2-Piperidinone (2-piperidone or δ-valerolactam) is an organic compound with the formula (CH2)4CONH. Valerolactam is formed by dehydrogenation of 5-amino-1-pentanol, catalyzed by rhodium and ruthenium complexes, [3][4] The compound, a colorless solid, is classified as a lactam.
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| Names | |
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| Preferred IUPAC name
Piperidin-2-one | |
Other names
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.010.567 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C5H9NO | |
| Molar mass | 99.133 g·mol−1 |
| Density | 1.073 g/cm3[1] |
| Melting point | 38 to 40 °C (100 to 104 °F; 311 to 313 K)[2] |
| Boiling point | 256 °C (493 °F; 529 K)[2] |
| 291 g/L[1] | |
| Hazards | |
| Flash point | > 110 °C (230 °F; 383 K)[1] |
| Safety data sheet (SDS) | MSDS |
| Related compounds | |
Related compounds
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4-Piperidinone |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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It is the monomer of nylon 5, a polyamide:
- n (CH2)4CONH → [HN(CH2)4CO)]n
References
edit- ^ a b c 2-Piperidone at Chemical Book
- ^ a b δ-Valerolactam at Sigma-Aldrich
- ^ M. Trincado; K. Kühlein; H. Grützmacher (2011), "Metal-Ligand Cooperation in the Catalytic Dehydrogenative Coupling (DHC) of Polyalcohols to Carboxylic Acid Derivatives", Chem. Eur. J., 17 (42): 11905–11913, doi:10.1002/chem.201101084, PMID 21901769
- ^ D. Pingen; D. Vogt (2014), "Amino-Alcohol Cyclization: Selective Synthesis of Lactams and Cyclic Amines from Amino-Alcohols", Catal. Sci. Technol., 4: 47–52, doi:10.1039/C3CY00513E, hdl:20.500.11820/6875ce86-a727-49b8-949f-f71a172043a3, S2CID 52265163
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