111-44-4 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 111-44-4 differently. You can refer to the following data:
1. colourless liquid
2. Dichloroethyl ether is a clear, colorless
liquid. Pungent, fruity odor. It is also described as having
a chlorinated solvent-like odor.
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
Different sources of media describe the Uses of 111-44-4 differently. You can refer to the following data:
1. Reagent for organic synthesis; solvent. Has been used as a scouring agent for textiles; as soil fumigant.
2. Soil fumigant; acaricide.
3. 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.
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
Different sources of media describe the Health Hazard of 111-44-4 differently. You can refer to the following data:
1. 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.
2. 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 toxiceffectsIngestion of this compound in smallamounts may produce nausea and vomiting.An oral dose of 50–75 mL is expected to befatal to humansLC50 value, inhalation (rats): 330 mg (56ppm)/m3/4 hrLD50 value, oral (rats): 75 mg/kgLD50 value, skin (guinea pigs): 300 mg/kgLD50 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 oEmits 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
Check Digit Verification of cas no
The CAS Registry Mumber 111-44-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 1 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 111-44:
(5*1)+(4*1)+(3*1)+(2*4)+(1*4)=24
24 % 10 = 4
So 111-44-4 is a valid CAS Registry Number.
111-44-4Relevant articles and documents
A Schiff base bis(N-salicylidene)-3-oxapentane-1,5-diamine and its yttrium(III) complex: Synthesis, crystal structure, DNA-binding properties, and antioxidant activities
Wu, Huilu,Pan, Guolong,Bai, Yuchen,Wang, Hua,Kong, Jin,Shi, Furong,Zhang, Yanhui,Wang, Xiaoli
, p. 2634 - 2646 (2013)
A Schiff base bis(N-salicylidene)-3-oxapentane-1,5-diamine (H2L) and its yttrium(III) (Y(III)) complex, Y2L2(NO 3)2?2H2O, have been synthesized and characterized by physico-chemical and spectroscopic methods. The crystal structure of the Y(III) complex has been determined by single-crystal X-ray diffraction, revealing a centrosymmetric binuclear neutral entity where Y(III) centers are bridged by two phenoxo oxygens. The DNA-binding properties of the Schiff base H2L and the Y(III) complex were investigated by spectrophotometric methods and viscosity measurements. The results suggest that ligand H2L and Y(III) complex both bind to DNA via groove binding, and the Y(III) complex binds to DNA more strongly than H2L. The antioxidant activity of the Y(III) complex was determined by superoxide and hydroxyl radical-scavenging method in vitro, which indicates that Y(III) complex scavenges OH? and O2 radicals.
A dichloro diethyl ether and 2 - chloroethyl phenoxy ethanol synthesis method
-
Paragraph 0061; 0065; 0070; 0075; 0081; 0092, (2019/05/16)
The invention discloses a dichloro diethyl ether and 2 - chloroethyl phenoxy ethanol synthesis method, which belongs to the field of organic synthesis. The method comprises: the molar ratio of 0.8 - 1.5: 0.3 diethylene glycol and catalyst in a double-mouth flask, and the double-mouth flask are respectively connected with two of the mouth of the funnel and a condenser; the use of a separatory funnel to drip the mixed acid in double-mouth flask, in 130 °C - 170 °C under reaction, during the reaction, the use of condenser to collect condensate; the condensate to the distillation is carried out, to obtain dichloro diethyl ether; double-mouth flask in the remaining liquid to filter, to obtain the 2 - chloroethyl phenoxy ethanol, wherein mixed acid include: mass ratio is 25 - 35:1 of concentrated hydrochloric acid is concentrated sulfuric acid. The embodiment of the invention the synthesis method provided not only can at the same time obtained by synthesizing dichloro diethyl ether and 2 - chloroethyl phenoxy ethanol, but also, the method reaction is simple and controllable, mild reaction conditions, raw materials are safe and easily-obtained, so that the synthesis of the two more safe and controllable, the cost is cheaper.
Double (2-haloethyl) ether synthesis method
-
Paragraph 0020-0021, (2017/02/24)
The invention relates to the synthesis of fine chemical intermediates, in particular to a synthesis method of di(2-halogenated ethyl) ether. According to the synthesis method, 1,4-thioxane-1,1-dioxo and a hydrogen halide water solution react with each other to obtain the target product, namely di(2-halogenated ethyl) ether. The synthesis method is simple and convenient in technical route, good in selectivity, high in yield, less in pollution and simple in post-processing, conforms to the tendency of the green chemical industry nowadays, and has great industrial value.
