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1,1-DICHLOROETHANE

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1,1-DICHLOROETHANE Basic information
1,1-DICHLOROETHANE Chemical Properties
  • Melting point:235℃
  • Boiling point:57°C
  • Density 1,18 g/cm3
  • vapor pressure 227 at 25 °C (quoted, Howard, 1990)
  • refractive index 1.42213 (20℃)
  • Flash point:-6°C
  • storage temp. Refrigerator
  • solubility Miscible with ethanol (U.S. EPA, 1985)
  • form neat
  • Relative polarity0.269
  • Water Solubility 5.057g/L(25 ºC)
  • Merck 3810
  • BRN 1696901
  • Henry's Law Constant4.84 at 25 °C (batch air stripping-GC, Bobadilla et al., 2003)
  • Exposure limitsNIOSH REL: TWA 100 ppm (400 mg/m3), IDLH 3,000 ppm; OSHA PEL: TWA 100 ppm; ACGIH TLV: TWA 100 ppm (adopted).
  • Stability:Stable. Highly flammable. Vapour/gas mixtures explosive. Incompatible with plastics, many organic materials. Reacts with metals, oxidizing agents.
  • CAS DataBase Reference75-34-3(CAS DataBase Reference)
  • EPA Substance Registry System1,1-Dichloroethane (75-34-3)
Safety Information
1,1-DICHLOROETHANE Usage And Synthesis
  • UsesCleansing agent; degreaser; solvent for plastics, oils, and fats; grain fumigant; chemical intermediate; formerly used as an anesthetic
  • DescriptionChlorinated aliphatics as a class are known to cause central nervous system (CNS) depression and respiratory tract and dermal irritation when humans are exposed by inhalation to sufficiently high concentrations. In the past, 1,1-dichloroethane was used as an anesthetic; however, this use was discontinued due to the risk of induction of cardiac arrhythmia in humans. Crystal precipitations and obstruction in the renal tubule lumina and increases in serum urea and creatinine were observed in cats exposed to this compound for weeks. However, these effects were not observed in rats, guinea pigs, or rabbits. However, kidney effectswere observed inmice administered a lethal intraperitoneal injection; the effects included increased glucose and protein in the urine and tubular swelling. The toxicological significance of the nephrotoxicity observed in cats and the mice with regard to human health is not known given the small number of animals tested (cats).The detectionof 1,1-dichoroethane or itsmetabolites in blood and urine cannot predict the type of health effects that might develop from that exposure; because 1,1-dichloroethane and its metabolites leave the body fairly rapidly, the tests need to be conducted within hours to days after exposure.
  • Chemical PropertiesAlso ethylidene chloride,CH3CHCl2 is a colorless,neutral,mobile liquid with an aromatic ethereal odor and saccharin taste. Soluble in alcohol, ether,fixed and volatile oils and very sparingly soluble in water. It is used as an extraction solvent and fumigant.
  • Chemical Properties1,1-Didichloroethane is a colorless, oily liquid with a chloroform-like odor.
  • Physical propertiesClear, colorless, oily liquid with a chloroform-like odor
  • UsesEthylidene dichloride is primarily used as an intermediate in chemical synthesis. Acute (short-term) inhalation exposure to high levels of ethylidene dichloride in humans results in central nervous system (CNS) depression and a cardiostimulating effect resulting in cardiac arrhythmias. Studies in animals have reported effects on the kidney. No information is available on the chronic (long-term) reproductive, developmental, or carcinogenic effects of ethylidene dichloride in humans. An oral animal study reported a significantly positive dose-related trend in hemangiosarcomas, mammary tumors, liver tumors, and endometrial stromal polyps. EPA has classified ethylidene dichloride as a Group C, possible human carcinogen.
    Primary uses are:
    Ethylidene dichloride is primarily used as an intermediate in the manufacture of other chemicals such as vinyl chloride and 1,1,1- trichloroethane, and to manufacture high vacuum rubber.
    Ethylidene dichloride has limited use as a solvent for plastics, oils, and fats.
    In the past, ethylidene dichloride was used as an anesthetic, but that use has been discontinued.
    Ethylidene dichloride is a colorless oily liquid which is very volatile. It has an odor similar to ether; the odor threshold is 120 parts per million (ppm).
  • Uses1,1-Dichloroethane is used as a chemical solvent in the preparation of precursors of quinolizine, isoquinoline and indole alkaloids.
  • UsesSolvent for paint, varnishes; degreaser. Has been used as a surgical anesthetic.
  • General DescriptionA 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.
  • Air & Water ReactionsHighly flammable. Slightly soluble in water.
  • Reactivity Profile1,1-DICHLOROETHANE can react vigorously with oxidizing materials. 1,1-DICHLOROETHANE is incompatible with strong bases. Contact with strong caustics will cause formation of flammable and toxic gas. 1,1-DICHLOROETHANE will attack some forms of plastics, rubber and coatings.
  • HazardToxic. Eye and upper respiratory tract irritant; kidney and liver damage. Questionable carcinogen.
  • Health HazardINHALATION: Irritation of respiratory tract. Salivation, sneezing, coughing, dizziness, nausea, and vomiting. EYES: Irritation, lacrimation, and reddening of conjunctiva. SKIN: Irritation. Prolonged or repeated skin contact can produce a slight burn. INGESTION: Ingestion incidental to industrial handling is not considered to be a problem. Swallowing of substantial amounts could cause nausea, vomiting, faintness, drowsiness, cyanosis, and circulatory failure.
  • Safety ProfileModerately toxic by ingestion. Experimental teratogenic effects. Questionable carcinogen with experimental tumorigenic data. Liver damage reported in experimental animals. A very dangerous fire hazard and moderate explosion hazard when exposed to heat or flame; can react vigorously with oxidizing materials. To fight fire, use alcohol foam, water, foam, CO2, dry chemical. When heated to decomposition it emits highly toxic fumes of phosgene and Cl-
  • Potential ExposureIt is used as a solvent; cleaning and degreasing agent; as well as in organic synthesis as an intermediate
  • CarcinogenicityThe EPA 2010 classifies 1,1- dichloroethane in group C, a possible human carcinogen, 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. The EPA offers no estimate of carcinogenic risk from inhalation or oral exposure. The EPA states (IRIS) that because of similarities in structure and target organs, the carcinogenic evidence for 1,2-dichloroethane is supportive of the classification of 1,1-dichloroethane in group C, a possible human carcinogen. The EPA considers the animal carcinogenicity “limited.”
    The NCI bioassay), provides limited evidence for the carcinogenicity of 1,1-dichloroethane in Osborne–Mendel rats and B6C3F1 mice. This is based on significant doserelated increases in the incidence of hemangiosarcomas at various sites and mammary carcinomas in female rats and statistically significant increases in the incidence of liver carcinomas in male mice and benign uterine polyps in female mice. The study is limited by high mortality in many groups. The low survival rates precluded the appearance of possible late-developing tumors and decreased the statistical power of this bioassay. Technical-grade 1,1-dichloroethane in corn oil was administered by gavage 5 days/week for 78 weeks to groups of 50 Osborne–Mendel rats/sex/dose. All surviving animals were necropsied following a 33 week observation period. Due to toxicity, dosing was not continuous (3 week on, then 1 week off), making the TWAs for 5 days/week 382 and 764 mg/kg/day for low- and high-dose males and 475 and 950 mg/kg/day for low- and high-dose females, respectively. Both a vehicle and an untreated (not intubated) control group (20 rats/sex/group) were included in the study. A high incidence of pneumonia (approximately 80%) in all four groups of each sex was considered to be the cause for the lowsurvival at termination of the study.
  • Environmental FateBiological. 1,1-Dichloroethane showed significant degradation with gradual adaptation in a static-culture flask-screening test (settled domestic wastewater inoculum) conducted at 25 °C. At concentrations of 5 and 10 mg/L, percent losses after 4 wk of incubation were 91 and 83, respectively. At a substrate concentration of 5 mg/L, 19% was lost due to volatilization after 10 d (Tabak et al., 1981). Under anoxic conditions, indigenous microbes in uncontaminated sediments produced vinyl chloride (Barrio-Lage et al., 1986).
    Surface Water. The following volatilization half-lives were reported for 1,1-dichloroethane: 6 to 9 d in a pond, 5 to 8 d in a lake, 24 to 32 h in a river (Smith et al., 1980).
    Photolytic. Titanium dioxide suspended in an aqueous solution and irradiated with UV light (λ = 365 nm) converted 1,1-dichloroethane to carbon dioxide at a significant rate (Matthews, 1986). The initial photodissociation product of 1,1-dichloroethane was reported to be chloroacetyl chloride (U.S. EPA, 1975). This compound is readily hydrolyzed to HCl and chloroacetic acid (Morrison and Boyd, 1971).
    The rate constant for the reaction of 1,1-dichloroethane and OH radicals in the atmosphere at 300 K is 1.6 x 10-11 cm3/molecule?sec (Hendry and Kenley, 1979). At 296 K, a photooxidation rate constant of 2.6 x 10-13 cm3/molecule?sec was reported for the reaction with OH radicals resulting in a half-life of 1.5 months (Howard and Evenson, 1976).
    Chemical/Physical. A glass bulb containing air and 1,1-dichloroethane degraded outdoors to carbon dioxide and HCl. The half-life for this reaction was 17 wk (Pearson and McConnell, 1975). Hydrolysis of 1,1-dichloroethane under alkaline conditions yielded vinyl chloride, acetaldehyde, and HCl (Kollig, 1993). The reported hydrolysis half-life at 25 °C and pH 7 is 61.3 yr (Jeffers et al., 1989).
  • ShippingUN2362 1,1-Dichloroethane, Hazard Class: 3; Labels: 3-Flammable liquid
  • Purification MethodsShake it with conc H2SO4 or aqueous KMnO4, then wash it with water, saturated aqueous NaHCO3, again with water, dry with K2CO3 and distil it from CaH2 or CaSO4. Store it over silica gel. [Beilstein 1 IV 130.]
  • Toxicity evaluationProduction and use of 1,1-dichloroethane as a chemical intermediate, in paint removers, and as a antiknock gasoline additive may result in its release to the environment through various waste streams. If released to air, it will exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,1-dichloroethane will be degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals (estimated half-life, 49 days). 1,1-Dichloroethane when released to soil is expected to have very high mobility based on a Koc of 30. Volatilization from moist soil surfaces is expected to be an important fate process of this compound. 1,1-Dichloroethane may volatilize from dry soil surfaces based on its vapor pressure. Halogenated aliphatic hydrocarbons are generally considered to be resistant to biodegradation. However, in water, 1,1-dichloroethane is not expected to adsorb to suspended solids and sediments based on the Koc. Estimated volatilization half-lives for a model river and model lake are 3 h and 4 days, respectively. An estimated bioconcentration factor of 5 suggests the potential for bioconcentration in aquatic organisms is low. The environmental hydrolysis half-life at 25°C and pH 7 is 61 years.
  • IncompatibilitiesVapor may form explosive mixture with air. Reacts violently with strong oxidizers, alkali metals; earth-alkali metals; powdered metals; causing fire and explosion hazard. Contact with strong caustic will produce flammable and toxic acetaldehyde gas. Attacks aluminum, iron. Attacks some plastics (including polyethylene) and coatings.
  • Waste DisposalIncineration; preferably after mixing with another combustible fuel. Care must be exercised to assure complete combustion to prevent the formation of phosgene. An acid scrubber is necessary to remove the halo acids produced. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal
1,1-DICHLOROETHANE Preparation Products And Raw materials
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