Dicyclohexylamine
![]() | |
Names | |
---|---|
Preferred IUPAC name
N-Cyclohexylcyclohexanamine | |
Identifiers | |
3D model (JSmol)
|
|
ChemSpider | |
EC Number |
|
PubChem CID
|
|
UNII | |
| |
| |
Properties | |
C12H23N | |
Molar mass | 181.323 g·mol−1 |
Appearance | Pale yellow liquid |
Density | 0.912 g/cm3 |
Melting point | −0.1 °C (31.8 °F; 273.0 K) |
Boiling point | 255.8 °C (492.4 °F; 529.0 K) |
0.8 g/L | |
Hazards | |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
|
373 mg/kg (oral)[clarification needed] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
Dicyclohexylamine is a secondary amine with the chemical formula HN(C6H11)2. It is a colorless liquid, although commercial samples can appear yellow. It has a fishy odor, typical for amines. It is sparingly soluble in water. As an amine, it is an organic base and useful precursor to other chemicals.[1]
Synthesis
Dicyclohexylamine, as a mixture with cyclohexylamine, is prepared by the catalytic hydrogenation of aniline (phenylamine), with a catalyst of ruthenium and/or palladium. This method produces mainly cyclohexylamine with little dicyclohexylamine. Better results have been reported when the catalyst is applied to a support of niobic acid and/or tantalic acid.[2] It is also obtained by reductive amination of cyclohexanone with ammonia or cyclohexylamine.[1]
Dicyclohexylamine may also be prepared by pressure hydrogenation of diphenylamine using a ruthenium catalyst, or by the reaction of cyclohexanone with cyclohexylamine in the presence of a palladium/carbon catalyst under a hydrogen pressure of about 4 mm Hg.[2]
Applications
Dicyclohexylamine has applications that are similar to those of cyclohexylamine, namely the production of:
- antioxidants in rubber and plastics
- vulcanization accelerators for rubber
- corrosion inhibitors in steam pipes and boilers
- agrochemicals
- textile chemicals
- catalysts for flexible polyurethane foams
References
- ^ a b Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic". In Ullmann's Encyclopedia of Industrial Chemistry, 2000, Wiley-VCH, Weinheim. doi:10.1002/14356007.a02_001
- ^ a b U.S. Patent 5322965, "Process for the preparation of a mixture of cyclohexylamine and dicyclohexylamine using a supported noble metal catalyst", Bayer AG, 21 June 1994
External links
- Articles without InChI source
- Articles without EBI source
- Articles without KEGG source
- Pages using collapsible list with both background and text-align in titlestyle
- Justapedia articles needing clarification from October 2014
- Articles with invalid date parameter in template
- Articles containing unverified chemical infoboxes
- Articles with short description
- Short description with empty Wikidata description
- Amines
- Cyclohexyl compounds