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Trichlorethylene 79-01-6
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Trichlorethylene (IUPAC), CHClCCl2, is a stable, low boiling point, colorless liquid with a chloroform-like odor. It will not corrode ordinary metals even when wet. Slightly soluble in water, non-flammable. Toxic if inhaled, TLV in air is 50 ppm, IDLH is 1000 ppm. The FDA has banned its use in food, drugs and cosmetics. The four-digit UN identification number is 1710. NFPA 704 designates Health 2, Flammability 1, and Reactivity 0. Its main uses are for metal degreasing, dry cleaning, as a refrigerant and fumigant, and for drying electronic components.
| describe | Trichlorethylene (IUPAC), CHClCCl2, is a stable, low boiling point, colorless liquid with a chloroform-like odor. It will not corrode ordinary metals even when wet. Slightly soluble in water, non-flammable. Toxic if inhaled, TLV in air is 50 ppm, IDLH is 1000 ppm. The FDA has banned its use in food, drugs and cosmetics. The four-digit UN identification number is 1710. NFPA 704 designates Health 2, Flammability 1, and Reactivity 0. Its main uses are for metal degreasing, dry cleaning, as a refrigerant and fumigant, and for drying electronic components. |
| chemical properties | Trichlorethylene (TCE) is a clear, colorless, nonflammable (at room temperature) stable toxic liquid with a chloroform-like odor (ATSDR, 2011). It is slightly soluble in water, soluble in fats and oils and common organic solvents, and has a boiling point of 87°C (190 F). On contact with air, it slowly decomposes to form phosgene, hydrogen chloride and dichloroacetyl chloride. Trichlorethylene becomes corrosive in contact with water and forms dichloroacetic acid and hydrochloric acid. Soluble in methanol, ether and acetone.  Trichlorethylene is also known as trichlorethylene, acetylene trichloride, 1-chloro-2,2-dichloroethylene and trichlorethylene, and is often abbreviated as TRI. It is a volatile chlorinated organic hydrocarbon widely used for metal degreasing and as a hydrofluorocarbon (HFC-134a) intermediate (ATSDR, 2013). It is also used in adhesives, paint stripping formulations, paints, varnishes and varnishes. In the 1930s, TCE was introduced for dry cleaning, but the practice largely ceased in the 1950s, when TCE was replaced by tetrachlorethylene (PCE). It has had many other uses in the past in cosmetics, drugs, foods, and pesticides (U.S. Environmental Protection Agency, 2011). It is an environmental contaminant that has been detected in air, groundwater, surface water, and soil (U.S. EPA, 2011; NRC, 2006). |
| chemical properties | Trichlorethylene, a colorless (usually tinted blue), nonflammable, noncorrosive liquid with the "sweet" odor characteristic of certain chlorinated hydrocarbons. Odor threshold is 25-50 ppm. |
| physical properties | Clear, colorless, watery liquid with a chloroform-like odor. Odor threshold concentrations determined in air are 21.4 ppm v (Leonardos et al., 1969) and 3.9 ppm v (Nagata and Takeuchi, 1990). The average minimum detectable odor threshold concentrations in 60°C water and 40°C air were 10 and 2.6 mg/L, respectively (Alexander et al., 1982). |
| use | Trichlorethylene is used as a solvent, dry cleaning, degreasing, and in limited use as a surgical anesthetic. |
| use | A chlorinated hydrocarbon used as a cleaner or solvent for metals, oils, resins, sulfur, and as a degreaser for gemstones. It can cause irritant contact dermatitis, generalized rash, Stevens-Johnson syndrome, pustular or bullous rash, and scleroderma. |
| use | Solvent for fats, waxes, resins, oils, rubber, paints and varnishes. Solvent for cellulose esters and ethers. Used for solvent extraction in many industries. In degreasing, dry cleaning. Used in the manufacture of organic chemicals, pharmaceuticals, chloroacetic acid, etc. |
| definition | ChEBI: A member of the vinyl chloride class in which ethylene is substituted with chlorine groups at positions 1, 1, and 2. |
| production method | TCE has been in commercial use for nearly 60 years. TCE is used as a solvent due to its powerful ability to dissolve fats, greases and waxes. It has been widely used in the dry cleaning industry, as a metal degreaser, as well as in the electronic components industry, where workers have been observed using it as a cleaning solvent without any protective equipment, resulting in uncontrolled skin contact and inhalation exposure. |
| general instructions | A clear, colorless, volatile liquid with a chloroform-like odor. Denser than water, slightly soluble in water. Nonflammable. Used as solvents, fumigants, in the manufacture of other chemicals, and many other uses. |
| air and water reaction | Slightly soluble in water. |
| reactive profile | Trichlorethylene has been experimentally determined to be explosive. A mixture of finely divided barium metal and a variety of halogenated hydrocarbons has the ability to explode. Specifically, shock susceptibility tests have shown that granular barium is explosive when in contact with fluorotrichloromethane, trichlorotrifluoroethane, carbon tetrachloride, trichloroethylene, or tetrachloroethylene (ASESB Pot. Incid. 39. 1968 ; Chem. Eng. News 46(9):38. 1968). Trichlorethylene It has been experimentally determined that beryllium powder mixed with carbon tetrachloride or with trichlorethylene flashes or sparks when struck violently (ASESB Pot. Incid. 39. 1968). Mixtures of magnesium powder with trichlorethylene or carbon tetrachloride can flash or spark under severe impact (ASESB Pot. Incid, 1968-39). |
| health hazard | Toxic effects exhibited by humans after inhalation of trichlorethylene vapor include headache, dizziness, drowsiness, fatigue, and visual impairment. Exposure to 1000 ppm for 2 hours affects visual perception. Higher concentrations can produce anesthetic effects. Massive exposure may result in death from respiratory failure or cardiac arrest. Rats exposed to concentrations of 8,000 ppm can be fatal within 4 hours. Long-term exposure resulted in increased kidney and liver weight in test animals. Symptoms of oral trichlorethylene poisoning are nausea, vomiting, diarrhea, and stomach upset. However, acute oral toxicity is low. Theoretical LD50 values for mice are in the range of 2500 mg/kg. Trichlorethylene is metabolized into trichloroacetic acid, which is excreted in the urine. Although trichlorethylene is less toxic, its metabolite trichloroethanol and its oxidative degradation products phosgene, COCl2 and chlorine pose serious unintended health hazards. Kawakami and Associates (1988) reported a case of Steven-Johnson syndrome in a printing plant worker. In another case, a stove in a metal degreasing workplace caught fire, producing phosphorus genes and inhaling chlorine gas, causing difficulty in breathing, fever, and fatigue. Trichlorethylene has been shown to be carcinogenic in experimental animals. Oral administration produces liver tumors, while inhalation causes lung and blood tumors in mice and rats. |
| fire hazard | Special hazards from combustion products: Toxic and irritating gases can be produced in the event of fire. |
| Flammability and explosiveness | non-flammable |
| chemical reactivity | Reactivity with water: Not relevant; Reactivity with common materials: Not relevant; Stability during transport: Stable; Neutralizer for acids and caustics: Not relevant; Polymerization: Not relevant; Polymerization inhibitors: Not relevant. |
| Industrial applications | Trichlorethylene is widely used as a metal degreasing agent in industry. It is especially valuable for its cleaning properties, low flammability and lack of a measurable flash point. Trichlorethylene is also used as a chemical process intermediate in the production of fluorides and polyvinyl chloride (PVC). It has been used worldwide for over 70 years. It is a colorless, volatile liquid and an unsaturated aliphatic halogenated hydrocarbon. In the United States, it is produced by Dow Chemical Company and PPG Industries. In 1998, U.S. demand was about 171 million pounds (77,700 metric tons), of which about 15 million pounds (6,800 metric tons) were imported. Exports were approximately 84 million pounds (38,000 metric tons). Trichlorethylene usage in 1999 can be broken down into the following categories: Chemical intermediates (~54%) Metal cleaning and degreasing (-42%) Others (~4%) High-purity trichlorethylene Used as a synthetic refrigerant Hydrofluoride Raw material for hydrocarbon 134a. In the process, the trichlorethylene molecules are destroyed, forming new fluorinated compounds. The advantages of trichlorethylene in metal cleaning include the ability to degrease more thoroughly and several times faster than alkaline cleaners, and compatibility with smaller appliances that consume less energy. Trichlorethylene is an important solvent for cleaning steel sheets and strips before aluminum degreasing and galvanizing. Trichlorethylene is also used to clean liquid oxygen and liquid hydrogen tanks. Commercial trichlorethylene formulations contain a stabilizer system to help prevent solvolysis caused by contaminants such as acids, metal fragments and fines, and exposure to oxygen, light and heat. Trichlorethylene is also used as a solvent in some nonflammable adhesives and aerosol formulations, and as a low-temperature heat transfer medium. Other applications of trichlorethylene include use as a solvent in the metal processing, electronics, printing, pulp and paper, and textile industries. |
| Contact allergens | Trichlorethylene is a chlorinated hydrocarbon used as a detergent or solvent for metals, oils, resins, sulfur, and as a general degreasing agent. It can cause irritant contact dermatitis, generalized rash, Stevens-Johnson-like syndrome, pustular or bullous rash, scleroderma, and neurologic and hepatic disorders. |
| Security overview | Carcinogens with confirmed experimental carcinogenicity, tumorigenicity and teratogenicity data. Experimental poisoning was performed by intravenous and subcutaneous routes. Experimentally proven to be moderately toxic by the ingestion and intraperitoneal routes. Slightly toxic to humans by ingestion and inhalation. Experimental inhalation has mild toxicity. Systemic Effects of Ingestion and Inhalation: Eye effects, drowsiness, hallucinations or distorted perceptions, gastrointestinal changes, and jaundice. Experimental reproductive effects. Human mutation data are reported. Severely irritating to eyes and skin. Inhalation of high concentrations can cause anesthesia and anesthesia. Some form of addiction has been observed among workers exposed to the substance. Prolonged inhalation of moderate concentrations can cause headaches and drowsiness. Severe death may occur, and acute exposure can cause ventricular fibrillation, leading to heart failure. Long-term exposure can cause damage to the liver and other organs. A common air pollutant. It is not flammable, but high-concentration trichlorethylene vapor can burn slightly when exposed to strong flames in high-temperature air. Although this situation is difficult to produce, flames or arcs should not be used in enclosed equipment containing any solvent residues or vapors. Reacts with bases and epoxides, such as 1-chloro-2,3-epoxypropane, 1,4-butanediol mono-2,3-epoxypropyl ether, 1,4-butanediol di-2 ,3-epoxypropyl ether and 2,2-bis[(4(2',3'-epoxypropoxy)phenyl)propane] form the self-igniting flammable gas dichloroacetylene. Can react violently with Al, Ba, N2O4, Li, Mg, liquid O2, O3, KOH, KNO3, Na, NaOH, and Ti. Reacts with water under heat and pressure to form HCl gas. Heating decomposition releases toxic Cl-fumes. See also aliphatic chlorinated hydrocarbons. |
| potential contact | Trichlorethylene is used as a vapor degreaser for metal parts, as a solvent; and as a drug; it is also used to extract caffeine from coffee, as a dry cleaning agent; and as a chemical intermediate in the production of pesticides; in the manufacture of waxes, gums, resins, Tars, paints, varnishes and certain chemicals; such as chloroacetic acid. |
| Carcinogenicity | Based on limited evidence of carcinogenicity from human studies, sufficient evidence of carcinogenicity from studies in experimental animals, and information from studies of carcinogenic mechanisms, trichlorethylene is reasonably expected to be a human carcinogen. |
| source | Known perchlorethylene degradation product. |
| environmental fate | biology. Microbial degradation of trichlorethylene by sequential dehalogenation produces cis- and trans-1,2-dichloroethylene and vinyl chloride (Smith and Dragun, 1984). Anoxic microcosms in sediment and water degrade trichlorethylene to 1,2-dichloroethylene and then to vinyl chloride (Barrio-Lage et al., 1986). Trichlorethylene was anaerobically degraded to 1,2-dichloroethylene in soil samples collected from Des Moines, Iowa. No 1,1-dichloroethylene production was observed in this study (Kleopfer et al., 1985). surface water. The estimated half-life of trichlorethylene (3.2 μg/L) in experimental marine ecosystems during spring (8–16 °C), summer (20–22 °C) and winter (3–7 °C) is 28, 13 , and 15 d, respectively (Wakeham et al., 1983). In laboratory experiments, the volatilization half-life of trichlorethylene was about 1.25 h in a stirred water container (outer dimensions 22 x 10 x 21 cm) at 23 °C and an air velocity of 0.20 m/sec. (Kläpffer et al., 1982). Photolytic. Under smog conditions, phosgene, dichloroacetyl chloride, and formyl chloride are produced by indirect photolysis of OH radicals (Howard, 1990). These compounds are readily hydrolyzed to HCl, carbon monoxide, carbon dioxide, and dichloroacetic acid (Morrison and Boyd, 1971). Dichloroacetic acid and hydrogen chloride have been reported as aqueous photolysis products (Dilling et al., 1975). Reported rate constants for the reaction of trichlorethylene with OH radicals in the atmosphere: 1.2 x 10 -12 cm 3 /mol?s at 300 K (Hendry and Kenley, 1979), 2 x 10 -12 cm 3 /molecule?s (Howard, 1976), 2.36 x 10 -12 cm 3 /mol?s at 298 K (Atkinson, 1985) ), 2.86 x 10 -12 cm 3 /mol?s at 296 K (Edney et al., 1986 ); NO3: 2.96 x 10 -16 cm 3 /molecule? sec, 296 K (Atkinson et al., 1988). Chemistry/Physics. Trichlorethylene (1 mg/L) has an evaporation half-life of 18.5 minutes in water at an average depth of 6.5 cm using a shallow-pitch propeller stirrer at 200 rpm at 25 °C (Dilling, 1977). |
| metabolic pathway | From the photooxidative reaction medium (1) of trichlorethylene, the formation of dichloroacetyl chloride, CO, phosgene and pentachloroethane and their conversion to the final product CO2 was determined. Through the second TiO2 photocatalyst reaction (2), trichloroacetaldehyde, dichloroacetyl chloride, CO, and phosgene were observed along with the newly identified intermediates oxalyl chloride, trichloroacetyl chloride, and trichloroacetic acid. |
| Shipping | UN1710 Trichlorethylene, hazard level: 6.1; label: 6.1-toxic substance. |
| Purification method | 三氯乙烯的分解方式与 CHCl3 类似，产生 HCl、CO、COCl2 和有机产物。与KOH、NaOH和90% H2SO4反应，与水、MeOH、EtOH和乙酸形成共沸物。依次用2M HCl、水和2M K2CO3 洗涤纯化，然后用K2CO3 和CaCl2 干燥，然后在使用前分馏。它还从 10% Ca(OH)2 浆料中进行蒸汽蒸馏，通过冷却至 -30o 至 -50o 并通过麂皮过滤掉冰，从馏出物中除去大部分水：然后在 250mm 下分馏三氯乙烯压力并收集在黑色容器中。[Carlisle & Levine Ind Eng Chem（肛门编辑）24 1164 1932，Beilstein 1 IV 712。] |
| 毒性评价 | 长时间接触（例如职业接触）氯化溶剂（如 TCE）通常会导致中枢神经系统 (CNS) 紊乱和肝毒性的迹象。动物研究中发现，三氯乙烯致癌的主要靶组织是肝、肺和肾。对于这些目标组织中的每一个，有证据表明 TCE 的致癌性可能与其一种或多种代谢物有关：肝脏中的 TCA 和二氯乙酸 (DCA)、肺中的三氯乙醛和 S-(1,2-二氯乙烯基) )-L-半胱氨酸 (DCVC) 在肾脏中。 TCA 充当过氧化物酶体增殖剂，小鼠肝脏肿瘤可能通过这种机制产生。TCE 通过细胞色素 P450 代谢产生代谢物 DCA 和 TCA，它们与肝毒性和肝癌有关。DCA和TCA可能通过（1）改变信号通路诱导肝脏肿瘤发生；(2)细胞毒性、细胞死亡和修复性增生；(3)直接DNA损伤。 TCE 通过谷胱甘肽 (GSH) 结合代谢产生 DCVC，它与肾毒性和肾癌有关。DCVC 可以被不同的酶生物激活和解毒。主要负责肾毒性半胱氨酸 S-缀合物的肾脏生物活化的酶是 b-裂解酶。DCVC 的 b-裂合酶催化代谢产生的反应性硫醇和后续物质可能通过以下方式诱导肾肿瘤发生：(1) 过氧化物酶体增殖，(2) α-2 球蛋白肾病，(3) 导致体细胞突变的遗传毒性，以及 (4) 急性细胞毒性和坏死导致细胞增殖。 |
| 不兼容性 | 接触强碱会引起分解并产生剧毒且易燃的二氯乙炔。与化学活性金属发生剧烈反应；粉末或刨花，例如铝、钡、锂、钠、镁和钛。在稀盐酸存在下与铝发生剧烈反应。三氯乙烯因接触热金属或紫外线辐射而热分解，形成氯气、氯化氢等危险产物；和光气。使该化学品远离高温，如电弧焊或切割、无屏蔽电阻加热；明火；和高强度紫外线。在有湿气的情况下受光缓慢分解，并形成盐酸。 |
| 废物处理 | 请咨询环境监管机构，获取有关可接受处置实践的指导。含有该污染物（≥100 kg/mo）的废物产生者必须符合 EPA 关于储存、运输、处理和废物处置的规定。焚烧，最好与另一种可燃燃料混合后焚烧。必须小心确保完全燃烧，以防止形成光气。需要使用酸洗涤器来去除产生的卤酸。TCE 处置的替代方法是回收和再循环。 |
| 三氯乙烯 上下游产品信息 |
| 原料 | 氯-->四氯化碳-->三氯化铁-- >电石-- >油漆稀释剂-->四氯乙烯--> 1,1,2,2-四氯乙烷--> 1,1,2,2-四氯乙烷- D2 -->五氯乙烷 |
| 制剂产品 | 氯乙酸-->清洗剂-->六甲基磷酰胺-->乐果-->杀虫磷-->四氯乙烯-->敌敌畏-->六氯乙烷-->亚乙基硫脲--> 2-苯基苯酚-->二氯乙酰氯-->辣椒红素-->喷托维林-->比硫醇-->叶绿素 A --> 4-苯基苯酚--> 4-氨基-6-甲氧基嘧啶--> 3-氨基-4,5,6,7-四氢苯并[B ]噻吩-2-羧酸甲酯-->四氯环丙烯-->叶绿酸铜复合钠盐-->双(2,3,3,3-四氯丙基)醚-->五氯乙烷-->二丙哌啶--> 1,1,1-三氯三氟乙烷-->钠2-联苯酯--> Simazine --> 4-isopropyl-3-methylphenol --> Sulfamethoxine --> 2,4,6-trifluorophenyl isothiocyanate --> Sulfonamide Trimethoprim sodium salt |
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