Process for the production of fatty acid lower alkyl esters

Details Process for the production of fatty acid lower alkyl esters Process for the production of fatty acid lower alkyl esters

1994-01-10

1995-10-03

Dees, Jose G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Fatty compounds having an acid moiety which contains the...

C11C 300

Patent

active

054553709

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP 92/01463 filed Jun. 29, 1992.


FIELD OF THE INVENTION

This invention relates to a process for the production of fatty acid lower alkyl esters by transesterification of fatty acid glycerides with lower aliphatic alcohols in the presence of free fatty acids.


PRIOR ART

Fatty acid methyl esters are important industrial raw materials for the production of a number of products, for example lubricants and surfactants. The esters are normally produced from natural fats and oils, i.e. full or partial esters of glycerol with fatty acids, which are transesterified with methanol in the presence of catalysts. Processes for the transesterification of fats and oils are described in a number of publications. The synoptic article in Seifen-Ole-Fette-Wachse, 114, 595 (1988) is cited here as representative of those publications.
If the transesterification is to be carried out with satisfactory conversions in an economically worthwhile time, catalysts have to be used. Suitable catalysts are, in particular, heavy metal compounds, such as for example zinc oxide [GB 712,747] and zinc silicate [U.S. Pat. No. 2,727,049]. However, processes of this type are attended by the disadvantage that, for toxicological reasons, the catalysts cannot remain in the product after transesterification, but instead have to be removed at considerable cost.
The transesterification may also be carried out in the presence of mineral acids which merely have to be neutralized on completion of the reaction. Although the problem of removal does not arise in this case, the volume/time yields of transesterification products are distinctly poorer by comparison with heavy metal catalysis; this is an obstacle to industrial application of the process.
Accordingly, the problem addressed by the present invention was to provide a process for the transesterification of fatty acid glycerides which would be free from the disadvantages mentioned above.


DESCRIPTION OF THE INVENTION

This invention relates to a process for the production of fatty acid lower alkyl esters by transesterification of fatty acid glycerides in the presence of acidic catalysts, characterized in that full and/or partial esters of glycerol with fatty acids corresponding to formula (I): carbon atoms and 0 or 1 to 5 double bonds, elevated temperature and, optionally, elevated pressure in the presence of at least one fatty acid corresponding to formula (II): carbon atoms and 0, 1 or 2 double bonds.
It has surprisingly been found that the transesterification of fatty acid glycerides in the presence of fatty acids leads to volume/time yields of transesterification products which, hitherto, could only be achieved in the presence of heavy metal compounds. Another advantage of the process according to the invention is that, on completion of the transesterification, the fatty acid is also present as an ester so that there is no need for removal or neutralization of the catalyst. In addition, production stoppages attributable to catalyst deposits can be reduced and contamination of the glycerol released and of the wastewater by heavy metal traces can be avoided.
Suitable starting materials for transesterification by the process according to the invention are both full esters and partial esters of glycerol with fatty acids; triglycerides are preferably used. Typical examples are glycerol esters of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, elaidic acid, petroselic acid, linoleic acid, linolenic acid, chaulmoogric acid, ricinoleic acid, arachic acid, gadoleic acid, behenic acid, erucic acid, arachidonic acid and clupanodonic acid.
The glycerol esters of the fatty acids mentioned above may be both synthetic and natural products, particularly those in which the glycerol is attached to two or three different fatty acids. Natural glycerol fatty acid esters are understood to be fats and oils of animal or vegetable origin, for example coconut oil, palm oil, palm kernel oil, peanut oil, co

REFERENCES:
patent: 2727049 (1955-12-01), Braconier et al.
patent: 4608202 (1986-08-01), Lepper et al.

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