decane-1,10-diamine

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

Procedure: Chloromethanephosphonic acid (5.5 g, 42 mmoles) and 1.10-diaminodecane (44 g, 255 mmoles) were heated under reflux in water (200 cm3) for 20 hours. The water was removed and ethanol (400 cm3) added to the solid residue. The phosphonic acid was filtered off and dried. The crude yield was 11.4 g (87%). A sample was purified by recrystallization from water/ethanol to give N-(10-aminodecyl)-aminomethanephosphonic acid monohydrate as a fine white crystalline solid having a melting point of 238° C. The water was removed ethanol (400 cm3) added to the solid residue The phosphonic acid was filtered off dried A sample was purified by recrystallization from water/ethanol

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

Procedure: Chloromethanephosphonic acid (5.5 g, 42 mmoles) and 1.10-diaminodecane (44 g, 255 mmoles) were heated under reflux in water (200 cm3) for 20 hours. The water was removed and ethanol (400 cm3) added to the solid residue. The phosphonic acid was filtered off and dried. The crude yield was 11.4 g (87%). A sample was purified by recrystallization from water/ethanol to give N-(10-aminodecyl)-aminomethanephosphonic acid monohydrate as a fine white crystalline solid having a melting point of 238° C. The water was removed ethanol (400 cm3) added to the solid residue The phosphonic acid was filtered off dried A sample was purified by recrystallization from water/ethanol

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a dry 1000-mL, three-necked round-bottom flask equipped with an overhead stirrer and a dropping funnel were placed 8.6 g (0.05 mol) of 1,10-diaminodecane, 34 g (0.33 mol) of triethylamine and 200 mL of acetone (Aldrich acetone HPLC≧99.9%). The mixture was cooled to 15° C. in an ice bath under nitrogen and a total of 27 g (0.3 mol) of acryloyl chloride (97% Aldrich) was added dropwise with constant stirring over a period of 1 hour. The reaction was monitored with an internal temperature probe. When the addition was complete, the reaction was allowed to warm to ambient temperature and was stirred overnight. The reaction was terminated by the addition of 1 equivalent of water to the acryloyl chloride and allowed to stir for 30 minutes. The triethylamine hydrochloride salt was removed by passing the reaction solution through a filter. The reaction mixture was concentrated under reduced pressure and washed with 5% sodium bicarbonate, bubble evolved and a precipitate resulted. The white precipitate was washed with an excess of water and diethyl ether. The white precipitate was dissolved in a small amount of methanol and the product was precipitated again into water. The white precipitate was washed with diethyl ether and then dried under vacuum. The resulting powder was further purified by column chromatography over silica (dichloromethane/methanol, 9:1 v/v). The resulting yields were in the range of 50-70%. 1H NMR (CD3OD, 25° C., δ ppm, [6.2, 5.6, Olefin], [3.2-3.4 br-CH2-acrylamide, 1.6 br, 1.3 br-alkane]. MS m/e (MH+), calcd 280.22. found 281.3. A similar synthesis procedure can be used to make other N,N′-(Cmalkane-1,m-diyl)diacrylamides. Into a dry 1000-mL, three-necked round-bottom flask equipped with an overhead stirrer and a dropping funnel When the addition to warm to ambient temperature was stirred overnight to stir for 30 minutes The triethylamine hydrochloride salt was removed The reaction mixture was concentrated under reduced pressure washed with 5% sodium bicarbonate bubble a precipitate resulted The white precipitate was washed with an excess of water and diethyl ether The white precipitate was dissolved in a small amount of methanol the product was precipitated again into water The white precipitate was washed with diethyl ether dried under vacuum The resulting powder was further purified by column chromatography over silica (dichloromethane/methanol, 9:1 v/v) The resulting yields A similar synthesis procedure

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

Procedure: Next, in the mixing section 22, the vapor atmosphere of 1,10-diaminodecane was cooled, and the introduced base particles were exposed thereto for 5 minutes. Consequently, a polymerization reaction took place on the surface of the base particles between 1,4-butanedisulfonyl chloride and 1,10-diaminodecane, forming a film of 1,4-butanedisulfonylchloride-1,10-diaminodecane co-polymer. Consequently, a polymerization reaction

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

Procedure: Next, in the mixing section 22, the vapor atmosphere of 1,10-diaminodecane was cooled, and the introduced base particles were exposed thereto for 5 minutes. Consequently, a polymerization reaction took place on the surface of the base particles between 1,4-butanedisulfonyl chloride and 1,10-diaminodecane, forming a film of 1,4-butanedisulfonylchloride-1,10-diaminodecane co-polymer. Consequently, a polymerization reaction

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

Procedure: In a manner similar to that of Example 1, condensation of 1-hexene oxide (34.8 g.) and 1,10-decanediamine (30 g.) and recrystallization of the resulting product from isopropyl alcohol gave N,N'-(1,10-decylene)-bis[2-hydroxyhexylamine] (I: R= CH3 (CH2)3R' = H, X= (CH2)10, Z= H) (8.9 g., m.p. 127.0°-137.0° C.).

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

Procedure: 1,10-diaminodecane (6.88 g, 40 mmol) were dissolved in 100 ml of ethanol and 3.22 ml of ethylformate was added. The reaction mixture was stirred at room temperature under a nitrogen atmosphere for 18 hours and evaporated to dryness. The residue was chromatographed on a silica gel column using 25% methanol/methylenechloride as the eluent to obtain 4 g of the title product. evaporated to dryness The residue was chromatographed on a silica gel column

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

Procedure: 1,10-diaminodecane (6.88 g, 40 mmol) were dissolved in 100 ml of ethanol and 3.22 ml of ethylformate was added. The reaction mixture was stirred at room temperature under a nitrogen atmosphere for 18 hours and evaporated to dryness. The residue was chromatographed on a silica gel column using 25% methanol/methylenechloride as the eluent to obtain 4 g of the title product. evaporated to dryness The residue was chromatographed on a silica gel column

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

Procedure: In a manner similar to that of Example 1, condensation of 1-hexene oxide (34.8 g.) and 1,10-decanediamine (30 g.) and recrystallization of the resulting product from isopropyl alcohol gave N,N'-(1,10-decylene)-bis[2-hydroxyhexylamine] (I: R = CH3 (CH2)3, R' = H, X = (CH2)10, Z = H) (8.9 g., m.p. 127.0-137.0° C.).

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

Procedure: PA612 is prepared in a known manner by polycondensation of an equivalent mixture of hexamethylenediamine and 1,12-dodecanedioic acid. PA1012 is prepared by polycondensation of an equivalent mixture of 1,10-decanediamine and 1,12-dodecanedioic acid, while PA1212 is obtained in the same manner from 1,12-dodecanediamine and 1,12-dodecanedioic acid.

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

Procedure: In a 500 ml flask protected with a soda lime tube is placed 10 g (0.058 mole) 1,10-diamino decane and 150 ml ether. A solution of 2.5 g (0.025 mole)n-butyl isocyanate in 25 ml ether is added and the reaction mixture stirred 1 hour. The precipitate is filtered, washed with ether, and dried to 15 g weight. Recrystallization from a mixture of 200 ml alcohol and 100 ml water gives 5.6 g white solids. An analytical sample recrystallized from acetonitrile melts at 83°-84.5°C. In a 500 ml flask protected with a soda lime tube The precipitate is filtered washed with ether dried to 15 g weight Recrystallization from a mixture of 200 ml alcohol and 100 ml water

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

Procedure: In a manner similar to that of Example 1, condensation of 1-hexene oxide (34.8 g.) and 1,10-decanediamine (30 g.) and recrystallization of the resulting product from isopropyl alcohol gave N,N'-(1,10-decylene)-bis[2-hydroxyhexylamine] (I: R = CH3 (CH2)3, R' = H, X = (CH2)10, Z = H) (8.9 g., m.p. 127.0°-137.0° C.).