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1-Methyl-2-pyrrolidinone structure

1-Methyl-2-pyrrolidinone
  • CAS：872-50-4
  • MW:99.13106
  • MF：C5H9NO

1-Methyl-2-pyrrolidinone (C5H9NO, CAS No: 872-50-4, MW: 99.13106 g/mol) is an organic compound. It is a colorless, odorless liquid that is widely used as a solvent in various industrial applications. 1-Methyl-2-pyrrolidinone, commonly known as NMP, is known for its ability to dissolve a wide range of substances, including polymers, resins, and oils. It is commonly used in industries such as electronics, pharmaceuticals, and chemicals.

1-Methyl-2-pyrrolidinone is often employed as a solvent in the production of semiconductors, as well as in paint removers, cleaning products, and coatings. It also plays a role in drug formulation and the extraction of natural products. Due to its high solvency power, it is an effective agent for use in various chemical and industrial processes.

When handling 1-Methyl-2-pyrrolidinone, it should be stored in a cool, dry place and away from direct sunlight. As it can be irritating to the skin and eyes, proper safety precautions, including wearing gloves and eye protection, should be observed. It is also recommended to work in a well-ventilated area to minimize inhalation exposure.

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1. Names and Identifiers
1.1 Name
1-Methyl-2-pyrrolidinone
1.2 Synonyms
1,6-Dihydro-N-methyl-6-oxonicotinamide; 1-methyl-2-oxo-pyrrolidine; 1-Methyl-2-pyrrolidinone 872-50-4 NMP N-Methyl-2-pyrrolidinone; 1-Methyl-2-pyrrolidone; 1-METHYL-2-PYRROLIDONE, REAGENT (ACS)1-METHYL-2-PYRROLIDONE, REAGENT (ACS)1-METHYL-2-PYRROLIDONE, REAGENT (ACS); 1-Methylpyrrolidin-2-on; 1-methylpyrrolidin-2-one; 2-Pyrrolidinone, 1-methyl-; 2-Pyrrolidone, 1-methyl; EINECS 212-828-1; Methyl pyrrolidone; METHYLPYRROLIDINONE; Methylpyrrolidone; Methylpyrrolidone, N-; MFCD00003193; M-PYROL(R); N-methyl pyrrolidinone; N-methyl-2-pyridone-5-carboxamide; N-methyl-2-pyrrolidinone; N-Methyl-2-pyrrolidinone 872-50-4 NMP; N-Methyl-2-pyrrolidone; N-Methyl-2-pyrrolidone Manufacturer; n-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide; N-Methyl-a-pyrrolidinone; N-Methyl-g-butyrolactone; N-methyl-pyrrolidin-2-one; N-methylpyrrolidinone; N-methyl-pyrrolidinone; N-Methyl-Pyrrolidone; N-Methyl-α-pyrrolidinone; N-methyl-α-pyrrolidone; NMP; Pyrrolidinone, methyl-;
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1.3 CAS No.
872-50-4
1.4 CID
13387
1.5 EINECS
212-828-1
1.6 Molecular Formula
C5H9NO
1.7 Inchi
InChI=1S/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3
1.8 InChkey
SECXISVLQFMRJM-UHFFFAOYSA-N
1.9 Canonical Smiles
CN1CCCC1=O
1.10 Isomers Smiles
CN1CCCC1=O
2. Properties
2.1 Vapour pressure
3.4 (vs air)
2.2 Solubility
ethanol: miscible0.1ML/mL, clear, colorless (10%, v/v)
2.3 Λmax
283nm(MeOH)(lit.)
2.4 Viscosity
1.65 cP at 25 deg C
2.5 VaporDensity
3.4 (vs air)
2.6 Appearance
colourless or light yellow liquid with an amine odour
2.7 Storage
NMP is hygroscopic (picks up moisture) but stable under normal conditions. It 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 NMP. NMP should be stored in clean, phenolic-lined mild steel or alloy drums. Teflon®1 and Kalrez®1 have been shown to be suitable gasket materials. Please review MSDS prior to handling.
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2.8 Autoignition Temperature
655 Deg F (346 DEG C)
2.9 Carcinogenicity
Rats were exposed to NMPvapor at 0, 0.04, or 0.4 mg/L for 6 h/day, 5 days/week for2 years.Male rats at 0.4 mg/L showed slightly reduced meanbody weight. No life-shortening toxic or carcinogeniceffects were observed in rats exposed for 2 years to either0.04 or 0.4mg/L of NMP. By the dermal route, a group of 32mice received an initiation dose of 25mg of NMP followed2 weeks later by applications of the tumor promoter phorbolmyristate acetate, three times a week, for more than25 weeks. Dimethylcarbamoyl chloride and dimethylbenzanthraceneserved as positive controls. Although the NMPgroup had three skin tumors, this response was not consideredsignificant when compared with that of the positivecontrols.
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2.10 Chemical Properties
1-Methyl-2-pyrrolidinone is also known as NMP, 1-methyl-2-pyrrolidone, N-methylpyrrolidone, and N-Methyl-2-pyrrolidone. NMP is a colorless to light yellow transparent liquid with a slight ammonia odor. NMP is completely miscible with water. It is highly soluble in lower alcohols, lower ketones, ether, ethyl acetate, chloroform, and benzene and moderately soluble in aliphatic hydrocarbons. NMP is strongly hygroscopic, chemically stable, not corrosive towards carbon steel and aluminum, and slightly corrosive to copper. It has low adhesiveness, strong chemical and thermal stability, high polarity, and low volatility. This product is slightly toxic, and its permitted concentration limit in air is 100ppm.
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2.11 Color/Form
≤20(APHA)
2.12 Contact Allergens
1-Methylpyrrolidone 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. It is mainly an irritant, but it can cause severe contact dermatitis due to prolonged contact.
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2.13 Decomposition
Decomposes on heating and on burning. This produces toxic fumes including nitrogen oxides and carbon monoxide.
2.14 Heat of Combustion
719 kcal/mol
2.15 Heat of Vaporization
127.3 kcal/Kg
2.16 HenrysLawConstant
3.20e-09 atm-m3/mole
2.17 Odor
Mild amine odor
2.18 PH
pH = 7.7-8
2.19 pKa
-0.41±0.20(Predicted)
2.20 Water Solubility
>=10 g/100 mL at 20 oC
2.21 Spectral Properties
MAX ABSORPTION (METHANOL): 205 NM (LOG E= 3.46); INDEX OF REFRACTION: 1.4684 AT 20 DEG C/D; SADTLER REFERENCE NUMBER: 6528 (IR, PRISM); 116 (VARIAN, NMR)
IR 6528 (Sadtler Research Laboratories Prism Collection)
UV 4-43 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York
NMR 116 (Varian Associates NMR Spectra Catalogue)
MASS 4006 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63
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2.22 Stability
Stable, but decomposes upon exposure to light. Combustible. Incompatible with strong oxidizingagents, strong acids, reducing agents, bases.
2.23 StorageTemp
Store at +5°C to +30°C.
2.24 Surface Tension
40.7 dynes/cm
3. Use and Manufacturing
3.1 Definition
ChEBI: 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.
3.2 Description
1-Methyl-2-pyrrolidinone (NMP) has a molecular formula of C5H9NO, and it is a colorless to light yellow transparent liquid with a slight ammonia odor. Its boiling point is 204℃, flash point is 91℃, chroma HaZen≤25, refractive index N20D 1.468-1.471, density is 1.032-1.035. It is miscible in water at any ratio, it is soluble in ethanol, acetone, esters, halogenated hydrocarbons, aromatic hydrocarbons and other organic solvents, and it can completely mix with practically all solvents. It is stron
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3.3 General Description
N-Methyl-2-Pyrrolidone (NMP) is a powerful, aprotic solvent with high solvency, and low volatility. This colorless, high boiling, high flash point and low vapor pressure liquid carries a mild amine-like odor. NMP has high chemical and thermal stability and is completely miscible with water at all temperatures. NMP can serve as a co-solvent with water, alcohols, glycol ethers, ketones, and aromatic/chlorinated hydrocarbons. NMP is both recyclable by distillation and readily biodegradable. NMP is not found on the Hazardous Air Pollutants (HAPs) list of the 1990 Clean Air Act Amendments.
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3.4 Produe Method
1-Methyl-2-pyrrolidinone is manufactured by the reaction of buytrolactone with methylamine (Hawley 1977). Other processes include preparation by hydrogenation of solutions of maleic or succinic acids with methylamine (Hort and Anderson 1982). Manufacturers of this chemical include Lachat Chemical, Inc, Mequon, Wisconsin and GAF Corporation, Covert City, California.
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3.5 Purification Methods
Dry the pyrrolidone by removing water as the *benzene azeotrope. Fractionally distil at 10 torr through a 100-cm column packed with glass helices. [Adelman J Org Chem 29 1837 1964, McElvain & Vozza J Am Chem Soc 71 896 1949.] The hydrochloride has m 86-88o (from EtOH or Me2CO/EtOH) [Reppe et al. Justus Liebigs Ann Chem 596 1 1955]. [Beilstein 21 II 213, 21 III/IV 3145, 21/6 V 321.] 1-Methyl-2-pyrrolidinone Preparation Products And Raw materials Raw materials
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3.6 Usage
1-Methyl-2-pyrrolidinone (NMP) is a polar aprotic solvent that has the advantages of low toxicity, high boiling point, outstanding solvency, strong selectivity and good stability. It is widely used in purification of aromatic hydrocarbon extraction, acetylene, olefins, and diolefins.It is used in industrial cleaning, and it serves as a solvent for production of pesticides, engineering plastics, coatings, synthetic fibers, and integrated circuits.It can also be used as an industrial cleanser, dispersant, dye, lubricant and antifreeze.1-Methyl-2-pyrrolidinone is an excellent solvent, widely used in aromatics extraction, lubricating oil refining, acetylene enrichment, butadiene separation and synthesis gas desulfurization.It is used in gas desulfurization, lubricating oil refining, lubricating oil antifreeze, olefin extraction, and as a solvent for insoluble engineering plastics polymerization.It 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.It is used in mediums for polymerization reactions such as engineering plastics and aramid fiber.1-Methyl-2-pyrrolidinone 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.
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3.7 Waste Disposal
Consult state, local or national regulations for proper disposal. Disposal must be made according to official regulations. Water, if necessary with cleansing agents.
4. Safety and Handling
4.1 Octanol/Water Partition Coefficient
log Kow= -0.54
4.2 Fire Hazard
Special Hazards of Combustion Products: Toxic oxides of nitrogen may be formed in fire.
4.3 Other Preventative Measures
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
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4.4 Cleanup Methods
REMOVAL OF N-METHYLPYRROLIDONE FROM WASTEWATER BY PHYSICOCHEMICAL TREATMENT, USING POWDERED ACTIVATED CARBON AS ADSORBENT.
4.5 DisposalMethods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
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4.6 Fire Fighting Procedures
Dry chemical, "alcohol" foam, and carbon dioxide.
4.7 FirePotential
Combustible when exposed to heat, open flame, or powerful oxidizers.
4.8 Safety Profile
Poison by intravenousroute. Moderately toxic by ingestion andintraperitoneal routes. Mildly toxic by skincontact. An experimental teratogen.Experimental reproductive effects. Mutationdata reported. Combustible when exposedto heat, open flame, or powerful oxidizers.To fight fire, use foam, CO2, dry chemical.When heated to decomposition it emitstoxic fumes of NOx.
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4.9 Protective Equipment and Clothing
... Is a severe eye irritant.
4.10 Reactivities and Incompatibilities
Reacts with chlorinating agents, eg, cobalt chloride, thionyl chloride, phosphorus oxychloride, & pentachlorophosphorus to form the amide.
Reacts with sulfur or carbon disulfide at high temperatures and pressures.
Combustible when exposed to ... powerful oxidizers.
4.11 Report

Reported in EPA TSCA Inventory.

4.12 Skin, Eye, and Respiratory Irritations
... Is a severe eye irritant.
4.13 Safety

Poison by intravenous route. Moderately toxic by ingestion and intraperitoneal routes. Mildly toxic by skin contact. An experimental teratogen. Experimental reproductive effects. Mutation data reported. Combustible when exposed to heat, open flame, or powerful oxidizers. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: ToxicT,IrritantXi
Safety Statements: 41
S41: In case of fire and / or explosion do not breathe fumes.
Risk Statements: 45-65-36/38?
R36/38: Irritating to eyes and skin.?
R45: May cause cancer.?
R65: Harmful: may cause lung damage if swallowed.

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4.14 Sensitive
Hygroscopic
4.15 Specification

?N-methyl-pyrrolidone , its cas register number is 872-50-4. It also can be called N-Methyl-2-pyrrolidinone ; N-Methyl-2-Pyrrolidone ; NMP ; and N-Methylpyrrolidone . It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Then you have the ingesting of the product: Wash mouth out with water, and get medical aid immediately.
In addition, N-methyl-pyrrolidone (CAS NO.872-50-4) could be stable?at room temperature in closed containers under normal storage and handling conditions. It is not compatible with strong oxidizing agents, strong acids, strong bases, and you must not take it with incompatible materials, light, temperatures above 100 °C, exposure to moist air or water. And also prevent it to broken down into hazardous decomposition products:?nitrogen oxides, carbon monoxide, carbon dioxide.

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4.16 Toxicity
Organic Compound; Solvent; Amine; Amide; Household Toxin; Industrial/Workplace Toxin; Synthetic Compound
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

Reproductive toxicity, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H315 Causes skin irritation

H319 Causes serious eye irritation

H335 May cause respiratory irritation
Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P271 Use only outdoors or in a well-ventilated area.

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

Response

P302+P352 IF ON SKIN: Wash with plenty of water/...

P321 Specific treatment (see ... on this label).

P332+P313 If skin irritation occurs: Get medical advice/attention.

P362+P364 Take off contaminated clothing and wash it before reuse.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313 If eye irritation persists: Get medical advice/attention.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.

P308+P313 IF exposed or concerned: Get medical advice/ attention.

Storage

P403+P233 Store in a well-ventilated place. Keep container tightly closed.

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum
Mass spectrum (electron ionization)  
UV/Visible spectrum  
7. Synthesis Route
872-50-4Total: 85 Synthesis Route
 
77-78-1
77-78-1 91 Suppliers
 
872-50-4
872-50-4 616 Suppliers
 
74-89-5
74-89-5
 
872-50-4
872-50-4 616 Suppliers
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8. Precursor and Product
precursor:
616-45-5
616-45-5
77-78-1
77-78-1
620-08-6
620-08-6
120-94-5
120-94-5
product:
693-11-8
693-11-8
4266-03-9
4266-03-9
106-52-5
106-52-5
6602-17-1
6602-17-1
1121-07-9
1121-07-9
76-05-1
76-05-1
765-48-0
765-48-0
496-49-1
496-49-1
1119-48-8
1119-48-8
120-94-5
120-94-5
9. Computed Properties
10.Other Information
Usage
1-methyl-2-pyrrolidinone is useful for the chemical functionalization of graphene sheets by solvothermal reduction of graphene oxide. It is also useful for pharmaceutical and different industrial applications due to its broad solvency and low volatility. It is used as stripping agent, oven cleaners and paint strippers. It is involved in the extraction of lube oil process and in the purification of synthetic gas.
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Usage
1-methyl-2-pyrrolidinone, is useful for spectrophotometry, chromatography and ICP-MS detection. It is useful for the chemical functionalization of graphene sheets by solvothermal reduction of graphene oxide. It is also useful for pharmaceutical and different industrial applications due to its broad solvency and low volatility.
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Usage
Suitable for Biotech applications.1-methyl-2-pyrrolidinone, is useful for spectrophotometry, chromatography and ICP-MS detection. It is useful for the chemical functionalization of graphene sheets by solvothermal reduction of graphene oxide. It is also useful for pharmaceutical and different industrial applications due to its broad solvency and low volatility.
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Usage
1-methyl-2-pyrrolidinone, is useful for spectrophotometry, chromatography and ICP-MS detection.
Merck
14,6117
BRN
106420
Chemical Properties
1-Methyl-2-pyrrolidinone is also known as NMP, 1-methyl-2-pyrrolidone, N-methylpyrrolidone, and N-Methyl-2-pyrrolidone. NMP is a colorless to light yellow transparent liquid with a slight ammonia odor. NMP is completely miscible with water. It is highly soluble in lower alcohols, lower ketones, ether, ethyl acetate, chloroform, and benzene and moderately soluble in aliphatic hydrocarbons. NMP is strongly hygroscopic, chemically stable, not corrosive towards carbon steel and aluminum, and slightly corrosive to copper. It has low adhesiveness, strong chemical and thermal stability, high polarity, and low volatility. This product is slightly toxic, and its permitted concentration limit in air is 100ppm.
1-Methyl-2-pyrrolidinone
N-Methylpyrrolidone (NMP) is a solvent used in a variety of industries and applications, such as paint and coating removal, petrochemical processing, engineering plastics coatings, agricultural chemicals, electronic cleaning and industrial/domestic cleaning.
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Uses
  1. 1-Methyl-2-pyrrolidinone (NMP) is a polar aprotic solvent that has the advantages of low toxicity, high boiling point, outstanding solvency, strong selectivity and good stability. It is widely used in purification of aromatic hydrocarbon extraction, acetylene, olefins, and diolefins.
  2. It is used in industrial cleaning, and it serves as a solvent for production of pesticides, engineering plastics, coatings, synthetic fibers, and integrated circuits.
  3. It can also be used as an industrial cleanser, dispersant, dye, lubricant and antifreeze.
  4. 1-Methyl-2-pyrrolidinone is an excellent solvent, widely used in aromatics extraction, lubricating oil refining, acetylene enrichment, butadiene separation and synthesis gas desulfurization.
  5. It is used in gas desulfurization, lubricating oil refining, lubricating oil antifreeze, olefin extraction, and as a solvent for insoluble engineering plastics polymerization.
  6. It 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.
  7. It is used in mediums for polymerization reactions such as engineering plastics and aramid fiber.
  8. 1-Methyl-2-pyrrolidinone is used as a polyvinylidene fluoride solvent and electrode auxiliary material for lithium ion batteries.
  9. high purity grade for ICP-MS detection.
  10. For peptide synthesis.
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toxicity

Oral (mus)LD50:5130 mg/kg;Oral (rat)LD50:3914 mg/kg;Dermal (rbt)LD50:8000 mg/kg.

Waste Disposal
Consult state, local or national regulations for proper disposal. Disposal must be made according to official regulations. Water, if necessary with cleansing agents.
storage
NMP is hygroscopic (picks up moisture) but stable under normal conditions. It 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 NMP. NMP should be stored in clean, phenolic-lined mild steel or alloy drums. Teflon?1 and Kalrez?1 have been shown to be suitable gasket materials. Please review MSDS prior to handling.
View all
Description
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. It is mainly an irritant, but has also caused several cases of contact dermatitis in a small electrotechnical company.
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Chemical Properties
1-Methyl-2-pyrrolidinone is a colourless or light yellow liquid with an amine odour. It can undergo a number of chemical reactions even though it is accepted as a stable solvent. It is resistant to hydrolysis under neutral conditions, but strong acid or base treatment results in ring opening to 4-methyl aminobutyric acid. 1-Methyl-2-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).
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Uses
1-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.
1-Methyl-2-pyrrolidinone is a versatile industrial solvent. NMP is currently approved for use only in veterinary pharmaceuticals. The determination of the disposition and metabolism of NMP in the rat will contribute toward understanding the toxicology of this exogenous chemical which man may likely be exposed to in increasing amounts.
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Uses
Solvent for high-temperature resins; petrochemical processing, in the microelectronics fabrication industry, dyes and pigments, industrial and domestic cleaning compounds; agricultural and pharmaceutical formulations
Definition
ChEBI: 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.
Production Methods
1-Methyl-2-pyrrolidinone is manufactured by the reaction of buytrolactone with methylamine (Hawley 1977). Other processes include preparation by hydrogenation of solutions of maleic or succinic acids with methylamine (Hort and Anderson 1982). Manufacturers of this chemical include Lachat Chemical, Inc, Mequon, Wisconsin and GAF Corporation, Covert City, California.
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Synthesis Reference(s)
Tetrahedron Letters, 24, p. 1323, 1983 DOI: 10.1016/S0040-4039(00)81646-9
General Description
N-Methyl-2-Pyrrolidone (NMP) is a powerful, aprotic solvent with high solvency, and low volatility. This colorless, high boiling, high flash point and low vapor pressure liquid carries a mild amine-like odor. NMP has high chemical and thermal stability and is completely miscible with water at all temperatures. NMP can serve as a co-solvent with water, alcohols, glycol ethers, ketones, and aromatic/chlorinated hydrocarbons. NMP is both recyclable by distillation and readily biodegradable. NMP is not found on the Hazardous Air Pollutants (HAPs) list of the 1990 Clean Air Act Amendments.
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Air & Water Reactions
Soluble in water.
Reactivity Profile
This amine is a very mild chemical base. 1-Methyl-2-pyrrolidinone 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.
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Hazard
Severe skin and eye irritant. Explosive lim-its 2.2–12.2%.
Health Hazard
Inhalation of hot vapors can irritate nose and throat. Ingestion causes irritation of mouth and stomach. Contact with eyes causes irritation. Repeated and prolonged skin contact produces a mild, transient irritation.
Fire Hazard
Special Hazards of Combustion Products: Toxic oxides of nitrogen may be formed in fire.
Industrial uses
1) 1-Methyl-2-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-2-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-2-pyrrolidinone as a penetration enhancer for a more rapid transfer of substances through the skin (Kydoniieus 1987; Barry and Bennett 1987; Akhter and Barry 1987). 1-Methyl-2-pyrrolidinone has been approved as a solvent for slimicide application to food packaging materials (USDA 1986).
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Contact allergens
1-Methylpyrrolidone 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. It is mainly an irritant, but it can cause severe contact dermatitis due to prolonged contact.
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Safety Profile
Poison by intravenous route. Moderately toxic by ingestion and intraperitoneal routes. Mildly toxic by skin contact. An experimental teratogen. Experimental reproductive effects. Mutation data reported. Combustible when exposed to heat, open flame, or powerful oxidizers. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of NOx.
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Carcinogenicity
Rats were exposed to NMP 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 NMP. By the dermal route, a group of 32 mice received an initiation dose of 25mg of NMP 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 NMP group had three skin tumors, this response was not considered significant when compared with that of the positive controls.
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Metabolic pathway
Rats are administered radio-labeled N-methyl-2- pyrrolidinone (NMP), 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.
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Metabolism
Male Sprague-Dawley rats were given a single intraperitoneal injection (45 mg/kg) of radiolabeled 1 -methyl-2-pyrrolidone. 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 l-methyl-2-pyrrolidone. 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).
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Purification Methods
Dry the pyrrolidone by removing water as the *benzene azeotrope. Fractionally distil at 10 torr through a 100-cm column packed with glass helices. [Adelman J Org Chem 29 1837 1964, McElvain & Vozza J Am Chem Soc 71 896 1949.] The hydrochloride has m 86-88o (from EtOH or Me2CO/EtOH) [Reppe et al. Justus Liebigs Ann Chem 596 1 1955]. [Beilstein 21 II 213, 21 III/IV 3145, 21/6 V 321.]
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12. Related Questions
What is N-Methyl-2-pyrrolidone and how is it synthesized? Description NMP, also known as N-methyl-α-pyrrolidinone, is a derivative of γ-butyrolactone. It is a colorless and transparent liquid with a slight ammonia smell. NMP is a high-polarity, chemically..
What are the Uses and Toxicity of N-methyl-2-pyrrolidone?Uses of N-methyl-2-pyrrolidone N-methyl-2-pyrrolidone(NMP) serves as both a solvent and an accelerator in various industrial processes. It is utilized for extractions in cracking oils and petrochemica..
What is NMP 1-Methyl-2-pyrrolidinone and how is it used?NMP 1-Methyl-2-pyrrolidinone (N-Methyl-2-Pyrrolidone) is a colorless and transparent organic solvent with the chemical formula C5H9NO, commonly abbreviated as NMP. It is widely used in industrial prod..
What is NMP 1-Methyl-2-pyrrolidinone and its Applications?NMP 1-Methyl-2-pyrrolidinone, also known as N-Methyl-2-pyrrolidone, is a commonly used organic solvent with a wide range of applications in the chemical industry. It is a highly polar solvent and can ..
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