Acetone cyanohydrin
| Acetone cyanohydrin | |
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2-hydroxy-2-methylpropanenitrile |
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| Identifiers | |
| CAS number | 75-86-5  |
| PubChem | 6406 |
| ChemSpider | 6166 |
| EC-number | 200-909-4 |
| DrugBank | DB02203 |
| KEGG | C02659 |
| ChEBI | CHEBI:15348 |
| Jmol-3D images | Image 1 |
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| 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
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 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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.
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[edit] 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]
[edit] 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.
[edit] 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.
[edit] References
- ^ Bauer, Jr., William (2002), Methacrylic Acid and Derivatives, "Ullmann's Encyclopedia of Industrial Chemistry", Ullmann's Encyclopedia of Industrial Chemistry (Weinheim: Wiley-VCH), doi:10.1002/14356007.a16_441, ISBN 3527306730.
- ^ Cox, R. F. B.; Stormont, R. T., "Acetone Cyanohydrin", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv2p0007; Coll. Vol. 2: 7
- ^ Wagner, E. C.; Baizer, Manuel, "5,5-Dimethylhydantoin", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv3p0323; Coll. Vol. 3: 323
