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Hexamethylenediamine

Hexamethylenediamine
Skeletal formula of hexamethylenediamine
Ball and stick model of hexamethylenediamine
Spacefill model of hexamethylenediamine
Names
IUPAC name
Hexane-1,6-diamine
Other names
  • 1,6-Diaminohexane
  • 1,6-Hexanediamine
Identifiers
3D model (Jmol)
1098307
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.004.255
EC Number 204-679-6
2578
MeSH 1,6-diaminohexane
PubChem CID
RTECS number MO1180000
UN number 2280
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
−205 kJ mol−1
Hazards
GHS pictograms The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H302, H312, H314, H335
P261, P280, P305+351+338, P310
Corrosive C
R-phrases R21/22, R34, R37
S-phrases (S1/2), S22, S26, S36/37/39, S45
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 80 °C (176 °F; 353 K)
Explosive limits 0.7–6.3%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
  • 750 mg kg−1(oral, rat)
  • 1.11 g kg−1(dermal, rabbit)
Related compounds
Related alkanamines
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
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.

Hexamethylenediamine was first reported by Theodor Curtius. It is produced by the hydrogenation of adiponitrile:

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.

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.


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