MadSci Network: Chemistry
Query:

Re: Diethyl Ether Synthesis (see comments section for question)

Date: Sun Feb 6 16:33:36 2000
Posted By: John Lyga, Staff, Chemistry, FMC Corp.
Area of science: Chemistry
ID: 948657290.Ch
Message:

Montgomery;
You are right that the commercial synthesis of diethyl ether 
(CH3CH2OCH2CH3) involves the dehydration of ethanol (or ethyl alcohol, 
CH3CH2OH) usually with sulfuric acid (H2SO4).  The word dehydration means 
to remove water.  To produce one molecule of diethyl ether, you need to 
start with two molecules of ethanol and remove one molecule of water. The 
reaction is summarized below;

CH3CH2OH + CH3CH2OH  -------->   CH3CH2OCH2CH3 + H2O

The sulfuric acid helps remove the water which comes from the OH of one 
ethanol molecule and the H of the second ethanol molecule.  This type of 
reaction is in equilibrium; that means that both the starting material,  
ethanol, and products, diethyl ether and water, are all present. In fact, 
if you mix ethanol with a small amount of sulfuric acid; only a very small 
percentage will be converted into diethyl ether. The equilibrium lies to 
the left.  To force all of the ethanol to react, something has to be done 
to shift the equilibrium to the right.  The most common way to make the 
reaction work is to remove the diethyl ether as it is formed, usually by 
distilling it away from the reaction. Diethyl ether has a lower boiling 
point than either ethanol or water.  If you followed this discussion, you 
can probably answer your own question.  If you start with diluted ethanol 
and sulfuric acid, you have two problems, first the excess water shifts 
the equilibrium way to the left and second, the dilluted sulfuric acid is 
hydrated by the water and is not a good dehydration catalyst. 





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