Estolide derivatives useful as biolubricants
An acid anhydride and product technology, applied in the field of biological lubricant compositions, can solve problems such as not showing thermal oxidation stability
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[0030] The preparation of anhydride derivatives can be carried out starting from mixtures of hydroxylated fatty acids or fatty acid esters. It has surprisingly been found that, starting from such mixtures, anhydride derivatives can be prepared which exhibit advantageous properties, including a very low pour point, according to the process of the invention. Accordingly, the anhydride derivatives may be suitable for a wide range of applications, including those requiring properties at very low temperatures.
[0031] In some embodiments, the mixture of starting hydroxylated fatty acids or fatty acid esters comprises two or more hydroxylated C 1 -C 24 Fatty acids, or two or more hydroxylated C 1 -C 20 Fatty acids (or their esters). In some embodiments, the mixture comprises short chain hydroxylated fatty acids, such as hydroxylated C 1 -C 4 -COOH (or its esters) and long-chain hydroxylated fatty acids such as hydroxylated C 12 -C 20 -COOH (or its esters). In a preferred e...
Embodiment 1
[0060] Step 1: A glass reactor equipped with a temperature controller, overhead stirrer, and Dean-Stark apparatus was loaded with 12-hydroxy-stearic acid (450.4 grams (g)), lactic acid (37.1 g), 2-ethylhexanol ( 487.8g) and tin(II) 2-ethylhexanoate (1.9g). The mixture was then heated to 190°C for a period of 6 hours while removing water by fractional distillation. Excess 2-ethylhexanol was removed by distillation under reduced pressure at 160°C, and then the reactor was cooled to 120°C.
[0061] Step 2: To the product of Step 1 (584.7 g) was added tin(II) 2-ethylhexanoate (1.2 g). The mixture was heated to the set point temperature of 200° C. for a period of three hours with stirring. Excess 2-ethylhexanol was removed from the reactor contents by distillation under reduced pressure (20 mbar), and the reactor was then cooled to 120°C.
[0062]Step 3: To the product of Step 2 (466.2 g) was added isobutyric anhydride (120.4 g). The reactor was stirred at this temperature for ...
Embodiment 2
[0064] Step 1: A glass reactor equipped with a temperature controller, overhead stirrer and Dean-Stark apparatus was loaded with 12-hydroxy-stearic acid (407.0 g), lactic acid (67.6 g), 2-ethylhexanol (520.2 g) and tin(II) 2-ethylhexanoate (2.0 g). The mixture was heated to a set point temperature of 190°C and kept stirring for a period of 6 hours, water was removed by fractional distillation. Excess 2-ethylhexanol was removed by distillation under reduced pressure at 160°C, and then the reactor was cooled to 120°C.
[0065] Step 2: To the Step 1 product (565.8 g) was added tin(II) 2-ethylhexanoate (1.3 g) and the mixture was heated to a set point temperature of 200° C. for a period of three hours with stirring. 2-Ethylhexanol formed during the reaction was removed from the reactor contents by distillation under reduced pressure (20 mbar), and the reactor was then cooled to 120°C.
[0066] Step 3: To the product of Step 2 (445.0 g) was added isobutyric anhydride (144.3 g). ...
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