2-Chloroethanol

Description

Ethylene chlorohydrine is a clear, colourless liquid with mild, ethereal odour. It reacts with alkali metals. Ethylene chlorohydrine has applications as a laboratory reagent and as a pharmaceutical intermediate. Ethylene chlorohydrine is a building block in the production of pharmaceuticals, biocides, and plasticisers, used for manufacture of thiodiglycol, an important solvent for cellulose acetate and ethyl cellulose, textile-printing dyes, extraction of pine lignin, in dewaxing, refining of rosin, and the cleaning of machines. Several dyes are prepared by the alkylation of aniline derivatives with chloroethanol.

Chemical properties

2-Chloroethanol is a colorless liquid with a faint, ethereal odor and is miscible with water. Among the halogenated alcohols, ethylene chlorohydrin is the most prominent, along with the chloropropanols.

Physical properties

Colorless liquid with a faint, ether-like odor. Odor threshold concentration is 400 ppb (quoted, Keith and Walters, 1992).

The Uses of 2-Chloroethanol

2-Chloroethanol, is used in the preparation of TTFTT (tetrathiafulvalene-2,3,6,7-tetrathiolate) and important building block in TTF syntheis. In addition, it is used in the synthesis of vinyltriazoles. This is the labeled analog.

The Uses of 2-Chloroethanol

Ethylene chlorohydrin (CH2Cl-CH2-OH; 2-Chloroethanol) is used for its special solvent properties. It is a chemical intermediate in the production of ethylene glycol and, in the past, ethylene oxide. This alcohol is used in the manufacturing of insecticides and as a cleaning agent for machines. Indirect exposure can result from release as a by-product in applications involving ethylene oxide and its accumulation in some foodstuffs as a result of sterilization or packaging.

The Uses of 2-Chloroethanol

Ethylene chlorohydrin is used in the manufacture of insecticides, as a solvent for cellu lose esters, in treating sweet potatoes beforeplanting (Merck 1989), and in making ethylene glycol and ethylene oxide. Exposurerisks to this compound may arise when itis formed from ethylene oxide during thesterilization of grain and spices, drugs, andsurgical supplies. The compound was used inthe past in hastening grape vine sprouting.

Definition

ChEBI: 2-chloroethanol is a chloroethanol carrying a chloro substituent at position 2. It has a role as a xenobiotic metabolite.

Production Methods

2-Chloroethanol is manufactured by the reaction of ethylene gas with dilute hydrochlorous acid. The principal use of 2-chloroethanol was formerly in producing ethylene oxide, in which ethylene was reacted with hypochlorous acid. However, the current production of ethylene oxide does not use this procedure. Facilities for ethylene chlorohydrin have, in many cases, been converted to the production of propylene chlorohydrin, the dehydrochlorination of which yields propylene oxide.

General Description

2-Chloroethanol is a colorless liquid with an ether-like odor. 2-Chloroethanol is soluble in water and is also a combustible liquid. It reacts with alkali metals.Ethylene chlorohydrine has applications as a laboratory reagent and as a pharmaceutical intermediate. Ethylene chlorohydrine is a building block in the production of pharmaceuticals, biocides, and plasticisers, used for manufacture of thiodiglycol, an important solvent for cellulose acetate and ethyl cellulose, textile-printing dyes, extraction of pine lignin, in dewaxing, refining of rosin, and the cleaning of machines. Several dyes are prepared by the alkylation of aniline derivatives with chloroethanol.

Air & Water Reactions

Highly flammable. 2-Chloroethanol is soluble in water.

Reactivity Profile

Mixing 2-Chloroethanol in equal molar portions with any of the following substances in a closed container caused the temperature and pressure to increase: chlorosulfonic acid, ethylene diamine, and sodium hydroxide, [NFPA 1991]. Ethylenediamine reacts violently with 2-Chloroethanol. (Lewis, R.J., Sr. 1992. Sax's Dangerous Properties of Industrial Materials, 8th Edition. New York: Van Nostrand Reinhold. pp. 1554.).

Hazard

Deadly via ingestion, inhalation, and skin absorption; strong irritant, penetrates ordinary rubber gloves and protective clothing. Moderate fire hazard. Questionable carcinogen.

Health Hazard

Ethylene chlorohydrin is a severe acute poi son. The target organs are CNS, cardiovascu lar system, kidney, liver, and gastrointestinalsystem. The symptoms of acute toxicity arerespiratory distress, paralysis, brain damage,nausea, and vomiting. In addition, ethylenechlorohydrin can cause glutathione depletionin liver and formation of polyuria in kidney.
Ingestion of 20–25 mL can be fatal tohumans. Death may occur in 48 hours dueto metabolic acidosis and respiratory failure.Ethanol therapy apparently produced no ben efit in treatment (Deng et al. 2001). It maybe more toxic by skin contact than by oralintake. Inhalation of its vapors can producenausea, vomiting, headache, chest pain, andstupor (ACGIH 1986). At high concentra tions, death may occur. Exposure to 300 ppmfor 2 hours can be fatal to humans.
LD50 value, oral (mice): 81 mg/kgLD50 value, intraperitoneal (mice): 97 mg/kg
Ethylene chlorohydrin is an irritant to theskin, eyes, nose, and mucous membranes.It is a confirmed mutagen by the Ames testin Salmonella typhimurium. It inhibits thegrowth of DNA-deficient bacteria. Exposureto this compound increased the chromosomeaberration in the bone marrow of rats. Theodor threshold is 0.4 ppm.
A 2-year dermal study showed no evidenceof carcinogenicity of ethylene chlorohydrin onrodents (NTP 2004). The compound, however,caused malformed fetus and maternal mortality in experimental animals.

Fire Hazard

2-Chloroethanol decomposition products will react with water or steam to produce toxic and corrosive fumes of phosgene and hydrogen chloride. Vapors are heavier than air and may flash back to a source of ignition.

Flammability and Explosibility

Flammable

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: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Safety Profile

A poison by ingestion, inhalation, skin contact, intraperitoneal, intravenous, and subcutaneous routes. Moderately toxic to humans by inhalation. It can affect the nervous system, liver, spleen, and lungs. An experimental teratogen. Mutation data reported. A severe eye and mild skin irritant. Flammable liquid when exposed to heat, flame, or oxidizers. To fight fire, use alcohol foam, CO2, dry chemical. Violent reaction with chlorosulfonic acid, ethylene hamine, sodmm hydroxide. Reacts with water or steam to produce toxic and corrosive fumes. Potentially violent reaction with oxidizing materials. When heated to decomposition it emits highly toxic fumes of Cland phosgene. See also CHLORINATED HYDROCARBONS, ALIPHATIC.

Potential Exposure

Ethylene chlorohydrin is used as a solvent and emulsifier; in the synthesis of ethylene glycol, ethylene oxide, amines, carbitols, indigo, malonic acid, novocaine, and in other reactions where the hydroxyethyl group is introduced into organic compounds; for the separation of butadiene from hydrocarbon mixtures; in dewaxing and removing cycloalkanes from mineral oil; in the refining of rosin; in the manufacture of certain pesticides and in the extraction of pine lignin. In the lacquer industry, it is used as a solvent for cellulose acetate, cellulose esters, resins and waxes; and in the dyeing and cleaning industry, it is used to remove tar spots; as a cleaning agent for machines; and as a solvent in fabric dyeing. It has also found use in agriculture in speeding up sprouting of potatoes and in treating seeds to inhibit biological activity. Making chemical warfare agents

First aid

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.Medical observation is recommended for 24- 48 h afterbreathing overexposure, as pulmonary edema may bedelayed. As first aid for pulmonary edema, a doctor orauthorized paramedic may consider administering a corticosteroid spray.

Carcinogenicity

No evidence of carcinogenicity was observed in rats that ingested doses of 4, 8, or 16 mg/kg 2-chloroethanol in drinking water for up to 2 years. The study was not reported in detail, and small numbers of animals were used. F344 rats were given subcutaneous injections twice weekly at doses of 0.3, 1, 3, or 10 mg/kg for 1 year, followed by a 6-month observation period. An increased incidence of pituitary gland adenomas was observed in female rats; the incidence in the dosed female rats (all doses combined) was 7/100 and the control incidence was 1/50. 2-Chloroethanol was not carcinogenic in NMRI mice given subcutaneous injections once weekly for 70 weeks at doses of 0.3, 1.0, or 3mg . In an NTP study, 2-chloroethanol was applied dermally to F344 rats and CD-1mice for 2 years, at doses of 50 and 100 mg/kg for rats and 7.5 and 15 mg per animal for mice. There was no evidence of carcinogenicity.

Environmental Fate

Biological. Heukelekian and Rand (1955) reported a 10-d BOD value of 0.50 g/g which is 50.0% of the ThOD value of 1.00 g/g.
Chemical/Physical. Reacts with aqueous sodium bicarbonate solutions at 105 °C producing ethylene glycol (Patnaik, 1992).

storage

Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with thischemical you should be trained on its proper handling andstorage. Before entering confined space where this chemicalmay be present, check to make sure that an explosivecon-sources, and separated from strong oxidizers or caustics.Sources of ignition, such as smoking and open flames, areprohibited where this chemical is used, handled, or stored ina manner that could create a potential fire or explosion hazard. Metal containers involving the transfer of 5 gallons ormore of this chemical should be grounded and bonded.Drums must be equipped with self-closing valves, pressurevacuum bungs, and flame arresters. Use only nonsparkingtools and equipment, especially when opening and closingcontainers of this chemical.centration does not exist. Keep in a cool, well-ventilated area, protected from physical damage, ignition

Shipping

UN1135 Ethylene chlorohydrin, Hazard class: 6.1; Labels: 6.1-Poison Inhalation Hazard, 3-Flammable liquid, Inhalation Hazard Zone B

Purification Methods

Dry it with, then distil it from, CaSO4 in the presence of a little Na2CO3 to remove traces of acid. [Beilstein 1 IV 1372.]

Incompatibilities

May form explosive mixture with air. Strong oxidizers may cause fire and explosions. Incompatible with strong caustics (formation of ethylene gas), strong acids; alkaline metals; aliphatic amines; isocyanates. Violent reaction with ethylene diamine, chlorosulfonic acid. Attacks some plastics, rubber and coatings. Reacts with water or steam producing toxic and corrosive fumes

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.