Methyl acetate

Not to be confused with menthyl acetate.

Methyl acetate[1]
IUPAC name Methyl acetate
Systematic name Methyl ethanoate
Identifiers
CAS number	79-20-9 Y
PubChem	6584
ChemSpider	6335 Y
UNII	W684QT396F Y
KEGG	C17530 Y
ChEMBL	CHEMBL14079 Y
Jmol-3D images	Image 1
SMILES O=C(OC)C
InChI InChI=1S/C3H6O2/c1-3(4)5-2/h1-2H3 Y Key: KXKVLQRXCPHEJC-UHFFFAOYSA-N Y InChI=1/C3H6O2/c1-3(4)5-2/h1-2H3 Key: KXKVLQRXCPHEJC-UHFFFAOYAV
Properties
Molecular formula	C3H6O2
Molar mass	74.08 g mol−1
Density	0.932 g cm−3
Melting point	-98 °C, 175 K, -144 °F
Boiling point	56.9 °C, 330 K, 134 °F
Refractive index (nD)	1.361
Hazards
MSDS	External MSDS
NFPA 704	3 1 0
Flash point	-9 °C
Related compounds
Related esters	Methyl formate Ethyl acetate
Y acetate (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH₃COOCH₃. It is normally a flammable liquid with a characteristic, pleasant smell like certain glues or nail polish removers. Methyl acetate has characteristics very similar to its analog ethyl acetate. Methyl acetate is used as a solvent, being weakly polar and lipophilic. Methyl acetate has a solubility 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 aqueous bases or acids. Methyl acetate is VOC exempt.^[2]

Preparation and reactions

Methyl acetate is produced industrially via the carbonylation of methanol as a byproduct of the production of acetic acid.^[3] Although not of commercial significance, methyl acetate arises by esterification in the presence of strong acids such as sulfuric acid.

Reactions

In the presence of strong bases such as sodium hydroxide or strong acids such as hydrochloric acid or sulfuric acid it is hydrolyzed 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 the ester. The reaction of methyl acetate and a base, for example sodium hydroxide, is a second-order reaction with respect to both reactants.

Applications

A major use of methyl acetate is as a volatile low toxicity solvent in glues, paints, and nail polish removers.

Acetic anhydride is produced by carbonylation of methyl acetate in a process that was inspired by the Monsanto acetic acid synthesis.^[4]

• Ethyl acetate

References

1. ^ Merck Index, 12th Edition, 6089.
2. ^ Zeno, W. Wicks, JR, Frank N. Jones, S. Peter Pappas, and Douglas A. Wicks. Organic Coatings Hoboken, New Jersey: Wiley, 2007. ISBN# 978-0-471-69806-7
3. ^ Hosea Cheung, Robin S. Tanke, G. Paul Torrence “Acetic Acid” in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a01_045
4. ^ Zoeller, J. R.; Agreda, V. H.; Cook, S. L.; Lafferty, N. L.; Polichnowski, S. W.; Pond, D. M. (1992). "Eastman Chemical Company Acetic Anhydride Process". Catalysis Today 13: 73–91. doi:10.1016/0920-5861(92)80188-S.