Methyl propionate, also known as methyl propanoate, is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...
with the molecular formula CH
3CH
2CO
2CH
3. It is a colorless liquid with a fruity,
rum
Rum is a liquor made by fermenting and then distilling sugarcane molasses or sugarcane juice. The distillate, a clear liquid, is usually aged in oak barrels. Rum is produced in nearly every sugar-producing region of the world, such as the Ph ...
-like odor.
Preparation
Methyl propionate can be prepared by
esterification
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 ar ...
of
propionic acid
Propionic acid (, from the Greek words πρῶτος : ''prōtos'', meaning "first", and πίων : ''píōn'', meaning "fat"; also known as propanoic acid) is a naturally occurring carboxylic acid with chemical formula CH3CH2CO2H. It is a li ...
with
methanol
Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is ...
. Industrially, it is prepared by
carboalkoxylation, i.e., the reaction of
ethylene
Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds).
Ethylene ...
with
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 simpl ...
and methanol in the presence of a catalyst:
:C
2H
4 + CO + MeOH → MeO
2CCH
2CH
3
The reaction is catalyzed by
nickel carbonyl
Nickel carbonyl (IUPAC name: tetracarbonylnickel) is a nickel(0) organometallic compound with the formula Ni(CO)4. This colorless liquid is the principal carbonyl of nickel. It is an intermediate in the Mond process for producing very high-pu ...
and palladium(0) complexes.
[(mayth and yafs)][Scott D. Barnicki "Synthetic Organic Chemicals" in Handbook of Industrial Chemistry and Biotechnology edited by James A. Kent, New York : Springer, 2012. 12th ed.
.]
Uses
Condensation of Methyl propionate with formaldehyde followed by dehydration yields
methyl methacrylate
Methyl methacrylate (MMA) is an organic compound with the formula CH2=C(CH3)COOCH3. This colorless liquid, the methyl ester of methacrylic acid (MAA), is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA) ...
:
[
:MeO2CCH2CH3 + CH2O → MeO2CCH(CH2OH)CH3
:MeO2CCH(CH2OH)CH3 → MeO2CC(=CH2)CH3
Methyl propionate is used as a ]solvent
A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...
for cellulose nitrate
Nitrocellulose (also known as cellulose nitrate, flash paper, flash cotton, guncotton, pyroxylin and flash string, depending on form) is a highly flammable compound formed by nitrating cellulose through exposure to a mixture of nitric acid an ...
and lacquer
Lacquer is a type of hard and usually shiny coating or finish applied to materials such as wood or metal. It is most often made from resin extracted from trees and waxes and has been in use since antiquity.
Asian lacquerware, which may be c ...
s, and as a raw material for the production of paint
Paint is any pigmented liquid, liquefiable, or solid mastic composition that, after application to a substrate in a thin layer, converts to a solid film. It is most commonly used to protect, color, or provide texture. Paint can be made in many ...
s, varnish
Varnish is a clear transparent hard protective coating or film. It is not a stain. It usually has a yellowish shade from the manufacturing process and materials used, but it may also be pigmented as desired, and is sold commercially in variou ...
es and other chemicals such as methyl methacrylate
Methyl methacrylate (MMA) is an organic compound with the formula CH2=C(CH3)COOCH3. This colorless liquid, the methyl ester of methacrylic acid (MAA), is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA) ...
.[
Due to its fruity smell and taste, it is also used in fragrances and flavoring.]
References
{{Esters
Propionate esters
Methyl esters
Ester solvents
Sweet-smelling chemicals