Acetone cyanohydrin

Acetone cyanohydrin
Names
	IUPAC name 2-hydroxy-2-methylpropanenitrile
Identifiers
CAS Number	75-86-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	6166;
ECHA InfoCard	100.000.828
PubChem CID	6406;
CompTox Dashboard (EPA)	DTXSID7025427 ;
	InChI InChI=1/C4H7NO/c1-4(2,6)3-5/h6H,1-2H3 Key: MWFMGBPGAXYFAR-UHFFFAOYAL;
	SMILES N#CC(O)(C)C;
Properties
Chemical formula	C4H7NO
Molar mass	85.105 g/mol
Density	0.932 g/cm3
Melting point	−19 °C
Boiling point	95 °C
Hazards
NFPA 704 (fire diamond)	4 1 2
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.

Preparation

The compound is generated as part of the acetone cyanohydrin (ACH) 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 involving the action of sodium or potassium cyanide on the sodium bisulfite adduct of acetone prepared in situ is possible, though the quality of the product is inferior.^[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

^ Bauer, Jr., William (2002), "Methacrylic Acid and Derivatives", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a16_441.
^ Cox, R. F. B.; Stormont, R. T. "Acetone Cyanohydrin". Organic Syntheses; Collected Volumes, vol. 2, p. 7.
^ Wagner, E. C.; Baizer, Manuel. "5,5-Dimethylhydantoin". Organic Syntheses; Collected Volumes, vol. 3, p. 323.

External links

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

[1] Bauer, Jr., William (2002), "Methacrylic Acid and Derivatives", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a16_441.

[2] Cox, R. F. B.; Stormont, R. T. "Acetone Cyanohydrin". Organic Syntheses; Collected Volumes, vol. 2, p. 7.

[3] Wagner, E. C.; Baizer, Manuel. "5,5-Dimethylhydantoin". Organic Syntheses; Collected Volumes, vol. 3, p. 323.

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