Girish Mahajan (Editor)

Diamine

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A diamine is an amine with exactly two amino groups. Diamines are used as monomers to prepare polyamides, polyimides and polyureas. In terms of quantities produced, 1,6-diaminohexane, a precursor to Nylon 6-6, is most important, followed by ethylenediamine. Vicinal diamines (1,2-diamines) are a structural motif in many biological compounds and are used as ligands in organometallic chemistry

Contents

Linear aliphatic diamines

  • 2 carbons: ethylenediamine (1,2-diaminoethane). Related derivatives include the N-alkylated compounds, 1,1-dimethylethylenediamine, 1,1-dimethylethylenediamine, ethambutol and TMEDA.
  • 3 carbons: 1,3-diaminopropane (propane-1,3-diamine)
  • 4 carbons: putrescine (butane-1,4-diamine)
  • 5 carbons: cadaverine (pentane-1,5-diamine)
  • 6 carbons: hexamethylenediamine (hexane-1,6-diamine)

    • Branched aliphatic diamines

    Derivatives of ethylenediamine are prominent:

  • 1,2-diaminopropane, which is chiral.
  • diphenylethylenediamine, which is C2-symmetric.
  • diaminocyclohexane, which is C2-symmetric.

    • Xylylenediamines

    Xylylenediamines are classified as alkylamines since the amine is not directly attached to an aromatic ring.

  • o-xylylenediamine or OXD
  • m-xylylenediamine or MXD
  • p-xylylenediamine or PXD

    • Aromatic diamines

    Three phenylenediamines are known:

  • o-phenylenediamine or OPD
  • m-phenylenediamine or MPD
  • p-phenylenediamine or PPD. 2,5-Diaminotoluene is related to PPD but contains a methyl group on the ring.

    • Various N-methylated derivatives of the phenylenediamines are known:

  • dimethyl-4-phenylenediamine, a reagent.
  • N,N'-di-2-butyl-1,4-phenylenediamine, an antioxidant.

    • Examples with two aromatic rings include derivatives of biphenyl and naphthalene:

  • 4,4'-diaminobiphenyl
  • 1,8-diaminonaphthalene

    • References

    Diamine Wikipedia
    (Text) CC BY-SA