N'-[2-(2-aminoethylamino)ethyl]ethane-1,2-diamine

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

Procedure: To a 1 liter 5 neck flask fitted with a reflux condenser and dropping funnel is added 234.3 grams (2 mole) 70% phosphorous acid. Triethylenetetramine, 146 grams (1 mole) is then added dropwise while stirring, followed by 146 grams (4 moles) anhydrous HCl. The mixture is then heated to reflux and 162.2 grams (2 moles) 37% aqueous formaldehyde is added dropwise over 1 hour. Reflux is maintained for 2 hours after formaldehyde addition is complete, after which the reaction mixture containing the amino methylene phosphonic acid product is cooled and bottled. The mixture is then heated to reflux Reflux is maintained for 2 hours is cooled

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

Procedure: 7.3 g of triethylenetetramine (0.05 mol) in 30 ml. of toluene was heated to 75° C. and a mixture of 5.3 g of sodium carbonate and 67.3 g of perfluorodecenyloxybenzene sulfonyl chloride was added over a period of 20 minutes while maintaining the temperature at 80° C. After half an hour of further reaction at 80°-90° C., the reaction mixture was stripped of solvent to a temperature of 150° C. and 45 mm mercury pressure. There was then added 16.4 g of behenic acid (0.05 mol) and 30 ml. of toluene and the mixture was reacted at 115°-120° C. until 0.05 mol of water had evolved (11/4 hours). The solvent was then stripped to a temperature of 100° C. and 30 mm. mercury pressure to yield the product, triethylenetetramine bis-(perfluorodecenyloxybenzene sulfonamide) monobehenamide, a tan, hard solid with good oil, water and soil repellancy. was added over a period of 20 minutes After half an hour of further reaction at 80°-90° C. (11/4 hours) was then stripped to a temperature of 100° C. and 30 mm

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

Procedure: 7.3 g of triethylenetetramine (0.05 mol) in 30 ml. of toluene was heated to 75° C. and a mixture of 5.3 g of sodium carbonate and 67.3 g of perfluorodecenyloxybenzene sulfonyl chloride was added over a period of 20 minutes while maintaining the temperature at 80° C. After half an hour of further reaction at 80°-90° C., the reaction mixture was stripped of solvent to a temperature of 150° C. and 45 mm mercury pressure. There was then added 16.4 g of behenic acid (0.05 mol) and 30 ml. of toluene and the mixture was reacted at 115°-120° C. until 0.05 mol of water had evolved (11/4 hours). The solvent was then stripped to a temperature of 100° C. and 30 mm. mercury pressure to yield the product, triethylenetetramine bis-(perfluorodecenyloxybenzene sulfonamide) monobehenamide, a tan, hard solid with good oil, water and soil repellancy. was added over a period of 20 minutes After half an hour of further reaction at 80°-90° C. (11/4 hours) was then stripped to a temperature of 100° C. and 30 mm

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

Procedure: Stearic acid (285 g, 1 mol) and triethylenetetramine (146 g, 1 mol) was reacted at 163°-166° C. until one mole of water was evolved (28 minutes). To 20.0 g (0.05 mol) of the resulting triethylenetetramine monostearamide dissolved in 200 ml. of toluene was added a mixture of 80.7 g (0.12 mol) of perfluorodecenyloxybenzene sulfonyl chloride and 7.0 g of sodium carbonate over a period of 15 minutes while the temperature was held at 75°-80° C. After 1/2 hour more at 85° C., the solution was decanted from the sodium chloride and the solvent was removed by distillation to yield the product, 2.4 perfluorodecenyloxybenzenesulfonamide triethylenetetramine monostearamide, a tan, hard, waxy, solid with good water, oil and soil repellancy. (28 minutes) was held at 75°-80° C the solution was decanted from the sodium chloride the solvent was removed by distillation

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

Procedure: Stearic acid (285 g, 1 mol) and triethylenetetramine (146 g, 1 mol) was reacted at 163°-166° C. until one mole of water was evolved (28 minutes). To 20.0 g (0.05 mol) of the resulting triethylenetetramine monostearamide dissolved in 200 ml. of toluene was added a mixture of 80.7 g (0.12 mol) of perfluorodecenyloxybenzene sulfonyl chloride and 7.0 g of sodium carbonate over a period of 15 minutes while the temperature was held at 75°-80° C. After 1/2 hour more at 85° C., the solution was decanted from the sodium chloride and the solvent was removed by distillation to yield the product, 2.4 perfluorodecenyloxybenzenesulfonamide triethylenetetramine monostearamide, a tan, hard, waxy, solid with good water, oil and soil repellancy. (28 minutes) was held at 75°-80° C the solution was decanted from the sodium chloride the solvent was removed by distillation

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

Procedure: Behenic acid (98.4 g., 0.3 mol) and triethylenetetramine (43.8 g, 0.3 mol) was reacted at 158°-161° C. until 0.3 mol of water had been evolved (25 minutes) 47.4 g (0.1 mole) of the resulting triethylenetetramine monobehenamide was dissolved in 50 ml. of perchloroethylene. To the resulting solution was added a mixture of 80.0 g (0.12 mol) of perfluorodecenyloxybenzenesulfonyl chloride and 7.0 g of sodium carbonate over a 20 minute period, while holding the temperature at 95°-120° C. After one hour at 90°-120° C., the mixture was worked up as in the preceding example to yield the product, 1.2 perfluorodecenyloxybenzenesulfonamide of triethylene tetramine monobehenamide, a tan, hard, waxy, solid with good oil, water and soil repellancy. was dissolved in 50 ml To the resulting solution was added at 95°-120° C

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

Procedure: Behenic acid (98.4 g., 0.3 mol) and triethylenetetramine (43.8 g, 0.3 mol) was reacted at 158°-161° C. until 0.3 mol of water had been evolved (25 minutes) 47.4 g (0.1 mole) of the resulting triethylenetetramine monobehenamide was dissolved in 50 ml. of perchloroethylene. To the resulting solution was added a mixture of 80.0 g (0.12 mol) of perfluorodecenyloxybenzenesulfonyl chloride and 7.0 g of sodium carbonate over a 20 minute period, while holding the temperature at 95°-120° C. After one hour at 90°-120° C., the mixture was worked up as in the preceding example to yield the product, 1.2 perfluorodecenyloxybenzenesulfonamide of triethylene tetramine monobehenamide, a tan, hard, waxy, solid with good oil, water and soil repellancy. was dissolved in 50 ml To the resulting solution was added at 95°-120° C

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

Procedure: Employing the reaction equipment and general procedures described in Example I, a solution of 229.0 g. (3.75 moles) monoethanolamine and 225.0 g. (3.75 moles) ethylenediamine was admixed with 6.25 g. (0.054 mole; 2.3wt.% and 1.44 mole%, basis MEA) 85% phosphoric acid and heated at 250° C. under 225 - 225 psig pressure for 2.0 hours. Analysis of the reaction product by gas-liquid chromatography (GLC Area %) showed a total conversion of reactants of only 4.7% was obtained. The reaction products were 95.0 diethylenetriamine, 2.5 piperazine and 2.5 Area % N-(2-aminoethyl)-ethanolamine. No higher polyethylene polyamines, e.g., triethylenetetramine, tetraethylenepentamine, etc. were formed. was obtained

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

Procedure: Employing the reaction equipment and general procedures described in Example I, a solution of 229.0 g. (3.75 moles) monoethanolamine and 225.0 g. (3.75 moles) ethylenediamine was admixed with 6.25 g. (0.054 mole; 2.3wt.% and 1.44 mole%, basis MEA) 85% phosphoric acid and heated at 250° C. under 225 - 225 psig pressure for 2.0 hours. Analysis of the reaction product by gas-liquid chromatography (GLC Area %) showed a total conversion of reactants of only 4.7% was obtained. The reaction products were 95.0 diethylenetriamine, 2.5 piperazine and 2.5 Area % N-(2-aminoethyl)-ethanolamine. No higher polyethylene polyamines, e.g., triethylenetetramine, tetraethylenepentamine, etc. were formed. was obtained

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

Procedure: Add 2 g of triethylene tetraamine (with an AV of approximately 1180 mg KOG/g) to 20 ml of toluene in a 250 ml flask fitted with a stirrer, condensor and nitrogen inlet. Add 27.6 g ethylene carbonate to the mixture. Reflux the system for 2.5 hours under N2. Strip the system to yield an ethylene carbonate-triethylene tetraamine adduct having an AV of approximately 104 mg KOH/g. fitted with a stirrer Reflux the system for 2.5 hours under N2

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

Procedure: Add 2 g of triethylene tetraamine (with an AV of approximately 1180 mg KOH/g) to 20 ml of toluene in a 250 ml flask fitted with a stirrer, condensor and nitrogen inlet. Add 4.82 g ethylene carbonate to the mixture. Reflux the system for 2.5 hours under N2. Strip the system to yield an ethylene carbonate-triethylene tetraamine adduct having an AV of approximately 250 mg KOH/g. fitted with a stirrer Reflux the system for 2.5 hours under N2

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

Procedure: Add 2 g of triethylene tetraamine (with an AV of approximately 1180 mg KOH/g) to 20 ml of toluene in a 250 ml flask fitted with a stirrer, condensor and nitrogen inlet. Add 4.82 g ethylene carbonate to the mixture. Reflux the system for 2.5 hours under N2. Strip the system to yield an ethylene carbonate-triethylene tetraamine adduct having an AV of approximately 250 mg KOH/g. fitted with a stirrer Reflux the system for 2.5 hours under N2