| Acetone cyanohydrin | |
|---|---|
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| IUPAC name |
2-hydroxy-2-methylpropanenitrile
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| Identifiers | |
| CAS number | 75-86-5  |
| PubChem | 6406 |
| EC-number | 200-909-4 |
| SMILES |
N#CC(O)(C)C
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| InChI |
1/C4H7NO/c1-4(2,6)3-5/h6H,1-2H3
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| InChI key | MWFMGBPGAXYFAR-UHFFFAOYAL |
| ChemSpider ID | 6166 |
| 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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| (what is this?) (verify) 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 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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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]
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:.
- ^ 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
External links
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