dodecane-1,12-diamine

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

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

Procedure: polyamide of dodecamethylenediamine and n-dodecanedioic acid (nylon 12:12)

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

Procedure: polyamide of dodecamethylenediamine and n-dodecanedioic acid (nylon 12:12)

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

Procedure: polyamide of dodecamethylenediamine and n-dodecanedioic acid (nylon 12:12)

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

Procedure: Chloromethanephosphonic acid (15.1 g, 115.7 mmoles) and 1,12-diaminododecane (100 g, 0.5 moles) were heated under reflux in water (160 cm3) for 20 hours. The water was then distilled off and ethanol (250 cm3) was added. The phosphonic acid was filtered off and dried. The crude yield was 30.7 g (85%). A sample was purified by recrystallization from water/ethanol to give N-(12-aminododecyl)-aminomethanephosphonic acid monohydrate as a fine white crystalline solid having a melting point of 234° C. The water was then distilled off ethanol (250 cm3) was added The phosphonic acid was filtered off dried A sample was purified by recrystallization from water/ethanol

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 0.059 mmol RuHCl(H2)(PCy3)2, 2.87 mmol dodecanedinitrile, 5 mL water and 35 mL toluene was stirred in a Fisher-Porter tube at 80° C. under 860 kPa H2. After 22 hours, gc analysis showed that the dinitrile was completely converted and the product, 1,12-dodecanediamine, formed in 85% yield.

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 0.059 mmol RuHCl(H2)(PCy3)2, 2.87 mmol dodecanedinitrile, 5 mL water and 35 mL toluene was stirred in a Fisher-Porter tube at 80° C. under 860 kPa H2. After 22 hours, gc analysis showed that the dinitrile was completely converted and the product, 1,12-dodecanediamine, formed in 85% yield.

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

Procedure: 34 g (0.216 mol) 2-nitro-chlorobenzene and 20 g 1,12-diaminododecane (0.10 mol) are mixed with 40 g potassium carbonate and 200 ml N,N-dimethylformamide (DMF). The mixture is heated with reflux while subjected to a vigorous stirring for four hours. Subsequently, the inorganic salts are filtered off and washed with a small amount of DMF. The entire DMF-phase is distilled under vacuum to remove substantially all DMF. The remanence is cooled, and 200 ml water are added while vigorously stirred. Subsequently, the water phase is decanted off, and the product is caused to crystallize by the addition of approximately 100 ml ethanol. The crystals are filtered off, washed twice with 25 ml ethanol and 100 ml petroleum ether followed by an air-drying of the product. Yield 21.8 g (49%), melting point 79° to 80° C. The mixture is heated with reflux Subsequently, the inorganic salts are filtered off washed with a small amount of DMF The entire DMF-phase is distilled under vacuum to remove substantially all DMF The remanence is cooled 200 ml water are added while vigorously stirred Subsequently, the water phase is decanted off to crystallize by the addition of approximately 100 ml ethanol The crystals are filtered off washed twice with 25 ml ethanol and 100 ml petroleum ether an air-drying of the product

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

Procedure: 34 g (0.216 mol) 2-nitro-chlorobenzene and 20 g 1,12-diaminododecane (0.10 mol) are mixed with 40 g potassium carbonate and 200 ml N,N-dimethylformamide (DMF). The mixture is heated with reflux while subjected to a vigorous stirring for four hours. Subsequently, the inorganic salts are filtered off and washed with a small amount of DMF. The entire DMF-phase is distilled under vacuum to remove substantially all DMF. The remanence is cooled, and 200 ml water are added while vigorously stirred. Subsequently, the water phase is decanted off, and the product is caused to crystallize by the addition of approximately 100 ml ethanol. The crystals are filtered off, washed twice with 25 ml ethanol and 100 ml petroleum ether followed by an air-drying of the product. Yield 21.8 g (49%), melting point 79° to 80° C. The mixture is heated with reflux Subsequently, the inorganic salts are filtered off washed with a small amount of DMF The entire DMF-phase is distilled under vacuum to remove substantially all DMF The remanence is cooled 200 ml water are added while vigorously stirred Subsequently, the water phase is decanted off to crystallize by the addition of approximately 100 ml ethanol The crystals are filtered off washed twice with 25 ml ethanol and 100 ml petroleum ether an air-drying of the product

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 30.04 gm (0.240 mole) of cyclohexyl isocyanate was dissolved in 400 mL of 1:1 THF/toluene in a 1000 mL round bottom, 3-neck flask equipped with a thermometer, magnetic stirrer, pressure equalizing dropping funnel, nitrogen purge and heating mantle. The solution in the flask was heated to 40° C. 24.04 gm (0.240 mole) of 1,12-dodecanediamine was dissolved in 400 mL of 1:1 THF/toluene and slowly dropped into the stirred, heated solution of isocyanate. After addition of the diamine, an additional 100 mL of toluene was added to the flask. The temperature was raised to 80° C. and the reaction mixture was refluxed for 12 hours. 3-neck flask equipped with a thermometer, magnetic stirrer, pressure nitrogen purge heating mantle slowly dropped into the stirred The temperature was raised to 80° C. the reaction mixture was refluxed for 12 hours

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 30.04 gm (0.240 mole) of cyclohexyl isocyanate was dissolved in 400 mL of 1:1 THF/toluene in a 1000 mL round bottom, 3-neck flask equipped with a thermometer, magnetic stirrer, pressure equalizing dropping funnel, nitrogen purge and heating mantle. The solution in the flask was heated to 40° C. 24.04 gm (0.240 mole) of 1,12-dodecanediamine was dissolved in 400 mL of 1:1 THF/toluene and slowly dropped into the stirred, heated solution of isocyanate. After addition of the diamine, an additional 100 mL of toluene was added to the flask. The temperature was raised to 80° C. and the reaction mixture was refluxed for 12 hours. 3-neck flask equipped with a thermometer, magnetic stirrer, pressure nitrogen purge heating mantle slowly dropped into the stirred The temperature was raised to 80° C. the reaction mixture was refluxed for 12 hours

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

Procedure: Equimolar proportions of dodecamethylene diamine and naphthalene-2,7-dicarboxylic acid were dissolved in water, and then methanol was poured into the solution to form dodecamethylene diammonium naphthalene-2,7-dicarboxylate (12-N salt). The procedure of Examples 1 to 3 was repeated except that the 12-N salt was used instead of the 6-N salt, and hexamethylene diammonium monomethylterephthalate isophthalate (6-MTIA salt) was used instead of the 6-I salt. The properties of the resulting polyamides are shown in Table 8.