Sciencemadness Discussion Board

Preparation of Chloroethane

khourygeo77 - 18-1-2018 at 11:09

Is it that simple?

Pouring ~absolute Sulfuric acid on Nacl. Hydrogen chloride gas is liberated and then directed on aboslute ethanol solution.

The product is supposed to be chloroethane, right? Or do I need a catalyst (Sulfuric acid) ?

Σldritch - 18-1-2018 at 14:50

No, it needs a catalyst. Perhaps a lewis acid but i think strong halogenation agents are used more in the lab if made at all. I don't think there is a conventional way to do it at home except maybe making it from (anhydrous?) ferric chloride and diethyl ether, from atomistry;

"Ferric chloride combines with ether to form a dark red, highly deliquescent solid of composition FeCl3.(C2H5)2O. It is soluble in water and alcohol, and at 100° C. decomposes quantitatively, yielding the oxychloride FeOCl: -

FeCl3.(C2H5)2O = 2C2H5Cl + FeOCl ."

On the ferric chloride page.

I think it is made by addition of Hydrogen chloride to Ethene in industry but don't quote me on that.

Also, bromides are much easier to make if you have a source of bromine. I dont think it even requires a catalyst, just distillation of ethanol from Hydrobromic acid.

The Volatile Chemist - 18-1-2018 at 15:13

Quote: Originally posted by Σldritch  

Also, bromides are much easier to make if you have a source of bromine. I dont think it even requires a catalyst, just distillation of ethanol from Hydrobromic acid.

- And sulfuric acid (or excess sulfuric if preparing from ethanol, NaBr, and sulfuric acid). This does indeed work, and is even discussed in the beginning of "Excuse Me Sir, WOuld You Like to Buy a Kilo of Isopropyl Bromide", by Max Gergel.

Chemi Pharma - 20-1-2018 at 05:12

From PrepChem, with references:

Preparation of ethyl chloride:

To the round bottom flask fitted with properly cooled reflux condenser and gas inlet 100 g of ethyl alcohol and 50 g of anhydrous zinc chloride are placed. The top of reflux condenser is connected to two washing bottles. The first has water and the second concentrated sulfuric acid. Finally apparatus is connected to a cooled flask for condensing the reaction product. A dry stream of hydrogen chloride gas is passed through the boiling mixture. The vapors of ethyl chloride is washed with water, concentrated sulfuric and condensed in a flask which is cooled with freezing mixture of ice and salt. As ethyl chloride boils at 12° C it must be kept in sealed glass tubes. The yield is almost quantitative.

Preparation of organic compounds, E. de. Barry Barnett, 71, 1912