16-methylheptadecanoic acid

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:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: About 28.1 g (0.1 mole) of isostearic acid and 23.5 g (0.1 mol) of the CL-THAM adduct of Example 4 were added to a reaction flask and heated to 180° C. to distill off the water of reaction. The reaction mixture was heated at 180° C. for four hours with mild nitrogen sparging. An infrared analysis of the product showed the desired ester oxazoline. The residue was diluted in solvent 150 neutral mineral oil to make a 50% active ingredient solution and was collected. to distill off the water of reaction The reaction mixture was heated at 180° C. for four hours with mild nitrogen sparging was collected

Conditions: temp:117.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: About 780 grams of isostearic acid (acid number=194.4), 1 gram of p-toluenesulfonic acid were charged to a flask equipped with a heating mantle, stirrer, sub-surface inlet tube with a nitrogen purge and a condenser. The contents of the flask were heated under nitrogen flow to 117° C. About 400 grams of methanol were then added via the sub-surface inlet tube over 3.5 hours (acid number=9.6), 200 grams of additional methanol were added and the reaction continued for another 1.5 hours to obtain a final acid number of 0.6. equipped with a heating mantle, stirrer, sub-surface inlet tube with a nitrogen purge About 400 grams of methanol were then added via the sub-surface inlet tube over 3.5 hours (acid number=9.6), 200 grams of additional methanol were added

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

Procedure: Calcium isostearate was prepared from isostearic acid and calcium hydroxide rather than from sodium isostearate and calcium chloride.

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

Procedure: Calcium isostearate was prepared from isostearic acid and calcium hydroxide rather than from sodium isostearate and calcium chloride.

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

Procedure: Isostearoyl chloride, prepared from 20 g isostearic acid, 10.1 g thionyl chloride and 0.2 ml dimethyl formamide, according to the procedure of Example 1, is added to 11 g (0.09 mole) n-octylamine and 10 g. (0.10 mole) triethylamine in 100 ml ether. The reaction mixture is treated in accordance with the procedure of Example 2, yielding 22 g of an amber oil which exhibits infrared spectra values typical of a secondary amide. The reaction mixture is treated in accordance with the procedure of Example 2

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

Procedure: Isostearoyl chloride, prepared from 20 g isostearic acid, 10.1 g thionyl chloride and 0.2 ml dimethyl formamide, according to the procedure of Example 1, is added to 11 g (0.09 mole) n-octylamine and 10 g. (0.10 mole) triethylamine in 100 ml ether. The reaction mixture is treated in accordance with the procedure of Example 2, yielding 22 g of an amber oil which exhibits infrared spectra values typical of a secondary amide. The reaction mixture is treated in accordance with the procedure of Example 2

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

Procedure: 284.5 g of isostearic acid (molecular weight: 284.49, 1.00 mol) and thionyl chloride (molecular weight: 118.97, 1.05 mol) were placed in a 1-L reaction flask equipped with a thermometer. The mixture was stirred at room temperature for 20 minutes and then, heated at an oil bath temperature of 40° C. and stirred for 1 hour. The reaction solution obtained was left under reduced pressure for removal of the dissolved gas and excess thionyl chloride. 300 ml of toluene and 156.3 g of 1-menthol (molecular weight: 156.27, 1.00 mol) were added thereto; and 121.4 g of triethylamine (molecular weight: 101.19, 1.20 mol) was added dropwise over 20 minutes. After dropwise addition, the mixture was stirred at an oil bath temperature of 60° C. for 3 hours. The reaction solution obtained was quenched in water and extracted with toluene. The toluene phase was washed with aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and condensed in rotary evaporator for removal of the solvent to give yellow oil. Distillation thereof under reduced pressure gave a desired product, isostearic acid-1-menthyl as colorless oil. Yield: 351.4 g, (molecular weight: 422.7, 831.4 mmol), purity: 99.8%, yield: 83.1%. equipped with a thermometer heated at an oil bath temperature of 40° C. stirred for 1 hour The reaction solution obtained After dropwise addition the mixture was stirred at an oil bath temperature of 60° C. for 3 hours The reaction solution obtained was quenched in water extracted with toluene The toluene phase was washed with aqueous saturated sodium chloride solution dried over anhydrous sodium sulfate filtered condensed in rotary evaporator for removal of the solvent to give yellow oil Distillation

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: Into an apparatus similar to that in Example 1, were charged 103.1 g (1 mole) of diethylenetriamine and 284.5 g (1 mole) of isostearic acid. At 200° to 210° C., 18 g of water was distilled off to effect the monoamide formation. Then, after the addition of 130.1 g (1 mole) of ethyl acetoacetate, 18 g of water and 46 g of ethanol were distilled off at 150° to 160° C. to obtain 4-isostearamidoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one. At 200° to 210° C., 18 g of water was distilled off were distilled off at 150° to 160° C.

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 32 g (0.1 mole) of isostearic acid there is added 0.3 ml (0.002 mole) of triethylamine. The resulting mixture is heated to 130° C. under a nitrogen atmosphere and there are slowly added thereto 40 g (0.1 mole) of 2-octyl dodecyl ether of glycidyl obtained according to the above method. After heating for 3 hours and 15 minutes at 130° C., the amount of the reaction determined by acid index is 93%. there are slowly added

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

Procedure: Into an apparatus similar to that in Example 1, were charged 103.1 g (1 mole) of diethylenetriamine and 284.5 g (1 mole) of isostearic acid. At 200° to 210° C., 18 g of water was distilled off to effect the monoamide formation. Then, after the addition of 130.1 g (1 mole) of ethyl acetoacetate, 18 g of water and 46 g of ethanol were distilled off at 150° to 160° C. to obtain 4-isostearamidoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepin-5-one. At 200° to 210° C., 18 g of water was distilled off were distilled off at 150° to 160° C.