アントラキノン
アントラキノン · モルキット · 9,10-アントラキノン · ホエライト · アントラセン-9,10-ジオン · アントラジオン · ヘライト · 9,10-アントラセンジオン
識別子と物理属性
| CAS No. | 84-65-1 |
|---|---|
| 分子式 | C14H8O2 |
| 平均分子量 | 208.21 g/mol |
| 単同位体質量 | 208.0524295 g/mol |
| SMILES | O=C1c2ccccc2C(=O)c2ccccc21 |
| InChIKey | RZVHIXYEVGDQDX-UHFFFAOYSA-N |
| PubChem CID | 6780 |
| ChEMBL | CHEMBL55659 |
| ChEBI | CHEBI:40448 |
| EC No. | 201-549-0 |
| DTXSID | DTXSID3020095 |
| 現地名 | アントラキノン |
化学・物理的性質
| XLogP | 3.4 |
|---|---|
| 極性表面積 | 34.1 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 0 |
| 重原子数 | 16 |
| 形式電荷 | 0 |
| 複雑度 | 261 |
| 物質分類 | Other Classes -> Aromatic KetonesDyeSemi-Volatile Organic Compound (SVOC) and(or) Waste-water effluent contaminant |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| 農薬 | RepellantsActive substance -> EU Pesticides database: Not approvedPesticide (Anthraquinone) -> USDA PDB |
| LogP（分配係数） | log Kow = 3.393.28 |
| 臭い | Aromatic odor (technical) |
| 密度 | 1.438 at 68 °F (NTP, 1992) - Denser than waterwill sink1.42-1.44 at 20 °C/4 °C1.4 g/cm³1.42-1.44 @ 20°C |
| Color/Form | Light yellow, slender monoclinic prisms by sublimation in vacuo. Almost colorless, orthorhombic, bipyramidal crystals from sulfuric acid and water.Yellow rhombic needles from alcohol, benzeneYellow-green crystals |
| 溶解度 | less than 1 mg/mL at 73 °F (NTP, 1992)0.44 g/100 g alc at 25 °C2.25 g/100 g boiling alc0.11 g/100 g ether at 25 °C0.61 g/100 g chloroform at 20 °C0.26 g/100 g benzene at 20 °C0.30 g/100 g toluene at 25 °CSOL IN CONCN SULFURIC ACIDSoluble in acetoneIn water, 1.353 mg/L at 25 °CSolubility in water: very poor0.00007g/l<0.1 g/100 mL で 23 ºC |
| 引火点 | 365 °F (NTP, 1992)185 °C365 °F (185 °C) (Closed cup)185 °C c.c. |
| 沸点 | 714 to 718 °F at 760 mmHg (NTP, 1992)377 °C at 760 mm Hg380 °C376.9 °C @760 [mm Hg]379-381 °C (lit.) |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| 融点 | 547 °F (sublimes) (NTP, 1992)286 °CLiquid Molar Volume = 0.193625 cu m/kmolIG Heat of Formation = -9.52X10+7 J/kmolHeat Fusion at Melting Point = 3.2552X10+7 J/kmol284-286 °C (lit.) |
| 蒸気密度 | 7.16 (vs air) |
| 蒸気圧 | 1 mm Hg ( 190 °C) |
| 屈折率 | 1.5681 (estimate) |
| 貯蔵条件 | no restrictions. |
| 外観・状態 | 粉 |
| 色 | 黄緑～カーキ～タン |
| Merck | 14,687 |
| BRN | 390030 |
| ヘンリー定数 | 4.2×102 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| 安定性 | 安定。強力な酸化剤とは相容れない。可燃性。 |
| 主な用途 | 食品および飲料医薬品 |
| InChI | 1S/C14H8O2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8H |
| InChIKey | RZVHIXYEVGDQDX-UHFFFAOYSA-N |
| SMILES | O=C1c2ccccc2C(=O)c3ccccc13 |
| LogP（分配係数） | 3.39-3.4 at 30℃ |
| CAS データベース | 84-65-1(CAS DataBase Reference) |
| NISTの化学物質情報 | 9,10-Anthraquinone(84-65-1) |
| EPAの化学物質情報 | Anthraquinone (84-65-1) |
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.
安全性と法規制
| GHS 分類 | DangerH350: May cause cancer [Danger Carcinogenicity]P203, P280, P318, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 4.1% (10 of 242) of reports.H317 (80.6%): May cause an allergic skin reaction [Warning Sensitization, Skin] |
|---|---|
| 規制情報 | Chemical: 9,10-AnthracenedioneHazard Traits - Carcinogenicity9,10-Anthracenedione is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 9,10-Anthracenedione are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Anthraquinone is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)2008/986Status: Active Update: 10-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/2211 |
| その他の安全情報 | IMAP assessments - 9,10-Anthracenedione: Human health tier II assessment |
| 火災危険 | This chemical is combustible. (NTP, 1992) |
| 火災の可能性 | Conbustible when exposed to heat or flame. |
| 健康有害性 | SYMPTOMS: Symptoms following exposure to this compound may include skin and eye irritation, allergic skin reaction and skin sensitization. It may cause discoloration of the urine. |
| 有害性の概要 | May cause skin irritation and sensitization[Merck Index] Toxic by ingestionFound in certain plants, e.g., Rhamnus berriesA skin irritant[HSDB] An irritant and possible skin sensitizer[CAMEO] An irritant[ICSC] No results for 84-65-1[EC/RN Number] AND dermatitis, allergic contact[mesh][PubMed] Allergic dermatitis reported[RTECS] Antraquuinone, insoluble in water and lipids, is biologically inert. [Ullmann] An irritant[MSDSonline] |
| 反応性グループ | Hydrocarbons, Aromatic |
| Special Reports |
用途
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
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.
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.
製法・合成法
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.
合成方法
アントラセンの空気酸化法とナフトキノン経由法の2種の製造方法がある。
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.]