Trimethylhexamethylenediamine

Trimethylhexamethylenediamine is the name used to refer to a mixture of two isomers of trimethyl-1,6-hexanediamine. The mixture is used as a monomer in nylon TMDT. It is available commercially under the trade name Vestamin TMD from the company Evonik Industries.

2,2,4-Trimethylhexamethylenediamine[1]
Names
Preferred IUPAC name
2,2,4-Trimethylhexane-1,6-diamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 221-793-1
UNII
  • InChI=1S/C9H22N2/c1-8(4-5-10)6-9(2,3)7-11/h8H,4-7,10-11H2,1-3H3
    Key: JCUZDQXWVYNXHD-UHFFFAOYSA-N
  • CC(CC(C)(C)CCN)CN
Properties
C9H22N2
Molar mass 158.289 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
2,4,4-Trimethylhexamethylenediamine[1]
Names
Preferred IUPAC name
2,4,4-Trimethylhexane-1,6-diamine
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 221-792-6
  • InChI=1S/C9H22N2/c1-8(7-11)6-9(2,3)4-5-10/h8H,4-7,10-11H2,1-3H3
    Key: DPQHRXRAZHNGRU-UHFFFAOYSA-N
  • CC(CCN)CC(C)(C)CN
Properties
C9H22N2
Molar mass 158.289 g·mol−1
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H314, H317, H412
P260, P261, P264, P270, P272, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P333+P313, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Trimethylhexamethylenediamine is synthesized from isophorone.[2] Isophorone is reduced by hydrogenation to the trimethylcyclohexanol, which is then oxidized with nitric acid (in the same fashion as adipic acid is synthesized from cyclohexane). The diacid is converted to the diamine via the dinitrile.[3]

Uses

TMD is used as a component in certain curing agents for epoxy resins.[4]

References
  1. "TRIMETHYLHEXAMETHYLENEDIAMINE". chemicalbook.com. Retrieved 19 April 2015.
  2. Hardo Siegel; Manfred Eggersdorfer (2005). "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077. ISBN 978-3-527-30673-2.
  3. U. Rohde-Liebenau (1995). "13.10 PA-TMDT". In Kohan, Melvin (ed.). Nylon Plastics Handbook. Munich: Hanser. p. 570. ISBN 1-56990-189-9.
  4. "Vestamin TMD" (PDF).
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