Q23P. Question. Cellosolve庐 is the tr... [FREE SOLUTION]

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Chapter 20: Q23P. (page 1038)

Question. Cellosolve^庐 is the trade name for 2-ethoxyethanol, a common industrial solvent. This compound is produced in chemical plants that use ethylene as their only organic feedstock. Show how you would accomplish this industrial process.

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Production of Cellosolve^庐

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Cellosolve®

Cellosolve or 2-ethoxyethanol is used to dissolve oils, resins and waxes. It is also used in varnish removers and dry-cleaning solutions.It is a common industrial solvent and is manufactured by ethylene oxide and ethanol reactions.

Preparation of cellosolve

Acidic hydrolysis of ethylene produces ethanol, and ethylene oxide is produced in large quantities from ethylene and oxygen using a metal catalyst. Peroxyacid can also be used to produce ethylene oxide, but the method is expensive. Ethanol and ethylene oxide react together under acidic conditions to produce cellosolve. Ethylene oxide is a strained molecule. After proton abstraction by oxygen, oxygen acquires a positive charge and strain on the ring further increases; thus, the ring opens up, and carbocation is formed at which ethanol attacks, which leads to the formation of 2-ethoxyethanol.