エチルアミン 化学特性,用途語,生産方法
外観
無色～ほとんど無色, 澄明の液体
性質
エチルアミンの製造方法として、ニトロエタンやの還元で得る方法や、とを反応させ、加水分解して得る方法などが挙げられます。また、工業的にはエチレンとアンモニアに適切な触媒を作用させる方法や、エタノールをアンモニアで置換する方法、アセトアルデヒドの還元的アミノ化などによっても合成することが可能です。
溶解性
水、エタノール及びアセトンと任意の割合で混和。
解説
エチルアミン，無色の液体．融点－80.6 ℃，沸点16.6 ℃．d15"0.689．Ka 5.2×10－4(25 ℃)．可燃性で，アンモニア様臭気をもち，水に易溶であるが水酸化ナトリウムで塩析される．アンモニアより強い塩基性をもち，塩酸，硫酸とC2H5NH2·HCl，(C2H5NH2)2·H2SO4などの塩をつくる．金属カリウムと反応して，カリウムエチルアミドC2H5NHKを生じる．染料，医薬品などの合成原料に用いられる．皮膚，粘膜を刺激する．LD50 400 mg/kg(ネズミ，経口)．森北出版「化学辞典（第2版）
用途
有機合成(和光試薬時報Vol.62 No.3,p.29(1994))。
用途
医薬品原料、染料中間体
用途
医薬品、染料中間体、ゴム薬品、農薬(除草剤)、界面活性剤、塗料
製造
ニトロエタン，C2H5NO2あるいはアセトニトリルCH3CNを還元するか，ヘキサメチレンテトラミンと臭化エチルの反応物を加水分解させると得られるエチルアミン．
使用上の注意
強いアミン臭があるのでドラフト内で取り扱う。腐食性が強いので保護眼鏡、保護手袋を着用する。
化学的特性
Ethylamine is a colorless gas or water-white
liquid (below 17℃). Strong, ammonia-like odor. Shipped
as a liquefied compressed gas.
物理的性質
Colorless liquid or gas with a strong ammonia-like odor. An experimentally determined odor
threshold concentration of 21 ppb
v was reported by Leonardos et al. (1969). Experimentally
determined detection and recognition odor threshold concentrations were 500 μg/m
3 (270 ppb
v)
and 1.5 mg/m
3 (810 ppb
v), respectively (Hellman and Small, 1974).
使用
Ethylamine is used in the manufacture ofdyes and resins, as a stabilizer for rubberlatex, and in organic synthesis.
定義
ethylamine: A colourless flammablevolatile liquid, C
2H
5NH
2; r.d. 0.69;m.p. –81°C; b.p. 16.6°C. It is a primaryamine made by reactingchloroethane with ammonia andused in making dyes.
一般的な説明
A colorless liquid or a gas (boiling point 62°F) with an odor of ammonia. Flash point less than 0°F. Density of liquid 5.7 lb / gal. Corrosive to the skin and eyes. Vapors are heavier than air. Produces toxic oxides of nitrogen during combustion. Exposure of the closed container to intense heat may cause Ethylamine to rupture violently and rocket.
空気と水の反応
Highly flammable. Water soluble.
反応プロフィール
Sensitive to heat. Reacts vigorously with oxidizing agents. Incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Incompatible with cellulose nitrate. Flammable gaseous hydrogen is generated in combination with strong reducing agents, such as hydrides. Also incompatible with oxidizing agents. A chemical base. Neutralizes acids to form salts plus water in an exothermic reaction Dissolves most paints, plastics and rubber .
危険性
Strong irritant. Flammable, dangerous fire
risk, flammable limits in air 3.5–14%.
健康ハザード
Ethylamine is a severe irritant to the eyes,skin, and respiratory system. The pure liquidor its highly concentrated solution can causecorneal damage upon contact with eyes. Skincontact can result in necrotic skin burns.
Rabbits exposed to 100 ppm ethylaminefor 7 h/day, 5 days/week for 6 weeks mani fested irritation of cornea and lung, and liverand kidney damage (ACGIH 1986). A 4-hourexposure to 3000 ppm was lethal to rats. Theacute oral and dermal toxicity of this com pound was moderate in test animals.
LD50 value, oral (rats): 400 mg/kg
LD50 value, skin (rabbits): 390 mg/kg.
使用用途
エチルアミンは、医薬品、染料、界面活性剤、塗料などのさまざまな物質の原料として、実験室スケールから工業用途にまで幅広く用いられています。常温では気体で存在することもあるので、水溶液の状態で使用されることが多いです。
1. バーチ還元
有機合成においては、出発原料としてはもちろんですが、特にバーチ還元 (ベンケサー還元) における1級アミンとしてよく用いられています。
2. 求核剤
また、アミンは非常に強い求核性を持つため、酸クロリドと反応させてアミドを合成したり、置換反応を利用して分子に窒素原子を導入する場合に使用できます。
3. 錯体
また、アミンは非共有電子対を持つので、多くの金属や電子不足な原子と配位することができます。
エチルアミンのその他情報
ジエチルアミンとトリエチルアミン
窒素原子にさらに多くのエチル基が結合したジエチルアミンやトリエチルアミンも、同様の使用用途を持ちますが、これらは常温で液体なので扱いが簡単でよく用いられています。
ジエチルアミンは除草剤に使用されているので、エチルアミン、ジエチルアミン、トリエチルアミンのうちで最も多くの量が使用されてきました。
参考文献
法規制情報
エチルアミンは、GHS分類において可燃性・引火性ガス、急性毒性、皮膚腐食性/刺激性、眼刺激性、特定標的臓器毒性 (単回・反復ばく露) に分類されます。皮膚や目に付着してしまった場合は、すぐに多量の水で洗い流さなければいけません。また、ゴム手袋や保護メガネをするなど、皮膚や目に付着しないように気を付ける必要があります。
エチルアミンの法規制は、名称等を表示・通知すべき危険物およびリスクアセスメントを実施すべき危険有害物、また消防法において第4類特殊引火物に指定されています。引火点が-17℃と非常に低いです。
化学性质
アンモニア臭を有する可燃性液体であり，水およびアルコールに易溶
化学反応性
Reactivity with Water No reaction; Reactivity with Common Materials: Will strip and dissolve paint; dissolves most plastic materials; can cause swelling of rubber by absorption. The reactions are not hazardous; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Flush with water; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
工業用途
Ethylamine has achieved widespread use as an intermediate in the manufacture of
a variety of products. It is used as a solvent for dyes, resins, and oils and as a
vulcanization accelerator for sulfur-cured rubbers as well as a stabilizer for rubber
latex (NIOSH 1981; HSDB 1989). The amine is used in the production of alkyl
isocyanates for intermediates in the manufacture of products such as pharmaceuticals
and resins. It also serves as an intermediate in the manufacture of triazine
herbicides, a corrosion inhibitor (1,3-diethyl thiourea), and an agent used in wash
and wear fabrics (dimethylolethyltriazone). Copious salts of ethylamine can also
be used in the refining of petroleum and vegetable oil (Sittig 1981). The amine also
has uses as an industrial solvent and as a chemical initiator in the preparation of
various solvents (HSDB 1989).
安全性プロファイル
A poison by ingestion,
skin contact, and intravenous routes.
Moderately toxic by inhalation. A severe eye
irritant. A very dangerous fire hazard when exposed to heat or flame. Moderate
explosion hazard when exposed to spark or
flame. Keep away from heat and open
flame, can react vigorously with oxidizing
materials. To fight fire, stop flow of gas, use
alcohol foam, dry chemical. Incompatible
with cellulose nitrate or oxidzers. When
heated to decomposition it emits toxic
fumes of NOx. See also MINES.
職業ばく露
Monoethylamine (MEA) is used as an
intermediate in the manufacture of the following chemicals:
triazine herbicides, 1,3-diethylthiourea (a corrosion inhibitor);
ethylamino-ethanol; 4-ethylmorpholine (urethane foam catalyst); ethyl isocyanate; and dimethylolethyltriazone (agent
used in wash-and-wear fabrics). The cuprous chloride salts of
MEA are used in the refining of petroleum and vegetable oil.
環境運命予測
Photolytic. The rate constant for the reaction of ethylamine and ozone in the atmosphere is 2.76
x 10
-20 cm
3/molecule?sec at 296 K (Atkinson and Carter, 1984). Atkinson (1985) reported a rate
constant of 6.54 x 10
-11 cm
3/molecule?sec for the vapor-phase reaction of ethylamine and OH
radicals at 25.5 °C. The half-life for this reaction is 8.6 h.
Low et al. (1991) reported that the photooxidation of aqueous primary amine solutions by UV
light in the presence of titanium dioxide resulted in the formation of ammonium and nitrate ions.
Chemical/Physical. Reacts with OH radicals possibly forming acetaldehyde or acetamide
(Atkinson et al., 1978). When ethylamine over kaolin is heated to 600 °C, hydrogen and
acetonitrile formed as the major products. Trace amounts of ethylene, ammonia, hydrogen
cyanide, and methane were also produced. At 900 °C, however, acetonitrile was not produced
(Hurd and Carnahan, 1930).
Reacts with mineral acids forming water-soluble salts (Morrison and Boyd, 1971).
代謝
Ethylamine is readily absorbed from the respiratory and gastrointestinal tracts.
When administered to humans as the HC1 form, about 32% of the ethylamine
could be recovered in the urine (Rechenberger 1984). It appears that ethylamine is
slowly oxidized by monoamine oxidase to form hydrogen peroxide and the
corresponding aldehyde. Subsequently, the peroxide is removed by catalase and
the aldehyde is likely converted to its carboxylic acid by aldehyde oxidase (Beard
andNoe 1981).
As with other alkylamines, a potential exists for in vivo nitrosation of ethylamine
from foods by the preservative sodium nitrite under the acidic conditions
found in the stomach (Lin et al 1983,1984).
貯蔵
Ethylamine should be stored in a flammable-liquids storage room or cabinet. It shouldbe stored away from oxidizing materials andsources of ignition. It is shipped in steelcylinders or drums.
輸送方法
UN1036, Ethylamine, Hazard Class: 2.1; Labels:
2.1-Flammable gas. Ethylamine, aqueous solution with not ,50% but not .70% ethylamine, Hazard Class: 3; Labels:
3-Flammable liquid, 8-Corrosive material. Cylinders must
be transported in a secure upright position, in a wellventilated truck. Protect cylinder and labels from physical
damage. The owner of the compressed gas cylinder is the
only entity allowed by federal law (49CFR) to transport
and refill them. It is a violation of transportation regulations to refill compressed gas cylinders without the express
written permission of the owner.
合成方法
アセトアルデヒドを原料とした還元アミノ化法で生産
純化方法
Condense it in an all-glass apparatus cooled by circulating ice-water, and store it with KOH pellets below 0o. [Beilstein 4 IV 307.]
不和合性
The aqueous solution is a strong base.
May form explosive mixture with air. Reacts violently
with strong acids; strong oxidizers; cellulose nitrate; and
organic compounds; causing fire and explosion hazard.
Also incompatible with organic anhydrides; isocyanates,
vinyl acetate; acrylates, substituted allyls; alkylene
oxides; epichlorohydrin, ketones, aldehydes, alcohols,
glycols, phenols, cresols, caprolactum solution. Attacksnonferrous metals: aluminum, copper, lead, tin, zinc, and
alloys; some plastics, rubber, and coatings.
廃棄物の処理
Return refillable compressed
gas cylinders to supplier. Controlled incineration; incinerator equipped with a scrubber or thermal unit to reduce
nitrogen oxides emissions
エチルアミン 上流と下流の製品情報
原材料
準備製品