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Hexamethylenediamine

Chemical compound H2N(CH2)6NH2

Chemical compound H2N(CH2)6NH2

|NFPA-H = 3 |NFPA-F = 2 |NFPA-R = 0 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.

Hexamethylenediamine is involved in the synthesis of Chlorhexidine.

Safety

Hexamethylenediamine is moderately toxic, with 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.

References

References

  1. ''Merck Index'', 11th Edition, '''4614'''.
  2. [http://www.osha.gov/dts/chemicalsampling/data/CH_245190.html MSDS]
  3. (26 March 2005). "1,6-diaminohexane - Compound Summary". National Center for Biotechnology Information.
  4. Curtius, Theodor and Clemm, Hans (1900) [https://babel.hathitrust.org/cgi/pt?id=pst.000067440276;view=1up;seq=785 "Synthese des 1,3-Diaminopropans und 1,6-Diaminohexans aus Glutarsäure resp. Korksäure"] (Synthesis of 1,3-diaminopropane and 1,6-diaminohexane from glutaric acid and suberic acid, respectively), ''Journal für praktische Chemie'', 2nd series, '''62''' : 189–211.
  5. "SRIC Report - Report 31C - Advances in Adiponitrile (ADN) and Hexamethylenediamine (HMDA) Processes {{!}} IHS Markit".
  6. Robert A. Smiley "Hexamethylenediamine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. {{doi. 10.1002/14356007.a12_629
  7. (2020-12-01). "Hexamethylene diamine-modified epoxidized natural rubber and its effect on cure characteristics and properties of natural rubber blends". Iranian Polymer Journal.
  8. (July 2017). "Surface amine-functionalization of UHMWPE fiber by bio-inspired polydopamine and grafted hexamethylene diamine: Surface amine-functionalization of UHMWPE fiber by PDA and HMDA". Surface and Interface Analysis.
  9. (1991-09-01). "Aqueous dispersion of polyurethane ionomers from hexamethylene diisocyanate and trimellitic anhydride". Colloid and Polymer Science.
  10. (2017-05-01). "Synthesis and structure investigation of hexamethylene diisocyanate (HDI)-based polyisocyanates". Research on Chemical Intermediates.
  11. (2007-03-08). "Curing of epoxy resins. II. Curing of bisphenol a diglycidyl ether with diamines". Journal of Polymer Science: Polymer Symposia.
  12. (1978-04-01). "Are cured epoxy resins inhomogeneous?". Polymer.
  13. (2021-08-01). "Cross-linking of antimicrobial polymers with hexamethylene diamine to prevent biofouling in marine applications". Progress in Organic Coatings.
  14. (1956). "850. Bisdiguanides having antibacterial activity". Journal of the Chemical Society (Resumed).
  15. "MSDS - H11696".
  16. Kennedy, Gerald L.. (2005). "Toxicity of hexamethylenediamine". Drug and Chemical Toxicology.
  17. [https://news.bbc.co.uk/2/hi/uk_news/england/tees/6232239.stm BBC News]
  18. [https://news.bbc.co.uk/2/hi/uk_news/england/tees/6234287.stm BBC News]
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