trioctylphosphane

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

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

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

Procedure: Tri-n-octyl-n-butylphosphonium bromide is prepared by slowing dripping tri-(n-octyl)phosphine (740 grams) into refluxing 1-bromobutane (500 grams) in a nitrogen atmosphere. Reflux is continued one hour after final addition then the solution is cooled with stirring for about 18 hours, followed by vacuum removal of excess 1-bromobutane at 60° C. This product, 1210 grams from two successive preparations, is added to 880 grams of sodium 3,5-dicarbomethoxybenzenesulfonate in 2500 ml. of water and stirred for at least one hour at 85° C. then the heat is removed and the oil-in-water mixture is stirred for about 18 hours. The oil layer is separated from the water, rinsed with 1000 ml. of water and dried at about 80° C. at a pressure less than 2 torr for 18 hours. This product, an oil, is tri-n-octyl-n-butylphosphonium 3,5-dicarbomethoxybenzenesulfonate with 4.2% phosphorus and 4.7% sulfur by analysis. Reflux after final addition the solution is cooled followed by vacuum removal of excess 1-bromobutane at 60° C This product, 1210 grams from two successive preparations, is added to 880 grams of sodium 3,5-dicarbomethoxybenzenesulfonate in 2500 ml of water and stirred for at least one hour at 85° C. the heat is removed the oil-in-water mixture is stirred for about 18 hours The oil layer is separated from the water rinsed with 1000 ml of water and dried at about 80° C. at a pressure less than 2 torr for 18 hours

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

Procedure: Tri-n-octyl-n-butylphosphonium bromide is prepared by slowing dripping tri-(n-octyl)phosphine (740 grams) into refluxing 1-bromobutane (500 grams) in a nitrogen atmosphere. Reflux is continued one hour after final addition then the solution is cooled with stirring for about 18 hours, followed by vacuum removal of excess 1-bromobutane at 60° C. This product, 1210 grams from two successive preparations, is added to 880 grams of sodium 3,5-dicarbomethoxybenzenesulfonate in 2500 ml. of water and stirred for at least one hour at 85° C. then the heat is removed and the oil-in-water mixture is stirred for about 18 hours. The oil layer is separated from the water, rinsed with 1000 ml. of water and dried at about 80° C. at a pressure less than 2 torr for 18 hours. This product, an oil, is tri-n-octyl-n-butylphosphonium 3,5-dicarbomethoxybenzenesulfonate with 4.2% phosphorus and 4.7% sulfur by analysis. Reflux after final addition the solution is cooled followed by vacuum removal of excess 1-bromobutane at 60° C This product, 1210 grams from two successive preparations, is added to 880 grams of sodium 3,5-dicarbomethoxybenzenesulfonate in 2500 ml of water and stirred for at least one hour at 85° C. the heat is removed the oil-in-water mixture is stirred for about 18 hours The oil layer is separated from the water rinsed with 1000 ml of water and dried at about 80° C. at a pressure less than 2 torr for 18 hours

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

Procedure: To 185 g (0.5 mol) of a commercially available tri-n-octylphosphine (product name: HISHICOLIN (registered trademark) P-8, manufactured by Nippon Chemical Industrial Co., Ltd.), 71 g (0.5 mol) of iodomethane (reagent, manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise under a nitrogen atmosphere, and the mixture was reacted at 30 to 40° C. for 5 hours. After the reaction was completed, 100 ml of hexane was added to the reaction mixture to separate layers. The resulting liquid was then washed three times with hexane and vacuum dried under a degree of vacuum of 0.5 kPa at 80° C. for 3 hours to obtain 205 g (yield 80%) of tri-n-octylmethylphosphonium iodide. To 41 g (0.08 mol) of the resulting tri-n-octylmethylphosphonium iodide, was added 41 g of pure water. To the mixture with stirring, was added 23 g (0.08 mol) of lithium bis(trifluoromethylsulfonyl)imide (reagent, manufactured by Kanto Chemical Co., Inc.) to allow them to react with each other, followed by stirring for 2 hours at room temperature for aging. After the completion of aging with stirring, the lower layer (product) was separated from the mixture and washed four times with pure water. After the completion of the washing, the product was vacuum dried under a degree of vacuum of 0.5 kPa at 80° C. for 3 hours. The structure of the resulting product was examined by 1H-NMR, 13C-NMR, 19F-NMR, and 31P-NMR. The product was identified as tri-n-octylmethylphosphonium bis(trifluoromethylsulfonyl)imide (TOMP-TFSI), and it had a purity of 99%. The resulting TOMP-TFSI was a colorless transparent liquid at room temperature (25° C.), which had a moisture content determined by the Karl Fischer titration method of 65 ppm and a chlorine content determined by ion chromatography of 10 ppm. The amount of the product yielded was 49 g (yield 92%). The product had an electrical conductivity at 25° C. of 0.09 mS/cm. the mixture was reacted at 30 to 40° C. for 5 hours to separate layers The resulting liquid was then washed three times with hexane and vacuum dried under a degree of vacuum of 0.5 kPa at 80° C. for 3 hours

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

Procedure: To 185 g (0.5 mol) of a commercially available tri-n-octylphosphine (product name: HISHICOLIN (registered trademark) P-8, manufactured by Nippon Chemical Industrial Co., Ltd.), 71 g (0.5 mol) of iodomethane (reagent, manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise under a nitrogen atmosphere, and the mixture was reacted at 30 to 40° C. for 5 hours. After the reaction was completed, 100 ml of hexane was added to the reaction mixture to separate layers. The resulting liquid was then washed three times with hexane and vacuum dried under a degree of vacuum of 0.5 kPa at 80° C. for 3 hours to obtain 205 g (yield 80%) of tri-n-octylmethylphosphonium iodide. To 41 g (0.08 mol) of the resulting tri-n-octylmethylphosphonium iodide, was added 41 g of pure water. To the mixture with stirring, was added 23 g (0.08 mol) of lithium bis(trifluoromethylsulfonyl)imide (reagent, manufactured by Kanto Chemical Co., Inc.) to allow them to react with each other, followed by stirring for 2 hours at room temperature for aging. After the completion of aging with stirring, the lower layer (product) was separated from the mixture and washed four times with pure water. After the completion of the washing, the product was vacuum dried under a degree of vacuum of 0.5 kPa at 80° C. for 3 hours. The structure of the resulting product was examined by 1H-NMR, 13C-NMR, 19F-NMR, and 31P-NMR. The product was identified as tri-n-octylmethylphosphonium bis(trifluoromethylsulfonyl)imide (TOMP-TFSI), and it had a purity of 99%. The resulting TOMP-TFSI was a colorless transparent liquid at room temperature (25° C.), which had a moisture content determined by the Karl Fischer titration method of 65 ppm and a chlorine content determined by ion chromatography of 10 ppm. The amount of the product yielded was 49 g (yield 92%). The product had an electrical conductivity at 25° C. of 0.09 mS/cm. the mixture was reacted at 30 to 40° C. for 5 hours to separate layers The resulting liquid was then washed three times with hexane and vacuum dried under a degree of vacuum of 0.5 kPa at 80° C. for 3 hours

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

Procedure: Materials. 1-methyl-2-pyrrolidinone (99.5%, Aldrich), 1-octadecene (90%, Aldrich), acetonitrile (99.9%, Fisher Chemical), BiCl3 (99.999%, Strem), CdO (99.5%, Aldrich), diphenyl ether (99%, Aldrich), methanol (ACS grade, VWR), oleic acid (90%, Aldrich), oleylamine (70% Aldrich), selenium (99.99%, Strem), trioctylphosphine (90%, Aldrich), trioctylphosphine oxide (99%, Strem), toluene (ACS grade, VWR). 0.1M Se-ODE was prepared by dissolving selenium powder in 1-octadecene at 180° C. for 5 hr under inert atmosphere according to the procedure by Bullen et al.[42]; trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile prior to use; di-n-octylphosphinic acid (DOPA) was synthesized according to the procedure reported by Wang et al.[1]; a stock suspension of 2 mM BiCl3 in NMP was prepared in advance. 0.1M Se-ODE was prepared trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile was prepared in advance

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

Procedure: Materials. 1-methyl-2-pyrrolidinone (99.5%, Aldrich), 1-octadecene (90%, Aldrich), acetonitrile (99.9%, Fisher Chemical), triphenylbismuth (99%, Strem), CdO (99.5%, Aldrich), diphenyl ether (99%, Aldrich), methanol (ACS grade, VWR), oleic acid (90%, Aldrich), oleylamine (70% Aldrich), selenium (99.99%, Strem), trioctylphosphine (90%, Aldrich), trioctylphosphine oxide (99%, Strem), toluene (ACS grade, VWR). 0.2M Se-ODE was prepared by dissolving selenium powder in 1-octadecene at 200° C. for 2 hr under inert atmosphere according to the procedure by Bullen et al.[42]; trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile prior to use; di-n-octylphosphinic acid (DOPA) was synthesized according to the procedure reported by Wang et al.[1]; a stock suspension of 2 mM triphenylbismuth (BiPh3) in 1-octadecene was prepared in advance. 0.2M Se-ODE was prepared trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile was prepared in advance

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

Procedure: Materials. 1-methyl-2-pyrrolidinone (99.5%, Aldrich), 1-octadecene (90%, Aldrich), acetonitrile (99.9%, Fisher Chemical), triphenylbismuth (99%, Strem), CdO (99.5%, Aldrich), diphenyl ether (99%, Aldrich), methanol (ACS grade, VWR), oleic acid (90%, Aldrich), oleylamine (70% Aldrich), selenium (99.99%, Strem), trioctylphosphine (90%, Aldrich), trioctylphosphine oxide (99%, Strem), toluene (ACS grade, VWR). 0.2M Se-ODE was prepared by dissolving selenium powder in 1-octadecene at 200° C. for 2 hr under inert atmosphere according to the procedure by Bullen et al.[42]; trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile prior to use; di-n-octylphosphinic acid (DOPA) was synthesized according to the procedure reported by Wang et al.[1]; a stock suspension of 2 mM triphenylbismuth (BiPh3) in 1-octadecene was prepared in advance. 0.2M Se-ODE was prepared trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile was prepared in advance

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

Procedure: Materials. 1-methyl-2-pyrrolidinone (99.5%, Aldrich), 1-octadecene (90%, Aldrich), acetonitrile (99.9%, Fisher Chemical), BiCl3 (99.999%, Strem), CdO (99.5%, Aldrich), diphenyl ether (99%, Aldrich), methanol (ACS grade, VWR), oleic acid (90%, Aldrich), oleylamine (70% Aldrich), selenium (99.99%, Strem), trioctylphosphine (90%, Aldrich), trioctylphosphine oxide (99%, Strem), toluene (ACS grade, VWR). 0.1M Se-ODE was prepared by dissolving selenium powder in 1-octadecene at 180° C. for 5 hr under inert atmosphere according to the procedure by Bullen et al. [42]; trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile prior to use; di-n-octylphosphinic acid (DOPA) was synthesized according to the procedure reported by Wang et al. [1], a stock suspension of 2 mM BiCl3 in NMP was prepared in advance. 0.1M Se-ODE was prepared trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile was prepared in advance

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

Procedure: Tri-n-octyl-n-butylphosphonium bromide is prepared by slowly dripping tri-(n-octyl)phosphine (740 grams) into refluxing 1-bromobutane (500 grams) in a nitrogen atmosphere. Reflux is continued one hour after final addition then the solution is cooled with stirring for about 18 hours, followed by vacuum removal of excess 1-bromobutane at 60° C. This product, 1210 grams from two successive preparations, is added to 880 grams of sodium 3,5-dicarbomethoxybenzenesulfonate in 2500 milliliters of water and stirred for at least 1 hour at 85° C. then the heat is removed and the oil in water mixture is allowed to stir and cool for about 18 hours. The oil layer is separated from the water, rinsed with 1000 milliliters of water and dried at about 80° C. at a pressure less than 2 torr for 18 hours. This product, an oil, is tri-n-octyl-n-butylphosphonium 3,5-dicarbomethoxybenzenesulfonate with 4.2% phosphorous and 4.7% sulfur by analysis. Reflux after final addition the solution is cooled followed by vacuum removal of excess 1-bromobutane at 60° C This product, 1210 grams from two successive preparations, is added to 880 grams of sodium 3,5-dicarbomethoxybenzenesulfonate in 2500 milliliters of water stirred for at least 1 hour at 85° C. the heat is removed to stir cool for about 18 hours The oil layer is separated from the water rinsed with 1000 milliliters of water dried at about 80° C. at a pressure less than 2 torr for 18 hours

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

Procedure: Tri-n-octyl-n-butylphosphonium bromide is prepared by slowly dripping tri-(n-octyl)phosphine (740 grams) into refluxing 1-bromobutane (500 grams) in a nitrogen atmosphere. Reflux is continued one hour after final addition then the solution is cooled with stirring for about 18 hours, followed by vacuum removal of excess 1-bromobutane at 60° C. This product, 1210 grams from two successive preparations, is added to 880 grams of sodium 3,5-dicarbomethoxybenzenesulfonate in 2500 milliliters of water and stirred for at least 1 hour at 85° C. then the heat is removed and the oil in water mixture is allowed to stir and cool for about 18 hours. The oil layer is separated from the water, rinsed with 1000 milliliters of water and dried at about 80° C. at a pressure less than 2 torr for 18 hours. This product, an oil, is tri-n-octyl-n-butylphosphonium 3,5-dicarbomethoxybenzenesulfonate with 4.2% phosphorous and 4.7% sulfur by analysis. Reflux after final addition the solution is cooled followed by vacuum removal of excess 1-bromobutane at 60° C This product, 1210 grams from two successive preparations, is added to 880 grams of sodium 3,5-dicarbomethoxybenzenesulfonate in 2500 milliliters of water stirred for at least 1 hour at 85° C. the heat is removed to stir cool for about 18 hours The oil layer is separated from the water rinsed with 1000 milliliters of water dried at about 80° C. at a pressure less than 2 torr for 18 hours