アントラキノン

外観

うすい黄色～黄褐色, 結晶性粉末～粉末

溶解性

水に不溶。エタノールに可溶。熱ベンゼンに易溶。熱ベンゼン、熱トルエン、ニトロベンゼン、アニリンに溶けやすく、エタノールにもかなり溶ける。エーテルに溶けにくい。濃硫酸に溶ける。トルエンに溶ける。

解説

アントラキノン,淡黄色の結晶．融点286 ℃，沸点382 ℃．昇華性．ベンゼン，トルエンなどに熱時溶ける．還元すれば還元剤の種類によって，アントラヒドロキノン，アントロン，あるいはアントラセンを生じる．アントラキノンはいわゆるアントラキノン系染料の母体化合物で，キニザリン，アミノアントラキノン，ベンゾアントロンなど種々の誘導体を経て酸性染料，建染め染料が合成される．

森北出版「化学辞典（第2版）

用途

染料中間体

用途

アントラキノン系染料の出発原料、忌避剤、下剤の製造中間体、パルプ蒸解の添加剤、過酸化水素の製造の水素キャリアなど

製造

アントラキノン,広義では，アントラセンから誘導されるキノンをいい，1,2-，1,4-および9,10-アントラキノンの三つの異性体があるが，普通，9,10-アントラキノン(9,10-anthracenedione)をさす．アントラセンを酸化するか，無水フタル酸とベンゼンとのフリーデル-クラフツ縮合によって得られるo-ベンゾイル安息香酸を脱水閉環して製造される．

毒性

LD50 3500 mg/kg(ラット，腹腔内)．

化学的特性

Anthraquinone is a combustible, light yellow to green crystalline solid. Soluble in ethanol, ether and acetone, insoluble in water. It may be prepared by reacting benzene with phthalic anhydride. The compoundis the basis of a range ofdyestuffs.

天然物の起源

Anthraquinones naturally occur in some plants (eg. aloe, senna, rhubarb, and Cascara buckthorn), fungi, lichens, and insects, where they serve as a basic skeleton for their pigments. Natural anthraquinone derivatives tend to have laxative effects.

使用

Anthraquinone is used in paper industry as a catalyst to increase the pulp production yield and to improves the fiber strength through reduction reaction of cellulose to carboxylic acid. It is also used as a precursor for dye formation.

定義

ChEBI: Anthraquinone is an anthraquinone that is anthracene in which positions 9 and 10 have been oxidised to carbonyls. It is a colorless crystalline quinone used in producing dyestuffs such as alizarin.

製造方法

Anthraquinone is obtained by oxidation of anthracene using sodium dichromate plus sulfuric acid, and is purified by dissolving in concentrated sulfuric acid at 130 °C and pouring into boiling water, whereupon anthraquinone separates as pure solid, and is recovered by filtration. Further purification may be accomplished by sublimation or crystallization from nitrobenzene, aniline or tetrachloroethane.

一般的な説明

Anthraquinone is a polycyclic aromatic hydrocarbon derived from anthracene or phthalic anhydride. Anthraquinone is used in the manufacture of dyes, in the textile and pulp industries, and as a bird repellant.

空気と水の反応

Insoluble in water.

反応プロフィール

Anthraquinone is incompatible with strong oxidizing agents.

危険性

Possible carcinogen.

火災危険

Anthraquinone is combustible.

农业用途

Repellent, Seed treatment: Used as a seed dressing or protectant. Banned in EU.

製品名

(p)ANTHRAPEL®; FLIGHT CONTROL- PLUS®; HOELITE®; MORKIT®; REPELL®

薬理学

Anthraquinone is a secondary repellent and affects birds by causing post-ingestional distress (40). Sometimes, ingestion of anthraquinone-treated food produces vomiting, but often vomiting does not occur and the bird just sits quietly until the discomfort passes. Unlike methiocarb, anthraquinone doe not affect the bird’s nervous system and does not immobilize affected birds. Presumably, the emetic response is produced through irritation of the gut lining, but the actual mechanism is unclear. It is clear, however, that anthraquinone is not a taste repellent or contact irritant. Birds do not hesitate to eat treated food, and they exhibit no sign that treated food is unpalatable to them. The post-ingestional discomfort that results from eating anthraquinone-treated food produces a conditioned aversion to that food type. Birds need to experience the adverse consequences before learning to avoid the protected food. Thus, it is not reasonable to expect losses to cease immediately upon application of the repellent. There will be some level of loss in the crop as the depredating birds acquire the learned avoidance response.

安全性プロファイル

Moderately toxic by intraperitoneal route. A mild allergen. Mutation data reported. Combustible when exposed to heat or flame. To fight fire, use water, foam, CO2, water spray or mist, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

職業ばく露

Anthraquinone is an important starting material for vat dye manufacture. Also used in making organics; and used as a bird repellent in seeds.

輸送方法

UN3143 Dyes, solid, toxic, n.o.s. or Dye intermediates, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

純化方法

Crystallise anthraquinone from CHCl3 (38mL/g), *benzene, or boiling acetic acid, wash it with a little EtOH and dry it under vacuum over P2O5. [Beilstein 7 IV 2556.]

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

廃棄物の処理

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.