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REMOVAL OF PEROXIDES FROM FATTY ACID METHYL ESTERS BY THERMAL TREATMENT

IP.com Disclosure Number: IPCOM000168054D
Publication Date: 2008-Feb-28
Document File: 1 page(s) / 19K

Publishing Venue

The IP.com Prior Art Database

Abstract

Unsaturated fatty acid esters (e.g. methyl esters) generate peroxides upon exposure to air. The peroxides, in turn, oxidize components of hydroformylation catalysts and generate decomposition products that effectively poison hydroformylation catalysts. Minimize, preferably eliminate, decomposition product generation, by subjecting the unsaturated fatty acid esters to thermal treatment, especially in the absence of an oxygen source, before initiating hydroformylation.

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REMOVAL OF PEROXIDES FROM FATTY ACID METHYL ESTERS BY THERMAL TREATMENT

Unsaturated fatty acid esters (e.g. methyl esters) or triglycerides, especially esters or natural oils of multiply unsaturated fatty acids, such as soybean oil, sunflower oil, and linseed oil, and others, generate peroxides upon exposure to air.  The peroxides oxidize components of hydroformylation catalysts and generate oxidation decomposition products that are, at best, no longer useful as hydroformylation catalysts, and may even interfere with catalyst recovery.  This is particularly an issue with phosphine ligand portions of such catalysts.

In order to minimize, preferably eliminate, oxidation decomposition product generation, it is beneficial to subject the unsaturated fatty acid esters or triglycerides to thermal treatment, especially in the absence of an oxygen source, before initiating hydroformylation.  Thermal treatment constitutes a combination of exposure to elevated temperature and time at elevated temperature.  Reactor design (e.g. batch, plug-flow, continuous stir tank reactors) will have significant impact on the time and temperature required.  Temperatures of 170ºC and a time of 0.25 hour or more lead to markedly reduced peroxide contents, e.g. more than a 50% reduction at 0.25 hour and up to nearly a 100% reduction at 1 hour or more.  Increasing temperature to, for example 200ºC, further reduces peroxide content and time ne...