Methyl acetate

Methyl acetate
Methyl acetate[1]
Identifiers
CAS number 79-20-9 YesY
PubChem 6584
ChemSpider 6335 YesY
UNII W684QT396F YesY
KEGG C17530 YesY
ChEMBL CHEMBL14079 YesY
Jmol-3D images Image 1
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
NFPA 704.svg
3
1
0
Flash point -9 °C
Related compounds
Related esters Methyl formate
Ethyl acetate
 YesY acetate (verify) (what is: YesY/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]

Contents

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]

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. 

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Look at other dictionaries:

  • methyl acetate — n. a colorless, volatile, flammable liquid, CH3CO2CH3, used as a solvent, paint remover, etc …   English World dictionary

  • methyl acetate — noun : a volatile flammable fragrant liquid ester CH3COOCH3 made from methanol and acetic acid and used chiefly as a solvent (as for nitrocellulose and cellulose acetate) * * * Chem. a colorless, flammable, volatile liquid, C3H6O2, the methyl… …   Useful english dictionary

  • methyl acetate — metilacetatas statusas T sritis chemija formulė CH₃COOCH₃ atitikmenys: angl. methyl acetate rus. метилацетат ryšiai: sinonimas – metiletanoatas …   Chemijos terminų aiškinamasis žodynas

  • methyl acetate — Chem. a colorless, flammable, volatile liquid, C3H6O2, the methyl ester of acetic acid, having a fragrant odor, used chiefly as a solvent. [1900 05] * * * …   Universalium

  • methyl acetate — noun The methyl ester of acetic acid …   Wiktionary

  • methyl acetate — meth′yl ac′etate n. chem. a colorless, flammable, volatile liquid, C3H6O2, the methyl ester of acetic acid used chiefly as a solvent • Etymology: 1900–05 …   From formal English to slang

  • methyl acetate — /mɛθəl ˈæsəteɪt/ (say methuhl asuhtayt) noun a colourless, combustible, volatile ester, CH3COOCH3, having a fragrant odour, used as a solvent; the methyl ester of acetic acid …  

  • methyl acetate — noun Date: 1885 a flammable fragrant liquid C3H6O2 used as a solvent and paint remover and in organic synthesis …   New Collegiate Dictionary

  • Acétate de méthyle — Général Nom IUPAC éthanoate de méthyle No CAS …   Wikipédia en Français

  • Acetate — For other uses, see Acetate (disambiguation). acetate anion …   Wikipedia

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