2-ethyl-N-(2-ethylhexyl)hexan-1-amine

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3,3,3-Trifluoropropyl(bis(2-ethylhexyl)aminodimethoxysilane--A 500 mL round bottomed flask was charged with tetrahydrofuran (300 mL) and isopropylmagnesium chloride (25 mL of a 2.0 M solution in THF, 50 mmol). The contents were cooled to 15° C. Bis(2-ethylhexyl)amine (50 mmol) was added over fifteen minutes via pressure equalizing addition funnel. The cold bath was removed and the contents stirred for two hours. 3,3,3-Trifluoropropyltrimethoxysilane (45 mmol) was added via pressure equalizing addition funnel. The contents were brought to reflux (65-70° C.) for two hours, and reaction progress was monitored by GC. Isolation was accomplished by removing the THF via rotary evaporation, taking the residue up in ether (250 mL), filtration and ether removal via rotary evaporation. Purification was accomplished by distillation to provide 3,3,3-trifluoropropyl bis(2-ethylhexyl)aminodimethoxysilane (44 mmol; 98% yield). C21H44NO2SiF3 (mw=427.66) bp=200° C. at 1.4 mmHg; 1H NMR: (CDCl3) δ 3.5 (s, 6H), 2.6-2.4 (dd, 4H), 2.2-2.0 (m, 2H), 1.6-1.1 (m, 18H), 1.0-0.7 (m, 14H); 13C NMR: (CDCl3) δ 128 (quartet, J=275 Hz), 50.4, 48.5, 39.4, 36.9, 30.8, 29.1, 28.2 (quartet, J=30 Hz), 23.2, 14.2, 10.3, 3.2; MS: m/z (relative abundance) 328 (100), 230 (25.6), 155 (7.4), 109 (2.9). addition funnel The cold bath was removed addition funnel to reflux (65-70° C.) for two hours reaction progress by removing the THF via rotary evaporation up in ether (250 mL), filtration and ether removal via rotary evaporation Purification was accomplished by distillation

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

Procedure: 41.3 Gm. (0.2 mole) of dicyclohexylcarbodiimide, 72.4 gm. (0.3 mole) of bis-2-ethylhexylamine, and 200 ml. of t-butanol were refluxed for 7 hours. The t-butanol was distilled off at atmospheric pressure and the residue stripped to a temperature of 180° C. at 0.08-0.09 mm Hg. The residue weighed 60.8 gm. and was 90% pure by NMR with a trace of amine and approximately 5% dicyclohexylcarbodiimide. The t-butanol was distilled off at atmospheric pressure stripped to a temperature of 180° C. at 0.08-0.09 mm Hg

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

Procedure: A mixture of epichlorohydrin (111 g, 1.2 mol), and water (0.27 g, 0.015 mol) was vigorously stirred at room temperature. Bis(2-ethylhexyl)amine (241.4 g, 1.0 mol) was added slowly by an addition funnel. The mixture was slowly heated to 70° C. and then stirred at 70° C. for 6 hours. The mixture was washed with aqueous potassium carbonate, K2CO3, (20%, 200 ml). Sodium hydroxide, NaOH, (36%, 200 ml) was added to the oil phase and the mixture was stirred at 70-90° C. for 18 hours. The phases were separated and extracted with ethyl acetate (3×100 ml). The combined extracts were washed with brine, dried over magnesium sulfate, MgSO4, and the solvent removed by rotary evaporation. The mixture was slowly heated to 70° C. stirred at 70° C. for 6 hours The mixture was washed with aqueous potassium carbonate, K2CO3, (20%, 200 ml) Sodium hydroxide, NaOH, (36%, 200 ml) was added to the oil phase the mixture was stirred at 70-90° C. for 18 hours The phases were separated extracted with ethyl acetate (3×100 ml) The combined extracts were washed with brine dried over magnesium sulfate, MgSO4 the solvent removed by rotary evaporation

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

Procedure: A mixture of epichlorohydrin (111 g, 1.2 mol), and water (0.27 g, 0.015 mol) was vigorously stirred at room temperature. Bis(2-ethylhexyl)amine (241.4 g, 1.0 mol) was added slowly by an addition funnel. The mixture was slowly heated to 70° C. and then stirred at 70° C. for 6 hours. The mixture was washed with aqueous potassium carbonate, K2CO3, (20%, 200 ml). Sodium hydroxide, NaOH, (36%, 200 ml) was added to the oil phase and the mixture was stirred at 70-90° C. for 18 hours. The phases were separated and extracted with ethyl acetate (3×100 ml). The combined extracts were washed with brine, dried over magnesium sulfate, MgSO4, and the solvent removed by rotary evaporation. The mixture was slowly heated to 70° C. stirred at 70° C. for 6 hours The mixture was washed with aqueous potassium carbonate, K2CO3, (20%, 200 ml) Sodium hydroxide, NaOH, (36%, 200 ml) was added to the oil phase the mixture was stirred at 70-90° C. for 18 hours The phases were separated extracted with ethyl acetate (3×100 ml) The combined extracts were washed with brine dried over magnesium sulfate, MgSO4 the solvent removed by rotary evaporation

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 250.8 g (1.5 moles) of 2-mercaptobenzothiazole in 1500 ml of methanol are added 112.8 ml (1.5 moles) of 37% aqueous formaldehyde, followed by the dropwise addition, with stirring, of 362.4 g (1.5 moles) of bis(2-ethylhexyl)amine. The mixture is stirred for 15 hours at 50° C. and then concentrated by evaporation in vacuo, affording as residue 618 g of 3-[bis(2-ethylhexyl)aminomethyl]benzothiazoline-2-thione as a reddish brown oil followed by the dropwise addition concentrated by evaporation in vacuo

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

Procedure: To 200 ml of acetonitrile were added 14.8 g of phthalic anhydride and 24.2 g of di(2-ethylhexyl)amine and the mixture was refluxed for 2 hours and then concentrated to provide 39.0 g of oily 2-{N,N-di(2-ethylhexyl)carbamoyl}-benzoic acid. the mixture was refluxed for 2 hours concentrated

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

Procedure: N,N-bis(2'-ethylhexyl)pyrazine-2-carboxamide was prepared from pyrazine-2-carboxylic acid and bis(2-ethylhexyl)amine by the general method of Example 5, the amine being used in place of the alcohol. The compound had a boiling range of 155° to 160° C. at 0.2 mm pressure of mercury.

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

Procedure: N,N-bis(2'-ethylhexyl)pyrazine-2-carboxamide was prepared from pyrazine-2-carboxylic acid and bis(2-ethylhexyl)amine by the general method of Example 5, the amine being used in place of the alcohol. The compound had a boiling range of 155° to 160° C. at 0.2 mm pressure of mercury.

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3,3,3-Trifluoropropyl(bis(2-ethylhexyl)aminodimethoxysilane--A 500 mL round bottomed flask was charged with tetrahydrofuran (300 mL) and isopropylmagnesium chloride (25 mL of a 2.0 M solution in THF, 50 mmol). The contents were cooled to 15° C. Bis(2-ethylhexyl)amine (50 mmol) was added over fifteen minutes via pressure equalizing addition funnel. The cold bath was removed and the contents stirred for two hours. 3,3,3-Trifluoropropyltrimethoxysilane (45 mmol) was added via pressure equalizing addition funnel. The contents were brought to reflux (65-70° C.) for two hours, and reaction progress was monitored by GC. Isolation was accomplished by removing the THF via rotary evaporation, taking the residue up in ether (250 mL), filtration and ether removal via rotary evaporation. Purification was accomplished by distillation to provide 3,3,3-trifluoropropyl bis(2-ethylhexyl)aminodimethoxysilane (44 mmol; 98% yield). C21H44NO2SiF3 (mw=427.66) bp=200° C. at 1.4 mmHg; 1H NMR: (CDCl3) δ 3.5 (s, 6H), 2.6-2.4 (dd, 4H), 2.2-2.0 (m, 2H), 1.6-1.1 (m, 18H), 1.0-0.7 (m, 14H); 13C NMR: (CDCl3) δ 128 (quartet, J=275 Hz), 50.4, 48.5, 39.4, 36.9, 30.8, 29.1, 28.2 (quartet, J=30 Hz), 23.2, 14.2, 10.3, 3.2; MS: m/z (relative abundance) 328 (100), 230 (25.6), 155 (7.4), 109 (2.9). addition funnel The cold bath was removed addition funnel to reflux (65-70° C.) for two hours reaction progress by removing the THF via rotary evaporation up in ether (250 mL), filtration and ether removal via rotary evaporation Purification was accomplished by distillation

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

Procedure: Using a mixture of 1,155 g of tri-(2-ethylhexyl)-amine and 1,155 g of xylene (850 l/hr), 505.4 kg of 9.85 percent strength hydrochloric acid containing sodium chloride (250 ml/hr) were extracted in counter-current at 50° C. in the course of 1,913 hours. The extract was subjected to hydrochloride cleavage in the cleavage column at 148°-152° C.; it gave a total of 46.9 kg of hydrogen chloride, of which about one-third was obtained as concentrated hydrochloric acid, alongside hydrogen chloride gas. Since the cleavage takes place virtually quantitatively, an extraction rate of 94.2% can be calculated from the stated amount of HCl. To regenerate the amine, 100 ml per hour of the bottom product from the cleavage column were constantly passed over the adsorption column filled with aluminum oxide. After completion of the example, 1.036 g out of the 1,155 g of tri-(2-ethylhexyl)-amine employed were recovered unchanged; this corresponds to a loss of 119 g or 10.3% relative to amine employed. In addition, di-(2-ethyl-hexyl)-amine in an amount corresponding to 40 g of tertiary amine preparable therefrom could be isolated from the regeneration process. If this is taken into account, the amine loss is reduced to 6.8%. Relative to hydrogen chloride produced, the amine loss is calculated to be 0.17%.

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

Procedure: Step A is conducted starting from 2,2′-diethylhexylamine and 4-chlorobutanoyl chloride and leads to 4-chloro-N,N-bis(2-ethylhexyl)butanamide (Yield: quantitative) for which the 1H and 13C NMR characterisations give:

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

Procedure: Step A is conducted using 2,2′-diethylhexylamine and 3-bromo-propanoyl chloride and leads to 3-bromo-N,N-bis(2-ethylhexyl)propanamide (Yield: 97%) for which the 1H and 13C NMR characterisations are given below: