88-12-0

Basic information

• Product Name: N-Vinyl-2-pyrrolidone
• Synonyms: N-VINYL-2-PYRROLIDINONE;N-VINYL-2-PYRROLIDONE;N-VINYLPYRROLIDONE;N-VINYLBUTYROLACTAM;1-ethenyl-2-pyrrolidinon;1-Ethenyl-2-pyrrolidinone;1-vinyl-2-pyrrolidinon;1-Vinyl-2-pyrrolidinone, monomer
• CAS NO: 88-12-0
• Molecular Formula: C₆H₉NO
• Molecular Weight: 111.14
• EINECS: 201-800-4
• Product Categories: monomer
• Mol File: 88-12-0.mol
• Article Data: 38

Chemical Properties

• Melting Point: 13-14 °C
• Boiling Point: 92-95 °C11 mm Hg(lit.)
• Flash Point: 201 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.04 g/mL at 25 °C(lit.)
• Vapor Density: 3.8 (vs air)
• Vapor Pressure: 0.1 mm Hg ( 24 °C)
• Refractive Index: n20/D 1.512(lit.)
• Storage Temp.: 0-6°C
• Solubility: 52.1g/l soluble
• PKA: -0.34±0.20(Predicted)
• Explosive Limit: 1.4-10%(V)
• Water Solubility: miscible
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,7697
• BRN: 110513
• CAS DataBase Reference: N-Vinyl-2-pyrrolidone(CAS DataBase Reference)
• NIST Chemistry Reference: N-Vinyl-2-pyrrolidone(88-12-0)
• EPA Substance Registry System: N-Vinyl-2-pyrrolidone(88-12-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-37-40-41-48/20
• Safety Statements: 26-36/37/39
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 1
• RTECS: UY6107000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 88-12-0(Hazardous Substances Data)

Usage

Description

N-vinyl-2-pyrrolidone (NVP) is commonly used as a reactive diluent for radiation curing in UV-coating, UV-inks, and UV adhesives. It is used as a monomer to produce water soluble polyvinylpyrrolidone (PVP) with uses in pharmaceuticals, oil field, cosmetics, food additives & adhesives. It is used in the manufacture of copolymers with, for example, acrylic acid, acrylates, vinyl acetate and acrylonitrile and in the synthesis of phenolic resins.

Chemical Properties

Colorless liquid. Combustible.

Uses

Different sources of media describe the Uses of 88-12-0 differently. You can refer to the following data:
1. 1-Vinyl-2-pyrrolidinone is used in the preparation of NMDA receptor antagonists. Also used in the synthesis of copolymers used to stabilize rhodium nanoclusters.
2. A pyrrolidine used for biochemical research

General Description

1-Vinyl-2-pyrrolidinone is a colorless to yellow liquid, with a characteristic odor. Its melting point is around 13.5oC and boils at about 90-92oC. VP is completely miscible in water and in most organic solvents but partially miscible in aliphatic hydrocarbons. Industrial production of VP by reacting 2-pyrrolidone with acetylene at high pressure and temperature has been reported. The vinylation process proceeds in liquid phase and is catalyzed by 3-pyrrolidone -potassium hydroxide.

Safety Profile

Confirmed carcinogen. Moderately toxic by ingestion, inhalation, and skin contact. A severe eye irritant. Probably irritating and narcotic in high concentrations. Combustible when exposed to heat or flame; can react vigorously with oxibzing materials. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits highly toxic fumes of NOx.

InChI:InChI=1/C6H9NO/c1-2-7-5-3-4-6(7)8/h2H,1,3-5H2

Upstream product

• 3445-11-2 1-(2-hydroxyethyl)-2-pyrrolidinone 
• 616-45-5 2-pyrrolidinon 
• 74-86-2 acetylene 
• 18190-44-8 1-(2-Hydroxy-ethyl)-pyrrolidine-2,5-dione 
• 96-49-1 [1,3]-dioxolan-2-one 
• 75-07-0 acetaldehyde 
• 6908-59-4 N-(α-ethoxyethyl)-2-pyrrolidone 
• 105-08-8 bis-1,4-(hydroxymethyl)cyclohexane 
• 107-21-1 ethylene glycol 
• 111-34-2 -butyl vinyl ether 
• 151455-45-7 Acetic acid 2,2-dichloro-1-(2-oxo-pyrrolidin-1-yl)-ethyl ester 
• 14468-90-7 N-trimethylsilyl-pyrrolidin-2-one 
• 7081-78-9 1-chloroethyl ethyl ether 
• 51333-90-5 1-(2-chloro-ethyl)-pyrrolidin-2-one 

Downstream Products

• 4593-27-5 apoferrorosamine 
• 66269-78-1 4-(3,4-dihydro-2H-pyrrol-5-yl)pyridine 
• 221374-82-9 5-cyclohexenyl-3,4-dihydro-2H-pyrrole 
• 2687-91-4 1-ethyl-2-pyrrolidinone 
• 104-09-6 4-methylphenylacetaldehyde 
• 122-00-9 para-methylacetophenone 
• 750634-65-2 N-(1-[4-methylphenyl]ethenyl)-2-pyrrolidinone 
• 99-91-2 para-chloroacetophenone 
• 1009-61-6 1,4-Diacetylbenzene 

Relevant articles and documents

SYNTHESIS OF N-VINYL COMPOUNDS BY REACTING CYLIC NH-COMPOUNDS WITH ACETYLENE IN PRESENCE OF HOMOGENOUS CATALYST

Process to produce N-vinyl compounds by homogeneous catalysis, wherein acetylene is reacted with a cyclic compound comprising a cyclic compound having at least one nitrogen as ring member, bearing a substitutable hydrogen residue (cyclic compound C), in a liquid phase in the presence of a ruthenium complex comprising at least one phosphine as ligand (RuCat).

Ruthenium-catalyzed synthesis of vinylamides at low acetylene pressure

The reaction of cyclic amides with acetylene under low pressure, using ruthenium-phosphine catalysts, afforded a broad variety ofN-vinylated amides including (azabicyclic) lactams, oxazolidinones, benzoisoxazolones, isoindolinones, quinoxalinones, oxazinanones, cyclic urea derivatives (imidazolidinones), nucleobases (thymine), amino acid anhydrides and thiazolidinone.

Extending the chemical product tree: A novel value chain for the production of: N -vinyl-2-pyrrolidones from biogenic acids

The sustainable production of polymers from biogenic platform chemicals shows great promise to reduce the chemical industry's dependence on fossil resources. In this context, we propose a new two-step process leading from dicarboxylic acids, such as succinic and itaconic acid, to N-vinyl-2-pyrrolidone monomers. Firstly, the biogenic acid is reacted with ethanolamine and hydrogen using small amounts of water as solvent together with solid catalysts. For effective conversion, the optimal catalyst (carbon supported ruthenium) has to hold the ability of activating H2 as well as (imide) CO bonds. The obtained products, N-(2-hydroxyethyl)-2-pyrrolidones, are subsequently converted in a continuous gas phase dehydration over simple sodium-doped silica, with excellent selectivity of above 96 mol% and water as the sole by-product. With a final product yield of ≥72 mol% over two process steps and very little waste due to the use of heterogeneous catalysis, the proposed route appears promising-commercially as well as in terms of Green Chemistry.