Lactonitrile Basic information
Product Name:Lactonitrile
Synonyms:propanenitrile,2-hydroxy-;Propionitrile, 2-hydroxy-;DL-LACTONITRILE, STAB.;acetaldehydcyanhydrin;2-hydroxypropylnitrile;ethylidene cyanhydrin;lactonitrite;β-hydroxypropionitrile
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
color Colourless
BRN 605366
Dielectric constant38.4(20℃)
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
Lactonitrile English
SigmaAldrich English
Lactonitrile Usage And Synthesis
DescriptionLactonitrile is a colorless to straw-coloredliquid. Molecular weight= 71.09; Boiling point= 183℃(slight decomposition); FreezingMelting point= - 40℃;Flash point= 77℃. Hazard Identification (based on NFPA-704M Rating System): Health 3, Flammability 2,Reactivity 0. Soluble in water.
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.
Potential ExposureThis material is used as a solvent andas an intermediate in the production of ethyl lactate and lac-tic acid.
First aidIf this chemical gets into the eyes, remove anycontact lenses at once and irmigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek med-ical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal prec autions, includ-ing resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medi-cal attention. GiveI large quantities of water and inducevomiting. Do not make an unconscious person vomit.
storageColor Code-B lue: Health Hazard/Poison: Storein a secure poison location.Prior to working with this chemical you should be trained on its proper handling andstorage. Store in tighty closed containers in a cool, well-venti lated area away from oxidizers and alkalis. Store in arefrigerator under an inert atmosphere and protect fromlight for prolonged storage. Where possible, automaticallypump liquid from drums or other storage containers to pro-cess cont ainers.
ShippingNitriles,toxic,n.o.s.mustbelabeled“POISONOUS/TOXIC MATERIALS." This chemical fallsin Hazard Class 6.1.
IncompatibilitiesAlkalis form hydrogen cyanide. Violentreaction with strong oxidizers.
Tag:Lactonitrile(78-97-7) Related Product Information
Hydroxy silicone oil 3-Aminopropionitrile 4-Hydroxybenzoic acid 2-Hydroxypyridine Hydroxyapatite 10-Hydroxycamptothecin Glycolic acid BETA-HYDROXYPROPIONITRILE,3-HYDROXYPROPIONITRILE,3-HYDROXYPROPIONITRILE, 99+%,3-Hydroxypropionitrile, Pract.,3-HYDROXYPROPIONITRILE GR DL-LACTONITRILE STAB. PURE 97+%,DL-LACTONITRILE,2-HYDROXYPROPIONITRILE 2-Methyl-2-hydroxypropionitrile,Lactonitrile, 2-methyl-,2-METHYL-LACTONITRILE Lactonitrile Acetaldehyde Propionitrile trichlorolactonitrile 2-HYDROXYPROPIONITRILE SOLUTION 100UG/ML IN METHYLENE CHLORIDE 5ML 3-HYDROXYPROPIONITRILE-2,2,3,3-D4 2-Phenyl-2-hydroxypropionitrile phthalic acid, diester with lactonitrile