N,N-dimethyldodecan-1-amine

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

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

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: 43.3 g (0.2 mol) of N,N-dimethyldodecylamine were added in portions with stirring to 30.0 g (0.3 mol) of concentrated hydrochloric acid (37 wt. %). After the exothermic reaction (up to approx. 35° C.), the highly viscous mixture was diluted with 25 ml of concentrated hydrochloric acid and 25 ml of water and stirred overnight. The aqueous phase was then extracted with 100 ml of methylene chloride, the organic phase was washed once with 50 ml of water, dried with sodium sulfate and the solvent was removed under a vacuum. In order to remove any traces of water, the residue was resuspended in 50 ml of toluene and concentrated under a vacuum and the operation was then repeated in 80 ml of hexane. Once the solvent had again been removed by distillation under a vacuum, N,N-dimethyldodecylammonium hydrochloride was obtained as a colourless solid. After the exothermic reaction (up to approx. 35° C.) The aqueous phase was then extracted with 100 ml of methylene chloride the organic phase was washed once with 50 ml of water dried with sodium sulfate the solvent was removed under a vacuum In order to remove any traces of water concentrated under a vacuum Once the solvent had again been removed by distillation under a vacuum

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

Procedure: (4-Chlorobutyl)dodecyldimethylammonium bromide and (6-chlorohexyl) dodecyldimethylammonium bromide can be prepared by a similar process using the appropriate bromochloroalkane and dodecyldimethylamine.

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

Procedure: In Example 1 of U.S. Pat. No. 4 138 437, dimethylamine is reacted with 1-dodecanol in the presence of hydrogen and copper chromite as catalyst. To work up the reaction product, it is filtered off from the catalyst and a dodecyldimethylamine is produced as crude product. The crude product is subjected to vacuum distillation to separate off high-boiling byproducts. The distilled C12 -alkyldimethylamine obtained after taking off a first runnings contains about 140 ppm of monomethylamine, 150 ppm of dimethylamine and about 64 ppm of trimethylamine and has a more or less unpleasant odor. is filtered off from the catalyst

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

Procedure: In Example 1 of U.S. Pat. No. 4 138 437, dimethylamine is reacted with 1-dodecanol in the presence of hydrogen and copper chromite as catalyst. To work up the reaction product, it is filtered off from the catalyst and a dodecyldimethylamine is produced as crude product. The crude product is subjected to vacuum distillation to separate off high-boiling byproducts. The distilled C12 -alkyldimethylamine obtained after taking off a first runnings contains about 140 ppm of monomethylamine, 150 ppm of dimethylamine and about 64 ppm of trimethylamine and has a more or less unpleasant odor. is filtered off from the catalyst

Conditions: temp:58.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 500 mL, round-bottomed flask equipped with air condensers and magnetic stirring was charged N,N-dimethyldodecylamine (95.13 grams, 0.513 moles), 1-bromo-6-chlorohexane (102.40 grams, 0.513 moles) and tert-butylmethylether (200 mL). The reaction was maintained at 58° C. for 14 hours. During this time a white precipitate formed. The reaction was cooled to room temperature and tert-butylmethylether (350 mL) was added. Solids were collected by vacuum filtration The mother liquor was allowed to react further at 60° C. and solids were collected in a similar fashion. The combined solids were dried in a vacuum oven at 35° C. for 24 hours, yielding 127.36 grams. To a 500 mL, round-bottomed flask equipped with air condensers During this time a white precipitate formed The reaction was cooled to room temperature Solids were collected by vacuum filtration The mother liquor to react further at 60° C. solids were collected in a similar fashion The combined solids were dried in a vacuum oven at 35° C. for 24 hours yielding 127.36 grams

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 1000 mL, round-bottomed flask equipped with air condensers and a magnetic stirring plate was charged N,N-dimethyldodecylamine (186.46 grams, 0.875 moles), 1-bromo-2-chloroethane (125.60 grams, 0.875 moles) and methanol (150 mL). The reaction was maintained at 65° C. for 48 hours. Solvent was removed by rotary evaporation under reduced pressure to yield brown oil. The oil was placed in a beaker and stirred with t-butylmethylether (2 L) causing a brownish white precipitate to form. The solids were collected by vacuum filtration. Solids were dried in a vacuum oven at 30° C. overnight Yield 197.0 grams (0.55 moles, 63%). Into a 1000 mL, round-bottomed flask equipped with air condensers Solvent was removed by rotary evaporation under reduced pressure to yield brown oil to form The solids were collected by vacuum filtration Solids were dried in a vacuum oven at 30° C. overnight Yield 197.0 grams (0.55 moles, 63%)

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 1000 mL, round-bottomed flask equipped with air condensers and a magnetic stirring plate was charged N,N-dimethyldodecylamine (186.46 grams, 0.875 moles), 1-bromo-2-chloroethane (125.60 grams, 0.875 moles) and methanol (150 mL). The reaction was maintained at 65° C. for 48 hours. Solvent was removed by rotary evaporation under reduced pressure to yield brown oil. The oil was placed in a beaker and stirred with t-butylmethylether (2 L) causing a brownish white precipitate to form. The solids were collected by vacuum filtration. Solids were dried in a vacuum oven at 30° C. overnight Yield 197.0 grams (0.55 moles, 63%). Into a 1000 mL, round-bottomed flask equipped with air condensers Solvent was removed by rotary evaporation under reduced pressure to yield brown oil to form The solids were collected by vacuum filtration Solids were dried in a vacuum oven at 30° C. overnight Yield 197.0 grams (0.55 moles, 63%)

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 1000 mL, round-bottomed flask equipped with air condensers and a magnetic stirring plate was charged N,N-dimethyldodecylamine (308.8 grams, 1.45 moles), 1-bromo-4-chlorobutane (249.98 grams, 1.45 moles) and 300 mL of methanol. The reaction was maintained at 65° C. for 48 hours. Solvent was removed by rotary evaporation under reduced pressure to yield brown oil. To the oil was added 100 ml of 1-butanol. The mixture was distilled under vacuum at 30° C. to 50° C. until distillate stopped collecting Yield 384.47 grams (0.99 moles, 69%). Into a 1000 mL, round-bottomed flask equipped with air condensers Solvent was removed by rotary evaporation under reduced pressure to yield brown oil The mixture was distilled under vacuum at 30° C. to 50° C. until distillate stopped collecting Yield 384.47 grams (0.99 moles, 69%)