Methyl formate

Methyl formate
IUPAC name	Methyl formate
Identifiers
CAS number	107-31-3 Y
PubChem	7865
SMILES	O=COC
Properties
Molecular formula	HCOOCH3
Molar mass	60.05 g/mol
Density	0.98 g/cm³
Melting point	-100 °C
Boiling point	32 °C
Hazards
MSDS	Oxford MSDS
EU classification	Highly flammable (F+); Harmful (Xn)
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. The simplest example of an ester, 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:

HCOOH + CH₃OH → HCOOCH₃ + H₂O

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:^[1]

CH₃OH + CO → HCOOCH₃

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.^[2]

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. Under the trademark Ecomate, it is now used a a blowing agent for foam insulation, as a replacement for CFC, HCFC, or HFCs, with zero ozone depletion potential and zero global warming potential ^[3].

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

This article does not cite any references or sources. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (November 2007)

1. ^ Process Economics Reports, Review 88-1-1, Process Economics Program, SRI Consulting, California, 1999
2. ^ W. Couteau, J. Ramioulle, US Patent US4216339
3. ^ United Nations Environment Program Rigid and Flexible Foams Technical Options Committee 2006 Assessment report. http://ozone.unep.org/teap/Reports/FTOC/ftoc_assessment_report06.pdf

External links

• NIST Chemistry WebBook: Methyl formate
• ChemicalLand21.com entry on METHYL FORMATE