Hexamethylenediamine
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| Names | |
|---|---|
| IUPAC name
Hexane-1,6-diamine[3] | |
Other names
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| Identifiers | |
124-09-4  | |
| 3D model (Jmol) | Interactive image |
| 1098307 | |
| ChEBI | CHEBI:39618  |
| ChEMBL | ChEMBL303004 |
| ChemSpider | 13835579 |
| DrugBank | DB03260 |
| ECHA InfoCard | 100.004.255 |
| EC Number | 204-679-6 |
| 2578 | |
| MeSH | 1,6-diaminohexane |
| PubChem | 16402 |
| RTECS number | MO1180000 |
| UN number | 2280 |
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| Properties | |
| C6H16N2 | |
| Molar mass | 116.21 g·mol−1 |
| Appearance | Colourless crystals |
| Density | 0.84 g/mL |
| 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 |
| 490 g L−1 | |
| log P | 0.386 |
| Thermochemistry | |
| Std enthalpy of formation (ΔfH |
−205 kJ mol−1 |
| Hazards | |
| GHS pictograms |   |
| GHS signal word | DANGER |
| H302, H312, H314, H335 | |
| P261, P280, P305+351+338, P310 | |
| EU classification (DSD) |
 C |
| R-phrases | R21/22, R34, R37 |
| S-phrases | (S1/2), S22, S26, S36/37/39, S45 |
| NFPA 704 | |
| Flash point | 80 °C (176 °F; 353 K) |
| Explosive limits | 0.7–6.3% |
| Lethal dose or concentration (LD, LC): | |
| LD50 (median dose) |
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| Related compounds | |
| Related alkanamines |
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| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| Infobox references | |
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.[4]
Synthesis
Hexamethylenediamine was first reported by Theodor Curtius.[5] 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 operates in diluted ADN conditions using HMD itself as a solvent and Raney Nickel as catalyst. This process operates without ammonia and at lower pressure and temperature[4]
Applications
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 66 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.
Safety
Hexamethylenediamine is moderately toxic, with LD50 of 792-1127 mg/kg.[4] 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.[6][7]
Stability
Hexamethylenediamine is stable in air but combustible. Like all organic compounds, it is incompatible with strong oxidants.
References
- ↑ Merck Index, 11th Edition, 4614.
- ↑ MSDS
- ↑ "1,6-diaminohexane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 29 May 2012.
- 1 2 3 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