Methyl formate, also called methyl methanoate, is the methyl

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

of formic acid. The simplest example of a carboxylate ester, it is a colourless liquid with an ethereal odour, high

vapor pressure Vapor pressure or equilibrium vapor pressure is the pressure exerted by a vapor in thermodynamic equilibrium with its condensed phases (solid or liquid) at a given temperature in a closed system. The equilibrium vapor pressure is an indicat ...

, and low

surface tension Surface tension is the tendency of liquid surfaces at rest to shrink into the minimum surface area possible. Surface tension (physics), tension is what allows objects with a higher density than water such as razor blades and insects (e.g. Ge ...

. The gas form is odourless and toxic, and used to be used in fridges. It is a precursor to many other compounds of commercial interest.Werner Reutemann and Heinz Kieczka "Formic Acid" in ''Ullmann's Encyclopedia of Industrial Chemistry'' 2002, Wiley-VCH, Weinheim.

Production

In the laboratory, methyl formate can be produced by the condensation reaction of

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...

and formic acid, as follows: :HCOOH + CH₃OH → HCOOCH₃ + H₂O Industrial methyl formate, however, is usually produced by the combination of

and

carbon monoxide Carbon monoxide (chemical formula CO) is a poisonous, flammable gas that is colorless, odorless, tasteless, and slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the si ...

( carbonylation) in the presence of a strong base, such as sodium methoxide: Industrial synthesis of 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

feedstock, which is commonly derived from synthesis gas. Very dry

is, therefore, essential.

Uses

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

, 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 near zero ozone depletion potential and zero

global warming potential Global warming potential (GWP) is a measure of how much heat a greenhouse gas traps in the atmosphere over a specific time period, relative to carbon dioxide (). It is expressed as a multiple of warming caused by the same mass of carbon dioxide ( ...

and a short atmospheric life of 3 days. It is also used as an

insecticide Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. The major use of insecticides is in agriculture, but they are also used in home and garden settings, i ...

. 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 Sulfur dioxide (IUPAC-recommended spelling) or sulphur dioxide (traditional Commonwealth English) is the chemical compound with the formula . It is a colorless gas with a pungent smell that is responsible for the odor of burnt matches. It is r ...

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

References

External links

NIST Chemistry WebBook: Methyl formate

{{DEFAULTSORT:Methyl Formate Formate esters Methyl esters