Trimethylhexamethylenediamine

2,4,4-Trimethylhexamethylenediamine[1]
Names
	IUPAC name 2,4,4-Trimethyl-1,6-hexanediamine
Identifiers
3D model (JSmol)	Interactive image;
ChemSpider	83906 ;
	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
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

2,2,4-Trimethylhexamethylenediamine[1]
Names
	IUPAC name 2,2,4-Trimethyl-hexane-1,6-diamine
Identifiers
3D model (JSmol)	Interactive image;
ChemSpider	69172;
	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

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

"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.CS1 maint: uses authors parameter (link)
U. Rohde-Liebenau (1995). "13.10 PA-TMDT". In Kohan, Melvin (ed.). Nylon Plastics Handbook. Munich: Hanser. p. 570. ISBN 1569901899.
"Vestamin TMD" (PDF).

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[chemicalbook.com-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.CS1 maint: uses authors parameter (link)

[3] U. Rohde-Liebenau (1995). "13.10 PA-TMDT". In Kohan, Melvin (ed.). Nylon Plastics Handbook. Munich: Hanser. p. 570. ISBN 1569901899.

[4] "Vestamin TMD" (PDF).