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

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

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

Procedure: To a solution of 4-[3-(6-Bromo-hexyl)-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (5g, 10.60 mmol) in THF (100 mL), thiourea (0.889 g, 11.68 mmol) was added and heated to reflux overnight. According to HPLC analysis, the starting material was completely consumed. Tetraethylenepentamine (4.02 g, 2.7 mL, 21.23 mmol) was added and the reaction mixture was heated to reflux overnight. At this time, the reaction mixture was diluted with EtOAc (500 mL), washed with 3N HCl (100 mL), water brine and dried over Na2SO4. The solvent was removed in vacuo to afford an oil. FCC (2% EtOAc/Hex) provided an oil (3.65 g, yield 81%). 1H NMR (CDCl3): □ 7.09 (t, 1H), 6.75 (d, 1H), 6.69 (d, 1H), 4.18-4.08 (m, 4H), 3.99 (t, 2H), 2.95 (t, 2H), 2.64-2.46 (m, 8H), 2.13 (m, 2H), 1.67-1.39 (m, 8H), 1.27 (m, 6H). heated to reflux overnight the starting material was completely consumed the reaction mixture was heated to reflux overnight washed with 3N HCl (100 mL), water brine dried over Na2SO4 The solvent was removed in vacuo to afford an oil

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reaction product of isostearic acid (ISA) and tetraethylene pentamine (TEPA; Union Carbides HP TEPA) was prepared by adding 450 grams of isostearic acid to a 500 ml round bottom 4-neck flask equipped with a reflux condenser, a stirring bar and a nitrogen bubbler in order to obtain a level sufficient to permit agitation and heat transfer. The flask contents were then heated to 110° C. and 189 grams (about 1 mole) of TEPA were added slowly with mixing. After all of the TEPA was added to the flask, an additional 450 grams of ISA were added with stirring at 110° C. (a total of about 3.125 moles of ISA were added). The batch temperature was then raised slowly to drive the condensation reaction. Water of condensation began to appear immediately and was removed through the flask overhead system with a nitrogen sparge. After most of this water was removed (approximately 160° C.), vacuum stripping was applied and the flask temperature was raised to 200° C. to drive the condensation to completion. The reaction was complete after about 5 hours with 3 moles of isostearic acid (ISA) reacting with 1 mole of tetraethylene pentamine (TEPA) to form ISA-TEPA. The resulting product is designated friction modifier-1 (FM-1). equipped with a reflux condenser, a stirring bar a nitrogen bubbler in order to obtain a level sufficient heat transfer with mixing were added) The batch temperature was then raised slowly the condensation reaction was removed through the flask overhead system with a nitrogen sparge After most of this water was removed (approximately 160° C.), vacuum stripping the flask temperature was raised to 200° C. the condensation to completion

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

Procedure: To a 2 liter 4-necked reaction flask equipped with a stirrer, Dean Stark trap, condenser and nitrogen sparger were charged dodecylphenol (524 g, 2.0 m), trioxane (60 g, 0.66 m) and tetraethylene pentamine (TEPA) (189 g, 1.0 m). The temperature was raised slowly to 110° C. at which time water evolution began. After 8 hours the temperature had risen to 115° C. and water evolution ceased (42 cc's of water were collected). The mixture was cooled and filtered to yield 730g of a dodecylphenol-TEPA product containing 9.1% nitrogen. To a 2 liter 4-necked reaction flask equipped with a stirrer were collected) The mixture was cooled filtered

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: A vessel is charged with 102 parts of 126 neutral petroleum oil, 36 parts of a neutral calcium sulfonate (prepared by sulfonating a 480 neutral oil and neutralizing the sulfonic acid with sodium hydroxide followed by metathesis with calcium chloride) and 12 parts of a succinimide dispersant (prepared by reacting polyisobutene succinic anhydride with tetraethylene pentamine). The contents of the vessel are mixed, and thereafter there is added a mixture of 200 parts of water containing 119 parts of potassium borate (formed by reacting 52 parts of potassium hydroxide with 145 parts of boric acid). The contents are vigorously agitated to form a stable micro-emulsion of the aqueous phase within the petroleum oil. The emulsion is dehydrated at a temperature of 132° C. to yield a stable dispersion of partculate potassium triborate in the diluent oil. prepared The contents of the vessel are mixed there is added is dehydrated at a temperature of 132° C.

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

Procedure: A vessel is charged with 102 parts of 126 neutral petroleum oil, 36 parts of a neutral calcium sulfonate (prepared by sulfonating a 480 neutral oil and neutralizing the sulfonic acid with sodium hydroxide followed by metathesis with calcium chloride) and 12 parts of a succinimide dispersant (prepared by reacting polyisobutene succinic anhydride with tetraethylene pentamine). The contents of the vessel are mixed, and thereafter there is added a mixture of 200 parts of water containing 119 parts of potassium borate (formed by reacting 52 parts of potassium hydroxide with 145 parts of boric acid). The contents are vigorously agitated to form a stable micro-emulsion of the aqueous phase within the petroleum oil. The emulsion is dehydrated at a temperature of 132° C. to yield a stable dispersion of partculate potassium triborate in the diluent oil. prepared The contents of the vessel are mixed there is added is dehydrated at a temperature of 132° 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:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add 37.8 g of tetraethylene pentaamine (with an AV of approximately 1050 mg KOH/g) to a 250 ml flask fitted with a stirrer, condensor and nitrogen inlet. Add 52.6 g ethylene carbonate to the system. Heat the system at 160° C. for 3 hours under N2. Strip the system to yield an ethylene carbonate-triethylene tetraamine adduct having an AV of approximately 180 mg KOH/g. fitted with a stirrer

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add 37.8 g of tetraethylene pentaamine (with an AV of approximately 1050 mg KOH/g) to a 250 ml flask fitted with a stirrer, condensor and nitrogen inlet. Add 52.6 g ethylene carbonate to the system. Heat the system at 160° C. for 3 hours under N2. Strip the system to yield an ethylene carbonate-triethylene tetraamine adduct having an AV of approximately 180 mg KOH/g. fitted with a stirrer