Methyl formate
Names Preferred IUPAC name Systematic IUPAC name Other names Identifiers ChEBI ChEMBL ChemSpider ECHA InfoCard 100.003.166 EC Number UNII Properties C2H4O2 Molar mass 60.052 g·mol−1 Appearance Colorless liquid Odor pleasant,[1] ethereal Density 0.98 g/cm3 Melting point −100 °C (−148 °F; 173 K) Boiling point 32 °C (90 °F; 305 K) 30% (20°C)[1] Vapor pressure 634 hPa (476 mmHg) (20°C)[1] −32.0·10−6 cm3/mol Hazards Occupational safety and health (OHS/OSH): Can cause eye injury GHS labelling:[3] Danger H224, H302, H319, H332, H335 P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P330, P337+P313, P370+P378, P403+P233, P403+P235, P405, P501 NFPA 704 (fire diamond) Flash point −19 °C; −2 °F; 254 K[1] Explosive limits 4.5%-23%[1] Lethal dose or concentration (LD, LC): 1622 mg/kg (oral, rabbit)[2] 50,000 ppm (guinea pig, 20 min)[2] NIOSH (US health exposure limits): TWA 100 ppm (250 mg/m3)[1] TWA 100 ppm (250 mg/m3) ST 150 ppm (375 mg/m3)[1] 4500 ppm[1] Safety data sheet (SDS) Oxford MSDS
Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. It has the chemical formula HCOOCH3. The simplest example of a carboxylate ester, it is a colourless liquid with an ethereal odour, high vapor pressure, and low surface tension. It is a precursor to many other compounds of commercial interest.[4]
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:[4]
CH3OH + CO → CH3OCHO
This process, practiced commercially by BASF among other companies gives 96% selectivity toward methyl formate. The catalyst for this process is sensitive to water, which can be present in the carbon monoxide feedstock, which is commonly derived from synthesis gas. Very dry carbon monoxide is, therefore, essential.[5]
Methyl formate is used primarily to manufacture formamide, dimethylformamide, and formic acid. These compounds are precursors or building blocks for many useful derivatives.
Because of its high vapor pressure, it is used for quick-drying finishes and as a blowing agent for some polyurethane foam applications.[6] and as a replacement for CFCs, HCFCs, and HFCs. Methyl formate has near zero ozone depletion potential and zero global warming potential and a short atmospheric life of 3 days.[7]
It is also used as an insecticide.[8]
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.
- NIST Chemistry WebBook: Methyl formate
- ChemicalLand21.com entry on METHYL FORMATE
- CDC – NIOSH Pocket Guide to Chemical Hazards
