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Methyl formate

December 04, 2023

Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. The simplest example of a carboxylate ester, it is a colorless liquid with an ethereal odour, high vapor pressure, and low surface tension. It is a precursor to many other compounds of commercial interest.[4]

Methyl formate
Structural formula of methyl formate
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
  • 107-31-3 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:77699 Y
ChEMBL
  • ChEMBL295026 Y
ChemSpider
  • 7577 Y
ECHA InfoCard 100.003.166
EC Number
  • 209-282-1
  • 7865
UNII
  • 1MPH591FTG Y
  • DTXSID5025609
  • InChI=1S/C2H4O2/c1-4-2-3/h2H,1H3 Y
    Key: TZIHFWKZFHZASV-UHFFFAOYSA-N Y
  • InChI=1/C2H4O2/c1-4-2-3/h2H,1H3
    Key: TZIHFWKZFHZASV-UHFFFAOYAI
  • O=COC
Properties
C2H4O2
Molar mass 60.052 g·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]
-32.0·10−6 cm3/mol
Hazards
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)
Health 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 dose or 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 their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Production edit

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]

 
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. 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]

Uses edit

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 (for example Ecomate® manufactured by Foam Supplies Inc.) and as a replacement for CFCs, HCFCs, and HFCs. Methyl formate has zero ozone depletion potential and zero global warming potential[citation needed]. It is also used as an insecticide.

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.

References edit

  1. ^ a b c d e f g h NIOSH Pocket Guide to Chemical Hazards. "#0417". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b "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. Retrieved 19 December 2021.
  4. ^ a b Werner Reutemann and Heinz Kieczka "Formic Acid" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a12_013
  5. ^ W. Couteau, J. Ramioulle, US Patent US4216339

External links edit

  • NIST Chemistry WebBook: Methyl formate
  • ChemicalLand21.com entry on METHYL FORMATE
  • CDC - NIOSH Pocket Guide to Chemical Hazards

December 04, 2023
methyl, formate, also, called, methyl, methanoate, methyl, ester, formic, acid, simplest, example, carboxylate, ester, colorless, liquid, with, ethereal, odour, high, vapor, pressure, surface, tension, precursor, many, other, compounds, commercial, interest, s. Methyl formate also called methyl methanoate is the methyl ester of formic acid The simplest example of a carboxylate ester it is a colorless liquid with an ethereal odour high vapor pressure and low surface tension It is a precursor to many other compounds of commercial interest 4 Methyl formate Structural formula of methyl formate Ball and stick model of the methyl formate moleculeNamesPreferred IUPAC name Methyl formateSystematic IUPAC name Methyl methanoateOther names R 611IdentifiersCAS Number 107 31 3 Y3D model JSmol Interactive imageChEBI CHEBI 77699 YChEMBL ChEMBL295026 YChemSpider 7577 YECHA InfoCard 100 003 166EC Number 209 282 1PubChem CID 7865UNII 1MPH591FTG YCompTox Dashboard EPA DTXSID5025609InChI InChI 1S C2H4O2 c1 4 2 3 h2H 1H3 YKey TZIHFWKZFHZASV UHFFFAOYSA N YInChI 1 C2H4O2 c1 4 2 3 h2H 1H3Key TZIHFWKZFHZASV UHFFFAOYAISMILES O COCPropertiesChemical formula C 2H 4O 2Molar mass 60 052 g mol 1Appearance Colorless liquidOdor pleasant 1 Density 0 98 g cm3Melting point 100 C 148 F 173 K Boiling point 32 C 90 F 305 K Solubility in water 30 20 C 1 Vapor pressure 634 hPa 476 mmHg 20 C 1 Magnetic susceptibility x 32 0 10 6 cm3 molHazardsGHS labelling 3 PictogramsSignal word DangerHazard statements H224 H302 H319 H332 H335Precautionary statements 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 P501NFPA 704 fire diamond 240Flash point 19 C 2 F 254 K 1 Explosive limits 4 5 23 1 Lethal dose or concentration LD LC LD50 median dose 1622 mg kg oral rabbit 2 LCLo lowest published 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 MSDSExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Production 2 Uses 3 References 4 External linksProduction editIn the laboratory methyl formate can be produced by the condensation reaction of methanol and formic acid as follows HCOOH CH3OH HCOOCH3 H2OIndustrial 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 nbsp Base catalyzed carbonylation of methanol with carbon monoxide to methyl formateThis 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 Uses editMethyl 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 for example Ecomate manufactured by Foam Supplies Inc and as a replacement for CFCs HCFCs and HFCs Methyl formate has zero ozone depletion potential and zero global warming potential citation needed It is also used as an insecticide 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 References edit a b c d e f g h NIOSH Pocket Guide to Chemical Hazards 0417 National Institute for Occupational Safety and Health NIOSH a b Methyl formate Immediately Dangerous to Life or Health Concentrations IDLH National Institute for Occupational Safety and Health NIOSH Methyl formate pubchem ncbi nlm nih gov Retrieved 19 December 2021 a b Werner Reutemann and Heinz Kieczka Formic Acid in Ullmann s Encyclopedia of Industrial Chemistry 2002 Wiley VCH Weinheim doi 10 1002 14356007 a12 013 W Couteau J Ramioulle US Patent US4216339External links editNIST Chemistry WebBook Methyl formate ChemicalLand21 com entry on METHYL FORMATE CDC NIOSH Pocket Guide to Chemical Hazards Retrieved from https en wikipedia org w index php title Methyl formate amp oldid 1163392726, wikipedia, wiki, book, books, library,

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