|
| | 2,2'-Dichlorodiethyl ether Basic information |
| | 2,2'-Dichlorodiethyl ether Chemical Properties |
| Melting point | −47 °C(lit.) | | Boiling point | 65-67 °C15 mm Hg(lit.) | | density | 1.22 g/mL at 25 °C(lit.) | | vapor pressure | 0.4 mm Hg ( 20 °C) | | refractive index | n20/D 1.456(lit.) | | Fp | 131 °F | | storage temp. | Store at <= 20°C. | | solubility | 0.01g/l | | form | Colorless liquid | | color | Colorless to Almost colorless | | Odor | Sweet, like chloroform. | | explosive limit | 0.8%(V) | | Water Solubility | Slightly soluble. 1.72 g/100 mL | | Merck | 14,3066 | | BRN | 605317 | | Henry's Law Constant | (x 10-5 atm?m3/mol):
124.7, 15.8, 72.0, 12.5, and 1.38 at 10, 15, 20, 25, and 30 °C, respectively (EPICS, Howe et al.,
1987) | | Exposure limits | NIOSH REL: TWA 5 ppm (30 mg/m3), STEL 10 ppm, IDLH 100 ppm;
OSHA PEL: C 15 ppm (90 mg/m3); ACGIH TLV: TWA 30 mg/m3, STEL 60 mg/m3. | | Stability: | Stable. Combustible. Incompatible with strong oxidizing agents. | | InChIKey | ZNSMNVMLTJELDZ-UHFFFAOYSA-N | | LogP | 1.12-1.56 at 20℃ | | CAS DataBase Reference | 111-44-4(CAS DataBase Reference) | | IARC | 3 (Vol. 9, Sup 7, 71) 1999 | | NIST Chemistry Reference | Beta,beta'-dichloroethyl ether(111-44-4) | | EPA Substance Registry System | Bis(2-chloroethyl) ether (111-44-4) |
| | 2,2'-Dichlorodiethyl ether Usage And Synthesis |
| Chemical Properties | Dichloroethyl ether is a clear, colorless
liquid. Pungent, fruity odor. It is also described as having
a chlorinated solvent-like odor. | | Chemical Properties | colourless liquid | | Physical properties | Colorless to pale yellow volatile liquid with a pungent, fruity, chlorinated-like odor. The low odor
and high odor threshold concentrations were 90.0 and 2,160 mg/m3, respectively (Ruth, 1986). | | Uses | Bis(2-chloroethyl)ether (BCEE) is used as ascouring agent for textiles; as a dewaxingagent for lubricating oils; as a soil fumigant;as a solvent for resins, oils, and lacquers; andin organic synthesis. | | Uses | Soil fumigant; acaricide. | | Uses | Reagent for organic synthesis; solvent. Has been used as a scouring agent for textiles; as soil fumigant. | | Definition | ChEBI: Bis(2-chloroethyl)ether is an ether. | | General Description | A clear colorless liquid with a sweet pleasant or nauseating odor. Flash point 131°F. Denser than water and insoluble in water. Toxic by inhalation and skin absorption. Used in cleaning compounds, paints, textile finishing, and as a general solvent. | | Air & Water Reactions | Flammable. Insoluble in water. Reacts slowly with water to form HCl. Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154]. | | Reactivity Profile | 2,2'-Dichlorodiethyl ether may form phosgene or hydrogen when heated to high temperature. Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154]. Mixing in equal molar portions with the following substances in a closed container caused the temperature and pressure to increase: chlorosulfonic acid and oleum [NFPA 1991]. | | Health Hazard | 2,2'-Dichlorodiethyl ether is very toxic; the probable oral lethal dose is 50-500 mg/kg, or between 1 teaspoonful and 1 ounce for a 150 pound person. It can be a central nervous system depressant in high concentrations. It is extremely irritating to the eyes, nose, and respiratory passages. It can penetrate the skin to cause serious and even fatal poisoning. Poisonous; may be fatal if inhaled, swallowed or absorbed through skin. | | Health Hazard | BCEE is an acute toxic compound withcancer-causing properties. The toxic routesare inhalation, ingestion, and absorptionthrough the skin. Exposure to its vaporscaused irritation of the eyes, nose, and res piratory tracts in test animals. Exposure to aconcentration of 250 ppm in air for 4 hoursproved lethal to rats (ACGIH 1986). At alower concentration, it caused delayed deathfollowing damage to lungs. Other organsaffected to a lesser degree were the liver,kidneys, and brain.
The irritant action of BCEE on the eyesvaried from mild to severe. In humans,contact of pure liquid can cause conjunctivalirritation and injury to the cornea. On theskin, its irritation effect is mild. However,on prolonged contact, the liquid may beabsorbed through the skin and manifest toxiceffects
Ingestion of this compound in smallamounts may produce nausea and vomiting.An oral dose of 50–75 mL is expected to befatal to humans
LC50 value, inhalation (rats): 330 mg (56ppm)/m3/4 hr
LD50 value, oral (rats): 75 mg/kg
LD50 value, skin (guinea pigs): 300 mg/kg
LD50 value, skin (guinea pigs): 300 mg/kg. | | Fire Hazard | May form phosgene or hydrogen chloride in fires. There is danger of explosion when ethers are heated or exposed to flames or sparks. Ethers tend to form peroxides; when ethers containing peroxides are heated, they can detonate. May be ignited by heat, sparks, or flames. Container may explode in heat of fire. Vapor explosion and poison hazard indoors, outdoors or in sewers. Decomposes in the presence of moisture to form hydrochloric acid. Emits toxic fumes when heated to decomposition. Reacts vigorously with oleum and chlorosulfonic acid. Ethers tend to form peroxides upon standing. Heating peroxide-containing ethers can cause detonation. | | Flammability and Explosibility | Notclassified | | Chemical Reactivity | Reactivity with Water : No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: V; Inhibitor of Polymerization: Not pertinent. | | Safety Profile | A poison by ingestion,
skin contact, and inhalation. A skin, eye, and
mucous membrane irritant. Questionable
carcinogen with experimental carcinogenic
and tumorigenic data. Mutation data
reported. Exposure to 1000 ppm for 30 to
60 minutes may result in death within days.
The odor is easily detectable at 35 ppm
whch causes only slight irritation.
Flammable liquid when exposed to heat,
flame, or oxidants. Dangerous explosion
hazard; reacts vigorously with oleum,
chlorosulfonic acid. Reacts with water or
steam to evolve toxic and corrosive fumes.
Can react vigorously with oxidizing
materials. To fight fire, use water, foam,
mist, fog, spray, dry chemical. When heated
to decomposition it emits toxic fumes of
Cl-. See also ETHERS. | | Potential Exposure | Dichloroethyl ether is used as a soil
fumigant, an insecticide, and an acaricide; in the manufacture of paint, varnish, lacquer, soap, and finish removers. It
is also used as a solvent for cellulose esters, naphthalenes,
oils, fats, waxes, greases, pectin, tar, and gum; in dry cleaning and in textile scouring. | | Source | Bis(2-chloroethyl) ether does not occur naturally in the environment. In Canada, this
compound enters the environment as a by-product from chlorination of waste streams containing
ethylene, propylene (Environment Canada, 1993) or ethyl ether (quoted, Verschueren, 1983). | | Environmental Fate | Biological. When 5 and 10 mg/L of bis(2-chloroethyl)ether were statically incubated
in the dark at 25°C with yeast extract and settled domestic wastewater inoculum, complete
degradation was observed after 7 days (Tabak et al., 1981).
Chemical/Physical. Bis(2-chloroethyl)ether is subject to hydrolysis (Enfield and Yates,
1990; NIOSH, 1994). The hydrolysis rate constant for bis(2-chloroethyl)ether at pH 7 and
25°C was determined to be 2.6 × 10–5/hour, resulting in a half-life o
Emits chlorinated acids when incinerated (Sittig, 1985). | | Shipping | UN1916 2,20
-Dichlorodiethyl ether, Hazard
class: 6.1; Labels: 6.1-Poisonous materials, 3-Flammable
liquid | | Purification Methods | Wash the ether with conc H2SO4, then Na2CO3 solution, dry with anhydrous Na2CO3, and finally pass it through a 50cm column of activated alumina before distillation. Altern | | Incompatibilities | Contact with moisture caused decomposition producing hydrochloric acid. Can form peroxides.
May form explosive mixture with air. Contact with strong
oxidizers may cause fire and explosion hazard. Attacks
some plastics, rubber, and coatings. Attacks metals in the
presence of moisture | | Waste Disposal | A potential candidate for
liquid injection incineration at a temperature range of 650
to 1600C and a residence time 0.1 to 2 seconds. Also,
a potential candidate for rotary kiln incineration at
a temperature range of 820 to 1600C and residence times
of seconds for liquids and gases, and hours for solids. Also,
a potential candidate for fluidized bed incineration at a
temperature range of 450 to 980C and residence times of
seconds for liquids and gases, and longer for solids.
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 |
| | 2,2'-Dichlorodiethyl ether Preparation Products And Raw materials |
|
