Acetone cyanohydrin
Encyclopedia
Acetone cyanohydrin is an organic compound
used in the production of methyl methacrylate
, the monomer
of the transparent plastic polymethyl methacrylate (PMMA), also known as acrylic.
to give the sulfate ester of the methacrylamide, methanolysis of which gives ammonium bisulfate
and MMA. In the laboratory, this compound may be prepared by reacting sodium cyanide
with acetone
, followed by acidification:
A simplified procedure involves the action of sodium or potassium cyanide on the sodium bisulfite adduct of acetone prepared in situ. This gives a less pure product that is suitable for most syntheses.
tubers contain linamarin
, a glucoside
of acetohydrin, and the enzyme linamarinase for hydrolysing the glucoside. Crushing the tubers releases these compounds and produces acetone cyanohydrin, which is potentially lethally toxic.
. The principal hazards of acetone cyanohydrin arise from its ready decomposition on contact with water, which releases highly toxic hydrogen cyanide.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
used in the production of methyl methacrylate
Methyl methacrylate
Methyl methacrylate is an organic compound with the formula CH2=CCOOCH3. This colourless liquid, the methyl ester of methacrylic acid is a monomer produced on a large scale for the production of poly .-Production:...
, the monomer
Monomer
A monomer is an atom or a small molecule that may bind chemically to other monomers to form a polymer; the term "monomeric protein" may also be used to describe one of the proteins making up a multiprotein complex...
of the transparent plastic polymethyl methacrylate (PMMA), also known as acrylic.
Preparation
The compound is generated as part of the acetone cyanohydrin route to methyl methacrylate. It is treated with sulfuric acidSulfuric acid
Sulfuric acid is a strong mineral acid with the molecular formula . Its historical name is oil of vitriol. Pure sulfuric acid is a highly corrosive, colorless, viscous liquid. The salts of sulfuric acid are called sulfates...
to give the sulfate ester of the methacrylamide, methanolysis of which gives ammonium bisulfate
Ammonium bisulfate
Ammonium 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, NH3. ...
and MMA. In the laboratory, this compound may be prepared by reacting sodium cyanide
Sodium cyanide
Sodium cyanide is an inorganic compound with the formula NaCN. This highly toxic colorless salt is used mainly in gold mining but has other niche applications...
with acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...
, followed by acidification:
A simplified procedure involves the action of sodium or potassium cyanide on the sodium bisulfite adduct of acetone prepared in situ. This gives a less pure product that is suitable for most syntheses.
Natural occurrence
CassavaCassava
Cassava , also called yuca or manioc, a woody shrub of the Euphorbiaceae native to South America, is extensively cultivated as an annual crop in tropical and subtropical regions for its edible starchy tuberous root, a major source of carbohydrates...
tubers contain linamarin
Linamarin
Linamarin is a cyanogenic glucoside found in the leaves and roots of plants such as cassava, lima beans, and flax. It is a glucoside of acetone cyanohydrin...
, a glucoside
Glucoside
A glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes....
of acetohydrin, and the enzyme linamarinase for hydrolysing the glucoside. Crushing the tubers releases these compounds and produces acetone cyanohydrin, which is potentially lethally toxic.
Safety
Acetone cyanohydrin is classified as an extremely hazardous substance in the US Emergency Planning and Community Right-to-Know ActEmergency Planning and Community Right-to-Know Act
The Emergency Planning and Community Right-to-Know Act of 1986 is a United States federal law passed by the 99th United States Congress located at Title 42, Chapter 116 of the U.S. Code, concerned with emergency response preparedness....
. The principal hazards of acetone cyanohydrin arise from its ready decomposition on contact with water, which releases highly toxic hydrogen cyanide.