Trimethylhexamethylenediamine

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).
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).

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.

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, again a mixture of two "trimethyladipic acids", 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. ^ a b "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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