Methyl formate, also called methyl methanoate, is the methyl

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...

formic acid Formic acid (), systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure . It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Est ...

. The simplest example of an ester, it is a colorless liquid with an ethereal odour, high

vapor pressure Vapor pressure (or vapour pressure in English-speaking countries other than the US; see spelling differences) or equilibrium vapor pressure is defined as the pressure exerted by a vapor in thermodynamic equilibrium with its condensed phase ...

, and low surface tension. 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 and

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

carbon monoxide Carbon monoxide ( chemical formula CO) is a colorless, poisonous, odorless, tasteless, flammable gas that is 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 Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry. The term carbo ...

) in the presence of a strong base, such as

sodium methoxide Sodium methoxide is the simplest sodium alkoxide. With the formula , it is a white solid, which is formed by the deprotonation of methanol. Itis a widely used reagent in industry and the laboratory. It is also a dangerously caustic base. ...

This process, practiced commercially by BASF among other companies gives 96% selectivity toward methyl formate. The

catalyst Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...

for this process is sensitive to water, which can be present in the

feedstock, which is commonly derived from

synthesis gas Syngas, or synthesis gas, is a mixture of hydrogen and carbon monoxide, in various ratios. The gas often contains some carbon dioxide and methane. It is principly used for producing ammonia or methanol. Syngas is combustible and can be use ...

. Very dry

is, therefore, essential.W. Couteau, J. Ramioulle, US Patent US4216339

Uses

Methyl formate is used primarily to manufacture formamide, dimethylformamide, and

. 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 and as a replacement for

CFC CFC, cfc, or Cfc may stand for: Science and technology * Chlorofluorocarbon, a class of chemical compounds * Cardiofaciocutaneous Syndrome, a rare and serious genetic disorder * Subpolar oceanic climate (''Cfc'' in the Köppen climate classific ...

s, HCFCs, and

HFC HFC may stand for: Chemicals * Hafnium carbide * Hydrofluorocarbons Financial institutions *HFC Bank, part of HSBC Finance *Home Finance Company, known in Ghana as "HFC Bank" Places *Hall for Cornwall, a theatre in Cornwall, UK *Heng Fa Chuen, a ...

s. Methyl formate has zero

ozone depletion potential The ozone depletion potential (ODP) of a chemical compound is the relative amount of degradation to the ozone layer it can cause, with trichlorofluoromethane (R-11 or CFC-11) being fixed at an ODP of 1.0. Chlorodifluoromethane (R-22), for examp ...

and zero

global warming potential Global warming potential (GWP) is the heat absorbed by any greenhouse gas in the atmosphere, as a multiple of the heat that would be absorbed by the same mass of carbon dioxide (). GWP is 1 for . For other gases it depends on the gas and the time ...

. 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

External links

NIST Chemistry WebBook: Methyl formate

{{DEFAULTSORT:Methyl Formate Formate esters Methyl esters