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N-Methyl-2-pyrrolidone is an aprotic solvent with a wide range of applications: petrochemical processing, surface coating, dyes and pigments, industrial and domestic cleaning compounds, and agricultural and pharmaceutical formulations.
N-Methyl-2-pyrrolidone is mainly an irritant, but has also caused several cases of contact dermatitis in a small electrotechnical company.
N-Methyl-2-pyrrolidone is a member of the class of pyrrolidine-2-ones that is pyrrolidin-2-one in which the hydrogen attached to the nitrogen is replaced by a methyl group.
CAS: 872-50-4
MF: C5H9NO
MW: 99.13
EINECS: 212-828-1
Synonyms
M-PYROL(R);1-Methyl-2-pyrrolidinone( 99.5%, HyDry, Water≤50 ppm (by K.F.));1-Methyl-2-pyrrolidinone( 99.5%, HyDry, with molecular sieves, Water≤50 ppm (by K.F.));N-Methyl-2-pyrrolidone Manufacturer;1-METHYL-2-PYRROLIDONE, REAGENT (ACS)1-METHYL-2-PYRROLIDONE, REAGENT (ACS)1-METHYL-2-PYRROLIDONE, REAGENT (ACS);1-Methyl-2-pyrrolidinone 872-50-4 NMP N-Methyl-2-pyrrolidinone;N-Methyl-2-pyrrolidinone 872-50-4 NMP;1-METHYL-2-PYRROLIDINONE
N-Methyl-2-pyrrolidone has a role as a polar aprotic solvent.
N-Methyl-2-pyrrolidone is a N-alkylpyrrolidine, a lactam and a member of pyrrolidin-2-ones.
N-Methyl-2-pyrrolidone is an organic compound consisting of a 5-membered lactam.
N-Methyl-2-pyrrolidone is a colorless liquid, although impure samples can appear yellow.
N-Methyl-2-pyrrolidone is miscible with water and with most common organic solvents.
N-Methyl-2-pyrrolidone also belongs to the class of dipolar aprotic solvents such as dimethylformamide and dimethyl sulfoxide.
N-Methyl-2-pyrrolidone is used in the petrochemical, polymer and battery industries as a solvent, exploiting its nonvolatility and ability to dissolve diverse materials (including polyvinylidene difluoride, PVDF).
N-Methyl-2-pyrrolidone has a strong dipole moment and hydrogen bonding due to its cis-amide conformation.
N-Methyl-2-pyrrolidone is a solvent that is used in the production of polymers, paints, and other products.
N-Methyl-2-pyrrolidone has been shown to be a potent inducer of cardiac arrhythmias in rats.
N-Methyl-2-pyrrolidone also has been shown to have a linear calibration curve for electrochemical impedance spectroscopy (EIS) data from 0.1 M to 5 M.
This property makes N-Methyl-2-pyrrolidone useful for determining reaction mechanisms and surface methodology.
N-Methyl-2-pyrrolidone has been shown to have constant pressure experimental solubility data, which can be used for thermodynamic data and high resistance values.
N-Methyl-2-pyrrolidone is not toxic to humans or animals at concentrations up to 2000 mg/kg body weight, but it does cause congestive heart failure in rats at doses of 500 mg/kg body weight or higher.
N-Methyl-2-pyrrolidone Chemical Properties
Melting point: -24 °C (lit.)
Boiling point: 202 °C (lit.) 81-82 °C/10 mmHg (lit.)
Density: 1.028 g/mL at 25 °C (lit.)
Vapor density: 3.4 (vs air)
Vapor pressure: 0.29 mm Hg ( 20 °C)
Refractive index: n20/D 1.479
Fp: 187 °F
Storage temp.: Store at +5°C to +30°C.
Solubility ethanol: miscible0.1ML/mL, clear, colorless (10%, v/v)
Form: Liquid
pka: -0.41±0.20(Predicted)
Color: ≤20(APHA)
PH: 8.5-10.0 (100g/l, H2O, 20℃)
Odor: Slight amine odor
PH Range: 7.7 - 8.0E
Explosive limit: 1.3-9.5%(V)
Water Solubility: >=10 g/100 mL at 20 ºC
Sensitive: Hygroscopic
λmax: 283nm(MeOH)(lit.)
Merck: 14,6117
BRN: 106420
Dielectric constant: 32.200000000000003
Stability: Stable, but decomposes upon exposure to light. Combustible. Incompatible with strong oxidizing agents, strong acids, reducing agents, bases.
InChIKey: SECXISVLQFMRJM-UHFFFAOYSA-N
LogP: -0.46 at 25℃
Surface tension: 41.3mN/m at 293.15K
CAS DataBase Reference: 872-50-4(CAS DataBase Reference)
NIST Chemistry Reference: N-Methyl-2-pyrrolidone(872-50-4)
EPA Substance Registry System: N-Methyl-2-pyrrolidone (872-50-4)
N-Methyl-2-pyrrolidone is a colourless or light yellow liquid with an amine odour.
N-Methyl-2-pyrrolidone can undergo a number of chemical reactions even though it is accepted as a stable solvent.
N-Methyl-2-pyrrolidone is resistant to hydrolysis under neutral conditions, but strong acid or base treatment results in ring opening to 4-methyl aminobutyric acid.
N-Methyl-2-pyrrolidone can be reduced to 1-methyl pyrrolidine with borohydride.
Treatment with chlorinating agents results in amide formation,an intermediate which can undergo further substitution, while treatment with amyl nitrate yields the nitrate.
Olefins can be added to the 3 position by treatment first with oxalic esters, then with appropriate aldehyes (Hort and Anderson 1982).
Uses
N-Methyl-2-pyrrolidone (NMP) is a polar aprotic solvent that has the advantages of low toxicity, high boiling point, outstanding solvency, strong selectivity and good stability.
N-Methyl-2-pyrrolidone is widely used in purification of aromatic hydrocarbon extraction, acetylene, olefins, and diolefins.
N-Methyl-2-pyrrolidone is used in industrial cleaning, and it serves as a solvent for production of pesticides, engineering plastics, coatings, synthetic fibers, and integrated circuits.
N-Methyl-2-pyrrolidone can also be used as an industrial cleanser, dispersant, dye, lubricant and antifreeze.
N-Methyl-2-pyrrolidone is an excellent solvent, widely used in aromatics extraction, lubricating oil refining, acetylene enrichment, butadiene separation and synthesis gas desulfurization.
N-Methyl-2-pyrrolidone is used in gas desulfurization, lubricating oil refining, lubricating oil antifreeze, olefin extraction, and as a solvent for insoluble engineering plastics polymerization.
N-Methyl-2-pyrrolidone can be used in herbicide, to clean insulation materials, semiconductor industry precision instruments and circuit boards, to recycle PVC exhaust, as a detergent, dye supplement and dispersing agent.
N-Methyl-2-pyrrolidone is used in mediums for polymerization reactions such as engineering plastics and aramid fiber.
N-Methyl-2-pyrrolidone is used as a polyvinylidene fluoride solvent and electrode auxiliary material for lithium ion batteries.
high purity grade for ICP-MS detection.
For peptide synthesis.
Solvent for high-temperature resins; petrochemical processing, in the microelectronics fabrication industry, dyes and pigments, industrial and domestic cleaning compounds; agricultural and pharmaceutical formulations
N-Methyl-2-pyrrolidone, is useful for spectrophotometry, chromatography and ICP-MS detection.
N-Methyl-2-pyrrolidone is a polar solvent that is used in organic chemistry and polymer chemistry.
Large scale applications include the recovery and purification of acetylenes, olefins, and diolefins, gas purification, and aromatics extraction from feedstocks.
N-Methyl-2-pyrrolidone is a versatile industrial solvent.
N-Methyl-2-pyrrolidone is currently approved for use only in veterinary pharmaceuticals.
The determination of the disposition and metabolism of N-Methyl-2-pyrrolidone in the rat will contribute toward understanding the toxicology of this exogenous chemical which man may likely be exposed to in increasing amounts.
Industrial uses
1) N-Methyl-2-pyrrolidone is used as a general dipolar aprotic solvent, stable and unreactive;
2) for extraction of aromatic hydrocarbons from lubricating oils;
3) for carbon dioxide removal in ammonia generators;
4) as a solvent for polymerization reactions and polymers;
5) as a paint stripper;
6) for pesticide formulations (USEPA 1985).
Other non-industrial uses of N-Methyl-2-pyrrolidone are based on its properties as a dissociating solvent suitable for electrochemical and physical chemical studies (Langan and Salman 1987).
Pharmaceutical applications make use of the properties of N-Methyl-2-pyrrolidone as a penetration enhancer for a more rapid transfer of substances through the skin.
N-Methyl-2-pyrrolidone has been approved as a solvent for slimicide application to food packaging materials.
Preparation
N-Methyl-2-pyrrolidone is produced industrially by a typical ester-to-amide conversion, by treating gamma-butyrolactone with methylamine.
Alternative routes include the partial hydrogenation of N-methylsuccinimide and the reaction of acrylonitrile with methylamine followed by hydrolysis.
About 200,000 to 250,000 tons are produced annually.
Reactions
N-Methyl-2-pyrrolidone reacts with phosphorus pentasulfide to give its analogous thioamide.
With sodium hydroxide N-Methyl-2-pyrrolidone undergoes reversible ring opening, yielding sodium N-methyl-4-aminobutyrate.
N-Methyl-2-pyrrolidone is used to recover certain hydrocarbons generated in the processing of petrochemicals, such as the recovery of 1,3-butadiene and acetylene.
Its good solvency properties have also led to N-Methyl-2-pyrrolidone's use to dissolve a wide range of polymers.
Specifically, N-Methyl-2-pyrrolidone is used as a solvent for surface treatment of textiles, resins, and metal coated plastics or as a paint stripper.
N-Methyl-2-pyrrolidone is also used as a solvent in the production of polyphenylene sulfide.
N-Methyl-2-pyrrolidone is used in the production of aramid fibers Twaron and Kevlar.
In the pharmaceutical industry, N-methyl-2-pyrrolidone is used in the formulation for drugs by both oral and transdermal delivery routes.
N-Methyl-2-pyrrolidone is also used heavily in lithium ion battery fabrication, as a solvent for electrode preparation, because NMP has a unique ability to dissolve polyvinylidene fluoride binder.
Purisol process
In the Purisol process, developed by Lurgi AG in the 1960s, a cold (ca. −15 °C) aqueous solution of N-Methyl-2-pyrrolidone is used to remove hydrogen sulfide from sour gas and from hydrodesulfurization facilities.
It offers some advantages over the Selexol process in that it is more selective for hydrogen sulfide.
Furthermore, N-Methyl-2-pyrrolidone promotes the hydrolysis of some carbonyl sulfide, a common component of sour gas:
COS + H2O → CO2 + H2S
This hydrolysis step further enriches the hydrogen sulfide content of the off-gas when the NMP is stripped.
The sulfur-rich gas is well suited for a Claus unit, which affords solid elemental sulfur.
