|Jmol-3D images||Image 1|
|Molar mass||116.20 g mol−1|
|Melting point||39 to 42 °C (102 to 108 °F; 312 to 315 K)|
|Boiling point||204.6 °C; 400.2 °F; 477.7 K|
|Solubility in water||490 g L−1|
|Std enthalpy of
|−205 kJ mol−1|
|GHS signal word||DANGER|
|GHS hazard statements||H302, H312, H314, H335|
|GHS precautionary statements||P261, P280, P305+351+338, P310|
|R-phrases||R21/22, R34, R37|
|S-phrases||(S1/2), S22, S26, S36/37/39, S45|
|Flash point||80 °C (176 °F; 353 K)|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
Hexamethylenediamine 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, similar to piperidine. About 1 billion kilograms are produced annually.
- NC(CH2)4CN + 4 H2 → H2N(CH2)6NH2
The hydrogenation is conducted 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).
An alternative process operates in diluted ADN conditions using HMD itself as a solvent and Ni Raney as catalyst. This process operates without ammonia and at lower pressure and temperature
Hexamethylenediamine is used almost exclusively for the production of polymers, an application that takes advantage of its bifunctional structure. The great majority of the diamine is consumed by the production of nylon 6-6 via condensation with adipic acid. Otherwise hexamethylene diisocyanate (HDI) is generated from this diamine as a monomer feedstock in the production of polyurethane. The diamine also serves as a cross-linking agent in epoxy resins.
Hexamethylenediamine is moderately toxic, with LD50 of 792-1127 mg/kg. Nonetheless, like other basic amines, it can cause serious burns and severe irritation. Such injuries were observed in the accident at the BASF site in Seal Sands, near Billingham (UK) on 4 January, 2007. 37 injured and 16 seriously injured.
Hexamethylenediamine is stable in air but combustible. Like all organic compounds, it is incompatible with strong oxidants.
- Merck Index, 11th Edition, 4614.
- "1,6-diaminohexane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 29 May 2012.
- Robert A. Smiley "Hexamethylenediamine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a12 629
- T. Curtius et al. J. Prakt. Chem., 1900, volume 62, p. 189.
- BBC News
- BBC News