2,4,6-トリクロロフェノール 化学特性,用途語,生産方法
外観
白色～赤褐色, 結晶～結晶性粉末又は塊
溶解性
水に不溶, 各種有機溶剤に可溶。
解説
2,4,6-トリクロロフェノール，針状晶．融点69.5 ℃，沸点246 ℃．d7041.4901．pKa 7.42(25 ℃)．ベンゼン，アセトン，メタノールに易溶，水に難溶．殺菌剤，防腐剤に用いられる．
森北出版「化学辞典（第2版）
用途
有機合成用原料(染料中間物)、殺菌剤、木材防腐剤。
用途
殺菌剤、殺虫剤中間体
製造
2,4,6-トリクロロフェノール，加熱しながら，フェノールに乾燥塩素ガスを吹き込み，生成物を分留すると得られる．
毒性
眼，皮膚を刺激する．LD50 2650 mg/kg(ラット，経口)．
化学的特性
Yellow flakes; strong phenolic odor. Soluble in
acetone, alcohol, and ether; insoluble in water. Nonflammable.
物理的性質
Colorless needles or yellow solid with a strong, phenolic, musty or rotten vegetable-type odor. At
40 °C, the lowest concentration at which an odor was detected was 380 μg/L. At 25 °C, the lowest
concentration at which a taste was detected was >12 μg/L (Young et al., 1996).
使用
2,4,6-Trichlorophenol is used as a broad range pesticide against insects, fungi, vegetation and bacteria. It has become a common environmental contaminant and probable human carcinogen.
定義
ChEBI: A trichlorophenol with phenolic substituents on positions 2, 4 and 6.
空気と水の反応
Insoluble in water.
反応プロフィール
2,4,6-Trichlorophenol is incompatible with acid chlorides, acid anhydrides and oxidizing agents. 2,4,6-Trichlorophenol can be converted to the sodium salt by reaction with sodium carbonate. Forms ethers, esters and salts by reaction with metals and amines. Undergoes substitution reactions such as nitration, alkylation, acetylation and halogenation. Can be hydrolyzed by reaction with bases at elevated temperatures and pressures. Reacts with alkalis at high temperatures .
健康ハザード
In experimental animals, 2,4,6-
trichlorophenol causes toxic effects to the liver
and hematologic system and cancer. There is
no reliable information regarding exposure and
toxic effects in humans.
火災危険
Literature sources indicate that 2,4,6-Trichlorophenol is nonflammable.
安全性プロファイル
Confirmed carcinogen
with experimental carcinogenic data. Poison
by intraperitoneal route. Moderately toxic by
ingestion and skin contact. A skin and
severe eye irritant. Experimental
reproductive effects. Mutation data
reported. When heated to decomposition it
emits toxic fumes of Cl-. Used as a
germicide and preservative. See also
CHLOROPHENOLS.
発がん性
2,4,6-Trichlorophenol is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
環境運命予測
Biological. In activated sludge, only 0.3% mineralized to carbon dioxide after 5 d (Freitag et al.,
1985). In anaerobic sludge, 2,4,6-trichlorophenol degraded to 4-chlorophenol (Mikesell and Boyd,
1985). When 2,4,6-trichlorophenol was statically incubated in the dark at 25 °C with yeast extract
and settled domestic wastewater inoculum, significant biodegradation with rapid adaptation was
observed. At concentrations of 5 and 10 mg/L, 96 and 97% biodegradation, respectively, were
observed after 7 d (Tabak et al., 1981).
Photolytic. Titanium dioxide suspended in an aqueous solution and irradiated with UV light (λ
= 365 nm) converted 2,4,6-trinitrophenol to carbon dioxide at a significant rate (Matthews, 1986).
A carbon dioxide yield of 65.8% was achieved when 2,4,6-trichlorophenol adsorbed on silica gel
was irradiated with light (λ >290 nm) for 17 h (Freitag et al., 1985).
Chemical/Physical. An aqueous solution containing chloramine reacted with 2,4,6-trichlorophenol
to yield the following intermediate products after 2 h at 25 °C: 2,6-dichloro-1,4-
benzoquinone-4-(N-chloro)imine and 4,6-dichloro-1,2-benzoquinone-2-(N-chloro)imine (Maeda et
al., 1987).
純化方法
Crystallise the phenol from *benzene, EtOH or EtOH/water. [Beilstein 6 IV 1005.]
2,4,6-トリクロロフェノール 上流と下流の製品情報
原材料
準備製品
1-[N-プロピル-N-[2-(2,4,6-トリクロロフェノキシ)エチル]カルバモイル]-1H-イミダゾール
2-(2,4,6-Trichloro phenoxy)chloroethane
2,4,6-トリクロロ-4'-ニトロ-(1,1'-オキシビスベンゼン)
2,4-ジクロロフェノール
2-(2-ブロモエトキシ)-1,3,5-トリクロロベンゼン
2,4,6-トリクロロフェノキシ酢酸
2,3,4,6-テトラクロロフェノール (約10%ペンタクロロフェノール含む)
2,3,6-トリクロロフェノール
マロン酸ビス(2,4,6-トリクロロフェニル)
2,6-ジクロロ-1,4-ベンゾキノン
しゅう酸ビス(2,4,6-トリクロロフェニル)
2,6-ジクロロキノン-4-クロロイミド
ペンタクロロフェノール