Lactonitrile

Lactonitrile
Names
	IUPAC name 2-Hydroxypropanenitrile
	Other names Acetaldehyde cyanohydrin
Identifiers
CAS Number	78-97-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	21106532;
ECHA InfoCard	100.001.058
PubChem CID	6572;
UNII	SJ38QDA188 ;
CompTox Dashboard (EPA)	DTXSID6025432 ;
	InChI InChI=1S/C3H5NO/c1-3(5)2-4/h3,5H,1H3 Key: WOFDVDFSGLBFAC-UHFFFAOYSA-N; InChI=1/C3H5NO/c1-3(5)2-4/h3,5H,1H3 Key: WOFDVDFSGLBFAC-UHFFFAOYAF;
	SMILES N#CC(C)O;
Properties
Chemical formula	C3H5NO
Molar mass	71.079 g·mol−1
Appearance	Yellow
Melting point	−40 °C (−40 °F; 233 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Lactonitrile is the organic compound with the formula CH₃CH(OH)CN. It is an intermediate in the industrial production of ethyl lactate and lactic acid.^[1]^[2]^[3] It is the cyanohydrin of acetaldehyde. It is a colorless liquid, although degraded samples can appear yellow.

Synthesis and use[edit]

Lactonitrile is obtained by the addition of hydrogen cyanide to acetaldehyde.^[1]

Lactonitrile is used in making esters of lactic acid.^[1]

Cyanohydrins are sources of highly toxic hydrogen cyanide. The substance is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.^[4]

^ ^a ^b ^c Westhoff, Gerrit; Starr, John N. (2012). "Lactic Acids". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_097.pub3. ISBN 978-3527306732.
^ "Lactonitrile". EChA. echa.europa.eu. Retrieved 13 June 2017.
^ Lactonitrile at www.chemicalbook.com.
^ "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011. {{cite journal}}: Cite journal requires |journal= (help)