2-(dibutylamino)ethanol

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

Procedure: N,N-Dibutylaminoethyl Tributylstannyl Ether is prepared from 59.6 gm (0.1 mole) bis(tributyltin) oxide and 34.6 gm (0.2 mole) N,N-dibutylethanolamine in 200 ml benzene. This is stirred and heated to reflux in a system that contains a Dean-Starke tube. After 30 minutes water began to collect in the Dean-Starke tube and after refluxing for a period of 22 hours a total of 1.8 ml of water (theory 1.8 ml) had collected. A rotating evaporator is used to remove the benzene and to provide 95.1 gm of red-orange liquid. This is fractionated at reduced pressure with collection at 163°-166° C. at 0.7 mm of 73.1 gm of yellow liquid (Percent yield - 79). Infrared spectral analysis shows this to be the desired ether. heated to reflux in a system that to collect in the Dean-Starke tube after refluxing for a period of 22 hours a total of 1.8 ml of water (theory 1.8 ml) had collected A rotating evaporator to remove the benzene

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

Procedure: N,N-Dibutylaminoethyl Tributylstannyl Ether is prepared from 59.6 gm (0.1 mole) bis(tributyltin) oxide and 34.6 gm (0.2 mole) N,N-dibutylethanolamine in 200 ml benzene. This is stirred and heated to reflux in a system that contains a Dean-Starke tube. After 30 minutes water began to collect in the Dean-Starke tube and after refluxing for a period of 22 hours a total of 1.8 ml of water (theory 1.8 ml) had collected. A rotating evaporator is used to remove the benzene and to provide 95.1 gm of red-orange liquid. This is fractionated at reduced pressure with collection at 163°-166° C. at 0.7 mm of 73.1 gm of yellow liquid (Percent yield - 79). Infrared spectral analysis shows this to be the desired ether. heated to reflux in a system that to collect in the Dean-Starke tube after refluxing for a period of 22 hours a total of 1.8 ml of water (theory 1.8 ml) had collected A rotating evaporator to remove the benzene

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 500 mL round bottomed flask fitted with a magnetic stirrer, heating mantle, and distillation head was charged with a mixture of methyl methacrylate (100 g, 1.0 mol, available from TCI), 2-dibutylaminoethanol (43.3 g, 0.25 mol, available from Matheson, Coleman and Bell, Norwood, Ohio), aluminum isopropoxide (5.0 g, 24 mmol, available form Alfa Aesar), and N-phenyl-1-naphthylamine (2.5 g, 11 mmol, available from Aldrich). The mixture was stirred and heated at 80° C. for one hour. The temperature of the reaction mixture was increased 10° C. per hour until a temperature of 110° C. was reached. By this time about 20 mL of material (methanol and methyl methacrylate) had distilled over from the reaction flask. The reaction mixture was left at room temperature overnight. The next day, the reaction mixture was heated at 115° C. for 2 hours and then heated at 135° C. as material distilled from the reaction flask. After 1 hour at 135° C., the desired product, di(butylamino)ethyl methacrylate, was distilled from the reaction flask at reduced pressure and collected at a temperature of 113-118° C. at 2.5 mm pressure. NMR spectral analyses confirmed the structure of the product. The boiling point reported previously for this methacrylate (U.S. Pat. No. 2,138,763 (DuPont)) is 108-109° C. at 2 mm pressure. A 500 mL round bottomed flask fitted with a magnetic stirrer heating mantle distillation head The temperature of the reaction mixture was increased 10° C. per hour until a temperature of 110° C. By this time about 20 mL of material (methanol and methyl methacrylate) had distilled over from the reaction flask The next day, the reaction mixture was heated at 115° C. for 2 hours heated at 135° C. as material distilled from the reaction flask After 1 hour at 135° C. the desired product, di(butylamino)ethyl methacrylate, was distilled from the reaction flask at reduced pressure collected at a temperature of 113-118° C. at 2.5 mm pressure is 108-109° C. at 2 mm pressure

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

Procedure: N,N-dibutylethanolamine/triethylene glycol monobutyl ether borate was prepared as follows. Boric acid (10.3 grams), triethylene glycol monobutyl ether (Fluka, 64.1 grams), and N,N-dibutylethanolamine (28.9 grams) were added to a 250 milliliter flask. One hundred fifty milliliters of toluene was then added. The reaction was allowed to proceed overnight at 110° C., and the byproduct water (˜9 grams) was continuously removed from the reaction by azeotropic distillation. The final solution was evaporated to remove toluene under vacuum, and a brownish liquid product (˜90 grams) of N,N-dibutylethanolamine/triethylene glycol monobutyl ether borate was obtained. N,N-dibutylethanolamine/triethylene glycol monobutyl ether borate was prepared the byproduct water (˜9 grams) was continuously removed from the reaction by azeotropic distillation The final solution was evaporated to remove toluene under vacuum

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

Procedure: N,N-dibutylethanolamine sorbitol borate was prepared as follows. Boric acid (10.3 grams), sorbitol (30.4 grams), and N,N-dibutylethanolamine (28.9 grams) were added to a 250 milliliter flask. One hundred fifty milliliters of toluene was then added. The reaction was allowed to proceed overnight at 110° C., and the byproduct water (˜9 grams) was continuously removed from the reaction by azeotropic distillation. The final solution was evaporated to remove toluene under vacuum, and a yellowish resinous product (˜60 grams) of N,N-dibutylethanolamine/sorbitol borate was obtained. N,N-dibutylethanolamine sorbitol borate was prepared the byproduct water (˜9 grams) was continuously removed from the reaction by azeotropic distillation The final solution was evaporated to remove toluene under vacuum

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

Procedure: N,N-dibutylethanolamine glycerol borate was prepared as follows. Boric acid (10.3 grams), glycerol (15.3 grams), and N,N-dibutylethanolamine (28.9 grams) were added to a 250 milliliter flask. One hundred fifty milliliters of toluene was then added. The reaction was allowed to proceed overnight at 110° C., and the byproduct water (˜9 grams) was continuously removed from the reaction by azeotropic distillation. The final solution was evaporated to remove toluene under vacuum, and a brownish viscous liquid product (˜45 grams) of N,N-dibutylethanolamine/glycerol borate was obtained. N,N-dibutylethanolamine glycerol borate was prepared the byproduct water (˜9 grams) was continuously removed from the reaction by azeotropic distillation The final solution was evaporated to remove toluene under vacuum

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 500 mL round bottomed flask fitted with a magnetic stirrer, heating mantle, and distillation head was charged with a mixture of methyl methacrylate (100 g, 1.0 mol, available from TCI), 2-dibutylaminoethanol (43.3 g, 0.25 mol, available from Matheson, Coleman and Bell, Norwood, Ohio), aluminum isopropoxide (5.0 g, 24 mmol, available form Alfa Aesar), and N-phenyl-1-naphthylamine (2.5 g, 11 mmol, available from Aldrich). The mixture was stirred and heated at 80° C. for one hour. The temperature of the reaction mixture was increased 10° C. per hour until a temperature of 110° C. was reached. By this time about 20 mL of material (methanol and methyl methacrylate) had distilled over from the reaction flask. The reaction mixture was left at room temperature overnight. The next day, the reaction mixture was heated at 115° C. for 2 hours and then heated at 135° C. as material distilled from the reaction flask. After 1 hour at 135° C., the desired product, di(butylamino)ethyl methacrylate, was distilled from the reaction flask at reduced pressure and collected at a temperature of 113-118° C. at 2.5 mm pressure. NMR spectral analyses confirmed the structure of the product. The boiling point reported previously for this methacrylate (U.S. Pat. No. 2,138,763 (DuPont)) is 108-109° C. at 2 mm pressure. A 500 mL round bottomed flask fitted with a magnetic stirrer heating mantle distillation head The temperature of the reaction mixture was increased 10° C. per hour until a temperature of 110° C. By this time about 20 mL of material (methanol and methyl methacrylate) had distilled over from the reaction flask The next day, the reaction mixture was heated at 115° C. for 2 hours heated at 135° C. as material distilled from the reaction flask After 1 hour at 135° C. the desired product, di(butylamino)ethyl methacrylate, was distilled from the reaction flask at reduced pressure collected at a temperature of 113-118° C. at 2.5 mm pressure is 108-109° C. at 2 mm pressure

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

Procedure: 70 mmol of 2-(dibutylamino) ethanol, 75 mmol of 1-chlorobutane, and 50 g of ethanol were mixed under N2 atmosphere, and made to react at 80 degrees C. for 8 hours under reflux condition. The ethanol and extra 1-chlorobutane were distilled away therefrom by reducing pressure to produce 70 mmol of (2-hydroxyethyl)tributylammonium chloride. to react at 80 degrees C for 8 hours under reflux condition The ethanol and extra 1-chlorobutane were distilled away

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

Procedure: N,N-dibutylethanolamine/triethylene glycol monobutyl ether borate was prepared as follows. Boric acid (10.3 grams), triethylene glycol monobutyl ether (Fluka, 64.1 grams), and N,N-dibutylethanolamine (28.9 grams) were added to a 250 milliliter flask. One hundred fifty milliliters of toluene was then added. The reaction was allowed to proceed overnight at 110° C., and the byproduct water (˜9 grams) was continuously removed from the reaction by azeotropic distillation. The final solution was evaporated to remove toluene under vacuum, and a brownish liquid product (˜90 grams) of N,N-dibutylethanolamine/triethylene glycol monobutyl ether borate was obtained. N,N-dibutylethanolamine/triethylene glycol monobutyl ether borate was prepared the byproduct water (˜9 grams) was continuously removed from the reaction by azeotropic distillation The final solution was evaporated to remove toluene under vacuum

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

Procedure: N,N-dibutylethanolamine/sorbitol borate was prepared as follows. Boric acid (10.3 grams), sorbitol (30.4 grams), and N,N-dibutylethanolamine (28.9 grams) were added to a 250 milliliter flask. One hundred fifty milliliters of toluene was then added. The reaction was allowed to proceed overnight at 110° C., and the byproduct water (˜9 grams) was continuously removed from the reaction by azeotropic distillation. The final solution was evaporated to remove toluene under vacuum, and a yellowish resinous product (˜60 grams) of N,N-dibutylethanolamine/sorbitol borate was obtained. N,N-dibutylethanolamine/sorbitol borate was prepared the byproduct water (˜9 grams) was continuously removed from the reaction by azeotropic distillation The final solution was evaporated to remove toluene under vacuum

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

Procedure: N,N-dibutylethanolamine/glycerol borate was prepared as follows. Boric acid (10.3 grams), glycerol (15.3 grams), and N,N-dibutylethanolamine (28.9 grams) were added to a 250 milliliter flask. One hundred fifty milliliters of toluene was then added. The reaction was allowed to proceed overnight at 110° C., and the byproduct water (˜9 grams) was continuously removed from the reaction by azeotropic distillation. The final solution was evaporated to remove toluene under vacuum, and a brownish viscous liquid product (˜45 grams) of N,N-dibutylethanolamine/glycerol borate was obtained. N,N-dibutylethanolamine/glycerol borate was prepared the byproduct water (˜9 grams) was continuously removed from the reaction by azeotropic distillation The final solution was evaporated to remove toluene under vacuum

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

Procedure: N,N-Dibutylaminoethyl Tributylstannyl Ether is prepared from 59.6 gm (0.1 mole) bis(tributyltin) oxide and 34.6 gm (0.2 mole) N,N-dibutylethanolamine in 200 ml benzene. This is stirred and heated to reflux in a system that contains a Dean-Starke tube. After 30 minutes water began to collect in the Dean-Starke tube and after refluxing for a period of 22 hours a total of 1.8 ml of water (theory 1.8 ml) had collected. A rotating evaporator is used to remove the benzene and to provide 95.1 gm of red-orange liquid. This is fractionated at reduced pressure with collection at 163°-166° C. at 0.7 mm of 73.1 gm of yellow liquid (Percent yield - 79). Infrared spectral analysis shows this to be the desired ether. heated to reflux in a system that to collect in the Dean-Starke tube after refluxing for a period of 22 hours a total of 1.8 ml of water (theory 1.8 ml) had collected A rotating evaporator to remove the benzene