アジリジン
アジラン · ジメチレンイミン · アミノエチレン · アジリジン · エチレンイミン · AZIRIDINE · ETHYLENIMINE · vinylamine
識別子と物理属性
| CAS No. | 151-56-4 |
|---|---|
| 分子式 | C2H5N |
| 平均分子量 | 43.07 g/mol |
| 単同位体質量 | 43.04219916 g/mol |
| SMILES | C1CN1 |
| InChIKey | NOWKCMXCCJGMRR-UHFFFAOYSA-N |
| PubChem CID | 9033 |
| ChEMBL | CHEMBL540990 |
| ChEBI | CHEBI:30969 |
| EC No. | 205-793-9 |
| DTXSID | DTXSID8020599 |
| 現地名 | アジリジン |
化学・物理的性質
| XLogP | -0.4 |
|---|---|
| 極性表面積 | 21.9 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 0 |
| 重原子数 | 3 |
| 形式電荷 | 0 |
| 複雑度 | 10.3 |
| 物質分類 | Hazardous Air Pollutants (HAPs)Toxic Gases & Vapors -> Other Toxic Gases & VaporsCarcinogens |
| 化粧品 | Viscosity controlling |
| pH | Strongly alkaline |
| SpringerMaterials Properties | 15N nuclear magnetic resonance spectrum |
| 農薬 | Pesticide -> EPA IRIS |
| LogP（分配係数） | -0.36 |
| 臭い | Pungent, ammonia-like odorAmine odor怪しいアンモニア性。 |
| 密度 | 0.8321 at 68 °F (EPA, 1998) - Less dense than waterwill float0.8321 at 24 °C/4 °CRelative density (water = 1): 0.80.832 @25 °C0,83 g/cm3 |
| Color/Form | Oily, water-white liquidColorless liquid ... [Note: Usually contains inhibitors to prevent polymerization]. |
| 溶解度 | Miscible (NIOSH, 2024)SOL IN ALKALISoluble in ethanolslightly soluble in ethervery soluble in chloroformmiscible in organic solventsIn water, 1X10+6 mg/L (miscible)Solubility in water: miscible水および事実上すべての有機溶媒と混和性 |
| Corrosivity | Corrosive |
| 引火点 | 12 °F (EPA, 1998)The Guide from the Emergency Response Guidebook is for "ethylenimine, inhibited." -11 °C12 °F (-11 °C) (Closed cup)-11 °C c.c.-11°C |
| 融点 | -78°C |
| 沸点 | 56°C |
| 蒸気圧 | 160 at 20 °C, 250 at 30 °C (quoted, Verschueren, 1983) |
| 屈折率 | nD25 1.412 |
| 外観・状態 | 無色の液体 |
| pKa（酸解離定数） | 8.01(at 25℃) |
| ヘンリー定数 | 1.33(x 10-7 atmm3/mol) at 25 °C (quoted, Mercer et al., 1990) |
| 誘電率 | 18.3(25℃) |
| 安定性 | とても燃えやすい。多種多様な物質と反応します。 |
| LogP（分配係数） | -2.68--0.28 at 25℃ |
| CAS データベース | 151-56-4(CAS DataBase Reference) |
| NISTの化学物質情報 | Ethylenimine(151-56-4) |
| EPAの化学物質情報 | Aziridine (151-56-4) |
化学的特性
Ethyleneimine is a colorless liquid with an ammonia-like smell or pungent odor. It is highly flammable and reacts with a wide variety of materials. Ethyleneimine is used in polymerization products, as a monomer for polyethyleneimin, and as a comonomer for polymers, e.g., with ethylenediamine. Polymerized ethylenimine is used in paper, textile chemicals, adhesive binders, petroleum, refi ning chemicals, fuels, lubricants, coating resins, varnishes, lacquers, agricultural chemicals, cosmetics, ion-exchange resins, photographic chemicals, colloid fl occulants, and surfactants. Ethyleneimine readily polymerizes, and it behaves like a secondary amine. Ethyleneimine is highly caustic, attacking materials such as cork, rubber, many plastics, metals, and glas except those without carbonate or borax. It polymerizes explosively on contact with silver, aluminum, or acid. The activity of ethyleneimine is similar to that of nitrogen and sulfur mustards. Ethyleneimine is used as an intermediate in the production of triethylenemelamine. Polymerized ethyleneimine is used in paper, textile chemicals, adhesive binders, petroleum, refi ning chemicals, fuels, lubricants, coating resins, varnishes, lacquers, agricultural chemicals, cosmetics, ion-exchange resins, photographic chemicals, colloid fl occulants, and surfactants
安全性と法規制
| GHS 分類 | DangerH225: Highly Flammable liquid and vapor [Danger Flammable liquids]P203, P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P318, P320, P321, P330, P361+P364, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]P203, P210, P233, P240, P241, P242, P243, P260, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P318, P320, P321, P330, P361+P364, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Hazards Identification | Toxic/poison by inhalation (TIH/PIH) |
| 規制情報 | Chemical: AziridineHazard Traits - CarcinogenicityGenotoxicityHematotoxicityNephrotoxicity and Other Toxicity to the Urinary SystemOcular ToxicityRespiratory ToxicityStatus: Active Update: 26-02-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/14422Ethylenimine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| その他の安全情報 | IMAP assessments - Aziridines: Human health tier II assessment |
| 輸送ラベル（DOT） | Poison Inhalation Hazard Flammable Liquid |
| 火災危険 | Irritating vapors are generated when heated. Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back. May polymerize in fires with evolution of heat and container rupture. Runoff to sewer may create fire or explosion hazard. Ethyleneimine vapors are not inhibited and may form polymers in vents or flame arresters, resulting in stopping of the vents. Toxic oxides of nitrogen are produced during combustion. Upon treatment with sodium hypochlorite, it gives off the explosive compound 1-chloroazidine. Avoid acids, sodium hypochlorite. If heated under pressure, instability may result. Hazardous polymerization may occur. Avoid contact with silver or aluminum. Explosive polymerization may occur upon contact with acids. Polymerization is catalyzed by carbon dioxide. (EPA, 1998) |
用途
解説
ethyleneimine．C2H5N(43.07)．エチレンイミンともいう．硫酸水素2-アミノエチルをアルカリと加熱するか，2-ハロエチルアミンにアルカリを作用させてつくる．工業的には，1,2-ジクロロエタンとアンモニアからもつくられる．アジリジン，アンモニア臭をもつ可燃性の液体．沸点56 ℃．d25250.833．n25D1.4123．水溶液にすると加水分解されやすい．第二級アミンとしての性質のほかに，不安定な三員環構造のために開環しやすく，チオール，フェノール，アミンなどと反応して2-アミノエチル誘導体を生じる．酸触媒で重合してポリアミンを生成する．繊維処理剤，接着剤，イオン交換樹脂の製造，エポキシ樹脂の硬化剤のほか，重合体は紙の湿潤強度を高めるのに用いられる．発がん性がある．LD50 15 mg/kg(ネズミ，経口)．森北出版「化学辞典（第2版）
用途
農薬?染料?繊維改質剤原料、有機合成原料
説明
Ethyleneimine is a colourless liquid with an ammonia-like smell or pungent odour. It is highly flammable and reacts with a wide variety of materials. Ethyleneimine is used in polymerisation products, as a monomer for polyethyleneimine and as a comonomer for polymers, for example, with ethylenediamine. Polymerised ethyleneimine is used in paper, textile chemicals, adhesive binders, petroleum, refining chemicals, fuels, lubricants, coating resins, varnishes, lacquers, agricultural chemicals, cosmetics, ion-exchange resins, photographic chemicals, colloid flocculants, and surfactants. Ethyleneimine readily polymerises, and it behaves like a secondary amine. Ethyleneimine is highly caustic, attacking materials such as cork, rubber, many plastics, metals, and glass except those without carbonate or borax. It polymerises explosively on contact with silver, aluminium, or acid. The activity of ethyleneimine is similar to that of nitrogen and sulphur mustards. Ethyleneimine is used as an intermediate in the production of triethylenemelamine.
使用
Ethyleneimine is used to manufacture triethylenemelamine and is used in its polymeric form in paper and textile chemicals, adhesive binders, petroleum-refining chemicals, fuels and lubricants, coating resins, varnishes, lacquers, agricultural chemicals, cosmetics, ion-exchange resins, photographic chemicals, colloid flocculants, and surfactants.
一般的な説明
A clear colorless liquid with an ammonia-like odor. Flash point 12°F. Less dense than water. Flammable over a wide range of vapor-air concentrations. Vapors irritate the skin, eyes, nose, and throat. May be toxic by prolonged inhalation, skin absorption, or ingestion. Carcinogenic. Vapors heavier than air. May polymerize exothermically if heated or contaminated. If the polymerization takes place inside a container, the container may rupture violently.
使用用途
アジリジンは、、繊維処理剤、の原料、農薬の原料、の製造などに用いられています。しかし、皮膚や粘膜へのアジリジンの暴露は、人体に非常に強い毒性を示します。有毒であるため、取り扱いには注意が必要です。 アジリジン基を持つアジリジン化合物は、ケミタイトとして販売されています。このケミタイトは、塗料、粘接着剤、コーティング剤の架橋剤に使用されています。
製法・合成法
調製方法
Industrial quantities are made with monoethanolamine via a two-step chemical dehydration process using sulphuric acid and sodium hydroxide, or by reacting 1,2-dichloroethane with ammonia. The U.S. production in 1978 was over 1500 metric tons (Ham 1978).
純化方法
Redistil it in an Ar or N2 atmosphere in a fume hood, and store it over KOH in sealed bottles in a refrigerator. Commercial aziridine has been dried over sodium and distilled from the metal through an efficient column before use [Jackson & Edwards J Am Chem Soc 83 355 1961, Wenker J Am Chem Soc 57 2328 1935]. It is a weaker base than Me2NH (pK2 5 10.87) but is caustic to the skin. It should not be inhaled, causes inflammation of the eyes, nose and throat, and one may become sensitized to it. It is soluble in H2O, has an ammoniacal smell and reacts with CO2. Pure aziridine is comparatively stable but polymerises in the presence of traces of H2O and is occasionally explosive in the presence of acids. CO2 is sufficiently acidic to cause polymerisation (forms linear polymers) which is not free radical promoted. It is stable in the presence of bases. The violet 2:1 Cu complex crystallises from EtOH containing a few drops of aziridine and adding Et2O, and has m 142o(dec). The picrate has m 142o. [O'Rourke et al. J Am Chem Soc 78 2159 1956.] It has also been dried over BaO and has been distilled from sodium under nitrogen. [Allen et al. Org Synth Coll Vol IV 433 1963, Beilstein 20 III/IV 1.] TOXIC.