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Methyl formate

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Methyl formate
Structural formula of methyl formate
Structural formula of methyl formate
Ball-and-stick model of the methyl formate molecule
Ball-and-stick model of the methyl formate molecule
Names
Preferred IUPAC name
Methyl formate
Systematic IUPAC name
Methyl methanoate
Other names
R-611
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.166Edit this at Wikidata
EC Number
  • 209-282-1
UNII
  • InChI=1S/C2H4O2/c1-4-2-3/h2H,1H3checkY
    Key: TZIHFWKZFHZASV-UHFFFAOYSA-NcheckY
  • InChI=1/C2H4O2/c1-4-2-3/h2H,1H3
    Key: TZIHFWKZFHZASV-UHFFFAOYAI
  • O=COC
Properties
C2H4O2
Molar mass 60.052g·mol−1
Appearance Colorless liquid
Odor pleasant[1]
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]
-32.0·10−6cm3/mol
Hazards
GHSlabelling:[3]
GHS02: FlammableGHS07: Exclamation mark
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)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
4
0
Flash point −19 °C; −2 °F; 254 K[1]
Explosive limits 4.5%-23%[1]
Lethal doseor concentration (LD, LC):
1622 mg/kg (oral, rabbit)[2]
50,000 ppm (guinea pig, 20 min)[2]
NIOSH(US health exposure limits):
PEL(Permissible)
 TWA 100 ppm (250 mg/m3)[1]
REL(Recommended)
 TWA 100 ppm (250 mg/m3) ST 150 ppm (375 mg/m3)[1]
IDLH(Immediate danger)
 4500 ppm[1]
Safety data sheet(SDS) Oxford MSDS
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).

Methyl formate,also calledmethyl methanoate,is the methylesterofformic acid.The simplest example of a carboxylate ester, it is a colorless liquid with an ethereal odour, highvapor pressure,and lowsurface tension.It is a precursor to many other compounds of commercial interest.[4]

Production[edit]

In the laboratory, methyl formate can be produced by thecondensation reactionofmethanolandformic acid,as follows:

HCOOH + CH3OH → HCOOCH3+ H2O

Industrial methyl formate, however, is usually produced by the combination ofmethanolandcarbon monoxide(carbonylation) in the presence of a strong base, such assodium methoxide:[4]

Base-catalyzed carbonylation of methanol with carbon monoxide to methyl formate
Base-catalyzed carbonylation of methanol with carbon monoxide to methyl formate

This process, practiced commercially by BASF among other companies gives 96% selectivity toward methyl formate. Thecatalystfor this process is sensitive to water, which can be present in thecarbon monoxidefeedstock, which is commonly derived fromsynthesis gas.Very drycarbon monoxideis, therefore, essential.[5]

Uses[edit]

Methyl formate is used primarily to manufactureformamide,dimethylformamide,andformic acid.These compounds are precursors or building blocks for many useful derivatives.

Because of its highvapor pressure,it is used for quick-drying finishes and as ablowing agentfor somepolyurethane foamapplications (for exampleEcomate®manufactured by Foam Supplies Inc.) and as a replacement forCFCs,HCFCs,andHFCs.Methyl formate has zeroozone depletion potentialand zeroglobal warming potential[citation needed].It is also used as aninsecticide.

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 tosulfur dioxidein domestic refrigerators, such as some models of the famous GE Monitor Top.

References[edit]

  1. ^abcdefghNIOSH Pocket Guide to Chemical Hazards."#0417".National Institute for Occupational Safety and Health(NIOSH).
  2. ^ab"Methyl formate".Immediately Dangerous to Life or Health Concentrations (IDLH).National Institute for Occupational Safety and Health(NIOSH).
  3. ^"Methyl formate".pubchem.ncbi.nlm.nih.gov.Retrieved19 December2021.
  4. ^abWerner Reutemann and Heinz Kieczka "Formic Acid" inUllmann's Encyclopedia of Industrial Chemistry2002, Wiley-VCH, Weinheim.doi:10.1002/14356007.a12_013
  5. ^W. Couteau, J. Ramioulle, US Patent US4216339

External links[edit]

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