1-Methyl-5-pyrrolidinone, Reagent, ACS is a laboratory analytical reagent that is miscible with water and several other solvents, including ethyl acetate, chloroform, benzene and alcohols and ketones.
1-Methyl-5-pyrrolidinone is colorless to slightly yellow, and is used in the processing of petrochemicals to recover pure hydrocarbons.
1-Methyl-5-pyrrolidinone is also commonly used to dissolve a broad range of chemicals, in particular polymers.
There are several industrial uses, including treating surfaces of textiles, resins and plastics, as well as for stripping paint.
As an ACS grade Reagent, Spectrum Chemical manufactured 1-Methyl-5-pyrrolidinone is used as the quality standard against which other substances are graded and has met the toughest regulatory standards for quality and pureness.
1-Methyl-5-pyrrolidinone is an organic compound consisting of a 5-membered lactam.
1-Methyl-5-pyrrolidinone is a colorless liquid, although impure samples can appear yellow.
1-Methyl-5-pyrrolidinone is miscible with water and with most common organic solvents.
1-Methyl-5-pyrrolidinone also belongs to the class of dipolar aprotic solvents such as dimethylformamide and dimethyl sulfoxide.
1-Methyl-5-pyrrolidinone 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).
1-Methyl-5-pyrrolidinone appears as a clear colorless liquid with a "fishlike" odor.
Denser than water. Flash point 199 °F.
Contact may irritate skin, eyes and mucous membranes.
May be toxic by ingestion.
1-Methyl-5-pyrrolidinone 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.
1-Methyl-5-pyrrolidinone has a role as a polar aprotic solvent.
1-Methyl-5-pyrrolidinone is a N-alkylpyrrolidine, a lactam and a member of pyrrolidin-2-ones.
1-Methyl-5-pyrrolidinone is useful for the chemical functionalization of graphene sheets by solvothermal reduction of graphene oxide.
1-Methyl-5-pyrrolidinone is also useful for pharmaceutical and different industrial applications due to its broad solvency and low volatility.
1-Methyl-5-pyrrolidinone is used as stripping agent, oven cleaners and paint strippers.
1-Methyl-5-pyrrolidinone is involved in the extraction of lube oil process and in the purification of synthetic gas.
1-Methyl-5-pyrrolidinone 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.
1-Methyl-5-pyrrolidinone is mainly an irritant, but has also caused several cases of contact dermatitis in a small electrotechnical company.
1-Methyl-5-pyrrolidinone 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)
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
Stability: Stable, but decomposes upon exposure to light. Combustible. Incompatible with strong oxidizing agents, strong acids, reducing agents, bases.
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)
1-Methyl-5-pyrrolidinone is a colourless or light yellow liquid with an amine odour.
1-Methyl-5-pyrrolidinone can undergo a number of chemical reactions even though it is accepted as a stable solvent.
1-Methyl-5-pyrrolidinone is resistant to hydrolysis under neutral conditions, but strong acid or base treatment results in ring opening to 4-methyl aminobutyric acid.
1-Methyl-5-pyrrolidinone 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).
1-Methyl-5-pyrrolidinone is used to recover certain hydrocarbons generated in the processing of petrochemicals, such as the recovery of 1,3-butadiene and acetylene.
1-Methyl-5-pyrrolidinone is used to absorb hydrogen sulfide from sour gas and hydrodesulfurization facilities.
1-Methyl-5-pyrrolidinone's good solvency properties have led to 1-Methyl-5-pyrrolidinone's use to dissolve a wide range of polymers.
Specifically, 1-Methyl-5-pyrrolidinone is used as a solvent for surface treatment of textiles, resins, and metal coated plastics or as a paint stripper.
1-Methyl-5-pyrrolidinone is also used as a solvent in the commercial preparation of polyphenylene sulfide.
In the pharmaceutical industry, 1-Methyl-5-pyrrolidinone is used in the formulation for drugs by both oral and transdermal delivery routes.
1-Methyl-5-pyrrolidinone is also used heavily in lithium ion battery fabrication, as a solvent for electrode preparation, because 1-Methyl-5-pyrrolidinone has a unique ability to dissolve polyvinylidene fluoride binder.
Due to 1-Methyl-5-pyrrolidinone's toxicity and high boiling point, there is much effort to replace it in battery manufacturing with other solvent(s), like water.
1) 1-Methyl-5-pyrrolidinone 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 1-Methyl-5-pyrrolidinone 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 1-Methyl-5-pyrrolidinone as a penetration enhancer for a more rapid transfer of substances through the skin.
1-Methyl-5-pyrrolidinone has been approved as a solvent for slimicide application to food packaging materials.
1-Methyl-5-pyrrolidinone 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.
1-Methyl-5-pyrrolidinone is a versatile industrial solvent.
1-Methyl-5-pyrrolidinone is currently approved for use only in veterinary pharmaceuticals.
The determination of the disposition and metabolism of 1-Methyl-5-pyrrolidinone in the rat will contribute toward understanding the toxicology of this exogenous chemical which man may likely be exposed to in increasing amounts.
1-Methyl-5-pyrrolidinone is an agent that causes the production of physical defects in the developing embryo.
1-Methyl-5-pyrrolidinone also is a reproductive toxin, a chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function.
Reproductive toxicity includes developmental effects.
1-Methyl-5-pyrrolidinone can be absorbed into the body by inhalation, through the skin and by ingestion.
When people are exposed to 1-Methyl-5-pyrrolidinone, rapid, irregular respiration, shortness of breath, decreased pain reflex, and slight bloody nasal secretion are possible.
Inhalation can result in headaches and exposure on skin can result in redness and pain.
When ingested 1-Methyl-5-pyrrolidinone will cause a burning sensation in the throat and chest.
1-Methyl-5-pyrrolidinone also can cause an acute solvent syndrome.
In rats, 1-Methyl-5-pyrrolidinone is absorbed rapidly after inhalation, oral, and dermal administration, distributed throughout the organism, and eliminated mainly by hydroxylation to polar compounds, which are excreted via urine.
About 80% of the administered dose is excreted as 1-Methyl-5-pyrrolidinone and 1-Methyl-5-pyrrolidinone metabolites within 24 hours.
A probably dose dependent yellow coloration of the urine in rodents is observed.
The major metabolite is 5-hydroxy-N-methyl-2-pyrrolidone.
Studies in humans show comparable results.
Dermal penetration through human skin has been shown to be very rapid.
1-Methyl-5-pyrrolidinone is rapidly biotransformed by hydroxylation to 5-hydroxy-N-methyl-2-pyrrolidone, which is further oxidized to N-methylsuccinimide; this intermediate is further hydroxylated to 2-hydroxy-N-methylsuccinimide.
These metabolites are all colourless.
The excreted amounts of 1-Methyl-5-pyrrolidinone metabolites in the urine after inhalation or oral intake represented about 100% and 65% of the administered doses, respectively.
1-Methyl-5-pyrrolidinone has a low potential for skin irritation and a moderate potential for eye irritation in rabbits.
Repeated daily doses of 450 mg/kg body weight administered to the skin caused painful and severe haemorrhage and eschar formation in rabbits.
These adverse effects have not been seen in workers occupationally exposed to pure 1-Methyl-5-pyrrolidinone, but they have been observed after dermal exposure to NMP used in cleaning processes.
No sensitization potential has been observed.
Male Sprague-Dawley rats were given a single intraperitoneal injection (45 mg/kg) of radiolabeled 1-Methyl-5-pyrrolidinone.
Plasma levels of radioactivity and compound were monitored for six hours and the results suggested a rapid distribution phase which was followed by a slow elimination phase.
The major amount of label was excreted in the urine within 12 hours and accounted for approximately 75% of the labelled dose.
Twenty-four hours after dosage, cumulative excretion (urine) was approximately 80% of the dose.
Both ring- and methyl-labeled species were used, as well as both [14C]- and [3H]-labeled 1-Methyl-5-pyrrolidinone.
The initial labeled ratios were maintained during the first 6 hours after dosage.
After 6 hours, the liver and intestines were found to contain the highest accumulations of radioactivity, approximately 2-4% of the dose.
Little radioactivity was noted in the bile or respired air.
High performance liquid chromatography of urine showed the presence of one major and two minor metabolites.
The major metabolite (70-75% of the administered radioactive dose) was analyzed by liquid chromatography-mass spectrometry and gas chromatography-mass spectrometry and was proposed to be a 3- or 5-hydroxy-l-methyl-2-pyrrolidone (Wells 1987).
1-Methyl-5-pyrrolidinone is produced industrially by a typical ester-to-amide conversion, by treating 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.
1-Methyl-2-pyrrolidinone, HPLC Grade
1-Methyl-2-pyrrolidinone, puriss. p.a., >=99.0% (GC)
WLN: T5NVTJ A
METHYL PYRROLIDONE [II]
METHYL PYRROLIDONE [INCI]
N-Methyl pyrrolidon (Peptide Grade)
N-Methyl-2-pyrrolidinone ACS reagent
1-Methyl-2-pyrrolidone, Reagent, ACS
N-METHYLPYRROLIDONE [EP MONOGRAPH]
1-Methyl-2-pyrrolidone (Low water content)
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%
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
1-Methyl-2-pyrrolidinone, ACS reagent, >=99.0%
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%
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