hexane-1,6-diamine

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

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

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

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

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

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

Procedure: Compound 12 was prepared using the methodology described for the preparation of compound 9, by substituting 1,5-diaminopentane with 1,6-diaminohexane and phenylisocyanate with (4-isocyanato-phenyl)-dimethyl-amine. 1H NMR (300 MHz, DMSO-d6) δ (ppm) 7.98 (br s, 1H), 7.05 (d, J=8.7 Hz, 2H), 6.60 (d, J=8.7 Hz, 2H), 6.04 (br t, J=5.7 Hz, 1H), 5.80 (br t, J=5.7 Hz, 1H), 4.05 (d, J=5.7 Hz, 2H), 3.06 (d, J=8.1 Hz, 2H), 3.04 (dt, J=6.9, 6.0 Hz, 2H), 2.98 (dt, J=6.6, 6.0 Hz, 2H), 2.84 (s, 6H), 2.71 (t, J=8.1 Hz, 1H), 1.36 (m, 4H), 1.24 (m, 4H). 13C NMR (75 MHz, DMSO-d6) δ (ppm) 169.2, 157.9, 149.3, 127.9, 126.9, 112.3, 42.4, 40.3, 39.1, 38.7, 30.0, 29.0, 27.1, 26.12, 26.08.

Conditions: temp:270.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 50 wt % aqueous solution of salt (AH salt) of adipic acid with hexamethylenediamine, and ∈-caprolactam (CL) were mixed so that AH salt was 20 parts by weight and CL was 80 parts by weight, and the mixture was charged in an autoclave of 30 liters. After it was raised to 270° C. at an internal pressure of 10 kg/cm2, the internal temperature was maintained at 245° C., while stirring, the pressure was slowly reduced to 0.5 kg/cm2 and stirring was stopped. After being returned to normal pressure by nitrogen, a strand was drawn out, pelletized, and unreacted substances were extracted out using boiling water, and dried. The thus obtained copolyamide 6/66 resin had a relative viscosity of 4.20 and melting point of 193° C. were mixed so that AH salt the mixture was charged in an autoclave of 30 liters the internal temperature was maintained at 245° C. stirring unreacted substances were extracted dried

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

Procedure: To a catalyst basket in a 300 milliliter Parr reactor was charged 5.044 grams of a nickel, rhenium, boron catalyst prepared as described in Example 6 of U.S. Pat. No. 4,123,462. The catalyst was activated in 50 milliliters of water for 1 hour at 200° C. under 533 psig hydrogen. The reactor was cooled, vented, and the water discharged. 50 Milliliters of 17% NH3 in water was charged to the reactor and the reactor was heated to 235° C. under 220 psig of 3% hydrogen in nitrogen. A flow of 40 milliliters per minute of 3% hydrogen in nitrogen was maintained through the reactor using a Brooks Mass Flow Meter at a reactor pressure of 725 psig. A solution of 5.00 grams of 6-aminohexanol, 20 grams water and 2.04 grams of tetreglyme as internal standard was prepared and charged to a stainless steel pressure cylinder connected to a metering pump. The 6-aminohexanol in water solution was fed to the reactor at a rate of 1.0 milliliter per minute. The yields of products, i.e., epsilon caprolactam, hexamethyleneimine, and hexamethylenediamine, were determined using gas chromatographic analysis of samples taken over time and were based on the amount of 6-aminohexanol charged. From the time when the 6-aminohexanol feed was completed, the yields of epsilon caprolactam, hexamethyleneimine, and hexamethylenediamine with are shown in the table below. prepared The reactor was cooled

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

Procedure: 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.

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

Procedure: 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.

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 300 g of allylmethylbicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride are taken and heated to 130° C., and 79.9 g of melted hexamethylene diamine are added dropwise, with stirring. Water is removed by distillation, the temperature is raised to 180° C. and the pressure is reduced to 53 Pa. 180° C. and 53 Pa are maintained for 15 minutes. This gives 345 g (97% of theory) of a brown, viscous resin having a viscosity of 1.356 Pa.s at 80° C. Water is removed by distillation the temperature is raised to 180° C. 180° C. and 53 Pa are maintained for 15 minutes at 80° C.

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

Procedure: Using the general method of Example 9 Part A, hexamethylenediamine (348.63 g, 3 mol) was reacted with benzamide (121.14 g, 1 mole) to provide 136.5 g of N-(6-aminohexyl)benzamide.