Methyl formate

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Methyl formate
IUPAC name

methyl methanoate

Other names

R-611

Identifiers
CAS number 107-31-3 YesY
PubChem 7865
ChemSpider 7577 YesY
ChEMBL CHEMBL295026 YesY
Jmol-3D images Image 1
Properties
Molecular formula C2H4O2
Molar mass 60.05 g mol−1
Appearance Colorless liquid
Density 0.98 g/cm³
Melting point −100 °C; −148 °F; 173 K
Boiling point 32 °C; 90 °F; 305 K
Hazards
MSDS Oxford MSDS
EU classification Highly flammable (F+); Harmful (Xn)
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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 odour, 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, practiced commercially by BASF among other companies gives 96% selectivity toward methyl formate, although it can suffer from catalyst sensitivity to water, which can 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. Foam Supplies, Inc. has trademarked Ecomate, which is used as a blowing agent for foam insulation, as a replacement for CFC, HCFC, or HFCs, with zero ozone depletion potential and <25 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

  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

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