Lactonitrile

HCID 6572CAS 42492-95-5

Basic information

Standard SMILES
CC(O)C#N
InChIKey
WOFDVDFSGLBFAC-UHFFFAOYSA-N
Molecular formula
C3H5NO
Average molar mass
71.08 g/mol
Monoisotopic mass
71.03711378

Overview

Straw colored liquid. Used as a solvent /intermediate in production of ethyl lactate and lactic acid. (EPA, 1998)

Names & identifiers

Preferred name
Lactonitrile
IUPAC
2-hydroxypropanenitrile
English name
2-HYDROXYPROPIONITRILE
Molecular formula
C3H5NO
Molecular weight
71.08

Names & synonyms

Lactonitrile2-HYDROXYPROPANENITRILE2-Hydroxypropionitrile78-97-7Propanenitrile, 2-hydroxy-AcetocyanohydrinAcetaldehyde, cyanohydrinPropionitrile, 2-hydroxy-Acetaldehyde cyanohydrinLaktonitrilEthylidene cyanohydrinalpha-Hydroxypropionitrile
Show more names
DL-LACTONITRILE2-HYDROXYETHYL CYANIDEACETALDEHYDCYANOHYDRINDL-lactonitrilestab.pure(±)-2-hydroxypropiononitrileDL-LACTONITRILE STAB. PURE 97+%
(1)-2-HydroxypropiononitrileDTXSID6025432SJ38QDA188NSC-7764DTXCID005432RefChem:152082201-163-2255-852-8

Database identifiers

CAS
42492-95-5、78-97-7
PubChem CID
6572
DTXSID
DTXSID6025432
ChEMBL
CHEMBL3559764
UNII
SJ38QDA188
EC Number
201-163-2、255-852-8
Nikkaji
J1.488E

Properties

Computed structural properties

XLogP
-0.3
Topological polar surface area
44 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
5

Experimental & physicochemical properties

Chemical Classes · 2 items

Nitrogen Compounds -> Nitriles

Flammable agents - 2nd degree

SpringerMaterials PropertiesCoriolis coupling
LogPlog Kow= -0.94
Density · 3 items

0.9877 at 68 °F (EPA, 1998) - Less dense than water; will float

0.9877 @ 20 °C/4 °C

0.9834 @25 °C

Color/Form · 2 items

YELLOW LIQUID

Straw-colored liq

Solubility · 3 items

greater than or equal to 100 mg/mL at 73 °F (NTP, 1992)

Soluble in water and alcohol; insoluble in petroleum ether and carbon disulfide.

Miscible in water and ethanol; soluble in ethyl ether and chloroform.

Physicochemical properties

Boiling point
90 °C17 · 90 °C17 mm Hg(lit.)
Density
0.991 g/mL · 0.991 g/mL at 20 °C(lit.)
refractive index
20 · n20/D 1.404
FDA UNII
38 QDA188 · SJ38QDA188
Symbol(GHS)
6 · GHS06
Signal word
Danger

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 27% (55 of 204) of reports.

Danger

H300 (52.9%): Fatal if swallowed [Danger Acute toxicity, oral]

P260, P261, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P317, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 204 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Hazard information

Regulatory Information · 3 items

Chemical: Propanenitrile, 2-hydroxy-

Status: Active Update: 27-01-2014 https://echa.europa.eu/registration-dossier/-/registered-dossier/10462

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelPoison
Fire HazardsCyanide fumes released when heated to decomposition. Avoid alkali, oxidizing material. (EPA, 1998)
Fire PotentialIT HAS MODERATE FIRE HAZARD WHEN EXPOSED TO HEAT OR FLAME ...
Health HazardsExtremely toxic by oral, skin, or eye contact. (EPA, 1998)
Hazards Summary · 2 items

An eye irritant; Highly toxic by eye contact, ingestion, and skin absorption; Emergency treatment: Lactonitrile; May cause cyanide poisoning after a delay of several hours; An oral dose of >10 mg/kg is lethal in animals, as is 0.05 ml applied to the eye and 1 mg/kg applied to the skin; [HSDB] Cyanide fumes released when heated to decomposition. Avoid alkali, oxidizing material. . . . Extremely toxic by oral, skin, or eye contact. [CAMEO] May cause irritation; Readily absorbed through skin (may be fatal); [Aldrich MSDS] See NITRILES.

The major hazards encountered in the use and handling of 2-hydroxypropanenitrile stem from its toxicologic properties. Extremely toxic by inhalation, and dermal or eye contact, exposure to this colorless-to-yellow liquid may occur from its use as a solvent and intermediate in the production of ethyl acetate and lactic acid. Effects from exposure may include initially headache, dizziness, and agitation, followed by combative behavior, coma, and death. This substance is a moderate fire hazard when exposed to heat or flame.

Safety & protection

Fire FightingFoam, carbon dioxide, dry chemical. (EPA, 1998)
First AidWarning: Heart palpitations may occur within minutes after exposure. Caution is advised. Vital signs should be monitored closely. Symptoms may be delayed.
Nonfire Spill Response · 1 item

Caution : Lactonitrile toxicity can occur via ingestion, dermal/eye contact, or ingestion; death may occur within minutes. IMMEDIATELY begin administering 100% oxygen and rush victims to a health care facility. Toxic hydrogen cyanide gas may be released upon contact with alkali or when heated to decomposition.

Disposal Methods · 2 items

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste numbers D003 and P030 must conform with USEPA regulations in storage, transportation, treatment and disposal of waste. /Cyanide cmpd/

A poor candidate for incineration. /Cyanides/

Preventive Measures · 2 items

All nitriles should be handled under carefully controlled conditions and only by personnel having a thorough understanding and knowledge of safe handling techniques. Because of the nature of nitrile cmpd and the lack of complete toxicity data on many nitriles, care should be exercised in handling these cmpd to avoid inhalation of the vapors, ingestion, and contact with the skin. /Nitriles/

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Isolation and EvacuationExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

Toxicology

Ecotoxicity Values · 3 items

TLm Pinperch 0.215 mg/l/24 hr in sea water. /Conditions of bioassay not specified/

TLm Pimephales promelas (fathead minnow) 0.9 mg/l/96 hr. /Conditions of bioassay not specified/

TLm Guppies 1.37 mg/l/96 hr. /Conditions of bioassay not specified/

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that 2-hydroxypropanenitrile is expected to have very high mobility in soil(SRC). Volatilization of 2-hydroxypropanenitrile from moist soil surfaces may be an important fate process(SRC) based on the estimated Henry's Law constant of 9.8X10-6 atm-cu m/mole, estimated using a fragment constant estimation method(3). 2-Hydroxypropanenitrile is expected to hydrolyze in moist soil surfaces to acetaldehyde and hydrogen cyanide(4). Although the kinetics of hydrolysis for 2-hydroxypropanenitrile are unknown, a structurally similar chemical, 2-hydroxy-2-methyl-propanenitrile, has a reported hydrolysis half-life of 9 minutes at pH 7.2 and 26 °C(5). 2-Hydroxypropanenitrile is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.119 mm Hg(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that 2-hydroxypropanenitrile is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(SRC) based upon an estimated Henry's Law constant of 9.8X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are calculated to be 3 days and 26 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow of -0.94(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low. However, a hydrolysis half-life of 9 minutes for the structurally related 2-hydroxy-2-methyl-propanenitrile(8), suggests that 2-hydroxypropanenitrile will hydrolyze rapidly in the environment and volatilization, bioconcentration, and biodegradation will not be important fate processes(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-hydroxypropanenitrile, which has a vapor pressure of 0.119 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-hydroxypropanenitrile is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 10 days(SRC), calculated from its rate constant of 1.60X10-12 cu cm/molecule-sec at 25 °C, determined using a structure estimation method(3).

Adverse EffectsOther Poison - Chemical Asphyxiant
Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 2-hydroxypropanenitrile can be estimated to be about 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-hydroxypropanenitrile is expected to have very high mobility in soil. 2-Hydroxypropanenitrile hydrolyzes in water(3) which suggests that leaching in soil is likely to occur(SRC).

Human Toxicity ExcerptsIt is unknown whether or not lactonitrile produces its /toxic/ effects by virtue of hydrolysis to give cyanide ion or whether it acts as molecule.
Artificial Pollution Sources2-Hydroxypropanenitrile's production and use as an solvent or chemical intermediate(1) may result in its release to the environment through various waste streams(SRC).

Regulatory information

RCRA Requirements · 1 item

D003; A solid waste containing a cyanide cmpd may become characterized as a hazardous waste when subjected to testing for reactivity as stipulated in 40 CFR 261.23, and if so characterized, must be managed as a hazardous waste. ... Cyanide bearing waste which, when exposed to pH conditions between 2 and 12.5, can generate toxic gases, vapors or fumes in a quantity sufficient to present a danger to human health or the environment. /Cyanide cmpd/

TSCA Requirements · 1 item

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Propanenitrile, 2-hydroxy- is included on this list.

CERCLA Reportable Quantities · 1 item

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Lactonitrile is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 1,000 lbs.

Safety data

wgk
3
ridadr
UN 3276 6.1/PG 1
risk_code
23/25-27
Signal word
Danger
Symbol(GHS)
GHS06
hazard_code
T+

Chemistry & industry

Uses & manufacturing

Uses · 2 items

Used as a solvent and to make ethyl lactate and lactic acid; [Hawley] Used as an intermediate for the production of alanine, acrylic fibres, resins, and acrylic acid; [eChemPortal: SIDSUNEP]

Solvent; intermediate in production of ethyl acetate and lactic acid

U.S. Production · 2 items

(1979) PROBABLY GREATER THAN 2.27X10+6 G

(1981) PROBABLY GREATER THAN 2.27X10+6 G

Methods of ManufacturingAcetaldehyde and hydrocyanic acid.
Formulations/PreparationsGrades: technical; 95-97% purity
General Manufacturing InformationPropanenitrile, 2-hydroxy-: ACTIVE

Suppliers3 total

成都华纯科技有限公司400-1166-196 15982826727 · [email protected]
重庆卡兰医药有限公司[email protected]
南京世洲生物科技有限公司025-85563444 15850508050 · [email protected]

Related reactions

22 records

Linked notes

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