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2-PYRROLIDONE

2-pyrrolidone, also known as 2-pyrrolidinone or butyrolactam, is an organic compound consisting of a 5-membered lactam, making it the simplest γ-lactam. 
2-pyrrolidone is a colorless liquid that is miscible with water and most common organic solvents.
2-pyrrolidone itself and it various derivatives, especially N-methylpyrrolidone, have a variety of industrial uses.

CAS Number: 616-45-5
Molecular Formula: C4H7NO
Molecular Weight: 85.1
EINECS Number: 210-483-1

Synonyms: pyrrolidin-2-one, 2-Pyrrolidinone, 616-45-5, 2-PYRROLIDONE, Pyrrolidone, Butyrolactam, 2-Oxopyrrolidine, Pyrrolidon, PYRROLIDINONE, 2-Ketopyrrolidine, 2-Pyrol, gamma-Butyrolactam, alpha-Pyrrolidinone, 4-Aminobutyric acid lactam, gamma-Aminobutyric lactam, gamma-Aminobutyrolactam, .alpha.-Pyrrolidone, 2-Tetrahydropyrrolone, gamma-Aminobutyric acid lactam, .gamma.-Aminobutyrolactam, Butanoic acid, 4-amino-, lactam, Pyrrolidone-2, alpha-Pyrrolidone, pyrrolid-2-one, NSC 4593, NSC 8413, pyrrolidine-2-one, MFCD00005270, azacyclopentan-2-one, .gamma.-Butyrolactam, .alpha.-Pyrrolidinone, KKL5D39EOL, .gamma.-Aminobutyric lactam, DTXSID8027246, CHEBI:36592, NSC-4593, NSC-8413, Butanoic acid, lactam, 2-Pyrrolidinone, 99%, WLN: T5MVTJ, DTXCID707246, Pyrrolidon [German], CAS-616-45-5, HSDB 2652, EINECS 210-483-1, UNII-KKL5D39EOL, butyrolactim, pyrollidone, 2pyrrolidinone, a-pyrrolidone, 2-pyrollidinone, 2-pyrolidinone, 2-pyrrolidinon, Aminobutyrolactam, Soluphor P, pyrrolidin-2-on, 2-pyrrolidin-one, pyrolidine-2-one, pyrollidin-2-one, Tetrahydropyrrolone, 2-oxo-pyrrolidine, Aminobutyric lactam, 2-Azacyclopentanone, 2-Oxo-4-butyrolactam, Aminobutyric acid lactam, 1-azacyclopentan-2-one, 2-Pyrrolidone-Butyrolactam, EC 210-483-1, 2-pyrrolidone for synthesis, 2-Pyrrolidinone, >=99%, NCIOpen2_000687, PYRROLIDONE [MART.], 2-PYRROLIDONE [MI], 2-PYRROLIDONE [HSDB], CHEMBL276849, FEMA NO. 4829, .gamma.-Aminobutyric acid lactam, NSC4593, NSC8413, 2-Pyrol4-aminobutyric acid lactam, PYRROLIDONE [EP MONOGRAPH], Pyrrolidin-2-one (2-Pyrrolidone), BCP26683, HY-Y1831, EINECS 245-100-7, Tox21_201630, Tox21_303259, STL197473, AKOS000119138, FG-0424, 2-PYRROLIDONE MFC4 H7 N1 O1, NCGC00249089-01, NCGC00257072-01, NCGC00259179-01, PD078398, POVIDONE IMPURITY B [EP IMPURITY], 2-Pyrrolidinone, purum, >=98.0% (GC), COPOVIDONE IMPURITY A [EP IMPURITY], Pyrrolidin-2-one (1-aza-2-cyclopentanone), CS-0019427, NS00007032, P0575, EN300-19119, A15700, D96808, Q285640, F0001-1634, Z104472846, Hydrogen tribromide, compound with pyrrolidin-2-one (1:3), Pyrrolidone, European Pharmacopoeia (EP) Reference Standard, InChI=1/C4H7NO/c6-4-2-1-3-5-4/h1-3H2,(H,5,6.2-Pyrrolidone Butyrolactam;2-AZACYCLOPENTANONE;2-P;2-KETOPYRROLIDINE;ALPHA-PYRROLIDONE;PIPERIDINIC ACID LACTAM;2-Oxopyrrolidine;2-Pyrol

2-pyrrolidone is produced industrially almost exclusively by treating aqueous gamma-butyrolactone with ammonia at a temperature of 250–290 °C and pressures ranging from 0.4–1.4 MPa over solid magnesium silicate catalysts.
The reaction is carried out in a tubular reactor which is packed with the solid catalyst. 
The latter is arranged as a fixed bed and the reaction is carried out in the vapor phase.
 
After subsequent distillation and purification, the desired 2-pyrrolidone is obtained with a purity of 99.5%.
Alternative routes include the catalytic or electrochemical reduction of succinimide, the carbonylation of allylamine, the hydrogenation of succinonitrile under hydrolytic conditions, and the reaction of maleic or succinic anhydride in aqueous ammonia with Pd–Ru-catalysts.
In 2010, the worldwide demand for 2-pyrrolidone was estimated to be 32.000 t. 

Important manufacturers of 2-pyrrolidone are BASF and ISP (International Speciality Products, now Ashland Inc.).
2-Pyrrolidone, also known by its IUPAC name as pyrrolidin-2-one, is a heterocyclic organic compound characterized by a six-membered ring with one nitrogen atom and one oxygen atom. 
2-pyrrolidone is a colorless to slightly yellow liquid that has a faint, characteristic odor. 

This compound is widely used in various industries, especially in the production of pharmaceuticals, cosmetics, and agrochemicals. 
2-pyrrolidone is a versatile solvent due to its ability to dissolve a wide range of substances, including salts, metals, and polymers. 
Additionally, 2-pyrrolidone serves as a key precursor in the synthesis of other chemicals, such as N-vinylpyrrolidone, which is used in polymer production and as a component in certain hair care products.

2-Pyrrolidone is used as constituent of pharmaceutical preparations.
2-Pyrrolidone is used in Ink, toner, and colorant products
2-Pyrrolidone is used as a starting material in the synthesis of polyvinylpyrrolidone

2-Pyrrolidone is a widely-used solvent with outstanding characteristics.
2-Pyrrolidone is miscible with almost all other organic solvents
2-Pyrrolidone has a high boiling point.

2-Pyrrolidone is a compound containing nitrogen in a 5-membered ring.
2-Pyrrolidone has the following characteristics:
Miscible in almost all organic solvents (alcohols, ethers, esters, aromatic hydrocarbons, chlorinated hydrocarbons, carbon disulde, etc.)

2-Pyrrolidone carboxylic acid, also known as pyroglutamic acid, is a derivative of the glutamine and glutamate.
2-Pyrrolidone is contained in many kinds of proteins including bacteriorhodopsin.
2-Pyrrolidone is a nonessential nutrient which can be normally generated during the glutathione cycle process inside the human body.

2-pyrrolidone is also contained in fruits and vegetables.
2-Pyrrolidone has many physiological functions and healthy eects.
2-Pyrrolidone's L-form can increase the activity o neurotransmitter acetylcholine and can be used in the production of the neurotransmitters gramma-aminobutyric acid (GABA) as well as glycine.

Based on this, 2-Pyrrolidone acid is benecial to brain function, being capable of supporting memory and learning as well as alleviating anxiety.
In addition, 2-Pyrrolidone's sodium-form product (sodium pyroglutamate), as a humectant, can be used for dry skin and hair products.
2-pyrrolidone undergoes the reactions of a typical lactam, e.g. ring opening, attack on the carbonyl group, and replacement of hydrogens alpha to the carbonyl group.

Strong acids and bases catalyze the hydrolysis of 2-pyrrolidone to 4-aminobutanoic acid (GABA).
The hydrogen atom on the nitrogen atom is easily replaced by alkylation reactions with alkyl halide or sulfates, or reaction with acid anhydrides, acyl halides, ethylene oxide, and styrene.
Condensation reactions with secondary amines and alcohols, and O-alkylation reactions occur at the carbonyl group.

In the presence of anionic catalyst systems, 2-pyrrolidone is polymerized to polypyrrolidone, nylon-4.
2-Pyrrolidone occurs as a colorless or slightly grayish liquid, as white or almost white crystals, or colorless crystal needles.
2-Pyrrolidone has a characteristic odor.

2-Pyrrolidone is a widely used organic polar solvent for various applications.
2-Pyrrolidone is also an intermediate in the manufacture of polymers.
2-Pyrrolidone is prepared from butyrolactone by a Reppe process, in which acetylene is reacted with formaldehyde.

The simplest member of the class of pyrrolidin-2-ones, consisting of pyrrolidine in which the hydrogens at position 2 are replaced by an oxo group.
The lactam arising by the formal intramolecular condensation of the amino and carboxy groups of gamm -aminobutyric acid.
N-methyl-2-pyrrolidone and 2-pyrrolidone are utilized in petroleum rening to selectively extract aromatics from paranic hydrocarbons.

2-Pyrrolidone is used as a plasticizer and coalescing agent for acrylic latices and acrylic/styrene copolymers in emulsion coatings, i.e. oor waxes.
A linear high molecular weight polyamide polymer of 2-pyrrolidone, nylon-4, is used as a textile ber, injection molding compound, and lm-forming polymer
2-Pyrrolidone is incompatible with oxidizing agents and strong acids.

2-Pyrrolidone is used as a cosolvent and plasticiser in aqueous coatings.
As a setting agent, 2-Pyrrolidone is used for acrylic emulsions and acrylic/styrene copolymers in oor polishes
2-Pyrrolidone is used as a co-solvent for water-based ink formulations

2-Pyrrolidone is an organic synthesis intermediate in the pharmaceutical industry, e.g. Piracetam; and as a solvent for animal injection.
2-Pyrrolidone is a precursor of N-vinylpyrrolidone (NVP).
2-Pyrrolidone also nds application as a solvent in the manufacture of membrane lters for e.g. sterile ltration of drugs such as pharmaceutical proteins, wine ltration systems

2-Pyrrolidone (2-Pyrrolidinone,2-Pyrol) is an organic compound consisting of a ve-membered lactam.
2-Pyrrolidone is a colorless liquid which is used in industrial settings as a high-boiling non-corrosive polar solvent for a wide variety of applications.
2-Pyrrolidone is a lactam cyclization product of gamma-aminobutyric acid.

2-Pyrrolidone is an organic compound consisting of a ve-membered lactam.
2-Pyrrolidone is a colorless liquid which is used in industrial settings as a high-boiling non-corrosive polar solvent for a wide variety of applications.
2-Pyrrolidone is miscible with a wide variety of other solvents including water, ethanol, diethyl ether, chloroform, benzene, ethyl acetate and carbon disulde.

2-Pyrrolidone Belongs to the class of organic compounds known as pyrrolidine-2-ones.
These are pyrrolidines which bear a C=O group at position 2 of the pyrrolidine ring
2-Pyrrolidone is a clear, almost colorless liquid above 25°C.

2-Pyrrolidone is an organic synthesis intermediate in the pharmaceutical industry, precursor of N-vinylpyrrolidone.
The product is used as a plasticizer and a setting agent for acrylic emulsions and acrylic/styrene copolymers used in oor polishes.
2-Pyrrolidone, also known as 2-pyrrolidinone or butyrolactam, is an organic compound consisting of a 5-membered lactam, making it the simplest γ-lactam.

2-Pyrrolidone is a colorless liquid that is miscible with water and most common organic solvents.
2-Pyrrolidone itself and various derivatives made from it have a variety of industrial uses.

Melting point: 23-25 °C (lit.),
Boiling point: 245 °C (lit.),
Density: 1.12 g/mL at 25 °C (lit.),
vapor density: 2.9 (vs air),
vapor pressure: 0.04 hPa (20 °C),
FEMA: 4829 | 2-PYRROLIDONE,
refractive index: n20/D 1.487 (lit.),
Flash point: >230 °F,
storage temp.: 2-8°C,
solubility: H2O: miscible (completely),
form: Liquid,
pka: 16.62±0.20 (Predicted),
color: Clear colorless to pale yellow,
PH: 9-11 (100g/l, H2O, 20℃),
explosive limit: 1.8-16.6% (V),
biological source: synthetic,
Water Solubility: miscible,
Sensitive: Hygroscopic,
Merck: 14,8016,
BRN: 105241,
Stability: Hygroscopic,
InChIKey: HNJBEVLQSNELDL-UHFFFAOYSA-N,
LogP: -0.71 at 20℃.

2-pyrrolidone is produced industrially almost exclusively by treating aqueous gamma-butyrolactone with ammonia at a temperature of 250–290 °C and pressures ranging from 0.4–1.4 MPa over solid magnesium silicate catalysts.
The reaction is carried out in a tubular reactor which is packed with the solid catalyst. 
The latter is arranged as a xed bed and the reaction is carried out in the vapor phase.

Product yields of 75–85% are reached.
After subsequent distillation and purication, the desired 2-pyrrolidone is obtained with a purity of 99.5%.
Alternative routes include the catalytic or electrochemical reduction of succinimide, the carbonylation of allylamine, the hydrogenation of succinonitrile under hydrolytic conditions and the reaction of maleic or succinic anhydride in aqueous ammonia with Pd–Rucatalysts.

2-Pyrrolidone and N-methylpyrrolidone are mainly used as solvents in veterinary injections.
2-Pyrrolidone has been shown to be a better solubilizer than glycerin, propylene glycol, or ethanol.
They have also been suggested for use in human pharmaceutical formulations as solvents in parenteral, oral, and topical applications.

In topical applications, pyrrolidones appear to be eective penetration enhancers.
2-Pyrrolidones have also been investigated for their application in controlled-release depot formulations.
2-Pyrrolidone is an organic compound consisting of a ve-membered lactam.

2-Pyrrolidone is a nonessential nutrient which can be normally generated during the glutathione cycle process inside the human body.
2-Pyrrolidone is also contained in fruits and vegetables.
2-Pyrrolidone is a widely-used solvent with outstanding characteristics.

2-Pyrrolidone is miscible with almost all other organic solvents
2-Pyrrolidone has a high boiling point.
2-Pyrrolidone is used as constituent of pharmaceutical preparations.

2-Pyrrolidone is used in Ink, toner, and colorant products
2-Pyrrolidone is used as a starting material in the synthesis of polyvinylpyrrolidone
2-Pyrrolidone itself is used in inkjet cartridges.

Due to its high polarity and low toxicity, 2-pyrrolidone is commonly used in formulations for cleaning agents, paints, coatings, and lubricants. 
In the pharmaceutical industry, it is utilized as a solvent or stabilizer in drug formulations, particularly for active pharmaceutical ingredients that are difficult to dissolve in water. 
2-pyrrolidone also acts as a stabilizing agent for certain proteins in biotechnology applications. 

Additionally, 2-pyrrolidone is employed in chemical research for the synthesis of various compounds, including those used in agrochemicals and polymers.
Despite its many uses, 2-pyrrolidone must be handled with care due to its hygroscopic nature, meaning it readily absorbs moisture from the air, which can affect its chemical properties. 

It is also considered to be slightly toxic and can cause skin and eye irritation upon contact. 
Therefore, proper safety protocols, such as wearing protective equipment, should be followed when handling this compound.

Uses:
2-Pyrrolidone itself is used in inkjet cartridges.
A variety of pharmaceutical drugs are 2-pyrrolidone derivatives, including cotinine, doxapram, povidone, and ethosuximide, and the racetams.
The chemical is an intermediate in the production of the polyvinylpyrrolidone precursor vinylpyrrolidone.

2-Pyrrolidone is a highly versatile compound with a wide range of applications across multiple industries, owing to its unique chemical properties. 
In the pharmaceutical industry, it is used as a solvent and stabilizer in various drug formulations, particularly for active pharmaceutical ingredients (APIs) that are difficult to dissolve in water. 
2-pyrrolidone is especially valuable in the preparation of intravenous medications and in the formulation of topical creams, ointments, and gels. 

2-pyrrolidone serves as a key intermediate in the synthesis of N-vinylpyrrolidone, a compound used in the production of water-soluble polymers, which are used in a variety of applications, such as in the manufacture of contact lenses, hair care products, and oral care products.
In the cosmetic and personal care industries, 2-pyrrolidone plays an important role as a solvent, humectant, and stabilizer in the production of lotions, shampoos, and conditioners. 
2-pyrrolidone is often included in formulations for its ability to enhance the solubility of active ingredients, ensuring that they are evenly distributed in the product.

2-pyrrolidone helps to keep the skin hydrated, making it a desirable ingredient in skin care products.
The compound is also used extensively in the agricultural and chemical industries. 
2-pyrrolidone acts as a solvent for various herbicides, pesticides, and fungicides, improving their effectiveness by enhancing their solubility and stability. 

Moreover, 2-pyrrolidone is used in the formulation of cleaning agents and detergents due to its ability to dissolve oils, fats, and dirt. 
2-pyrrolidone is an effective dispersing agent for inks, dyes, and pigments, which is why it is often used in the production of paints, coatings, and printing inks.
In addition to its industrial uses, 2-pyrrolidone is utilized in biotechnology applications. 

2-pyrrolidone is employed as a stabilizer for certain proteins during research and production processes, helping to maintain their structure and activity. 
The compound also finds use as a co-solvent in formulations for biomedical devices and diagnostic reagents. 
2-pyrrolidone is important in the production of polyvinylpyrrolidone (PVP), which is used in a wide variety of consumer goods, including films, adhesives, and as a binder in pharmaceuticals.

2-Pyrrolidone also plays a significant role in the polymer and plastics industries. 
It is used as a solvent and monomer in the production of polyvinylpyrrolidone (PVP) and polyvinyl alcohol (PVA), which are essential materials in the manufacturing of adhesives, coatings, and films. 
2-pyrrolidone, produced from 2-pyrrolidone, is used as a binder in tablet formulations, as well as in applications such as water-based coatings, inks, and the preparation of pharmaceutical tablets. 

2-pyrrolidones ability to form films makes it an ideal choice in industries where surface coating or film formation is important.
In the textile industry, 2-pyrrolidone is employed in the preparation of water-based dyes and finishes. 
It helps improve the dispersion of dyes and pigments, ensuring uniform color and stability in the final textile products. 

2-pyrrolidone is used in the leather industry to aid in the tanning process, enhancing the quality and durability of leather products. 
Its ability to act as a solvent and stabilizer allows it to be integrated into the processing of various natural and synthetic fibers, improving their strength, texture, and resistance to environmental conditions.
In the field of electronics and energy storage, 2-pyrrolidone is utilized in the formulation of electrolyte solutions for lithium-ion batteries. 

The solvent properties of 2-pyrrolidone enable the dissolution and stabilization of lithium salts and other components, contributing to the efficiency and longevity of batteries. 
2-pyrrolidone is also used in the production of flexible electronic components, such as conductive films and displays, where its role as a solvent helps to dissolve and disperse active materials.
2-pyrrolidone is explored in the field of environmental technology, where it has been considered for use in the development of biodegradable materials. 

Researchers are investigating its potential as a building block for producing biodegradable plastics, which could be used in packaging and other single-use products to reduce plastic waste.
2-pyrrolidone's solubility in water and its ability to break down in natural environments make it a promising candidate in the search for more sustainable alternatives to traditional plastics.

2-pyrrolidone’s use in the manufacturing of agricultural products is crucial. 
It acts as a solvent and stabilizer in formulations of fertilizers, herbicides, and insecticides, improving the effectiveness and uniformity of these products. 
Its ability to increase the solubility and dispersion of active ingredients makes it particularly valuable in the production of liquid fertilizers and pesticides, contributing to more efficient and environmentally friendly agricultural practices.

Safety Profile:
2-Pyrrolidone is relatively innocuous with an LD50 in the range of grams per kilogram (rats, oral). 
2-pyrrolidone is not mutagenic.
2-pyrrolidone can be an eye irritant.

2-pyrrolidone has certain hazards associated with its use, especially when it is not handled properly. 
The compound is classified as Hygroscopic, meaning it readily absorbs moisture from the air, which can alter its physical properties and increase its reactivity. 
2-pyrrolidone is also known to cause irritation to the skin, eyes, and respiratory tract, particularly when exposure occurs in high concentrations or for extended periods. 

Direct contact with the skin can lead to redness, dryness, or burning sensations, and inhaling vapors may cause respiratory discomfort, coughing, or shortness of breath.
When handling 2-pyrrolidone, eye protection, gloves, and proper ventilation are recommended to minimize exposure. 
Prolonged or repeated contact with the skin can lead to dermatitis, an inflammation of the skin. 

In cases of accidental eye exposure, immediate flushing with water is advised, and medical attention should be sought if irritation persists. 
Additionally, exposure to high concentrations of the vapors can cause headaches, dizziness, and nausea due to its ability to act as a volatile organic compound.

2-pyrrolidone is also considered a low toxicity substance when ingested in small quantities, but swallowing larger amounts can lead to gastrointestinal irritation, including symptoms like nausea, vomiting, and abdominal discomfort. 
Ingestion of large quantities could potentially lead to more severe effects such as central nervous system depression.

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