 | |
 | |
| Names | |
|---|---|
| Preferred IUPAC name Methyl acetate | |
| Systematic IUPAC name Methyl ethanoate | |
| Other names Methyl ester of acetic acid | |
| Identifiers | |
| |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
|
| ECHA InfoCard | 100.001.078 |
| KEGG |
|
| UNII | |
| |
| |
| Properties | |
| C3H6O2 | |
| Molar mass | 74.079 g·mol−1 |
| Appearance | Colorless liquid |
| Odor | Fragrant, fruity[2] |
| Density | 0.932 g cm−3 |
| Melting point | −98 °C (−144 °F; 175 K) |
| Boiling point | 56.9 °C (134.4 °F; 330.0 K) |
| ~25% (20 °C) | |
| Vapor pressure | 173 mmHg (20°C)[2] |
| -42.60·10−6 cm3/mol | |
Refractive index (nD) | 1.361 |
| Hazards | |
| NFPA 704 (fire diamond) | |
| Flash point | −10 °C; 14 °F; 263 K[2] |
| Explosive limits | 3.1%-16%[2] |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 3700 mg/kg (oral, rabbit)[3] |
LCLo (lowest published) | 11,039 ppm (mouse, 4 hr) 21,753 ppm (cat, 1 hr) 32,000 ppm (rat, 4 hr)[3] |
| NIOSH (US health exposure limits): | |
PEL (Permissible) | TWA 200 ppm (610 mg/m3)[2] |
REL (Recommended) | TWA 200 ppm (610 mg/m3) ST 250 ppm (760 mg/m3)[2] |
IDLH (Immediate danger) | 3100 ppm[2] |
| Safety data sheet (SDS) | External MSDS |
| Related compounds | |
Relatedesters | Methyl formate Ethyl acetate Ethyl formate Methyl fluoroacetate |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Methyl acetate, also known asMeOAc,acetic acid methyl ester ormethyl ethanoate, is a carboxylateester with the formula CH3COOCH3. It is a flammable liquid with a characteristically pleasant smell reminiscent of someglues and nail polish removers. Methyl acetate is occasionally used as asolvent, being weakly polar andlipophilic, but its close relativeethyl acetate is a more common solvent, being less toxic and less soluble in water. Methyl acetate has asolubility of 25% in water at room temperature. At elevated temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueousbases or aqueousacids. Methyl acetate is not regulated as avolatile organic compound in the USA.[4][5]
Methyl acetate is produced industrially via thecarbonylation ofmethanol as a byproduct of the production ofacetic acid.[6] Methyl acetate also arises byesterification of acetic acid with methanol in the presence of strong acids such assulfuric acid; this production process is famous[according to whom?] because ofEastman Kodak's intensified process using areactive distillation.
In the presence of strong bases such assodium hydroxide or strong acids such ashydrochloric acid or sulfuric acid it ishydrolyzed back into methanol and acetic acid, especially at elevated temperature. The conversion of methyl acetate back into its components, by an acid, is a first-order reaction with respect to theester. The reaction of methyl acetate and a base, for examplesodium hydroxide, is a second-order reaction with respect to both reactants.
Methyl acetate is a Lewis base that forms 1:1 adducts with a variety of Lewis acids. It is classified as ahard base and is a base in theECW model with EB =1.63 and CB = 0.95.
A major use of methyl acetate is as a volatile low toxicitysolvent in glues, paints, and nail polish removers.
Acetic anhydride is produced bycarbonylation of methyl acetate in a process that was inspired by theMonsanto acetic acid synthesis.[7]
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