54920-40-0

Upstream product

• 3968-96-5 (E)-3,5,5-trimethylcyclohex-2-en-1-one oxime 
• 3968-95-4 (Z)-isophorone oxime 
• 2157-58-6 3,5,5-trimethyl-cyclohex-2-enone oxime 
• 7027-11-4 isophoronenitrile 

Downstream Products

• 62034-44-0 methyl-(3,5,5-trimethyl-cyclohex-2-enyl)-amine 

Relevant academic research and scientific papers

METHOD FOR THE PRODUCTION OF ISOPHORONDIAMINE (IPDA, 3-AMINOMETHYL-3,5,5-TRIMETHYLCYCLOHEXYLAMINE) HAVING A HIGH CIS/TRANS-ISOMER RATIO

The invention relates to a method for the production of 3 aminomethyl-3,5,5- trimethylcyclohexylamine (isophorondiamine, IPDA) which has a high cis/trans isomer ratio. IPDA having a cis/trans isomer ratio in the range of 63/37 - 66/34 can be obtained in a temperature-independent manner by reacting IPDA having any particular cis/trans isomer ratio with H2 and NH3 in the presence of a hydrogenating catalyst. IPDA having a cis/trans isomer ratio of at least 73/27, which is an important starting material for the synthesis of polyurethanes and polyamides, can be obtained by combining said isomerization method with distillation methods.

REDUCTION OF CONJUGATED CYCLOHEXENONE OXIMES WITH ALUMINIUM HYDRIDE

The reduction of representative conjugated cyclohexenone oximes with aluminium hydride in tetrahydrofuran yields 2-cyclohexenylamines and saturated aziridines - 7-azabicycloheptane derivatives, as the main reaction products.Small quantities of cyclohexylamines and perhydroazepines are also formed.Regioselectivity of the reduction depends on oxime configuration.Higher yields of 2-cyclohexenylamines are obtained from E than Z isomers.The reaction mechanism is proposed.