N'-cyclohexylethane-1,2-diamine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In this example the ratio of ethylenediamine:cyclohexanone, the reaction temperature, and the H2 :feed ratio were varied using as a catalyst 0.3 weight percent platinum (sulfided) on gamma-alumina in a non-aqueous environment. Samples were taken every 6 hours to afford the results in Table 1. to afford the results in Table 1

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 850 cc glass liner for a rotating autoclave was charged 12.25 g (0.125 mole) cyclohexanone, 3.7 g of a catalyst consisting of 0.3 weight percent platinum (sulfided) on alpha alumina, and an 80 weight percent solution of ethylenediamine in de-ionized water (37.5 g (0.63 mole) ethylenediamine and 9.37 g (0.52 mole) water). An exotherm was generated immediately associated with the formation of Schiff bases from the reaction of cyclohexanone and ethylenediamine. The liner was placed into a rotating autoclave, purged with nitrogen, charged to 1,000 psig with hydrogen or 500 psig each of hydrogen and nitrogen, and then the autoclave was rotated at approximately 30 rpm for 6-8 hours at 160°-180° C. The cooled liner was vented, flushed with nitrogen to avoid catalyst ignition, and the cooled product mixture was removed to afford a clear to pale yellow viscous liquid containing some solids which were principally N,N'-dicylohexyl ethylenediamine (DICEDA). The product mixture was filtered through diatomaceous earth to remove catalyst and DICEDA, and the resulting filtrate contained, in addition to unreacted ethylenediamine, CEDA with only traces of DICEDA. The liner and filter cake were rinsed with methanol and subsequent removal of volatile material at 80° C. afforded product which was principally DICEDA. Removal of volatiles at 80° C. at 30 inches vacuum afforded 15 grams CEDA. Conversion of cyclohexanone amounted to 99+% with a 95% yield of CEDA and 5% DICEDA. purged with nitrogen charged to 1,000 psig with hydrogen or 500 psig each of hydrogen and nitrogen flushed with nitrogen the cooled product mixture was removed to afford a clear to pale yellow viscous liquid containing some solids which The product mixture was filtered through diatomaceous earth to remove catalyst and DICEDA the resulting filtrate contained, in addition to unreacted ethylenediamine, CEDA with only traces of DICEDA The liner and filter cake were rinsed with methanol and subsequent removal of volatile material at 80° C. afforded product which Removal of volatiles at 80° C. at 30 inches vacuum afforded 15 grams CEDA

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of cyclohexanone (6.260 g, 63.8 mmol), ethylenediamine (42.640 mL, 637.8 mmol), acetic acid (36.515 mL, 637.8 mmol), and 4 {acute over (Å)} molecular sieves (25 g) in anhydrous methanol (250 mL) was added sodium cyanoborohydride (8.017 g, 127.6 mmol). The mixture was stirred for 48 hrs, filtered to remove the solids, and concentrated in vacuo. The residue was dissolved in 3 N aqueous sodium hydroxide (150 mL) and extracted with methylene chloride (3×300 mL). The combined organic layers were washed with basic saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated to give the crude product. The material was vacuum distilled to give the desired product as a clear liquid (4.1 g, 45%). 1H NMR (300 MHz, CDCl3) δ 2.80-2.76 (td, 2H, J=0.9, 6.0 Hz), 2.68-2.64 (td, 2H, J=0.9, 6.0 Hz), 2.43-2.34 (m, 1H), 1.89-1.83 (m, 2H), 1.74-1.70 (m, 2H), 1.62-1.57 (m, 1H), 1.32-0.98 (m, 8H). filtered to remove the solids concentrated in vacuo The residue was dissolved in 3 N aqueous sodium hydroxide (150 mL) extracted with methylene chloride (3×300 mL) The combined organic layers were washed with basic saturated aqueous sodium chloride dried (anhydrous sodium sulfate) filtered concentrated to give the crude product distilled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclohexanone (50 g) and ethylene diamine (60 g) were mixed in ethanol (50 ml) at room temperature and allowed to stand for one hour. Meanwhile Adams catalyst (1 g) in ethanol (20 ml) was pre-reduced on a Parr apparatus at 60 p.s.i. under hydrogen for one hour. The imine solution was added to the hydrogenation flask and reduced at 60 p.s.i. for 18 hours. The catalyst was removed by filtration and the ethanol removed under vacuum. N-Cyclohexyl ethylene diamine was obtained on distillation of the crude product collecting the fraction boiling between 110°-120° C. at 20 ram. under hydrogen for one hour for 18 hours The catalyst was removed by filtration the ethanol removed under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In this example the ratio of ethylenediamine:cyclohexanone, the reaction temperature, and the H2 :feed ratio were varied using as a catalyst 0.3 weight percent platinum (sulfided) on gamma-alumina in a non-aqueous environment. Samples were taken every 6 hours to afford the results in Table 1. to afford the results in Table 1

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 850 cc glass liner for a rotating autoclave was charged 12.25 g (0.125 mole) cyclohexanone, 3.7 g of a catalyst consisting of 0.3 weight percent platinum (sulfided) on alpha alumina, and an 80 weight percent solution of ethylenediamine in de-ionized water (37.5 g (0.63 mole) ethylenediamine and 9.37 g (0.52 mole) water). An exotherm was generated immediately associated with the formation of Schiff bases from the reaction of cyclohexanone and ethylenediamine. The liner was placed into a rotating autoclave, purged with nitrogen, charged to 1,000 psig with hydrogen or 500 psig each of hydrogen and nitrogen, and then the autoclave was rotated at approximately 30 rpm for 6-8 hours at 160°-180° C. The cooled liner was vented, flushed with nitrogen to avoid catalyst ignition, and the cooled product mixture was removed to afford a clear to pale yellow viscous liquid containing some solids which were principally N,N'-dicylohexyl ethylenediamine (DICEDA). The product mixture was filtered through diatomaceous earth to remove catalyst and DICEDA, and the resulting filtrate contained, in addition to unreacted ethylenediamine, CEDA with only traces of DICEDA. The liner and filter cake were rinsed with methanol and subsequent removal of volatile material at 80° C. afforded product which was principally DICEDA. Removal of volatiles at 80° C. at 30 inches vacuum afforded 15 grams CEDA. Conversion of cyclohexanone amounted to 99+% with a 95% yield of CEDA and 5% DICEDA. purged with nitrogen charged to 1,000 psig with hydrogen or 500 psig each of hydrogen and nitrogen flushed with nitrogen the cooled product mixture was removed to afford a clear to pale yellow viscous liquid containing some solids which The product mixture was filtered through diatomaceous earth to remove catalyst and DICEDA the resulting filtrate contained, in addition to unreacted ethylenediamine, CEDA with only traces of DICEDA The liner and filter cake were rinsed with methanol and subsequent removal of volatile material at 80° C. afforded product which Removal of volatiles at 80° C. at 30 inches vacuum afforded 15 grams CEDA

Conditions: temp:0.00; pressure:0.00; stir: