Structure via PubChem · Public domain (PubChem)
hexamethylenediamine
Sign in to saveAlso known as 1,6-hexanediamine, 1,6-diaminohexane, HMDA, hexamethylene diamine, 1,6-hexylenediamine, 1,6-diamino-n-hexane, H2N(CH2)6NH2, hexylenediamine
Hexamethylenediamine or hexane-1,6-diamine, is the organic compound with the formula H2N(CH2)6NH2. The molecule is a diamine, consisting of a hexamethylene hydrocarbon chain terminated with amine functional groups. The colorless solid (yellowish for some commercial samples) has a strong amine odor.
Chemical data
- Formula
- C6H16N2
- Molecular weight
- 116.2 g/mol
- IUPAC name
- hexane-1,6-diamine
- SMILES
- C(CCCN)CCN
- InChIKey
- NAQMVNRVTILPCV-UHFFFAOYSA-N
- XLogP
- -0.2
- Polar surface area
- 52 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
~2 min read
Encyclopedic overview
5 sectionsContents
- Synthesis
- Applications
- Safety
- See also
- References
Hexamethylenediamine or hexane-1,6-diamine, is the organic compound with the formula H2N(CH2)6NH2. The molecule is a diamine, consisting of a hexamethylene hydrocarbon chain terminated with amine functional groups. The colorless solid (yellowish for some commercial samples) has a strong amine odor.
==Synthesis== Hexamethylenediamine was first reported by Theodor Curtius. It is produced by the hydrogenation of adiponitrile: NC(CH2)4CN + 4 H2 → H2N(CH2)6NH2 The hydrogenation is conducted on molten adiponitrile diluted with ammonia, typical catalysts being based on cobalt and iron. The yield is good, but commercially significant side products are generated by virtue of reactivity of partially hydrogenated intermediates. These other products include 1,2-diaminocyclohexane, hexamethyleneimine, and the triamine bis(hexamethylenetriamine).
Excerpted from Wikipedia’s “hexamethylenediamine” article, available under the CC BY-SA 4.0 licence.