N-Vinyl-2-pyrrolidone
[CAS# 88-12-0]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: N-Vinyl-2-pyrrolidone
• Synonyms: 1-Vinyl-2-pyrrolidone; N-Vinylbutyrolactam
• Molecular Formula: C₆H₉NO
• Molecular Weight: 111.14
• CAS Registry Number: 88-12-0
• EC Number: 201-800-4
• SMILES: C=CN1CCCC1=O

Properties

• Density: 1.043
• Melting point: 13-14 °C
• Boiling point: 90-92 °C (9.7513 mmHg)
• Refractive index: 1.5119-1.5139
• Flash point: 95 °C
• Water solubility: miscible

Safety Data

• Hazard Symbols: GHS06;GHS05;GHS09 Danger
• Risk Statements: H351-H332-H312-H302-H335-H373-H318
• Safety Statements: P501-P261-P270-P202-P201-P271-P264-P280-P308+P313-P361+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P312-P305+P351+P338+P310-P403+P233-P405

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Carcinogenicity	Carc.	2	H351
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	3	H311
Specific target organ toxicity - single exposure	STOT SE	2	H371
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Specific target organ toxicity - single exposure	STOT SE	3	H370
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H331

• Transport Information: UN 2810

Discovery and Applications

N-Vinyl-2-pyrrolidone (NVP) is an important organic compound belonging to the class of vinyl pyrrolidones, primarily known for its role as a versatile monomer in polymer chemistry. It was first synthesized in the early 1950s through the polymerization of 2-pyrrolidone, a five-membered lactam. The discovery of NVP was driven by the need for new materials with unique properties, particularly in the fields of adhesives, coatings, and medical applications.

The polymerization of NVP yields poly(N-vinyl-2-pyrrolidone) (PVP), a water-soluble polymer that exhibits a range of desirable characteristics. PVP is notable for its film-forming ability, high biocompatibility, and excellent solubility in various solvents. These properties have made NVP a critical component in many industrial and consumer products.

One of the primary applications of NVP is in the pharmaceutical and cosmetic industries. PVP is often used as a binding agent in tablet formulations, improving the cohesiveness of powdered ingredients. It also acts as a stabilizer in suspensions and emulsions, enhancing the uniformity and effectiveness of topical formulations. In the cosmetic sector, NVP is employed in hair styling products, skin creams, and sunscreens, where it provides a smooth application and enhances product texture.

NVP's ability to form hydrogels has opened new avenues in biomedical applications. Hydrogels made from PVP are used in wound dressings, contact lenses, and drug delivery systems. Their biocompatibility and moisture retention properties make them ideal for maintaining a conducive environment for healing and promoting comfort in medical applications.

In addition to its applications in pharmaceuticals and cosmetics, NVP is also utilized in the production of specialty coatings and adhesives. Its film-forming properties enable the creation of durable coatings that adhere well to various surfaces. The incorporation of NVP into adhesives enhances their strength and flexibility, making them suitable for a wide range of bonding applications, including those in the automotive and electronics industries.

Moreover, NVP is an essential ingredient in the production of superabsorbent polymers, which are widely used in products such as diapers and feminine hygiene items. These polymers can absorb and retain significant amounts of liquid relative to their mass, making them invaluable in personal care products.

Despite its widespread use, safety considerations regarding NVP are essential. Studies have indicated that NVP and its polymer, PVP, are generally recognized as safe when used according to established guidelines. Regulatory bodies such as the U.S. Food and Drug Administration (FDA) and the European Commission have evaluated NVP and approved its use in various applications, ensuring consumer safety.

Research into NVP continues, with ongoing investigations exploring its potential in novel applications, including environmental remediation and advanced drug delivery systems. Its unique chemical structure allows for modifications that can enhance its functionality, paving the way for innovative materials that meet emerging needs in various fields.

In conclusion, N-Vinyl-2-pyrrolidone is a significant compound with diverse applications across industries, particularly in pharmaceuticals, cosmetics, and materials science. Its discovery has led to the development of versatile polymers that enhance product performance and safety. As research advances, the potential for NVP in new applications continues to expand, underscoring its importance in modern chemistry and technology.

References

2008. Solubility of Small-Molecule Crystals in Polymers: d-Mannitol in PVP, Indomethacin in PVP/VA, and Nifedipine in PVP/VA. Pharmaceutical Research, 26(2).
DOI: 10.1007/s11095-008-9784-z

2007. Polymeric nanoparticle-encapsulated curcumin ("nanocurcumin"): a novel strategy for human cancer therapy. Journal of Nanobiotechnology, 5(3).
DOI: 10.1186/1477-3155-5-3

2007. Biosensors based on screen-printing technology, and their applications in environmental and food analysis. Analytical and Bioanalytical Chemistry, 388(2).
DOI: 10.1007/s00216-007-1293-0