Chemical Properties
colourless liquid
Definition
ChEBI: An epoxide that is 1,2-epoxypropene in which one of the methyl hydrogens is substituted by chlorine.
Uses
Solvent for natural and synthetic resins, gums, cellulose esters and ethers, paints, varnishes, nail enamels and lacquers, cement for Celluloid. As stabilizer.
General Description
A clear colorless liquid with an irritating chloroform-like odor. Density 9.8 lb/gal. Flash point 87°F. Polymerizable. If polymerization takes place inside a closed container, the container is subject to violent rupture. Irritates the skin and respiratory system. Toxic by ingestion. A confirmed carcinogen. Vapors heavier than air. Used to make plastics and as a solvent.
Reactivity Profile
1-CHLORO-2,3-EPOXYPROPANE(106-89-8) may polymerize exothermically if heated or contaminated. Reacts explosively with aniline. Ignites on contact with potassium tert-butoxide. Reacts with trichloroethylene to give the explosive dichloroacetylene. Violent reaction with sulfuric acid or isopropylamine. Exothermic polymerization on contact with strong acids or bases, zinc, aluminum, aluminum chloride, iron, ferric chloride [Sax, 9th ed., 1996, p. 1469].
Air & Water Reactions
Highly flammable. Water soluble.
Hazard
Toxic by inhalation, ingestion, and
skin absorption; strong irritant, a carcinogen.
Flammable, moderate fire risk. TLV: 0.5 ppm; animal carcinogen.
Health Hazard
This compound is caustic as both a liquid and gas. Irritation of the eyes and skin, and skin sensitization has been observed. Exposure to epichlorohydrin has caused inflammation of the lungs, asthmatic bronchitis, and liver and kidney damage. In acute poisonings, death may be caused by respiratory paralysis.
Potential Exposure
Epichlorohydrin, an organochlorine, is
used in the manufacture of many glycerol and glycidol derivatives and epoxy resins; as a stabilizer in chlorine-containing
materials; as an intermediate in the preparation of cellulose
esters and ethers, paints, varnishes, nail enamels, and lacquers;
as a cement for celluloid. It is used as an intermediate in the
manufacture of various drugs. Increased cancer risk.
Fire Hazard
When heated to decomposition, this compound evolves highly toxic fumes of phosgene and carbon monoxide. Reactive and incompatible with strong oxidizers, strong acids, caustics, zinc, aluminum, chlorides of iron and aluminumand compounds with an active hydrogen atom, including water. Unstable, avoid heat, contaminants, strong acids and bases, certain curing agents such as ethylenediamine. Hazardous polymerization may occur.
First aid
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce
vomiting. Do not make an unconscious person vomit.
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
UN2023 Epichlorhydrin, Hazard class: 6.1;
Labels: 6.1-Poisonous materials, 3-Flammable liquid.
Incompatibilities
May form explosive mixture with air.
Slowly decomposes on contact with water. Heat or strong
acids; alkalies, metallic halides, or contaminants can cause
explosive polymerization. Violent reaction with strong oxidizers, aliphatic amines; alkanolamines, amines (especially
aniline), alkaline earths; chemically active metals (chlorides
of aluminum, iron zinc); powdered metals (aluminum,
zinc); alcohols, phenols, organic acids; causing fire and
explosion hazard. Will pit steel in the presence of water.
Thermal decomposition forms highly toxic phosgene gas.
May accumulate static electrical charges, and may cause
ignition of its vapors.
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
Physical properties
Clear, colorless, mobile liquid with a strong, irritating, chloroform-like odor. Odor threshold
concentration is 0.93 ppm (quoted, Amoore and Hautala, 1983).
Production Methods
Epichlorohydrin can be prepared from 1,3-dichloropropanol-2, 2,3- dichloropropanol-1, or allyl chloride. Commercially it is prepared as an intermediate in glycerol synthesis via alkaline hydrolysis of glycerol dichlorohydrin. Both come from allyl chloride. Epichlorohydrin reacts with monohydric alcohols to give ethers by opening the oxide ring. It will react with ethers, aldehydes, ketones, organic acids and amines to give a wide variety of useful syntheses.
Synthesis Reference(s)
Organic Syntheses, Coll. Vol. 2, p. 256, 1943
The Journal of Organic Chemistry, 48, p. 3831, 1983
DOI: 10.1021/jo00169a052
Flammability and Explosibility
Flammable
Chemical Reactivity
Reactivity with Water Mild reaction; not likely to be hazardous; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Can polymerize in presence of strong acids and bases, particularly when hot; Inhibitor of Polymerization: None used.
Carcinogenicity
Epichlorohydrin is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.
storage
Epichlorohydrin is stored in a well-ventilated,cool place isolated from combustible andoxidizable materials, all acids and bases,and anhydrous metal halides. Protect fromphysical damage. It is shipped in metaldrums.
Purification Methods
Distil epichlorohydrin under atmospheric pressure, heat it on a steam bath with one-quarter its weight of CaO, then decant and fractionally distil it. [Beilstein 17 V 20.]
Toxicity evaluation
Epichlorohydrin is an alkylating agent that is mutagenic. It
may induce DNA interstrand cross-links, chromosomal
aberrations, and breaks. It is also an irritant, sensitizer, and
corrosive.
