Hexamethylenediamine

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Hexamethylenediamine

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Template:Longitem	1098307
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EC Number	Template:Unbulleted list
Template:Longitem	2578
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MeSH	1,6-diaminohexane
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RTECS number	Template:Unbulleted list
UN number	2280
Template:Longitem	Template:Chembox Elements/molecular formula
Molar mass	Template:Chem molar mass
Appearance	Colourless crystals
Density	0.84 g/mL
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log P	0.386
Template:Longitem	−205 kJ mol−1
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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).

An alternative process uses Raney nickel as the catalyst and adiponitrile that is diluted with hexamethylenediamine itself (as the solvent). This process operates without ammonia and at lower pressure and temperature.

Applications

Hexamethylenediamine is used almost exclusively for the production of polymers, an application that takes advantage of its structure. It is difunctional in terms of the amine groups and tetra functional with respect to the amine hydrogens. The great majority of the diamine is consumed by the production of nylon 66 via condensation with adipic acid. Otherwise hexamethylene diisocyanate (HDI) is generated from this diamine by phosgenation as a monomer feedstock in the production of polyurethane. The diamine also serves as a cross-linking agent in epoxy resins.

Safety

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 in which 37 persons were injured, one of them seriously.

See also

• 1,2-Diaminocyclohexane
• 2-Methylpentamethylenediamine