1,1-dichloroethane appears as a colorless liquid with an ether-like odor. Slightly soluble in water and slightly denser than water. Flash point below 70°F. Vapors denser than air. Used to make other chemicals.
  • 颜色/状态:
    Colorless, oily liquid
  • 气味:
    Aromatic ethereal odor
  • 味道:
    As of chloroform
  • 熔点:
    -96.9 °C
  • 闪点:
    -10.0 °C (14.0 °F) - closed cup
  • 溶解度:
    In water, 5,040 mg/L at 25 °C
  • 蒸汽密度:
    3.44 (NTP, 1992) (Relative to Air)
  • 蒸汽压力:
    2.27X10+2 mm Hg at 25 °C
  • 亨利常数:
    0.01 atm-m3/mole
  • 大气OH速率常数:
    2.74e-13 cm3/molecule*sec
  • 稳定性/保质期:

    Stable under recommended storage conditions.

  • 自燃温度:
    458 °C
  • 分解:
    Hazardous decomposition products formed under fire conditions - Carbon oxides, Hydrogen chloride gas.
  • 粘度:
    0.464 mPa s at 25 °C; 0.362 mPa s at 50 °C
  • 腐蚀性:
    Will attack some forms of plastics, rubber, and coatings.
  • 燃烧热:
    -4,774 Btu/lb = -2,652 cal/g = -111X10+5 J/kg
  • 汽化热:
    131.6 Btu/lb = 73.1 cal/g = 3.06X10+5 J/kg
  • 表面张力:
    24.07 mN/m at 20 °C
  • 电离电位:
    11.06 eV
  • 气味阈值:
    Threshold concentration: 120 ppm (no specific isomer); 200 ppm (no specific isomer).
  • 折光率:
    Index of refraction: 1.4167 at 20 °C
  • 相对蒸发率:
    Measured half-life for evaporation from 1 ppm aqueous solution at 25 °C, still air, and an average depth of 6.5 cm: 32 min.
  • 保留指数:
    553;600;585.9;590.6;592.2;593.3;594.2;598.9;601.6;560;564;566;568;570;567.1;568;565.8;568;559;557.8;559;559;563;563

计算性质

  • 辛醇/水分配系数(LogP):
    1.9
  • 重原子数:
    4
  • 可旋转键数:
    0
  • 环数:
    0.0
  • sp3杂化的碳原子比例:
    1.0
  • 拓扑面积:
    0
  • 氢给体数:
    0
  • 氢受体数:
    0

ADMET

代谢
1,1-二氯乙烷在成年小鼠和大鼠最大耐受剂量下慢性口服给药后的代谢研究。大鼠的最大耐受剂量为700 mg/kg,小鼠为1800 mg/kg。动物每周5天,连续4周接受未标记的1,1-二氯乙烷处理,然后单次灌胃给予玉米油中的标记物质。处理后,动物被放置在代谢笼中2天。大鼠以未改变的1,1-二氯乙烷形式排出86%,小鼠排出70%。总代谢(主要是CO2)分别为7.5%和29%,两种物种的代谢产物相似。尽管研究者报告放射性为“结合”,但“结合”可能是由于代谢物而不是由于烷基化。
The metabolism of 1,1-dichloroethane after chronic oral dosing of adult mice and rats at maximum tolerated doses /was studied/. The maximum tolerated dose was 700 mg/kg for rats and 1800 mg/kg for mice. Animals were treated 5 d/wk for 4 wk with unlabeled 1,1-dichloroethane prior to a single gavage dose of labeled material in corn oil. The animals were placed in metabolism cages for 2 d following treatment. Rats excreted 86% as unchanged 1,1-dichloroethane and mice 70%. Total metabolism (primarily CO2) was 7.5 and 29% respectively, and the metabolic products were similar in the two species. Although the investigators report radioactivity as "bound", the "binding" may have been due to incorporation as metabolites rather than due to alkylation.
来源:Hazardous Substances Data Bank (HSDB)
代谢
体外研究表明,很少的1,1-二氯乙烷被代谢。细胞色素P450在代谢过程中似乎扮演着重要角色,而且增加P450的物质的加入会提高1,1-二氯乙烷的代谢。加入谷胱甘肽具有保护作用。
.... In vitro studies confirmed that little 1,1-dichloroethane is metabolized. Cytochrome P450 appears to play a major role in metabolism and the addition of substances that increase P450 increase metabolism of 1,1-dichloroethane. Addition of glutathione had a protective effect.
来源:Hazardous Substances Data Bank (HSDB)
代谢
1,1-二氯乙烷与核酸和蛋白质的共价结合通过给雄性Wistar大鼠和BALBC/c小鼠腹腔注射放射性标记的1,1-二氯乙烷来研究,剂量为每公斤体重127微居里。注射后22小时处死动物,处理肝脏、肾脏、胃和肺,进行DNA、RNA和蛋白质相关的放射性测量。在两种动物的所有检测器官中,RNA结合大于DNA结合。DNA结合最高的平出现在大鼠的胃和小鼠的肝脏。RNA结合在大鼠的肝脏和小鼠的肺中最为显著。
The covalent binding of 1,1-dichloroethane to nucleic acids and protein was investigated by treating male Wistar rats and BALBC/c mice with radiolabeled 1,1-dichloroethane through intraperitoneal doses of 127 uCi/kg body weight. The animals were sacrificed 22 hours postinjection, and the liver, kidneys, stomach, and lungs were were processed for DNA-, RNA-, and protein-associated radioactivity measurements. RNA binding was greater than DNA binding in both species and all organs examined. The highest level of DNA binding occurred in the rat stomach and mouse liver. RNA binding was greatest in rat liver and mouse lung.
来源:Hazardous Substances Data Bank (HSDB)
代谢
1,1-二氯乙烷与肝脏微粒体细胞色素P-450的底物结合位点的结合以及1,1-二氯乙烷对肝脏微粒体中可被一氧化碳抑制的NADPH氧化的刺激作用,可以通过苯巴比妥诱导增强,但不是通过β-萘黄酮诱导增强。将1,1-二氯乙烷与来自经过苯巴比妥处理的朗埃文斯大鼠的肝脏微粒体、NADPH生成系统和EDTA一起孵化,可以将1,1-二氯乙烷转化为乙酸,在较小程度上转化为2,2-二氯乙醇,并且可能还转化为单氯乙酸二氯乙酸。作者得出结论,1,1-二氯乙烷在体外通过肝脏微粒体细胞色素P-450代谢。这种代谢在介导化合物的毒性方面似乎很重要。
The binding of 1,1-dichloroethane to the substrate binding site of hepatic microsomal cytochrome P-450 and the stimulation of hepatic microsomal carbon monoxide-inhibitable NADPH oxidation by 1,1-dichloroethane were enhanced by induction with phenobarbital but not with beta-naphthoflavone. Incubation of 1,1-dichloroethane with hepatic microsomes from phenobarbital-treated Long Evans rats, a NADPH-generating system, and EDTA resulted in the conversion of 1,1-dichloroethane to acetic acid, and to a lesser extent to 2,2-dichloroethanol, and probably also to mono- and dichloroacetic acids. The authors concluded that 1,1-dichloroethane is metabolized by hepatic microsomal cytochrome P-450 in vitro. This metabolism appears important in mediating toxicity of the compound.
来源:Hazardous Substances Data Bank (HSDB)
代谢
氯乙烷对还原代谢的敏感性通过测量在大鼠肝微粒体缺氧孵化过程中每种化合物的消耗量来评估。... 二氯乙烷的代谢速度无法被检测到。...
The susceptibility of polychlorinated ethanes to reductive metabolism was evaluated by measuring the amount of each compound consumed during anaerobic incubations with rat liver microsomes. ... The dichloroethanes were not metabolized at a detectable rate. ...
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 毒性总结
识别和使用:1,1-二氯乙烷是一种无色、油性的液体。它被用作生产氯乙烯1,1,1-三氯乙烷化学中间体。它也是一种谷物熏蒸剂,并有限地用作塑料、油、脂肪、油漆和清漆的溶剂。1,1-二氯乙烷用于制造高真空橡胶和酮润滑脂。该化学品还可以用作抗爆汽油的偶联剂,用于属脱脂、有机合成和矿石浮选。它曾用作麻醉剂,但在这个领域今天已不重要。 人体研究:暴露于该化合物的症状可能包括肝脏和肾脏损害、皮肤和眼睛刺激、皮炎、皮肤烧伤、昏迷、中枢神经系统抑制、嗜睡、恶心、呕吐、晕厥、呼吸道刺激、流涎、打喷嚏、咳嗽、眩晕、流泪、结膜发红、发绀和循环衰竭。 动物研究:在14天的观察期内,家兔皮肤暴露于上限剂量2毫升/千克体重的1,1-二氯乙烷24小时,未观察到毒性效应。在一项对成年雄性大鼠的急性毒性研究中,浓度为8.0克/千克的剂量下有显著死亡率。小鼠腹膜内注射1000毫克/千克未产生肾坏死,但报告了一些管状肿胀的证据。注射2000毫克/千克后尿蛋白增加,注射4000毫克/千克后尿糖增加。大鼠在4000 ppm的浓度下吸入暴露8小时后存活,但在16000 ppm的浓度下死亡。小鼠吸入8000-10000 ppm的1,1-二氯乙烷2小时后观察到麻醉效果,最小致死剂量为17300 ppm。单次腹膜内注射150、300、500和750毫克/千克体重的1,1-二氯乙烷对豚鼠未能引起血清鸟氨酸酶活性的变化,且肝脏未产生组织学变化。怀孕的雌性大鼠在妊娠第6至15天暴露于3800或6000 ppm的1,1-二氯乙烷蒸汽,每天7小时。除了母鼠食物消耗和体重增加略有但统计学上显著的减少,以及胎儿骨骼形成延迟外,母鼠或胎儿没有出现其他影响。没有与暴露相关的畸形效应。一组非怀孕大鼠的肝脏重量因类似暴露而增加,但大体或显微镜下没有明显的组织学变化。长期暴露于1,1-二氯乙烷导致雌性大鼠乳腺腺癌和血管肉瘤的发生率增加,以及小鼠肝细胞癌和良性子宫息肉的发生率增加。1,1-二氯乙烷具有遗传毒性潜力,通过小鼠骨髓染色体畸变和微核形成试验测量。对培养的中国仓鼠卵巢细胞的细胞遗传学效应测试表明,1,1-二氯乙烷诱导了姐妹染色单体交换,但无论是代谢激活与否,都没有引起染色体畸变数量的增加。在沙门氏菌/微粒体试验(Ames试验)中,它不是致突变剂。 生态毒性研究:在实验室实验中评估了一系列乙烯乙烷对杂交杨树(Populus deltoides x nigra DN34)的影响。发现不利影响随着同类乙烯乙烷原子数量的增加而增加。乙烯比类似化的乙烷更具毒性。
IDENTIFICATION AND USE: 1,1-Dichloroethane is a colorless, oily liquid. It is used as a chemical intermediate in the production of vinyl chloride and of 1,1,1-trichloroethane. It is also a grain fumigant and has limited use as a solvent for plastics, oils, fats, paint, and varnishes. 1,1-Dichloroethane is used in the manufacture of high vacuum rubber and silicone grease. The chemical can also be used as a coupling agent in antiknock gasoline, for metal degreasing, organic synthesis, and ore floatation. It was formerly used as an anesthetic but it is of no importance in this field today. HUMAN STUDIES: Symptoms of exposure to this compound may include liver and kidney damage, skin and eye irritation, dermatitis, skin burns, unconsciousness, CNS depression, drowsiness, nausea, vomiting, faintness, irritation of the respiratory tract, salivation, sneezing, coughing, dizziness, lacrimation, reddening of the conjunctiva, cyanosis, and circulatory failure. ANIMAL STUDIES: No toxic effects were observed in rabbits dermally exposed to an upper limit dose of 2 mL 1,1-dichloroethane/kg bw for 24 hr during a 14-day observation period. In a study of acute toxicity to adult male rats, there was significant mortality at a concentration of 8.0 g/kg. Intraperitoneal doses of 1000 mg/kg produced no renal necrosis in mice but some evidence of tubular swelling was reported. Urinary protein was increased after injection of 2000 mg/kg and urinary glucose increased after 4000 mg/kg. Rats survived an 8 hr inhalation exposure to 4000 ppm but were killed at 16,000 ppm. Anesthetic effects in mice that inhaled 8,000-10,000 ppm 1,1-dichloroethane for 2 hours were observed, with a minimal lethal dose of 17,300 ppm. Single intraperitoneal injections of 150, 300, 500, and 750 mg 1,1-dichloroethane/kg bw to guinea pigs failed to elicit a change in serum ornithine carbamoyl transferase activity and produced no histological changes in the liver. Pregnant female rats were exposed on days 6 to 15 of gestation to 3800 or 6000 ppm 1,1-dichloroethane vapors, 7 hr/day. No effect occurred in either the dams or fetuses except for slight but statistically significant decreases in food consumption and weight gain by the dams and delayed ossification in the fetuses. No teratological effects were related to exposures. Liver weights of a group of nonpregnant rats were increased by similar exposure, but no histological changes were apparent grossly or microscopically. Chronic 1,1-dichloroethane exposure led to increased incidence of mammary gland adenocarcinomas and hemangiosarcomas in female rats and an increased incidence of hepatocellular carcinomas and benign uterine polyps in mice. 1,1-Dichloroethane has a genotoxic potential as measured by the bone marrow chromosomal aberrations and micronuclei formation tests in mice. Test for cytogenetic effects in cultured Chinese hamster ovary cells indicated that 1,1-dichloroethane induced sister-chromatid exchanges, but did not cause an increase in the number of chromosomal aberrations either with or without metabolic activation. It was not mutagenic in Salmonella/microsome test (Ames test). ECOTOXICITY STUDIES: Effects of a series of chlorinated ethenes and ethanes on hybrid poplar (Populus deltoides x nigra DN34) were assessed in laboratory experiments. Adverse effects were found to increase with increasing number of chlorine atoms within a homologous series of ethenes or ethanes. Ethenes were more toxic than similarly chlorinated ethanes.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 毒性总结
识别和使用:二氯乙烷最常用于生产氯乙烯单体(1,2-二氯乙烷)。人类研究:对280名接触氯乙烯二氯乙烷的工人进行了实验室调查。检查了一些血液指标和肝功能。报告了一例氯乙烯病,其中氯乙烯二氯乙烷的复合效果明显。在高温条件下给药时,二氯乙烷的急性和亚急性毒性增加。动物研究:没有可用的数据。
IDENTIFICATION AND USE: Dichloroethane is most commonly used in the production of vinyl chloride monomer (1,2-dichloroethane). HUMAN STUDIES: Laboratory investigations were carried out on 280 workers exposed to vinyl chloride and dichloroethane. Some hematological indices and liver function were examined. A case of vinyl chloride disease was reported in which the combined effect of vinyl chloride and dichloroethane was apparent. The acute and subacute toxicity of dichloroethane increased when it was administered under conditions of high temperature. ANIMAL STUDIES: There are no data available.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 毒性总结
关于1,1-二氯乙烷的有限信息表明它可能具有肾毒性、胚胎毒性和可能的致癌性。观察到1,1-二氯乙烷能增强细胞转化,并且结果表明1,1-二氯乙烷或其代谢物能够与细胞大分子如DNA结合。有报道称1,1-二氯乙烷在体内和体外都能与核酸和蛋白质结合。这种结合也由肝脏细胞色素P-450系统介导。苯巴比妥增强共价大分子结合的程度。因此,1,1-二氯乙烷的代谢物会与DNA、RNA和组织蛋白结合。(L403)
The limited information available about 1,1-dichloroethane suggests that it may be nephrotoxic, fetotoxic, and possibly carcinogenic. 1,1-Dichloroethane has been observed to enhance cell transformation and results suggest that 1,1-dichloroethane or a metabolite can bind to cellular macromolecules such as DNA. It had been reported that 1,1-dichloroethane binds to nucleic acids and proteins in vivo and in vitro. This binding is also mediated by the liver cytochrome-P-450 system. Phenobarbital enhances the extent of covalent macromolecular binding. Hence, metabolites of 1,1-dichloroethane bind to the DNA, RNA, and tissue proteins. (L403)
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 致癌性证据
分类:C;可能的人类致癌物。分类依据:基于无人类数据,以及两种动物物种(大鼠和小鼠)有限的致癌性证据,表现为大鼠雌性乳腺腺癌和血管肉瘤的发生率增加,以及小鼠肝细胞癌和良性子宫息肉的发生率增加。人类致癌性数据:无。动物致癌性数据:有限。
CLASSIFICATION: C; possible human carcinogen. BASIS FOR CLASSIFICATION: Based on no human data and limited evidence of carcinogenicity in two animal species (rats and mice) as shown by an increased incidence of mammary gland adenocarcinomas and hemangiosarcomas in female rats and an increased incidence of hepatocellular carcinomas and benign uterine polyps in mice. HUMAN CARCINOGENICITY DATA: None. ANIMAL CARCINOGENICITY DATA: Limited.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 致癌性证据
A4;不可归类为人类致癌物。
A4; Not classifiable as a human carcinogen.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
代烃在生物检测中被发现对B6C3F1小鼠和Osborne-Mendel大鼠具有致癌性(1,2-二氯乙烷),仅对小鼠具有致癌性(1,1,2-三氯乙烷1,1,2,2-四氯乙烷六氯乙烷三氯乙烯四氯乙烯),而对两种物种均无不致癌性。1,1-二氯乙烷1,1,1-三氯乙烷被用来研究肿瘤发生的生化基础。在成年小鼠和大鼠长期口服最大耐受剂量(MTD)和1/4 MTD的每种化合物后进行了研究。...非致癌物1,1-二氯乙烷1,1,1-三氯乙烷在小鼠体内的结合能力比致癌物1,2-二氯乙烷1,1,2-三氯乙烷高2到18倍。...
Chlorinated hydrocarbons /were/ found in a bioassay to be carcinogenic to both B6C3F1 mice and Osborne-Mendel rats (1,2-dichloroethane), carcinogenic only to mice (1,1,2-trichloroethane, 1,1,2,2-tetrachloroethane, hexachloroethane, trichloroethylene, and tetrachloroethylene), and noncarcinogenic to either species. 1,1-Dichloroethane and 1,1,1-trichloroethane were used to investigate the biochemical bases for tumorigenesis. Studies were conducted after chronic oral dosing of adult mice and rats with the MTD and 1/4 MTD of each compound. ... The noncarcinogens 1,1-dichloroethane and 1,1,1-trichloroethane exhibited 2 to 18 times more binding in mice than did the carcinogens 1,2-dichloroethane and 1,1,2-trichloroethane. ...
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
1,1-二氯乙烷可以通过吸入和摄入进入人体。
/1,1-Dichloroethane/ can be absorbed into the body by inhalation and by ingestion.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
1,1-二氯乙烷的血清-空气分配系数(血清中浓度与空气中蒸气浓度的比值)为8。这个值发现与各种卤代烃的阈限值(TLV)的对数之间存在反线性相关性。
The serum-air partition coefficient of 1,1-dichloroethane (ratio of the concentration in serum to the concentration of the vapor in air) had a value of 8. This value was found to fill an inverse linear correlation between the logarithm of the threshold limit value (TLV) for various halogenated hydrocarbons.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
在吸入剂量中,肺部最初吸收了22%的-38标记的1,1-二氯乙烷,1小时后在呼出的空气中排出了这部分。
22% of an inhalation dose of (38)Cl 1,1-dichloroethane initially absorbed by the lung is exhaled in the expired air after 1 hr.
来源:Hazardous Substances Data Bank (HSDB)

安全信息

  • 危险品标志:
    Xn,F,Xi,T
  • 安全说明:
    S16,S23,S26,S36,S36/37,S45,S61,S7
  • 危险类别码:
    R11
  • WGK Germany:
    2,3
  • 包装等级:
    II
  • 危险类别:
    3.1
  • 危险品运输编号:
    UN 2362

SDS

SDS:4c4a3f41c2241f77076a4cabedecc81d
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制备方法与用途

二氯乙烷是一种重要的化工原料和溶剂,具有广泛的用途。但是它也存在一定的危险性和健康危害,以下是对其主要特性的总结:

  1. 物理性质:无色透明油状液体,味甜,易挥发。

  2. 化学稳定性相对较好,但与强氧化剂、碱类不相容。

  3. 可燃性较强,燃点较高。蒸汽比空气重,能沿地面扩散并引起着火或爆炸。

  4. 对皮肤和眼睛有刺激作用,吸入高浓度蒸气可致严重损害甚至死亡。

  5. 可能具有致癌性。

  6. 主要用于生产氯乙烯乙二醇等有机化合物,以及作为溶剂、萃取剂等。

  7. 需要在通风良好的环境中使用,避免长时间接触。

  8. 应远离火源储存和运输。发生火灾时要用干粉或CO2灭火。

  9. 废弃物处理应焚烧或回收利用,以防止环境污染物的生成。

  10. 在农业上可用于熏蒸粮食仓储防虫害等。

总之,虽然二氯乙烷用途广泛,但在使用过程中需严格遵守安全操作规程,采取有效的防护措施,避免对人体和环境造成危害。

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:
    1,1-二氯乙烷甲烷 作用下, 生成 四氯乙烯
    参考文献:
    名称:
    Chlorination of 1, 1-dichloroethane
    摘要:
    公开号:
    US02725412A1
  • 作为产物:
    描述: