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外観
無色～ほとんど無色, 澄明の液体
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性質
1,2-epoxy-3-chloropropane．C3H5ClO(92.52)．ラセミ体のものが知られている．グリセリンから得られるα,γ-ジクロロヒドリン，またはプロピレンから得られる2,3-ジクロロプロピルアルコールをアルカリで脱塩化水素して合成される．特異臭をもつ無色の液体．融点－25.6 ℃，沸点117.9 ℃，引火点40.6 ℃．d20"1.1812．水に不溶，普通の有機溶媒に易溶．活性水素をもつ化合物と反応して種々の開環付加物をつくる．フェノールまたは有機酸の金属塩と反応してグリシジルエーテルまたはエステルをつくる．森北出版「化学辞典（第2版）
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溶解性
水に難溶 (6g/100ml水, 10℃), アルコール, エーテル等各種有機溶剤と混和。エタノール及びアセトンに極めて溶けやすく、水にほとんど溶けない。
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用途
有機合成原料。
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用途
エポキシ樹脂、界面活性剤
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用途
エポキシ樹脂、各種溶媒、界面活性剤、安定剤、医薬品原料
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用途
溶剤，エポキシ樹脂原料，合成ゴム原料，塩素化ゴム安定剤として広く用いられる．有毒．エピクロロヒドリンは，液体は皮膚から吸収され，蒸気は粘膜を刺激し，長期間取り扱うと慢性の疲労，結膜炎，胃腸疾患などを起こす．
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説明
Epoxy resins of the bisphenol A type are synthesized
from epichlorhydrin and bisphenol A. This leads to
bisphenol-A diglycidyl ether, which is the monomer
of bisphenol-A-based epoxy resins. Sensitization to
epichlorhydrin occurs mainly in workers in the epoxy-resin industry. Sensitization in individuals not working
at epoxy resin plants is rare. It has however been described to occur after contact with a soil fumigant,
due to solvent cement and in a worker in a pharmaceutical
plant, in a division for drug synthesis.
Epichlorhydrin was used for the production of both
drugs propranolol and oxprenolol.
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化学的特性
Epichlorohydrin is a colorless liquid with
a slightly irritating, chloroform-like odor.
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物理的性質
Clear, colorless, mobile liquid with a strong, irritating, chloroform-like odor. Odor threshold
concentration is 0.93 ppm (quoted, Amoore and Hautala, 1983).
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使用
Epichlorohydrin is used to make glycerol,epoxy resins, adhesive, and castings; asderivatives for producing dyes, pharmaceu-ticals, surfactants, and plasticizers; and asa solvent for resins, gums, paints, andvarnishes.
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調製方法
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.
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定義
ChEBI: An epoxide that is 1,2-epoxypropene in which one of the methyl hydrogens is substituted by chlorine.
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一般的な説明
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.
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空気と水の反応
Highly flammable. Water soluble.
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反応プロフィール
Epichlorohydrin 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].
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危険性
Toxic by inhalation, ingestion, and
skin absorption; strong irritant, a carcinogen.
Flammable, moderate fire risk. TLV: 0.5 ppm; animal carcinogen.
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健康ハザード
Epichlorohydrin 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.
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火災危険
When heated to decomposition, Epichlorohydrin 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.
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使用用途
エピクロロヒドリンは、合成原料として使われています。特に自動車やエレクトロニクスの化学工業分野で、広く使われているエポキシ樹脂の主原料としての用途が多いです。エポキシ樹脂は、塗料の分野で一般的な塗料、自動車や工業用の電着塗装、ドラムや缶の内側のコーティングなどに使用されています。
また、エレクトロニクスの分野では、プリント基盤やコイル絶縁素材に使用され、土木建築分野では、コンクリートや鉄などの防食塗装、やにも使われています。
エポキシ樹脂以外にも、エピクロロヒドリンゴムやグリシジルメタクリレートの原料など、グリセリンなどの合成原料としても広く用いられ、酢酸セルロース、セロハン、エステルゴム用の溶剤としても使用されます。そのほか、化粧品、医薬品、界面活性剤、の合成原料、繊維処理剤、溶剤なども用途の1つです。
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化学反応性
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.
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接触アレルゲン
Epoxy resin of the Bisphenol A type is synthesized
from epichlorhydrin and bisphenol A. It leads to bisphenol
A diglycidyl ether, which is the monomer ofbisphenol-A-based epoxy resins. Sensitization to
epichlorhydrin occurs mainly in workers of the epoxy
resin industry. Sensitization in individuals not working
at epoxy resin plants is rare. It has, however, been
described to occur following exposure to a soil fumigant,
due to solvent cement, and in a worker in a pharmaceutical
plant, in a division of drug synthesis.
Epichlorhydrin was used for the production of drugs
propranolol and oxprenolol.
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安全性プロファイル
Confirmed carcinogen
with experimental carcinogenic data. Poison
by ingestion, skin contact, intravenous, and
intraperitoneal routes. Moderately toxic by
inhalation. An experimental teratogen.
Other experimental reproductive effects.
Human systemic effects by inhalation:
respiratory, nose, and eyes. Human mutation
data reported. A skin and eye irritant. A
sensitizer. Flammable liquid when exposed
to heat or flame. Explosive reaction with
andine. Reaction with trichloroethylene
forms the explosive dichloroacetylene.
Ignition on contact with potassium tertbutoxide. Violent reaction with sulfuric acid
or isopropylamine. Exothermic
polymerization on contact with strong acids,
caustic alkalies, aluminum, aluminum
chloride, iron(II1) chloride, or zinc. When
heated to decomposition it emits toxic
fumes of Cl
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職業ばく露
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.
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概要
エピクロロヒドリンとは、エポキシ基と塩素基をもつ反応性の高いモノマー (単量体) です。
別名で2-クロロメチルオキシラン、1-クロロ-2,3-エポキシプロパン、γ-クロロプロピレンオキシドとも呼ばれます。エピクロロヒドリンは、腐食性があり、眼、鼻、喉を刺激します。
吸入すると、頭痛やめまいなど中枢神経障害を起こす恐れがあります。
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発がん性
Epichlorohydrin is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.
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製造方法
エピクロロヒドリンの製造方法
エピクロロヒドリンの製造方法は、とを反応させて得られるアリルクロライドを原料にして生産する方法と、プロピレンと酢酸を反応させて得られるアリルアルコールを原料に生産する方法の2種類があります。
1. アリルクロライド法
アリルクロライドを次亜塩素酸溶液と反応させて、ジクロロプロパノールを得ます。これをアルカリと反応させて脱塩酸させることで、粗エピクロロヒドリンを作り、蒸留により不純物を取り除いて生産されます。
CH2=CHCH3 + Cl2 → CH2=CHCH2Cl + HCl (アリルクロライドの合成)
CH2=CHCH2Cl + HOCl → CH2ClCH(OH)CH2Cl
CH2ClCH(OH)CH2Cl → CH2CHOCH2Cl + HCl
2. アリルアルコール法
アリルアルコールを塩酸水溶液中で塩素により塩素化してジクロロプロパノールを得ます。これにアルカリを加えることで脱塩酸して、粗エピクロロヒドリンを作り、蒸留により製品のエピクロロヒドリンを得ます。
2CH2=CHCH3 + 2CH3COOH + O2 →CH2=CHCH2OCOCH3 +H2O→ CH2=CHCH2OH + CH3COOH (アリルアルコールの合成)
CH2=CHCH2OH + Cl2 → CH2ClCH(OH)CH2Cl
CH2ClCH(OH)CH2Cl → CH2CHOCH2Cl + HCl
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環境運命予測
Biological. Bridié et al. (1979) reported BOD and COD values of 0.03 and 1.16 g/g using
filtered effluent from a biological sanitary waste treatment plant. These values were determined
using a standard dilution method at 20 °C for a period of 5 d. When a sewage seed was used in a
separate screening test, a BOD value of 0.16 g/g was obtained. The ThOD for epichlorohydrin is
1.21 g/g.
Chemical/Physical. Anticipated products from the reaction of epichlorohydrin with ozone or
OH radicals in the atmosphere are formaldehyde, glyoxylic acid, and ClCH2O(O)OHCHO (Cupitt,
1980). Haag and Yao (1992) reported a calculated OH radical rate constant in water of 2.9 x
108/M?sec.
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貯蔵
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.
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合成方法
（1）クロロヒドリン法：プロピレンの高温気相塩素化で得られる塩化アリルを次亜塩素酸溶液と作用させクロロヒドリン化すると，ジクロロヒドロキシプロパンの2種類の異性体混合物が得られる。次いで，この粗生成物を水酸化カルシウムと反応させるとエピクロロヒドリンになる。（2）アリルアルコール法：アリルアルコールに塩酸溶液中で塩素を付加させて2,3-ジクロロ-1-プロパノールとし，次いで水酸化カルシウムと反応させるとエピクロロヒドリンとなる。
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輸送方法
UN2023 Epichlorhydrin, Hazard class: 6.1;
Labels: 6.1-Poisonous materials, 3-Flammable liquid.
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純化方法
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.]
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不和合性
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.
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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. 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
