N-vinyl-2-pyrrolidone

PVPP · POLYVINYLPOLYPYRROLIDONE · PLASDONE · Polyplasdone · POLYVINYLPYRROLIDONE K 90 · K-30 · POLYVIDONE · POLYVIDONUM

Identifiers & Physical Properties

CAS No.	25249-54-1
Molecular formula	C6H9NO
Average molar mass	111.14 g/mol
Monoisotopic mass	111.06841391 g/mol
SMILES	C=CN1CCCC1=O
InChIKey	WHNWPMSKXPGLAX-UHFFFAOYSA-N
PubChem CID	6917
ChEMBL	CHEMBL1878943
ChEBI	CHEBI:82551
EC No.	201-800-4
DTXSID	DTXSID2021440

Chemical & Physical Properties

XLogP	0.4
Topological polar surface area	20.3
Hydrogen bond donors	0
Hydrogen bond acceptors	1
Rotatable bonds	1
Heavy atoms	8
Formal charge	0
Complexity	120
Drugs	Pharmaceuticals
Polymers	Plastics & Rubber -> Other Monomers
Cosmetics	Emulsion stabilizingAntistaticBindingFilm formingHair fixing
SpringerMaterials Properties	Chemical shift
LogP (partition coefficient)	log Kow = 0.370.4
Food additives	PROCESSING AID, SURFACE-FINISHING AGENT -> FDA Substance added to food
Density	1.04 @ 24 °C/4 °CRelative density (water = 1): 1.041..041.04 @25 °C
Viscosity	2.07 cps @ 25 °C2.07 cP at 25 °C
Color/Form	Clear to light straw colored liquid
Solubility	Soluble in water and many organic solventsIn water, 5.2X10+4 mg/L @ 25 °C /Estimated/Solubility in water: very goodInsoluble in water, acid and alkaline.
Flash point	95 °C100.5 °C (213 °F) open cup95 °C closed cup93 °C199.4 °F
Boiling point	96 °C @ 14 mm Hg193 °C @ 400 mm Hgat 1.3kPa: 90-93 °C194 °F
Melting point	~165 °C (dec.)(lit.)
Physical state	powder
Color	White to off-white
InChI	InChI=1S/C6H9NO/c1-2-7-5-3-4-6(7)8/h2H,1,3-5H2
InChIKey	WHNWPMSKXPGLAX-UHFFFAOYSA-N
SMILES	N1(C=C)CCCC1=O
FDA 21 CFR	173.50
CAS DataBase Reference	25249-54-1
EWG's Food Scores	1
Cosmetics Info	PVP
UNSPSC Code	12352100
NACRES	NA.23
Safety statements (S)	22-24/25
Water hazard class (WGK)	1
RTECS number	TR8370000
Customs code	39059900
Storage class	11 - Combustible Solids

Safety & Regulations

GHS classification	DangerH302: 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.H302 (97.2%): Harmful if swallowed [Warning Acute toxicity, oral]
Regulatory information	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/15035Polyvinylpyrrolidone: Does not have an individual approval but may be used under an appropriate group standardVinylpyrrolidone: Does not have an individual approval but may be used under an appropriate group standard
Other safety information	PEC / SN / Other assessments - N-vinyl-2-pyrrolidone (NVP): Health and EnvironmentIMAP assessments - Poly[1-(2-oxo-1-pyrrolidinyl)-1,2-ethanediyl]: Human health tier I assessment
Fire hazards	Combustible.
Hazards summary	No health effects found in a study of 94 production workersAnimal studies show evidence of liver damage in acute and chronic studies[ACGIH] An eye and respiratory tract irritantMay cause liver injury[ICSC] See N-Methyl-2-pyrrolidone.
EC classification	Symbol: XnR: 20/21/22-37-40-41-48/20S: 26-36/37/39Note: D
Special Reports	European Union/European Chemicals BureauRisk Assessment Report: 1-Vinyl-2-pyrrolidone (88-12-0) V39 (2003).NICNASPriority existing chemical assessment report on N-vinyl-2-pyrrolidone (NVP) 11: 134 (2000)
Chemical Dangers	The substance may polymerize in the presence of air due to warming, under the influence of light and acids. Decomposes on burning. This produces toxic and corrosive gases of nitrogen oxides.
Hazard Classes and Categories	Acute Tox. 4 (97.2%)Carcinogenicity - category 2Acute toxicity (Oral) - Category 4Carc. 2
Explosive Limits and Potential	Explosion limits in air: 1.4-10.0 Vol. %Explosive limits , vol% in air: 1.4-10
Hazardous Reactivities and Incompatibilities	Heat develops during polymerization when mixed with acids.Can react vigorously with oxidizing materials...
Fire fighting	Use water spray, powder, foam, carbon dioxide.
First aid measures	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 .
Safe storage	Separated from strong acids. Keep in the dark. Cool. Store only if stabilized.
Exposure control and personal protection	0.01 [ppm]
Fire fighting procedures	To fight fire use alcohol foam, carbon dioxide or dry chemical.
Disposal methods	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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.
Spillage disposal	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.
Eye Prevention	Wear safety goggles or eye protection in combination with breathing protection.
Fire Prevention	NO open flames.
Inhalation Risk	A harmful contamination of the air will be reached quickly on evaporation of this substance at 20 °C.
Skin Prevention	Protective gloves.
Exposure Prevention	STRICT HYGIENE!
Ecotoxicity values	LC50 Salmo gairdneri/ renamed Oncorhyncus mykiss (Rainbow trout) 913 mg/L/96 hrstaticLC50 Salmo gairdneri/ renamed Oncorhyncus mykiss (Rainbow trout) 976 mg/L/72 hrEC50 Daphnia magna (immobilization) 130 mg/L/24 hr45 mg/L/48 hr /Conditions of bioassay not specified in source examined/EC50 Scenedesmus subscpicatus (Algaebiomass) 780 mg/L/72 hr /Conditions of bioassay not specified in source examined/growth rate) >1000 mg/L/72 hr /Conditions of bioassay not specified in source examined/
Adverse effects	Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure routes	The substance can be absorbed into the body by inhalation, through the skin and by ingestion.
Ecotoxicity excerpts	/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.
Signs and Symptoms	Cough. Sore throat.Redness. Pain. Severe deep burns.Abdominal pain. Diarrhoea. Nausea. Vomiting.
Human Toxicity Excerpts	/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/
Carcinogen Classification	N-Vinyl-2-pyrrolidoneGroup 3: Not classifiable as to its carcinogenicity to humansVolume 19: (1979) Some Monomers, Plastics and Synthetic Elastomers, and Acrolein19991998
Non-Human Toxicity Excerpts	/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 recordedin the heart, acute hyperemic obstruction and acute dilation of the fore chambers occurredthe liver had a sandy grey appearancemultiple 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.
Evidence for Carcinogenicity	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).A3Confirmed animal carcinogen with unknown relevance to humans.
Toxicity Data	LC50 (rat) = 3,200 mg/m3/4h
Non-Human Toxicity Values	LD50 Rat oral 1470 mg/kgLD50 Rabbit dermal 560 mg/kgLD50 Mouse oral about 940 mg/kg bwLC50 Rat inhalation 3.07 mg/L/4 hrFor more Non-Human Toxicity Values (Complete) data for 2-PYRROLIDINONE,1-ETHENYL- (9 total), please visit the HSDB record page.
Water hazard class (WGK)	1
RTECS number	TR8370000
Customs code	39059900
Safety statements (S)	22-24/25
Storage class	11 - Combustible Solids

Applications & Uses

Uses

PVP (polyvinylpyrrolidone) is a chemical ingredient that, depending on the formulatory requirement, can act as a binder, viscosity controller, emulsion stabilizer, or film former. Its benefits include water and wear resistance, pigment dispersion, a non-greasy feel, and improved stick integrity. PVP is commonly found in waterproof sunscreens, mascaras, and lipsticks in order to improve their wear.

Uses

Polyvinylpyrrolidone (PVP) has been used as a clarifying agent in the food industry.

Uses

Polyvinylpyrrolidone is used in coatings, printing ink, rubber, glass, leather, cosmetics, soaps, plastics, in paper making and as a stabilizer. It acts as a disintegrant in pharmaceutical tablets and as a fining to extract impurities. It is used to remove polyphenols in beer.