Appearance:liquid
Purity:99%
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
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.
Uses
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
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).
The vinylation of various nucleophiles with acetylene at a maximum pressure of 1.5 bar is achieved by organocatalysis with easily accessible phosphines like tri-n-butylphosphine. A detailed mechanistic investigation by quantum-chemical and experimental methods supports a nucleophilic activation of acetylene by the phosphine catalyst. At 140 °C and typically 5 mol % catalyst loading, cyclic amides, oxazolidinones, ureas, unsaturated cyclic amines, and alcohols were successfully vinylated. Furthermore, the in situ generation of a vinyl phosphonium species can also be utilized in Wittig-type functionalization of aldehydes.
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.
The production of monomers from bio-based platform chemicals shows great potential to reduce the chemical industry's demand for fossil resources. We herein present a two-step approach, which yields N-vinyl-2-pyrrolidone monomers from bio-based carboxylic acids, such as itaconic and levulinic acid. A highly active, heterogeneous palladium catalyst facilitating the reductive amidation of itaconic acid (TOF = 950 molPyr·molPd-surface-1 h-1) as well as the reductive amination of levulinic acid (TOF = 4000 molPyr·molPd-surface-1 h-1) was designed. Especially the reductive amidation of itaconic acid to 3- and 4-methyl-2-pyrrolidone was found to be structure sensitive. A clear trend between Pd particle size and catalyst activity could be shown by the synthesis of Pd/C catalysts with varying Pd particle sizes. The vinylation of the synthesized methyl-2-pyrrolidones with acetylene was tested using common industrial conditions (10-18 bar acetylene, 150 °C, KOH catalyst, no solvent). Similar to the industrial vinylation of 2-pyrrolidone, good yields of up to 80% N-vinyl-methyl-2-pyrrolidone were received. Therefore, and due to the excellent maximum yield of methyl-2-pyrrolidones in reductive amidation (95 mol%), the envisioned process can be a promising drop-in technology, directly replacing fossil resources in the production of an established monomer class. This journal is
1-(2-hydroxyethyl)-2-pyrrolidinone
1-ethenyl-2-pyrrolidinone
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With Na/SiO2; ammonia; at 350 ℃; for 10h; under 750.075 Torr; Reagent/catalyst; Temperature; Catalytic behavior;
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90% |
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Ca/Zn oxide; at 348 ℃; for 1h;
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82% |
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Ca/Zn oxide; at 331 - 359 ℃; for 1h;
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67.5% |
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zinc-magnesium mixed oxide; at 356 - 360 ℃; for 2 - 4h;
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66.7% |
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Ca/Zn oxide calcined in air to 500 C; at 366 ℃; for 1h;
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44% |
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magnesium oxide; at 368 ℃; for 1h;
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26.6% |
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Ca/Zn oxide calcined in air to 700 C; at 359 ℃; for 1h;
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11.5% |
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calcium carbonate; at 377 ℃; for 1h;
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2.7% |
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With aluminum oxide; at 300 - 340 ℃; under 56 Torr; Beim Leiten des Dampfes von Edukt ueber Reagens;
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Multi-step reaction with 2 steps
1: benzene; thionyl chloride
2: benzene; sodium amide
With thionyl chloride; sodium amide; benzene;
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Product distribution / selectivity;
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With Cs2O#SiO2; at 500 ℃; for 2h;
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Gas phase;
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With Cs1Si10 catalyst; for 1h; under 760.051 Torr; Inert atmosphere; Sealed tube;
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87 %Chromat. |
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With sodium oxide-silicon dioxide; at 350 ℃; Temperature; Catalytic behavior; Flow reactor; Green chemistry;
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2-pyrrolidinon
![[1,3]-dioxolan-2-one](/upload/2023/2/478037b5-e0b4-4c5d-91aa-935996ab425f.png)
[1,3]-dioxolan-2-one
1-ethenyl-2-pyrrolidinone
| Conditions | Yield |
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With TEMPOL; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 5,5-dimethyl-1,3-cyclohexadiene; at 100 - 120 ℃; for 3.5h; Dean-Stark;
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82.13% |
2-pyrrolidinon
1-(2-chloro-ethyl)-pyrrolidin-2-one
1-(2-hydroxyethyl)-2-pyrrolidinone
N-trimethylsilyl-pyrrolidin-2-one
{2-(2-oxo-N-pyrrolidinyl)ethyl}triphenyltin
3-benzoyl-N-vinylpyrrolidin-2-one
1-(1-Methoxyethyl)-2-pyrrolidinon
1-(pyrrolidinyl-2-on-1-yl)-1-triethylsilylethane
