2-피롤리디논

log Kow= -0.85

-0.85

1.116 @ 25 °C

Relative density (water = 1): 1.1

1.116 @25 °C

CRYSTALS FROM COLD PETROLEUM ETHER

Light yellow liquid

Very sol in alcohol, ether, benzene, chloroform, carbon disulfide

Infinitely soluble in water

1000 mg/mL at 20 °C

Solubility in water: good

265 °F (129 °C) (open cup)

129 °C o.c.

245 °C @ 760 mm Hg; 113-114 @ 9.2 mm Hg; 76 °C @ 0.2 mm Hg

245 °C

245 °C @760 [mm Hg]

This chemical does not meet GHS hazard criteria for 21.1% (116 of 551) of reports.

Danger

H315 (17.4%): Causes skin irritation [Warning Skin corrosion/irritation]

P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 551 reports by companies from 30 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Chemical: 2-Pyrrolidinone

2-Pyrrolidinone is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Pyrrolidinone are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 10-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14900

2-Pyrrolidinone: Does not have an individual approval but may be used under an appropriate group standard

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.

Skin Irrit. 2 (17.4%)

Serious eye damage/eye irritation - Category 2

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.

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.

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).

Redness.

Pain. Redness. Blurred vision.

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.

Samples of adult lake trout or walleye collected in 1977 from each of the Great Lakes and Lake St. Clair with each sampling site consisting of 20 large fish composited into one sample; 2-pyrrolidone was detected in trout from Lake Michigan, concentration not specified(1).

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.

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).

PYRROLIDONE ADMINISTERED BY GASTRIC GAVAGE TO RATS SHOWED LD100, LD50, & MAXIMUM TOLERABLE DOSES OF 10, 7.3 & 4 G/KG, RESPECTIVELY. TOPICAL APPLICATION TO THE EYES OF RABBITS CAUSED IRREVERSIBLE CLOUDING OF THE CORNEA.

NO EPILEPTOID ACTIVITY WAS OBTAINED WITH ADMIN OF 4-AMINOBUTYRIC ACID LACTAM (18 MMOL/KG, IP) IN SPRAGUE-DAWLEY RATS. THE EEG WAS DESYNCHRONIZED.

THE EFFECTIVENESS OF A VARIETY OF AMIDE-CONTAINING COMPOUNDS WERE STUDIED TO DETERMINE THE STRUCTURAL FEATURES REQUIRED FOR INDUCTION OF LEUKEMIA CELL DIFFERENTIATION. SUBSTITUED AMIDES WERE EFFECTIVE INDUCERS OF THE DIFFERENTIATION OF MURINE ERYTHROLEUKEMIA (FRIEND) CELLS, AS JUDGED BY THE CELLULAR ACCUMULATION OF HB. ERYTHROID DIFFERENTIATION WAS ASSESSED BY MEASURING THE PERCENTAGE OF BENZIDINE-POSITIVE (IE, HEMOGLOBIN-CONTAINING) CELLS. 2-PYRROLIDONE EXERTED A HIGH INDUCTION (89% BENZIDINE-POSITIVE CELLS) AT A CONCN OF 100 MMOL AFTER 6 DAYS OF CONTINUOUS EXPOSURE.

THE EFFECT OF VARIOUS POLAR ORGANIC COMPOUNDS ON THE OVERALL TRANSCRIPTION OF CHROMATIN FROM FRIEND-VIRUS-INFESTED ERYTHROLEUKEMIA CELLS WITH E COLI RNA POLYMERASE WAS INVESTIGATED. ALL OF THE COMPOUNDS, INCLUDING 2-PYRROLIDONE, WERE FOUND TO STIMULATE TRANSCRIPTION & INDUCE HEMOGLOBIN SYNTHESIS IN FRIEND CELLS. THE OVERALL TRANSCRIPTION INCREASED BY A FACTOR OF 1.3 AT A 230 MMOL CONCN OF 2-PYRROLIDONE.

For more Non-Human Toxicity Excerpts (Complete) data for 2-PYRROLIDONE (11 total), please visit the HSDB record page.

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.

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 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.

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 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.

Used as an intermediate in the manufacture of polyvinylpyrrolidone and polypyrrolidone (a polymer, formed in presence of alkaline catalysts); as high-boiling solvent in petroleum processing and acrylonitrile manufacture; in specialty printers inks; as an industrial solvent for polymers, chlordane, DDT, sorbitol, glycerol, iodine, and sugars; as plasticizer and coalescing agent for acrylic-styrene emulsion-type floor polishes; as a chemical intermediate for n-vinyl-2-pyrrolidone and nylon 4 fibers; as a monomer for copolymers with vinyl compounds; as constituent of pharmaceutical preparations; for polyhydroxylic alcohols and ethyl acetate; [HSDB]

Intermediate in mfr of polyvinylpyrrolidone & polypyrrolidone (polymer, formed in presence of alkaline catalysts); used as high-boiling solvent in petroleum processing, acrylonitrile mfr; in specialty printers inks; industrial solvent for polymers, Chlordane, DDT, sorbitol, glycerol, iodine, sugars; as plasticizer & coalescing agent for acrylic-styrene emulsion-type floor polishes

CHEM INT FOR N-VINYL-2-PYRROLIDONE; CHEM INT FOR NYLON 4 FIBERS; SOLVENT; MONOMER FOR COPOLYMERS WITH VINYL COMPOUNDS

USED AS CONSTITUENT OF PHARMACEUTICAL PREPARATIONS

Polyhydroxylic alcohols and ethyl acetate.

(1972) 6.22X10+7 GRAMS

(1975) 3.23X10+7 GRAMS

2023: 40,000,000 - <55,000,000 lb

(1972) 7.7X10+9 GRAMS

REACTION OF GAMMA-BUTYROLACTONE AND AMMONIA

From acetylene & formaldehyde by high-pressure synth.

Prepd on large scale from butyrolactone by Reppe process.

Printing Ink Manufacturing

2-Pyrrolidinone: ACTIVE