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Fatty ester compositions with improved oxidative stability

a technology of oxidative stability and composition, which is applied in the direction of liquid carbonaceous fuel, fatty substance preservation using additives, fuels, etc., can solve the problems of accelerating oxidative instability, and achieve the effect of easy dissolution

Inactive Publication Date: 2011-06-30
TAMINCO NV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

"The present invention relates to a composition that includes a fatty ester component, a nitroxide free-radical scavenger or precursor thereof, and an alkylalkanolamine. The nitroxide scavenger stops the oxidation process at the initiation stage, so less of this scavenger is needed and its effectiveness is not affected by the amount of oxygen present. The nitroxide scavenger is stable and not volatile, and it remains in the composition. The combination of the nitroxide scavenger with the alkylalkanolamine results in a synergistic effect on the oxidative stability of the composition. The nitroxide scavenger can be selected from the group consisting of 4-hydroxy-2,2,6,6-tetramethylpiperidino-1-oxy and 4-oxo-2,2,6,6-tetramethylpiperidino-1-oxy. The composition can also contain other additives such as nonphenolic oxygen scavengers, primary, secondary, or tertiary un-substituted or substituted amines, or phenolic oxygen scavengers. The method of making the stabilized composition involves blending together the fatty ester component, the nitroxide scavenger or precursor thereof, and the alkylalkanolamine."

Problems solved by technology

Continuation of this propagation stage is a chain reaction resulting in numerous hydroperoxides and fatty ester radicals leading to accelerated oxidative instability until the dissolved oxygen is consumed.
During the oxidation of hydroxylamines as used in US 2007 / 0137098 and in WO 2007 / 146567, reactive free radicals may also be formed, as an intermediary product, but these free radicals are only formed during the propagation stage and are not stable and react quickly away.

Method used

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  • Fatty ester compositions with improved oxidative stability
  • Fatty ester compositions with improved oxidative stability
  • Fatty ester compositions with improved oxidative stability

Examples

Experimental program
Comparison scheme
Effect test

example 1

Solubility Tests

[0068]a) An antioxidant package was prepared by dissolving 0.5 grams of 4-hydroxy TEMPO (4-HT) into 10 grams of octylaminoethanol (OAE). The nitroxide was completely soluble in the alkanolamine.

[0069]b) An antioxidant package was prepared by dissolving 0.5 grams of 4-HT along with 1 gram propyl gallate into 15 grams OAE. The nitroxide and ester of gallic acid were completely soluble in the alkanolamine.

[0070]c) An antioxidant package was prepared by dissolving 0.5 grams of 4-HT into 7.5 grams anhydrous diethylhydroxylamine (DEHA). The nitroxide was completely soluble in the hydroxylamine.

[0071]d) An antioxidant package was prepared by dissolving 0.5 grams of 4-HT into 7.5 grams anhydrous DEHA. Additionally, 2 grams of octyldiethanolamine (ODEA) was added to the additive mixture. The nitroxide and amine was completely soluble in the hydroxylamine.

example 2

Combination of ODEA or BDEA and 4-Hydroxy TEMPO

[0072]Use was made in this example of a pure soy-biodiesel (methyl ester of soy oil) from a commercial source having a Rancimat oxidative stability (tested in accordance with EN 14112) of 5.1 hours.

[0073]a) Addition of 50 ppm 4-HT increased the oxidative stability of this B100 biodiesel to 5.5 hours.

[0074]b) Addition of 450 ppm ODEA increased the oxidative stability of this B100 biodiesel to 8.3 hours.

[0075]c) Addition of 450 ppm ODEA plus 50 ppm 4-HT increased the oxidative stability test to 9.8 hours. Comparing Example 2a and Example 2b to this Example, it is easy to see the synergy that develops between ODEA and 4-HT.

[0076]d) Addition of 450 ppm BDEA to the soy methyl ester in Example 2a increased the oxidative stability test to 6.1 hours.

[0077]e) Addition of 475 ppm BDEA plus 25 ppm 4-HT to the soy methyl ester in Example 2a increased the oxidative stability test to 9.4 hours. Comparing Example 2a and Example 2d to this Example, it ...

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Abstract

Compositions containing unsaturated fatty esters may be stabilized against atmospheric oxidation by the addition of an antioxidant package containing at least one nitroxide free-radical scavenger and at least one alkylalkanolamine. Compositions treated in this manner show good resistance to atmospheric oxidation and resultant viscosity increase. An advantage of the nitroxide free-radical scavenger is that it stops the oxidation of the unsaturated fatty esters already during the initiation stage. Moreover, it is much less volatile than for example the known alkylhydroxylamine oxygen scavengers. By the use of a nitroxide free-radical scavenger, the composition can thus be stabilized for a longer period of time. The stability period is moreover less affected by the supply of oxygen to the composition. The solubility problem of the nitroxide in the fatty ester component can be solved by dissolving the nitroxide first in the alkylalkanolamine.

Description

[0001]The invention relates to fatty ester compositions. More particularly, it relates to fatty ester compositions that contain at least 50 wt % of a fatty ester component which comprises an unsaturated fatty ester and that contain moreover additives, including at least one alkylalkanolamine, that reduce their oxidative degradation.BACKGROUND OF THE INVENTION[0002]Fatty esters are widely used commercially in a variety of applications. Commonly used esters include natural fats and oils, especially triglyceride oils. Well known examples include soybean oil, rapeseed oil, jathropa oil, palm oil, canola oil, olive oil, linseed oil, and tung oil.[0003]Another important type of fatty ester is biodiesel, a clean-burning alternative fuel produced from domestic, renewable resources. Biodiesel contains no petroleum, but it can be blended at any level with petroleum diesel to create a fuel blend. It can be used in compression-ignition (diesel) engines with little or no modification. Biodiesel ...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C10L1/00C10L1/232C10L1/22C10L1/18
CPCC10L1/14C10L1/19C10L1/22C10L1/2225C11B5/005C10L1/232C10L1/2412C10L1/2425C10L1/23
Inventor MARTYAK, NICHOLAS M.ALFORD, DANIELDOWLING, CONOR M.GERNON, MICHAEL D.
Owner TAMINCO NV