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.

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
3D model (JSmol)
Abbreviations OMDA
3-04-00-00612
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.150 Edit this at Wikidata
EC Number
  • 206-764-3
RTECS number
  • RG8843000
UNII
  • InChI=1S/C8H20N2/c9-7-5-3-1-2-4-6-8-10/h1-10H2
    Key: PWGJDPKCLMLPJW-UHFFFAOYSA-N
  • NCCCCCCCCN
Properties
C8H20N2
Molar mass 144.26 g mol−1
Appearance colorless solid with an amine-like odor[1]
Density 0.83 g cm−3 (60 °C)[1]
Melting point 52 °C[3]
Boiling point 225-226 °C[1][2]
Easily soluble in water (575 g l−1 at 20°C)[1]
Vapor pressure
Hazards
GHS labelling:[1]
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H314, H317
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 [77 °F], 100 kPa).

Manufacture

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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

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

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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).[4]

Octamethylenediamine is used as a versatile intermediate in manufacturing pesticides, especially fungicides.[5]

Safety instructions

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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.[4]

References

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  1. ^ a b c d e f g h 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. ^ a b "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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