环氧氯丙烷 | 106-89-8

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 环烃
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 中文名称: 环氧氯丙烷
• 中文别名: (氯甲基)环氧乙烷；3-氯-1,2-环氧丙烷；1-氯-2,3-环氧丙烷；氯甲代氧丙环；表氯醇；ECH；(±)-环氧氯丙烷
• 英文名称: epichlorohydrin
• 英文别名: 3-chloro-1,2-epoxypropane；2-(chloromethyl)oxirane；(±)-epichlorohydrin；ECH；epichlorohydrine；rac-epichlorohydrin；chloromethyl ethylene oxide；1,2-epoxy-3-chloropropane；epoxychloropropane；epichlorhydrin；epichorohydrin；chloromethyl oxirane
• CAS: 106-89-8
• 化学式: C₃H₅ClO
• mdl: MFCD00005132
• 分子量: 92.5251
• InChiKey: BRLQWZUYTZBJKN-UHFFFAOYSA-N

物化性质

• 熔点：
  -57 °C
• 比旋光度：
  -1～+1°(D/20℃)(c=1,CH3OH)
• 沸点：
  115-117 °C(lit.)
• 密度：
  1.183 g/mL at 25 °C(lit.)
• 蒸气密度：
  3.2 (vs air)
• 闪点：
  93 °F
• 溶解度：
  65.9克/升
• 暴露限值：
  TLV-TWA(skin) 8 mg/m3 (2 ppm) (ACGIH); STEL (15 min) 19 mg/m3 (5 ppm) (NIOSH).
• 介电常数：
  22.9（20℃）
• LogP：
  0.45 at 20℃
• 物理描述：
  1-chloro-2,3-epoxypropane appears as a clear colorless liquid with an irritating chloroform-like odor. Density 9.8 lb / gal. Flash point 87°F. Polymerizable. If polymerization takes place inside a closed container, the container is subject to violent rupture. Irritates the skin and respiratory system. Toxic by ingestion. A confirmed carcinogen. Vapors heavier than air. Used to make plastics and as a solvent.
• 颜色/状态：
  Colorless liquid
• 气味：
  Odor is sweet, pungent or chloroform-like ... generally perceived as a slightly irritating chloroformlike odor
• 蒸汽密度：
  3.29 (EPA, 1998) (Relative to Air)
• 蒸汽压力：
  16.4 mm Hg at 25 °C
• 亨利常数：
  Henry's Law constant = 3.0X10-5 atm-cu m/mole at 25 °C (est)
• 大气OH速率常数：
  4.40e-13 cm3/molecule*sec
• 稳定性/保质期：

  避免与酸类、碱类、氨、胺类、铜、镁铝及其合金接触。

• 自燃温度：
  772 °F (411 °C)
• 分解：
  When heated to decomp, emits toxic fumes of /hydrogen chloride/.
• 粘度：
  0.0103 poise at 25 °C
• 燃烧热：
  -8143 Btu/lb; -4524 Cal/g; -189.4 E+5 J/kg
• 汽化热：
  Latent heat of vaporization: 176 Btu/lb; 97.9 Cal/g; 4.10X10+5 J/kg
• 表面张力：
  37.0 dynes/cm
• 电离电位：
  10.60 eV
• 聚合：
  Can polymerize in presence of strong acids and bases, particularly when hot.
• 气味阈值：
  Odor Threshold Low: 0.08 [mmHg]; Odor Threshold High: 12.0 [mmHg]; Odor threshold from AIHA
• 折光率：
  Index of refraction: 1.44195 at 11.6 °C/D; 1.43969 at 16 °C/D; 1.43585 at 25 °C/D
• 保留指数：
  700 ;708 ;691.7 ;691.5 ;691 ;695 ;708 ;695 ;720 ;700 ;730

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  5
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

... 威斯达大鼠口服或腹腔注射 ... 环氧氯丙烷产生 ... 尿液代谢物 ... 2,3-二羟基丙基-S-半胱氨酸及其N-乙酸盐。由于环氧氯丙烷是一种强亲电子剂，能够与细胞亲核物质反应，因此一些环氧氯丙烷代谢物很可能也以共价键形式结合到各种组织大分子上。

... WISTAR RATS DOSED ORALLY OR IP WITH ... EPICHLOROHYDRIN YIELD ... URINARY METABOLITES ... 2,3-DIHYDROXYPROPYL-S-CYSTEINE & ITS N-ACETATE. SINCE EPICHLOROHYDRIN IS A STRONG ELECTROPHILE THAT IS CAPABLE OF REACTING WITH CELLULAR NUCLEOPHILES, IT IS PROBABLE THAT SOME EPICHLOROHYDRIN METABOLITES ARE ALSO COVALENTLY BOUND TO VARIOUS TISSUE MACROMOLECULES.

来源:Hazardous Substances Data Bank (HSDB)

代谢

给予口服(14)C标记的环氧氯丙烷的大鼠，在3天后处死：38%以二氧化碳形式呼出；50%以代谢物形式在尿液中排出；3%在粪便中排出；其余部分在组织中找到 - 肝脏、肾脏和前胃。

Rats given oral (14)C labeled epichlorhydrin and sacrificed after 3 days: 38% exhaled as carbon dioxide; 50% excreted as metabolites in urine; 3% excreted in the feces; and the remainder was found in the tissues - liver, kidney, and forestomach.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在大鼠口服给药后，(14)C-环氧氯丙烷的主要尿液代谢物以前被识别为N-乙酰-S-(3-氯-2-羟基丙基)-L-半胱氨酸，占给药剂量的36%。在本报告中的一项类似研究中，1,2-二溴-3-氯丙烷被代谢成至少20种放射性尿液代谢物。N-乙酰-S-(3-氯-2-羟基丙基)-L-半胱氨酸只是1,2-二溴-3-氯丙烷的一个次要代谢物（4%）。环氧氯丙烷在大鼠肝脏微粒体体外代谢为α-氯醇，但在类似条件下，1,2-二溴-3-氯丙烷并未代谢为环氧氯丙烷或α-氯醇。对于两种底物，放射性共价结合到肝脏微粒体蛋白的情况都会发生，但(14)C-环氧氯丙烷的结合程度低于(14)C-1,2-二溴-3-氯丙烷。添加3,3,3-三氯丙烯氧化物，一种环氧水解酶的抑制剂，增加了环氧氯丙烷蛋白结合的程度，但减少了结合的(14)C-1,2-二溴-3-氯丙烷的量。数据表明，在大鼠体内和体外，环氧氯丙烷并不是1,2-二溴-3-氯丙烷的一个显著代谢物，也不太可能是1,2-二溴-3-氯丙烷毒性的原因。

The major urinary metabolite of (14)C-epichlorohydrin, after oral administration to rats, was identified previously to be N-acetyl-S-(3-chloro-2-hydroxypropyl)-L-cysteine at 36% of the administered dose. In a similar study reported here, 1,2-dibromo-3- chloropropane was metabolized to at least 20 radioactive urinary metabolites. N-acetyl-S-(3-chloro-2-hydroxypropyl)-L-cysteine was only a minor metabolite (4%) of 1,2-dibromo-3-chloropropane. Epichlorohydrin was metabolized in vitro by rat liver microsomes to alpha-chlorohydrin, but 1,2-dibromo-3-chloroproane was not metabolized to epichlorohydrin or alpha-chlorohydrin under similar conditions. Covalent binding of radioactivity to liver microsomal proteins occurred for both substrates, but was less for (14)C-epichlorohydrin than for (14)C-1,2-dibromo-3-chloropropane. Addition of 3,3,3-trichloropropylene oxide, an inhibitor of epoxide hydrolase, increased the extent of protein binding of epichlorohydrin, but decreased the amojnt of (14)C-1,2-dibromo-3-chloropropane which was bound. The data indicate the epichlorohydrin is not a significant in vivo nor in vitro metabolite of 1,2-dibromo-3-chloropropane in the rat, and is unlikely to be responsible for the toxicity of 1,2-dibromo-3-chloropropane.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在体外研究中，显示环氧氯丙烷在缺乏NADPH的情况下被小鼠肝脏的微粒体环氧化物水合酶（EC 3.3.2.3）水解成3-氯-1,2-丙二醇，蛋白质或谷胱甘肽在这种解毒作用中的角色是不显著的。

In in vitro studies, it was shown that epichlorohydrin was hydrolyzed into 3-chloro-1,2-propanediol by the microsomal epoxide hydrolase(s) (EC 3.3.2.3) of mouse liver in the absence of NADPH, the roles of protein or glutathione in this detoxification being insignificant.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

识别：环氧氯丙烷是一种无色液体，其蒸气在空气中形成爆炸性混合物。燃烧时释放出光气、氯化氢和一氧化碳。酸、腐蚀性溶液和卤化盐会引发聚合反应。该化合物与锌、铝、无水金属卤化物、强酸和碱以及含醇材料反应非常剧烈。在潮湿环境中，环氧氯丙烷对钢具有腐蚀性。环氧氯丙烷有一种类似于氯仿的气味。它可溶于水。环氧氯丙烷用于生产甘油和非改性环氧树脂。它还用于生产弹性体、缩水甘油醚、交联食品淀粉、纸张工业的湿强度树脂、水处理树脂、表面活性剂、离子交换树脂、塑化剂、染料、药品、乳化剂、润滑剂和粘合剂。人类接触：根据环氧氯丙烷的使用模式和其化学物理性质，人类接触主要是职业性的，通过吸入蒸气、直接皮肤接触以及食用食物造成的轻微接触。五名人类志愿者在暴露于环氧氯丙烷蒸气时，阿尔法节律的电压尖峰显示出显著的脑电图变化。报告了眼睛和鼻粘膜的灼烧以及喉咙刺激。描述了七例环氧氯丙烷溅到手上、大腿或脚上的情况。其中两例中环氧氯丙烷与甲醇混合。所有的溢出都导致了持续的化学烧伤，潜伏期在10分钟到几小时之间，然后才出现第一个症状。红斑、肿胀、水肿、侵蚀和溃疡。一名39岁男子吸入少量环氧氯丙烷蒸气的案例报告。最初只有眼睛和喉咙的轻微刺激、头痛、恶心和呕吐；后来发展为慢性哮喘性支气管炎。在2年的多次活检中，发现了肝脏的脂肪变性以及功能紊乱。动物/鱼类/植物/细菌/原生动物/研究：当小鼠的尾巴浸泡在未稀释的环氧氯丙烷中15-60分钟时，大多数死亡，表现出严重的全身中毒。在24小时内，50%的兔子在剃光的皮肤上贴上闭合贴片后死亡。大鼠口服给药后8小时，少于10%的剂量在胃肠道中被回收；雄性在大约2小时后，雌性在大约4小时后达到峰值组织水平。几乎所有的口服环氧氯丙烷都从大鼠的胃肠道中被吸收。被大鼠吸收后，环氧氯丙烷广泛分布到许多组织中。口服后2-4小时血液中环氧氯丙烷的浓度随后在胃和肠、肾脏、前列腺和泪腺以及肝脏中被超过2倍或更多。吸入后，这些水平主要发生在鼻腔 turbinate、泪腺、肾脏、肝脏和大肠的上皮细胞中。在大鼠尿液中已经鉴定出以下代谢物：2,3-二羟基丙基-S-半胱氨酸及其巯基酸、β-氯乙酸钠、草酸和1,3-双巯基丙醇-2-醇。环氧氯丙烷是一种烷基化剂，已经发现在体外与脱氧鸟苷和脱氧腺苷的核酸碱基反应。通过口服、吸入或皮肤接触急性中毒后，死亡原因是呼吸衰竭。在致死剂量下，在鼠标和大鼠的肺、肝、肾、肾上腺和甲状腺中发现了组织病理学变化。大鼠吸入或口服给药后出现急性呼吸刺激、出血和严重水肿。一次sc注射环氧氯丙烷的大鼠在暴露后的前几天表现出近曲小管上皮的肾毒性变性以及皮质坏死的缺血。这一阶段伴有无尿或少尿，然后死亡。还注意到肾功能障碍，如蛋白尿、尿中钠离子浓度增加和血清中钾离子浓度增加。肾组织中细胞色素c-氧化酶、过氧化氢酶、谷氨酸丙酮酸转氨酶的活性受到抑制，而过氧化氢酶活性在尿液中增加。存活大鼠的肾脏再生从暴露后5天开始。在吸入暴露2小时后，在小鼠的肝脏中也发现了轻微的组织学变化，包括增加戊巴比妥睡眠时间以及在大鼠中组胺酶活性的剂量相关降低。在大鼠剃光的背部皮肤上使用棉籽油中的80%环氧氯丙烷溶液进行24小时闭合贴片测试，引起了兔眼角膜损伤。20%的溶液诱导了明确的结膜和睑板刺激伴水肿。在棉籽油中使用5%环氧氯丙烷溶液的24小时闭合贴片测试中，兔子的剃光背部皮肤上看到了严重的皮肤刺激。每组20只雄性Wistar大鼠每周五次通过胃管接受棉籽油中的环氧氯丙烷，持续12周。注意到体重减轻。从第一周开始，时间和剂量相关的变化在胃底细胞层中观察到，如胃壁增厚、出血、增生和增加的有丝分裂体和核数目。12周后，一些大鼠出现了乳头状瘤和鳞状细胞癌。每组30只ICR/H

IDENTIFICATION: Epichlorohydrin is a colorless liquid in which the vapor forms explosive mixtures in air. Phosgene, hydrogen chloride and carbon monoxide are liberated while burning. Acids, caustic solutions and halide salts initiate polymerization reactions. The compound is very reactive with metals such as zinc, aluminum, anhydrous metal halides, strong acids and bases along with alcohol containing materials. In the presence of moisture epichlorohydrin is corrosive to steel. Epichlorohydrin has a chloroform like odor. It is soluble in water. Epichlorohydrin is used for the manufacture of glycerine and unmodified epoxyresins. It is also used in the production of elastomers, glycidil ether, cross linked food starch, wet strength resins for the paper industry, water treatment resins, surfactants, ion exchange resins, plasticizers, dyestuffs, pharmaceutical products, emulsifiers, lubricants and adhesives. HUMAN EXPOSURE: On the basis of use patterns and the chemical and physical properties of epichlorohydrin, human exposure is mainly occupational, through vapor inhalation, direct skin contact and a slight exposure resulting from food consumption. Five human volunteers showed significant electroencephalogram changes in the voltage spikes of the alpha rhythm when they were exposed to a vapor of epichlorohydrin. Burning of the eyes and nasal mucosa was reported along with throat irritation. Seven cases of epichlorohydrin spills on the hands, thighs or feet have been described. In two cases epichlorohydrin was mixed with methanol. All spills resulted in protracted chemical burns with a latent period of between 10 minutes and several hours before the first symptoms appeared. Redness, swelling, edema, erosion and ulceration. One case was reported of a 39 year old man who inhaled a few deep breaths of epichlorohydrin vapor occured. Initially only a slight irritation of the eyes and throat was experienced with headache, nausea and vomiting; later chronic asthmatic bronchitis developed. Several biopsies over 2 yr period showed fatty degeneration together with functional disturbances of the liver. ANIMAL/FISH/PLANT/BACTERIAL/ PROTOZOAN/ STUDIES: When the tails of mice were immersed in undiluted epichlorohydrin for 15-60 minutes, most died exhibiting severe systemic poisoning. Within 7 days, 50% of the rabbits died after the application of epichlorohydrin on an occluded patch of shaved skin for 24 hr. Eight hours after oral administration of epichlorohydrin to rats less than 10% of the dose was recovered in the gastrointestinal tract; peak tissue levels occurred approximately 2 hr after dosing in the males and 4 hr in the females. Almost all orally ingested epichlorohydrin was absorbed from the gastrointestinal tract of rats. After absorption by rats, epichlorohydrin was distributed widely through out many tissues. Concentrations of epichlorohydrin found in the blood, 2-4 hr after oral ingestion were subsequently exceeded by a factor of 2 or more in the stomach and intestines, kidneys, prostate and lacrimal glands and the liver. Directly after inhalation, such levels occurred mainly in the epithelium of the nasal turbinates, lacrimal glands, kidneys, liver and large intestine. The following metabolites have been identified in the urine of rats: 2,3-dihydroxypropyl-S-cysteine and its mercapturic acid, beta-chloroacetic acid, oxalic acid and 1,3-bis-mercaptylpropanol-2-ol. Epichlorohydrin is an alkylating agent and has been found to react with nucleic acid bases deoxyguanosine and deoxyadenosine in vitro. After acute intoxication through oral, inhalation or skin exposure death was due to respiratory failure. At lethal doses, histopathological changes were found in the lungs, liver, kidneys, adrenals and thyroid gland of mice and rats. Acute respiratory irritation with hemorrhage and severe edema occurred in rats after inhalation or oral dosing. Rats injected once sc with epichlorohydrin showed nephrotoxic degeneration of the epithelium of the proximal tubules with ischemic cortex necrosis in the first days after exposure. This phase was accompanied by anuria or oliguria then death. Renal insufficiency was noted along with functional disturbances such as proteinuria, increased sodium ion concentration in the urine and an increased potassium ion concentration in the serum. The activity of the enzymes cytochrome c-oxidase, catalase, glutamic pyruvic transaminase and to a lesser extent alkaline phosphatase and glutamic oxaloacetic transaminase was inhibited in renal tissue, while catalase activity was increased in the urine. Regeneration of the kidneys in surviving rats started 5 days after exposure. Slight histological liver changes were also found in mice after 2 hr inhalation exposure to epichlorohydrin which included increased pentobarbital sleeping time in mice and a dose related decrease in histaminases activity in rats. Application of 80% solution epichlorohydrin in cottonseed oil caused corneal damage in the rabbit eye. A 20% solution induced definitive conjunctival and palpebral irritation with edema. Severe skin irritation was seen in a 24 hr occluded patch test on the shaved back of rabbits using a 5% solution of epichlorohydrin in cotton seed oil. Groups of 20 male Wistar rats received epichlorohydrin in water by stomach tube five times a week for 12 weeks. Reduced body weight was noted. From the first week onwards, time and dose related increase was observed in the changes in the basal cell layer of the forestomach such as thickening of the stomach wall, hemorrhaging, hyperplasia and increased number of mitotic figures and nuclei. After 12 weeks some of the rats had papillomas and squamous cell carcinomas. Each group of 30 female ICR/HCA Swiss mice received an ip dose of epichlorohydrin in tricaprylin once a week for up to 450 rats. A group of 100 mice did not receive any treatment and a group of 50 mice received the vehicle only. Papillary tumors were observed in the lungs of 11 exposed mice and 10 vehicle control mice. A group of 40 C3H mice was painted three times a week with a brushful of undiluted epichlorohydrin on the clipped midline of the back for up to 25 months. At month 17, 30 mice were alive and at moth 24 only 1 . No tumors were found. Female rats received orally epichlorohydrin in cotton seed oil between the 6th and 15th day of pregnancy. Higher dose levels were toxic to the dams, no embryotoxic, fetotoxic or teratogenic effects were observed. Similar negative results were obtained when female rats and rabbits inhaled vapors of epichlorohydrin 7 hr/day between the 6th and 15th or the 18th day of pregnancy. Epichlorohydrin is acutely toxic to blue and green algae, bacteria, crustacea and fish.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

癌症分类：B2组可能的人类致癌物

Cancer Classification: Group B2 Probable Human Carcinogen

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

分类：B2；可能的人类致癌物。分类依据：人类数据不足。在大鼠和小鼠中通过不同途径给予环氧氯丙烷的多个研究显示阳性结果。由于环氧氯丙烷是一种强烈的烷基化剂，在应用部位会产生肿瘤。人类致癌性数据：不足。动物致癌性数据：充分。

CLASSIFICATION: B2; probable human carcinogen. BASIS FOR CLASSIFICATION: Human data are inadequate. Multiple studies in rats and mice administered epichlorohydrin by various routes were positive. As epichlorohydrin is a strong alkylating agent, tumors are produced at the site of application. HUMAN CARCINOGENICITY DATA: Inadequate. ANIMAL CARCINOGENICITY DATA: Sufficient.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

评估：对于环氧氯丙烷在人类中的致癌性，证据不足。在实验动物中，对于环氧氯丙烷的致癌性有足够的证据。总体评估：环氧氯丙烷可能对人类致癌（2A组）。在进行总体评估时，工作组考虑到了环氧氯丙烷已知的化学活性及其在广泛遗传测试中的直接作用。

Evaluation: There is inadequate evidence in humans for the carcinogenicity of epichlorohydrin. There is sufficient evidence in experimental animals for the carcinogenicity of epichlorohydrin. Overall evaluation: Epichlorohydrin is probably carcinogenic to humans (Group 2A). In making the overall evaluation, the Working Group took into consideration the known chemical reactivity of epichlorohydrin and its direct activity in a wide range of genetic tests.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

A3：已确认的动物致癌物，对人类的相关性未知。

A3: Confirmed animal carcinogen with unknown relevance to humans.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

除胰腺外，观察到组织分布与靶器官毒性之间的相关性。主要通过尿液排泄。在雄性和雌性大鼠中，分别有21%和18%的剂量以二氧化碳形式排泄。女性的组织峰值水平较低。

WITH EXCEPTION OF PANCREAS, A CORRELATION OBSERVED BETWEEN TISSUE DISTRIBUTION & TARGET ORGAN TOXICITY. EXCRETION MAINLY IN URINE. 21 & 18% OF DOSE EXCRETED AS CO2 IN MALE & FEMALE RATS. PEAK TISSUE LEVELS IN FEMALES LOWER.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

环氧氯丙烷可能通过皮肤被吸收。

/EPICHLOROHYDRIN MAY BE/ ABSORBED THROUGH THE SKIN.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

Fischer F344雄性大鼠的上呼吸道通过手术被孤立出来，并与一个特殊设计的流动系统相连接。上呼吸道和下呼吸道的气管连接被切断。在上呼吸道中，大鼠自然地从气流中呼吸，同时暴露于丙二醇单甲醚、丙二醇单甲醚乙酸酯、环氧氯丙烷等化合物蒸汽中。完整的大鼠仅通过鼻子暴露于相同的化合物，并确定蒸汽吸收的百分比以进行比较。尝试将结果与化合物的水溶性相关联。数据与两室数学模型的预测进行了比较。通过孤立的上呼吸道，超过50至70%的环氧氯丙烷蒸汽被吸收。除了苯乙烯和二氯甲烷外，上呼吸道吸收的蒸汽百分比接近下呼吸道和仅鼻子暴露的动物观察到的百分比。上呼吸道的吸收与水溶性之间没有相关性。数学模型通常准确地预测了下呼吸道和完整动物对蒸汽的吸收。然而，模型严重低估了上呼吸道对环氧氯丙烷的吸收。/结果表明/，血液空气分配可以解释上呼吸道对化学物质的吸收，但只有在考虑其他代谢和生理参数的情况下才能如此。

The upper respiratory tracts of male Fischer F344 rats were surgically isolated and connected to a specially designed flow system. The tracheal connection of the upper respiratory tract and the lower respiratory tract was interrupted. The upper respiratory tract was exposed to propylene-glycol- monomethyl ether, propylene glycol monomethyl ether acetate, epichlorohydrin, cmpd which include vapors while the rat spontaneously breathed from a stream of air. Intact rats were exposed nose only to the same compound and the percentages of vapor absorbed were determined for comparison purposes. Attempts were made to correlate the results with the water solubility of the compounds. The data were compared to predictions of two compartment mathematical models. More than 50 to 70% of the epichlorohydrin, vapors passing through the isolated upper respiratory tacts were absorbed. With the exception of styrene and methylene chloride, the percentage of vapors absorbed by the upper respiratory tract approximated that observed in the lower respiratory tract and nose only exposed animals. There was no correlation between absorption in the URT and water solubility. The mathematical models generally predicted the absorption of vapors by the lower respiratory tract and intact animals accurately. The models seriously underestimated absorption of epichlorohydrin, by the upper respiratory tract. /Results indicate/ that blood air partitioning can account for absorption of chemicals by the upper respiratory tract, but only if other metabolic and physiological parameters are considered.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在啮齿动物中，经吸入后鼻腔中的含量最高，经口服后胃中的含量最高。在大鼠中，无论暴露途径如何，大部分吸收的环氧氯丙烷都会迅速代谢，一部分以二氧化碳的形式通过肺部排出，另一部分以水溶性化合物的形式通过尿液排出。

The highest tissue concentrations in rodents were found in the nose after inhalation, and in the stomach after ingestion. In rats, regardless of the route of exposure, most absorbed epichlorohydrin is metabolized rapidly, part being excreted as carbon dioxide via the lungs and part as water-soluble compounds via the urine.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险等级：
  6.1
• 立即威胁生命和健康浓度：
  75 ppm
• 危险品标志：
  T
• 安全说明：
  S45,S53
• 危险类别码：
  R43,R10,R45,R23/24/25,R34
• WGK Germany：
  3
• 海关编码：
  2932999099
• 危险品运输编号：
  UN 2023
• 危险类别：
  6.1
• RTECS号：
  TX4900000
• 包装等级：
  II
• 储存条件：
  1. 储存于阴凉、通风的库房，远离火种与热源，库温不宜超过30℃。应将酸类、碱类及食用化学品分开存放，严禁混储。使用防爆型照明和通风设施，并禁止使用易产生火花的机械设备和工具。储存区需配备泄漏应急处理设备和合适的收容材料。 2. 为防止环氧氯丙烷发生自聚反应，建议将其存放在干燥清洁的镀锌铁桶中，每桶重量不超过200kg。应储存在阴凉、通风且干燥的地方，并远离火源与热源。按易燃有毒物品的规定进行储存和运输。

SDS

第一部分：化学品名称

化学品中文名称：	3-氯-1，2-环氧丙烷；环氧氯丙烷
化学品英文名称：	3-Chloro-1，2-epoxypropane；Epichlorohydrin
中文俗名或商品名：
Synonyms：
CAS No.：	106-89-8
分子式：	C 3 H 5 ClO
分子量：	92.52

第二部分：成分/组成信息

纯化学品 混合物

化学品名称：3-氯-1，2-环氧丙烷；环氧氯丙烷

有害物成分 含量 CAS No.

第三部分：危险性概述

危险性类别：	第6．1类 毒害品
侵入途径：	吸入 食入 经皮吸收
健康危害：	蒸气对呼吸道有强烈刺激性。反复和长时间吸入能引起肺、肝和肾损害。高浓度吸入致中枢神经系统抑制可致死。蒸气对眼有强烈刺激性，液体可致眼灼伤。皮肤直接接触液体可致灼伤。口服引起肝、肾损害，可致死。慢性中毒：长期少量吸入可出现神经衰弱综合征和周围神经病变。
环境危害：
燃爆危险：

第四部分：急救措施

皮肤接触：	脱去污染的衣着，立即用大量流动清水彻底冲洗至少15分钟。就医．
眼睛接触：	立即翻开上下眼睑，用流动清水或生理盐水冲洗至少15分钟。就医。
吸入：	迅速脱离现场至空气新鲜处。保持呼吸道通畅。呼吸困难时给输氧。呼吸停止时，立即进行人工呼吸。就医。
食入：	立即用水漱口，给饮牛奶或蛋清。就医。

第五部分：消防措施

危险特性：	其蒸气与空气形成爆炸性混合物，遇明火、高温能引起分解爆炸和燃烧。若遇高热可发生剧烈分解，引起容器破裂或爆炸事故。
有害燃烧产物：
灭火方法及灭火剂：	泡沫、二氧化碳、干粉、砂土。
消防员的个体防护：
禁止使用的灭火剂：
闪点(℃)：	34
自燃温度(℃)：	引燃温度(℃)：无资料
爆炸下限[%(V/V)]：	3．8
爆炸上限[%(V/V)]：	21
最小点火能(mJ)：
爆燃点：
爆速：
最大燃爆压力(MPa)：
建规火险分级：

第六部分：泄漏应急处理

应急处理：

疏散泄漏污染区人员至安全区，禁止无关人员进入污染区，切断火源。应急处理人员戴自给式呼吸器，穿防护服。不要直接接触泄漏物，在确保安全情况下堵漏。喷水雾可减少蒸发。用砂土或其它不燃性吸附剂混合吸收，然后收集运至废物处理场所。如大量泄漏，利用围堤收容，然后收集、转移、回收或无害处理后废弃。

第七部分：操作处置与储存

操作注意事项：
储存注意事项：

第八部分：接触控制/个体防护

最高容许浓度：	中 国 MAC：1mg／m3[皮] 前苏联MAC：1mg／m3 美国TLV—TWA：A
监测方法：
工程控制：	密闭操作，全面排风。
呼吸系统防护：	空气中浓度超标时，戴面具式呼吸器。紧急事态抢救或撤离时，建议佩戴自给式呼吸器。
眼睛防护：	戴化学安全防护眼镜。
身体防护：	穿紧袖工作服，长筒胶鞋。
手防护：	戴防化学品手套。
其他防护：	工作后，淋浴更衣。保持良好的卫生习惯。防止皮肤和粘膜的损害。

第九部分：理化特性

外观与性状：	无色油状液体，有氯仿样刺激气味。
pH：
熔点(℃)：	-25．6
沸点(℃)：	117．9
相对密度(水=1)：	1．18(20℃)
相对蒸气密度(空气=1)：	3．29
饱和蒸气压(kPa)：	1．8(20℃)。
燃烧热(kJ/mol)：
临界温度(℃)：
临界压力(MPa)：
辛醇/水分配系数的对数值：
闪点(℃)：	34
引燃温度(℃)：	引燃温度(℃)：无资料
爆炸上限%(V/V)：	21
爆炸下限%(V/V)：	3．8
分子式：	C 3 H 5 ClO
分子量：	92.52
蒸发速率：
粘性：
溶解性：	微溶于水，可混溶于醇、醚、四氯化碳、苯。
主要用途：	用于制环氧树脂，也是一种含氧物质的稳定剂和化学中间体。

第十部分：稳定性和反应活性

稳定性：	在常温常压下 稳定
禁配物：	酸类、碱类、氨、胺类、铜、镁、铝和它们的合金。
避免接触的条件：
聚合危害：	能发生
分解产物：	一氧化碳、二氧化碳、氯化氢。

第十一部分：毒理学资料

急性毒性：	LD50: 90mg／kg(大鼠经口)；238mg/kg(小鼠经口)；1500mg／kg(兔经皮) LC50：500ppm，4小时(大鼠吸入)
急性中毒：
慢性中毒：
亚急性和慢性毒性：
刺激性：
致敏性：
致突变性：
致畸性：
致癌性：

第十二部分：生态学资料

生态毒理毒性：
生物降解性：
非生物降解性：
生物富集或生物积累性：

第十三部分：废弃处置

废弃物性质：
废弃处置方法：
废弃注意事项：

第十四部分：运输信息

危险货物编号：
UN编号：	2023
包装标志：
包装类别：	Ⅱ
包装方法：
运输注意事项：	储存于阴凉、通风仓间内。远离火种、热源。仓温不宜超过30℃。防止阳光直射。包装要求密封，不可与空气接触。应与氧化剂、酸类、碱类分开存放。储存间内的照明、通风等设施应采用防爆型。罐储时要有防火防爆技术措
RETCS号：
IMDG规则页码：

第十五部分：法规信息

国内化学品安全管理法规：
国际化学品安全管理法规：

第十六部分：其他信息

参考文献：	1.周国泰，化学危险品安全技术全书，化学工业出版社，1997 2.国家环保局有毒化学品管理办公室、北京化工研究院合编，化学品毒性法规环境数据手册，中国环境科学出版社.1992 3.Canadian Centre for Occupational Health and Safety,CHEMINFO Database.1998 4.Canadian Centre for Occupational Health and Safety, RTECS Database, 1989
填表时间：	年月日
填表部门：
数据审核单位：
修改说明：
其他信息：	4
MSDS修改日期：	年月日

制备方法与用途

环氧氯丙烷是一种重要的有机化工原料,具有广泛的应用领域。根据提供的信息，以下是对其主要性质、用途和生产方法的总结:

化学性质:

• 无色油状液体,有类似氯仿的气味。
• 易燃。
• 微溶于水,与多数有机溶剂混溶。

主要用途:

1. 制备甘油及缩水甘油衍生物
2. 生产环氧树脂、氯醇橡胶等高分子材料
3. 合成聚醚多元醇
4. 用作有机合成原料
5. 溶剂(如用于树脂、树胶、纤维素醚的溶解)
6. 增塑剂
7. 表面活性剂

生产方法:

主要采用丙烯氯化法制备,具体步骤包括:

1. 丙烯氯化生成氯丙烯
2. 氯丙烯与次氯酸反应得到2,3-二氯丙醇和1,2-二氯丙醇混合物
3. 将该混合物皂化制得环氧氯丙烷

物理化学性质:

• 熔点: -64.5°C
• 沸点: 97.8°C
• 相对密度(水=1): 1.207
• 蒸汽压: 30.3 mmHg at 20°C

安全与环境:

• 高毒,急性毒性口服LD50为大鼠90 mg/kg、小鼠195 mg/kg
• 易燃,遇明火可燃烧并产生有毒烟雾
• 应低温密闭储存于阴凉处,避免氧化剂接触

职业卫生标准:

• 时间加权平均容许浓度(TWA): 10 mg/m³
• 短时间暴露极限(STEL): 20 mg/m³

总之,环氧氯丙烷是一种多功能的化工原料,在多个领域都有重要应用,但同时也需注意其易燃性和毒性。

反应信息

• 作为反应物：
  描述：

  环氧氯丙烷 在 potassium hydrogen bifluoride 作用下， 以 二乙二醇 为溶剂， 反应 2.5h， 生成 1,3-二氟-2-丙醇
  参考文献：
  名称：

  萤光素的形成和转化的研究II。氨基醇的合成和酯化

  摘要：

  描述了单氟化氨基醇（具有伯，仲和叔氨基以及还具有季铵基）及其磷酸酯和酸性酯的合成。

  DOI：

  10.1002/hlca.19600430425
• 作为产物：
  描述：

  甘油 在 盐酸 、 溶剂黄146 、 sodium hydroxide 作用下， 以 水 为溶剂， 70.0~120.0 ℃ 、101.33 kPa 条件下， 生成 环氧氯丙烷
  参考文献：
  名称：

  METHOD FOR PREPARING CHLOROHYDRINS COMPOSITION AND METHOD FOR PREPARING EPICHLOROHYDRIN USING CHLOROHYDRINS COMPOSITION PREPARED THEREBY

  摘要：

  提供了一种制备氯水合物组合物的方法以及利用该方法制备环氧氯丙烷的方法。制备氯水合物组合物的方法包括在催化剂存在下，将多羟基脂肪烃类烃烃基化试剂反应，包括按照规定顺序执行至少一个系列单元操作的组合，其中该方法还包括混合从最终反应步骤排放的反应混合物经纯化得到的氯水合物浓缩物和从脱水步骤排放的富水层。制备环氧氯丙烷的方法包括将通过制备氯水合物组合物的方法制备的氯水合物组合物与碱性试剂接触。

  公开号：

  US20130102799A1
• 作为试剂：
  描述：

  4-硝基苯乙烯 、 1,2,3,4,5-pentachloro-5-methyl-1,3-cyclopentadiene 在 对苯二酚 、 环氧氯丙烷 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以75%的产率得到(1RS,5RS,7SR)-1,2,3,4,7-pentachloro-7-methyl-5-(4-nitrophenyl)bicyclo[2.2.1]hept-2-ene
  参考文献：
  名称：

  重新审视超氧化物化学：四氯取代的亚甲基正三环烯的合成。

  摘要：

  据报道，超氧离子的意外反应性通过其双重作用模式导致四氯芳基/乙烯基取代的去三环烯的合成。人们发现 KO2 比其他常规碱更优越，并且是唯一能够进行此类反应的试剂。添加抗氧化剂 BHT（2,6-二叔丁基-4-甲基苯酚）提高了亚甲基正三环烯的产率。在 DMSO-d 6 中的超氧化物介导的反应中观察到氘的完全掺入。3-亚甲基降冰片烯的弗里德-克来福特酰化反应产生 2-丙酮取代的五氯降冰片烯。

  DOI：

  10.3762/bjoc.10.264

文献信息

• Facile Room-Temperature MgBr₂· OEt₂-Catalyzed Thiolysis of Epoxides Under Solvent-Free Conditions
  作者：Mohammad M. Mojtahedi、M. Saeed Abaee、Mohammad Bolourtchian、Hassan Abbasi

  DOI：10.1080/10426500601088697

  日期：2007.2.15

  Solvent-free ring opening of 1,2-epoxides with aromatic and aliphatic thiols under 1 mol% magnesium bromide ethyl etherate catalysis affords rapid formation of β-hydroxy sulfides at ambient temperature with excellent yields. Nucleophilic attack of the thiols occurs regioselectively at the less hindered position of the epoxides.

  在 1 mol% 溴化镁乙基醚合物催化下，1,2-环氧化物与芳香族和脂肪族硫醇的无溶剂开环可在环境温度下以优异的产率快速形成 β-羟基硫化物。硫醇的亲核攻击区域选择性地发生在环氧化物的受阻较小的位置。
• Cell adhesion-inhibiting antiinflammatory and immune-suppressive compounds
  申请人：Abbott Laboratories

  公开号：US20040116518A1

  公开（公告）日：2004-06-17

  The present invention relates to novel cinnamide compounds that are useful for treating inflammatory and immune diseases and cerebral vasospasm, to pharmaceutical compositions containing these compounds, and to methods of inhibiting inflammation or suppressing immune response in a mammal.

  本发明涉及新型肉桂酰胺化合物，用于治疗炎症和免疫性疾病以及脑血管痉挛，以及含有这些化合物的药物组合物，以及在哺乳动物中抑制炎症或抑制免疫反应的方法。
• Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20150231142A1

  公开（公告）日：2015-08-20

  The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

  本发明涉及含有上皮钠通道活性抑制剂与至少一种ABC转运蛋白调节剂化合物（A式、B式、C式或D式）的药物组合物。该发明还涉及这些药物配方，以及使用这些组合物治疗CFTR介导的疾病，特别是囊性纤维化的方法。
• Alumina-supported Molybdenum (VI) Oxide: An Efficient and Recyclable Heterogeneous Catalyst for Regioselective Ring Opening of Epoxides with Thiols, Acetic Anhydride, and Alcohols under Solvent-free Conditions
  作者：Sweety Singhal、Suman L. Jain、Bir Sain

  DOI：10.1246/cl.2008.620

  日期：2008.6.5

  An efficient and simple protocol for regioselective ring opening of epoxides with thiols, acetic anhydride, and alcohols using 16 wt % MoO3 supported on alumina as a recyclable catalyst is described.

  描述了使用负载在氧化铝上的 16 wt% MoO3 作为可回收催化剂的硫醇、乙酸酐和醇区域选择性开环环氧化物的有效且简单的方案。
• [EN] OXAZOLE DERIVATIVES USEFUL AS INHIBITORS OF FAAH<br/>[FR] DÉRIVÉS D'OXAZOLE UTILES COMME INHIBITEURS DE FAAH
  申请人：MERCK & CO INC

  公开号：WO2010017079A1

  公开（公告）日：2010-02-11

  The present invention is directed to certain oxazole derivatives which are useful as inhibitors of Fatty Acid Amide Hydrolase (FAAH). The invention is also concerned with pharmaceutical formulations comprising these compounds as active ingredients and the use of the compounds and their formulations in the treatment of certain disorders, including osteoarthritis, rheumatoid arthritis, diabetic neuropathy, postherpetic neuralgia, skeletomuscular pain, and fibromyalgia, as well as acute pain, migraine, sleep disorder, Alzeimer Disease, and Parkinson's Disease.

  本发明涉及某些噁唑衍生物，其可用作脂肪酸酰胺水解酶（FAAH）的抑制剂。该发明还涉及包含这些化合物作为活性成分的药物配方，以及这些化合物及其配方在治疗某些疾病中的使用，包括骨关节炎、类风湿性关节炎、糖尿病神经病变、带状疱疹后神经痛、骨骼肌肉疼痛和纤维肌痛，以及急性疼痛、偏头痛、睡眠障碍、阿尔茨海默病和帕金森病。

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