hexanedinitrile

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: DE-A-2 429 293 discloses in Example 1 that the hydrogenation of adiponitrile in the presence of five times the weight of ammonia at from 93 to 98° C. (inlet temperature into the reactor) or at from 94 to 104° C. (outlet temperature) over an iron catalyst prepared from magnetite by reduction with hydrogen and doped with aluminum oxide, silicon dioxide, calcium oxide and vanadium pentoxide yields 98.22% of hexamethylenediamine comprising 1900 ppm of 1,2-diaminocyclohexane, and in Example 2 that the hydrogenation of adiponitrile in the presence of five times the weight of ammonia at from 93 to 98° C. (inlet temperature into the reactor) or at from 94 to 104° C. (outlet temperature) over an iron catalyst prepared from Labrador hematite ore (Fe2O3) by reduction with hydrogen and doped with aluminum oxide, silicon dioxide and calcium oxide yields 98.05% of hexamethylenediamine comprising 3500 ppm of 1,2-diaminocyclohexane.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: DE-A-2 429 293 discloses in Example 1 that the hydrogenation of adiponitrile in the presence of five times the weight of ammonia at from 93 to 98° C. (inlet temperature into the reactor) or at from 94 to 104° C. (outlet temperature) over an iron catalyst prepared from magnetite by reduction with hydrogen and doped with aluminum oxide, silicon dioxide, calcium oxide and vanadium pentoxide yields 98.22% of hexamethylenediamine comprising 1900 ppm of 1,2-diaminocyclohexane, and in Example 2 that the hydrogenation of adiponitrile in the presence of five times the weight of ammonia at from 93 to 98° C. (inlet temperature into the reactor) or at from 94 to 104° C. (outlet temperature) over an iron catalyst prepared from Labrador hematite ore (Fe2O3) by reduction with hydrogen and doped with aluminum oxide, silicon dioxide and calcium oxide yields 98.05% of hexamethylenediamine comprising 3500 ppm of 1,2-diaminocyclohexane.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of diisopropylamine (20.24 g, 0.2 mol), methallyl chloride (9.00 g, 0.1 mol), adiponitrile (10.81 g, 0.1 mol) and tetrabutylammonium iodide (3.69 g, 10 mmol) was refluxed for 5 h with vigorous stirring (two phases). The temperature of the mixture increased from 88° to 125° C. Potassium hydroxide solution (5M, 15 ml, 0.15 mol) was added. Three layers formed. The mixture was extracted with n-pentane (2×50 ml). Adiponitrile (the middle layer) was recovered. The pentane solution was dried with anhydrous magnesium sulfate and the product was isolated by distillation: 12.58 g (81%), bp 75-77° C/45 mm Hg. 1H NMR CDCl3 δ ppm, 0.98 (d, J=6.6 Hz, 12H, CH3), 1.70 (s, 3H, CH3), 2.97 (m, 4H, CH2, CH), 4.78 (s, 1H,=CH2), 4.93 (m, 1H,=CH2) . was refluxed for 5 h The temperature of the mixture increased from 88° to 125° C Three layers formed The mixture was extracted with n-pentane (2×50 ml) Adiponitrile (the middle layer) was recovered The pentane solution was dried with anhydrous magnesium sulfate the product was isolated by distillation

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of tert-butylamine (10.97 g, 0.15 mol), isobutyl bromide (13.70 g, 0.1 mol), adiponitrile (10.81 g, 0.1 mol) and tetrabutylammonium iodide (1.85 g, 5 mmol) was refluxed with stirring for 12 hours. Aqueous 5 M potassium hydroxide (30 ml, 0.15 mmol) was added and the mixture was extracted with n-pentane (2×50 ml). Three layers were formed. Adiponitrile (the middle layer) was recovered. The pentane solution was dried over anhydrous magnesium sulfate and the product was isolated by distillation to yield 9.5 g, (74%), bp 45-47° C./40 mm Hg; 1H NMR (CDCl3) δ0.91 (d, J=6.5 Hz, 6H, CH3), 1.08 (s, 9H, CH3), 1.64 (sep, J=6.5 Hz, 1H, CH), 2.34 (d, J=6.5 Hz, 2H, CH2). was refluxed the mixture was extracted with n-pentane (2×50 ml) Three layers were formed Adiponitrile (the middle layer) was recovered The pentane solution was dried over anhydrous magnesium sulfate the product was isolated by distillation to yield 9.5 g, (74%), bp 45-47° C./40 mm Hg

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The product of the hydrocyanation of butadiene using a nickel catalyst and a boron promoter contains 2-methylglutaronitrile, adiponitrile, phenyl t-butylcatecholboronate, and other organo boron compounds such as triphenyl boron, phenyl boronic acid, its anhydride and its phenol and cresol esters. (The t-butylcatecholboronate is formed by the reaction of t-butylcatechol with a boron compound. The t-butylcatechol is an additive used to inhibit the polymerization of butadiene.) This mixture is combined with the alcohol (e.g. ethylene glycol) in at least stoichiometric quantity relative to boron, and the mixture is distilled using a column with sufficient stages to separate out purified adiponitrile as the bottoms, and a mixture of 2-methylglutaronitrile, any excess alcohol (e.g. ethylene glycol), phenol, cresols, and the newly formed boron-complex, (e.g. phenyl ethyleneglycolboronate) as the overheads. (The adiponitrile bottoms may contain some t-butylcatechol at this point, depending on the efficiency of the column.) The overhead mixture is then further distilled in a second column to remove low boilers consisting of any excess ethylene glycol, phenol, cresols, and phenyl ethyleneglycolboronate. 2-methylglutaronitrile is removed as the bottoms, which are then sent to a third column where pure 2-methylglutaronitrile is taken overhead. The bottoms from this last column consist of t-butylcatechol and a small amount of adiponitrile.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 0.4 liter/hour of adipodinitrile, 1.2 liter/hour of ammonia and 2.4 liters/hour of hydrogenation mixture are fed, at 270° C. and under an H2 pressure of 260 bar, into the reactor described in Example 1, and over the catalyst described in that Example. Azacycloheptane is obtained in a yield of 70% together with 3% of bishexamethylenetriamine, 7% of hexylamine and 15% of hexamethylenediamine. are fed, at 270° C. and under an H2

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: After the cooling process, the high pressure vessel is charged, by a trickle-bed procedure and under a hydrogen pressure of 270 bar, with 0.4 liters/hour of adipodinitrile, 1.2 liters/hour of liquid ammonia and 4.5 liters/hour of crude hydrogenation mixture, the temperature in this procedure being kept at 140° C. Analysis of the crude hexamethylenediamine by gas chromatography after the ammonia has been evaporated from the hydrogenation mixture gives 99.69% by weight of hexamethylenediamine, 0.06% by weight of 1,2-diaminocyclohexane and 0.12% by weight of 2-aminocyclopentylamine. After the cooling process, the high pressure vessel is charged, by a trickle-bed procedure and under a hydrogen pressure of 270 bar being kept at 140° C Analysis of the crude hexamethylenediamine by gas chromatography after the ammonia has been evaporated from the hydrogenation mixture

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: After the cooling process, the high pressure vessel is charged, by a trickle-bed procedure and under a hydrogen pressure of 270 bar, with 0.4 liters/hour of adipodinitrile, 1.2 liters/hour of liquid ammonia and 4.5 liters/hour of crude hydrogenation mixture, the temperature in this procedure being kept at 140° C. Analysis of the crude hexamethylenediamine by gas chromatography after the ammonia has been evaporated from the hydrogenation mixture gives 99.69% by weight of hexamethylenediamine, 0.06% by weight of 1,2-diaminocyclohexane and 0.12% by weight of 2-aminocyclopentylamine. After the cooling process, the high pressure vessel is charged, by a trickle-bed procedure and under a hydrogen pressure of 270 bar being kept at 140° C Analysis of the crude hexamethylenediamine by gas chromatography after the ammonia has been evaporated from the hydrogenation mixture

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: DE-A-2 429 293 discloses in Example 1 that the hydrogenation of adiponitrile in the presence of five times the weight of ammonia at from 93 to 98° C. (inlet temperature into the reactor) or at from 94 to 104° C. (outlet temperature) over an iron catalyst prepared from magnetite by reduction with hydrogen and doped with aluminum oxide, silicon dioxide, calcium oxide and vanadium pentoxide yields 98.22% of hexamethylenediamine comprising 1900 ppm of 1,2-diaminocyclohexane, and in Example 2 that the hydrogenation of adiponitrile in the presence of five times the weight of ammonia at from 93 to 98° C. (inlet temperature into the reactor) or at from 94 to 104° C. (outlet temperature) over an iron catalyst prepared from Labrador hematite ore (Fe2O3) by reduction with hydrogen and doped with aluminum oxide, silicon dioxide and calcium oxide yields 98.05% of hexamethylenediamine comprising 3500 ppm of 1,2-diaminocyclohexane.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: DE-A-2 429 293 discloses in Example 1 that the hydrogenation of adiponitrile in the presence of five times the weight of ammonia at from 93 to 98° C. (inlet temperature into the reactor) or at from 94 to 104° C. (outlet temperature) over an iron catalyst prepared from magnetite by reduction with hydrogen and doped with aluminum oxide, silicon dioxide, calcium oxide and vanadium pentoxide yields 98.22% of hexamethylenediamine comprising 1900 ppm of 1,2-diaminocyclohexane, and in Example 2 that the hydrogenation of adiponitrile in the presence of five times the weight of ammonia at from 93 to 98° C. (inlet temperature into the reactor) or at from 94 to 104° C. (outlet temperature) over an iron catalyst prepared from Labrador hematite ore (Fe2O3) by reduction with hydrogen and doped with aluminum oxide, silicon dioxide and calcium oxide yields 98.05% of hexamethylenediamine comprising 3500 ppm of 1,2-diaminocyclohexane.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: DE-A-2 429 293 discloses in Example 1 that the hydrogenation of adiponitrile in the presence of five times the weight of ammonia at from 93 to 98° C. (inlet temperature into the reactor) or at from 94 to 104° C. (outlet temperature) over an iron catalyst prepared from magnetite by reduction with hydrogen and doped with aluminum oxide, silicon dioxide, calcium oxide and vanadium pentoxide yields 98.22% of hexamethylenediamine comprising 1900 ppm of 1,2-diaminocyclohexane, and in Example 2 that the hydrogenation of adiponitrile in the presence of five times the weight of ammonia at from 93 to 98° C. (inlet temperature into the reactor) or at from 94 to 104° C. (outlet temperature) over an iron catalyst prepared from Labrador hematite ore (Fe2O3) by reduction with hydrogen and doped with aluminum oxide, silicon dioxide and calcium oxide yields 98.05% of hexamethylenediamine comprising 3500 ppm of 1,2-diaminocyclohexane.