ニトロメタン 化学特性,用途語,生産方法
外観
無色～わずかにうすい黄色, 澄明の液体
溶解性
水に可溶。エタノール, エーテルと混和。エタノール及びジエチルエーテルに極めて溶けやすく、水にやや溶けやすく、水溶液は酸性である。
解説
ニトロメタン，無色の液体．融点－29 ℃，沸点101.2 ℃，46.6 ℃(13.3 kPa)，27.5 ℃(5.3 kPa)．d254 1.1322．n22D 1.3806．水に難溶，エタノール，エーテル，ジメチルホルムアミドに可溶．水溶液は酸性を呈する．ニトロン酸としてアルカリ金属と塩をつくり，爆発性の固体となる．溶剤，ロケット燃料，界面活性剤，医薬品原料などに用いられる．有毒である．
用途
溶剤、界面活性剤、医薬中間体(原料)
用途
有機合成(和光試薬時報Vol.66 No.1,p.27(1998))。
製法
クロロ酢酸と亜硝酸ナトリウムとを加熱するか，ヨウ化メチルに亜硝酸銀を作用させると得られるニトロメタン．
使用上の注意
不活性ガス封入
説明
Nitromethane (75-52-5) is an explosive material that was
originally manufactured for various applications including
mining, construction, demolition, law enforcement, and
military uses. However, due to threats of terrorism and
increased attention to accident prevention, regulations concerning
the transportation, storage, use, and transfer relating to
explosives have steadily increased over the last few years and
manufacturing limited.
化学的特性
Nitromethane is a highly flammable and explosive colorless liquid with a strong, disagreeable odor. Nitromethane is not explosive, but is used as industrial chemical for various purposes. Nitromethane can explode only in big quantity and in strong confinement. In combination with some further components, nitromethane is the important part of very strong, cap sensitive explosives. Therefore, nitromethane is an easy accessible precursor for preparation of strong home-made explosives.
Nitromethane is used as a stabilizer of halogenated organic solvents, rocket and racing fuel and a chemical intermediate. It is also used as a solvent for cyanoacrylate adhesives, polymers and waxes. It serves as a Michael donor, adding to alfa,beta-unsaturated carbonyl compounds through 1,4-addition in the Michael reaction. It acts as a solvent used for extractions, reaction medium and as a cleaning solvent. Further, it is used in the manufacture of pharmaceuticals, explosives, fibers and coatings.
物理的性質
Colorless liquid with a strong, disagreeable odor. Odor threshold concentration is 3.5 ppm
(quoted, Amoore and Hautala, 1983).
使用
Most of the nitromethane produced in the United States (85% to 90%) is used in the synthesis of nitromethane derivatives used as pharmaceuticals, agricultural soil fumigants, and industrial antimicrobials (Markofsky 1991, Angus 2001). Nitromethane also is used as a fuel or fuel additive with methanol in racing cars, boats, and model engines. It formerly was used in the explosives industry as a component in a binary explosive formulation with ammonium nitrate and in shaped charges, and it was used as a chemical stabilizer to prevent decomposition of various halogenated hydrocarbons (NTP 1997, IARC 2000, Angus 2001).
調製方法
Nitromethane and the other important nitroparaffins are synthesized commercially
by the vapor-phase nitration of propane (Baker and Bollmeier 1978). At temperatures
of 370-450°C and pressures of 8-12 atmospheres, nitromethane, nitroethane
and 1- and 2-nitropropane are formed and then separated by distillation.
一般的な説明
A colorless oily liquid. Flash point 95°F. May violently decompose if intensely heated when contaminated. Denser than water and slightly soluble in water. Hence sinks in water. Vapors are heavier than air. Moderately toxic. Produces toxic oxides of nitrogen during combustion.
空気と水の反応
Highly flammable. Slightly soluble in water.
反応プロフィール
Nitromethane may explode if heated or strongly shocked, especially if mixed with acids, bases [Handling Chemicals Safely 1980. p.687], acetone, aluminum powder, ammonium salts in the presence of organic solvents, haloforms (chloroform, bromoform), or hydrazine in methanol. Ignites on contact with alkyl aluminum or alkyl zinc halides. Reacts violently with strong bases (potassium hydroxide, calcium hydroxide), amines (1,2-diaminoethane, hydrazine), bromine, carbon disulfide, hydrocarbons, formaldehyde, metal oxides, lithium aluminum hydride, sodium hydride, strong oxidizing agents (lithium perchlorate, nitric acid, calcium hypochlorite). Reacts with aqueous silver nitrate to form explosive silver fulminate [Bretherick, 5th ed., 1995, p. 183]. Mixtures of Nitromethane and aluminum chloride may explode when organic matter is present [Chem. Eng. News 26:2257. 1948]. Nitromethane, either alone or in a mixture with methanol and castor oil, has a delayed but violent reaction with powdered calcium hypochlorite [Haz. Home Chem 1963]. Nitromethane reacts violently with hexamethylbenzene [Lewis 2544]. Nitromethane is strongly sensitized by hydrazine [Forshey, D. RR. et al, Explosivestoffe, 1969, 17(6), 125-129].
危険性
Dangerous fire and explosion risk, lower
explosion limit 7.3% in air. Toxic by ingestion and
inhalation. Thyroid effects, upper respiratory tract
irritant, and lung damage. Possible carcinogen.
健康ハザード
Nitromethane is used primarily as a chemical intermediate in the synthesis of biocides, chemicals, and agricultural products and intermediates. It is slightly toxic to aquatic organisms, has a low bioconcentration potential, and is considered not readily biodegradable. Acute toxicity is low following oral or dermal exposure. Nitromethane is a mild eye irritant and is not likely to cause significant irritation to the skin. Long-term excessive exposure may cause central nervous system effects. Based on animal data, nitromethane is classified as a Category 2B carcinogen (potential human carcinogen).
火災危険
Behavior in Fire: Containers may explode
工業用途
Nitromethane is used as an intermediate in chemical syntheses, but more importantly
it is used as a solvent for coatings and inks. It and the other nitroparaffins are
excellent solvents for vinyls, epoxies, polyamides and acrylic polymers (Baker
and Bollmeier 1978). It also is used as a military propellant and a racing fuel
additive (HSDB 1988). Mixed with methanol and castor oil it is employed as a
model airplane fuel.
職業ばく露
Nitromethane is used in the production
of the fumigant, chloropicrin. It is best known as racing car
fuel. It is also used as a solvent and as an intermediate in
the pharmaceutical industry.
発がん性
Nitromethane is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.
環境運命予測
Chemical/Physical. Nitromethane will not hydrolyze because it does not contain a hydrolyzable
functional group.
代謝
Nitromethane is converted to nitrite and formaldehyde in a 1:1 ratio by hepatic
microsomes from phenobarbital-pretreated male Sprague-Dawley rats (Sakurai et
al 1980), but no formaldehyde could be detected when microsomes from the nose
or liver of untreated male Fischer-344 rats were incubated with nitromethane
(Dahl and Hadley 1983). Whether a similar conversion occurs in vivo has not been
determined, but the absence of nitromethane metabolism in microsomes from
untreated rats suggests that its metabolism in vivo may be slow.
輸送方法
UN1261 Nitromethane, Hazard Class: 3; Labels:
3-Flammable liquid.
不和合性
May explode from heat, shock, friction,
or concussion. Reacts with alkalis, strong acids; metallic
oxides. Detonates or reacts violently with strong oxidizers,
strong reducing agents such as hydrides; formaldehyde,
copper, copper alloys; lead, lead alloys; hydrocarbons and
other combustibles, causing fire and explosion hazard.
Forms shock sensitive mixture when contaminated with
acids, amines, bases, metal oxides; hydrocarbons, and other
combustible materials.
廃棄物の処理
Incineration: large quantities
of material may require nitrogen oxide removal by catalytic
or scrubbing processes.
ニトロメタン 上流と下流の製品情報
原材料
準備製品
TRANS-2-(2-ニトロビニル)チオフェン
polythiniren
2,6-ジメチルベンズアルデヒド
3-メトキシイソニコチン酸
ベルベリン
2,6-DICHLOROPHENETHYLISOCYANIDE
7-ヒドロキシ-6-メトキシ-3,4-ジヒドロイソキノリン
チアネプチン
[(E)-2-ニトロビニル]ベンゼン
6-フルオロトリプタミン塩酸塩
シアノメチレントリブチルホスホラン
3-ヒドロキシ-4-メトキシフェネチルアミン塩酸塩
2-(3-メトキシ-4-ヒドロキシフェニル)エチルアミン
1-(ニトロメチル)シクロヘキサノール
4'-(トリフルオロメトキシ)アセトフェノン
2,3-ジメトキシフェネチルアミン
1-ニトロプロパン
2-ニトロプロパン
1-アミノメチル-1-シクロヘキサノール塩酸塩
3-ニトロベンゾ[B]フラン-5-オール
7-メチルイソキノリン
4,5,6,7-テトラヒドロチエノ[3,2-c]ピリジン·塩酸塩
2-メトキシ-4-(2-ニトロエテニル)フェノール
フェノルドパム
1,1'-ジメチル-4,4'-ビピリジニウム
チクロピジン
2-(2,4-ジメトキシフェニル)エタンアミン
2-(3H-Imidazol-4-yl)-ethylamine
2-(ヒドロキシメチル)-2-ニトロ-1,3-プロパンジオール
マロチラート
2-(2-フルオロフェニル)エチルアミン
トリス(ヒドロキシメチル)アミノメタン
ブロノポール
1-メチルアミノ-1-メチルチオ-2-ニトロエチレン
3,4-ジヒドロキシフェニルエチルアミン
DL-3-アミノ-2-ヒドロキシプロピオン酸
7-(ブロモメチル)イソキノリン
シクロヘプタノン
4-アミノ-3-(5-クロロチオフェン-2-イル)ブタン酸
1-(アミノメチル)-1-シクロヘキサノール