|Skeletal formula of acetone cyanohydrin|
|Jmol 3D model||Interactive image|
|Molar mass||85.11 g·mol−1|
|Density||932 mg mL−1|
|Melting point||−21.2 °C; −6.3 °F; 251.9 K|
|Boiling point||95 °C (203 °F; 368 K)|
|Vapor pressure||2 kPa (at 20 °C)|
Refractive index (nD)
Std enthalpy of
|−121.7–−120.1 kJ mol−1|
Std enthalpy of
|−2.4514–−2.4498 MJ mol−1|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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. It is extremely toxic.
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. 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.
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.
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- "acetone cyanohydrin - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification. Retrieved 8 June 2012.
- Bauer, Jr., William (2002), "Methacrylic Acid and Derivatives", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, ISBN 3-527-30673-0, doi:10.1002/14356007.a16_441.
- Cox, R. F. B.; Stormont, R. T. "Acetone Cyanohydrin". Org. Synth.; Coll. Vol., 2, p. 7
- Wagner, E. C.; Baizer, Manuel. "5,5-Dimethylhydantoin". Org. Synth.; Coll. Vol., 3, p. 323