N-METHYL-2-PYRROLIDONE

Chemical Identity
IUPAC Name: 1-Methylpyrrolidin-2-one
CAS Number: 872-50-4
Molecular Formula: C₅H₉NO
Synonyms: N-Methyl-2-pyrrolidone, N-Methylpyrrolidone, N-Methylpyrrolidinone, Pharmasolve
SMILES Notation: CN1CCCC1=O
PubChem CID: 13387
ECHA InfoCard: 100.011.662
UNII: JR9CE63FPM
ChEMBL ID: 12543
KEGG Compound ID: C11118

Physical and Chemical Properties
Appearance: Colorless to pale yellow liquid
Density: 1.028 g/cm³
Melting Point: −24°C
Boiling Point: 202–204°C
Flash Point: 91°C
Solubility: Miscible with water; soluble in ethanol, acetone, diethyl ether, ethyl acetate, chloroform, and benzene
Log P (Octanol-Water Partition Coefficient): −0.40
Dipole Moment: 4.09 D
NMP is a polar aprotic solvent with a high dielectric constant, making it effective in dissolving a wide range of polar and nonpolar compounds.

Synthesis Methods
NMP is primarily synthesized through the reaction of gamma-butyrolactone (GBL) with methylamine. This process involves the nucleophilic attack of methylamine on the lactone ring, followed by cyclization to form the lactam structure. 
The reaction typically requires heating and may be catalyzed by acids or bases to enhance yield and selectivity.

Applications
Industrial and Commercial Uses
Solvent in Chemical Processes: NMP is employed as a solvent in various chemical reactions, including polymerization and extraction processes.
Electrolyte in Lithium-Ion Batteries: Utilized in the preparation of electrolytes for lithium-ion batteries due to its high dielectric constant and ability to dissolve salts.
Polymer Processing: Acts as a solvent for polymers such as polyvinylidene fluoride (PVDF) and polyimide, facilitating their processing and fabrication.
Paints and Coatings: Incorporated into formulations for paints and coatings to improve application properties.
Pharmaceuticals: Serves as a solvent in the formulation of certain pharmaceutical products.

Emerging Applications
Nanotechnology: Investigated for use in the dispersion of nanoparticles and as a medium in nanocomposite synthesis.
Agricultural Chemicals: Explored as a solvent for agrochemicals, enhancing the efficacy and stability of formulations.

Safety Precautions
Personal Protective Equipment (PPE): Use of gloves, safety goggles, and respiratory protection is recommended when handling NMP.
Ventilation: Ensure adequate ventilation in areas where NMP is used to minimize inhalation risks.
Storage: Store in a cool, dry place away from incompatible materials such as strong acids and bases.

Environmental and Regulatory Considerations
NMP has been identified as a substance of concern due to its potential environmental and health impacts. Regulatory bodies have established guidelines and regulations to manage its use and minimize risks.
Regulatory Status
European Union: Listed under REACH Regulation with specific restrictions on its use in consumer products.
United States: Subject to evaluation by the Environmental Protection Agency (EPA) under the Toxic Substances Control Act (TSCA).
Australia: Assessed by the National Industrial Chemicals Notification and Assessment Scheme (NICNAS) for potential health risks.
Research and Development
Ongoing research focuses on:
Development of Safer Alternatives: Efforts to identify and synthesize solvents with similar properties but reduced toxicity.
Environmental Impact Studies: Assessing the long-term effects of NMP on ecosystems and exploring remediation strategies.
Industrial Applications: Investigating novel uses of NMP in various industries, including biotechnology and materials science.

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