METHOD OF PRODUCING 3-AMINOMETHYL-3,5,5-TRIMETHYLCYCLOHEXYLAMINE Russian patent published in 2017 - IPC C07C211/35 C07C209/48 

FIELD: chemistry.

SUBSTANCE: invention relates to an improved method of producing 3-aminomethyl-3,5,5-trimethylcylohexylamine (IPDA). Method comprises steps a) reaction of 3-cyano-3,5,5-trimethylcyclohexanone (IPN) with excess primary amine, with removal of formed water, as a result of which IPN is substantially converted to imine compounds; b) mixing product from step a) with liquid ammonia in presence of an ammonolysis catalyst at temperature from 20 to 200 °C and at pressure from 10 to 30 MPa; and as a result of which said imine compounds enter into ammonolysis reaction to form 3-cyano-3,5,5-trimethylcyclohexylimine (IPNI) and primary amine; and c) hydrogenation of IPNI obtained at step b), in presence of hydrogen and a hydrogenation catalyst to obtain 3-aminomethyl-3,5,5-trimethylcyclohexylamine (IPDA). Method may also include a step d), including: separation of primary amine from IPDA in product, obtained at step c), for example, by rectification. Said primary amine is returned to step a) for repeated use. Primary amine used at step a) is monoamin or diamine selected from a group, consisting of C_1-30alkylamines, C_3-30cycloalkylamines, C_6-30arylamines and C_7-30arylalkylamines. Preferably primary amine used has a boiling point in range of 110 to 235 °C. Primary amine used at step a) can be IPDA obtained at step c). Molar ratio of all amino groups (-NH₂) of primary amine to IPN at step a) ranges from 1 to 20. Water at step a) is removed by adsorption, extraction or distillation, mainly at low pressure. Step a) is usually performed at pressure of 100 kPa or less, and temperature 20–150 °C. Water content in product obtained at step a) is 300 ppm or less. Preferred molar ratio of liquid ammonia to IPN, used as starting material at step a) ranges from 5 to 200. Ammonolysis catalyst used at step b) can be an acid metal oxide, selected from a group consisting of γ-aluminium oxide, titanium dioxide, zirconium dioxide, silica; or zeolite. Step c) is preferably carried out at temperature from 100 to 200 °C and pressure from 10 to 30 MPa using a hydrogenation catalyst, selected from Raney metal catalysts, for example Raney cobalt or Raney nickel. Method enables to avoid formation of 3,3,5-trimethylcyclohexanol and 3-aminomethyl-3,5,5-trimethylcyclohexanol, which are main by-products formed in existing methods, thus increases output of 3-aminomethyl-3,5,5-trimethylcyclohexylamine to 98.2–98.8 %.

EFFECT: improved method of producing 3-aminomethyl-3,5,5-trimethylcyclohexylamine.

35 cl, 1 dwg, 7 tbl, 19 ex