Dicyclohexylamine

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]

Dicyclohexylamine
Structural Formula dicyclohexylamine
Names
Preferred IUPAC name
N-Cyclohexylcyclohexanamine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.710
EC Number
  • 202-980-7
UNII
  • InChI=1S/C12H23N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h11-13H,1-10H2
    Key: XBPCUCUWBYBCDP-UHFFFAOYSA-N
  • C1CCC(CC1)NC2CCCCC2
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):
373 mg/kg (oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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
  1. 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
  2. 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
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