Trimethylhexamethylenediamine

2,2,4-Trimethylhexamethylenediamine^[1]
Names

Preferred IUPAC name 2,2,4-Trimethylhexane-1,6-diamine
Identifiers
CAS Number	3236-54-2^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL3182194
ChemSpider	69172
EC Number	221-793-1
PubChem CID	76714
UNII	595BQ3Q70K^Y
CompTox Dashboard (EPA)	DTXSID30274136
InChI 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
SMILES CC(CC(C)(C)CCN)CN
Properties
Chemical formula	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

Chemical compound

2,4,4-Trimethylhexamethylenediamine^[1]
Names

Preferred IUPAC name 2,4,4-Trimethylhexane-1,6-diamine
Identifiers
CAS Number	3236-53-1^N
3D model (JSmol)	Interactive image
ChemSpider	83906^Y
EC Number	221-792-6
PubChem CID	92950
InChI 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
SMILES CC(CCN)CC(C)(C)CN
Properties
Chemical formula	C₉H₂₂N₂
Molar mass	158.289 g·mol⁻¹
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H314, H317, H412
Precautionary statements	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

Chemical compound

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 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

^ ^a ^b "TRIMETHYLHEXAMETHYLENEDIAMINE". chemicalbook.com. Retrieved 19 April 2015.
^ 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.
^ U. Rohde-Liebenau (1995). "13.10 PA-TMDT". In Kohan, Melvin (ed.). Nylon Plastics Handbook. Munich: Hanser. p. 570. ISBN 1-56990-189-9.
^ "Vestamin TMD" (PDF).