2,6-ジニトロトルエン 化学特性,用途語,生産方法
外観
白色～淡黄色、結晶～結晶性粉末
用途
有機合成試薬。
化学的特性
2,6-Dinitrotoluene is one of the six dinitrotoluene isomers. Dinitrotoluene (DNT) or Dinitro is an explosive with the formula C6H3(CH3)(NO2)2. At room temperature it is a pale yellow to orange crystalline solid. It is a high explosive and one of the precursors for trinitrotoluene (TNT), which is synthesized through three separate nitrations of toluene. The first product is mononitrotoluene, DNT is the second, and TNT is the third and final product.
物理的性質
Pale yellow, orange, brown or reddish rhombic crystals. Odor threshold concentration in water is
100 ppb (quoted, Keith and Walters, 1992).
使用
2,6-Dinitrotoluene is used primarily, along with the other
isomers, in producing toluene diisocyanate; production of the
diisocyanate ranges from 100 million to almost a billion
pounds each year.
定義
ChEBI: 2,6-dinitrotoluene is a dinitrotoluene carrying nitro substituents at positions 2 and 6. It has a role as a genotoxin.
製造方法
2,6-Dinitrotoluene is synthesized from o-nitrotoluene by nitration with mixed acid.
一般的な説明
Yellow to red solid or heated liquid with a slight odor. Solidifies in cool water. Solid and liquid sink in water.
空気と水の反応
Mixes slowly with water. Insoluble in water.
反応プロフィール
2,6-Dinitrotoluene is sensitive to heat. 2,6-Dinitrotoluene may explode when exposed to heat or flame. 2,6-Dinitrotoluene can be detonated only by a very strong initiator. 2,6-Dinitrotoluene is incompatible with strong oxidizers. 2,6-Dinitrotoluene is also incompatible with caustics and metals such as tin and zinc. 2,6-Dinitrotoluene may react with reducing agents. 2,6-Dinitrotoluene will attack some forms of plastics, rubber and coatings.
健康ハザード
INHALATION, INGESTION OR SKIN ABSORPTION: Headache, weakness, nausea or dizziness, cyanosis, drowsiness, shortness of breath and collapse. Can burn eyes and skin.
安全性プロファイル
Poison by ingestion. A
skin irritant. Questionable carcinogen with
experimental tumorigenic data. Mutation
data reported. When heated to
decomposition it emits toxic fumes of NOx.
See also 2,4-DINITROTOLUENE
環境運命予測
Biological. When 2,6-dinitrotoluene was statically incubated in the dark at 25 °C with yeast
extract and settled domestic wastewater inoculum, significant biodegradation with gradual
acclimation was followed by deadaptive process in subsequent subcultures. At a concentration of 5
mg/L, 82, 55, 47, and 29% losses were observed after 7, 14, 21, and 28-d incubation periods,
respectively. At a concentration of 10 mg/L, only 57, 49, 35, and 13% were observed after 7, 14,
21, and 28-d incubation periods, respectively (Tabak et al., 1981). Under anaerobic and aerobic
conditions, a sewage inoculum degraded 2,6-dinitrotoluene to aminonitrotoluene (Hallas and
Alexander, 1983).
Photolytic. Simmons and Zepp (1986) estimated the photolytic half-life of 2,6-dinitrotoluene in
surface water to range from 2 to 17 h.
Low et al. (1991) reported that the nitro-containing compounds (e.g., 2,4-dinitrophenol) undergo
degradation by UV light in the presence of titanium dioxide yielding ammonium, carbonate, and
nitrate ions. By analogy, 2,6-dinitrotoluene should degrade forming identical ions.
Chemical/Physical. 2,6-Dinitrotoluene will not hydrolyze (Kollig, 1993).
At influent concentrations of 1.0, 0.1, 0.01, and 0.001 mg/L, the GAC adsorption capacities
were 145, 70, 33, and 16 mg/g, respectively (Dobbs and Cohen, 1980).
代謝経路
2-Amino-6-nitrotoluene, 2,6-dinitrobenzyl alcohol, 2-
amino-6-nitrobenzyl alcohol, and the conjugates of the
latter two alcohols are detected in the urine of male
Wistar rats as metabolites of 2,6-dinitrotoluene (2,6-
DNT). In addition to the metabolites identified in the
urine, 2,6-dinitrobenzaldehyde is detected in the rat
bile. Incubation of 2,6-DNT with a hepatic microsomal
preparation gives 2,6-dinitrobenzyl alcohol. Incubation
of benzyl alcohol with a microsomal plus cytosol
preparation gives 2,6-dinitrobenzaldehyde, and
incubation of 2,6-dinitrobenzaldehyde with cytosol
preparations gives 2,6-dinitrobenzyl alcohol and 2,6-
dinitrobenzoic acid.
純化方法
Crystallise it from acetone. EXPLOSIVE when dry.[Beilstein 5 III 761, 5 IV 866.]
2,6-ジニトロトルエン 上流と下流の製品情報
原材料
準備製品