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Methyl formate

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Methyl formate Basic information
Methyl formate Chemical Properties
  • Melting point:-100 °C
  • Boiling point:32-34 °C(lit.)
  • Density 0.974 g/mL at 20 °C(lit.)
  • vapor density 2.1 (vs air)
  • vapor pressure 32.91 psi ( 55 °C)
  • refractive index n20/D 1.343(lit.)
  • Flash point:−16 °F
  • storage temp. Flammables area
  • solubility 300g/l
  • form Liquid
  • color Clear colorless
  • OdorPleasant; agreeable.
  • PH4-5 (200g/l, H2O, 20℃)
  • Odor Threshold130ppm
  • explosive limit5-23%(V)
  • Water Solubility 300 G/L (20 ºC)
  • λmaxλ: 259 nm Amax: 1.00
    λ: 260 nm Amax: 0.70
    λ: 265 nm Amax: 0.20
    λ: 270 nm Amax: 0.04
    λ: 310-400 nm Amax: 0.01
  • Merck 14,6077
  • BRN 1734623
  • Henry's Law Constant0.90 at 5.00 °C, 1.18 at 10.00 °C, 1.51 at 15.00 °C, 1.91 at 20.00 °C, 2.36 at 25.00 °C (column stripping-UV, Kutsuna et al., 2005)
  • Exposure limitsTLV-TWA 100 ppm (~250 mg/m3) (ACGIH, MSHA, and OSHA); TLV-STEL 150 ppm (~375 mg/m3) (ACGIH); IDLH 5000 ppm (NIOSH).
  • Stability:Stable. Extremely flammable. Readily forms explosive mixtures with air. Note low flash point and very wide explosion limits. Incompatible with oxidizing agents.
  • CAS DataBase Reference107-31-3(CAS DataBase Reference)
  • NIST Chemistry ReferenceMethyl formate(107-31-3)
  • EPA Substance Registry SystemMethyl formate (107-31-3)
Safety Information
  • Hazard Codes F+,Xn
  • Risk Statements 12-20/22-36/37
  • Safety Statements 9-16-24-26-33
  • RIDADR UN 1243 3/PG 1
  • WGK Germany 1
  • RTECS LQ8925000
  • Autoignition Temperature842 °F
  • TSCA Yes
  • HS Code 2915 13 00
  • HazardClass 3
  • PackingGroup I
  • Hazardous Substances Data107-31-3(Hazardous Substances Data)
  • ToxicityLD50 orally in Rabbit: 1500 mg/kg LD50 dermal Rat > 4000 mg/kg
MSDS
Methyl formate Usage And Synthesis
  • DescriptionMethyl formate is the methyl ester form of formic acid.It has a rather pleasant odor. It is an aromatic compound found in apples (Neubeller and Buchloh, 1986), and was identified as a volatile constituent in brewed, roasted, and dried coffee (Lovell et al., 1980); it has also been detected in the volatiles of chicken, beef, and pork flavor (Shahidi et al., 1986). Methyl formate is used primarily to manufacture formamide, dimethylformamide, and formic acid. It is also used as a solvent for quick-drying finishes such as lacquers and in organic synthesis. Other uses include use as a larvicide for tobacco and food crops, in the manufacture of certain pharmaceuticals, and as a blowing agent for foam insulation. It was formerly used as a refrigerant for house appliances.
  • Chemical PropertiesMethyl formate is a colorless liquid with a pleasant odor. Its solubility in water is 230 g/l at 25 °C (Riddick et al., 1985), but it reacts slowly with water to form formic acid and methyl alcohol (DOT, 1984). It is soluble in ether, chloroform, and is miscible with ethanol (Lide, 2000).
  • Chemical PropertiesMethyl 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.
  • Physical propertiesClear, colorless, mobile liquid with a pleasant, etheral odor. An odor threshold concentration of 130 ppmv was reported by Nagata and Takeuchi (1990).
  • UsesMethyl formate is used as a fumigant, as alarvicide for food crops, and as a solvent forcellulose acetate.
  • UsesMethyl formate is used primarily to manufacture formamide, dimethyl formamide, 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.
    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.
  • UsesFumigant and larvicide for tobacco and food crops. Fire hazard is avoided by use with CO2.
  • Production MethodsIn 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 :
    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.
  • General DescriptionA clear colorless liquid with an agreeable odor. Flash point -27°F. Less dense than water Vapors heavier than air.
  • Air & Water ReactionsHighly flammable. Water soluble. Reacts slowly with water to give formic acid, a corrosive material, and methanol, a flammable liquid. Both products are dissolved in the water.
  • Reactivity ProfileMethyl formate reacts with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated with caustic solutions. Flammable hydrogen is generated by mixing with alkali metals and hydrides.
  • HazardFlammable, dangerous fire and explosionrisk, explosive limits in air 5.9–20%. Eye, upperand lower respiratory tract irritant.
  • Health HazardMethyl formate is a moderately toxic com pound affecting eyes, respiratory tract, andcentral nervous system. It is an irritant tothe eyes, nose, and lungs. Exposure to highconcentrations of its vapors in air may pro duce visual disturbances, irritations, narcoticeffects, and respiratory distress in humans.Such effects may be manifested at a 1-hourexposure to about 10,000-ppm concentration.Cats died of pulmonary edema from 2-hourexposure to this concentration
    The acute oral toxicity of methyl formatewas low in test subjects. The symptoms werenarcosis, visual disturbances, and dyspnea.An oral LD50 value in rabbit is in the range1600 mg/kg..
  • Health HazardInhalation causes irritation of mucous membranes. Prolonged inhalation can produce narcosis and central nervous symptoms, including some temporary visual disturbance. Contact with liquid irritates eyes and may irritate skin if allowed to remain. Ingestion causes irritation of mouth and stomach and central nervous system depression, including visual disturbances.
  • Fire HazardBehavior in Fire: Vapor is heavier than air and may travel considerable distance to a source of ignition and flash back.
  • Chemical ReactivityReactivity with Water Slow reaction to form formic acid and methyl alcohol; reaction is not hazardous; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
  • Safety ProfileModerately toxic by ingestion. Inhalation of vapor can cause irritation to nasal passages and conjunctiva, optic neuritis, narcosis, retching, and death from pulmonary irritation. Industrial fatalities have occurred only with exposure to high concentrations. Flammable liquid. Very dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. Explosive in the form of vapor when exposed to heat or flame. Reacts with methanol + sodium methoxide to form an explosive product. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.
  • Potential ExposureMethyl formate is used as a solvent; as an intermediate in pharmaceutical manufacture; and as a fumigant
  • Environmental FatePhotolytic. Methyl formate, formed from the irradiation of dimethyl ether in the presence of chlorine, degraded to carbon dioxide, water, and small amounts of formic acid. Continued irradiation degraded formic acid to carbon dioxide, water, and hydrogen chloride (Kallos and Tou, 1977; Good et al., 1999).
    A rate constant of 2.27 x 10-12 cm3/molecule?sec was reported for the reaction of methyl formate and OH radicals in the atmosphere (Atkinson, 1989).
    Chemical/Physical. Hydrolyzes slowly in water forming methanol and formic acid (NIOSH, 1997). Hydrolysis half-lives reported at 25 °C: 0.91 h at pH 9, 9.1 h at pH 8, 2.19 d at pH 7, and 21.9 d at pH 6 (Mabey and Mill, 1978).
  • ShippingColor code—Red: Flammability Hazard: Store in a flammable liquid storage area or approved cabinet away from ignition sources and corrosive and reactive materials. Prior to working with this chemical, personnel should be trained on its proper handling and storage. Before entering confined space where this chemical may be present, check to make sure that an explosive concentration does not exist. Methyl formate must be stored to avoid contact with strong oxidizers, such as chlorine, bromine, chlorine dioxide; nitrates, and permanganates; since violent reactions occur. Store in tightly closed containers in a cool, well-ventilated area away from heat. Sources of ignition, such as smoking and open flames are prohibited where methyl formate is handled, used, or stored. Metal containers involving the transfer of 5 gal or more of methyl formate should be grounded and bonded. Drums must be equipped with selfclosing valves, pressure vacuum bungs; and flame arresters. Use only nonsparking tools and equipment, especially when opening and closing containers of methyl formate. Wherever methyl formate is used, handled, manufactured, or stored, use explosion-proof electrical equipment and fittings.
  • Purification MethodsWash the formate with strong aqueous Na2CO3, dry it with solid Na2CO3 and distil it from P2O5. (Procedure removes free alcohol or acid.) [Beilstein 2 IV 20.]
  • IncompatibilitiesMay form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Reacts slowly with water to form methanol and formic acid. Contact with water, steam releases formic acid. Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates isocyanates, mercaptans, nitrides, and sulfides (releasing heat, toxic, and possibly flammable gases), thiosulfates and dithionites (releasing hydrogen sulfate and oxides of sulfur)
  • Waste DisposalIncineration; atomizing in a suitable combustion chamber.
  • ReferencesLee, Jae S., J. C. Kim, and Y. G. Kim. "Methyl formate as a new building block in C1 chemistry." Applied Catalysis 57.1 (1990): 1-30.
    Handa, Yash Paul, et al. "Insulating Thermoplastic Foams Made With Methyl Formate-Based Blowing Agents." (2006).
Methyl formate Preparation Products And Raw materials
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