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Estolide compositions exhibiting high oxidative stability

A composition and compound technology, applied in lubricating composition, organic chemistry, fatty acid esterification, etc., can solve problems such as insufficient hydrolytic stability and oxidation stability

Active Publication Date: 2014-03-05
BIOSYNTHETIC TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, naturally occurring fatty esters are often deficient in one or more areas, including hydrolytic stability and / or oxidative stability

Method used

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  • Estolide compositions exhibiting high oxidative stability
  • Estolide compositions exhibiting high oxidative stability
  • Estolide compositions exhibiting high oxidative stability

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0236] The acid catalyst reaction was performed in a 50 gallon Pfaudler RT-Series glass lined reactor. Oleic acid (65Kg, OL700, Twin Rivers) was charged to the reactor along with 70% perchloric acid (992.3mL, Aldrich Cat#244252) and the reaction was carried out under vacuum (10 Torr absolute (Torr absolute; 1 Torr = ~1mmHg)). Heat to 60°C for 24 hours with continuous stirring. After 24 hours, the vacuum was released. 2-Ethylhexanol (29.97 Kg) was then added to the reactor and vacuum restored. The reaction was continued for another 4 hours under the same conditions (60 °C, 10 absolute Torr). At this point KOH (645.58 g) was dissolved in 90% ethanol / water (5000 mL, 90 vol% EtOH) and added to the reactor to quench the acid. The solution was then allowed to cool for about 30 minutes. The contents of the reactor were then pumped through a 1 μm (μ) filter into a collector to filter out the salts. Water is then added to the collector to wash the oil. The two liquid phases were ...

Embodiment 2

[0238] The acid catalyst reaction was performed in a 50 gallon Pfaudler RT-Series glass lined reactor. Oleic acid (50Kg, OL700, Twin Rivers) and full fraction coconut oil fatty acid (18.754Kg, TRC110, Twin Rivers) were added to the reactor with 70% perchloric acid (1145mL, Aldrich Cat#244252) and heated under vacuum (10 Absolute Torr) to 60° C. for 24 hours with continuous stirring. After 24 hours, the vacuum was released. 2-Ethylhexanol (34.58 Kg) was then added to the reactor and vacuum restored. The reaction was continued for another 4 hours under the same conditions (60 °C, 10 absolute Torr). At this point KOH (744.9 g) was dissolved in 90% ethanol / water (5000 mL, 90 vol% EtOH) and added to the reactor to quench the acid. The solution was then allowed to cool for about 30 minutes. The contents of the reactor were then pumped through a 1 μ filter into the collector to filter out the salts. Water is then added to the collector to wash the oil. The two liquid phases wer...

Embodiment 3

[0240] The estolide prepared in Example 1 (Example 1) was subjected to distillation conditions at 300° C. in a Myers 15 centrifugal still at an absolute pressure of about 12 μm (0.012 Torr). This produced a primary distillate with a lower EN average (Example 3A) and a distillation bottom with a higher EN average (Example 3B). Certain data are reported in Tables 1 and 8 below.

[0241] Table 1

[0242] estolide base stock

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PUM

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Abstract

Provided herein are estolide compositions having high oxidative stability, said compositions comprising at least one compound of formula: (I) in which n is an integer equal to or greater than 0; m is an integer equal to or greater than 1; R1, independently for each occurrence, is selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; R2 is selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; and R3 and R4, independently for each occurrence, are selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched. Also provided herein are uses for the compositions and methods of preparing the same.

Description

[0001] Related Application Cross Reference [0002] This application claims U.S. Provisional Patent Application No. 61 / 498,499, filed June 17, 2011, U.S. Provisional Patent Application No. 61 / 569,046, filed December 9, 2011, and U.S. Provisional Patent Application No. 61 / 569,046, filed May 4, 2012 Benefit under 35 U.S.C. §119(e) of Application No. 61 / 643,072, which is hereby incorporated by reference in its entirety for all purposes. technical field [0003] The present disclosure relates to lubricating compositions comprising one or more estolide compounds and having high oxidation stability and methods for their preparation. Background technique [0004] Various commercial uses of fatty esters such as triglycerides are described. When used as lubricants, fatty esters, for example, can provide biodegradable alternatives to petroleum-based lubricants. However, naturally occurring fatty esters are often deficient in one or more areas, including hydrolytic stability and / or o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C10M169/04C07C69/675C11C3/00C10N30/10
CPCC11C3/08C10M2215/064C10N2220/027C10M2207/301C10M2207/044C11C1/10C10M133/04C10M2215/065C10M2207/024C10M2219/087C11C3/003C10N2230/10C10N2220/028C10N2220/025C10M2207/283C10M2223/045C10M105/32C10N2220/022C10N2270/00C10N2220/024C10M2207/026C10M169/04C10N2020/013C10N2020/065C10N2020/069C10N2020/071C10N2020/02C10N2030/10C10N2070/00C10N2010/04C10M105/36C07C69/675C10M129/10C10M133/12
Inventor J·布雷德瓜尔德T·汤普森J·弗雷斯特
Owner BIOSYNTHETIC TECH