Chemical Properties
Ethylene dichloride is one of the highest volume chemicals used in the United States. It is
a colorless oily liquid with a chloroform-like odor, detectable over the range of 6–40 ppm,with a sweet taste. Ethylene dichloride (1,2-dichloroethane), which has a carbon-carbon
single bond, should be distinguished from 1,2-dichloroethene, which has a carbon-carbon
double bond. It is a skin irritant. Ethylene dichloride is also used as an extraction solvent,
as a solvent for textile cleaning and metal degreasing, in certain adhesives, and as a component
in fumigants for upholstery, carpets, and grain. Other miscellaneous applications
include paint, varnish, and fi nish removers, soaps and scouring compounds, wetting and
penetrating agents, organic synthesis, ore fl otation, and as a dispersant for nylon, rayon,
styrene-butadiene rubber, and other plastics.
General Description
A clear colorless liquid with a chloroform-like odor. Flash point 56°F. Denser than water and insoluble in water. Vapors are heavier than air. Density 10.4 lb/gal.
Reactivity Profile
Liquid ammonia and ETHYLENE DICHLORIDE(107-06-2) can cause an explosion when mixed, NFPA 491M, 1991. A tank of dimethyl amino propyl amine exploded violently when ETHYLENE DICHLORIDE(107-06-2) reacted with wet ETHYLENE DICHLORIDE(107-06-2) which had been the tank's previous contents [Doyle 1973]. Halogenated aliphatic compounds, such as ETHYLENE DICHLORIDE(107-06-2), are moderately or very reactive. Reactivity generally decreases with increased degree of substitution of halogen for hydrogen atoms. Materials in this group are incompatible with strong oxidizing and reducing agents. Also, they are incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, epoxides, aluminum
Air & Water Reactions
Highly flammable. Slightly water soluble.
Hazard
Toxic by ingestion, inhalation, and skin
absorption; strong irritant to eyes and skin; a carcinogen. Flammable, dangerous fire risk, explosive
limits in air 6–16%. Possible carcinogen.
Health Hazard
Exposures to ethylene dichloride cause CNS depression (dizziness, drowsiness, trembling,
unconsciousness), nausea, vomiting, abdominal pain, skin irritation, dermatitis, eye irritation,
corneal opacity, blurred vision, headache, sore throat, cough, bronchitis, pulmonary
edema (may be delayed), liver, kidney, cardiovascular system damage, cardiac arrhythmia,
acute abdominal cramps, diarrhea, internal bleeding (hemorrhagic gastritis and colitis),
and respiratory failure. Ethylene dichloride involves the kidneys, liver, eyes, skin, CNS,
and the cardiovascular system as the target organs. Ethylene dichloride is known to cause
systemic effects and has been identifi ed as a priority pollutant in many countries.
Prolonged periods of inhalation of the vapors of ethylene dichloride irritate the respiratory
tract. Symptoms of severe toxicity are CNS effects, liver damage, kidney damage,
adrenal gland damage, cyanosis, weak and rapid pulse, and unconsciousness. Death can
occur from respiratory and circulatory failure.
The acute effects of ethylene dichloride are similar for all routes of entry: ingestion, inhalation,
and skin absorption. Acute exposures result in nausea, vomiting, dizziness, internal
bleeding, bluish-purple discoloration of the mucous membranes and skin (cyanosis), rapid
but weak pulse, and unconsciousness. Acute exposures can lead to death from respiratory
and circulatory failure. Autopsies in such situations have revealed widespread bleeding
and damage in most internal organs. Repeated long-term exposures to ethylene dichloride
have resulted in neurologic changes, loss of appetite, and other gastrointestinal problems,
irritation of the mucous membranes, liver and kidney impairment, and death.
Health Hazard
Inhalation of vapors causes nausea, drunkenness, depression. Contact of liquid with eyes may produce corneal injury. Prolonged contact with skin may cause a burn.
Potential Exposure
In recent years, 1,2-dichloroethane is
used in the production of vinyl chloride and as a leadscavenging agent in petrol; it has found wide use in the
manufacture of ethylene glycol, diaminoethylene, polyvinyl
chloride; nylon, viscose rayon; styrenebutadiene rubber,
and various plastics. It is a solvent for resins, asphalt, bitumen, rubber, cellulose acetate; cellulose ester; and paint; a
degreaser in the engineering, textile, and petroleum industries; and an extracting agent for soybean oil and caffeine.
It is also used as an antiknock agent in gasoline; a pickling
agent; a fumigant; and a dry-cleaning agent. It has found
use in photography, xerography, and water softening; and
also in the production of adhesives, cosmetics, pharmaceuticals, and varnishes.
First aid
Move victim to fresh air. Call 911 or emergency
medical service. Give artificial respiration if victim is not
breathing. Do not use mouth-to-mouth method if victim
ingested or inhaled the substance; give artificial respiration
with the aid of a pocket mask equipped with a one-way
valve or other proper respiratory medical device.
Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact
with substance, immediately flush skin or eyes with running
water for at least 20 minutes. For minor skin contact, avoid
spreading material on unaffected skin. Keep victim warm
and quiet. Effects of exposure (inhalation, ingestion or skin
contact) to substance may be delayed. Ensure that medical
personnel are aware of the material(s) involved and take
precautions to protect themselves. Medical observation is
recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for
pulmonary edema, a doctor or authorized paramedic may
consider administering a drug or other inhalation therapy.with substance, immediately flush skin or eyes with running
water for at least 20 minutes. For minor skin contact, avoid
spreading material on unaffected skin. Keep victim warm
and quiet. Effects of exposure (inhalation, ingestion or skin
contact) to substance may be delayed. Ensure that medical
personnel are aware of the material(s) involved and take
precautions to protect themselves. Medical observation is
recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for
pulmonary edema, a doctor or authorized paramedic may
consider administering a drug or other inhalation therapy.
Shipping
UN1184 Ethylene dichloride, Hazard Class: 3;
Labels: 3-Flammable liquid, 6.1-Poisonous materials. Note:
United States DOT 49CFR172.101, Inhalation Hazardous
Chemical as 1,2-Dichloroethane
Incompatibilities
May form explosive mixture with air.
Reacts violently with strong oxidizers and caustics;
chemically active metals, such as magnesium or aluminum powder, sodium and potassium; alkali metals;
alkali amides; liquid ammonia. Decomposes to
vinyl chloride and HCl above 600℃. Attacks plastics,
rubber, coatings. Attacks many metals in presence of
water.
Description
1,2-Dichloroethane, also called ethylene dichloride (EDC), is a manufactured chemical that is not found naturally in the environment. It is used principally to synthesize vinyl chloride, which is further used to produce a variety of vinyl based plastics products, such as polyvinyl chloride (PVC) pipes, furniture, automobile upholstery, wall coverings, housewares, and automobile parts. It is used in solvents in closed systems for various extraction and cleaning purposes in organic synthesis. It is used as a leaded gasoline additive to remove lead, but with declining tendency. It is used as a dispersant in rubber and plastics, as a wetting and penetrating agent. It was used in ore flotation, as a metal degreaser, and in textile and PVC cleaning. It was also used as an insect fumigant for stored grains and in mushroom houses, a soil fumigant in peach and apple orchards. But due to its toxicity, it is no longer registered for use as an insect fumigant in the United States (IARC 1999).
1,2-Dichloroethane structure
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
Physical properties
Clear, colorless, oily liquid with a pleasant, chloroform-like odor. The average least detectable
odor threshold concentrations in water at 60 °C and in air at 40 °C were 12 and 52 mg/L,
respectively (Alexander et al., 1982). Experimentally determined detection and recognition odor
threshold concentrations were 25 mg/m3 (6 ppmv) and 165 mg/m3 (41 ppmv), respectively
(Hellman and Small, 1974).
Uses
1,2-Dichloroethane is used in the manufacture of acetyl cellulose and vinyl chloride; inpaint removers; as a fumigant; as a degreaser;as a wetting agent; and as a solvent for oils,waxes, gums, resins, and rubber. It has been used as insect and soil fumigant.
Application
1,2-dichloroethane (Ethylene dichloride), also known as EDC, is produced by reacting chlorine or anhydrous hydrochloric acid with ethylene. The largest single use for EDC is the production of vinyl chloride monomer, which is used to produce poly vinyl chloride (PVC). It has many uses in industry, with principal ones being the following:
As an intermediate in the manufacture of methyl chloroform, perchloroethylene, ethylene amines, polyvinyl chloride (PVC), sulfide compounds, vinyl chloride, and trichloroethane.
As an additive in gasoline (used as a lead scavenger), pharmaceutical products, color film, and pesticides.
As a solvent for rubber, tobacco extract, paint, printing inks, and varnish.
Miscellaneous uses include as an ingredient in fingernail polish, for metal degreasing, in extracting spices, and as a dry cleaning agent.
Definition
ChEBI: A member of the class of chloroethanes substituted by two chloro groups at positions 1 and 2.
Preparation
The first synthesis of 1,2-dichloroethane was achieved in 1795. 1,2-Dichloroethane is industrially produced by chlorination of ethylene. This chlorination can either be carried out by using chlorine (direct chlorination) or hydrogen chloride (oxychlorination) as a chlorinating agent. It is also produced by oxychlorination—ethylene, hydrogen chloride, and air are reacted at about 250 °C with a copper chloride catalyst. In the United States, almost all ethylene dichloride produced at present is used as the starting material for preparation of vinyl chloride monomer.
Production Methods
Ethylene dichloride (EDC) is produced by reacting ethylene and chlorine in the presence of ferric chloride, using the liquid product as solvent. It is also produced by oxychlorination—ethylene, hydrogen chloride, and air are reacted at about 250 °C with a copper chloride catalyst.
Production Methods
In the United States, almost all ethylene dichloride produced
at present is used as the starting material for preparation of
vinyl chloride monomer. Other applications are much smaller.
Fire Hazard
Flammable liquid; burns with a smoky flame;
flash point (closed cup) 13°C (56°F), (open
cup) 18°C (65°F); vapor pressure 62 torr at
20°C (68°F); the vapor is heavier than air and
can travel a considerable distance to a source
of ignition and flash back; autoignition tem perature 413°C (775°F); fire-extinguishing
agent: dry chemical, CO2, or foam; water
may be used to keep fire-exposed contain ers cool and to disperse the vapors and flush
away any spill.
1,2-Dichloroethane forms explosive mix tures with air, with LEL and UEL val ues of 6.2% and 16.0% by volume in air,
respectively. Its reactions with alkali met als, powdered aluminum, or magnesium can
be violent. It forms explosive mixtures with
nitrogen tetroxide.
Flammability and Explosibility
Highlyflammable
Agricultural Uses
Fumigant, Insecticide: Not approved for use in EU countries. Not registered
for use in the U.S. When mixed with carbon tetrachloride,
ethylene dichloride is used as a grain fumigant
for bulk storage in bags, sealed containers, bins or on
floors. In recent years, 1,2-dichloroethane has found wide
use in the manufacture of ethylene glycol, diaminoethylene,
polyvinyl chloride, nylon, viscose rayon, styrenebutadiene
rubber, and various plastics. It is a solvent for
resins, asphalt, bitumen, rubber, cellulose acetate, cellulose
ester, and paint; a degreaser in the engineering, textile
and petroleum industries; and an extracting agent for soybean
oil and caffeine. It is also used as an antiknock agent
in gasoline, a pickling agent and a dry-cleaning agent. It
has found use in photography, xerography, water softening,
and also in the production of adhesives, cosmetics, pharmaceuticals,
and varnishes.
Trade name
BORER SOL®; BROCIDE®; DESTRUXOL
BORER-SOL®; DOWFUME®[C]; DUTCH LIQUID®;
DUTCH OIL®
Carcinogenicity
1,2-Dichloroethane is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Source
Improper use of insecticidal fumigant formulation containing 1,2-dichloropropane and
carbon tetrachloride (Granosan).
Environmental Fate
Biological. Methanococcus thermolithotrophicus, Methanococcus deltae, and
Methanobacterium thermoautotrophicum metabolized 1,2-dichloroethane releasing methane and
ethylene (Belay and Daniels, 1987). 1,2-Dichloroethane showed slow to moderate biodegradative
activity with concomitant rate of volatilization 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 63 and 53, respectively. At a substrate concentration of 5
mg/L, 27% was lost due to volatilization after 10 d (Tabak et al., 1981).
Photolytic. Titanium dioxide suspended in an aqueous solution and irradiated with UV light (λ
= 365 nm) converted 1,2-dichloroethane to carbon dioxide at a significant rate (Matthews, 1986).
The rate constant for the reaction of 1,2-dichloroethane and OH radicals in the atmosphere at
300 K is 1.3 x 10-11 cm3/molecule?sec (Hendry and Kenley, 1979). At 296 K, a photooxidation rate
constant of 2.2 x 10-13 cm3/molecule?sec was reported for the reaction with OH radicals resulting
in a half-life of 1.7 months (Howard and Evenson, 1976).
Chemical/Physical. Anticipated products from the reaction of 1,2-dichloroethane with ozone or
OH radicals in the atmosphere are chloroacetaldehyde, chloroacetyl chloride, formaldehyde, and
ClHCHO (Cupitt, 1980).
Metabolic pathway
Resting cell suspensions of the soil methylotroph
Methylosinus trichosporium OB-3b rapidly
dehalogenate 1,2-dichloroethane, resulting in the
formation of chloroethanol via direct hydroxylation of
one of the C-Cl bonds, and this ethanol is rapidly
oxidized to yield chloroacetic acid.
Purification Methods
It is usually prepared by chlorinating ethylene, so that likely impurities include higher chloro derivatives and other chloro compounds depending on the impurities originally present in the ethylene. It forms azeotropes with water, MeOH, EtOH, trichloroethylene, CCl4 and isopropanol. Its azeotrope with water (containing 8.9% water, and b 77o) can be used to remove gross amounts of water prior to final drying. As a preliminary purification step, it can be steam distilled, and the lower layer is treated as below. Shake it with conc H2SO4 (to remove alcohol added as an oxidation inhibitor), wash with water, then dilute KOH or aqueous Na2CO3 and again with water. After an initial drying with CaCl2, MgSO4 or by distillation, it is refluxed with P2O5, CaSO4 or CaH2 and fractionally distilled. Carbonyl-containing impurities can be removed as described for chloroform. [Beilstein 1 IV 131.]
Degradation
Ethylene dichloride (1) had been detected in surface and ground water as
an environmental contaminant, resulting from both industrial and
agricultural uses. It is also detected following the chlorination of drinking
water. Ethylene dichloride is stable to hydrolytic degradation at
environmentally relevant pH and temperature.
The primary dissipation mechanism of ethylene dichloride is volatilisation
(DT50 30 min, Moore et al., 1991). Ethylene dichloride interacts with
hydroxyl radicals produced by photo-oxidation in air to yield chloracetyl
chloride (2, Howard and Evenson, 1976; Radding et al., 1977).
The DT50 of ethylene dichloride in the vapour phase under atmospheric
photo-oxidation conditions was 12-122 days (Atkinson, 1985).
Toxicity evaluation
1,2-Dichloroethane can enter the environment when it is made,
packaged, shipped, or used. Most 1,2-dichloroethane is released
to the air, although some is released to rivers or lakes.
1,2-Dichloroethane could also enter soil, water, or air in large
amounts in an accidental spill (evaporates into the air very fast
from soil and water). If released to air, a vapor pressure of
78.9mmHg at 25°Cindicates that 1,2-dichloroethane will exist
solely as a vapor in the ambient atmosphere. Vapor-phase
1,2-dichloroethane will be degraded in the atmosphere by
reaction with photochemically produced hydroxyl radicals; the
half-life for this reaction in air is estimated to be 63 days. Indirect
evidence for photooxidation of 1,2-dichloroethane comes
from the observation that monitoring levels are highest during
the night and early morning. It may also be removed from air
in rain or snow. Since it stays in the air for a while, the wind may
carry it over large distances. In water, 1,2-dichloroethane breaks
down very slowly and most of it will evaporate to the air. Only
very small amounts are taken up by plants and fish. Exact
longevity of 1,2-dichloroethane in water remains unknown.
It is thought that it remains longer in lakes than in rivers.
In soil, it either evaporates into the air or travels down
through soil and enters underground water. 1,2-Dichloroethane
has been found in the United States drinking water at levels
ranging from 0.05 to 64 ppb. An average amount of 175 ppb has
been found in 12%of the surface water and groundwater samples
taken at 2783 hazardous wastes sites. 1,2-Dichloroethane has
also been found in the air near urban areas at levels of
0.10–1.50 ppb and near hazardous waste sites at levels of
0.01–0.003 ppb. Small amounts of 1,2-dichloroethane have also
been found in foods. Small organisms living in soil and
groundwater may transform it into other, less harmful
compounds, although this happens slowly. Large amounts from
an accident, hazardous waste site, or landfill may likely reach
the underground and contaminate drinking water wells.
Biodegradation occurs slowly in water and soil surfaces. It is
not expected to undergo hydrolysis and photolysis. Humans
may get exposed to very lowlevels of 1,2-dichloroethane through
its use as a gasoline additive (leaded gasoline is no longer used
in the United States).
References
https://www.atsdr.cdc.gov/substances/toxsubstance.asp?toxid=110
[2] http://apps.who.int/iris/bitstream/10665/42027/1/9241530014.pdf
[3] https://www.epa.gov/sites/production/files/2016-09/documents/ethylene-dichloride.pdf