Trimethylhexamethylenediamine

{{chembox

| Name = 2,2,4-Trimethylhexamethylenediamine

| Reference ={{cite web|url=http://www.chemicalbook.com/ChemicalProductProperty_EN_CB9493047.htm|title=TRIMETHYLHEXAMETHYLENEDIAMINE|work=chemicalbook.com|access-date=19 April 2015}}

| ImageFile = 2,2,4-Trimethylhexamethylenediamine.png

| PIN = 2,2,4-Trimethylhexane-1,6-diamine

|Section1={{Chembox Identifiers

| CASNo = 3236-54-2

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 595BQ3Q70K

| ChEMBL = 3182194

| ChemSpiderID = 69172

| DTXSID = DTXSID30274136

| EC_number = 221-793-1

| PubChem = 76714

| StdInChI = InChI=1S/C9H22N2/c1-8(4-5-10)6-9(2,3)7-11/h8H,4-7,10-11H2,1-3H3

| StdInChIKey = JCUZDQXWVYNXHD-UHFFFAOYSA-N

| SMILES = CC(CC(C)(C)CCN)CN

}}

|Section2={{Chembox Properties

| C=9 | H=22 | N=2

}}

}}

{{chembox

| Name = 2,4,4-Trimethylhexamethylenediamine

| Reference =

| ImageFile = 2,4,4-Trimethylhexamethylenediamine.png

| PIN = 2,4,4-Trimethylhexane-1,6-diamine

|Section1={{Chembox Identifiers

| CASNo = 3236-53-1

| CASNo_Ref = {{Cascite|changed|CAS}}

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 83906

| EINECS = 221-792-6

| PubChem = 92950

| StdInChI = 1S/C9H22N2/c1-8(7-11)6-9(2,3)4-5-10/h8H,4-7,10-11H2,1-3H3

| StdInChIKey = DPQHRXRAZHNGRU-UHFFFAOYSA-N

| SMILES = CC(CCN)CC(C)(C)CN

}}

|Section2={{Chembox Properties

| C=9 | H=22 | N=2

}}

|Section3={{Chembox Hazards

| GHSPictograms = {{GHS05}}{{GHS07}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|302|314|317|412}}

| PPhrases = {{P-phrases|260|261|264|270|272|273|280|301+312|301+330+331|302+352|303+361+353|304+340|305+351+338|310|321|330|333+313|363|405|501}}

}}

}}

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.{{cite encyclopedia|author=Hardo Siegel |author2=Manfred Eggersdorfer |title=Ketones|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2005|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a15_077|isbn=978-3-527-30673-2}} 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.{{cite book|author1=U. Rohde-Liebenau|editor1-last=Kohan|editor1-first=Melvin|title=Nylon Plastics Handbook|date=1995|publisher=Hanser|location=Munich|isbn=1-56990-189-9|page=570|chapter=13.10 PA-TMDT}}