2-Pyrrolidone, 2-Pyrrolidinone, Butyrolactam, γ-Butyrolactam, Aminobutyrolactam, 2-Ketopyrrolidine, Gamma-Butyrolactam, 616-45-5
2-PYRROLIDONE (CAS: 616-45-5)
CAS Number: 616-45-5
EC Number (EINECS): 210-483-1
Molecular Formula: C₄H₇NO
Molecular Weight: 85.10 g/mol
UNSPSC Code: 12352200
SECTION 1: PRODUCT IDENTIFICATION AND CHEMICAL IDENTITY
| Parameter |
Description |
| Chemical Name (IUPAC) |
Pyrrolidin-2-one |
| Other Names |
2-Pyrrolidone, 2-Pyrrolidinone, Butyrolactam, γ-Butyrolactam, Aminobutyrolactam, 2-Ketopyrrolidine, 2-Pyrrolidinone, gamma-Butyrolactam |
| CAS Number |
616-45-5 |
| EC Number (EINECS) |
210-483-1 |
| Molecular Formula |
C₄H₇NO |
| Molecular Weight |
85.10 g/mol |
| Chemical Class |
Lactam (pyrrolidone derivative) |
| Structure |
Five-membered lactam ring (cyclic amide) |
| Appearance |
Colorless to pale yellow liquid |
| Odor |
Mild, amine-like |
| UNSPSC Code |
12352200 |
SECTION 2: PHYSICAL AND CHEMICAL PROPERTIES
| Property |
Value / Range |
| Molecular Formula |
C₄H₇NO |
| Molecular Weight |
85.10 g/mol |
| Appearance |
Colorless to pale yellow liquid |
| Odor |
Mild, amine-like |
| Melting Point |
23 - 25°C |
| Boiling Point |
~245°C |
| Density (25°C) |
~1.12 g/cm³ |
| Refractive Index (n²⁰D) |
1.485 |
| Flash Point |
~113°C |
| Vapor Pressure (20°C) |
0.01 mmHg |
| Solubility in Water |
Completely miscible |
| Solubility in Organic Solvents |
Completely miscible with most organic solvents |
| pH (100 g/L in water) |
9 - 11 (basic) |
| Explosion Limits |
1.8% - 16.6% (v/v) |
| Autoignition Temperature |
~410°C |
| Viscosity (25°C) |
~13 cP |
| Dielectric Constant (25°C) |
~44 |
| Water Hazard Class (WGK Germany) |
WGK 1 (low hazard to water) |
SECTION 3: SOLUBILITY PROFILE
| Solvent |
Solubility |
Condition |
| Water |
Completely miscible |
All temperatures |
| Methanol |
Completely miscible |
- |
| Ethanol |
Completely miscible |
- |
| Acetone |
Completely miscible |
- |
| Ethyl Acetate |
Completely miscible |
- |
| Chloroform |
Completely miscible |
- |
| Toluene |
Completely miscible |
- |
| Benzene |
Completely miscible |
- |
| Ether |
Completely miscible |
- |
| Aliphatic Hydrocarbons |
Limited |
- |
Critical Note: 2-Pyrrolidone is completely miscible with water and most organic solvents. Its high polarity and ability to form hydrogen bonds make it an excellent solvent for a wide range of applications.
SECTION 4: CHEMICAL PROPERTIES AND REACTIONS
| Property |
Description |
| Chemical Class |
Lactam (cyclic amide) |
| Functional Group |
Amide (lactam ring) |
| Reactivity |
Moderate; can undergo ring-opening reactions |
| Ring-Opening Reactions |
Hydrolysis in acidic/basic conditions to γ-aminobutyric acid (GABA) derivatives |
| Polymerization |
Reacts with vinyl derivatives to produce PVP (Polyvinylpyrrolidone) |
| N-Alkylation |
Used in production of NMP, NEP, NOP derivatives |
| Solvation |
Excellent solvency for polar and non-polar substances |
| Thermal Decomposition |
> 300°C releases nitrogen oxides (NOₓ), carbon oxides |
| Oxidation |
Can form peroxides; requires careful storage |
4.1. Key Reactions
| Reaction Type |
Description |
| Ring-Opening Hydrolysis |
Acidic/basic media → γ-aminobutyric acid (GABA) |
| N-Alkylation |
Production of NMP, NEP, NOP derivatives |
| Polymerization |
PVP production with vinyl derivatives |
| Complex Formation |
Forms complexes with iodine, iodine-povidone (PVP-I) |
4.2. Stability
| Parameter |
Information |
| Thermal Stability |
Stable under normal conditions |
| Hydrolytic Stability |
Stable at neutral pH; ring-opening in strong acids/bases |
| Peroxide Formation |
Can form peroxides upon exposure to air/light; requires stabilization |
| Incompatibilities |
Strong oxidizers, strong acids, strong bases, air (peroxide formation) |
| Decomposition Products |
Nitrogen oxides (NOₓ), CO, CO₂, ammonia |
SECTION 5: SPECTRAL DATA
| Parameter |
Value |
| FTIR (KBr, cm⁻¹) |
3250 (N-H), 2950 (C-H aliphatic), 1680 (C=O amide), 1450 (C-H bend), 1280 (C-N) |
| ¹H-NMR (CDCl₃, ppm) |
6.80 (s, 1H, N-H), 3.30 (t, 2H, N-CH₂), 2.40 (t, 2H, CH₂-CO), 2.00 (m, 2H, CH₂) |
| ¹³C-NMR (CDCl₃, ppm) |
175.0 (C=O), 42.0 (N-CH₂), 31.0 (CH₂-CO), 29.0 (CH₂) |
| Mass Spectrometry (EI-MS) |
85 [M]⁺, 57 [C₃H₅O]⁺, 56 [C₃H₄O]⁺, 41 [C₃H₅]⁺ |
SECTION 6: PURITY AND QUALITY SPECIFICATIONS
| Parameter |
Standard Grade |
High Purity Grade |
| Purity (GC) |
≥ 99.0% |
≥ 99.5% |
| Appearance |
Colorless to pale yellow liquid |
Colorless liquid |
| Color (APHA) |
≤ 100 |
≤ 50 |
| Density (25°C) |
1.118 - 1.124 g/cm³ |
1.120 - 1.122 g/cm³ |
| Refractive Index (n²⁰D) |
1.484 - 1.486 |
1.485 - 1.486 |
| Water Content (KF) |
≤ 0.5% |
≤ 0.2% |
| Acid Value |
≤ 0.5 mg KOH/g |
≤ 0.2 mg KOH/g |
| Ash Content |
≤ 0.1% |
≤ 0.05% |
| Color (Hazen) |
≤ 100 |
≤ 50 |
| pH (100 g/L in water) |
9 - 11 |
9 - 11 |
SECTION 7: MAJOR APPLICATIONS AND END-USES
7.1. Polymer Production (Primary Application)
| Application |
Function |
Suitability |
| PVP Production |
Key monomer for Polyvinylpyrrolidone (PVP) synthesis |
High |
| Copolymer Production |
Monomer for vinyl pyrrolidone copolymers |
High |
| PVP-Iodine Complex |
Iodine carrier for disinfectants (povidone-iodine) |
High |
7.2. Pharmaceutical Industry
| Application |
Function |
Suitability |
| Racetam Derivatives |
Key intermediate for piracetam, levetiracetam, etc. |
High |
| Ethosuximide |
Production of anticonvulsant drug |
High |
| Pharmaceutical Intermediates |
Building block for active pharmaceutical ingredients |
High |
7.3. Inks and Coatings
| Application |
Function |
Suitability |
| Inkjet Cartridges |
Solvent and binder for ink formulations |
High |
| Printing Inks |
Carrier solvent and dispersant |
High |
| Coatings |
Solvent and coalescent |
High |
7.4. Agricultural Chemicals
| Application |
Function |
Suitability |
| Pesticide Formulations |
Carrier solvent and solubilizer |
High |
| Herbicide Formulations |
Co-solvent |
High |
| Fungicide Formulations |
Solvent |
High |
7.5. Specialty Applications
| Application |
Function |
Suitability |
| Electroplating |
Specialty additive |
High |
| Electronics Cleaning |
Cleaning solvent for electronic components |
High |
| Metal Surface Treatment |
Solvent and additive |
High |
| Chemical Intermediates |
Building block for various syntheses |
High |
SECTION 8: INDUSTRY SUITABILITY MATRIX
| Industry |
Suitability |
Explanation |
| Polymer Production |
High |
Key monomer for PVP and copolymers |
| Pharmaceuticals |
High |
Racetam derivatives, ethosuximide production |
| Inks and Coatings |
High |
Solvent and binder for inkjet formulations |
| Agriculture |
High |
Carrier solvent for pesticide formulations |
| Electroplating |
High |
Specialty additive |
| Electronics |
High |
Cleaning solvent |
| Textiles |
Moderate |
Auxiliary and solvent |
| Cosmetics |
Limited |
Only in specific formulations |
| Food |
Not suitable |
Not used as direct food additive |
SECTION 9: TYPICAL USE LEVELS
| Application |
Typical Use Level |
| PVP Production |
100% (as monomer) |
| Pharmaceutical Synthesis |
10% - 50% of reaction volume |
| Ink Formulations |
5% - 20% (carrier solvent) |
| Agricultural Formulations |
5% - 30% (co-solvent) |
| Electronics Cleaning |
10% - 100% (as pure solvent) |
SECTION 10: OTHER NAMES AND IDENTIFIERS
| Type |
Name / Description |
| IUPAC Name |
Pyrrolidin-2-one |
| Commercial Names |
2-Pyrrolidone, 2-Pyrrolidinone |
| Synonyms |
Butyrolactam, γ-Butyrolactam, Aminobutyrolactam, 2-Ketopyrrolidine, gamma-Butyrolactam, 2-Pyrrolidinone |
| Common Names |
PVP raw material, Ink solvent, Pyrrolidone-based solvent |
| CAS Number |
616-45-5 |
| EC Number |
210-483-1 |
| UNSPSC Code |
12352200 |
SECTION 11: PRODUCTION METHODS
11.1. Main Production Method
| Parameter |
Description |
| Method |
Gamma-butyrolactone (GBL) + Ammonia → 2-Pyrrolidone |
| Temperature |
250 - 290°C |
| Pressure |
0.4 - 1.4 MPa |
| Catalyst |
Magnesium silicate (fixed bed) |
| Yield |
75% - 85% |
| Purity |
≥ 99.5% (after distillation) |
11.2. Alternative Production Methods
| Method |
Description |
| Succinimide Reduction |
Reduction of succinimide |
| Allylamine Carbonylation |
Carbonylation of allylamine |
| Maleic Anhydride |
Reaction with ammonia over Pd-Ru catalyst |
SECTION 12: ALTERNATIVE PRODUCTS
| Alternative |
CAS Number |
Description |
| N-Methyl-2-pyrrolidone (NMP) |
872-50-4 |
Higher boiling point solvent |
| 2-Methyltetrahydrofuran (2-MeTHF) |
96-47-9 |
Bio-based alternative |
| Dimethylformamide (DMF) |
68-12-2 |
Similar polarity solvent |
| Gamma-Butyrolactone (GBL) |
96-48-0 |
Precursor and alternative solvent |
| N-Ethyl-2-pyrrolidone (NEP) |
2687-91-4 |
N-substituted derivative |
SECTION 13: COMPARISON OF PYRROLIDONE DERIVATIVES
| Property |
2-Pyrrolidone |
NMP |
NEP |
NOP |
| N-Substituent |
H (none) |
Methyl |
Ethyl |
Octyl |
| Boiling Point |
245°C |
202°C |
97°C (20 mmHg) |
170°C (15 mmHg) |
| Water Solubility |
Completely miscible |
Completely miscible |
Completely miscible |
Limited (1.2 g/L) |
| pH (1% aq.) |
9-11 |
~7 |
8-9 |
~7 |
| Primary Use |
Monomer, intermediate |
Solvent |
Solvent |
Surfactant, co-solvent |
| Viscosity (25°C) |
~13 cP |
~1.7 cP |
~3.5 cP |
~15 cP |
SECTION 14: TOXICOLOGY AND HEALTH EFFECTS
| Parameter |
Value / Description |
| GHS Classification |
Warning |
| Hazard Statements |
H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation) |
| Precautionary Statements |
P261 (Avoid breathing dust/fume/gas/mist/vapors/spray), P280 (Wear protective gloves/protective clothing/eye protection/face protection), P302+P352 (IF ON SKIN: Wash with plenty of water), P305+P351+P338 (IF IN EYES: Rinse cautiously with water) |
| Oral LD50 (Rat) |
~6,000 mg/kg |
| Dermal LD50 (Rabbit) |
> 2,000 mg/kg |
| Skin Irritation |
Mild irritant |
| Eye Irritation |
Mild irritant |
| Skin Sensitization |
Not sensitizing |
| Mutagenicity |
Negative (Ames test) |
| Carcinogenicity |
Not classified |
| Reproductive Toxicity |
Not classified |
| Target Organs |
Skin, eyes, respiratory system |
SECTION 15: ECOTOXICOLOGY AND ENVIRONMENTAL BEHAVIOR
| Parameter |
Value / Description |
| Fish Toxicity (LC50, 96 hours) |
> 1,000 mg/L |
| Daphnia Toxicity (EC50, 48 hours) |
> 1,000 mg/L |
| Algae Toxicity (EC50, 72 hours) |
> 1,000 mg/L |
| Biodegradability |
Readily biodegradable (OECD 301) |
| Bioaccumulation Factor (BCF) |
Very low (LogP < 1) |
| Hydrolysis |
Stable; ring-opening only in extreme conditions |
| Soil Mobility |
High (water soluble) |
| Bioaccumulation Potential |
Very low |
| Persistence |
Low (readily biodegradable) |
| Water Hazard Class (WGK Germany) |
WGK 1 (low hazard to water) |
Ecotoxicological Summary: 2-Pyrrolidone is readily biodegradable (OECD 301) with very low bioaccumulation potential. It shows very low toxicity to aquatic organisms (LC₅₀ > 1,000 mg/L). Classified as WGK 1 (low hazard to water).
SECTION 16: SAFETY MEASURES AND PERSONAL PROTECTIVE EQUIPMENT
| Parameter |
Information |
| Respiratory Protection |
Organic vapor cartridge (at elevated temperatures or mist formation) |
| Gloves |
Chemically resistant (nitrile, neoprene, butyl rubber) |
| Eye Protection |
Chemical safety goggles |
| Body Protection |
Chemical-resistant apron |
| Ventilation |
Local exhaust ventilation and general ventilation |
| Engineering Controls |
Closed systems when possible; peroxide inhibitors recommended |
SECTION 17: STORAGE INFORMATION
| Parameter |
Information |
| Storage Conditions |
Cool, dry, well-ventilated area |
| Temperature |
Room temperature (15 - 30°C) |
| Container |
Tightly closed, dry, inert containers (glass, stainless steel) |
| Special Requirements |
Store under inert atmosphere (N₂) to prevent peroxide formation |
| Materials to Avoid |
Fire, direct sunlight, strong oxidizers, strong acids, strong bases, air (peroxide formation) |
| Peroxide Formation |
Can form peroxides; add stabilizers if necessary |
| Shelf Life |
12 - 24 months (under recommended conditions) |
| Packaging |
200 kg drum, 1000 kg IBC |
SECTION 18: TRANSPORT INFORMATION
| Parameter |
Information |
| UN Number |
Not regulated (not classified as dangerous goods) |
| Hazard Class |
Not applicable |
| Packing Group |
Not applicable |
| Proper Shipping Name |
2-Pyrrolidone |
| ADR/RID |
Not regulated |
| IMDG Code |
Not regulated |
| IATA (Air) |
Not regulated |
| Marine Pollutant |
No |
| Transport Notes |
Keep away from heat; prevent leakage |
SECTION 19: FIRE-FIGHTING MEASURES
| Parameter |
Information |
| Fire Hazard |
Combustible liquid (flash point ~113°C) |
| Extinguishing Media |
Water fog, foam, CO₂, dry chemical |
| Special Hazards |
When heated, releases nitrogen oxides (NOₓ), CO, CO₂, ammonia |
| Decomposition Products |
Nitrogen oxides (NOₓ), CO, CO₂, ammonia |
| Protective Equipment |
Self-contained breathing apparatus (SCBA), full protective clothing |
| Explosion Risk |
Vapor/air mixtures potentially explosive (1.8% - 16.6% v/v) |
| Water Use |
Prevent fire-fighting water from entering the environment |
SECTION 20: SUMMARY AND CRITICAL WARNINGS
Product Summary
| Parameter |
Value |
| Product |
2-Pyrrolidone |
| CAS |
616-45-5 |
| Appearance |
Colorless to pale yellow liquid |
| Density (25°C) |
~1.12 g/cm³ |
| Boiling Point |
~245°C |
| Water Solubility |
Completely miscible |
| Flash Point |
~113°C |
| Key Industries |
Polymers (PVP), pharmaceuticals, inks, agriculture |
CRITICAL WARNINGS
-
Key Monomer for PVP: 2-Pyrrolidone is the key monomer for Polyvinylpyrrolidone (PVP) production. PVP is widely used in pharmaceuticals (povidone-iodine), cosmetics, food, and industrial applications.
-
High Polarity: 2-Pyrrolidone is a highly polar aprotic solvent. It is completely miscible with water and most organic solvents.
-
Pharmaceutical Intermediate: Key intermediate for racetam derivatives (piracetam, levetiracetam) and ethosuximide production.
-
Peroxide Formation: Can form peroxides upon exposure to air and light. Store under inert atmosphere (N₂) and use stabilizers if necessary.
-
Biodegradability: Readily biodegradable (OECD 301) with very low bioaccumulation potential (LogP < 1). Classified as WGK 1 (low hazard to water).
-
Melting Point: 2-Pyrrolidone is a liquid above 23°C. At room temperatures below 23°C, it solidifies. Heating may be required for handling.
-
Flammability: Combustible liquid with flash point 113°C. Vapor/air mixtures may be explosive at 1.8% - 16.6% (v/v).
-
pH: 2-Pyrrolidone is basic (pH 9-11 in aqueous solution). Handle with appropriate PPE.
-
Storage: Store in cool, dry, well-ventilated areas. Keep away from strong oxidizers, acids, bases, and air. Use inert atmosphere.
-
Not for Food Use: 2-Pyrrolidone is not approved as a direct food additive. Use only in technical, industrial, and pharmaceutical applications (as intermediate).
IMPORTANT DISCLAIMER: This Technical Data Sheet (TDS) is for informational purposes only and is based on available technical data. The user is solely responsible for determining the product's suitability for their specific application and for complying with all applicable local, national, and international regulations. For complete safety, storage, handling, transportation, disposal, and regulatory compliance information, always refer to the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier. Users are responsible for testing the product in their own processes and applications. All local, national, and international regulations must be followed when working with 2-Pyrrolidone.
