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Transesterification

Transesterification is a process that involves reacting triglycerides with an alcohol like ethanol in the presence of a catalyst, usually a strong base, to produce esters of fatty acids known as biodiesel and glycerol. It is a reversible reaction, so alcohol is used in excess to drive the reaction towards completion. The base deprotonates the alcohol, making it a stronger nucleophile that can attack the carbonyl carbon of the triglyceride, replacing the fatty acid chains in a series of steps to form biodiesel and glycerol. Proper control of factors like catalyst amount, alcohol-to-oil ratio, temperature, and moisture content is needed to maximize conversion to

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220 views

Transesterification

Transesterification is a process that involves reacting triglycerides with an alcohol like ethanol in the presence of a catalyst, usually a strong base, to produce esters of fatty acids known as biodiesel and glycerol. It is a reversible reaction, so alcohol is used in excess to drive the reaction towards completion. The base deprotonates the alcohol, making it a stronger nucleophile that can attack the carbonyl carbon of the triglyceride, replacing the fatty acid chains in a series of steps to form biodiesel and glycerol. Proper control of factors like catalyst amount, alcohol-to-oil ratio, temperature, and moisture content is needed to maximize conversion to

Uploaded by

Jean-Marc Pierre
Copyright
© Attribution Non-Commercial (BY-NC)
Available Formats
Download as DOCX, PDF, TXT or read online on Scribd
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Transesterification

Triglycerides (1) are reacted with an alcohol such as ethanol (2) to give ethyl esters of fatty acids (3) and glycerol (4):

Animal and plant fats and oils are typically made of triglycerides which are esters containing three free fatty acids and the trihydric alcohol, glycerol. In the transesterification process, the alcohol is deprotonated with a base to make it a stronger nucleophile. Commonly, ethanol or methanol are used. As can be seen, the reaction has no other inputs than the triglyceride and the alcohol. Normally, this reaction will proceed either exceedingly slowly or not at all. Heat, as well as an acid or base are used to help the reaction proceed more quickly. It is important to note that the acid or base are not consumed by the transesterification reaction, thus they are not reactants but catalysts. Almost all biodiesel is produced from virgin vegetable oils using the base-catalyzed technique as it is the most economical process for treating virgin vegetable oils, requiring only low temperatures and pressures and producing over 98% conversion yield (provided the starting oil is low in moisture and free fatty acids). However, biodiesel produced from other sources or by other methods may require acid catalysis which is much slower.[5] Since it is the predominant method for commercial-scale production, only the base-catalyzed transesterification process will be described below. An example of the transesterification reaction equation, shown in skeletal formulas:

Since natural oils are typically used in this process, the alkyl groups of the triglyceride are not necessarily the same. Therefore, distinguishing these different alkyl groups, we have a more accurate depiction of the reaction:

R1, R2, R3 : Alkyl group. During the esterification process, the triglyceride is reacted with alcohol in the presence of a catalyst, usually a strong alkali (NaOH, KOH, or Alkoxides). The main reason for doing a titration to produce biodiesel, is to find out how much alkaline is needed to completely neutralize any free fatty acids present, thus ensuring a complete transesterification. Empirically 6.25 g / L NaOH produces a very usable fuel. One uses about 6 g NaOH when the WVO is light in colour and about 7 g NaOH when it is dark in colour. The alcohol reacts with the fatty acids to form the mono-alkyl ester (or biodiesel) and crude glycerol. The reaction between the biolipid (fat or oil) and the alcohol is a reversible reaction so the alcohol must be added in excess to drive the reaction towards the right and ensure complete conversion.

Base-catalysed transesterification mechanism


The transesterification reaction is base catalyzed. Any strong base capable of deprotonating the alcohol will do (e.g. NaOH, KOH, Sodium methoxide, etc.). Commonly the base (KOH, NaOH) is dissolved in the alcohol to make a convenient method of dispersing the otherwise solid catalyst into the oil. The ROH needs to be very dry. Any water in the process promotes the saponification reaction, thereby producing salts of fatty acids (soaps) and consuming the base, and thus inhibits the transesterification reaction. Once the alcohol mixture is made, it is added to the triglyceride. The reaction that follows replaces the alkyl group on the triglyceride in a series of steps. The carbon on the ester of the triglyceride has a slight positive charge, and the carbonyl oxygens have a slight negative charge. This polarization of the C=O bond is what attracts the RO- to the reaction site. Transesterification of Vegetable Oils In the transesterification of vegetable oils, a triglyceride reacts with an alcohol in the presence of a strong acid or base, producing a mixture of fatty acids alkyl esters and glycerol25,26 (Scheme 4). The overall process is a sequence of three consecutive and reversible reactions, in which diand

monoglycerides are formed as intermediates26. The stoichiometric reaction requires 1 mol of a triglyceride and 3 mol of the alcohol. However, an excess of the alcohol is Used to increase the yields of the alkyl esters and to allow Its phase separation from the glycerol formed. Several aspects, including the type of catalyst (alkaline or acid), alcohol/vegetable oil molar ratio, temperature, purity of the reactants (mainly water content) and free fatty acid content have an influence on the course of the transesterification and will be discussed below, based on the type of catalyst used.

General Aspects of Transesterification Transesterification is the general term used to describe the important class of organic reactions where an ester is transformed into another through interchange of the alkoxy moiety. When the original ester is reacted with an alcohol, the transesterification process is called alcoholysis (Scheme 1)1. In this review, the term transesterification will be used as synonymous for alcoholysis of carboxylic esters, in agreement with most publications in this field. The transesterification is an equilibrium reaction and the transformation occurs essentially by mixing the reactants. However, the presence of a catalyst (typically a strong acid or base) accelerates considerably the adjustment of the equilibrium. In order to achieve a high yield of the ester, the alcohol has to be used in excess. The applicability of transesterification is not restricted to laboratory scale. Several relevant industrial processes use this reaction to produce different types of compounds1. An example is the production of PET (polyethylene terephthalate), which involves a step where dimethylterephthalate is transesterified with ethylene glycol in the presence of zinc acetate as catalyst (Scheme 2)2. Furthermore, a large number of acrylic acid derivatives is produced by transesterification of methyl acrylate with different alcohols, in the presence of acid catalysts3-6. If the alcohol and the ester groups are present in the same molecule simple lactones7,8 or macrocycles9-10 are formed by an intramolecular transesterification, as shown found in the literature, in which metal alkoxides11-16, aluminum isopropoxide17-19, tetraalkoxytitanium compounds2022 and organotin alkoxides23,24 are applied as Catalysts.

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