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解説
エチレンクロロヒドリン．エテンと塩素の混合ガスを水に通じて生成させる．工業製品は，純度42.5％ の含水物(共沸混合物，沸点96 ℃)が多いが，無水物とすることもできる．無色の油状液体．沸点128.5 ℃．d15 1.2072．水と混和し，エチレングリコールや殺虫剤の製造原料，ジャガイモ，ブドウなどの発芽促進剤として使われる．麻酔性がある．LD50 81 mg/kg(マウス，経口)．有毒でとくに皮膚に触れないように注意する。
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用途
医薬・・農薬の中間体
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用途
医薬品、農薬、染料などの中間体、重合調整剤、架橋剤
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説明
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.
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化学的特性
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.
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物理的性質
Colorless liquid with a faint, ether-like odor. Odor threshold concentration is 400 ppb (quoted,
Keith and Walters, 1992).
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使用
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.
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定義
ChEBI: 2-chloroethanol is a chloroethanol carrying a chloro substituent at position 2. It has a role as a xenobiotic metabolite.
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調製方法
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.
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一般的な説明
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.
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空気と水の反応
Highly flammable. 2-Chloroethanol is soluble in water.
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反応プロフィール
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.).
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危険性
Deadly via ingestion, inhalation, and skin
absorption; strong irritant, penetrates ordinary rubber gloves and protective clothing. Moderate fire
hazard. Questionable carcinogen.
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健康ハザード
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.
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火災危険
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.
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化学反応性
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.
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安全性プロファイル
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.
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職業ばく露
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
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発がん性
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.
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環境運命予測
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).
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輸送方法
UN1135 Ethylene chlorohydrin, Hazard class:
6.1; Labels: 6.1-Poison Inhalation Hazard, 3-Flammable
liquid, Inhalation Hazard Zone B
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純化方法
Dry it with, then distil it from, CaSO4 in the presence of a little Na2CO3 to remove traces of acid. [Beilstein 1 IV 1372.]
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不和合性
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
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廃棄物の処理
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.
