Methyl Pyrrolidone, N-Methyl Pyrrolidon, NMP, 872-50-4

Methyl Pyrrolidone, N-Methyl Pyrrolidon, NMP, 872-50-4

N-METHYL-2-PYRROLIDONE (NMP)
PRODUCT IDENTIFICATION INFORMATION

CHEMICAL STRUCTURE

N-Methyl-2-pyrrolidone (NMP)

O
║
C
/
CH₂ CH₂
| |
CH₂ CH₂
\ /
N—CH₃

Molecular Formula: C₅H₉NO
SMILES: CN1CCCC1=O
InChI: InChI=1S/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3
InChIKey: SECXISVLQFMRJM-UHFFFAOYSA-N
Structure: Five-membered lactam ring (pyrrolidone) with a methyl group attached to the nitrogen atom; Dipolar aprotic solvent.

SECTION 1: CHEMICAL IDENTITY AND DESCRIPTION

SECTION 2: PHYSICAL AND CHEMICAL PROPERTIES

SECTION 3: SOLVENT COMPARISON

SECTION 4: CHEMICAL PROPERTIES AND REACTIVITY

SECTION 5: PRODUCTION METHODS

Method 1: Gamma-Butyrolactone (GBL) and Methylamine Process

Reaction: C₄H₆O₂ (GBL) + CH₃NH₂ → C₅H₉NO (NMP)

Description: Gamma-butyrolactone (GBL) is reacted with methylamine (aqueous or gaseous) under high temperature and pressure (200-300°C, 30-50 bar); The reaction proceeds through ring opening followed by cyclization; Product is purified by distillation (dehydration and fractionation). Most common and economical industrial method.

Method 2: Succinic Anhydride and Methylamine Process

Reaction: Succinic anhydride + CH₃NH₂ → N-methylsuccinimide → NMP (hydrogenation)

Description: Succinic anhydride is reacted with methylamine to form N-methylsuccinimide; N-methylsuccinimide is hydrogenated (catalytic hydrogenation) to produce NMP; Less common, used for specific high-purity grades.

Method 3: Dehydrocyclization of 1,4-Butanediol with Methylamine

Process: 1,4-Butanediol + CH₃NH₂ → NMP (catalytic dehydrocyclization)

Description: 1,4-Butanediol and methylamine are reacted over a catalyst (copper, nickel or palladium-based); Dehydrocyclization reaction produces NMP and water; Used in some industrial processes.

Method 4: Furfural Route (Bio-based NMP)

Process: Furfural → GBL → NMP

Description: Furfural (from biomass) is converted to GBL; GBL is reacted with methylamine to produce NMP; This route produces bio-based NMP with lower carbon footprint; Gaining importance due to sustainability concerns.

SECTION 6: FUNCTIONAL PROPERTIES AND MECHANISM OF ACTION

SECTION 7: MAIN APPLICATION AREAS

SECTION 8: QUALITY SPECIFICATIONS

SECTION 9: TOXICOLOGICAL PROFILE

SECTION 10: GHS CLASSIFICATION AND LABELING

GHS Classification (in accordance with CLP and UN GHS):

Signal Word: DANGER

Hazard Pictograms: GHS05 (Corrosion), GHS07 (Exclamation Mark), GHS08 (Health Hazard)

Hazard Statements (H-Codes):

EU Risk & Safety Phrases (Old System):

NFPA 704 Hazard Classification:

SECTION 11: PRECAUTIONARY STATEMENTS (P-CODES)

SECTION 12: FIRST AID MEASURES

SECTION 13: FIREFIGHTING MEASURES

SECTION 14: STORAGE AND SHELF LIFE

SECTION 15: PACKAGING OPTIONS

SECTION 16: TRANSPORT INFORMATION

SECTION 17: REGULATORY STATUS

SECTION 18: OTHER NAMES AND SYNONYMS

SECTION 19: SUMMARY TABLE

SECTION 20: CRITICAL WARNINGS AND BEST PRACTICES

CRITICAL WARNINGS:

• Reproductive toxin (H360FD) – May damage fertility and the unborn child. Men and women of childbearing age must take special precautions. Pregnant women must avoid exposure.

• Harmful if swallowed (H302) and inhaled (H332). Avoid ingestion and inhalation. Use with adequate ventilation.

• Causes serious eye irritation (H319). Wear eye protection. In case of eye contact, rinse with plenty of water and seek medical attention.

• Readily absorbed through skin. Use appropriate skin protection (impervious gloves). Avoid prolonged or repeated skin contact.

• Combustible liquid (flash point 91°C). Keep away from heat, sparks, and open flames.

• Hygroscopic – absorbs moisture from air. Keep containers tightly closed. Protect from moisture.

• Incompatibilities: Strong oxidizing agents (violent reaction, fire risk), strong acids (hydrolysis), strong bases (ring opening), isocyanates, halogen compounds.

• REACH restricted substance – EU Annex XVII, Entry 71 restricts use of NMP in certain applications; Check local regulations before use.

• Banned in cosmetic products under EU Cosmetics Regulation (Annex II).

BEST PRACTICE RECOMMENDATIONS:

Lithium-Ion Battery Production: Use as electrode coating solvent for PVDF binder dissolution; Typical usage: 60-80% of electrode slurry formulation; Use high-purity electronic grade to avoid contamination; Avoid moisture (water causes PVDF gelation); NMP can be recovered and recycled via distillation; Ensure proper worker protection (PPE, local exhaust ventilation).

Chemical & Polymer Industry: Use as solvent for high-performance polymers (PVDF, PAN, PEEK, polyamides, polyimides); Use as reaction medium in organic synthesis; Excellent solvent for alkylation, amidation, and cross-coupling reactions; Recover NMP by distillation for cost efficiency and environmental compliance.

Pharmaceutical Industry: Use as co-solvent and penetration enhancer in transdermal formulations; Use in API dissolution (pharmaceutical grade Pharmasolve); Ensure GMP compliance; Use only in controlled environments with strict hygiene standards; Avoid use if safer alternatives are available.

Petrochemical & Refining: Use as selective solvent for 1,3-butadiene and acetylene recovery; Use in H₂S absorption for hydrodesulfurization; Optimize solvent recovery systems for efficiency.

Paints & Coatings: Use as solvent for pigment dispersion; Use as paint stripper (effective on metal and plastic surfaces); Use for resin viscosity control; Follow VOC regulations; Consider alternative solvents for restricted applications.

Electronics Industry: Use for circuit board cleaning (photolithography residue removal); Use as surface treatment solvent; Use electronic grade for semiconductor applications; Avoid particulate contamination.

Alternative Solvents (for restricted applications): Consider DMSO (lower reproductive toxicity) for many applications; Consider DMF (similar properties, but also regulated); Consider GBL (similar properties, NMP precursor); Consider Cyrene (bio-based, safer alternative); Consider Sulfolane (petrochemical applications); Consider Propylene Carbonate (lithium battery applications); Selection depends on specific application requirements.

Handling: Use in well-ventilated areas (local exhaust ventilation); Avoid skin contact – wear impervious gloves (nitrile, neoprene, butyl); Avoid eye contact – wear safety goggles; Use closed systems when possible; Use respiratory protection (organic vapor cartridge) if ventilation inadequate.

Personal Protective Equipment: Chemical-resistant gloves (nitrile, neoprene, butyl – breakthrough time >8 hours), chemical splash goggles (face shield recommended), protective clothing (impervious), NIOSH-approved respirator with organic vapor cartridge (if ventilation inadequate), safety shower and eyewash station nearby.

Hygiene: Wash hands thoroughly after handling; Do not eat, drink, or smoke while using; Remove contaminated clothing and wash before reuse; Shower after handling; Pregnant women and women of childbearing age should avoid exposure.

Storage: Store in tightly closed, corrosion-resistant containers (stainless steel, aluminum, HDPE, glass); Store in a cool, dry, well-ventilated area; Use inert atmosphere (nitrogen) to prevent moisture pick-up; Keep away from heat, sparks, open flames, and direct sunlight; Store locked up (due to reproductive toxicity); Separate from incompatible materials; Shelf life: 24-36 months under proper conditions.

Spill Management: Evacuate area; Wear full protective equipment; Ventilate area; Contain spill with inert absorbent material (sand, vermiculite); Prevent from entering drains or waterways; Collect and place in suitable sealed container; Dispose of as hazardous waste.

Disposal: Dispose of in accordance with local, regional, and national regulations; NMP waste is considered hazardous (toxic, corrosive); Consider solvent recovery and recycling; Do not discharge to sewers without treatment; Incineration in compliance with regulations.

SPECIAL NOTE ON REGULATORY RESTRICTIONS:

• EU REACH Annex XVII, Entry 71: NMP is restricted for use in certain applications. Restrictions apply to:

  • Professional and industrial uses (risk assessment required)

  • Uses where concentration > 0.3% in products

  • Specific uses require authorization (supply chain communication)

• EU Cosmetics Regulation: NMP is banned in cosmetic products (Annex II, Entry 1272).

• California Proposition 65: Listed as reproductive toxin (female reproductive).

• US EPA: Listed as Hazardous Air Pollutant (HAP). Regulated emissions.

• China: Restricted in certain electronic and manufacturing applications.

• Check local regulations before use, as restrictions vary by country and application.

SPECIAL NOTE ON ALTERNATIVE SOLVENTS:

Due to regulatory restrictions and health concerns, NMP alternatives are increasingly used:

Selection Criteria:

• Toxicity and environmental impact (DMSO, Cyrene offer lower health risks)

• Solvency power (DMF, Sulfolane are strong polymer solvents)

• Application requirements (lithium batteries → Propylene Carbonate)

• Regulatory compliance (REACH restrictions)

• Cost and availability

LEGAL DISCLAIMER:
The information provided in this document is based on our current knowledge and experience and is presented in good faith. However, as all conditions of use are beyond our control, it does not constitute a binding specification or warranty. This Technical Data Sheet is for informational purposes only. Users are responsible for testing the suitability for their own applications. For complete safety, storage, use, handling, waste, and regulatory compliance information, please refer to the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier. Special attention must be paid to regulatory restrictions – NMP is a restricted substance under EU REACH (Annex XVII, Entry 71).