Lactonitrile

Lactonitrile Basic information
Product Name:Lactonitrile
Synonyms:propanenitrile,2-hydroxy-;Propionitrile, 2-hydroxy-;DL-LACTONITRILE, STAB.;acetaldehydcyanhydrin;2-hydroxypropylnitrile;ethylidene cyanhydrin;lactonitrite;β-hydroxypropionitrile
CAS:78-97-7
MF:C3H5NO
MW:71.08
EINECS:201-163-2
Product Categories:Building Blocks;C1 to C5;Chemical Synthesis;Cyanides/Nitriles;Nitrogen Compounds;Organic Building Blocks
Mol File:78-97-7.mol
Lactonitrile Structure
Lactonitrile Chemical Properties
Melting point -40.15°C
Boiling point 90 °C17 mm Hg(lit.)
density 0.991 g/mL at 20 °C(lit.)
vapor pressure 15.9Pa at 25℃
refractive index n20/D 1.404
Fp 77 °C
storage temp. Refrigerator, under inert atmosphere
solubility DMSO (Slightly), Methanol (Slightly)
form Oil
pka11.38±0.20(Predicted)
color Colourless
BRN 605366
LogP-0.32 at 25℃
CAS DataBase Reference78-97-7(CAS DataBase Reference)
NIST Chemistry ReferencePropanenitrile, 2-hydroxy-(78-97-7)
EPA Substance Registry SystemLactonitrile (78-97-7)
Safety Information
Hazard Codes T+,T
Risk Statements 23/25-27-25-20
Safety Statements 13-36/37/39-45-23-36/37-28
RIDADR UN 3276 6.1/PG 1
WGK Germany 3
RTECS OD8225000
HazardClass 6.1(a)
PackingGroup II
Hazardous Substances Data78-97-7(Hazardous Substances Data)
MSDS Information
ProviderLanguage
Lactonitrile English
SigmaAldrich English
Lactonitrile Usage And Synthesis
Chemical PropertiesLactonitrile, is soluble in water and alcohol, but insoluble in diethyl ether and carbon disulfide. Lactonitrile is used chiefly to manufacture lactic acid and its derivatives, primarily ethyl lactate.
Uses2-Hydroxypropanenitrile is a useful compound for efficient lactamide synthesis by fed batch method using nitrile hydratase of Rhodococcus pyridinivorans NIT-36.
UsesIt is used primarily as a solvent, and as an intermediate in production of ethyl acetate and lactic acid.
Production MethodsLactonitrile is manufactured from equimolar amounts of acetaldehyde and hydrogen cyanide containing 1.5% of 20% NaOH at ?10–20 °C. The product is stabilized with sulfuric acid. Sulfuric acid hydrolyzes the nitrile to give a mixture of lactic acid and ammonium bisulfate. This mixture can be purified by adding methanol to form methyl lactate which is separated from the ammonium bisulfate. The methyl lactate is distilled, then hydrolyzed back to the aqueous acid. Removal of most of the water yields 90% lactic acid.
Production MethodsLactonitrile is derived from acetaldehyde and hydrocyanic acid.
General DescriptionStraw colored liquid. Used as a solvent /intermediate in production of ethyl lactate and lactic acid.
Air & Water ReactionsWater soluble.
Reactivity ProfileLactonitrile is incompatible with strong acids, strong bases and strong reducing agents. Lactonitrile is also incompatible with strong oxidizers. In the presence of alkali, Lactonitrile evolves toxic compounds. .
Health HazardExtremely toxic by oral, skin, or eye contact.
Fire HazardCyanide fumes released when heated to decomposition. Avoid alkali, oxidizing material.
Tag:Lactonitrile(78-97-7) Related Product Information
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