クロロアセトニトリル 化学特性,用途語,生産方法
外観
無色～うすい黄色, 澄明の液体
溶解性
水に不溶。エタノール及びアセトンに溶ける。
用途
農薬、燻蒸剤、中間体
使用
Chloroacetonitrile is used in the electrochemical synthesis of cyanoacetic acid with carbon dioxide. It is involved in phase-transfer-catalyzed Darzen's condensation reaction with cyclohexanone. It is also used as an eluent additive in thermospray liquid chromatography/mass spectrometry. Further, it is used to prepare polysubstituted pyrido[1,2-a]benzimidazole by reacting with other reactant such as malononitrile, aromatic aldehyde and pyridine.
製造方法
In a 3-L round-bottomed, threenecked flask fitted with an efficient mechanical stirrer, a reflux condenser, and a thermometer were placed phosphorus pentoxide (170 g, 1.2 mol), chloroacetamide 1423 (187 g, 2 mol), and dry technical grade trimethylbenzene (800 mL). The mixture was gently refluxed with vigorous stirring for 1 h. It was then allowed to cool to about 100 C° with continuous stirring, and the reflux condenser was replaced with a distillation head fitted with a thermometer and a water-cooled condenser. The crude product and part of the solvent were distilled at atmospheric pressure. The yield of crude product boiling at 124–128 C° was 121–131 g (80–87%). In order to obtain a pure product, the crude chloroacetonitrile was mixed with phosphorus pentoxide (10 g) and redistilled through an efficient packed fractionating column. The yield of pure chloroacetonitrile distilling at 123–124 C° was 93–106 g (62–70%).
一般的な説明
A colorless liquid with a pungent odor. Flash point 118°F. Insoluble in water and denser than water. Hence, sinks in water. Very toxic by ingestion, inhalation and skin absorption. A lachrymator. Used to make other chemicals and as a fumigant.
空気と水の反応
Flammable. Insoluble in water and denser than water. Hence, sinks in water. Reacts with water and steam to produce toxic vapors of hydrogen chloride.
反応プロフィール
Chloroacetonitrile reacts with water, steam, strong acids or acid fumes to produce toxic vapors of hydrogen chloride. When heated to decomposition, Chloroacetonitrile emits highly toxic fumes of hydrogen cyanide and hydrogen chloride [Sax, 2nd ed., 1963, p. 600].
危険性
Irritant. Questionable carcinogen.
健康ハザード
TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
火災危険
HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
安全性プロファイル
Poison by ingestion,
skin contact, and intraperitoneal routes.
Moderately toxic by inhalation. A skin
irritant. Human mutation data reported.
Questionable carcinogen with experimental
tumorigenic data. Flammable liquid. See also
NITRILES. When heated to decomposition
it emits very toxic fumes of Cl-, NOx, and
CN-.
職業ばく露
A chlorinated haloacetonitrile used as
a fumigant and as a manufacturing chemical intermediate
for making other chemicals
輸送方法
UN2668 Chloroaceto nitrile Hazard class: 6.1,
Labels: 6.1-Poison Inhalation Hazard, 3-Flammable liquid
Inhalation Hazard Zone B.
純化方法
Reflux it with P2O5 for one day, then distil it through a helices-packed column. Also purified by gas chromatography. [Beilstein 2 IV 492.] LACHRYMATOR, HIGHLY TOXIC.
不和合性
Highly flammable, forms explosive mixture with air. Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides. Reacts with water and
steam, releasing toxic and corrosive vapors of hydrogen
chloride. Nitriles may polymerize in the presence of metals
and some metal compounds. They are incompatible with
acids; mixing nitriles with strong oxidizing acids can lead
to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and
epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both
aqueous acid and base to give carboxylic acids (or salts of
carboxylic acids). These reactions generate heat. Peroxides
convert nitriles to amides. Nitriles can react vigorously low aqueous solubility. They are also insoluble in aqueous
acids.
with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have
廃棄物の処理
Use a licensed professional
waste disposal service to dispose of this material. Dissolve
or mix the material with a combustible solvent and burn in
a chemical incinerator equipped with an afterburner and
scrubber. All federal, state, and local environmental regulations must be observed.
クロロアセトニトリル 上流と下流の製品情報
原材料
準備製品
2-(2,3-DIHYDRO-1BENZENESULFONYL-PYRROLO[2,3-B]PYRIDIN-3-YL)ETHANAMINE
2-(4-メチル-1-ピペリジニル)エタンアミン
2-PHENOXYETHANIMIDAMIDE HYDROCHLORIDE DIHYDRATE
2-クロロメチル-6-エチル-3H-チエノ[2,3-D]ピリミジン-4-オン
2-フェノキシエタンアミン
シアノメチレントリブチルホスホラン
フェントラミンメシル酸塩
4-メチル-1-ピペラジンエタンアミン
2-(Chloromethyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-one ,97%
1-(2-アミノエチル)ピペリジン
1-(2-アミノエチル)-4-ベンジルピペラジン
2-(2,3-DIHYDRO-1-BENZENESULFONYL-PYRROLO[2,3-B]PYRIDIN-3-YL)ACETONITRILE
1-〔2-(モルホリン-4-イル)エチル〕ピペラジン
2-フェノキシエタンイミドアミド塩酸塩二水和物
2-(クロロメチル)-5-メチルチエノ[2,3-D]ピリミジン-4(3H)-オン
4-クロロ-2-クロロメチルキナゾリン
1-PROPANESULPHONYLACETONITRILE
Acetonitrile, (2-benzothiazolylthio)- (8CI,9CI)
1,3-Benzenediol, 4-(2-chloro-1-iminoethyl)-