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Octamethylenediamine

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Octamethylendiamine
Structural formula of octamethylenediamine
Structural formula of octamethylenediamine
Names
IUPAC name Octane-1,8-diamine
Other names
  • 1,8-diaminooctane
  • 1,8-octanediamine
  • α,ω-Octanediamine
  • 4-(aminomethyl)octane-1,8-diamine
Identifiers
CAS Number
3D model (JSmol)
Abbreviations OMDA
Beilstein Reference 3-04-00-00612
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.150 Edit this at Wikidata
EC Number
  • 206-764-3
PubChem CID
RTECS number
  • RG8843000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H20N2/c9-7-5-3-1-2-4-6-8-10/h1-10H2Key: PWGJDPKCLMLPJW-UHFFFAOYSA-N
SMILES
  • NCCCCCCCCN
Properties
Chemical formula C8H20N2
Molar mass 144.26 g mol
Appearance colorless solid with an amine-like odor
Density 0.83 g cm (60 °C)
Melting point 52 °C
Boiling point 225-226 °C
Solubility in water Easily soluble in water (575 g l at 20°C)
Vapor pressure
  • 0.54 Pa (20 °C)
  • 1.0 Pa (25°C)
  • 32 Pa (50 °C)
Hazards
GHS labelling:
Pictograms GHS05: CorrosiveGHS07: Exclamation mark
Signal word Danger
Hazard statements H302, H314, H317
Precautionary statements P260, P280, P301+P312+P330, P303+P361+P353, P305+P351+P338+P310
Flash point 113 °C
Safety data sheet (SDS) "1,8-Diaminooctane". GESTIS-Stoffdatenbank. Retrieved 2022-08-05.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Octamethylenediamine (OMDA) is an organic chemical compound from the substance group of aliphatic diamines. It is used as a versatile reaction intermediate in the manufacture of pesticides, especially fungicides.

Manufacture

The industrial production of octamethylene diamine is carried out by the catalytic hydrogenation of suberonitrile at temperatures of 150 to 180 °C and a pressure of 50 to 180 bar in the presence of ammonia over heterogeneous cobalt unsupported catalysts:

Industrial_synthesis_of_octamethylenediamine
Industrial synthesis of octamethylenediamine

The reaction is carried out in the liquid phase and is carried out continuously or batchwise. The catalyst is arranged as a fixed bed in a shaft, tube, or tube bundle reactor.

Characteristics

Octamethylenediamine is a combustible but difficult to ignite. It is a solid that is easily soluble in water. The aqueous solutions are strongly alkaline (pH value of 12.1 at a concentration of 10 g/L).

Use

Octamethylenediamine is used as a versatile intermediate in manufacturing pesticides, especially fungicides.

Safety instructions

While octamethylenediamine is combustible, it is difficult to ignite because it is solid at moderate temperatures. It has a lower explosive limit (LEL) of 1.1 % by volume and an upper explosive limit (UEL) of 6.8 % by volume. The ignition temperature is 280 °C The substance therefore falls into temperature class T3. With a flash point of 113 °C, the liquid is considered difficult to ignite.

References

  1. ^ Record of Octamethylenediamine in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 2022-01-20.
  2. "373-44-4 - 1,8-Diaminooctane, 98% - 1,8-Octanediamine - B23885". Alfa Aesar. 2017-10-22. Retrieved 2022-08-06.
  3. "1,8-Octanediamine". CAS Common Chemistry. Retrieved 2022-08-05.
  4. ^ "WO2018050555A1 Method for the Preparation of Polyamines from Dinitriles and/or Amino Nitrile". Espacenet – patent search. 2021-03-20. Retrieved 2022-08-05.
  5. Peter Roose, Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke: Amines, Aliphatic. In: Ullmann’s Encyclopedia of Industrial Chemistry. Wiley‐VCH Verlag GmbH & Co. KGaA., 30. September 2015, doi:10.1002/14356007.a02_001.pub2.

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