Dichloroethyne Chemical Properties
- Melting point:-126°C
- Density 1.2610
- refractive index 1.4279
- form Liquid
- IARC3 (Vol. 39, Sup 7, 71) 1999
- EPA Substance Registry SystemDichloroacetylene (7572-29-4)
Dichloroethyne Usage And Synthesis
- Chemical PropertiesDCA is a volatile, pyrophoric oil. It has an unpleasant, sweetish odor. A gas above 32°C/90°F.
- UsesDCA is not commercially available in large quantities. It is reportedly a by-product of the synthesis of vinylidene chloride and is not known to be used commercially.
- UsesBy-product in synthesis of vinylidene chloride; decomposition product of trichloroethylene under alkaline conditions
- Production MethodsDCA is a highly toxic, spontaneously combustible, undesired, and noncommercial product of the dehydrochlorination of trichloroethylene. It has resulted from exposure of trichloroethylene vapor to Hopcalite in a closed environmental system (submarine) and soda lime in closed circuit (rebreathing) anesthesia machines and from exposure of trichloroethylene liquid to caustic in degreaser tanks. It may also be an undesired by-product during chemical processes such as production of vinylidene chloride. When DCA was decomposed in the presence of oxygen, seven substanceswere found: phosgene, hexachlorobutadiene, chloroform, carbon tetrachloride, trichloroacetyl chloride, tetrachloroethylene, and trichloroacryloyl chloride.
- Synthesis Reference(s)The Journal of Organic Chemistry, 52, p. 3461, 1987 DOI: 10.1021/jo00391a059
- General DescriptionVolatile oil with a disagreeable, sweetish odor. Mp: -68 to -65°C; bp: 32-34°C. Density: 1.38 g cm-3. Is not produced commercially.
- Air & Water ReactionsIgnites or explodes upon contact with air (MCA Case History 1989 (1974)).
- Reactivity ProfileDichloroethyne is a reducing agent. Incompatible with oxidizing agents. Can ignite or explode on contact with air or if heated. Can explode if shocked. Burns in the presence of chlorine to form phosgene (Ann. Chem. 640:5(1961)).
- Health HazardDichloroacetylene is a neurotoxin; it is carcinogenic in experimental animals.
- Safety ProfileConfirmed carcinogen with experimental carcinogenic data. Poison by inhalation. Central nervous system effects. Can be formed by thermal decomposition (>70摄氏度) from trichloroethylene. Symptoms include a disabling nausea and intense jaw pain. Strong explosive when shocked or exposed to heat or air. Can react vigorously with oxidizing materials. When heated to decomposition or on contact with acid or acid fumes it emits highly toxic fumes of Cl-. See also ACETYLENE COMPOUNDS and CHLORINATED HYDROCARBONS , ALIPHATIC.
- Potential ExposureDCA, dichloroacetylene, is not produced commercially and is a possible decomposition product of trichloroethylene or trichloroethane. Reported to be a by-product of vinylidene chloride (see V:0220). Also, a closed circuit anesthesia with trichloroethylene, heat and moisture produced by soda-lime absorption of CO2 may produce dichloroacetylene (DCA) along with phosgene and carbon monoxide (CO).
- CarcinogenicityThe IARC concluded that there is limited evidence for the carcinogenicity of DCA to experimental animals based on treatment-related increases in the incidence of adenocarcinomas of the kidney in male mice, benign tumors of the liver and kidney, and an increased incidence of lymphomas in rats.
- Metabolic pathwayBy the incubation of dichloroacetylene with rat liver and kidney subcellular fractions, the formation of S- (1,2-dichlorovinyl)glutathione (DCVG) is observed, and N-acetyl-S-(1,2-dichlorovinyl)-L-cysteine is identified as a urinary metabolite in rats.
- ShippingExplosive! Dichloroacetylene is cited by DOT as “FORBIDDEN.”
- IncompatibilitiesAn unstable explosive; heat or shock may cause explosion. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong acids (forms poisonous gases of phosgene and hydrogen chloride), strong bases.
- Sulfur hexafluoride lithium chloroacetylide dibromoacetylene chlorocyanoacetylene sodium chloroacetylide 5-DIMETHYLAMINO-2-METHYL-3-PENTYN-2-OL VINYL CHLORIDE 3-Bromopropyne fluoroethyne penicillinase 5,6-DICHLORO-2,3-DICYANOPYRAZINE N-PHENYL-1-NAPHTHYLAMINE HYDROBROMIDE, 98 diiodoacetylene acetylene bromide Dichloroethyne
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