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N-METHYL 2-PYROLIDONE (NMP)

 


N-Methyl-2-pyrrolidone is an organic compound consisting of a 5-membered lactam.
N -Methyl-2-pyrrolidone is a colorless liquid.
N -Methyl-2-pyrrolidone is used as a solvent in the petrochemical, polymer and battery industries.
N -Methyl-2-pyrrolidone is exploited for its non-volatility and ability to dissolve a variety of materials.

 


CAS number:872-50-4
molecular weight:99.13
molecular formula:C5H9NO
EC number:212-828-1


N-Methyl-2-Pyrrolidone (NMP) is a high boiling point, polar aprotic, low viscosity liquid.
N-Methyl-2-Pyrrolidone has good solubility for a wide range of organic and inorganic compounds.
N-Methyl-2-Pyrrolidone is miscible with water at all temperatures.
N-Methyl-2-Pyrrolidone has high chemical and thermal stability.

It is used as a solvent for engineering polymers and coating resins.
Additionally, N-Methyl-2-Pyrrolidone's polar structure and low surface tension make it an excellent cleaning medium and paint removal solvent.
N-Methyl-2-Pyrrolidone is a powerful solvent with low volatility used for a wide variety of chemicals.
N -Methyl-2-pyrrolidone is miscible with water and most common organic solvents.
It also belongs to the class of dipolar aprotic solvents such as dimethylformamide and dimethyl sulfoxide.
N -Methyl-2-pyrrolidone is miscible with water and most common organic solvents.
N-Methyl-2-pyrrolidone is produced industrially via conversion to a typical ester-amide by treatment of butyrolactone with methylamine.
Alternative pathways include partial hydrogenation of N-methylsuccinimide and reaction of acrylonitrile with methylamine followed by hydrolysis.
Approximately 200,000 to 250,000 tonnes of N-Methyl-2-pyrrolidone are produced annually.

N -Methyl-2-pyrrolidone production is produced by the reaction of buttrolactone with methylamine.
It is prepared by the preparation of maleic and succinic acid solutions, among other processes.
N -Methyl-2-pyrrolidone is used as a drug solubilizer and penetration enhancer in human and animal dosage forms.
In transdermal drug formulations, N-Methyl-2-pyrrolidone increases the short-term permeability of the skin so that the drug is absorbed in a shorter time.
In such applications, Propylene Glycol, Ethyl Alcohol, N-Dimethylformamide and N-Methyl-2-Pyrrolidone are used as penetration enhancing agents.
N -Methyl-2-pyrrolidone is a versatile industrial solvent.
N -Methyl-2-pyrrolidone is used to extract aromatic hydrocarbons from lubricating oils.
N -Methyl-2-pyrrolidone is a common auxiliary solvent used in the creation of water-based polyurethane dispersions.
It helps in the processing of PUDs and the formation of the applied polyurethane film coating.

In addition, N -Methyl-2-pyrrolidone has the property of substrate wetting, freeze/thaw stability and adhesion to some substrates.
N -Methyl-2-pyrrolidone helps to act as a microbicide in wet phases.
N -Methyl-2-pyrrolidone is used to remove carbon dioxide in ammonia generators.
N -Methyl-2-pyrrolidone is used as a good solvent in polymerization reactions and polymers.
N -Methyl-2-pyrrolidone is used as a good paint stripper.
N -Methyl-2-pyrrolidone is used in the production of pesticides.
N -Methyl-2-pyrrolidone is used in pharmaceutical applications as a penetration enhancer for faster substance transfer through the skin.
N -Methyl-2-pyrrolidone is used in the production of weak amine gas washing solutions.
N -Methyl-2-pyrrolidone is absorbed with amine solutions coming from the opposite direction to prevent acidic impurities.

 

Appearance: Colorless transparent liquid
Purity: 99.90%
Melting point: -24 degrees
Boiling point: 202 degrees
Density: 1.028 g/ml
Refractive index: 1.465-1.470
Flash point: 95 degrees
PH: 7.5-10
Solubility: Soluble in water, alcohol, ether, ester, ketone,
aromatic hydrocarbons, halogenated hydrocarbons.

 


N -Methyl-2-pyrrolidone is used to recover certain hydrocarbons produced in the processing of petrochemicals, such as the recovery of 1,3-butadiene and acetylene.
N-Methyl-2-pyrrolidone is used to absorb hydrogen sulfide from sour gas and hydrodesulfurization plants.
Good solubility properties have led to N-Methyl-2-pyrrolidone being used to dissolve a wide variety of polymers.
It is especially used as a solvent or paint remover in the surface treatment of textiles, resins and metal-coated plastics.
It is also used as a solvent in the commercial preparation of polyphenylene sulfide.
In the pharmaceutical industry, N-methyl-2-pyrrolidone is used in drug formulation through both oral and transdermal administration routes.
It is also used extensively as a solvent in electrode preparation in lithium-ion battery production.
N -Methyl-2-pyrrolidone has the unique ability to dissolve the polyvinylidene fluoride binder.
Due to the toxicity of N-Methyl-2-pyrrolidone, much effort is being made to replace it with other solvents such as water in battery production

N-Methyl-2-pyrrolidone is a substance that causes physical defects in the developing embryo.
Also N -Methyl-2-pyrrolidone is a reproductive toxin.
N-Methyl-2-pyrrolidone is a toxic chemical that may cause defects in offspring, including damage to male or female reproductive functions.
Reproductive toxicity also includes developmental effects.
N-Methyl-2-pyrrolidone can be absorbed into the body by inhalation, through the skin, and by ingestion.
When people are exposed to it, rapid, irregular breathing, shortness of breath, decreased pain reflex, and slightly bloody nasal discharge are possible.
Inhalation may cause headache.
Skin exposure to N-Methyl-2-pyrrolidone may cause redness and pain.
N-Methyl-2-pyrrolidone causes a burning sensation in the throat and chest when swallowed.
It can also cause acute solvent syndrome.

 


N-METHYL 2-PYROLIDONE DAMAGE AND TOXICITY TEST

N -Methyl-2-pyrrolidone is a polar solvent with extraordinary properties.
It has a wide application area because it offers very high resolution, high boiling point, low freezing point and ease of use.

In rats, N-Methyl-2-pyrrolidone is rapidly absorbed after inhalation, oral and dermal administration.
N -Methyl-2-pyrrolidone is distributed throughout the organism.
N-Methyl-2-pyrrolidone is eliminated primarily via hydroxylation to polar compounds that are excreted via urine.
Approximately 80% of the administered dose is excreted as N -Methyl-2-pyrrolidone metabolites within 24 hours.

In rodents, a yellow discoloration of urine is observed, possibly dose-dependent.
The main metabolite is 5-hydroxy-N-methyl-2-pyrrolidone.

Studies in humans show comparable results.
Dermal penetration into human skin has been shown to be very rapid.
N -Methyl-2-pyrrolidone is rapidly bioconverted to 5-hydroxy-N-methyl-2-pyrrolidone via hydroxylation.
N -Methyl-2-pyrrolidone is oxidized to N-methylsuccinimide.
This intermediate is further hydroxylated to 2-hydroxy-N-methylsuccinimide.
All of these metabolites are colorless.
The amounts of N -Methyl-2-pyrrolidone metabolites excreted in the urine after inhalation or oral administration represent approximately 100% and 65% of the administered doses, respectively.

N -Methyl-2-pyrrolidone has a low potential for skin irritation and a moderate potential for eye irritation in rabbits.
Application of repeated daily doses of 450 mg/kg body weight to the skin caused painful and severe bleeding and scarring.
These adverse effects were not seen in workers occupationally exposed to pure N -Methyl-2-pyrrolidone.
However, it was observed after dermal exposure to N -Methyl-2-pyrrolidone used in cleaning processes.
No sensitization potential was observed.

 


N -Methyl-2-pyrrolidone is highly polar.
N -Methyl-2-pyrrolidone is miscible with most organic solvents.
N -Methyl-2-pyrrolidone is highly soluble in organic and inorganic substances.
N -Methyl-2-pyrrolidone is miscible with water in all proportions.
It has a higher flash point than similar solvents.
It has a high boiling point, low freezing point and is easy to use.
It is chemically and thermally stable.
N -Methyl-2-pyrrolidone is non-corrosive.


The use of N -Methyl-2-pyrrolidone is particularly suitable for the purification of high-pressure, high-CO2 content synthesis gas in gasification applications.
N -Methyl-2-pyrrolidone generally operates at 5°F to minimize solvent losses.
N-Methyl-2-pyrrolidone has a relatively high vapor pressure compared to DEPG or PC.
The low operating temperature will help minimize solvent losses.
N -Methyl-2-pyrrolidone cannot significantly remove COS.
However, it can be hydrolyzed by the COS,N -Methyl-2-pyrrolidone solvent and then removed.
This process is similar to the DEPG process.


N-Methyl-2-pyrrolidone is prepared by reacting ammonia with methanol at high temperature in the presence of a catalyst and removing the ammonia.
The mixture containing methylamines should have a molar ratio of monomethylamine to γ-BL of at least 1.
It is reacted with gamma-butyrolactone (γ-BL) in a second process step at high temperature and super atmospheric pressure.
Separation of N -Methyl-2-pyrrolidone and unreacted methylamines from the reaction is the first step.
N -Methyl-2-pyrrolidone is denser than water at 1.03 g/cc and its boiling range is 56 ºC.

 

USE OF N-METHYL-2-PYROLIDONE

N-Methyl-2-pyrrolidone, paint and coating removal, petrochemical processing, engineering plastic coatings, agricultural chemicals,
It is a solvent used in various industries and applications such as electronic cleaning and industrial/domestic cleaning.
Due to its good solubility properties, N -Methyl-2-pyrrolidone is used to dissolve a wide variety of polymers.
N -Methyl-2-pyrrolidone is used in the surface treatment of textiles, resins and metal-coated plastics or as a paint remover.

N-METHYL 2-PYROLIDONE DAMAGE AND TOXICITY TEST

N -Methyl-2-pyrrolidone is a polar solvent with extraordinary properties.
It has a wide application area because it offers very high resolution, high boiling point, low freezing point and ease of use.

In rats, N-Methyl-2-pyrrolidone is rapidly absorbed after inhalation, oral and dermal administration.
N -Methyl-2-pyrrolidone is distributed throughout the organism.
N-Methyl-2-pyrrolidone is eliminated primarily via hydroxylation to polar compounds that are excreted via urine.
Approximately 80% of the administered dose is excreted as N -Methyl-2-pyrrolidone metabolites within 24 hours.

In rodents, a yellow discoloration of urine is observed, possibly dose-dependent.
The main metabolite is 5-hydroxy-N-methyl-2-pyrrolidone.

Studies in humans show comparable results.
Dermal penetration into human skin has been shown to be very rapid.
N -Methyl-2-pyrrolidone is rapidly bioconverted to 5-hydroxy-N-methyl-2-pyrrolidone via hydroxylation.
N -Methyl-2-pyrrolidone is oxidized to N-methylsuccinimide.
This intermediate is further hydroxylated to 2-hydroxy-N-methylsuccinimide.
All of these metabolites are colorless.
The amounts of N -Methyl-2-pyrrolidone metabolites excreted in the urine after inhalation or oral administration represent approximately 100% and 65% of the administered doses, respectively.

N -Methyl-2-pyrrolidone has a low potential for skin irritation and a moderate potential for eye irritation in rabbits.
Application of repeated daily doses of 450 mg/kg body weight to the skin caused painful and severe bleeding and scarring.
These adverse effects were not seen in workers occupationally exposed to pure N -Methyl-2-pyrrolidone.
However, it was observed after dermal exposure to N -Methyl-2-pyrrolidone used in cleaning processes.
No sensitization potential was observed.


It is imperative to replace these toxic substances with environmentally friendly alternatives.
Therefore, identifying a green solvent that can dissolve the polymer of interest is only a prerequisite.
Because the resulting membrane must demonstrate competitive performance in order to be adopted by the membrane industry.
Additionally, environmental regulations now restrict the use of toxic solvents.
In particular, REACH has classified DMF, DMAc and NMP as substances of very high concern.


A large body of chemistry has been developed on the reactions of strong nucleophiles with the solvent N -Methyl-2-pyrrolidone.
High purity, low amine and low trace metal grades are taken.
N -Methyl-2-pyrrolidone is sold in the electronics industry and pharmaceutical industry.
N -Methyl-2-pyrrolidone is also used as the reaction medium for polyamide-imide resins in wire coatings.
N -Methyl-2-pyrrolidone is used as a solvent for urethanes and epoxies in water-based coatings.
N-Methyl-2-pyrrolidone is a solvent used in a variety of products.
The average consumer is likely to encounter this situation with paint strippers, although safer alternatives are available.
N -Methyl-2-pyrrolidone has been closely linked to developmental effects, including miscarriage.

The US Environmental Protection Agency (EPA) identifies N -Methyl-2-pyrrolidone as a developmental toxicant.
In 2017, the EPA proposed banning the use of this chemical in paint stripping.
But it later scrapped the proposal under industry pressure.
In 2021, he officially announced that he was withdrawing the offer.


N -Methyl-2-pyrrolidone is absorbed through the skin.
N-Methyl-2-pyrrolidone is a severe irritant; "It is primarily an irritant but may cause severe contact dermatitis due to prolonged contact.
Experimental animals experience drowsiness and difficulty breathing after breathing.
Fetal loss and birth defects have been found in some animal studies after high doses during early pregnancy.
N -Methyl-2-pyrrolidone is a cyclic amide used as a solvent, catalyst, formulating agent and graphite remover.
Significant absorption of N-Methyl-2-pyrrolidone occurs through the skin.
2-HMSI can be used for biological monitoring of employees.
In high-dose animal studies, adverse effects include CNS depression and changes in the liver, kidneys, and blood cells.
N -Methyl-2-pyrrolidone is a skin and eye irritant.


N-Methyl-2-Pyrrolidone finds its application in the following areas, among others:


Petrochemical processing:
N-Methyl-2-pyrrolidone is used as an extraction medium in various industrial processes due to its affinity for unsaturated hydrocarbons and aromatics.
for example butadiene recovery, BTX extraction, mineral oil purification, ...

To demonstrate the strong selectivity of N -Methyl-2-pyrrolidone towards acetylene, the table below shows the solubility of acetylene in various solvents.

Electronic:
N-Methyl-2-pyrrolidone is used as a photoresist stripper for degreasing and cleaning.
NMP, FCCL is a solvent for the production of polyamide/polyimide wire enamels, epoxy and polyurethane coatings.

Medicine:
N -Methyl-2-pyrrolidone solvent can be used as extraction medium.

Industrial and household cleaning:
N-Methyl-2-pyrrolidone is used in paint removal, graffiti removers, oven cleaners, automotive and industrial cleaner formulations, ...

Agricultural chemicals:
N -Methyl-2-pyrrolidone can be used as a solvent or formulation agent during synthesis.

 

 


SYNONYMS


1-Methyl-2-pyrrolidinone;
1-Methyl-2-pyrrolidone;
1-Methyl-5-pyrrolidinone;
1-Methylazacyclopentan-2-one;
1-Methylpyrrolidinone;
1-Methylpyrrolidone;
2-Pyrrolidinone, 1-methyl-;
M-Pyrrole;
Methylpyrrolidone;
N-Methyl-2-pyrrolidinone;
N-Methyl-2-pyrrolidone;
N-Methyl-gamma-butyrolactam;
N-Methylpyrrolidinone;
N-Methylpyrrolidone;
NMP;
Norleucine, 5-oxo-,
DL;

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