Ethyl Acetate Polarity

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A specialized industrial route entails the catalytic dehydrogenation of ethanol. This method is more cost effective than the esterification but is applied with surplus ethanol in a chemical plant. Typically, dehydrogenation is conducted with copper at an elevated temperature but below 250 °C. The copper may have its surface area increased by depositing it on zinc, promoting the growth of snowflake-like fractal structures (dendrites). Surface area can be again increased by deposition onto a zeolite, typically ZSM-5. Traces of rare-earth and alkali metals are beneficial to the process. Byproducts of the dehydrogenation include diethyl ether, which is thought to arise primarily due to aluminum sites in the catalyst, acetaldehyde and its aldol products, higher esters, and ketones. Separations of the byproducts are complicated by the fact that ethanol forms an azeotrope with water, as does ethyl acetate with ethanol and water, and methyl ethyl ketone (MEK, which forms from 2-butanol) with both ethanol and ethyl acetate. These azeotropes are broken by pressure swing distillation or membrane distillation.