Branched diesters for use to reduce the fuel consumption of an engine
An engine, automotive engine technology, applied in the direction of base materials, lubricating compositions, additives, etc., can solve problems such as component damage, lubricating composition failure, etc.
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Embodiment 1
[0117] Example 1 - Caprylic acid (octanoic acid)
[0118] C8:0 / 2-EH-9-DA
[0119] 2-Ethylhexyl-9-decenoate (≥98%, 200 g, 0.708 mol) and octanoic acid (Sigma Aldrich, ≥98%) were treated with triflic acid (Sigma Aldrich, 98%, 10 g, 0.067 mol) , 306g, 2.12mol) mixture. The mixture was stirred at 60°C for 18 hours. The mixture was cooled to 25 °C and washed with 3 x 100 mL saturated aqueous sodium bicarbonate and 100 mL brine. The organic phase was dried over magnesium sulfate and filtered. The product was recovered by vacuum distillation at 210°C-220°C, 2 Torr; light fractions and bottoms were discarded. The precipitate was removed by vacuum filtration through a sintered funnel to give 103 g of a colorless oil. Physical properties are reported as follows: kinematic viscosity (KV) at 100°C 3.24 cSt, KV at 40°C 12.02 cSt, viscosity index (VI) 143, pour point <-45°C, NOACK volatility 15 wt%.
[0120] In a particular aspect, the diester is represented by the structure
[0121]...
Embodiment 2
[0125] Example 2 - capric acid (decanoic acid)
[0126] C10:0 / 2-EH-9-DA
[0127] 2-Ethylhexyl-9-decenoate (≥98%, 400 g, 1.42 mol) and capric acid (Aldrich, ≥98%, 489 g, 2.83 mol) were treated with trifluoromethanesulfonic acid (20 g, 0.133 mol) mixture. The mixture was stirred at 60°C for 20 hours. The mixture was cooled to 25°C and quenched with 150 ml 1M KOH, which resulted in the formation of a precipitate. Water was added to the mixture and stirred vigorously. The resulting emulsion was transferred to a separation vessel and the phases were separated. The mixture was washed successively with 5 x 150 mL H2O. The product was recovered by vacuum distillation at 225°C, 2 Torr; the light fraction and bottoms were discarded. Distillation gave 223.1 g of product as a mixture of isomers with a purity of 99% by GC-FID. Physical properties are reported as follows: KV at 100°C 3.6 cSt, KV at 40°C 14.1 cSt, VI 145, pour point <-45°C, NOACK volatility 10 wt%.
[0128] C10:0 / 2...
Embodiment 3
[0130] Example 3 - Lauric Acid
[0131] C12:0 / 2-Ethylhexyl-9-decenoate
[0132]A mixture of 2-ethylhexyl-9-decenoate (≥98%, 200g, 0.708mol) and dodecanoic acid (SigmaAldrich, ≥98%, 425g, 2.12mol) was heated to 60°C, and then Treated with fluoromethanesulfonic acid (SigmaAldrich, ≥98%, 10 g, 0.067 mol). The reaction was stirred at 60 °C for 22 hours. The reaction mixture was then cooled to 45 °C and 100 mL of hexane was added. The contents of the reaction vessel were transferred to a dropping funnel and dodecanoic acid was recrystallized from solution by adding the mixture dropwise to isopropanol at -20°C. The resulting suspension was vacuum filtered through Whatman 6 filter paper. The filtrate was concentrated in vacuo and the oil was washed with 0.1M K 2 CO 3 Wash with aqueous solution until pH 7, then with water. Na for organic phase 2 SO 4 Drying followed by purification by vacuum distillation at 218°C, 0.1 Torr gave 69 g of an oil. Pass distillate through Al 2...
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