2-Pyrrolidone

85.1

85.10

210-483-1

KKL5D39EOL

0562

8413|4593

DTXSID8027246

CRYSTALS FROM COLD PETROLEUM ETHER|Light yellow liquid

2933790090

29.1

-0.85

Clear colorless to pale yellow Liquid or Low Melting Mass

1.116 g/cm³ @ Temp: 25 °C

25.0 °C

76 °C @ Press: 0.2 Torr

>230 °F

1.486-1.488

Micible with water.

2-8°C

Vapour pressure at 20°C: negligible

2.9 (vs air)

LD50 orally in Rabbit: > 3200 mg/kg

1.8-16.6%(V)

pKa= 14.7

Dipole moment: 2.3|In presence of stoichiometric amt of water crystalline monohydrate, MP 30 deg, can be formed

-546.9

Non-corrosive

666 kJ/kg (enthalpy of evaporation)

Critical Temperature: 802 K; Critical Pressure: 6.17X10+6 Pa

III

6.1(b)

2810

1

22

24/25

UY5715000

Ventilation along the floor.

GOOD CHEMICAL STABILITY

P305 + P351 + P338

H319

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Danger|H302 (10.19%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 595 companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

SLIGHT, WHEN EXPOSED TO HEAT OR FLAME. ...CAN REACT WITH OXIDIZING MATERIALS.

ALCOHOL FOAM, CO2, DRY CHEMICAL.

Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Ventilation along the floor.

A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.

The substance is irritating to the skin, eyes and respiratory tract.

NO open flames.

Protective gloves.

Wear safety spectacles.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.

LD50 Rat oral 6500 mg/kg|LD50 Guinea pig oral 6500 mg/kg

2-Pyrrolidone's production and use as a precursor to N-vinyl-2-pyrrolidone(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 17(SRC), determined from a structure estimation method(2), indicates that 2-pyrrolidone is expected to have very high mobility in soil(SRC). Volatilization of 2-pyrrolidone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.06X10-9 atm-cu m/mole(3). 2-Pyrrolidone is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.49X10-3 mm Hg(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 17(SRC), determined from a structure estimation method(2), indicates that 2-pyrrolidone is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.06X10-9 atm-cu m/mole(4,SRC). According to a classification scheme(5), an estimated BCF of 3(3,SRC), from a log Kow of -0.85(6), suggests the potential for bioconcentration in aquatic organisms is low.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-pyrrolidone, which has a vapor pressure of 9.49X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-pyrrolidone 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 28 hrs(SRC) calculated from its rate constant of 1.35X10-11 cu cm/molecule sec(SRC), determined using a structure estimation method(3).

The rate constant for the vapor-phase reaction of 2-pyrrolidone with photochemically-produced hydroxyl radicals has been estimated as 1.35X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1 day at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the reaction of 2-pyrrolidone with the hydroxyl radical in aqueous solution is 2.2X10+9 l/mol sec(2) with a half life of 1 year(SRC) assuming a hydroxyl radical concentration of 1X10-17 mol/l(3). 2-Pyrrolidone is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum.

An estimated BCF of 3 was calculated for 2-pyrrolidone(SRC), using a log Kow of -0.85(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 2-pyrrolidone can be estimated to be about 17(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-pyrrolidone is expected to have very high mobility in soil.

The Henry's Law constant for 2-pyrrolidone is estimated as 1.06X10-9 atm-cu m/mole(SRC) from its vapor pressure, 9.49X10-3 mm Hg(1), and miscibility in water(2). This Henry's Law constant indicates that 2-pyrrolidone is expected to be essentially nonvolatile from water surfaces(3). 2-Pyrrolidone's estimated Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces will not occur(SRC). 2-Pyrrolidone is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.49X10-3 mm Hg(1).

DRINKING WATER: 2-Pyrrolidone was detected in 3 out of 13 samples taken from finished drinking water in Cincinnati, OH on January 14, 1980, units not specified(1).|SURFACE WATER: A study of various scientific articles related to concentrations of known pollutants in the waters of the Great Lakes was done by the Water Quality Board in 1982. In both Lake St. Clair and Lake Michigan, 2-pyrrolidone had been detected, concentration not specified(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 1,215 workers (259 of these are female) are potentially exposed to 2-pyrrolidone in the US(1). Occupational exposure to 2-pyrrolidone may occur through inhalation and dermal contact with this compound at workplaces where pyrrolidone is produced or used(SRC). The general population may be exposed to pyrrolidone via ingestion of fish(2) and drinking water(3).

The percutaneous absorption has been investigated in rats of a mixture (3:2, w/w) of N-methyl-2-pyrrolidinone and 2-pyrrolidinone, a combination intended for use as a vehicle in the formulation of an antimycotic drug to enhance skin penetration on dermal application, following co-administration of the two (14)C-radiolabelled compounds by the dermal and oral routes. Radioactivity was excreted predominantly in the urine after either route of administration, and comparison of the respective excretion profiles indicated that about three-quarters of the applied dose was absorbed through the skin. Plasma concentrations of each parent compound, as determined by radio-HPLC, reached peak values at 2 hr after oral dosing, and remained relatively uniform during 1-6 hr after application to the skin, suggesting constant percutaneous absorption during this period. N-Methyl-2-pyrrolidinone appeared to be absorbed through the skin more extensively and at a slightly faster rate than 2-pyrrolidinone; total percutaneous absorption tended to be more extensive in female than in male rats. Together, these two 14C-compounds accounted for most of the plasma radioactivity up to 6-8 hr post-administration. However, by 12 hr (when plasma levels were relatively low), most of the radioactivity was associated with unknown polar metabolites. In view of the extensive percutaneous absorption and little first-pass metabolism of the two pyrrolidinones, the oral route was considered to represent a valid alternative to the dermal route for the assessment of the systemic toxicity of the two compounds.

THE URINARY EXCRETION OF RADIOACTIVE METABOLITES FOLLOWING THE IP ADMIN OF A RANGE OF DOSES OF 2,5-(14)C-2-LABELED N-NITROSOPYRROLIDINE TO RATS WAS EXAMINED. PYRROLIN-2-ONE WAS ONE OF SEVERAL METABOLITES IDENTIFIED.|PYRROLIDONE WAS IDENTIFIED AS A URINARY METABOLITE OF METHADONE.|AN ENZYME SYSTEM RESIDING IN THE SOL FRACTION OF RABBIT LIVER CATALYZES THE CONVERSION OF DELTA 1-PYRROLINE TO GAMMA-AMINOBUTYRIC ACID & ITS LACTAM, 2-PYRROLIDONE.|2-PYRROLIDONE WAS IDENTIFIED AS A METABOLITE OF (14)C-PUTRESCINE IN SLICED RAT LIVER IN VITRO. IT IS ALSO SYNTHESIZED FROM PUTRESCINE BY THE SPLEEN & LUNG, BUT NOT BY KIDNEY, BRAIN, HEART OR MUSCLE.|For more Metabolism/Metabolites (Complete) data for 2-PYRROLIDONE (6 total), please visit the HSDB record page.

THE MECHANISMS OF SKIN PENETRATION ENHANCERS WERE INVESTIGATED BY MEASURING STEADY-STATE FLUXES IN VITRO FOR MODEL COMPOUNDS, METHANOL, OCTANOL & CAFFEINE. 2-PYRROLIDONE ENHANCED THEIR PERMEATION THROUGH THE POLAR ROUTE OF THE SKIN BY INCREASING THE DIFFUSIVITY & DECREASED PASSAGE THROUGH THE NONPOLAR ROUTE BY DECREASING DIFFUSIVITY & PARTITIONING.|TRYPSINIZED, ABDOMINAL STRATUM CORNEUM ABSORBED 1-4 TIMES ITS WT OF PRIMARY ALCOHOLIC VEHICLE FROM SOLUTIONS OF 0-80% WT 2-PYRROLIDONE IN WATER; ABOUT 2 SEPARATION PARTITION COEFFICIENTS OPERATED. CALCULATIONS OF HM VALUES FOR THE PARTITIONS INDICATED THAT 2-PYRROLIDONE IS PROBABLY NOT A PENETRATION ACCELERANT FOR C1-C8 PRIMARY ALCOHOLS.|FOR THE SIMPLE NONELECTROLYTES TESTED, & UNDER IDEALIZED IN VITRO STEADY STATE CONDITIONS, 2-PYRROLIDONE ACTED AS A MILD ACCELERANT FOR POLAR MATERIAL (METHANOL) DIFFUSION THROUGH HUMAN STRATUM CORNEUM, BUT INHIBITED NONPOLAR, LIPOPHILIC (OCTANOL) TRANSPORT.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

2-pyrrolidinone

The substance can be absorbed into the body through the skin.

Redness.

Pain. Redness. Blurred vision.

Over 95% of the 2-pyrrolidone produced is processed into N-vinyl-2-pyrrolidone.

All other basic organic chemical manufacturing|2-Pyrrolidinone: ACTIVE

EFFLUENTS FROM PLANTS PRODUCING ACETYLENE ARE ANALYZED FOR ALPHA-PYRROLIDONE USING A COLUMN CONTAINING CELLITE-545 COATED WITH 15% PEG-6000 PLUS POTASSIUM HYDROXIDE. THE CARRIER GAS IS NITROGEN & A FLAME-IONIZATION DETECTOR IS USED.

2-OXOPYRROLIDINE DERIVATIVES WERE DETERMINED IN BIOLOGICAL MATERIALS AFTER FREEZE-DRYING BY EXTRACTION WITH CHLOROFORM-METHANOL (1:1), TLC ON SILICA GEL, & DETECTION WITH SPRAY REAGENT. BEST DETECTION WAS ACHIEVED WITH CHLOROTOLIDINE TEST & EHRLICH'S REAGENT. PROCEDURES ARE GIVEN FOR 2-OXOPYRROLIDINE IN PLASMA & URINE.