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US 5,399,731 AGranted
Process for the production of fatty acid esters of lower alcohols
AssigneeVogel & Noot Industrieanlagenbau Gesellschaft m.b.H.
InventorTheodor Wimmer
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AssigneeVogel & Noot Industrieanlagenbau Gesellschaft m.b.H.
InventorTheodor Wimmer
Estimating the term…
The invention relates to a process for the production of the fatty acid esters of lower monovalent alcohols by transesterification of fatty acid glycerides in the presence of basic catalysts. The process according to the invention is characterized in that the transesterification is carried out in the presence of 0.025 to 0.045 mols of an alkali or alkaline earth metal compound, preferably sodium hydroxide, potassium hydroxide, sodium or potassium alcoholate, based on 100 g of fatty acid glyceride and the subsequent purification of the fatty acid esters is effected by the addition of 0.3 to 3.0 percent of water by hydration and separation of the catalyst residues and other impurities. In contrast to the known processes, it is thus possible to obtain lower alcohols of any given high degree of transesterification and high purity from untreated oils and fats of natural origin with contents of up to 20 percent of fatty acids in the free state at ambient temperature and atmospheric pressure at minor alcohol excess by means of the simplest equipment.
A process for the production of fatty acid esters of lower monovalent alcohols with 1 to 5 carbon atoms by transesterification of fatty acid glycerides with the lower monovalent alcohols in the presence of basic catalysts and at a reaction temperature of between 5.degree. C. and +40.degree. C., wherein based on each 100 g of fatty acid glyceride, at least 0.025 mols of a basic alkali or alkaline earth metal compound, plus that amount of the alkali or alkaline earth metal compound which is equivalent to the fatty acids in the free state contained in the fatty acid glycerides employed, are used as transesterification catalyst at an excess of the lower monovalent alcohol of 1.10 mols to 1.80 mols per mol of fatty acid esterified with glycerol, and that after completion of the transesterification, 0.1 to 5.0 percent of a diluted organic or inorganic acid or a diluted aqueous solution of an acid salt, based on the weight of the fatty acid ester, are added with stirring and fatty acid ester is separated as supernatant after settling of a heavy phase.
Dependencies are inferred from the claim text.
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Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom: by esterification of fatty acids with alcohols
Preparation of carboxylic acid esters: by reacting an ester group with a hydroxy group
Fatty acids from fats, oils or waxes
Acyclic or carbocyclic compounds
Term ended 21 Mar 2012 (estimated)
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The present invention relates to a process for the production of fatty acid esters and/or fatty acid ester mixtures of lower monovalent alcohols having 1 to 5 carbon atoms by transesterification of fatty acid glycerides with the lower alcohols in the presence of basic catalysts.
The fatty acid esters produced according to the invention are suitable depending on the starting materials used, for instance as pharmaceutical, dietetic or cosmetic raw materials, as diesel fuels, as fuel oils or as intermediate products for the production of further fatty acid derivatives such as fatty alcohols, tensides and the like as well as for the production of lubricants.
Due to their suitability as diesel fuels, fatty acid esters of this type have recently gained particular importance for reasons of environment protection, the replacement of fossil fuels by regenerable energy sources and the problems connected with agriculture.
The invention is explained in detail by means of the following examples:
A solution of 1.83 g (0.033 mols) of potassium hydroxide in 19 ml of methanol is added to 100 g of deslimed and deacidified (acid number 0.07) rapeseed oil and stirred in a beaker of 250 ml cubical content by means of a magnetic agitator for 15 minutes. After being left to stand for one hour, the glycerol phase accumulated on the bottom of the beaker is drawn off, e.g., by sucking up in a pipette. 0.5 l of water are added and stirring is continued for 10 minutes. After having been left standing for 12 hours, the supernatant is decanted. It consists of virtually pure rapeseed fatty acid methyl ester without any detectable fatty acid mono-, di- or triglycerides and an ash content of 0.004 percent.
In a container with a cubical capacity of 2000 liters equipped with an agitator and a discharge device in the bottom, 1618 kg of unrefined rapeseed oil with a content of 2.25 percent of fatty acids in the free state are charged. A solution of 27.8 kg of industrial grade potassium hydroxide (corresponding to 24.5 kg of 100 percent KOH) in 240 l of methanol is added and stirring is continued for 20 minutes. After a sedimentation period of three and one-half hours, the glycerol phase on the bottom of the container is drained off and stirring is resumed after the addition of a solution of 6.9 kg of industrial grade potassium hydroxide (corresponding to 6.1 kg of 100 percent KOH) in 60 l of methanol and continued for 20 minutes again. After that, 80 kg of water are immediately added and stirring is continued for another five minutes. After being left standing overnight, the heavy phase is drained off from the bottom of the container. The supernatant is suitable for use as a diesel fuel without any further treatment. It contains less than 1.5 percent residual fatty acid glycerides and 0.008 percent ash.