Acetone cyanohydrin

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Acetone cyanohydrin
Skeletal formula of acetone cyanohydrin
Names
IUPAC name
2-Hydroxy-2-methylpropanenitrile[2]
Other names
Cyanohydrin-2-propanone[1]

α-Hydroxyisobutyronitrile[1]
2-Hydroxy-2-methyl-propionitrile[1]

2-Methylactonitrile[1]
Identifiers
75-86-5 YesY
3DMet B00479
605391
ChEBI CHEBI:15348 YesY
ChemSpider 6166 YesY
DrugBank DB02203 YesY
EC Number 200-909-4
Jmol 3D model Interactive image
KEGG C02659 YesY
MeSH acetone+cyanohydrin
PubChem 6406
RTECS number OD9275000
UN number 1541
Properties
C4H7NO
Molar mass 85.11 g·mol−1
Appearance Colourless liquid
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)
1.399
Thermochemistry
−121.7–−120.1 kJ mol−1
−2.4514–−2.4498 MJ mol−1
Vapor pressure {{{value}}}
Related compounds
Related alkanenitriles
Related compounds
DBNPA
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
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. It is extremely toxic.

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.[3] In the laboratory, this compound may be prepared by reacting sodium cyanide with acetone, followed by acidification:[4]

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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.[5]

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.

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

  1. 1.0 1.1 1.2 1.3 Cite error: Invalid <ref> tag; no text was provided for refs named NIOSH
  2. "acetone cyanohydrin - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification. Retrieved 8 June 2012. 
  3. 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 .
  4. Cox, R. F. B.; Stormont, R. T. "Acetone Cyanohydrin". Org. Synth. ; Coll. Vol., 2, p. 7 
  5. Wagner, E. C.; Baizer, Manuel. "5,5-Dimethylhydantoin". Org. Synth. ; Coll. Vol., 3, p. 323 

External links