Trimethylhexamethylenediamine

2,4,4-Trimethylhexamethylenediamine^[1]
Names
	Preferred IUPAC name 2,4,4-Trimethylhexane-1,6-diamine
Identifiers
CAS Number	3236-53-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	83906 ;
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

2,2,4-Trimethylhexamethylenediamine^[1]
Names
	Preferred IUPAC name 2,2,4-Trimethylhexane-1,6-diamine
Identifiers
CAS Number	3236-54-2 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3182194;
ChemSpider	69172;
EC Number	221-793-1;
PubChem CID	76714;
UNII	595BQ3Q70K ;
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

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

^ ^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).

[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. 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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