無水酢酸
無水酢酸 (約1mol/Lジクロロメタン溶液) · 無水酢酸 [一般有機合成用] · 酢酸無水物 · アセチルアセタート · ビス酢酸無水物 · 酢酸アセチル · 二酢酸無水物 · 3-オキサペンタン-2,4-ジオン
識別子と物理属性
| CAS No. | 108-24-7 |
|---|---|
| 分子式 | C4H6O3 |
| 平均分子量 | 102.09 g/mol |
| 単同位体質量 | 102.03169405 g/mol |
| SMILES | CC(=O)OC(C)=O |
| InChIKey | WFDIJRYMOXRFFG-UHFFFAOYSA-N |
| PubChem CID | 7918 |
| ChEMBL | CHEMBL1305819 |
| ChEBI | CHEBI:36610 |
| EC No. | 203-564-8 |
| DTXSID | DTXSID0024395 |
| 現地名 | 無水酢酸 |
化学・物理的性質
| XLogP | -0.1 |
|---|---|
| 極性表面積 | 43.4 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 2 |
| 重原子数 | 7 |
| 形式電荷 | 0 |
| 複雑度 | 83.1 |
| 物質分類 | Other Classes -> Acid Anhydrides, OtherCorrosives |
| SpringerMaterials Properties | Schoenflies notation |
| LogP（分配係数） | -0.480-0.27 (calculated) |
| 臭い | Strong acetic odorStrong, pungent, vinegar-like odorとても強い刺激的な酢のような独特のにおい。 |
| 食品添加物 | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| 密度 | 1.08 (USCG, 1999) - Denser than waterwill sink1.082 g/cu cm at 20 °CRelative density (water = 1): 1.08 (20 °C)1.082 @ 20°C1.087 |
| Viscosity | 0.843 mPa.s at 25 °C |
| Color/Form | Colorless liquidVery refractive liquid |
| 溶解度 | Soluble in cold (greater than or equal to 10mg/ml)Decomposes in hot (NTP, 1992)In water, 120 g/L at 20 °CSlowly soluble in water, forming acetic acidWith alcohol forms ethyl acetatesoluble in chloroform, etherSoluble in ethanol, benzenemiscible with ethyl etherslightly soluble in carbon tetrachlorideMiscible with ethanol, ether, acetic acid, and ethyl acetateエーテル、クロロホルム、ベンゼンと混和します。反応する |
| Corrosivity | Corrosive |
| 引火点 | 121 °F (NTP, 1992)120 °F (49 °C) Closed cup49 °C c.c.130 °F |
| 沸点 | 283.19 °F at 760 mmHg (NTP, 1992)139.5 °C137.00 to 140.00 °C. @ 760.00 mm Hg139 °C282 °F139.8 °C @760 [mm Hg]140 °C |
| 融点 | -73.1 °C |
| 蒸気密度 | 3.5 (vs air) |
| 蒸気圧 | 10 mm Hg ( 36 °C) |
| 屈折率 | n20/D 1.390(lit.) |
| 貯蔵条件 | Store at RT. |
| 外観・状態 | 液体 |
| 色 | 無色 |
| 比重 | 1.082 |
| pH | 3 (10g/l, H2O, 20°C) |
| 爆発限界 | 2.0-10.2%(V) |
| においのタイプ | 酸性の |
| Merck | 14,56 |
| BRN | 385737 |
| ヘンリー定数 | 1.7×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| 誘電率 | 20.0 |
| 安定性 | 安定性 可燃性。強力な酸化剤、水、強塩基、アルコールとは相容れない。 |
| InChI | 1S/C4H6O3/c1-3(5)7-4(2)6/h1-2H3 |
| InChIKey | WFDIJRYMOXRFFG-UHFFFAOYSA-N |
| SMILES | CC(=O)OC(C)=O |
| LogP（分配係数） | -0.58 at 20℃ |
| 表面張力 | 32.65mN/m at 293.15K |
| CAS データベース | 108-24-7(CAS DataBase Reference) |
| NISTの化学物質情報 | Acetic acid anhydride(108-24-7) |
| EPAの化学物質情報 | Acetic anhydride (108-24-7) |
化学的特性
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolatable acid anhydride and is a widely used reagent in organic synthesis. It is a combustible, colorless, strongly refractive, liquid that smells strongly of acetic acid, formed by its reaction with the moisture in the air. Acetic anhydride is an esterification agent used in the preparation of modified starch and for acetylation of acetylated monoglycerides.
化学性质
アセチル化剤
安全性と法規制
| GHS 分類 | DangerH226: Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+P317, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)H226 (99.8%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P280, P284, P301+P317, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P319, P320, P321, P330, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement) |
|---|---|
| 規制情報 | Chemical: Acetic acid, anhydrideList II Chemical: A chemical, other than a List I chemical, specified by regulation that, in addition to legitimate uses, is used in manufacturing a controlled substance in violation of the Act. (21 eCFR 1310.02)Regulation (EC) No 178/2002 (amended)Acetic acid, 1,1'-anhydride is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acetic acid, 1,1'-anhydride 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)Status: Active Update: 08-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15314Acetic anhydride: Does not have an individual approval but may be used under an appropriate group standard |
| その他の安全情報 | IMAP assessments - Acetic acid, anhydride: Environment tier I assessment |
| 輸送ラベル（DOT） | Corrosive Flammable Liquid |
| 火災危険 | Special Hazards of Combustion Products: Irritating vapors are generated when heated.· EXCEPT FOR ACETIC ANHYDRIDE (UN1715), THAT IS FLAMMABLE, some of these materials may burn, but none ignite readily.Flammable. Many reactions may cause fire or explosion. See Chemical dangers Above 49 °C explosive vapour/air mixtures may be formed. |
| 火災の可能性 | A fire and exposion hazard when exposed to heat or flame. |
| 健康有害性 | Liquid is volatile and causes little irritation on uncovered skin. However, causes severe burns when clothing is wet with the chemical or if it enters gloves or shoes. Causes skin and eye burns and irritation of respiratory tract. Nausea and vomiting may develop after exposure. (USCG, 1999) |
用途
解説
無水酢酸，酢酸の酸無水物。化学式(CH3CO)2O。融点－68℃，沸点140.0℃の強烈な刺激臭をもつ無色の液体。クロロホルム，エーテルなどの有機溶媒に易溶。皮膚に触れると水ぶくれを生じる。水と徐々に反応して酢酸になるが，無機酸が存在すると急激に反応する。また無機塩基と激しく反応して酢酸塩となる。第三アミンの存在下にアルコールと反応して酢酸エステルを生じ，アンモニアまたはアミンと反応してアセトアミドを生じる(アセチル化)。
用途
酢酸エステル原料、染料等原料
用途
酢酸繊維素の製造、アスピリン、その他薬品、香料、染料、酢酸エステル類、有機合成原料
用途
アセチル化剤。コレステロールの定量。
用途
汎用分析用試薬。薬品、香料、染料等の有機合成原料。
説明
Acetic anhydride (chemical formula: (CH3CO)2O) is the simplest isolable anhydride of a carboxylic acid, is widely used as a reagent in organic synthesis. It has an internal asymmetric structure, leading to its potent electrophilicity. In organic chemistry, it is mainly used in acetylation for the manufacture of commercially significant materials, e.g. it can be used for the conversion of cellulose to cellulose acetate and aspirin. It can also be used as a wood preservative. In starch industry, it is a common acetylation compound for acetylation of monoglyceride. It is also an esterification agent for the production of modified starches. It is produced by carbonylation of methyl acetate or the reaction between ketene and acetic acid.
天然物の起源
Reported found in watercress (Nasturtium officinale r. br.).
使用
Acetic anhydride is an important solvent and acetylation agent. It is used for the manufacture of acetylcellulose, acetylsalicylic acid, acetanilide, nitrofurane, sulfonamides, vitamin B6 etc. As acetulizer and solvent in examining wool fat, glycerol, fatty and volatile oils, resins; detection of rosin. Widely used in organic syntheses, e.g., as dehydrating agent in nitrations, sulfonations and other reactions where removal of water is necessary.
用途
エーテルなどの有機溶媒に溶ける。アセチル化剤として広く使用され、セルロースをアセチル化してアセチルセルロースをつくるのに使われるほか、アスピリンなどの医薬、染料、クマリンなどの香料の合成に用いられる。特定麻薬向精神薬原料に指定されている。「氷酢酸」とよばれている水の含有量が低い高純度の酢酸とは別物である。
一般的な説明
A clear colorless liquid with a strong odor of vinegar. Flash point 129°F. Corrosive to metals and tissue. Density 9.0 lb /gal. Manufacture of cellulose esters, plastics, pharmaceuticals, photographic films, cigarette filters, and magnetic tape; inorganic synthesis as an acetylating agent, bleaching agent, and dehydrating agent.
製法・合成法
合成方法
ケテン法，カルボニル化法，アセトアルデヒド酸化法
純化方法
Adequate purification can usually be achieved by fractional distillation through an efficient column. Acetic acid can be removed by prior refluxing with CaC2 or with coarse Mg filings at 80-90o for 5days, or by distillation from a large excess of quinoline (1% AcOH in quinoline) at 75mm pressure. Acetic anhydride can also be dried by standing with Na wire for up to a week, removing the Na and distilling it under vacuum. (Na reacts vigorously with acetic anhydride at 65-70o). Dippy & Evans [J Org Chem 15 451 1950] let the anhydride (500g) stand over P2O5 (50g) for 3hours, then decanted it and stood it with ignited K2CO3 for a further 3hours. The supernatant liquid was distilled and the fraction b 136-138o was further dried with P2O5 for 12hours, followed by shaking with ignited K2CO3, before two further distillations through a five-section Young and Thomas fractionating column. The final material distilled at 137.8-138.0o. It can also be purified by azeotropic distillation with toluene: the azeotrope boils at 100.6o. After removal of the remaining toluene, the anhydride is distilled [sample had a specific conductivity of 5 x 10-9 ohm-1cm -1]. [Beilstein 2 H 96, 2 I 39, 2 II 91, 2 III 134, 2 IV 94.] Rapid procedure: Shake with P2O5, separate, shake with dry K2CO3 and fractionally distil.