o-トリジン 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
溶解性
水に難溶 (50mg/L水)。エタノール, エーテルに可溶。
解説
4,4′-diamino-3,3′-dimethylbiphenyl．C14H16N2(212.29)．o-トリジンは，o-ヒドラゾトルエンをベンジジン転位させてつくられる．結晶．融点129 ℃．エタノール，エーテルに可溶．染料，顔料の中間体．テトラゾ化して直接染料をつくるのに用いられ，また遊離塩素の比色定量試薬としての用途がある．森北出版「化学辞典（第2版）
用途
染料中間体
説明
o-Tolidine, also called orthotolidine or 2-tolidine, is a chemical compound with the molecular formula (C6H4(CH3)NH2)2. It is a white to reddish-colored, combustible, aromatic amine that emits toxic fumes of nitrogen oxides when heated to decomposition. Several isomers are known; the 3-tolidine derivative is also important commercially. It is a colorless compound although commercial samples are often colored. It is slightly soluble in water. It forms salts with acids, such as hydrochloride, which is commercially available. 2-Tolidine can be produced by a benzidine rearrangement from a hydrazine derivative derived from 2-nitrotoluene.
化学的特性
o-Tolidine is a white to reddish crystal or powder and has an aniline-like odor. It is soluble in alcohol, ether, and dilute acid, but only slightly soluble in water. It has a tendency to darken when exposed to air and is commonly utilized in paste or wet cake form. This compound serves as a fundamental component for the production of numerous dyes.
使用
o-Tolidine is used extensively in the manufacture of dyes, especially in the production of soluble azo dyes and insoluble pigments for the textile, leather, and paper sectors. Additionally, It is also used as a sensitive colorimetric reagent for the analysis of gold and free chlorine in water.
製造方法
There are two commonly used methods for producing o-Tolidine. The first method involves reducing ortho-nitrotoluene to 1,2-diorthotolylhydrazine, which is then rearranged with acid. The second method involves reducing o-nitrotoluene using zinc dust and caustic soda, then converting the resulting hydrazotoluene to o-Tolidine by boiling it with hydrochloric acid. Once either of these methods is completed, o-Tolidine can be extracted and purified through techniques such as solvent extraction and recrystallization.
一般的な説明
3,3'-dimethylbenzidine appears as white to reddish crystals or crystalline powder or a light tan powder. (NTP, 1992)
空気と水の反応
Insoluble in water.
反応プロフィール
C.I. 37230 is sensitive to exposure to light. May be sensitive to prolonged exposure to air. A weak base that forms salts with hydrochloric acid or sulfuric acid. C.I. 37230 can be acetylated. Incompatible with strong agents .
危険性
Eye, bladder and kidney irritant, bladder
cancer, and methemoglobinemia. Possible carcinogen.
健康ハザード
The information on toxicity and carcinogenicity of o-tolidine is very little. o-Tolidineoften contains other biphenylamine contaminants. Its structure and chemical propertiesare similar to those of benzidine. The toxicproperties are therefore expected to be similar to those of benzidine.
o-Tolidine is absorbed into body throughthe skin, respiratory, and gastrointestinaltract. The acute oral and dermal toxicity wasmoderate in experimental animals. An oralLD50 value in rats is within the range of400 mg/kg.
o-Tolidine produced bladder cancer in testspecies. Also, cancers in other tissues werenoted in some animals. ACGIH lists thissubstance as a suspected human carcinogen.
火災危険
Flash point data for C.I. 37230 are not available; however, C.I. 37230 is probably combustible.
安全性プロファイル
Confirmed carcinogen
with experimental carcinogenic and
tumorigenic data. Poison by intraperitoneal
route. Moderately toxic by ingestion.
Human mutation data reported. When
heated to decomposition it emits toxic
fumes of NOx.
職業ばく露
Over 75% of o-tolidine is used as a dye and as an intermediate in the production of rubber products, dyestuffs, pigments and pesticides. Approximately 20% of o-tolidine is used in the production of polyurethane-based high-strength elastomers, coatings, and rigid plastics. o-Tolidine has also been used in small quantities in chlorine test kits by water companies and swimming pool owners. Used as a laboratory agent to detect blood.
発がん性
3,3′-Dimethylbenzidine is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
輸送方法
UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.
純化方法
Dissolve the tolidine in *benzene by percolation through a column of activated alumina and crystallise it from *benzene/pet ether. [Beilstein 13 IV 410.]
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, strong reducing agents.
廃棄物の処理
Dissolve in flammable solvent and spray into firebox of an incinera tor equipped with afterburner and scrubber. 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.
o-トリジン 上流と下流の製品情報
原材料
準備製品
3-[[4'-[(6-アミノ-1-ヒドロキシ-3-スルホ-2-ナフチル)アゾ]-3,3'-ジメトキシ-1,1'-ビフェニル-4-イル]アゾ]-4-ヒドロキシ-1-ナフタレンスルホン酸二ナトリウム
ダイレクトスカイブルー
N,N'-ビス(アセトアセチル)-o-トルイジン
3-ヒドロキシキサントン
アシッドレッド114
5-アミノ-4-ヒドロキシ-3-[[4'-[(1-ヒドロキシ-4-スルホナフタレン-2-イル)アゾ]-3,3'-ジメチル[1,1'-ビフェニル]-4-イル]アゾ]-2,7-ナフタレンジスルホン酸トリナトリウム
N,N'-ビス(アセトアセチル)-o-トルイジン
1,3,6-Naphthalenetrisulfonic acid, 8-hydroxy-7-[[4'-[(2-hydroxy-1-naphthalenyl)azo]-3,3'-dimethyl[1,1'-biphenyl]-4-yl]azo]-, trisodium salt
3-アミノ-4-[[4'-[(1-アミノ-4-スルホ-2-ナフチル)アゾ]-3,3'-ジメチル-1,1'-ビフェニル-4-イル]アゾ]-2,7-ナフタレンジスルホン酸三ナトリウム
5-アミノ-3-[[4'-[(6-アミノ-1-ヒドロキシ-3-スルホナフタレン-2-イル)アゾ]-3,3'-ジメチル[1,1'-ビフェニル]-4-イル]アゾ]-4-ヒドロキシ-2,7-ナフタレンジスルホン酸トリナトリウム
Direct Black 24
DIRECT ORANGE 6
エバンスブルー
N,N'-(3,3'-ジメチル[1,1'-ビフェニル]-4,4'-ジイル)ビス(3-ヒドロキシ-2-ナフトアミド)
ダイレクト ブラック１５４
5-[[4'-[[2,6-ジアミノ-3-メチル-5-[(4-スルホフェニル)アゾ]フェニル]アゾ]-3,3'-ジメチル[1,1'-ビフェニル]-4-イル]アゾ]-2-ヒドロキシ安息香酸二ナトリウム
5-[[4'-[[4,5-ジヒドロ-3-メチル-5-オキソ-1-(4-スルホフェニル)-1H-ピラゾール-4-イル]アゾ]-3,3'-ジメチル-1,1'-ビフェニル-4-イル]アゾ]-2-ヒドロキシ安息香酸二ナトリウム
オキサミン ブルー 4R
Direct Brown 146
DIRECT YELLOW 2