Methyl methacrylate is an
organic compoundAn organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered inorganic...
with the
formulaA chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....
CH
2=C(CH
3)COOCH
3. This colourless liquid, the methyl ester of
methacrylic acidMethacrylic acid, abbreviated MAA, is an organic compound. This colourless, viscous liquid is a carboxylic acid with an acrid unpleasant odor. It is soluble in warm water and miscible with most organic solvents. Methacrylic acid is produced industrially on a large scale as a precursor to its...
(MAA) is a
monomerA monomer is a small molecule that may become chemically bonded to other monomers to form a polymer...
produced on a large scale for the production of polymethyl methacrylate (PMMA).
The compound is manufactured by several methods, the principal one being the
acetone cyanohydrinAcetone cyanohydrin is an organic compound used in the production of methyl methacrylate, the monomer of the transparent plastic polymethyl methacrylate , also known as acrylic.-Preparation:...
(ACH) route, using
acetoneAcetone is the organic compound with the formula OC2. This colorless, mobile, flammable liquid is the simplest example of the ketones. Owing to the fact that acetone is miscible with water it serves as an important solvent in its own right, typically as the solvent of choice for...
and
hydrogen cyanideHydrogen cyanide is a chemical compound with chemical formula HCN. A solution of hydrogen cyanide in water is called hydrocyanic acid. Hydrogen cyanide is a colorless, extremely poisonous, and highly volatile liquid that boils slightly above room temperature at 26 °C...
as raw materials.
Methyl methacrylate is an
organic compoundAn organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered inorganic...
with the
formulaA chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....
CH
2=C(CH
3)COOCH
3. This colourless liquid, the methyl ester of
methacrylic acidMethacrylic acid, abbreviated MAA, is an organic compound. This colourless, viscous liquid is a carboxylic acid with an acrid unpleasant odor. It is soluble in warm water and miscible with most organic solvents. Methacrylic acid is produced industrially on a large scale as a precursor to its...
(MAA) is a
monomerA monomer is a small molecule that may become chemically bonded to other monomers to form a polymer...
produced on a large scale for the production of polymethyl methacrylate (PMMA).
Production
The compound is manufactured by several methods, the principal one being the
acetone cyanohydrinAcetone cyanohydrin is an organic compound used in the production of methyl methacrylate, the monomer of the transparent plastic polymethyl methacrylate , also known as acrylic.-Preparation:...
(ACH) route, using
acetoneAcetone is the organic compound with the formula OC2. This colorless, mobile, flammable liquid is the simplest example of the ketones. Owing to the fact that acetone is miscible with water it serves as an important solvent in its own right, typically as the solvent of choice for...
and
hydrogen cyanideHydrogen cyanide is a chemical compound with chemical formula HCN. A solution of hydrogen cyanide in water is called hydrocyanic acid. Hydrogen cyanide is a colorless, extremely poisonous, and highly volatile liquid that boils slightly above room temperature at 26 °C...
as raw materials. The intermediate cyanohydrin is converted with sulfuric acid to a sulfate ester of the methacrylamide, methanolysis of which gives
ammonium bisulfateAmmonium bisulfate, also known as ammonium hydrogen sulfate, is a white, crystalline solid when it is completely pure, with formula HSO4. It is commonly collected as a byproduct of flue gas desulfurization, formed by partial neutralization of sulfuric acid aerosols by gaseous ammonia,...
and MMA. Although widely used, the ACH route coproduces substantial amounts of
ammonium sulfateAmmonium sulfate , 2SO4, is an inorganic salt with a number of commercial uses. The most common use is as a soil fertilizer. It contains 21% nitrogen as ammonium cations, and 24% sulfur as sulfate anions...
. Some producers start with an
isobutyleneIsobutylene is a hydrocarbon of significant industrial importance. It is a four-carbon branched alkene , one of the four isomers of butylene. At standard temperature and pressure it is a colorless flammable gas.-Uses:...
or, equivalently,
tert-butanoltert-Butanol, or 2-methylpropan-2-ol , is the simplest tertiary alcohol. It is one of the four isomers of butanol. tert-Butanol is a clear liquid with a camphor-like odor. It is very soluble in water and miscible with ethanol and diethyl ether...
, which is sequentially oxidized first to
methacroleinMethacrolein, or methacrylaldehyde, is an unsaturated aldehyde. It is a clear, colorless, flammable liquid and is in cigarettes.Industrially, the primary use of methacrolein is in the manufacture of polymers and synthetic resins....
and then to methacrylic acid, which is then esterified with
methanolMethanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with formula CH3OH . It is toxic: drinking 10 ml will cause blindness, and as little as 100 ml will cause death...
. Propene can be
carbonylatedCarbonylation 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.-Organic chemistry:...
in the presence of acids to
isobutyric acidIsobutyric acid, also known as 2-methylpropanoic acid, is a carboxylic acid with structural formula 2-CH-COOH...
, which undergoes subsequent dehydrogenation. The combined technologies afford more than 3 billion kilograms per year. MMA can also be prepared from methyl propionate and
formaldehydeFormaldehyde is a chemical compound with the formula CH2O. It is the simplest aldehyde. Formaldehyde also exists as the cyclic trimer trioxane and the polymer paraformaldehyde. It exists in water as the hydrate H2C2. Aqueous solutions of formaldehyde are referred...
.
Uses
The principal application, consuming approximately 80% of the MMA, is the manufacture of polymethyl methacrylate acrylic
plasticPlastic is the general common term for a wide range of synthetic or semisynthetic organic amorphous solid materials suitable for the manufacture of industrial products...
s (PMMA). Methyl methacrylate is also used for the production of the co-polymer methyl methacrylate-butadiene-styrene (MBS), used as a modifier for
PVCPolyvinyl chloride is a plastic.PVC may also refer to:*Param Vir Chakra, India's highest military honor*Peripheral venous catheter - a small, flexible tube placed into a peripheral vein in order to administer medication or fluids...
.
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