Quick Search
Methylpyrrolidone is a widely used industrial solvent.
Methylpyrrolidone has been used as an excipient in topical pharmaceutical preparations in human medicine and in cosmetics.
Methylpyrrolidone is used as a solubilising agent in veterinary medicines intended for parenteral and topical application.
CAS: 872-50-4
MF: C5H9NO
MW: 99.13
EINECS: 212-828-1
Methylpyrrolidone is an organic compound consisting of a 5-membered lactam.
Methylpyrrolidone is a colorless liquid, although impure samples can appear yellow.
Methylpyrrolidone is miscible with water and with most common organic solvents.
Methylpyrrolidone also belongs to the class of dipolar aprotic solvents such as dimethylformamide and dimethyl sulfoxide.
Methylpyrrolidone 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).
Methylpyrrolidoneis a polar solvent with outstanding characteristics.
Methylpyrrolidone has a wide range of applications because it offers very high solvency, high boiling point, low freezing point, and ease of handling.
Methylpyrrolidone is a versatile industrial solvent.
Methylpyrrolidone is currently approved for use only in veterinary pharmaceuticals.
The determination of the disposition and metabolism of Methylpyrrolidone in the rat will contribute toward understanding the toxicology of this exogenous chemical which man may likely be exposed to in increasing amounts.
Methylpyrrolidone is a high boiling, polar aprotic, low viscosity liquid.
Methylpyrrolidone has a good solvency for a wide range of organic and inorganic compounds and Methylpyrrolidone is miscible with water at all temperatures and has a high chemical and thermal stability.
Methylpyrrolidone is used as a solvent for engineering polymers and coating resins.
Additionally, the polar nature and the low surface tension of Methylpyrrolidone makes it an excellent cleaning medium and paint stripping solvent.
Methylpyrrolidone is a chemical compound.
Methylpyrrolidone can be viewed as a lactam of N-methylaminobutyric acid and is thus a γ-lactam.
Recovery and preparation
Methylpyrrolidone is produced on a large scale by reaction of γ-butyrolactone with methylamine at temperatures of 250-400 °C and pressures of 60-120 bar in adiabatically operated tubular reactors.
The reaction proceeds exothermically.
Methylpyrrolidone mixture is then depressurized and separated by distillation.
The yield of Methylpyrrolidone is usually more than 97%.
The starting material γ-butyrolactone is itself produced practically exclusively from 1,4-butanediol, which in turn can be produced by numerous processes from fossil or renewable raw materials.
Properties - Physical Properties
Methylpyrrolidone is a light-sensitive, hygroscopic, colorless to yellowish liquid with a faint amine-like odor, which is miscible with water.
The viscosity at 25 °C is 1.65 mPa-s, and the surface tension is 40.7 mN/m.
Under normal pressure, the compound boils at 203 °C.
According to Antoine, the vapor pressure function is given by log10(P) = A-(B/(T+C)) (P in kPa, T in K) with A = 7.4, B = 2570 and C = 0 in the temperature range from 361 K to 477 K.
The density of Methylpyrrolidone decreases with increasing temperature.
The temperature dependence function can be described by a quadratic equation according to ρ=α+β-T+γ-T2 with α = 1.26202, β = -7.0026-10-4 , γ = -2.8771-10-7 and T = temperature in Kelvin.
The specific heat capacity increases with temperature.
Compilation of main thermodynamic properties Critical temperature Tc = 721.7 K; Critical pressure pc = 45.2 bar ; Critical density ρc = 3.22 mol-l Melting enthalpy ΔfH = 18.1 kJ-mol-1 at melting point; Vaporization enthalpy ΔVH = 49.5 kJ-mol-1 at normal pressure boiling point.
Methylpyrrolidone has a refractive index very close to that of commercial glass (1.4700).
Consequently, glass rods and glass pipettes virtually disappear optically in this chemical.
Chemical properties
Methylpyrrolidone is a very weak base.
When treated with hydrogen chloride, a solid hydrochloride can be obtained which melts at 86-88 °C.
The aqueous solution reacts alkaline.
A 10% aqueous solution shows a pH of 7.7 to 8.0.
Methylpyrrolidone is chemically very stable.
The lactam ring can be opened only by means of strong acids and bases, resulting in 4-N-methylaminobutyric acid.
Methylpyrrolidone has limited stability to oxygen, with oxidation starting at the 5-position and forming the N-methylsuccinimide via various intermediates.
Methylpyrrolidone can be prepared selectively from NMP using ruthenium tetroxide as oxidant.
With halogenating agents, such as phosgene or phosphorus pentachloride, the compound reacts to give the 2-chloro-1-methylpyrrolidinium chloride, which can be further reacted with various nucleophiles, such as amines or alkoxides.
Methylpyrrolidone acts as a catalyst in the synthesis of carboxylic acid chlorides from the carboxylic acids.
With strong bases such as lithium diisopropylamide, Methylpyrrolidone can be deprotonated in the 3-position, forming an amidenolate structure that can be reacted with alkyl halides or aryl bromides.
Safety Characteristics
Methylpyrrolidone forms flammable vapor-air mixtures above the flash point of 86 °C.
The explosion range is between 1.52 vol% (63 g/m3) as the lower explosion limit (LEL) and 9.5 vol% (392 g/m3) as the upper explosion limit (UEL).
A correlation of the lower explosion limit with the vapor pressure function results in a lower explosion point of 79 °C.
The limiting oxygen concentration is 8.1% by volume at 200 °C.
The limiting gap width was determined to be 0.93 mm.
This results in an assignment to explosion group IIA.
The ignition temperature is 265 °C.
Methylpyrrolidone thus falls into temperature class T3.
Methylpyrrolidone decomposes at a temperature above 300 °C, producing carbon monoxide, carbon dioxide, nitrous gases and hydrogen cyanide.
The conductivity is 2-10-6 S/m at 25 °C.
Methylpyrrolidone is hygroscopic (picks up moisture) but stable under normal conditions.
Methylpyrrolidone will violently react with strong oxidizers such as hydrogen peroxide, nitric acid, sulfuric acid, etc.
The primary decomposition products produce carbon monoxide and nitrogen oxide fumes.
Excessive exposure or spillage should be avoided as a matter of good practice.
Lyondell Chemical Company recommends wearing butyl gloves when using Methylpyrrolidone.
Methylpyrrolidone should be stored in clean, phenolic-lined mild steel or alloy drums.
Methylpyrrolidone 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 - 8.0
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
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℃
CAS DataBase Reference: 872-50-4(CAS DataBase Reference)
NIST Chemistry Reference: 2-Pyrrolidinone, 1-methyl-(872-50-4)
EPA Substance Registry System: N-Methyl-2-pyrrolidone (872-50-4)
Methylpyrrolidone is a 5-member-ring compound containing nitrogen.
Methylpyrrolidone has a wide range of uses due to the following excellent characteristics.
Methylpyrrolidone is highly polar and miscible with most organic solvents (alcohols, ethers, ketones, aromatic hydrocarbons, chlorinated hydrocarbons, etc.). Organic and inorganic substances are highly soluble in it.
Methylpyrrolidone mixes with water in all proportions.
Methylpyrrolidone has a high flash point compared to similar solvents.
The boiling point is high, the freezing point is low, and handling is easy.
Methylpyrrolidone is chemically and thermally stable, and not corrosive.
Uses
Methylpyrrolidone is used to produce fine chemicals from mass-produced chemicals.
Methylpyrrolidone applications in the electronics field have expanded in recent years.
Methylpyrrolidone's high polarity and high solvency power along with our high purity, high-grade production technology enable the high performance needed in this field.
Methylpyrrolidone can dissolve organic and inorganic compounds equally well or better than chlorofluorocarbon solvents.
Therefore Methylpyrrolidone is used in various industrial fields as a cleaning or release agent.
Methylpyrrolidone is replacing 1,1,1-trichloroethane in metal cleaning applications due to the world-wide environmental pollution problems associated with chlorinated solvents.
Methylpyrrolidone is a polar aprotic solvent that has the advantages of low toxicity, high boiling point, outstanding solvency, strong selectivity and good stability.
Methylpyrrolidone is widely used in purification of aromatic hydrocarbon extraction, acetylene, olefins, and diolefins.
Methylpyrrolidone is used in industrial cleaning, and it serves as a solvent for production of pesticides, engineering plastics, coatings, synthetic fibers, and integrated circuits.
Methylpyrrolidone can also be used as an industrial cleanser, dispersant, dye, lubricant and antifreeze.
Methylpyrrolidone is an excellent solvent, widely used in aromatics extraction, lubricating oil refining, acetylene enrichment, butadiene separation and synthesis gas desulfurization.
Methylpyrrolidone is used in gas desulfurization, lubricating oil refining, lubricating oil antifreeze, olefin extraction, and as a solvent for insoluble engineering plastics polymerization.
Methylpyrrolidone 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.
Methylpyrrolidone is used in mediums for polymerization reactions such as engineering plastics and aramid fiber.
Methylpyrrolidone 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.
Industrial uses
1) Methylpyrrolidone 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 Methylpyrrolidone 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 Methylpyrrolidone as a penetration enhancer for a more rapid transfer of substances through the skin (Kydoniieus 1987; Barry and Bennett 1987; Akhter and Barry 1987).
Methylpyrrolidone has been approved as a solvent for slimicide application to food packaging materials (USDA 1986).
Methylpyrrolidone is often used as a solvent because of its thermal stability and high polarity.
Methylpyrrolidone is suitable as a solvent for polymers such as acrylates, epoxies, polyurethanes, polyvinyl chloride, polyimides, polyamideimide and for numerous organic syntheses.
Other important applications include paint removal and the production of polyurethane foam (PU foam).
An important technical application is the extraction of 1,3-butadiene from C4 hydrocarbon streams.
Methylpyrrolidone is also used to absorb acidic components in gas scrubbing.
Metabolic pathway
Rats are administered radio-labeled Methylpyrrolidone, and the major route of excretion by rats is via the urine.
The major metabolite, representing 70-75% of the administered dose, is 4-(methylamino)butenoic acid.
This unsaturated intact product may be formed from the elimination of water, and a hydroxyl group may be present on the metabolite prior to acid hydrolysis.
Carcinogenicity
Rats were exposed to Methylpyrrolidone vapor at 0, 0.04, or 0.4 mg/L for 6 h/day, 5 days/week for 2 years.
Male rats at 0.4 mg/L showed slightly reduced mean body weight.
No life-shortening toxic or carcinogenic effects were observed in rats exposed for 2 years to either 0.04 or 0.4mg/L of N-Methyl-2-pyrrolidone.
By the dermal route, a group of 32 mice received an initiation dose of 25mg of Methylpyrrolidone followed 2 weeks later by applications of the tumor promoter phorbol myristate acetate, three times a week, for more than 25 weeks.
Dimethylcarbamoyl chloride and dimethylbenzanthracene served as positive controls.
Although the Methylpyrrolidone group had three skin tumors, this response was not considered significant when compared with that of the positive controls.
Reactivity Profile
This amine is a very mild chemical base.
Methylpyrrolidone does tend to neutralize acids to form salts plus water.
The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base.
Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides.
Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
Synonyms
1-METHYL-2-PYRROLIDINONE
872-50-4
N-Methylpyrrolidone
N-Methyl-2-pyrrolidone
1-methylpyrrolidin-2-one
1-Methyl-2-pyrrolidone
Methylpyrrolidone
N-Methyl-2-pyrrolidinone
M-Pyrol
N-Methylpyrrolidinone
1-Methylpyrrolidinone
1-Methylpyrrolidone
Methyl pyrrolidone
2-Pyrrolidinone, 1-methyl-
n-methyl-pyrrolidone
1-Methyl-5-pyrrolidinone
1-Methylazacyclopentan-2-one
N-methylpyrrolidin-2-one
NMP
N-Methyl-gamma-butyrolactam
N-methyl pyrrolidone
1-methylpyrrolidine-2-one
N-methyl pyrrolidinone
Methyl-2-pyrrolidinone
1-methyl-2-pyrrolidon
Methylpyrrolidinone
2-Pyrrolidinone, methyl-
Methylpyrrolidone [NF]
N-Methylpyrrolid-2-one
N-Methyl-alpha-pyrrolidone
NSC 4594
Agsolex 1
2687-44-7
N-Methyl-alpha-pyrrolidinone
51013-18-4
NSC-4594
MFCD00003193
JR9CE63FPM
1-methyl-pyrrolidin-2-one
N-Methyl-.alpha.-pyrrolidone
CHEMBL12543
N-Methyl-.gamma.-butyrolactam
CHEBI:7307
N-Methyl-.alpha.-pyrrolidinone
DTXSID6020856
1-Methyl-2-pyrrolidinone, anhydrous
1-Methyl-2-pyrrolidinone, HPLC Grade
N 0131
26876-92-6
N-methyl-pyrrolidinone
pharmasolve
N-Methylpyrrolidon
CAS-872-50-4
CCRIS 1633
Methylpyrrolidone, N-
HSDB 5022
Pyrrolidinone, methyl-
N-Methyl-2-pyrrolidon
1-methyl-2-pyrolidone
EINECS 212-828-1
UNII-JR9CE63FPM
N-methyl-pyrrolidin-2-one
1-Methyl-2-pyrrolidinone, puriss. p.a., >=99.0% (GC)
Micropure ultra
AI3-23116
N-methylpyrolidone
N-methypyrrolidone
Max-1 peptide
Pyrol M
N-methylpirrolidone
1methylpyrrolidinone
n-methyl pyrrolidon
n-methylbutyrolactam
N-methy pyrrolidone
N-methyl-pyrolidone
N-methyl-pyrrolidon
N-methylpyrolidinone
1-methylpyrolidinone
Microposit 2001
n-methylpyrollidinone
N-Methylpyrrolidione
N-methlypyrrolidinone
N-methyl pirrolidone
N-methyl pyrollidone
N-methyl-pyrollidone
N-methylpyrrolidone-
NMP,SP Grade
1-methyl pyrrolidone
1-methyl-pyrrolidone
methyl-2-pyrrolidone
N-methy pyrrolidinone
N-methyl pyrolidinone
N-methyl-pyrolidinone
N-methyl- pyrrolidone
N-methylpyrro-lidinone
N-methylpyrroli-dinone
N-methylpyrrolidin-one
1-methyl-2pyrrolidone
1-methyl2-pyrrolidone
1methyl-2-pyrrolidone
1-methyl pyrrolidinone
1-methyl-pyrrolidinone
methylpyrrolidin-2-one
N-methy-2-pyrrolidone
N-methyl 2-pyrolidone
N-methyl-2-pyrolidone
3p1d
N-methyl 2-pyrrolidone
N-methyl-2-pyrollidone
1-methyl-2-pirrolidone
1-methyl-2-pyroldinone
1-methylpyrrolid-2-one
1methyl-2-pyrrolidinone
n-methylpyrrolidine-2one
N-methyl-2-pyrolidinone
N-methyl-2-pyrrolidinon
N-methylpyrolidin-2-one
1-methy-2-pyrrolidinone
1-methyl-2-pyrolidinone
N-methyl 2-pyrrolidinone
N-methyl-2-pyrollidinone
N-methyl-pyrrolid-2-one
N-methylpyrollidin-2-one
1 -methyl-2-pyrrolidone
1-methyl 2-pyrrolidinone
1-methyl-2-pyrollidinone
1-methyl-pyrrolin-2-one
N-Methylpyrrolidone-(2)
NMP, N-Methylpyrrolidone
1-Methyl-pyrrolidin-2one
N-methylpyrrolidine-2-one
WLN: T5NVTJ A
N-methyl -2-pyrrolidinone
1 -methyl-2-pyrrolidinone
1-methyl -2-pyrrolidinone
1-methyl-2- pyrrolidinone
EC 212-828-1
2-Pyrrolidone, 1-methyl-
1-methyl-pyrrolidine-2-one
1-N-methyl-2-pyrrolidinone
N-methyl-pyrrolidin -2-one
30207-69-3
1-Methylazacyclopentane-2-one
GTPL9520
METHYL PYRROLIDONE [II]
1-Methyl-2- pyrrolidin-2-one
1-METHYLPYRROLIDONE [MI]
METHYL PYRROLIDONE [INCI]
NSC4594
METHYLPYRROLIDONE [USP-RS]
HY-Y1275
N-METHYLPYRROLIDONE [MART.]
ZINC3860621
Tox21_202350
Tox21_300097
1-Methyl-2-pyrrolidinone, 99.5%
BDBM50353587
N-Methyl pyrrolidon (Peptide Grade)
N-METHYLPYRROLIDONE [USP-RS]
s6282
STL183295
N-Methyl-2-pyrrolidinone ACS reagent
AKOS000120930
1-Methyl-2-pyrrolidinone, BioSolv(R)
DB12521
SL 1332
1-Methyl-2-pyrrolidone, Reagent, ACS
1-METHYL-2-PYRROLIDINONE [HSDB]
NCGC00247902-01
NCGC00247902-02
NCGC00253935-01
NCGC00259899-01
BP-31156
N-METHYLPYRROLIDONE [EP MONOGRAPH]
1-Methyl-2-pyrrolidone (Low water content)
AM20110252
CS-0017258
FT-0608052
FT-0672137
FT-0698122
FT-0700571
M0418
M3055
1-Methyl-2-pyrrolidinone, analytical standard
1-Methyl-2-pyrrolidinone, anhydrous, 99.5
1-Methyl-2-pyrrolidinone, for HPLC, >=99%
1-Methyl-2-pyrrolidinone, for synthesis, 99%
D78116
M 0418
Q33103
Residual Solvent Class 2 - N-Methylpyrrolidone
1-Methyl-2-pyrrolidinone, ReagentPlus(R), 99%
1-Methyl-2-pyrrolidinone, Spectrophotometric Grade
2-PYRROLIDONE,1-METHYL MFC5 H9 N1 O1
A842053
1-Methyl-2-pyrrolidinone, ACS reagent, >=99.0%
2,5-Dichloro-4,6-dimethyl pyridine-3-carbonitrile
J-504921
J-803017
1-Methyl-2-pyrrolidinone, biotech. grade, >=99.7%
1-Methyl-2-pyrrolidinone, Electronic/Cleanroom Grade
1-Methyl-2-pyrrolidinone, p.a., ACS reagent, 99%
1-Methyl-2-pyrrolidone, anhydrous, water 40ppm max
1-Methyl-2-pyrrolidinone, SAJ first grade, >=98.0%
Z104478382
1-Methyl-2-pyrrolidinone, spectrophotometric grade, >=99%
1-Methyl-2-pyrrolidinone, Vetec(TM) reagent grade, 98%
1-Methyl-2-pyrrolidinone, for metal speciation analysis, >=99.0% (GC)
Methylpyrrolidone, United States Pharmacopeia (USP) Reference Standard
N-Methylpyrrolidone, Pharmaceutical Secondary Standard; Certified Reference Material
