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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℃) | | Fp | -6°C | | storage temp. | Refrigerator | | solubility | Miscible with ethanol (U.S. EPA, 1985) | | form | neat | | Relative polarity | 0.269 | | Water Solubility | 5.057g/L(25 ºC) | | Merck | 3810 | | BRN | 1696901 | | Henry's Law Constant | 4.84 at 25 °C (batch air stripping-GC, Bobadilla et al., 2003) | | Exposure limits | NIOSH 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 Reference | 75-34-3(CAS DataBase Reference) | | EPA Substance Registry System | 1,1-Dichloroethane (75-34-3) |
| | 1,1-Dichloroethane Usage And Synthesis |
| Description | Chlorinated 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 Properties | Also 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.
| | Physical properties | 1,1-Dichloroethane is a clear, colorless, oily liquid with a chloroform-like odor. It is more polar than trans but less polar than cis form.Two chlorine atoms are not on the same side of the plane,hence the net dipole is going to be lesser than cis form. | | Uses | Solvent for paint, varnishes; degreaser. Has been used as a surgical anesthetic. | | Uses | 1,1-Dichloroethane is used as a chemical solvent in the preparation of precursors of quinolizine, isoquinoline and indole alkaloids. | | Uses | Ethylidene 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). | | Definition | ChEBI: 1,1-Dichloroethane is an organochlorine compound. | | General Description | 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. | | Air & Water Reactions | Highly flammable. Slightly soluble in water. | | Reactivity Profile | 1,1-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. | | Hazard | Toxic. Eye and upper respiratory tract irritant; kidney and liver damage. Questionable carcinogen. | | Health Hazard | INHALATION: 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 Profile | Moderately 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 Exposure | It is used as a solvent; cleaning and
degreasing agent; as well as in organic synthesis as an
intermediate | | Carcinogenicity | The 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.” | | Environmental fate | Biological. 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). | | Shipping | UN2362 1,1-Dichloroethane, Hazard Class: 3;
Labels: 3-Flammable liquid | | Purification Methods | Shake 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 evaluation | Production 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. | | Incompatibilities | Vapor 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 Disposal | Incineration; 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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