N-METHYL-2-PYRROLIDONE

CAS Number: 872-50-4
 EC Number: 212-828-1
 UN Number: Not regulated (but may be classified under specific mixtures)
 Molecular Formula: C₅H₉NO
 Molecular Weight: 99.13 g/mol

 Synonyms:
NMP,1-Methyl-2-pyrrolidone,N-Methylpyrrolidinone,Pharmasolve (trade name),M-Pyrol

Physical and Chemical Properties:
 Colorless to pale yellow liquid with a characteristic amine-like odor. Exhibits exceptional solvent power with a high dipole moment (4.09 D) and dielectric constant (32.2 at 20°C). Key parameters include boiling point 202°C, melting point -24°C, density 1.028 g/cm³ at 25°C, flash point 95°C, and autoignition temperature 346°C. Demonstrutes complete miscibility with water and most organic solvents except aliphatic hydrocarbons. The lactam structure provides chemical stability up to 200°C but undergoes hydrolysis under strongly acidic or basic conditions.
Succinic Acid Route: Via succinic anhydride and methylamine
Maleic Anhydride Route: Hydrogenation followed by amination
Biotechnological Routes: From renewable feedstocks (developmental)
Purification and Quality Grades:
 Crude NMP undergoes sequential purification:
Distillation: Under reduced pressure to remove water and low boilers
Chemical Treatment: With activated carbon and molecular sieves
Final Distillation: High-vacuum fractional distillation
Packaging: Under nitrogen blanket for high-purity grades
Quality Specifications by Grade:
Electronic Grade: >99.95% purity, water <50 ppm, metals <1 ppm total
Pharmaceutical Grade: USP/EP compliance, related substances <0.1%
Industrial Grade: >99.5% purity for general applications
Battery Grade: Specific impurity profile for lithium-ion applications
Global production capacity exceeds 300,000 metric tons annually, with major producers in China (60% of capacity), Europe (BASF, LyondellBasell), and North America (Ashland, Balaji Amines). Pricing varies from $1.5-2.5/kg for industrial grades to $10-20/kg for ultra-high-purity electronic grades.
Comprehensive Application Portfolio
Electronics and Energy Storage (40%):
Lithium-Ion Battery Electrode Processing: As solvent for PVDF binder and cathode active materials (NMC, LFP). Typical formulations contain 50-70% NMP in slurry preparations.
Photoresist Stripping: In semiconductor manufacturing for removing polyimide and other photoresists (typically at 80-100°C).
Wafer Cleaning: For removing post-etch residues and particles.
Case Example: In NMC811 cathode manufacturing, NMP-based slurries (solid content 60-70%) enable uniform coating with controlled porosity, directly impacting energy density and cycle life.
Polymer Processing (25%):
Polymer Solvent: For polyimide, polyamide-imide, PEEK, and PPS processing. Dissolution typically at 15-25% solids at 80-120°C.
Membrane Manufacturing: For phase inversion processes producing PVDF, polysulfone, and PES membranes.
Fiber Spinning: Dry-jet wet spinning of aramid fibers (Kevlar®, Nomex®).
Case Example: In polyimide film production (Kapton®), NMP solutions (15-20% solids) are cast and thermally imidized to produce high-temperature insulating films for aerospace applications.
Pharmaceutical Industry (15%):
API Synthesis: As reaction solvent for nucleophilic substitutions, condensations, and cyclizations.
Extraction Solvent: For natural products and fermentation products.
Crystallization: As anti-solvent or crystallization medium.
Formulation Component: In transdermal patches as penetration enhancer.
Case Example: In the synthesis of atorvastatin, NMP serves as solvent for the key condensation reaction, providing optimal solubility and reaction kinetics.
Chemical Processing (10%):
Gas Purification: For selective removal of acidic gases (CO₂, H₂S) from natural gas and synthesis gas.
Extractive Distillation: For separation of close-boiling hydrocarbons.
Lube Oil Extraction: In refining processes.
Reaction Medium: For organometallic chemistry and polymerization reactions.
Other Applications (10%):
Industrial Cleaning: For heavy-duty degreasing and paint stripping.
Agriculture: As solvent for pesticide formulations.
Petrochemicals: As absorption liquid in acetylene recovery.
Analytical Chemistry: As mobile phase component in HPLC.
Chemical Behavior and Solvent Properties
Solvent Power Parameters:
Hansen Solubility Parameters: δD = 18.0, δP = 12.3, δH = 7.2 MPa¹/²
Reichardt's ET(30): 41.0 kcal/mol (moderately polar)
Kamlet-Taft Parameters: π* = 0.92, α = 0, β = 0.77
Donor Number: 27 kcal/mol (strong Lewis base)
Unique Solvent Characteristics:
High Boiling Point: Enables high-temperature reactions without pressure equipment
Low Volatility: Reduces solvent losses and exposure risks
Thermal Stability: Withstands temperatures to 200°C without decomposition
Wide Liquid Range: -24°C to 202°C
Low Corrosivity: Compatible with most construction materials
Co-solvent Systems:
 NMP frequently combines with:
Water: For solubility tuning and environmental benefits
Alcohols: For polarity adjustment
Aromatic Hydrocarbons: For cost reduction in industrial applications
Ethers: For specific solvation requirements

SAFETY INFORMATION ABOUT N-METHYL-2-PYRROLIDONE

 
 
 
 
 
 
First aid measures:
Description of first aid measures:
General advice:
Consult a physician. 
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
 
If inhaled:
If breathed in, move person into fresh air. 
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately. 
Wash off with soap and plenty of water.
Consult a physician.
 
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
 
If swallowed:
Do NOT induce vomiting. 
Never give anything by mouth to an unconscious person. 
Rinse mouth with water. 
Consult a physician.
 
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
 
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. 
 
Avoid breathing vapours, mist or gas. 
Evacuate personnel to safe areas.
 
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
 
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste. 
Keep in suitable, closed containers for disposal.
 
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
 
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place. 
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
 
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
 
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles. 
Faceshield (8-inch minimum). 
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
 
Skin protection:
Handle with gloves. 
Gloves must be inspected prior to use. 
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product. 
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. 
Wash and dry hands.
 
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
 
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. 
 
If the respirator is the sole means of protection, use a full-face supplied air respirator. 
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. 
Do not let product enter drains.
Discharge into the environment must be avoided.
 
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions. 
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
 
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company. 
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product