N-vinyl-2-pyrrolidone

log Kow = 0.37

0.4

1.04 @ 24 °C/4 °C

Relative density (water = 1): 1.04

1..04

1.04 @25 °C

2.07 cps @ 25 °C

2.07 cP at 25 °C

Soluble in water and many organic solvents

In water, 5.2X10+4 mg/L @ 25 °C /Estimated/

Solubility in water: very good

95 °C

100.5 °C (213 °F) open cup

95 °C closed cup

93 °C

199.4 °F

96 °C @ 14 mm Hg; 193 °C @ 400 mm Hg

at 1.3kPa: 90-93 °C

194 °F

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P318, P319, P321, P330, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.1% (1 of 963) of reports.

Danger

H302 (97.2%): Harmful if swallowed [Warning Acute toxicity, oral]

Chemical: Poly[1-(2-oxo-1-pyrrolidinyl)-1,2-ethanediyl]

Chemical: 2-Pyrrolidinone, 1-ethenyl-

2-Pyrrolidinone, 1-ethenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Pyrrolidinone, 1-ethenyl- 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: 26-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15035

Polyvinylpyrrolidone: Does not have an individual approval but may be used under an appropriate group standard

Vinylpyrrolidone: Does not have an individual approval but may be used under an appropriate group standard

PEC / SN / Other assessments - N-vinyl-2-pyrrolidone (NVP): Health and Environment

IMAP assessments - Poly[1-(2-oxo-1-pyrrolidinyl)-1,2-ethanediyl]: Human health tier I assessment

No health effects found in a study of 94 production workers; Animal studies show evidence of liver damage in acute and chronic studies; [ACGIH] An eye and respiratory tract irritant; May cause liver injury; [ICSC] See N-Methyl-2-pyrrolidone.

European Union/European Chemicals Bureau; Risk Assessment Report: 1-Vinyl-2-pyrrolidone (88-12-0) V39 (2003).

NICNAS; Priority existing chemical assessment report on N-vinyl-2-pyrrolidone (NVP) 11: 134 (2000)

Acute Tox. 4 (97.2%)

Carcinogenicity - category 2

Acute toxicity (Oral) - Category 4

Acute toxicity (Oral) - Category 4

Acute toxicity (Oral) - Category 4

Carc. 2

Explosion limits in air: 1.4-10.0 Vol. %

Explosive limits , vol% in air: 1.4-10

Heat develops during polymerization when mixed with acids.

Can react vigorously with oxidizing materials...

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

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

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Ventilation. 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.

LC50 Salmo gairdneri/ renamed Oncorhyncus mykiss (Rainbow trout) 913 mg/L/96 hr; static

LC50 Salmo gairdneri/ renamed Oncorhyncus mykiss (Rainbow trout) 976 mg/L/72 hr; static

EC50 Daphnia magna (immobilization) 130 mg/L/24 hr; 45 mg/L/48 hr /Conditions of bioassay not specified in source examined/

EC50 Scenedesmus subscpicatus (Algae; biomass) 780 mg/L/72 hr /Conditions of bioassay not specified in source examined/

EC50 Scenedesmus subscpicatus (Algae; growth rate) >1000 mg/L/72 hr /Conditions of bioassay not specified in source examined/

/AQUATIC SPECIES/ Four groups of five animals /(Daphnia magna)/ were used at each dose level of 0.7, 1.6, 3.8, 8.0, 17.9, 40.0, 89.4, 200.0, 447.0 and 1,000 mg/L. Only one control group was used. An EC50 of 45.04 mg/L and a NOEC of 3.6 mg/L after 48 hours were derived from the results. An EC100 of 447 mg/L after 48 hours was also reported.

Cough. Sore throat.

Redness. Pain. Severe deep burns.

Abdominal pain. Diarrhoea. Nausea. Vomiting.

/HUMAN EXPOSURE STUDIES/ Only one study has been conducted to examine the health of N-VP production workers, a cross-sectional morbidity study. The study included comprehensive medical examinations of the majority of the workforce and no signs of ill health related to N-VP exposure were identified. However, the actual levels of N-VP to which the workforce was exposed are unclear.

/OTHER TOXICITY INFORMATION/ In liver biopsies from people who had received polyvinyl pyrrolidone iv, basophilic globular deposits were observed in Kupffer cells, occasionally accompanied by mild inflammation. Thesaurismosis (a foam-cell storage phenomenon characterized by swollen cells with reticulated nuclei loaded with vacuoles or deposits of polyvinyl pyrrolidone) has been observed after inhalation of hair sprays containing polyvinyl pyrrolidone and may be accompanied by pulmonary fibrosis and pneumonia. /Polyvinyl pyrrolidone/

N-Vinyl-2-pyrrolidone

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 19: (1979) Some Monomers, Plastics and Synthetic Elastomers, and Acrolein

1999

1998

/LABORATORY ANIMALS: Acute Exposure/ A 4-hr LC50 value of 3,070 mg/cu m (3.07 mg/L) has been obtained from a study in which groups of 10 male and 10 female Sprague-Dawley rats were exposed head only to aerosols of around 800, 2,000, 2,800, 5,200 or 5,600 mg/cu m N-VP (purity >99%, stabilized with 10 ppm Kerobit, particle size not stated). Following exposure, rats were observed for 14 days and underwent gross necropsy at the end of the study. Deaths occurred in all but the lowest dose group within 2-4 days of exposure, and clinical signs of toxicity including increased respiration rates, ataxia, /CNS depression/, bloodshot eyes and nasal secretions were observed in all dose groups. Necropsy revealed changes in decedents only. In the lungs, isolated areas of edema were recorded; in the heart, acute hyperemic obstruction and acute dilation of the fore chambers occurred; the liver had a sandy grey appearance; multiple bloody ulcerations were apparent in the stomach and blood was apparent in intestinal contents suggesting irritation of the gastrointestinal tract. There was also some discoloration of the kidneys. No details on the severity of these changes were provided. No deaths occurred in earlier studies in which cats, rabbits, guinea pigs, rats and mice or rats alone were exposed for 6 or 8 hr to air saturated with N-VP vapor. Signs of toxicity during exposure were limited to salivation and nasal secretion, and at necropsy, slight irritation of the mucous membranes was occasionally observed. Based on the reported vapor pressure of 0.12 hPa, the saturated vapor concentration would be 0.6 mg/L (600 mg/cu m).

/LABORATORY ANIMALS: Acute Exposure/ A dermal LD50 value of 560 mg/kg has been estimated from a study in which groups of 5 rabbits were given 200, 375, 800, 1,000 or 2,000 mg/kg on intact skin. The conditions of exposure were not stated. Deaths occurred in all but the lowest dose group within 5 days of dosing and all animals in the top two groups died. No information on local skin effects or systemic toxicity was provided.

/LABORATORY ANIMALS: Acute Exposure/ Results from a study in the rat indicated that the dermal LD50 value for this species lay between 1,043 and 4,127 mg/kg. Groups of 2 male and 2 female CFY rats were given 0, 668, 1,043, 4,127 or 10,430 mg/kg N-VP over an area approximately 10% of body surface under an occlusive dressing for 24 hr. There was no evidence of irritation at the site of application. Deaths occurred in all but the low dose group within three days of dosing and non-specific signs of toxicity were seen in all rats given 1,043 mg/kg or more. Signs of toxicity in the lowest dose group were limited to slight diarrhea in the two males. Autopsy of decedents revealed congestion of the lungs, pallor of the liver, kidneys and spleen and injection of the blood vessels into the subcutaneous tissue at the site of application. Body weight gains of treated rats were reduced during the first week of observation but were normal during the second week. No abnormalities were seen in survivors at necropsy.

/LABORATORY ANIMALS: Acute Exposure/ The effects of single oral gavage doses of N-VP ... in aqueous solution have also been studied in guinea pigs, cats and rabbits. One out of a group of 4 guinea pigs given 520 mg/kg, died. All animals showed a lack of appetite, apathy, slight atony and one developed enteritis after 3 days. Groups of 3 rabbits received 417 or 1,043 mg/kg. No deaths occurred. At both dose levels, slight weight loss and lack of appetite were recorded. Groups of two cats received 100, 210 or 520 mg/kg N-VP. One top dose cat died 3 days after dosing. Salivation and emesis were apparent at all dose levels, accompanied by a lack of appetite, slight weight loss and loss of balance at the top dose level, which persisted until the surviving cat was sacrificed 28 days post exposure.

For more Non-Human Toxicity Excerpts (Complete) data for 2-PYRROLIDINONE,1-ETHENYL- (38 total), please visit the HSDB record page.

Evaluation: No epidemiological data relevant to the carcinogenicity of N-vinyl-2-pyrrolidone ... were available. There is limited evidence for the carcinogenicity of N-vinyl-2-pyrrolidone in experimental animals. Overall evaluation N-Vinyl-2-pyrrolidone is not classifiable as to its carcinogenicity to humans (Group 3).

A3; Confirmed animal carcinogen with unknown relevance to humans.

LD50 Rat oral 1470 mg/kg

LD50 Rabbit dermal 560 mg/kg

LD50 Mouse oral about 940 mg/kg bw

LC50 Rat inhalation 3.07 mg/L/4 hr

For more Non-Human Toxicity Values (Complete) data for 2-PYRROLIDINONE,1-ETHENYL- (9 total), please visit the HSDB record page.

The disposition of N-[14C]-vinyl-2-pyrrolidone has been studied in male Sprague-Dawley rats following a single iv injection. The plasma half-life was 1.9 hr.

...The hydrolysis of /N-vinylpyrrolidone/ (N-VP) at 37 °C and pHs ranging from 1.2-7.2 /was studied/. ...The rate of hydrolysis was inversely related to pH such that at a pH of 1.2 the half-life of N-VP in aqueous solution was only around 1.5 min; at pHs ranging from 2.2-2.5, half-lives of 20-40 min were observed; at a pH of 3.5, the half-life had risen to over 6 hr and at a pH of 7.2, N-VP was stable in aqueous solution for at least 24 hr.

/N-Vinylpyrrolidone/ (N-VP) in aqueous solution was also administered by naso-gastric tube to 3 fasted dogs at successive dose levels of 5, 10 and 20 mg/kg and non-fasted dogs (fasted overnight then allowed a meal 30 min before dosing) at 20 mg/kg. ...Elimination from plasma followed an exponential pattern, with half-lives ranging between 0.3 and 0.6 hr, and was independent of dose.

...Anesthetized rats were given 14C(vinyl)-N-VP in aqueous solution via the jugular vein. ... Elimination from the blood followed a biphasic pattern and half-lives for the slow phase of around 1.5-1.9 hr were calculated. These half-life values are somewhat higher than those calculated in the previous oral and other iv studies.

...The hydrolysis of /N-vinylpyrrolidone/ (N-VP) at 37 °C and pHs ranging from 1.2-7.2 /was studied/. ...The major hydrolysis products, accounting for around 95% of hydrolysed N-VP, were identified as 2-pyrrolidone and acetaldehyde (in hydrated form) with acetaldehyde-hemihydrate accounting for the remaining 5%.

The ability of N-VP to bind to plasma proteins or microsomal proteins in vitro has been briefly investigated. At most, 12% of N-VP or its metabolites were bound to proteins, lending further weight to the conclusion that N-VP is not metabolized to an alkylating species.

The disposition of N-[14C]-vinyl-2-pyrrolidone has been studied in male Sprague-Dawley rats following a single iv injection. ...Up to 6 hr after dosing, the highest tissue concentrations of radioactivity were found in the liver and small intestines. By that time, about 19% of the dose had been excreted in bile, yet, by 12 hr, only about 0.4% had been excreted in feces while about 75% had been excreted in urine. Thus, there appeared to be substantial enterohepatic recirculation of biliary metabolites. Very small quantities of the administered material were excreted unchanged. In a single rat, 12% of the urinary radioactivity was present as acetic acid. Other metabolites were not identified.

Following ingestion /1-vinyl-2-pyrrolidinone/ is mainly distributed in the liver and small intestine. It is partially excreted in the urine in an acetate form, but it is mostly (88%) combined with water-soluble acid compounds. Following iv injection, 14C-1-vinyl-2-pyrrolidinone was cleared from the blood with a half-life of about 2 hr. Unchanged /1-vinyl-2-pyrrolidinone/ accounted for <0.6% of the dose administered.

The disposition of N-[14C-vinyl]-2-pyrrolidinone was studied in male Sprague-Dawley rats following a single iv injection. Plasma levels of the intact compound dropped rapidly within the first 6 hours after dosing... . Urinary excretion by 12 hours represented 74.9% of a 5 microCi dose while 18.7% was excreted into the bile by 6 hours. 14C-activity attributed to the intact compound was found to be <0.59% of the dose in the urine and <0.46% in the bile. Tissue distribution studies showed that the liver and small intestines and contents contained the highest accumulation of 14C-activity up to 6 hours after administration of N-[14C-vinyl]-2-pyrrolidinone. Urine analyses performed for metabolite elucidation indicated that 12% of the radioactivity dosed was incorporated into acetate and the major remaining portion in species which appeared to be water soluble acidic compounds.

The toxic effects of vinylpyrrolidone /and/ vinylacetate (VP-VA) were examined in rats. Female Wistar-rats, under ether narcosis, were given endotracheally 0.5 mL of a standard solution of VP-VA (10 g in 15 mL of physiological sodium-chloride solution). Other rats received up to 7 times the 2 mL standard solution daily under the skin of the back; between 1.1 and 45.0 g/kg VP-VA were injected. The animals were sacrificed between 1 and 365 days following the application of the VP-VA solution. Tissues were stained and examined by electron microscopy. One to 2 days after endotracheal injection, the alveoli were closely packed with macrophages. Four to 6 months after the last injection, there was still VP-VA in the lungs with the attendent macrophages. Animals killed 1 yr after the last injection showed no VP-VA in the lungs. After sc injection, most of the VP-VA was stored in the spleen. There were occasional, large macrophages found in the interstitial tissue of the lung. During the 1 yr period of observation, there was no evidence of tumors or systemic disease. ...

For more Absorption, Distribution and Excretion (Complete) data for 2-PYRROLIDINONE,1-ETHENYL- (11 total), please visit the HSDB record page.

Used as a monomer in the production of polyvinyl pyrrolidone; also used in the production of other polymers and organic chemicals; [ACGIH]

Using Disinfectants or Biocides [Category: Clean]

Used to manufacture water-soluble and insoluble forms of polyvinyl pyrrolidone for pharmaceutical and cosmetic industries and to make copolymers with other monomers intended for use in contact with food. ...Used in cast films adherent to glass, metals, plastics.

Solvent for resins, co-monomer for polymerization, binder in cosmetic and pharmaceutical preparations.

...About 10-15% of the monomer is used in the pharmaceutical industry for the production of PVP-iodine complex used as a disinfectant. It is also used as a reactive solvent of UV-curable resins for the production of printing inks and paints as paper and textile auxiliaries, and as an additive in the cosmetics industry.

... Precursor and intermediate for process auxiliaries and additives. The main areas of use are the production of polyvinylpyrrolidone and copolymers, the preferred comonomers being vinyl acetate and methyl acrylate.

Industrially, NVP is produced by reacting 2-pyrrolidone with acetylene in high-pressure autoclaves at 130-160 °C and pressures of up to 2.6 MPa. Vinylation proceeds in the liquid phase and is catalyzed by 2-pyrrolidone-potassium, which is obtained by dissolving 1-5% potassium hydroxide (the water formed is removed by distillation in vacuo) or potassium in 2-pyrrolidone. To avoid the danger of explosions acetylene-nitrogen mixtures are used instead of acetylene. The crude product obtained by continuous or batch production is purified by vacuum distillation.

A typical commercial product has the following composition: NVP content, minimum 99 weight percent; 2-pyrrolidone, maximum 0.2 weight percent; water, maximum 0.1 weight percent; color index (freshly filled, APHA), 40 maximum; stabilizers: 10 ppm N,N'-bis(1-methylpropyl)-1,4-benzenediamine or 0.1 weight percent sodium hydroxide.

Polyquaternium-11 is a copolymer of vinylpyrrolidone and dimethylamine ethylmethacrylate, partially quaternized with diethyl sulfate....Industry specifications for Polyquaternium-11 allow residual vinylpyrrolidone to a maximum concentration of 1.0%. ...The principal use of Polyquaternium-11 in cosmetic products is in hair care preparations.

Polyvinylpyrrolidone/Vinyl Acetate Copolymer (PVP/VA Copolymer) is the copolymer of vinyl pyrrolidone (VP) and vinyl acetate (VA) monomers. The copolymers vary in their ratio of VP to VA and range from 70:30 to 30:70 VP to VA.

Printing Ink Manufacturing

2-Pyrrolidinone, 1-ethenyl-: ACTIVE

PVP/VA Copolymer is used in tablet coating, spray bandages, protective masks, spray or rub-on gloves, plant leaf sprays, shoe polishes, and film production; it is also used as a dye medium in adhesive sticks and in the synthesis of peptides.