octadecane-1,2-diol

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Approximately 360 g of the 1,2-mixed pentadecanedioloctadecanediol (obtained from Viking Chemical Co. as Vikol 158 containing about 28% 1,2-pentadecanediol, about 28% 1,2-hexadecanediol, about 28% 1,2-heptadecanediol and about 16% 1,2-octadecanediol) were charged to a glass reactor equipped with heater, agitator, Dean-Stark tube with condenser and provision for blanketing the vapor space with nitrogen. The contents were heated to 70° C. to liquify and 55 g of dimethyl hydrogen phosphite were slowly added. The reaction mixture was heated to 110° C. and held for 2 hours, held at 120° C. for 1 hour, and held at 130° C. for 1 hour. During this reaction period, methanol distilled over and condensed into the trap. The crude product was vacuum stripped at 150° C. to remove volatile materials. 379 g of finished additive were produced. The product was an amber fluid which became waxy on cooling. equipped with heater, agitator, Dean-Stark tube with condenser The reaction mixture was heated to 110° C. held at 120° C. for 1 hour held at 130° C. for 1 hour distilled over and condensed into the trap stripped at 150° C. to remove volatile materials 379 g of finished additive were produced on cooling

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Approximately 360 g of the 1,2-mixed pentadecanedioloctadecanediol (obtained from Viking Chemical Co. as Vikol 158 containing about 28% 1,2-pentadecanediol, about 28% 1,2-hexadecanediol, about 28% 1,2-heptadecanediol and about 16% 1,2-octadecanediol) were charged to a glass reactor equipped with heater, agitator, Dean-Stark tube with condenser and provision for blanketing the vapor space with nitrogen. The contents were heated to 70° C. to liquify and 55 g of dimethyl hydrogen phosphite were slowly added. The reaction mixture was heated to 110° C. and held for 2 hours, held at 120° C. for 1 hour, and held at 130° C. for 1 hour. During this reaction period, methanol distilled over and condensed into the trap. The crude product was vacuum stripped at 150° C. to remove volatile materials. 379 g of finished additive were produced. The product was an amber fluid which became waxy on cooling. equipped with heater, agitator, Dean-Stark tube with condenser The reaction mixture was heated to 110° C. held at 120° C. for 1 hour held at 130° C. for 1 hour distilled over and condensed into the trap stripped at 150° C. to remove volatile materials 379 g of finished additive were produced on cooling

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Approximately 360 g of the 1,2-mixed pentadecanedioloctadecanediol (obtained from Viking Chemical Co. as Vikol 158 containing about 28% 1,2-pentadecanediol, about 28% 1,2-hexadecanediol, about 28% 1,2-heptadecanediol and about 16% 1,2-octadecanediol) were charged to a glass reactor equipped with heater, agitator, Dean-Stark tube with condenser and provision for blanketing the vapor space with nitrogen. The contents were heated to 70° C. to liquify and 55 g of dimethyl hydrogen phosphite were slowly added. The reaction mixture was heated to 110° C. and held for 2 hours, held at 120° C. for 1 hour, and held at 130° C. for 1 hour. During this reaction period, methanol distilled over and condensed into the trap. The crude product was vacuum stripped at 150° C. to remove volatile materials. 379 g of finished additive were produced. The product was an amber fluid which became waxy on cooling. equipped with heater, agitator, Dean-Stark tube with condenser The reaction mixture was heated to 110° C. held at 120° C. for 1 hour held at 130° C. for 1 hour distilled over and condensed into the trap stripped at 150° C. to remove volatile materials 379 g of finished additive were produced on cooling

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

Procedure: A 1-liter flask equipped with a stirrer and dropping funnel was charged with 20 g (70 mmol) of octadecane-1,2-diol, 0.7 g (3.5 mmol) of p-toluenesulfonic acid and 350 ml of dichloromethane. While stirring the contents at room temperature, 5.9 g (70 mmol) of dihydropyran were added dropwise. After stirring the mixture at room temperature for 30 minutes, it was neutralized with NaHCO3 and concentrated under reduced pressure, and the resultant residue was then purified by column chromatography on silica gel, thereby obtaining 7.5 g (yield[: 29%) of 1-(2-tetrahydropyranyloxy)-2-octadecanol. This compound was charged into a 200-ml flask equipped with a stirrer, to which 5.1 g (50 mmol) of triethylamine and 50 ml of dichloromethane were added. Further, 3.8 g (33 mmol) of methanesulfonyl chloride were added at room temperature with stirring. After the resultant mixture was stirred at room temperature for 14 hours, the reaction mixture was added with water and subjected to extraction with dichloromethane, and the solvent was distilled off under reduced pressure. The resultant residue and 15 ml of dimethylformamide was charged into a 100-ml flask equipped with a stirrer, to which 5.5 g (83 mmol) of NaN3 were added. The contents were stirred at 90° C. for 1.5 hours. After cooling the reaction mixture to room temperature, it was added with water and subjected to extraction with chloroform, followed by concentration under reduced pressure. Thereafter, the resultant residue was purified by column chromatography on silica gel, thereby obtaining 7.1 g (yield: 90%) of an azide intermediate. A 1-liter flask equipped with a stirrer After stirring the mixture at room temperature for 30 minutes concentrated under reduced pressure the resultant residue was then purified by column chromatography on silica gel

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

Procedure: A 1-liter flask equipped with a stirrer and dropping funnel was charged with 20 g (70 mmol) of octadecane-1,2-diol, 0.7 g (3.5 mmol) of p-toluenesulfonic acid and 350 ml of dichloromethane. While stirring the contents at room temperature, 5.9 g (70 mmol) of dihydropyran were added dropwise. After stirring the mixture at room temperature for 30 minutes, it was neutralized with NaHCO3 and concentrated under reduced pressure, and the resultant residue was then purified by column chromatography on silica gel, thereby obtaining 7.5 g (yield[: 29%) of 1-(2-tetrahydropyranyloxy)-2-octadecanol. This compound was charged into a 200-ml flask equipped with a stirrer, to which 5.1 g (50 mmol) of triethylamine and 50 ml of dichloromethane were added. Further, 3.8 g (33 mmol) of methanesulfonyl chloride were added at room temperature with stirring. After the resultant mixture was stirred at room temperature for 14 hours, the reaction mixture was added with water and subjected to extraction with dichloromethane, and the solvent was distilled off under reduced pressure. The resultant residue and 15 ml of dimethylformamide was charged into a 100-ml flask equipped with a stirrer, to which 5.5 g (83 mmol) of NaN3 were added. The contents were stirred at 90° C. for 1.5 hours. After cooling the reaction mixture to room temperature, it was added with water and subjected to extraction with chloroform, followed by concentration under reduced pressure. Thereafter, the resultant residue was purified by column chromatography on silica gel, thereby obtaining 7.1 g (yield: 90%) of an azide intermediate. A 1-liter flask equipped with a stirrer After stirring the mixture at room temperature for 30 minutes concentrated under reduced pressure the resultant residue was then purified by column chromatography on silica gel

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Approximately 360 g of the 1,2-mixed pentadecanedioloctadecanediol (obtained from Viking Chemical Co. as Vikol 158 containing about 28% 1,2-pentadecanediol, about 28% 1,2-hexadecanediol, about 28% 1,2-heptadecanediol and about 16% 1,2-octadecanediol) were charged to a glass reactor equipped with heater, agitator, Dean-Stark tube with condenser and provision for blanketing the vapor space with nitrogen. The contents were heated to 70° C. to liquify and 55 g of dimethyl hydrogen phosphite were slowly added. The reaction mixture was heated to 110° C. and held for 2 hours, held at 120° C. for 1 hour, and held at 130° C. for 1 hour. During this reaction period, methanol distilled over and condensed into the trap. The crude product was vacuum stripped at 150° C. to remove volatile materials. 379 g of finished additive were produced. The product was an amber fluid which became waxy on cooling. equipped with heater, agitator, Dean-Stark tube with condenser The reaction mixture was heated to 110° C. held at 120° C. for 1 hour held at 130° C. for 1 hour distilled over and condensed into the trap stripped at 150° C. to remove volatile materials 379 g of finished additive were produced on cooling

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

Procedure: A 1-liter flask equipped with a stirrer and dropping funnel was charged with 20 g (70 mmol) of octadecane-1,2-diol, 0.7 g (3.5 mmol) of p-toluenesulfonic acid and 350 ml of dichloromethane. While stirring the contents at room temperature, 5.9 g (70 mmol) of dihydropyran were added dropwise. After stirring the mixture at room temperature for 30 minutes, it was neutralized with NaHCO3 and concentrated under reduced pressure, and the resultant residue was then purified by column chromatography on silica gel, thereby obtaining 7.5 g (yield[: 29%) of 1-(2-tetrahydropyranyloxy)-2-octadecanol. This compound was charged into a 200-ml flask equipped with a stirrer, to which 5.1 g (50 mmol) of triethylamine and 50 ml of dichloromethane were added. Further, 3.8 g (33 mmol) of methanesulfonyl chloride were added at room temperature with stirring. After the resultant mixture was stirred at room temperature for 14 hours, the reaction mixture was added with water and subjected to extraction with dichloromethane, and the solvent was distilled off under reduced pressure. The resultant residue and 15 ml of dimethylformamide was charged into a 100-ml flask equipped with a stirrer, to which 5.5 g (83 mmol) of NaN3 were added. The contents were stirred at 90° C. for 1.5 hours. After cooling the reaction mixture to room temperature, it was added with water and subjected to extraction with chloroform, followed by concentration under reduced pressure. Thereafter, the resultant residue was purified by column chromatography on silica gel, thereby obtaining 7.1 g (yield: 90%) of an azide intermediate. A 1-liter flask equipped with a stirrer After stirring the mixture at room temperature for 30 minutes concentrated under reduced pressure the resultant residue was then purified by column chromatography on silica gel