Names | |||
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Preferred IUPAC name Methyl formate | |||
Systematic IUPAC name Methyl methanoate | |||
Other names R-611 | |||
Identifiers | |||
3D model (JSmol) | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.003.166 | ||
EC Number |
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PubChem CID | |||
UNII | |||
CompTox Dashboard (EPA) | |||
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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: [2] | |||
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): | |||
LD50 (median dose) | 1622 mg/kg (oral, rabbit) [3] | ||
LCLo (lowest published) | 50,000 ppm (guinea pig, 20 min) [3] | ||
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). |
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]
In the laboratory, methyl formate can be produced by the condensation reaction of methanol and formic acid, as follows:
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]
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 (for example Ecomate® manufactured by Foam Supplies Inc.) [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.[ citation needed ]
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.
Methanol is an organic chemical compound and the simplest aliphatic alcohol, with the chemical formula CH3OH. It is a light, volatile, colorless and flammable liquid with a distinctive alcoholic odor similar to that of ethanol, but is more acutely toxic than the latter. Methanol acquired the name wood alcohol because it was once produced chiefly by the destructive distillation of wood. Today, methanol is mainly produced industrially by hydrogenation of carbon monoxide.
Formic acid, systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure H−C(=O)−O−H. It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Esters, salts and the anion derived from formic acid are called formates. Industrially, formic acid is produced from methanol.
Butanone, also known as methyl ethyl ketone (MEK) or ethyl methyl ketone, is an organic compound with the formula CH3C(O)CH2CH3. This colorless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts. It is partially soluble in water, and is commonly used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran.
Bromomethane, commonly known as methyl bromide, is an organobromine compound with formula CH3Br. This colorless, odorless, nonflammable gas is produced both industrially and biologically. It is a recognized ozone-depleting chemical. It was used extensively as a pesticide until being phased out by most countries in the early 2000s. From a chemistry perspective, it is one of the halomethanes.
Bromotrifluoromethane, commonly referred to by the code numbers Halon 1301, R13B1, Halon 13B1 or BTM, is an organic halide with the chemical formula CBrF3. It is used for gaseous fire suppression as a far less toxic alternative to bromochloromethane.
Dichloromethane is an organochlorine compound with the formula CH2Cl2. This colorless, volatile liquid with a chloroform-like, sweet odor is widely used as a solvent. Although it is not miscible with water, it is slightly polar, and miscible with many organic solvents.
Chloromethane, also called methyl chloride, Refrigerant-40, R-40 or HCC 40, is an organic compound with the chemical formula CH3Cl. One of the haloalkanes, it is a colorless, sweet-smelling, flammable gas. Methyl chloride is a crucial reagent in industrial chemistry, although it is rarely present in consumer products, and was formerly utilized as a refrigerant. Most chloromethane is biogenic.
Acrylic acid (IUPAC: prop-2-enoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually.
Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is a flammable liquid with a characteristically pleasant smell reminiscent of some glues and nail polish removers. Methyl acetate is occasionally used as a solvent, being weakly polar and lipophilic, but its close relative ethyl acetate is a more common solvent being less toxic and less soluble in water. Methyl acetate has a solubility of 25% in water at room temperature. At elevated temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or aqueous acids. Methyl acetate is not considered a VOC in the USA.
Formamide is an amide derived from formic acid. It is a colorless liquid which is miscible with water and has an ammonia-like odor. It is chemical feedstock for the manufacture of sulfa drugs and other pharmaceuticals, herbicides and pesticides, and in the manufacture of hydrocyanic acid. It has been used as a softener for paper and fiber. It is a solvent for many ionic compounds. It has also been used as a solvent for resins and plasticizers. Some astrobiologists suggest that it may be an alternative to water as the main solvent in other forms of life.
Trichlorofluoromethane, also called freon-11, CFC-11, or R-11, is a chlorofluorocarbon (CFC). It is a colorless, faintly ethereal, and sweetish-smelling liquid that boils around room temperature. CFC-11 is a Class 1 ozone-depleting substance which damages Earth's protective stratospheric ozone layer. R-11 is not flammable at ambient temperature and pressure but it can become very combustible if heated and ignited by a strong ignition source.
Ethyl formate is an ester formed when ethanol reacts with formic acid. Ethyl formate has the characteristic smell of rum and is partially responsible for the flavor of raspberries, occurring naturally in some plant oils, fruits, and juices.
Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005.
Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.
Allyl alcohol is an organic compound with the structural formula CH2=CHCH2OH. Like many alcohols, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a precursor to many specialized compounds such as flame-resistant materials, drying oils, and plasticizers. Allyl alcohol is the smallest representative of the allylic alcohols.
Propylene glycol dinitrate (PGDN, 1,2-propylene glycol dinitrate, or 1,2-propanediol dinitrate) is an organic chemical, an ester of nitric acid and propylene glycol. It is structurally similar to nitroglycerin, except that it has one fewer nitrate group. It is a characteristically and unpleasantly smelling colorless liquid, which decomposes at 121 °C, below its boiling point. It is flammable and explosive. It is shock-sensitive and burns with a clean flame producing water vapor, carbon monoxide, and nitrogen gas.
2-Methoxyethanol, or methyl cellosolve, is an organic compound with formula C
3H
8O
2 that is used mainly as a solvent. It is a clear, colorless liquid with an ether-like odor. It is in a class of solvents known as glycol ethers which are notable for their ability to dissolve a variety of different types of chemical compounds and for their miscibility with water and other solvents. It can be formed by the nucleophilic attack of methanol on protonated ethylene oxide followed by proton transfer:
Bromochloromethane or methylene bromochloride and Halon 1011 is a mixed halomethane. It is a heavy low-viscosity liquid with refractive index 1.4808.
Dibromodifluoromethane is a mixed halomethane. It is a colorless non-flammable liquid. Along with Halons 1211, 2402, and 1301, it is one of the most effective fire extinguishers, however, it is also very toxic. It is a class I ozone depleting substance (ODS).
Methyl acrylate is an organic compound, more accurately the methyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced to make acrylate fiber, which is used to weave synthetic carpets. It is also a reagent in the synthesis of various pharmaceutical intermediates. Owing to the tendency of methyl acrylate to polymerize, samples typically contain an inhibitor such as hydroquinone.
ECOLOGICAL IMPACT Atmospheric life, days: 3 Kyoto compliant: yes Montreal compliant: yes Global warming potential: <1.5 Ozone depletion potential: 0