ESTERIFICATION

Esterification is a term used to describe the reaction of acids (especially organic or carboxylic acids) with alkanols (alcohols) to form alkanoates (esters) and water. Alkanoic acid + Alkanol Alkanoate (Ester) + Water Esterification reaction is a slow and reversible reaction when carried out at room temperature. The reverse reaction is simply hydrolysis, in that, Esters can also be hydrolysed to form alkanoic acids and alkanols. A proper understanding of esterification involves a simple knowledge of the nature of esters.

Esters
Esters are organic substances that are usually found in fats and oils. Some of them are known to confer unique pleasant smell to flowers and sweet flavours to fruits. Octyl ethanoate, CH3COOC8H17 smells like oranges; and pentyl ethanoate, CH3COOC5H11, has the odour of banana and is used as banana oil flavour. The structural formula of esters, RCOOR', is formed from carboxylic acid, RCOOH and Alkanol, HOR'. RCOOH + HO-R' RCOOR' + H2O That is, the R in the structure of the ester is donated by the carboxylic acid, and the R' is from the Alkanol. The water so formed from the reaction is a product of the hydroxyl group, -OH, of the carboxyl functional group, -COOH, and the hydrogen atom,H, of the hydroxyl functional group, -OH of the alkanol. It is important to say that, R and R' could either be the same or different alkyl or aryl groups. Simple examples of esters are ethyl ethanoate (CH3COOC2H5) with the same alkyl group and methyl ethanoate (CH3COOCH3) with different alkyl groups. The naming of an alkanoate is such that the alkyl group donated by the alkanol is named first before the

alkyl group donated by the carboxylic acid is named with "oate" replacing the "oic" of the carboxylic acid. It is also worthwhile to say that, esterification is essential to the production of Biodiesel. Here, the fatty acid component of oil is made to react with alcohol - especially, ethanol or methanol - in the presence of an alkali or acid catalyst to form the fatty acid ester.

Ethyl Ethanoate
Although esters differs in their degree of reactivity, it is comfortable to say that they are chemically similar compound. Small wonder, ethyl ethanoate can be used to present the chemical properties of esters. Preparation of Ethyl ethanoate Ethyl ethanoate is prepared by the esterification of glacial ethanoic acid and ethanol at 150C in the presence of concentrated tetraoxosulphate(VI) acid. C2H5OH(aq) + CH3COOH(l) CH3COOC2H5(l) + H2O(l) Hydrolysis of Ethyl Ethanoate Ethyl ethanoate can be hydrolysed to the component ethanoic acid and ethanol. Hydrolysis of ethyl ethanoate is carried out in the presence of either dilute acid or dilute alkali catalyst. The use of dilute alkali such as sodium hydroxide, NaOH, is associated with the initial formation of the salt of the acid, i.e. sodium ethanoate. CH3COOC2H5(l) + NaOH(aq) CH3COONa(aq) + C2H5OH(aq) Then, the sodium ethanoate is hydrolysed to sodium hydroxide and ethanoic acid, CH3COONa(aq) H2O(l) CH3COOH(l) + NaOH(aq) A point of note is that, the formation of the salt of the acid with alkali is applicable to saponification where fatty acids from oil are reacted with alkali to form soap. Reduction Reaction of Ethyl ethanoate Ethyl ethanoate is reduced to ethanol in the presence of strong reducing agents like lithium tetrahydridoaluminate(III). CH3COOC2H5(l) + 4[H] 2C2H5OH(l) Reaction with Ammonia

Amides are formed from the direct reaction of ammonia, NH3, with esters. Ethyl ethanoate forms ethanamide, CH3CONH2, when ammonia gas is bubbled through. CH3COOC2H5(l) + NH3(g) C2H5OH(l) + CH3CONH2(s)