1,1,3,3-tetrabutylurea

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 56.9 grams (200 mmol.) of tetra-n-butylurea, 32.2 grams (210 mmol.) of phosphorus oxychloride and 75 ml. of acetonitrile was heated at 75° C. in a nitrogen atmosphere for one hour. The mixture was then cooled to 0° C. and 33.6 grams (460 mmol.) of n-butylamine was added over 15 minutes with stirring, whereupon a soft, fluffy precipitate formed. The mixture was warmed to 60° C. for one hour and again cooled to 0° C., quenched with 50 ml. of 25% (by weight) aqueous sodium hydroxide solution and extracted with ether. The ether extracts were dried over magnesium sulfate, filtered and stripped to give a pale yellow oil which, upon distillation, yielded 56.32 grams (83% of theoretical) of penta-n-butylguanidine. whereupon a soft, fluffy precipitate formed The mixture was warmed to 60° C. for one hour again cooled to 0° C. quenched with 50 ml of 25% (by weight) aqueous sodium hydroxide solution and extracted with ether The ether extracts were dried over magnesium sulfate filtered to give a pale yellow oil which upon distillation

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

Procedure: In a 1.75-liter continuously stirred tank-type reactor with internal filters to retain the catalyst inside the reactor, operating at a volume of 1.25 liters, a temperature of 43°-45° C. and pressure of 15 psig, a working solution was circulated at a flow rate of 50 ml/min. The working solution initially contained 18 wt % ethylanthraquinone, of which 45 wt % was tetrahydroethylanthraquinone, 58 wt % of an aromatic solvent (alkylated benzenes - heavy naphtha fraction, Aromatic 150), and 24 wt % tetra-n-butylurea. The hydrogen feed rate was controlled to give a maximum reduction level (anthrahydroquinone or HQ titer) of 0.408 g mol/l. 2.254 g of a 2.6 wt % palladium on gamma alumina catalyst was added to the reactor. a temperature of 43°-45° C. and pressure of 15 psig

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

Procedure: In a 1.75-liter continuously stirred tank-type reactor with internal filters to retain the catalyst inside the reactor, operating at a volume of 1.25 liters, a temperature of 43°-45° C. and pressure of 15 psig, a working solution was circulated at a flow rate of 50 ml/min. The working solution initially contained 18 wt % ethylanthraquinone, of which 45 wt % was tetrahydroethylanthraquinone, 58 wt % of an aromatic solvent (alkylated benzenes - heavy naphtha fraction, Aromatic 150), and 24 wt % tetra-n-butylurea. The hydrogen feed rate was controlled to give a maximum reduction level (anthrahydroquinone or HQ titer) of 0.408 g mol/l. 2.254 g of a 2.6 wt % palladium on gamma alumina catalyst was added to the reactor. a temperature of 43°-45° C. and pressure of 15 psig

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 56.9 grams (200 mmol.) of tetra-n-butylurea, 32.2 grams (210 mmol.) of phosphorus oxychloride and 75 ml. of acetonitrile was heated at 75° C. in a nitrogen atmosphere for one hour. The mixture was then cooled to 0° C. and 33.6 grams (460 mmol.) of n-butylamine was added over 15 minutes with stirring, whereupon a soft, fluffy precipitate formed. The mixture was warmed to 60° C. for one hour and again cooled to 0° C., quenched with 50 ml. of 25% (by weight) aqueous sodium hydroxide solution and extracted with ether. The ether extracts were dried over magnesium sulfate, filtered and stripped to give a pale yellow oil which, upon distillation, yielded 56.32 grams (83% of theoretical) of penta-n-butylguanidine. whereupon a soft, fluffy precipitate formed The mixture was warmed to 60° C. for one hour again cooled to 0° C. quenched with 50 ml of 25% (by weight) aqueous sodium hydroxide solution and extracted with ether The ether extracts were dried over magnesium sulfate filtered to give a pale yellow oil which upon distillation

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 5.69 grams (20 mmol) of tetra-n-butylurea, 3.22 grams (21 mmol) of phosphorus oxychloride and 15 ml of acetonitrile was heated at 75° C. in a nitrogen atmosphere for one hour. The mixture was then cooled to 0° C. and 3.36 grams (46 mmol) of n-butylamine was added over 15 minutes with stirring. The mixture was warmed to 60° C. for one hour and again cooled to 0° C., quenched with 5 ml of 25% (by weight) aqueous sodium hydroxide solution and extracted with diethylether. The ether extracts were dried over sodium sulphate, filtered and stripped to give a pale yellow oil of penta-n-butylguanidine. The mixture was then cooled to 0° C. The mixture was warmed to 60° C. for one hour again cooled to 0° C. quenched with 5 ml of 25% (by weight) aqueous sodium hydroxide solution extracted with diethylether The ether extracts were dried over sodium sulphate filtered

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 56.9 grams (200 mmol.) of tetra-n-butylurea, 32.2 grams (210 mmol.) of phosphorus oxychloride and 75 ml. of acetonitrile was heated at 75° C. in a nitrogen atmosphere for one hour. The mixture was then cooled to 0° C. and 33.6 grams (460 mmol.) of n-butylamine was added over 15 minutes with stirring, whereupon a soft, fluffy precipitate formed. The mixture was warmed to 60° C. for one hour and again cooled to 0° C., quenched with 50 ml. of 25% (by weight) aqueous sodium hydroxide solution and extracted with ether. The ether extracts were dried over magnesium sulfate, filtered and stripped to give a pale yellow oil which, upon distillation, yielded 56.32 grams (83% of theoretical) of penta-n-butylguanidine. whereupon a soft, fluffy precipitate formed The mixture was warmed to 60° C. for one hour again cooled to 0° C. quenched with 50 ml of 25% (by weight) aqueous sodium hydroxide solution and extracted with ether The ether extracts were dried over magnesium sulfate filtered to give a pale yellow oil which upon distillation

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 56.9 grams (200 mmol.) of tetra-n-butylurea, 32.2 grams (210 mmol.) of phosphorus oxychloride and 75 ml. of acetonitrile was heated at 75° C. in a nitrogen atmosphere for one hour. The mixture was then cooled to 0° C. and 33.6 grams (460 mmol.) of n-butylamine was added over 15 minutes with stirring, whereupon a soft, fluffy precipitate formed. The mixture was warmed to 60° C. for one hour and again cooled to 0° C., quenched with 50 ml. of 25% (by weight) aqueous sodium hydroxide solution and extracted with ether. The ether extracts were dried over magnesium sulfate, filtered and stripped to give a pale yellow oil which, upon distillation, yielded 56.32 grams (83% of theoretical) of penta-n-butylguanidine. whereupon a soft, fluffy precipitate formed The mixture was warmed to 60° C. for one hour again cooled to 0° C. quenched with 50 ml of 25% (by weight) aqueous sodium hydroxide solution and extracted with ether The ether extracts were dried over magnesium sulfate filtered to give a pale yellow oil which upon distillation

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 56.9 grams (200 mmol.) of tetra-n-butylurea, 32.2 grams (210 mmol.) of phosphorus oxychloride and 75 ml. of acetonitrile was heated at 75° C. in a nitrogen atmosphere for one hour. The mixture was then cooled to 0° C. and 33.6 grams (460 mmol.) of n-butylamine was added over 15 minutes with stirring, whereupon a soft, fluffy precipitate formed. The mixture was warmed to 60° C. for one hour and again cooled to 0° C., quenched with 50 ml. of 25% (by weight) aqueous sodium hydroxide solution and extracted with ether. The ether extracts were dried over magnesium sulfate, filtered and stripped to give a pale yellow oil which, upon distillation, yielded 56.32 grams (83% of theoretical) of penta-n-butylguanidine. whereupon a soft, fluffy precipitate formed The mixture was warmed to 60° C. for one hour again cooled to 0° C. quenched with 50 ml of 25% (by weight) aqueous sodium hydroxide solution and extracted with ether The ether extracts were dried over magnesium sulfate filtered to give a pale yellow oil which upon distillation

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 56.9 grams (200 mmol.) of tetra-n-butylurea, 32.2 grams (210 mmol.) of phosphorus oxychloride and 75 ml. of acetonitrile was heated at 75° C. in a nitrogen atmosphere for one hour. The mixture was then cooled to 0° C. and 33.6 grams (460 mmol.) of n-butylamine was added over 15 minutes with stirring, whereupon a soft, fluffy precipitate formed. The mixture was warmed to 60° C. for one hour and again cooled to 0° C., quenched with 50 ml. of 25% (by weight) aqueous sodium hydroxide solution and extracted with ether. The ether extracts were dried over magnesium sulfate, filtered and stripped to give a pale yellow oil which, upon distillation, yielded 56.32 grams (83% of theoretical) of penta-n-butylguanidine. whereupon a soft, fluffy precipitate formed The mixture was warmed to 60° C. for one hour again cooled to 0° C. quenched with 50 ml of 25% (by weight) aqueous sodium hydroxide solution and extracted with ether The ether extracts were dried over magnesium sulfate filtered to give a pale yellow oil which upon distillation

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 5.69 grams (20 mmol) of tetra-n-butylurea, 3.22 grams (21 mmol) of phosphorus oxychloride and 15 ml of acetonitrile was heated at 75° C. in a nitrogen atmosphere for one hour. The mixture was then cooled to 0° C. and 3.36 grams (46 mmol) of n-butylamine was added over 15 minutes with stirring. The mixture was warmed to 60° C. for one hour and again cooled to 0° C., quenched with 5 ml of 25% (by weight) aqueous sodium hydroxide solution and extracted with diethylether. The ether extracts were dried over sodium sulphate, filtered and stripped to give a pale yellow oil of penta-n-butylguanidine. The mixture was then cooled to 0° C. The mixture was warmed to 60° C. for one hour again cooled to 0° C. quenched with 5 ml of 25% (by weight) aqueous sodium hydroxide solution extracted with diethylether The ether extracts were dried over sodium sulphate filtered

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

Procedure: In a 1.75-liter continuously stirred tank-type reactor with internal filters to retain the catalyst inside the reactor, operating at a volume of 1.25 liters, a temperature of 43°-45° C. and pressure of 15 psig, a working solution was circulated at a flow rate of 50 ml/min. The working solution initially contained 18 wt % ethylanthraquinone, of which 45 wt % was tetrahydroethylanthraquinone, 58 wt % of an aromatic solvent (alkylated benzenes - heavy naphtha fraction, Aromatic 150), and 24 wt % tetra-n-butylurea. The hydrogen feed rate was controlled to give a maximum reduction level (anthrahydroquinone or HQ titer) of 0.408 g mol/l. 2.254 g of a 2.6 wt % palladium on gamma alumina catalyst was added to the reactor. a temperature of 43°-45° C. and pressure of 15 psig

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 56.9 grams (200 mmol.) of tetra-n-butylurea, 32.2 grams (210 mmol.) of phosphorus oxychloride and 75 ml. of acetonitrile was heated at 75° C. in a nitrogen atmosphere for one hour. The mixture was then cooled to 0° C. and 33.6 grams (460 mmol.) of n-butylamine was added over 15 minutes with stirring, whereupon a soft, fluffy precipitate formed. The mixture was warmed to 60° C. for one hour and again cooled to 0° C., quenched with 50 ml. of 25% (by weight) aqueous sodium hydroxide solution and extracted with ether. The ether extracts were dried over magnesium sulfate, filtered and stripped to give a pale yellow oil which, upon distillation, yielded 56.32 grams (83% of theoretical) of penta-n-butylguanidine. whereupon a soft, fluffy precipitate formed The mixture was warmed to 60° C. for one hour again cooled to 0° C. quenched with 50 ml of 25% (by weight) aqueous sodium hydroxide solution and extracted with ether The ether extracts were dried over magnesium sulfate filtered to give a pale yellow oil which upon distillation