N-methyl-2-pyrrolidone (NMP) is an organic compound which is mainly used as a solvent in industry. The substance is produced from γ-butyrolactone and methylamine under high pressure and at high temperatures in large-scale processes, the only by-product being water. Alternatively, N-methyl-2-pyrrolidone can be obtained from methylamine and acrylonitrile or by the hydrogenation of N-methylsuccinimide.
The compound is used as a heat resistant solvent for epoxies, acrylates, polyimides, polyvinyl chloride (PVC), polyamideimide and other polymers. N-methylsuccinimide is used, among other things, in the production of polyurethane foam, in the production of lithium-ion batteries, in the surface treatment of textiles, as a paint remover and for the extraction of acidic compounds in gas scrubbing.
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CAS no. 872-50-4
EINECS no. 212-828-1
Molecular formula: C5H9NO
Synonyms: 1-Methyl-2-pyrrolidone, N-Methyl-2-pyrrolidinone, 1-Methylpyrrolidin-2-one, N-Methylbutyrolactam, N-Methyl-γ-lactam, Methyl Pyrrolidone, NMP
Areas of application: Solvent for polymers such as acrylates, polyimides, epoxies, polyvinyl chloride (PVC) and polyamideimide, used in lithium-ion battery manufacture, textile processing and other industrial applications
N-methyl-2-pyrrolidone (NMP) is a cyclic compound that contains nitrogen. Characteristic of the structure of the substance are four carbon atoms, which are connected to a nitrogen atom to form a pentagonal ring structure. The nitrogen atom is also bonded to a methyl group outside the ring. An adjacent carbon atom from the ring structure has a double bonded oxygen atom. The resulting structural component of nitrogen, carbon and the double bond to an oxygen atom corresponds to an intramolecular amide group. N-methyl-2-pyrrolidone can thus be described as a lactam, more precisely as the γ-lactam of m-methylaminobutyric acid. The lactam ring is very stable and can only be opened by reacting with strong bases and acids.
Under normal storage conditions, N-methyl-2-pyrrolidone (NMP) exists as a liquid compound with a colorless to slightly yellow appearance. The substance is hygroscopic and attracts moisture. N-methyl-2-pyrrolidone has a slight, amine-like inherent odor. The substance is hardly volatile, but tends to form aerosols in high humidity.
The compound is completely miscible with water. N-methyl-2-pyrrolidone is also very soluble in organic solvents such as acetone, ethanol, chloroform, benzene, diethyl ether and ethyl acetate. A special property of the substance is its glass-like refractive index. As a result, pipettes and rods made of glass are hardly visible when they are in the liquid. N-methyl-2-pyrrolidone boils at a temperature of 203 °C and solidifies to a solid below its melting point of -24 °C. Liquid or dissolved in water, N-methyl-2-pyrrolidone is a weak base.
N-methyl-2-pyrrolidone (NMP) is sensitive to light and air. It can gradually be converted into N-methylsuccinimide by oxidation. The compound reacts with strong oxidizing agents, strong acids and strong bases, generating a lot of heat. When storing the substance, it should be noted that N-methyl-2-pyrrolidone attacks containers and seals made of plastic and rubber.
The substance is flammable but does not ignite easily. However, at temperatures above the flash point of 86 °C, the vapors of the compound can form explosive vapor-air mixtures with the ambient air. Since the vapors of the substance are heavier than air, they can initially collect on the ground unnoticed and spread in the work rooms, so that remote ignition is possible. When processing N-methyl-2-pyrrolidone, it is therefore important to ensure a sufficient safety distance from sources of ignition such as sparks, electrical discharges, hot surfaces and open flames. Dangerous and harmful gases such as carbon monoxide, carbon dioxide, hydrogen cyanide and nitrogen oxides are produced during combustion and thermal decomposition of the substance.
N-methyl-2-pyrrolidone (NMP) poses acute and chronic health hazards. Prolonged contact with the compound causes redness, irritation, swelling and blistering of the skin. Affected body areas should be washed thoroughly with water. If symptoms persist, seek medical treatment. Concentrated solutions, vapors and aerosols can cause severe eye irritation, which can temporarily impair vision. After contact with the compound, the eye should be rinsed immediately under running water. An ophthalmological examination must then be arranged.
Inhalation of N-methyl-2-pyrrolidone vapors or aerosols may cause painful irritation in the nose and throat, accompanied by coughing and sneezing. Swallowing the substance causes painful irritation of the mucous membranes and gastrointestinal symptoms such as vomiting and nausea. If N-methyl-2-pyrrolidone is absorbed into the metabolism, general symptoms such as headaches and malaise, impairment of the central nervous system and disturbances in liver and kidney function are to be expected.
The compound is considered to be slightly hazardous to water and can damage aquatic organisms. Prevent N-methyl-2-pyrrolidone from entering the environment. In case of leakage of large quantities into soil, drains or waterways, the local authorities should be informed. The substance is not subject to any special transport regulations.