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Methyl acetate

Not to be confused with Menthyl acetate.
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Methyl acetate[1]
Skeletal formula of methyl acetate
Ball-and-stick model of the methyl acetate molecule
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IUPAC name
Methyl acetate
Systematic IUPAC name
Methyl ethanoate
Other names
Methyl ester of acetic acid
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79-20-9 7pxY
ChEBI CHEBI:77700 7pxN
ChEMBL ChEMBL14079 7pxY
ChemSpider 6335 7pxY
Jmol-3D images Image
KEGG C17530 7pxY
PubChem Template:Chembox PubChem/format
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C3H6O2
Molar mass Lua error in Module:Math at line 495: attempt to index field 'ParserFunctions' (a nil value). g·mol−1
Appearance Colorless liquid
Odor Fragrant, fruity[2]
Density 0.932 g cm−3
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~25% (20 °C)
Vapor pressure 173 mmHg (20°C)[2]
1.361
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SDS External MSDS
NFPA 704

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3
1
Flash point Script error: No such module "convert". [2]
Explosive limits 3.1%-16%[2]
3700 mg/kg (oral, rabbit)[3]
US health exposure limits (NIOSH):

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Related esters
Methyl formate
Ethyl acetate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 a flammable liquid with a characteristically pleasant smell reminiscent of some glues and nail polish removers. Methyl acetate is occasionally used as a solvent, being weakly polar and lipophilic, but its close relative ethyl acetate is a more common solvent being less toxic and less soluble in water. 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 aqueous acids. Methyl acetate is not considered as a VOC.[4]

Preparation and reactions

Methyl acetate is produced industrially via the carbonylation of methanol as a byproduct of the production of acetic acid.[5] Methyl acetate also arises by esterification of acetic acid with methanol in the presence of strong acids such as sulfuric acid, this production process is famous because of Eastman Kodak's intensified process using a reactive distillation.

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.[6]

See also

References

  1. ^ Merck Index, 12th Edition, 6089.
  2. ^ a b c d e f g "NIOSH Pocket Guide to Chemical Hazards #0391". National Institute for Occupational Safety and Health (NIOSH). 
  3. ^ "Methyl acetate". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH). 
  4. ^ Zeno, W. Wicks, JR, Frank N. Jones, S. Peter Pappas, and Douglas A. Wicks (2007). Organic Coatings. Hoboken, New Jersey: Wiley. ISBN 978-0-471-69806-7. 
  5. ^ 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
  6. ^ 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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