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2-PYRROLIDONE

CAS NUMBER: 616-45-5

EC NUMBER: 210-483-1

MOLECULAR FORMULA: C4H7NO

MOLECULAR WEIGHT: 85.10

IUPAC NAME: pyrrolidin-2-one


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.

PRODUCTION OF 2-PYRROLIDONE
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. 
Product yields of 75–85% are reached. 
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

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 and the solvent N-methylpyrrolidone

2-Pyrrolidone is 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 gamma-aminobutyric acid (GABA). 
2-Pyrrolidone has a role as a polar solvent and a metabolite.

Use and Manufacturing:
2-Pyrrolidone is an Intermediate in mfr of polyvinylpyrrolidone & polypyrrolidone (polymer, formed in presence of alkaline catalysts); used as: 
-high-boiling solvent in petroleum processing, acrylonitrile mfr; 
-in specialty printers inks; 
-industrial solvent for:
*polymers
*Chlordane
*DDT
*sorbitol
*glycerol
*iodine
*sugars; 
-as plasticizer & coalescing agent for acrylic-styrene emulsion-type floor polishes

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 disulfide, etc.)
-Mixes with water in all proportions.
-High boiling point.
-Chemically and thermally stable, non-corrosive.

APPLICATIONS OF 2-PYRROLIDONE:
Pharmaceutical and Cosmetic Raw Materials:
*γ-Aminobutyric acid raw material
*Polyvinyl pyrrolidone raw material

Extraction Agent:
*Extraction of aromatic compounds

Plasticizers for Polymer-Based Floor Polish:
*Acrylic
*Acrylic-Styrene

De-colorant:
*Kerosene
*Rosin
*Fatty acids

Solvent:
*Synthetic resins
*Agricultural chemicals (chlordane etc.)
*Polyhydric alcohols (glycerin, sorbitol)
*Other (printing inks etc.)

Starting Material for Organic Synthesis:
*n-Methylol compounds
*γ-Amino acid derivatives

Polymer Raw Material:
*4-Nylon

2-Pyrrolidone an organic compound consisting of a five-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 disulfide.
2-Pyrrolidone is an intermediate in the manufacture of polymers such as polyvinylpyrrolidone and polypyrrolidone.
2-Pyrrolidone is a lactam cyclization product of gamma-aminobutyric acid.

Substituents:    
-2-pyrrolidone
-Pyrroline
-Secondary carboxylic acid amide
-Lactam
-Ketene acetal or derivatives
-Carboxamide group
-Azacycle
-Secondary amine
-Secondary aliphatic amine
-Carboxylic acid derivative
-Alkanolamine
-Organic nitrogen compound
-Organic oxygen compound
-Organopnictogen compound
-Organic oxide
-Hydrocarbon derivative
-Organooxygen compound
-Organonitrogen compound
-Carbonyl group
-Amine
-Aliphatic heteromonocyclic compound

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 effects. 
2-Pyrrolidone's L-form can increase the activity off 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 beneficial 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.

Chemical Properties:
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

Production Methods:
The synthesis of 2-Pyrrolidone was first reported in 1889 as the product of dehydration of 4-aminobutanoic acid. 
2-Pyrrolidone is produced commercially by condensation of butyrolactone with ammonia, a method first described in 1936. Other synthetic routes include carbon monoxide insertion into allylamine, hydrolytic hydrogenation of succinonitrile, and hydrogenation of ammoniacal solutions of maleic and succinnic acids

Pharmaceutical Applications:
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 effective penetration enhancers. 
2-Pyrrolidones have also been investigated for their application in controlled-release depot formulations.

Industrial Uses:
2-Pyrrolidone is used as an intermediate for synthesis of l-vinyl-2-pyrrolidone and various TV-methylol derivatives used as textile-finishing agents as
-a solvent for various polymers
-chlordane and DDT
-d-sorbitol
-glycerin
-sugars
-a decolorizing agent for kerosene, fatty oils, and rosins. 

N-methyl-2-pyrrolidone and 2-pyrrolidone are utilized in petroleum refining to selectively extract aromatics from paraffinic hydrocarbons. 
2-Pyrrolidone is used as a plasticizer and coalescing agent for acrylic latices and acrylic/styrene copolymers in emulsion coatings, i.e. floor waxes. 
A linear high molecular weight polyamide polymer of 2-pyrrolidone, nylon-4, is used as a textile fiber, injection molding compound, and film-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 floor 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 finds application as a solvent in the manufacture of membrane filters for e.g. sterile filtration of drugs such as pharmaceutical proteins, wine filtration systems
2-Pyrrolidone (2-Pyrrolidinone,2-Pyrol) is an organic compound consisting of a five-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 five-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 disulfide.

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 floor 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.

PHYSICAL PROPERTIES OF 2-PYRROLIDONE:

-Molecular Weight: 85.10    

-XLogP3: -0.8    

-Exact Mass: 85.052763847    

-Monoisotopic Mass: 85.052763847    

-Topological Polar Surface Area: 29.1 Ų    

-Physical Description: Liquid

-Color: Light yellow

-Form: Crystals from cold petroleum ether

-Boiling Point: 245.0 °C

-Melting Point: 23.0 °C

-Flash Point: 129 °C

-Solubility: 11.75 M

-Density: 1.116

-Vapor Density: 2.9

-Vapor Pressure: 0.01 mmHg

-LogP: -0.85

2-Pyrrolidone is an organic compound consisting of a five-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.

CHEMICAL PROPERTIES OF 2-PYRROLIDONE:

-Hydrogen Bond Donor Count: 1    

-Hydrogen Bond Acceptor Count: 1    

-Rotatable Bond Count: 0    

-Heavy Atom Count: 6    

-Formal Charge: 0    

-Complexity: 69.9    

-Isotope Atom Count: 0    

-Defined Atom Stereocenter Count: 0    

-Undefined Atom Stereocenter Count: 0    

-Defined Bond Stereocenter Count: 0    

-Undefined Bond Stereocenter Count: 0    

-Covalently-Bonded Unit Count: 1    

-Compound Is Canonicalized: Yes

-Corrosivity: Non-corrosive

-Heat of Combustion: -546.9

-Heat of Vaporization: 666 kJ/kg

-Refractive Index: 1.4806

-Dissociation Constants: pKa= 14.7

STORAGE OF 2-PYRROLIDONE:

2-Pyrrolidone can soluble in water
2-Pyrrolidone is hygroscopic.
2-Pyrrolidone should be kept under a dry nitrogen atmosphere.

2-Pyrrolidone should be stored in dry containers.
2-Pyrrolidone should be stored in a cool and clean environment.
2-Pyrrolidone is chemically stable

2-Pyrrolidone's Shelf life is approximately one year if kept in unopened original containers.
2-Pyrrolidone should be stored at temperatures below 20°C. 
2-Pyrrolidone should be protected from light.
2-Pyrrolidone should be stored in a well-closed container protected from oxidation.

SYNONYMS:

2-Pyrrolidinone
Butyrolactam
2-Oxopyrrolidine
2-Ketopyrrolidine
azacyclopentan-2-one
2-Tetrahydropyrrolone
alpha-Pyrrolidinone
2-Pyrrolidinone, homopolymer
Butanoic acid, lactam
butyrolactim
pyrollidone
2pyrrolidinone
a-pyrrolidone
2-pyrollidinone
2-pyrolidinone
2-pyrrolidinon
Aminobutyrolactam
Soluphor P
pyrrolidin-2-on
pyrrolid-2-one
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
2-pyrrolidone for synthesis
2-Pyrrolidinone, >=99%
.gamma.-Aminobutyric acid lactam
2-Pyrol4-aminobutyric acid lactam
Pyrrolidin-2-one (2-Pyrrolidone)
2-Pyrrolidinone
purum
Pyrrolidin-2-one 
(1-aza-2-cyclopentanone)

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