Methanol and ethanolThe simplest of all alcohols, methanol, has a boiling point of 148.5° F. (64.7° C). It was formerly known as wood alcohol. For centuries, it was obtained by heating wood to about 900° F. (about 500° C) in the absence of air and distilling off (purifying) the liquid formed. Today, the chief source of methanol is synthesis gas, a mixture of carbon monoxide and hydrogen. Nearly half the methanol manufactured is converted into methanal (formaldehyde), a starting material for phenolic resins, which are synthetic resins that harden and become permanently shaped under the continual application of heat. Other derivatives include ethanoic acid (acetic acid) and chloromethane (methyl chloride).
With a boiling point of 172° F. (78.3° 0, ethanol is a colorless liquid at room temperature. Its preparation by fermentation is an ancient process used over many centuries for producing alcoholic beverages. Until the arrival of the petrochemical industry, ethanol was prepared by fermenting plant-derived carbohydrates such as starch, sugar, or cellulose. Today, most industrial ethanol is prepared synthetically. The major industrial use for ethanol (about 45 per cent of all uses) is in the production of ethanal (acetaldehyde). Acetaldehyde is
Organic chemistry: Alcohols 81
A Esterification
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'■r^w'^r^r^^
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Alcohol (ethanol)
| Carboxylic acid (butanoic acid)
| Ester
(ethyl butanoate)
| Water
| B Saponification
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| a. I IP f
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Hydroxyl ion (from base)
| Ester
(ethyl butanoate)
| Alcohol (ethanol)
| Carboxylate ion (butanoate)
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---- ► #OMft
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• ~CH2
O =co
^ -OH
| Hydrogen ion (from acid)
| Carboxylate ion (butanoate)
| Carboxylic acid (butanoic acid)
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Two key reactionsof alcohols are esterification and saponification. Esterification (A) is the reaction between an alcohol and a carboxylic acid to form an ester and water. It is analogous to the neutralization of an acid by a base. Saponification (B) can be considered the reverse reaction. The action of a base on an ester followed by the addition of excess acid regenerates the original alcohol and acid.
used as a source of acetic acid, as a solid fuel (canned heat), and in the synthesis of many other compounds. About 30 per cent of the ethanol produced annually is used as a solvent. The rest is used in various chemical processes.
Date: 2015-12-11; view: 1733
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