2-dodecyloxirane

Conditions: temp:62.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Separately, a 500 ml mixing vessel equipped with a calcium chloride-containing tube was charged with 318.6 g (1.50 moles) of 1,2-epoxytetradecane. While the charged 1,2-epoxytetradecane was stirred and cooled with water, a concentrated sulfuric acid was gradually dropped in an amount of 2.7 g (0.027 mole) into the cooled 1,2-epoxytetradecane. After stirring for 15 minutes, the resultant mixture was placed into the dropping apparatus attached to the reaction vessel and was dropped into the 1,2-propanediol contained in the reaction vessel and maintained at a temperature of 60 to 65° C. over a time of 2 hours. Then the reaction of the mixture was carried out at a temperature of 60 to 65° C. for one hour. After the exhaustion of the starting material, namely 1,2-epoxytetradecane was confirmed by a thin-layer chromatography, the reaction was stopped. A powdered sodium hydrogen carbonate was mixed in an amount of 2.5 g (0.03 mole) into the resultant reaction liquid in the reaction vessel, the resultant mixture was stirred for 30 minutes to neutralize the reaction liquid. From the reaction liquid, the resultant precipitated crystals were separated by filtration. A 1,2-propanediol monohydroxydodecyl ether mixture was obtained in an amount of 432.0 g (yield: 97.3%). Separately, a 500 ml mixing vessel containing tube Then the reaction of the mixture was carried out at a temperature of 60 to 65° C. for one hour reaction liquid in the reaction vessel the reaction liquid From the reaction liquid the resultant precipitated crystals were separated by filtration

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The same reactor that was used in Production Example 5 was charged with 64 g (2 mol) of methanol and 2 g of boron trifluoride diethyl ether complex and then the mixture was raised to 60° C. Then, 212.3 g (1 mol) of 1,2-epoxytetradecane was added dropwise to the mixture over one hour and the resulting mixture was kept as it was for 3 hours. The reaction was terminated just after confirming that 1,2-epoxytetradecane left unreacted was less than 1% by gas chromatography and then the reaction mixture was cooled. Thereafter, methanol was removed in the same manner as in Production Example 5 to obtain 2-hydroxytetradecyl methyl ether. The reaction was terminated just left unreacted the reaction mixture was cooled Thereafter, methanol was removed in the same manner as in Production Example 5

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-tetradecene oxide (91.8 g.) and hexamethylenediamine (25 g.) and recrystallization of the resulting product (71 g., m.p. 118°-121° C.) from ethanol gave N,N'-(1,6-hexylene)-bis[2-hydroxytetradecylamine] (I: R= CH3 (CH2)11, R' = H, X== (CH2)6, Z= H) (55.3 g., m.p. 122°-126° C.).

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-tetradecene oxide (91.8 g.) and hexamethylenediamine (25 g.) and recrystallization of the resulting product (71 g., m.p. 118°-121° C.) from ethanol gave N,N'-(1,6-hexylene)-bis[2-hydroxytetradecylamine] (I: R= CH3 (CH2)11, R' = H, X== (CH2)6, Z= H) (55.3 g., m.p. 122°-126° C.).

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-tetradecene oxide (91.8 g.) and hexamethylenediamine (25 g.) and recrystallization of the resulting product (71 g., m.p. 118°-121° C.) from ethanol gave N,N'-(1,6-hexylene)-bis[2-hydroxytetradecylamine] (I: R= CH3 (CH2)11, R' = H, X== (CH2)6, Z= H) (55.3 g., m.p. 122°-126° C.).

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-tetradecene oxide (91.8 g.) and hexamethylenediamine (25 g.) and recrystallization of the resulting product (71 g., m.p. 118°-121° C.) from ethanol gave N,N'-(1,6-hexylene)-bis[2-hydroxytetradecylamine] (I: R = CH3 (CH2)11, R' = H, X = (CH2)6, Z = H) (55.3 g., m.p. 122°-126° C.).

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 15.0 g (0.035 mol) of the polyerythritol prepared in Example 1 and 0.15 g of sodium hydroxide were dissolved in 20 ml of N,N-dimethylformamide while heating at 150° C. in a dried nitrogen gas flow, and stirred for 30 minutes. 14.8 g (0.070 mol) of 1,2-epoxytetradecane in 50 ml of N,N-dimethylformamide was added to the mixture, which was further stirred for four hours at 105° C. in a dried nitrogen gas flow. After the reaction, N,N-dimetylformamide was evaporated to obtain adcrude product. After dissolving the crude product in 100 ml of hot toluene and cooling the solution to room temperature, unreacted polyerythritol was filtered out. The toluene in the filtrate was evaporated in vaccuo to obtain 28.5 g of a white powdery desired product. was further stirred for four hours at 105° C. in a dried nitrogen gas flow was evaporated to obtain adcrude product cooling the solution to room temperature unreacted polyerythritol was filtered out The toluene in the filtrate was evaporated in vaccuo

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-tetradecene oxide (91.8 g.) and hexamethylenediamine (25 g.) and recrystallization of the resulting product (71 g., m.p. 118°-121° C.) from ethanol gave N,N'-(1,6-hexylene)-bis[2-hydroxytetradecylamine] (I: R = CH3 (CH2)11, R' = H, X = (CH2)6, Z = H) (55.3 g., m.p. 122°-126° C.).

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a dry flask under argon was placed 10.2 g of 5-hexynoic acid, the product of lb, and 100 ml of HMPA (distilled over NaH). The solution was cooled to 0° C. and a solution of n-BuLi in hexane (115 ml, 0.185 mol) was added dropwise. After stirring for 1 hr., 21.7 g (0.118 mole) of dodecyl oxirane, the product of 1 c, was added dropwise. The reaction mixture was allowed to stir at room temperature for 3 days and then poured into 150 ml of ice and water. The aqueous solution was acidified with 5% HCl and then extracted with ether. The ether solution was washed with H2O, saturated with NaCl solution and then dried over MgSO4. Removal of solvent yielded crude product which was recrystallized in cyclohexane to give the title compound, mp 80.5°-81°. In a dry flask under argon was placed to stir at room temperature for 3 days extracted with ether The ether solution was washed with H2O, saturated with NaCl solution dried over MgSO4 Removal of solvent yielded crude product which was recrystallized in cyclohexane

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

Procedure: In a flask equipped with a mechanical stirrer and an addition funnel was placed 19.8 g (0.1 mole) of 1-tetradecene and 150 ml of CH2Cl2. The solution was stirred and a suspension of 23 g(0.106 mole) of m-chloroperbenzoic acid in 250 ml of CH2Cl2 was added dropwise. After stirring overnight, the CH2Cl2 solution was washed with 10% aqueous NaHSO3, saturated NaHCO3 solution and then dried over Na2SO4. The residue, after removal of solvent, was distilled through a vigreux column to obtain the title compound, bp 78°-81°/0.01 mmHg as a colorless liquid. In a flask equipped with a mechanical stirrer and an addition funnel was added dropwise After stirring overnight the CH2Cl2 solution was washed with 10% aqueous NaHSO3, saturated NaHCO3 solution dried over Na2SO4 The residue, after removal of solvent was distilled through a vigreux 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-tetradecene oxide (91.8 g.) and hexamethylenediamine (25 g.) and recrystallization of the resulting product (71 g., m.p. 118°-121° C.) from ethanol gave N,N'-(1,6-hexylene)-bis[2-hydroxytetradecylamine] (I: R = CH3 (CH2)11, R' = H, X = (CH2)6, Z = H) (55.3 g., m.p. 122°-126° C.).

Conditions: temp:62.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Separately, a 500 ml mixing vessel equipped with a calcium chloride-containing tube was charged with 318.6 g (1.50 moles) of 1,2-epoxytetradecane. While the charged 1,2-epoxytetradecane was stirred and cooled with water, a concentrated sulfuric acid was gradually dropped in an amount of 2.7 g (0.027 mole) into the cooled 1,2-epoxytetradecane. After stirring for 15 minutes, the resultant mixture was placed into the dropping apparatus attached to the reaction vessel and was dropped into the 1,2-propanediol contained in the reaction vessel and maintained at a temperature of 60 to 65° C. over a time of 2 hours. Then the reaction of the mixture was carried out at a temperature of 60 to 65° C. for one hour. After the exhaustion of the starting material, namely 1,2-epoxytetradecane was confirmed by a thin-layer chromatography, the reaction was stopped. A powdered sodium hydrogen carbonate was mixed in an amount of 2.5 g (0.03 mole) into the resultant reaction liquid in the reaction vessel, the resultant mixture was stirred for 30 minutes to neutralize the reaction liquid. From the reaction liquid, the resultant precipitated crystals were separated by filtration. A 1,2-propanediol monohydroxydodecyl ether mixture was obtained in an amount of 432.0 g (yield: 97.3%). Separately, a 500 ml mixing vessel containing tube Then the reaction of the mixture was carried out at a temperature of 60 to 65° C. for one hour reaction liquid in the reaction vessel the reaction liquid From the reaction liquid the resultant precipitated crystals were separated by filtration