octyl carbamate

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

Procedure: A 1000 mL glass flask equipped with a reflux condenser, a gas-liquid separator, and a stirrer was charged with 522.4 g (4.01 mol) of 1-octanol and 60.07 g (1.00 mol) of urea. While the mixture was stirred at 500 rpm and nitrogen gas was allowed to flow at 30 mL per minute, the mixture was allowed to react at 165° C. After 90 min, 52.1 g (0.87 mol) of urea was added, and after 120 min, 49.34 g (0.82 mol) of urea was added, and the mixture was allowed to react at a reaction temperature of 165° C. A 1000 mL glass flask equipped with a reflux condenser to react at 165° C after 120 min to react at a reaction temperature of 165° C.

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

Procedure: Agitated in a reaction vessel are 256 parts of N,N'-bis(2,2-dimethyl-3-aminopropyl)piperazine with 400 parts of O-octyl carbamate and 130 parts of n-octanol at a reflux temperature of 190° C.-200° C. for 1 hour while the ammonia is removed by distillation. At that point, an additional 650 parts of n-octanol are allowed to flow into the reaction mixture and the reaction is continued at reflux temperature for 7 hours. Unreacted octanol and O-octylcarbonate are removed by distillation up to a sump temperature of 180° C.-200° C. at 2 millibars. By transcrystallization of the residue from acetone/water, 506 parts of N,N'-bis(octoxycarbonylaminoneopentyl)piperazine, C32H64N4O4 (molecular weight 568), are obtained corresponding with 89 percent of theory relative to N,N'-bis(2,2-dimethyl-3-aminopropyl)piperaxine. The melting point is 66° C.-68° C. at a reflux temperature of 190° C.-200° C. for 1 hour is removed by distillation at reflux temperature for 7 hours are removed by distillation up to a sump temperature of 180° C.-200° C. at 2 millibars

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

Procedure: Agitated in a reaction vessel are 256 parts of N,N'-bis(2,2-dimethyl-3-aminopropyl)piperazine with 400 parts of O-octyl carbamate and 130 parts of n-octanol at a reflux temperature of 190° C.-200° C. for 1 hour while the ammonia is removed by distillation. At that point, an additional 650 parts of n-octanol are allowed to flow into the reaction mixture and the reaction is continued at reflux temperature for 7 hours. Unreacted octanol and O-octylcarbonate are removed by distillation up to a sump temperature of 180° C.-200° C. at 2 millibars. By transcrystallization of the residue from acetone/water, 506 parts of N,N'-bis(octoxycarbonylaminoneopentyl)piperazine, C32H64N4O4 (molecular weight 568), are obtained corresponding with 89 percent of theory relative to N,N'-bis(2,2-dimethyl-3-aminopropyl)piperaxine. The melting point is 66° C.-68° C. at a reflux temperature of 190° C.-200° C. for 1 hour is removed by distillation at reflux temperature for 7 hours are removed by distillation up to a sump temperature of 180° C.-200° C. at 2 millibars

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Agitated in a reaction vessel are 210 parts of 4,4'-diaminodicyclohexylmethane with 360 parts of O-octyl carbamate and 150 parts of n-octanol-(1) at a reflux temperature of 185° C.-205° C. for 2 hours while the ammonia is removed by means of distillation. At this point, an additional 650 parts of n-octanol are allowed to flow into the reaction mixture and the reaction is continued at reflux temperature for 10 hours. The reaction mixture, which has been cooled to 100° C., is filtered, and the product is allowed to crystallize by cooling the filtrate. By filtration, washing with octanol and drying, 468 parts of bis(4-octoxycarbonylaminocyclohexyl)methane, C31H58N2O4 (molecular weight 522) are obtained corresponding with 89.6 percent theory relative to 4,4'-bisaminodicyclohexylmethane. The melting point is 129° C.-130° C. at a reflux temperature of 185° C.-205° C. for 2 hours is removed by means of distillation at reflux temperature for 10 hours is filtered to crystallize by cooling the filtrate By filtration washing with octanol drying

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Agitated in a reaction vessel are 116 parts of 1,6-hexamethylenediamine with 380 parts of O-octyl carbamate and 130 parts of n-octanol-(1) at a reflux temperature of 185° C.-205° C. for 2 hours while the ammonia is removed by distillation. At this point, an additional 500 parts of n-octanol-(1) are allowed to flow into the reaction mixture and the reaction is continued at reflux temperature for 7 hours. The reaction mixture, cooled to 110° C., is filtered, and the reaction product is allowed to crystallize by cooling. By filtration, washing with n-octanol-(1) and drying, 388 parts of 1,6-bis(octoxycarbonylamino)hexane are obtained corresponding with 90.6 percent theory relative to 1,6-hexamethylenediamine. The melting point is 107° C.-109° C. at a reflux temperature of 185° C.-205° C. for 2 hours is removed by distillation at reflux temperature for 7 hours is filtered to crystallize by cooling By filtration washing with n-octanol-(1) drying

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Agitated in a reaction vessel are 116 parts of 1,6-hexamethylenediamine with 380 parts of O-octyl carbamate and 130 parts of n-octanol-(1) at a reflux temperature of 185° C.-205° C. for 2 hours while the ammonia is removed by distillation. At this point, an additional 500 parts of n-octanol-(1) are allowed to flow into the reaction mixture and the reaction is continued at reflux temperature for 7 hours. The reaction mixture, cooled to 110° C., is filtered, and the reaction product is allowed to crystallize by cooling. By filtration, washing with n-octanol-(1) and drying, 388 parts of 1,6-bis(octoxycarbonylamino)hexane are obtained corresponding with 90.6 percent theory relative to 1,6-hexamethylenediamine. The melting point is 107° C.-109° C. at a reflux temperature of 185° C.-205° C. for 2 hours is removed by distillation at reflux temperature for 7 hours is filtered to crystallize by cooling By filtration washing with n-octanol-(1) drying

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

Procedure: Agitated in a reaction vessel are 116 parts of 1,6-hexamethylenediamine with 346 parts of O-octyl carbamate, 3 parts sodium octylate and 1500 parts of n-octanol at a reflux temperature of 185° C.-195° C. for 12 hours while the ammonia is removed by distillation. The resulting precipitate is removed from the reaction mixture by means of filtration after cooling to 100° C.-110° C. The reaction is allowed to crystallize by cooling to room temperature. By means of filtration, washing with n-octanol and drying, 242 parts of 1,6-bis(octoxycarbonylamino)hexane is obtained corresponding with 56.5 percent of theory. The melting point is 106° C.-107° C. at a reflux temperature of 185° C.-195° C. for 12 hours is removed by distillation The resulting precipitate is removed from the reaction mixture by means of filtration after cooling to 100° C.-110° C to crystallize By means of filtration washing with n-octanol drying

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

Procedure: Agitated in a reaction vessel are 116 parts of 1,6-hexamethylenediamine with 346 parts of O-octyl carbamate and 2000 parts of n-octanol-(1) at a reflux temperature of 185° C.-195° C. for 16 hours while the ammonia is removed by distillation. The precipitate formed in the reaction mixture, cooled to 100° C.-110° C., is removed by filtration. The reaction product is allowed to crystallize by cooling to room temperature. By means of filtration, washing with n-octanol-(1) and drying, 236 parts of 1,6-bis(octoxycarbonylamino)hexane, C24H48N2O4 (molecular weight 428), are obtained corresponding with 55 percent of theory relative to 1,6-hexamethylenediamine and O-octylcarbamate. The melting point is 106° C.-108° C. (from ethyl acetate). at a reflux temperature of 185° C.-195° C. for 16 hours is removed by distillation The precipitate formed in the reaction mixture cooled to 100° C.-110° C. is removed by filtration to crystallize By means of filtration washing with n-octanol-(1) drying

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

Procedure: Agitated in a reaction vessel are 116 parts of 1,6-hexamethylenediamine with 346 parts of O-octyl carbamate and 2000 parts of n-octanol-(1) at a reflux temperature of 185° C.-195° C. for 16 hours while the ammonia is removed by distillation. The precipitate formed in the reaction mixture, cooled to 100° C.-110° C., is removed by filtration. The reaction product is allowed to crystallize by cooling to room temperature. By means of filtration, washing with n-octanol-(1) and drying, 236 parts of 1,6-bis(octoxycarbonylamino)hexane, C24H48N2O4 (molecular weight 428), are obtained corresponding with 55 percent of theory relative to 1,6-hexamethylenediamine and O-octylcarbamate. The melting point is 106° C.-108° C. (from ethyl acetate). at a reflux temperature of 185° C.-195° C. for 16 hours is removed by distillation The precipitate formed in the reaction mixture cooled to 100° C.-110° C. is removed by filtration to crystallize By means of filtration washing with n-octanol-(1) drying

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

Procedure: A Fischer-Porter bottle was charged with 0.55 g (4.2 mmol) of octyl amine, 0.99 g of P1 tBu (3 mmol), 25 mL of acetonitrile and 130 mg (0.84 mmol) of tridecane as an internal standard. The bottle was pressurized to 80 psig with carbon dioxide and the solution was stirred for 30 min. at room temperature. A second Ficher-Porter bottle was charged with 0.65 g (4.7 mmol) of sulfur trioxide trimethylamine adduct (SO3 -NMe3) and 20 mL of acetonitrile then pressurized to 80 psig with CO2. The two solutions were cooled to 0° C. in an ice bath for 10 min after which time the octyl carbamate solution was added rapidly to the SO3 -NMe3 suspension. An aliquot was taken after five minutes and diluted with diethyl ether prior to G.C. analysis which indicated a yield of 11% octyl isocyanate. Further monitoring of the reaction progress over 48 hrs gave a maximum yield of 27% octyl isocyanate. An aliquot was taken after five minutes

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

Procedure: A Fischer-Porter bottle was charged with 0.65 g (5 mmol) of octyl amine, 2.74 g of BEMP (10 mmol), 25 mL of acetonitrile and 184 mg (1 mmol) of tridecane as an internal standard. The bottle was pressurized to 80 psig with carbon dioxide and the solution was stirred for 30 min. at room temperature. A second Fischer-Porter bottle was charged with 0.71 mL (5 mmol) of trifluoroacetic anhydride and 25 mL of acetonitrile then pressurized to 80 psig with CO2. The two solutions were cooled to 0° C. in an ice bath for 10 minutes after which time the octyl carbamate solution was added rapidly to the trifluoroacetic anhydride solution. An aliquot was taken after five minutes and diluted with diethyl ether prior to G.C. analysis which indicated a yield of 83% octyl isocyanate. The reaction mixture was allowed to warm slowly to room temperature and aliquots were taken periodically for G.C. analysis. A maximum yield of 85% octyl isocyanate was obtained after ca. 30 minutes. An aliquot was taken after five minutes

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

Procedure: A 1000 mL glass flask equipped with a reflux condenser, a gas-liquid separator, and a stirrer was charged with 522.4 g (4.01 mol) of 1-octanol and 60.07 g (1.00 mol) of urea. While the mixture was stirred at 500 rpm and nitrogen gas was allowed to flow at 30 mL per minute, the mixture was allowed to react at 165° C. After 90 min, 52.1 g (0.87 mol) of urea was added, and after 120 min, 49.34 g (0.82 mol) of urea was added, and the mixture was allowed to react at a reaction temperature of 165° C. A 1000 mL glass flask equipped with a reflux condenser to react at 165° C after 120 min to react at a reaction temperature of 165° C.