3-pentoxypropane-1,2-diol

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a four-necked 300-ml flask, 100 g (0.69 mole) of amyl glycidyl ether obtained in Example 1, 25 g (1.39 mole) of water, 2.31 g (0.028 mole) of 48% sodium hydroxide and 5.54 g (0.028 mole) of lauric acid were charged, followed by heating to 90° C. while stirring under a nitrogen gas atmosphere. The stirring was continued for 8 hours. After excess water was distilled off, the residue was distilled under reduced pressure (100° C., 0.133 kPa), whereby 110 g (0.59 mole) of amyl glyceryl ether was obtained (yield: 86%, purity: 99%). After excess water was distilled off the residue was distilled under reduced pressure (100° C., 0.133 kPa)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a four-necked 300-ml flask, 100 g (0.69 mole) of amyl glycidyl ether obtained in Example 1, 25 g (1.39 mole) of water, 2.31 g (0.028 mole) of 48% sodium hydroxide and 5.54 g (0.028 mole) of lauric acid were charged, followed by heating to 90° C. while stirring under a nitrogen gas atmosphere. The stirring was continued for 8 hours. After excess water was distilled off, the residue was distilled under reduced pressure (100° C., 0.133 kPa), whereby 110 g (0.59 mole) of amyl glyceryl ether was obtained (yield: 86%, purity: 99%). After excess water was distilled off the residue was distilled under reduced pressure (100° C., 0.133 kPa)

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

Procedure: A 3-neck, 2-liter round bottomed reaction flask (equipped with overhead stirrer, cold water condenser, mercury thermometer and addition funnel) are charged with about 546 g of aqueous NaOH (about 50% concentration) and about 38.5 g of tetrabutylammonium hydrogen sulfate (PTC, phase transfer catalyst). The content of the flask is stirred to achieve dissolution and then about 200 g of 1-pentanol is added along with about 400 ml hexanes (a mixture of isomers, with about 85% n-hexane). Into the addition funnel is charged about 418 g of epichlorohydrin which is slowly added (dropwise) to the stirring reaction mix. The temperature gradually rises to about 68° C. due to the reaction exotherm. The reaction is allowed to continue for about 1 hr after complete addition of the epichlorohydrin (no additional heat). dissolution a mixture of isomers is slowly added (dropwise) to the stirring reaction mix gradually rises to about 68° C. due to the reaction exotherm no additional heat)

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

Procedure: A 3-neck, 2-liter round bottomed reaction flask (equipped with overhead stirrer, cold water condenser, mercury thermometer and addition funnel) are charged with about 546 g of aqueous NaOH (about 50% concentration) and about 38.5 g of tetrabutylammonium hydrogen sulfate (PTC, phase transfer catalyst). The content of the flask is stirred to achieve dissolution and then about 200 g of 1-pentanol is added along with about 400 ml hexanes (a mixture of isomers, with about 85% n-hexane). Into the addition funnel is charged about 418 g of epichlorohydrin which is slowly added (dropwise) to the stirring reaction mix. The temperature gradually rises to about 68° C. due to the reaction exotherm. The reaction is allowed to continue for about 1 hr after complete addition of the epichlorohydrin (no additional heat). dissolution a mixture of isomers is slowly added (dropwise) to the stirring reaction mix gradually rises to about 68° C. due to the reaction exotherm no additional heat)

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

Procedure: A 3-neck, 2-liter round bottomed reaction flask (equipped with overhead stirrer, cold water condenser, mercury thermometer and addition funnel) are charged with about 546 g of aqueous NaOH (about 50% concentration) and about 38.5 g of tetrabutylammonium hydrogen sulfate (PTC, phase transfer catalyst). The content of the flask is stirred to achieve dissolution and then about 200 g of 1-pentanol is added along with about 400 ml hexanes (a mixture of isomers, with about 85% n-hexane). Into the addition funnel is charged about 418 g of epichlorohydrin which is slowly added (dropwise) to the stirring reaction mix. The temperature gradually rises to about 68° C. due to the reaction exotherm. The reaction is allowed to continue for about 1 hr after complete addition of the epichlorohydrin (no additional heat). dissolution a mixture of isomers is slowly added (dropwise) to the stirring reaction mix gradually rises to about 68° C. due to the reaction exotherm no additional heat)

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: n-Pentanol (132 g) and 8.1 g of ferric chloride were heated to 100° C. while stirring, followed by the dropwise addition of 92.5 g of epichlorohydrin over 1 hour. The reaction mixture was then heated to 115° C. and reacted for 5 hours. After the removal of an excess alcohol at 100° C. under reduced pressure (5.32 kPa), 6 g of lauric acid, 118 g of a 48% aqueous solution of potassium hydroxide and 162 g of water were added to the residue. The resulting mixture was reacted at 200° C. for 5 hours in an autoclave. The reaction mixture was neutralized with 2.3 g of a 48% aqueous solution of potassium hydroxide. The reaction mixture was dehydrated at 100° C. under reduced pressure (6.67 kPa) and the residue was purified by distillation under reduced pressure (133 to 266 Pa, 114 to 115° C.), whereby 102 g of monopentyl glyceryl ether was obtained. As a result of GLC, it was found to that the resulting compound had a purity not less than 99% and the content of organochlorine compounds was not greater than 100 ppm. reacted for 5 hours After the removal of an excess alcohol at 100° C. under reduced pressure (5.32 kPa), 6 g of lauric acid, 118 g of a 48% aqueous solution of potassium hydroxide and 162 g of water were added to the residue The resulting mixture was reacted at 200° C. for 5 hours in an autoclave was dehydrated at 100° C. under reduced pressure (6.67 kPa) the residue was purified by distillation under reduced pressure (133 to 266 Pa, 114 to 115° C.)

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

Procedure: In an autoclave, 163 g of the crude pentyl glycidyl ether, 108 g of water, 7.3 g of adipic acid and 10.4 g of sodium hydroxide were charged. The resulting mixture was heated to 200° C. while stirring. After stirring for 2 hours, 1.6 g of sodium hydroxide was added. The resulting reaction mixture was dehydrated at 100° C. under reduced pressure (5.32 kPa), followed by purification by distillation under reduced pressure (133 to 266 Pa, 114 to 115° C.) , whereby 117 g of monopentyl glyceryl ether was obtained. As a result of GLC, it was found that the resulting compound had a purity not less than 99% and the content of organochlorine compounds was not greater than 100 ppm. After stirring for 2 hours The resulting reaction mixture was dehydrated at 100° C. under reduced pressure (5.32 kPa) followed by purification by distillation under reduced pressure (133 to 266 Pa, 114 to 115° C.)

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

Procedure: In an autoclave, 163 g of the crude pentyl glycidyl ether, 108 g of water, 7.3 g of adipic acid and 10.4 g of sodium hydroxide were charged. The resulting mixture was heated to 200° C. while stirring. After stirring for 2 hours, 1.6 g of sodium hydroxide was added. The resulting reaction mixture was dehydrated at 100° C. under reduced pressure (5.32 kPa), followed by purification by distillation under reduced pressure (133 to 266 Pa, 114 to 115° C.) , whereby 117 g of monopentyl glyceryl ether was obtained. As a result of GLC, it was found that the resulting compound had a purity not less than 99% and the content of organochlorine compounds was not greater than 100 ppm. After stirring for 2 hours The resulting reaction mixture was dehydrated at 100° C. under reduced pressure (5.32 kPa) followed by purification by distillation under reduced pressure (133 to 266 Pa, 114 to 115° C.)

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

Procedure: A 3-neck, 2-liter round bottomed reaction flask (equipped with overhead stirrer, cold water condenser, mercury thermometer and addition funnel) are charged with about 546 g of aqueous NaOH (about 50% concentration) and about 38.5 g of tetrabutylammonium hydrogen sulfate (PTC, phase transfer catalyst). The content of the flask is stirred to achieve dissolution and then about 200 g of 1-pentanol is added along with about 400 ml hexanes (a mixture of isomers, with about 85% n-hexane). Into the addition funnel is charged about 418 g of epichlorohydrin which is slowly added (dropwise) to the stirring reaction mix. The temperature gradually rises to about 68° C. due to the reaction exotherm. The reaction is allowed to continue for about 1 hr after complete addition of the epichlorohydrin (no additional heat). dissolution a mixture of isomers is slowly added (dropwise) to the stirring reaction mix gradually rises to about 68° C. due to the reaction exotherm no additional heat)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a four-necked 300-ml flask, 100 g (0.69 mole) of amyl glycidyl ether obtained in Example 1, 25 g (1.39 mole) of water, 2.31 g (0.028 mole) of 48% sodium hydroxide and 5.54 g (0.028 mole) of lauric acid were charged, followed by heating to 90° C. while stirring under a nitrogen gas atmosphere. The stirring was continued for 8 hours. After excess water was distilled off, the residue was distilled under reduced pressure (100° C., 0.133 kPa), whereby 110 g (0.59 mole) of amyl glyceryl ether was obtained (yield: 86%, purity: 99%). After excess water was distilled off the residue was distilled under reduced pressure (100° C., 0.133 kPa)

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

Procedure: A 3-neck, 2-liter round bottomed reaction flask (equipped with overhead stirrer, cold water condenser, mercury thermometer and addition funnel) are charged with about 546 g of aqueous NaOH (about 50% concentration) and about 38.5 g of tetrabutylammonium hydrogen sulfate (PTC, phase transfer catalyst). The content of the flask is stirred to achieve dissolution and then about 200 g of 1-pentanol is added along with about 400 ml hexanes (a mixture of isomers, with about 85% n-hexane). Into the addition funnel is charged about 418 g of epichlorohydrin which is slowly added (dropwise) to the stirring reaction mix. The temperature gradually rises to about 68° C. due to the reaction exotherm. The reaction is allowed to continue for about 1 hr after complete addition of the epichlorohydrin (no additional heat). dissolution a mixture of isomers is slowly added (dropwise) to the stirring reaction mix gradually rises to about 68° C. due to the reaction exotherm no additional heat)

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

Procedure: A 3-neck, 2-liter round bottomed reaction flask (equipped with overhead stirrer, cold water condenser, mercury thermometer and addition funnel) are charged with about 546 g of aqueous NaOH (about 50% concentration) and about 38.5 g of tetrabutylammonium hydrogen sulfate (PTC, phase transfer catalyst). The content of the flask is stirred to achieve dissolution and then about 200 g of 1-pentanol is added along with about 400 ml hexanes (a mixture of isomers, with about 85% n-hexane). Into the addition funnel is charged about 418 g of epichlorohydrin which is slowly added (dropwise) to the stirring reaction mix. The temperature gradually rises to about 68° C. due to the reaction exotherm. The reaction is allowed to continue for about 1 hr after complete addition of the epichlorohydrin (no additional heat). dissolution a mixture of isomers is slowly added (dropwise) to the stirring reaction mix gradually rises to about 68° C. due to the reaction exotherm no additional heat)