トルエン 化学特性,用途語,生産方法
外観
無色澄明の液体
定義
本品は、次の化学式で表される芳香族炭化水素である。
性質
化学式はC6H5CH3。芳香族炭化水素の一つ。メチルベンゼンとも。融点－94.99℃，沸点110.626℃，比重d420＝0.86694，屈折率nD20＝1.49693。引火点4.4℃(密閉)，7.2℃(開放)。ベンゼンによく似た芳香をもつ無色，引火性の液体で，空気中で燃えるとき芳香族化合物特有の黒いすす(煤)を出す。水に不溶，有機溶媒に可溶。トルエン, 代表的な芳香族炭化水素の一つ。トルオール、メチルベンゼンともいう。脂肪族と芳香族の性質をもつ化合物のなかで、もっとも簡単な構造である。1835年ごろに天然樹脂トルーバルサムtolu balsamの乾留物から発見されたのが名の由来。
石炭のガス軽油やタール軽油から得られる。石油化学工業では石油留分の接触リホーミングにより製造する。この方法では、メチルシクロヘキサン、1,2-ジメチルシクロペンタン、n-ヘプタンがトルエンに変化する。
溶解性
水に不溶 (0.05g/100ml水, 25℃), エタノール, エーテルに混和。水にほとんど不溶。アセトン、エタノール、エーテルと混和。
解説
methylbenzene．C7H8(92.13)．C6H5CH3．石油の改質油中に，またコールタール中に存在し，これらから分離，精製される．はじめにトルーバルサムを乾留して得られたのでこの名称がある．無色，可燃性のベンゼン臭をもつ液体．融点－95 ℃，沸点110.8 ℃．d200.867．n20D1.4969．λmax 262.5 nm(ε 270)．水に不溶，エタノール，エーテル，アセトンなどほとんどの有機溶剤とまざる．ベンゼンのメチル置換体であるが，メチル基の電子供与性のためにベンゼン核は親電子置換を受けやすい．2,4,6-トリニトロトルエンは爆薬TNTとして知られている．また，メチル基を酸化すれば安息香酸となり，塩素化すれば塩化ベンジル，塩化ベンジリデンを経てフェニルトリクロロメタンとなる．森北出版「化学辞典（第2版）
用途
紫外、可視及び蛍光スペクトル分析。
用途
食品等中の農薬及びPCB定量における溶媒。
用途
精密分析、超純度溶剤として個人専用試薬等。
用途
染料、香料、火薬(TNT)、有機顔料、合成クレゾール、甘味料、漂白剤、TDI、テレフタル酸、合成繊維、可塑剤などの合成原料、ベンゼン原料、キシレン原料、石油精製、医薬品、塗料?インキ溶剤等
用途
薄層クロマトグラフィー、ペーパークロマトグラフィーの展開溶媒。
用途
分解ガソリン等から抽出される芳香族炭化水素で、溶剤として使用される他、トルエンジイソシアネート、フェノール等の化学品の原料として使用されます。
溶剤、プラスチックス類原料、オクタン価基材
用途
液体クロマトグラフ分析用溶離液及び溶離液調製用。
用途
有機合成原料、溶剤。
用途
大気中等トルエンのGC分析標準液。
用途
トルエン，工業的には，染料，香料，医薬品，そのほかの合成原料となるほか，溶剤やガソリン配合燃料として多量に用いられる．酸化により安息香酸を生成する。適度な条件下ではベンズアルデヒドを得ることもできる。これらのトルエン誘導体は、染料、医薬、香料、爆薬などの製造に用いられる。トルエンを合成化学的用途の多いベンゼンやキシレンに変えるためには、不均化法や水素化脱メチル反応などが用いられる。また、トルエンそのものは溶剤やガソリン配合剤としての用途がある。トルエンの蒸気は中毒性があるので、吸入しないような注意が必要である。
化粧品の成分用途
溶剤、酸化防止剤
主な用途／役割
業務用の溶剤型接着剤、エマルション系接着剤に希に使用される。
使用上の注意
不活性ガス封入
説明
Toluene is a clear, colourless liquid with a sweet, benzene-like odour. Toluene occurs naturally
in crude oil and in the toluene tree. It is also produced in the process of making
gasoline and other fuels from crude oil and making coke from coal. Toluene is used in
making paints, paint thinners, fingernail polish, lacquers, adhesives, and rubber and in
some printing and leather tanning processes. Toluene is also used in the production of
polymers used to make nylon, plastic soda bottles, and polyurethanes and for pharmaceuticals,
dyes, cosmetic nail products, and the synthesis of organic chemicals.
Toluene has been reported as the most commonly abused hydrocarbon solvent, primarily
through ‘glue sniffing’. The common possibilities of exposure to high levels of toluene
include indoor air from the use of household products such as paints, paint thinners, adhesives,
synthetic fragrances, and many other sources.
化学的特性
Toluene is a clear, colorless, flammable liquid with a sweet/pungent odor. It is extensively used as a solvent in different industries, i.e., rubber chemical manufacturing, drugs and pharmaceuticals, thinner for inks, paints dyes, and perfume manufacturing. It is a natural constituent of crude oil and is produced from petroleum refi ning and coke-oven operations. Toluene occurs naturally as a component of crude oil and occurs in petroleum refi ning and coke oven operations. Occupational workers associated with several kinds of activities, such as manufacturing of dyes, printing inks, painting automobile mechanics, gasoline manufacturers, shippers, and retailers, adhesives and coatings manufacturers and applicators, audio-equipment product workers, chemical industry workers, coke-oven workers, fabric manufacturers (fabric coating), sites of hazardous wastes, linoleum manufacturers, in pharmaceutical manufacturing, printing works, shoe manufacturing industry, become exposed to toluene.
物理的性質
Colorless, clear, flammable liquid with a pleasant, sweet or paint-like odor similar to benzene. At
40 °C, the lowest concentration at which an odor was detected were 960 μg/L. Similarly at 25 °C,
the lowest concentration at which a taste was detected was 960 μg/L (Young et al., 1996).
Experimentally determined detection and recognition odor threshold concentrations were 600
μg/m
3 (160 ppb
v) and 7.0 mg/m
3 (1.9 ppm
v), respectively (Hellman and Small, 1974). Leonardos
et al. (1969) reported higher odor threshold concentrations for toluene derived from coke (4.68
ppmv) and petroleum (2.14 ppm
v). The average least detectable odor threshold concentrations in
water at 60 °C and in air at 40 °C were 24 and 140 μg/L, respectively (Alexander et al., 1982). An
odor threshold concentration of 330 ppb
v was determined by a triangular odor bag method (Nagata
and Takeuchi, 1990). Cometto-Mu?iz and Cain (1994) reported an average nasal pungency
threshold concentration of 29,574 ppm
v.
来歴
Toluene is a clear, flammable, aromatic hydrocarbon liquid with a smell similar to benzene.
It is also called methylbenzene, indicating that a methyl group has been added to one of
benzene’s carbon atoms. Toluene was first isolated by Pierre-Joseph Pelletier (1788–1842) and
Philippe Walter (1810–1847) in 1837. The name toluene comes from the South American
tree Toluifera balsamum. Henri-Etienne Sainte-Claire Deville (1818–1881) isolated toluene
from the tree’s gum, Tolu balsam, in 1841.
The main source of toluene is from the catalytic reforming of naphthas during petroleum
processing. During this process cycloalkanes are dehydrated, forming aromatics such as
toluene and xylene along with hydrogen. Toluene can also be obtained from the pyrolysis of
gasoline. It is a by-product when styrene is produced and can also be produced from coal tar,
which was its main source in the first half of the 20th century.
使用
Toluene is derived from coal tar as well aspetroleum. It occurs in gasoline and manypetroleum solvents. Toluene is used to producetrinitrotoluene (TNT), toluene diisocyanate,and benzene; as an ingredient fordyes, drugs, and detergents; and as an industrialsolvent for rubbers, paints, coatings, andoils.
調製方法
Benzene is produced from toluene through a process called hydrodealkylation. In thisprocess, toluene reacts with hydrogen in the presence of a chromium, platinum, or molybdenumcatalysts at temperatures of several hundred degrees Celsius and pressures of about50 atmospheres: C6H5CH3 + H2 → C6H6 + CH4. Toluene can also be used to producephenol, (C6H5OH), benzoic acid (C6H5COOH), and benzaldehyde (C6H5CHO). Nitratedforms of toluene produce explosive compounds; the most common of these is TNT (SeeTrinitrotoluene).
定義
ChEBI: The simplest member of the class toluenes consisting of a benzene core which bears a single methyl substituent.
製造方法
Toluene is the starting material for the production of tolylene diisocyanate
(TDI)，the process may be varied to give
products of differing isomer contents. The nitration of toluene (with a nitrating mixture containing 20% nitric acid, 60% sulphuric acid and 20%
water at 30-45°C) gives a mixture of 2-nitrotoluene (about 60%) and 4-
nitrotoluene (40%). If this mixture is nitrated further (with a mixture of 35%
nitric acid and 65% sulphuric acid at 65-80°C) without separation, the product is a mixture of2,4-dinitrotoluene (about 80%) and 2,6-dinitrotoluene
(20%). If, on the other hand, the mixed mononitrates are separated (by
distillation), then further nitration of the 2-nitrotoluene yields a mixture of
2,4-dinitrotoluene (about 65%) and 2,6-dinitrotoluene (35%) whilst further
nitration of the 4-nitrotoluene gives only 2,4-dinitrotoluene.
一般的な説明
A clear colorless liquid with a characteristic aromatic odor. Flash point 40°F. Less dense than water (7.2 lb / gal) and insoluble in water. Hence floats on water. Vapors heavier than air. May be toxic by inhalation, ingestion or skin contact. Used in aviation and automotive fuels, as a solvent, and to make other chemicals.
空気と水の反応
Highly flammable. Insoluble in water.
反応プロフィール
Toluene reacts vigorously with allyl chloride or other alkyl halides even at minus 70° C in the presence of ethyl aluminum dichloride or ethyl aluminum sesquichloride. Explosions have been reported [NFPA 491M 1991]. Incompatible with strong oxidizing agents. When added to a tank of sulfur dichloride, the tank over pressurized and ruptured in a reaction thought to be catalyzed by iron or iron(III) chloride [Chem. Eng. News, 1988, 66(32), 2].
危険性
Flammable, dangerous fire risk. Explosive
limits in air 1.27–7%. Toxic by ingestion,
inhalation, and skin absorption. Visual impairment,
female reproductive effects, and pregnancy loss.
Questionable carcinogen.
健康ハザード
Exposures to toluene cause adverse health effects to animals and humans. The symptoms of toxicity and poisoning include, but are not limited to, mild irritation to the skin, headache, nausea, and effects on the CNS. Prolonged exposure to high concentrations of toluene causes disturbances in vision, dizziness, nausea, CNS depression, paresthesia, and sudden collapse. The acute oral LD50 value of toluene in laboratory rats has been reported as 636–7300 mg/kg. Exposure to toluene has been reported to cause rapid and severe corneal damage and conjunctiva infl ammation. The acute dermal LD50 in rabbits was found to be between 1200 and 1400 mg/kg.
火災危険
Toluene is a flammable liquid (NFPA rating = 3), and its vapor can travel a considerable distance to an ignition source and "flash back." Toluene vapor forms explosive mixtures with air at concentrations of 1.4 to 6.7% (by volume). Hazardous gases produced in fire include carbon monoxide and carbon dioxide. Carbon dioxide and dry chemical extinguishers should be used to fight toluene fires.
燃焼性と爆発性
Toluene is a flammable liquid (NFPA rating = 3), and its vapor can travel a
considerable distance to an ignition source and "flash back." Toluene vapor forms
explosive mixtures with air at concentrations of 1.4 to 6.7% (by volume). Hazardous
gases produced in fire include carbon monoxide and carbon dioxide. Carbon dioxide
and dry chemical extinguishers should be used to fight toluene fires.
化学反応性
Reactivity with Water No reaction; Reactivity with Common Materials: No reactions; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
職業ばく露
Toluene is used as an industrial chemical, chemical intermediate; solvent, and emulsifier; may be encountered in the manufacture of benzene. It is also used as a chemical feed for toluene diisocyanate, phenol, benzyl and benzoyl derivatives; benzoic acid; toluene sulfonates; nitrotoluenes, vinyltoluene, and saccharin; as a solvent for paints and coatings; or as a component of automobile and aviation fuels.
発がん性
The IARC has determined that there is
evidence for the lack of carcinogenicity of
toluene in experimental animals and that there
is inadequate evidence for carcinogenicity in
humans. Results of in vitro assays generally
indicate that toluene is not genotoxic. Reports
of increased incidences of sister chromatid
exchanges and chromatid breaks in exposed
workers are confounded by concurrent exposure
to other organic chemicals.
貯蔵
toluene should be
used only in areas free of ignition sources, and quantities greater than 1 liter should
be stored in tightly sealed metal containers in areas separate from oxidizers.
輸送方法
UN1294 Toluene, Hazard Class: 3; Labels: 3-Flammable liquid.
不和合性
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. Violent reaction with mixtures of nitric and sulfuric acid.
廃棄物の処理
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.
トルエン 上流と下流の製品情報
原材料
準備製品
Chloroprene-phenolic adhesive 801
3,3a,4,5,6,6a-ヘキサヒドロシクロペンタ[c]ピロール-2(1H)-アミン・塩酸塩
QUINOLINE-2-CARBONYL CHLORIDE
イソシアン酸2-チエニル
フルオレセイン クロリド
酪酸(R)-グリシジル
1-(2-クロロベンジル)ピペラジン
5-ブロモピリジン-2-カルボニルクロリド, TECH GRADE
ジエチレングリコールモノヘキシルエーテル
Asphalt antifouling paint L40-32
4-オキソテトラヒドロチオフェン-3-カルボン酸メチル
(メトキシメチル)トリフェニルホスホニウムクロリド
1,2-ジアミノ-2-メチルプロパン
N-クロロメチルフタルイミド
トリス(4-ノニルフェノキシ)ホスフィン
ビス(ベンゾニトリル)パラジウム(ＩＩ)ジクロリド
1,3-ジメチル-2-(2-フリル)イミダゾリジン
1-ブチル-3-メチルイミダゾリウムブロミド
アンチモン(III)
1-(3-クロロベンジル)ピペラジン
3-チオフェンカルボン酸クロリド
2-AMINO-4-METHOXYPYRIMIDINE
3-イソシアナトベンゾニトリル
ジクロロ(1,5-シクロオクタジエン)パラジウム(II)
6-フルオロ-4-ヒドロキシ-2-(トリフルオロメチル)キノリン
4-アミノ-6-クロロ-5-ピリミジンカルボアルデヒド
トリメチルアミンN-オキシド (無水)
(11AS)-10,11,12,13-テトラヒドロ-N,N-ジメチル-ジインデノ[7,1-DE:1',7'-FG][1,3,2]ジオキサホスホシン-5-アミン
塩酸 フェニレフリン
N,O-ビス(トリメチルシリル)アセトアミド
5-メトキシピリジン-3-ボロン酸
4,6-ジメトキシ-2-ピリミジニルイソシアナート
ジシクロペンタジエニルクロミウム
1-(2,6-ジメチルフェニル)ピペラジン
5-ACETYLAMINO-2-CHLORO-4-PICOLINE
5-ブロモ-2,4-ジ-TERT-ブトキシピリミジン
2-ETHOXYPYRIMIDIN-4-YLAMINE
2,2-ジメチルシクロヘキサノン
1,3-イソシアン酸ベンゾジオキソール-5-イル
4-ヒドロキシ安息香酸 n-ヘプチル