Methyl formate
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2008-03-09T03:19:33Z
Benjah-bmm27
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3D [[ball-and-stick model]] added
{{Chembox new
| Name = '''Methyl formate'''
| ImageFileL1 = Methyl formate.png
| ImageSizeL1 = 100px
| ImageNameL1 = Structural formula of methyl formate
| ImageFileR1 = Methyl-formate-3D-balls.png
| ImageSizeR1 = 100px
| ImageNameR1 = Ball-and-stick model of the methyl formate molecule
| IUPACName = Methyl formate
| Section1 = {{Chembox Identifiers
| CASNo = 107-31-3
| SMILES = O=COC
}}
| Section2 = {{Chembox Properties
| Formula = HCOOCH<sub>3</sub>
| MolarMass = 60.05 g/mol
| Density = 0.98 g/cm³
| MeltingPt = -100 °C
| BoilingPt = 32 °C
}}
}}
'''Methyl formate''', also called '''methyl methanoate''', is the methyl [[ester]] of [[formic acid]]. It is a clear liquid with an ethereal odor, high [[vapor pressure]] and low [[surface tension]].
==Production==
In the laboratory, methyl formate can be produced by the [[condensation reaction]] of [[methanol]] and formic acid, as follows:
:[[formic acid|HCOOH]] + [[methanol|CH<sub>3</sub>OH]] → HCOOCH<sub>3</sub> + [[water|H<sub>2</sub>O]]
Industrial methyl formate, however, is usually produced by the combination of [[methanol]] and [[carbon monoxide]] ([[carbonylation]]) in the presence of a strong base, such as [[sodium methoxide]]:<ref>Process Economics Reports, Review 88-1-1, Process Economics Program, SRI Consulting, California, 1999</ref>
:[[methanol|CH<sub>3</sub>OH]] + [[carbon monoxide|CO]] → HCOOCH<sub>3</sub>
This process, practised commercially by BASF amongst other companies gives 96 % selectivity towards methyl formate, although can suffer from [[catalyst]] sensitivity to water which can commonly be present in the [[carbon monoxide]] feedstock, commonly derived from [[synthesis gas]]. Very dry [[carbon monoxide]] is therefore an essential requirement.<ref>W. Couteau, J. Ramioulle, US Patent US4216339</ref>
==Uses==
Methyl formate is used primarily to manufacture [[formamide]], [[dimethylformamide]], and [[formic acid]]. Because of its high [[vapor pressure]], it is used for quick-drying finishes. It is also used as an [[insecticide]] and to manufacture certain [[pharmaceuticals]]. A historical use of methyl formate which sometimes brings it attention was in refrigeration. Before the introduction of less toxic refrigerants, methyl formate was used as an alternative to sulfur dioxide in domestic refrigerators, such as some models of the famous GE Monitor Top. Owners of methyl formate refrigerators should keep in mind that even though they operate below atmospheric pressure, if evidence of a leak develops, they should take measures to avoid exposure to the ether-smelling liquid and vapor.
==References==
{{unreferenced|date=November 2007}}
<references/>
==External links==
* [http://webbook.nist.gov/cgi/cbook.cgi?ID=107-31-3&Units=SI&cMS=on NIST Chemistry WebBook: Methyl formate]
* [http://www.chemicalland21.com/arokorhi/industrialchem/organic/METHYL%20FORMATE.htm ChemicalLand21.com entry on METHYL FORMATE]
[[Category:Formates]]
[[Category:Carboxylate esters]]
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