Acetone cyanohydrin

Acetone cyanohydrin
IUPAC name 2-hydroxy-2-methylpropanenitrile
Identifiers
CAS number	75-86-5 Y
PubChem	6406
ChemSpider	6166 Y
EC-number	200-909-4
DrugBank	DB02203
KEGG	C02659 Y
ChEBI	CHEBI:15348 Y
Jmol-3D images	Image 1
SMILES N#CC(O)(C)C
InChI InChI=1S/C4H7NO/c1-4(2,6)3-5/h6H,1-2H3 Y Key: MWFMGBPGAXYFAR-UHFFFAOYSA-N Y InChI=1/C4H7NO/c1-4(2,6)3-5/h6H,1-2H3 Key: MWFMGBPGAXYFAR-UHFFFAOYAL
Properties
Molecular formula	C4H7NO
Molar mass	85.105 g/mol
Density	0.932 g/cm3
Melting point	−19 °C
Boiling point	95 °C
Hazards
MSDS	Fisher MSDS
EU Index	608-004-00-X
NFPA 704	1 4 2
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Acetone cyanohydrin (ACH) is an organic compound used in the production of methyl methacrylate, the monomer 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 acid to give the sulfate ester of the methacrylamide, methanolysis of which gives ammonium bisulfate and MMA.^[1] In the laboratory, this compound may be prepared by reacting sodium cyanide with acetone, followed by acidification:^[2]

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.^[3]

Natural occurrence

Cassava 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.

Safety

Acetone cyanohydrin is classified as an extremely hazardous substance in the US Emergency Planning and Community Right-to-Know Act. The principal hazards of acetone cyanohydrin arise from its ready decomposition on contact with water, which releases highly toxic hydrogen cyanide.

References

External links

• SIDS Initial Assessment Report for Acetone cyanohydrin from the Organisation for Economic Co-operation and Development (OECD)