3-octoxypropane-1,2-diol

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

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

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

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

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a reactor, 390 g of octanol, 2 g of aluminum triisopropoxide and 1.4 g of sulfuric acid were charged. After heating to 100° C., dehydration was conducted under reduced pressure (2.67 kPa). The residue was then cooled to 85° C., followed by the dropwise addition of 185 g of epichlorohydrin at a temperature maintained at 85° C. After stirring at 85° C. for 4 hours, an excess alcohol was removed at 100° C. under reduced pressure (0.67 kPa). To the crude octyl halohydrin ether thus obtained, 480 g of a 209 aqueous solution of sodium hydroxide was added and the resulting mixture was reacted at 90° C. for 2 hours. After completion of the reaction, the water layer was removed, whereby 315 g of crude octyl glycidyl ether was obtained. In an autoclave, 200 g of the resulting crude octyl glycidyl ether, 35 g of water, 11.8 g of 99% acetic acid and 12.1 g of a 48% aqueous solution of sodium hydroxide were charged, followed by stirring at 200° C. for 1 hour. At a temperature maintained at 200° C., 27.5 g of a 48% aqueous solution of sodium hydroxide was added dropwise over 3 hours and reaction was conducted for 1 hour. The reaction mixture was cooled to 80° C. While maintaining the temperature at 80° C., 150 g of water was added and the resulting mixture was stirred vigorously. The reaction mixture was allowed to stand to cause separation, followed by removal of the water layer. The operation from the addition of 150 g of water to the separation was then repeated three times. The reaction mixture was dehydrated at 100° C. under reduced pressure (5.32 kPa), whereby 224 g of monooctyl glyceryl ether was obtained. As a result of GLC, it was found that the resulting product had a purity of 91% and the content of organochlorine compounds was not greater than 100 ppm. At a temperature maintained at 200° C. reaction was conducted for 1 hour The reaction mixture was cooled to 80° C While maintaining the temperature at 80° C. the resulting mixture was stirred vigorously separation followed by removal of the water layer The operation from the addition of 150 g of water to the separation was dehydrated at 100° C. under reduced pressure (5.32 kPa)

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In an autoclave, 208 g of the resulting crude octyl glycidyl ether, 104.8 g of water, 5.82 g of lauric acid and 18.5 g of potassium hydroxide were charged. The resulting mixture was stirred at 140° C. for 5 hours. The reaction mixture was dehydrated at 100° C. under reduced pressure (6.67 kPa), followed by the addition of 9.7 g of lauric acid and 2.72 g of potassium hydroxide. After reaction at 160° C. for 15 hours, the reaction mixture was purified by distillation under reduced pressure (53 to 67 Pa, 120 to 123° C.), whereby 110.2 g of monooctyl glyceryl ether was obtained. As a result of GLC, it was found that the resulting product had a purity not less than 99% and the content of organochlorine compounds was not greater than 100 ppm. was dehydrated at 100° C. under reduced pressure (6.67 kPa) After reaction at 160° C. for 15 hours the reaction mixture was purified by distillation under reduced pressure (53 to 67 Pa, 120 to 123° C.)

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In an autoclave, 208 g of the resulting crude octyl glycidyl ether, 104.8 g of water, 5.82 g of lauric acid and 18.5 g of potassium hydroxide were charged. The resulting mixture was stirred at 140° C. for 5 hours. The reaction mixture was dehydrated at 100° C. under reduced pressure (6.67 kPa), followed by the addition of 9.7 g of lauric acid and 2.72 g of potassium hydroxide. After reaction at 160° C. for 15 hours, the reaction mixture was purified by distillation under reduced pressure (53 to 67 Pa, 120 to 123° C.), whereby 110.2 g of monooctyl glyceryl ether was obtained. As a result of GLC, it was found that the resulting product had a purity not less than 99% and the content of organochlorine compounds was not greater than 100 ppm. was dehydrated at 100° C. under reduced pressure (6.67 kPa) After reaction at 160° C. for 15 hours the reaction mixture was purified by distillation under reduced pressure (53 to 67 Pa, 120 to 123° C.)

Conditions: temp:47.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 500-mL autoclave were added 100 g of the resulting octadienyl glyceryl ether and 5 g of 5% Pd—C (product of NE Chemcat Corporation). The mixture was stirred at 25 to 70° C. for 6 hours under a hydrogen atmosphere of 1 to 5 MPa. After completion of the reaction, the catalyst was filtered away, whereby 102 g of octyl glyceryl ether was obtained as a colorless transparent oil. GC analysis of the resulting oil showed that the content of monooctyl glyceryl ether was 99%, while that of dioctyl glyceryl ether was 1% or less. After completion of the reaction the catalyst was filtered away

Conditions: temp:47.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 500-mL autoclave were added 100 g of the resulting octadienyl glyceryl ether and 5 g of 5% Pd—C (product of NE Chemcat Corporation). The mixture was stirred at 25 to 70° C. for 6 hours under a hydrogen atmosphere of a pressure of 1 to 5 MPa. After completion of the reaction, the catalyst was filtered off, whereby 102 g of octyl glyceryl ether was obtained as a colorless transparent oil. Gas chromatography(GC) analysis showed that the monooctyl glyceryl ether content was 99%, and the dioctyl glyceryl ether content was 1% or less. After completion of the reaction the catalyst was filtered off

Conditions: temp:157.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The crude octyl glycidyl ether (175 g), water (110 g; 6.111 mol), lauric acid (7.10 g; 0.033 mol) and sodium hydroxide (0.71 g; 0.018 mol) were placed in a 2-l autoclave, and the mixture was heated up to 157° C. while stirring it. The mixture was stirred for 5 hours as it was, and was then allowed to cool down to room temperature. The mixture was extracted with ethyl acetate (500 ml), and the extract was washed twice with water (300 ml). The solvent was then distilled off to obtain 165 g of crude monooctyl glyceryl ether. This crude product was purified by vacuum distillation (0.4-0.5 mmHg, 120-123° C.) to obtain 124 g of monooctyl glyceryl ether as a colorless transparent oil (total yield: 75%). Quenching of a proton signal (methylene in an epoxy ring) at δ=2.65, 2.80 was observed by 1H-NMR (200 MHz), thereby identifying the compound. The purity of the compound was found to be 99% by GLC. The mixture was stirred for 5 hours as it to cool down to room temperature The mixture was extracted with ethyl acetate (500 ml) the extract was washed twice with water (300 ml) The solvent was then distilled off

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