Synthesis of biolubricant esters from unsaturated fatty acid derivatives

a technology of unsaturated fatty acid and biolubricant, which is applied in the direction of fatty acid chemical modification, organic chemistry, lubricant composition, etc., can solve the problems of general compromising the oxidation stability of the lubricant composition

Inactive Publication Date: 2011-01-13
CHEVROU USA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Additionally still, as opposed to conventional biolubricants, i.e., triglycerides, the diester-based lubricants described herein have, in at least some embodiments, excell

Method used

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  • Synthesis of biolubricant esters from unsaturated fatty acid derivatives
  • Synthesis of biolubricant esters from unsaturated fatty acid derivatives
  • Synthesis of biolubricant esters from unsaturated fatty acid derivatives

Examples

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example 1

[0076]This Example serves to illustrate synthesis of mono-unsaturated fatty alcohol 11, in accordance with some embodiments of the present invention, and en route to the formation of isomeric diester mixture 4a / 4b. Referring to Scheme 3 (FIG. 5) oleic acid 7 was reduced to the corresponding oleoyl alcohol 11 (Step 501) as follows.

[0077]To an ice-cold (i.e., in an ice bath) suspension of 43 grams (1.13 mol) of lithium aluminum hydride (LiAlH4) in tetrahydrofuran (THF) in a 3-neck 3-liter reaction flask fitted with an overhead stirrer and a reflux condenser, 150 grams (0.53 mol) of oleic acid 7 was added drop-wise over a period of 45 minutes via an addition funnel. The resulting reaction mixture was allowed to warm gradually to room temperature, after which the ice bath was replaced with a heating mantle and the reaction mixture was refluxed for 4 hours. After refluxing, the reaction mixture was allowed to cool to room temperature and left to stir overnight. The reaction progress was ...

example 2

[0078]This Example serves to illustrate the synthesis of epoxy-alcohol species 12 (oleoyl epoxide), en route to the synthesis of isomeric diester mixture 4a / 4b and in accordance with some embodiments of the present invention. Referring again to Scheme 3 (FIG. 5), epoxy-alcohol species 12 was prepared from oleoyl alcohol 11 (Step 502) according to the following procedure.

[0079]To an ice-cold (ice-bath) solution of 52 grams of 75 wt % mCPBA (meta-chloro-peroxybenzoic acid) in 300 mL of methylene chloride (CH2Cl2) in a 3-neck 1L reaction flask, 50 grams of olcoyl alcohol 11, prepared as described above in Example 1, was added drop-wise over a 45 minute period. The reaction was allowed to slowly warm to room temperature, after which it was left to stir overnight at room temperature. The following day, the reaction mixture (solids+clear liquid) was filtered. The filtrate was rinsed once with 150 mL of 10 wt % NaSO3 aqueous solution, once with 200 mL of saturated KHCO3 solution, and three...

example 3

[0080]With continued reference to Scheme 3 (FIG. 5), this Example serves to illustrate how the epoxy-alcohol species 12 is converted (reduced) to an isomeric mixture of diol species 9a / 9b (Step 503), in accordance with some embodiments of the present invention. Isomeric mixture 9a / 9b was prepared according to the procedure that follows.

[0081]To an ice-cold suspension of 20 grams of LiAlH4 in 350 mL THF in 3-neck 2 L reaction flask (fitted with a reflux condenser and an overhead stirrer), 46 grams of epoxy alcohol 12 (synthesized as described above in Example 2 and dissolved in 200 mL of THF) were added drop-wise over a 30 minute period. The resulting mixture was left to warm to room temperature and then heated to reflux for few hours. The reaction was then allowed to stir at room temperature overnight. The next day, the reaction was placed in an ice-bath and diluted with 300 mL of ether. The ice-cold reaction mixture was treated by slowly adding 200 mL of 15 wt % NaOH solution follo...

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Abstract

The present invention is generally directed to diester-based lubricant compositions comprising one or more isomeric mixtures of diester species. The present invention is also directed to methods of making these and other similar lubricant compositions. In some embodiments, the methods for making such diester-based lubricants utilize a biomass precursor material from which mono-unsaturated free lipid species can be provided or otherwise generated, wherein such mono-unsaturated free lipid species arc converted to isomeric diol species en route to the synthesis of diester species for use as/in the diester-based lubricant compositions.

Description

FIELD OF THE INVENTION[0001]This invention relates to ester-based lubricants, and specifically to diester-based lubricants and their manufacture—particularly wherein they are made from at least one biologically-derived precursor.BACKGROUND[0002]Esters have been used as lubricating oils for over 50 years. They arc used in a variety of applications ranging from jet engines to refrigeration. In fact, esters were the first synthetic crankcase motor oils in automotive applications. However, esters gave way to polyalphaolefins (PAOs) due to the lower cost of PAOs and their formulation similarities to mineral oils. In full synthetic motor oils, however, esters are almost always used in combination with PAOs to balance the effect on seals, additives solubility, volatility reduction, and energy efficiency improvement by enhanced lubricity.[0003]Ester-based lubricants, in general, have excellent lubrication properties due to the polarity of the ester molecules of which they are comprised. The...

Claims

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Application Information

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IPC IPC(8): C10M129/72
CPCC07C29/132C07C29/147C07C67/08C10M105/38C10M2207/2835C10N2270/00C11C3/00C11C3/12C07C31/20C07C69/28C10N2070/00
Inventor ELOMARI, SALEH A.MILLER, STEPHEN JOSEPHZHOU, ZHEN
Owner CHEVROU USA INC
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