2-propyl-1,3-dioxane

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

Procedure: 1000 g of 1,3-propanediol and 500 g of 2-propyl-1,3-dioxane were combined in a 2 L stainless steel autoclave with 6.0 g of 5% Pd on carbon catalyst. The reactor was sealed and purged twice with N2 and once with H2. The reactor was charged with H2 and heated to 200° C. The reactor was brought to an operating pressure of 6.89 MPa and stirring commenced at 750 rpm. Temperature and pressure were maintained for 2 h. The reactor was cooled, vented, and the contents filtered. The filtrate was analyzed by GC to yield 153 g of 2-propyl-1,3-dioxane, 288 g of 3-BP, 15.9 g of 1,3-dibutoxypropane, and 1017 g of 1,3-propanediol. This corresponds to yield 69% conversion of the acetal and 95% selectivity to the desired ether alcohol, 3-BP. The reactor was sealed purged twice with N2 and once with H2 The reactor was charged with H2 Temperature and pressure were maintained for 2 h The reactor was cooled the contents filtered

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

Procedure: This example illustrates the limitations of conventional synthesis methods. A 500 mL round bottom was charged with 191 g normal butyraldehyde, 101 g of 1,3-propanediol, and 4 drops 85% phosphoric acid. The round bottom was fitted with a Dean-Stark trap and condenser and the entire apparatus was placed into an electric heating mantle and brought to reflux. The aldehyde/water azeotrope condensed and separated into the trap. Heating was maintained until 24 mL of water had evolved (1 hr). The mixture was cooled and poured into a separatory funnel. The solution was washed twice with 50 mL of saturated sodium bicarbonate solution and once with 50 mL of distilled water. The organics were dried over MgSO4 and the residue distilled. A fraction collected at 150° C. was 99.6% acetal and had a mass of 95.7 g. This corresponds to a yield of 56%, lower than the yields reported in Table II. the limitations of conventional synthesis methods The round bottom was fitted with a Dean-Stark trap and condenser to reflux condensed separated into the trap Heating was maintained until 24 mL of water (1 hr) The mixture was cooled poured into a separatory funnel The solution was washed twice with 50 mL of saturated sodium bicarbonate solution and once with 50 mL of distilled water The organics were dried over MgSO4 the residue distilled A fraction collected at 150° C.

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

Procedure: Examples 5-7 were carried out using the apparatus described above. Prior to each example, the column was heated to 100° C. with boiling water as described above. Butyraldehyde was fed through the bottom feed plate and a mixture of 1,3-propanediol and 500 ppmw phosphoric acid was fed through the upper feed plate at rates described in Table II. A butyraldehyde/water azeotrope was condensed overhead at 73° C. The basepot reached a maximum temperature of 165° C. Material was removed from the basepot throughout the run. The material separated into two phases, each of which was analyzed by gas chromatography. The results are listed in Table II. condensed overhead at 73° C a maximum temperature of 165° C Material was removed from the basepot throughout the run The material separated into two phases

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

Procedure: Examples 5-7 were carried out using the apparatus described above. Prior to each example, the column was heated to 100° C. with boiling water as described above. Butyraldehyde was fed through the bottom feed plate and a mixture of 1,3-propanediol and 500 ppmw phosphoric acid was fed through the upper feed plate at rates described in Table II. A butyraldehyde/water azeotrope was condensed overhead at 73° C. The basepot reached a maximum temperature of 165° C. Material was removed from the basepot throughout the run. The material separated into two phases, each of which was analyzed by gas chromatography. The results are listed in Table II. condensed overhead at 73° C a maximum temperature of 165° C Material was removed from the basepot throughout the run The material separated into two phases

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

Procedure: This example illustrates the limitations of conventional synthesis methods. A 500 mL round bottom is charged with 191 g normal butyraldehyde, 101 g of 1,3-propanediol, and 4 drops 85% phosphoric acid. The round bottom is fitted with a Dean-Stark trap and condenser and the entire apparatus is placed into an electric heating mantle and brought to reflux. The aldehyde/water azeotrope condenses and separates into the trap. Heating is maintained until 24 mL of water has evolved (1 hr). The mixture is cooled and poured into a separatory funnel. The solution is washed twice with 50 mL of saturated sodium bicarbonate solution and once with 50 mL of distilled water. The organics are dried over MgSO4 and the residue distilled. A fraction collected at 150° C. is 99.6% acetal and has a mass of 95.7 g. This corresponds to a yield of 56%, lower than the yields reported in Table II. the limitations of conventional synthesis methods The round bottom is fitted with a Dean-Stark trap and condenser to reflux Heating (1 hr) The mixture is cooled poured into a separatory funnel The solution is washed twice with 50 mL of saturated sodium bicarbonate solution and once with 50 mL of distilled water The organics are dried over MgSO4 the residue distilled A fraction collected at 150° C.

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

Procedure: Examples 5-7 are carried out using the apparatus described above. Prior to each example, the column is heated to 100° C. with boiling water as described above. Butyraldehyde is fed through the bottom feed plate and a mixture of 1,3-propanediol and 500 ppmw phosphoric acid is fed through the upper feed plate at rates described in Table I. A butyraldehyde/water azeotrope is condensed overhead at 73° C. The basepot reaches a maximum temperature of 165° C. Material is removed from the basepot throughout the run. The material separates into two phases, each of which is analyzed by gas chromatography. The results are listed in Table II. condensed overhead at 73° C a maximum temperature of 165° C Material is removed from the basepot throughout the run

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

Procedure: 1000 g of 1,3-propanediol and 500 g of 2-propyl-1,3-dioxane were combined in a 2 L stainless steel autoclave with 6.0 g of 5% Pd on carbon catalyst. The reactor was sealed and purged twice with N2 and once with H2. The reactor was charged with H2 and heated to 200° C. The reactor was brought to an operating pressure of 6.89 MPa and stirring commenced at 750 rpm. Temperature and pressure were maintained for 2 h. The reactor was cooled, vented, and the contents filtered. The filtrate was analyzed by GC to yield 153 g of 2-propyl-1,3-dioxane, 288 g of 3-BP, 15.9 g of 1,3-dibutoxypropane, and 1017 g of 1,3-propanediol. This corresponds to yield 69% conversion of the acetal and 95% selectivity to the desired ether alcohol, 3-BP. The reactor was sealed purged twice with N2 and once with H2 The reactor was charged with H2 Temperature and pressure were maintained for 2 h The reactor was cooled the contents filtered

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

Procedure: This example illustrates the limitations of conventional synthesis methods. A 500 mL round bottom was charged with 191 g normal butyraldehyde, 101 g of 1,3-propanediol, and 4 drops 85% phosphoric acid. The round bottom was fitted with a Dean-Stark trap and condenser and the entire apparatus was placed into an electric heating mantle and brought to reflux. The aldehyde/water azeotrope condensed and separated into the trap. Heating was maintained until 24 mL of water had evolved (1 hr). The mixture was cooled and poured into a separatory funnel. The solution was washed twice with 50 mL of saturated sodium bicarbonate solution and once with 50 mL of distilled water. The organics were dried over MgSO4 and the residue distilled. A fraction collected at 150° C. was 99.6% acetal and had a mass of 95.7 g. This corresponds to a yield of 56%, lower than the yields reported in Table II. the limitations of conventional synthesis methods The round bottom was fitted with a Dean-Stark trap and condenser to reflux condensed separated into the trap Heating was maintained until 24 mL of water (1 hr) The mixture was cooled poured into a separatory funnel The solution was washed twice with 50 mL of saturated sodium bicarbonate solution and once with 50 mL of distilled water The organics were dried over MgSO4 the residue distilled A fraction collected at 150° C.

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

Procedure: Examples 5-7 were carried out using the apparatus described above. Prior to each example, the column was heated to 100° C. with boiling water as described above. Butyraldehyde was fed through the bottom feed plate and a mixture of 1,3-propanediol and 500 ppmw phosphoric acid was fed through the upper feed plate at rates described in Table II. A butyraldehyde/water azeotrope was condensed overhead at 73° C. The basepot reached a maximum temperature of 165° C. Material was removed from the basepot throughout the run. The material separated into two phases, each of which was analyzed by gas chromatography. The results are listed in Table II. condensed overhead at 73° C a maximum temperature of 165° C Material was removed from the basepot throughout the run The material separated into two phases