synthesis of diethyl ether from ethanol

8/14/2019 Synthesis of Diethyl Ether From Ethanol

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10/20/13 Synthesis of Diethyl Ether from Ethanol

www.erowid.org/archive/rhodium/chemistry/ethyl.ether.html

Preparation of Diethyl ether

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Preparation 1

This is somewhat dangerous to perform with the right equipment, and without the right gear, very dangerous

Diethyl ether, or CH3CH2-O-CH2CH3, is a great solvent for many things, but is extremely flammable.

Professional chemists will be well appraised of the hazards presented in using ether, but the layperson is les

likely to be aware of these dangers. Diethyl Ether vapors 'hug' the ground, and in dry air explosive peroxidescan form. In other words, even in a spark/flame free environment, explosions can still happen when ethervapour is encountered. For this reason its probably a good idea to have some way of removing vapours from

the vicinity (a fume hood would be a fine example) and (Zaphraud suggests) one should not use ether ondays with extremely low humidity. Because diethyl ether is so flammable, and prone to ingition, thisprocedure should be carried out using a hotplater/stirrer designed for use in flammable environments. Such a

heater/stirrer does not produce a contact spark when the hotplate is turned on, and generally employs abrushless AC motor for the stirrer, because DC motors with brushes generally produce small sparks whichcould ignite any stray vapours.

Diethyl etheris prepared from ethanol(a.k.a grain alcohol, ethyl alcohol, drinking alcohol) by heating itwith concentrated. The reaction proceeds thru an intermediary, "Ethyl sulfuric acid", as do most reactions of

this type.

Preparation 1

by Zaphraud

The reaction is conducted as follows:

Dry (anhydrous) or nearly dry ethyl alcohol is allowed to flow into a mixture of alcohol and sulfuric acidheated to 130c-140c. The vapors are collected, and ether and some alcohol and water condense out. The

sulfuric acid is a catalyst, but since it becomes more and more dilluted as a consequence of the waterproduced by the reaction, the process becomes inefficient (which is why anhydrous ethanol is the best!)

The temperature of the reaction should be controlled carefully. At temperatures below 130c, the reaction istoo slow and mostly ethanol wil l distill . Over 150c, the ethyl sulfuric acid decomposes, forming ethyleneinstead of combining with ethanol to form ether.


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95% ethanol may be recovered from water + CH3CH2OH pulled from the bottom of the fractioning column

(marked 'out')... by connecting it to another column and distilling it...

This may be converted to 100% ethanol by mixing the 95% with calcium oxide and distilling - the water isused up to make Calcium hydroxide! This in turn can be re-fed to the "FEED TANK" after cooling.

Preparation 2

by Eleusis

Though this is not the most pleasant process, Diethyl Ether may be produced by the condensation of ethanol.To do this, assemble a typical fractional distillation setup with a vigreux column and a three neck flask. Don'forget to drop a stirrer magnet into the flask before clamping everthing up, and you will be heating this on an

oil bath (no flames allowed when Ether is around, you know). The vigreux column goes in the central neck, aaddition funnel in one side beck, and a thermometer goes in the other side neck.

Add 2x moles (where the x is a multiplier, 1 = 2 moles, 1.5 = 3 moles, etc...) of the azeotrope of Ethanol (ie95% ethanol, Everclear) to the flask. Add 2x moles of concentrated (98%) Sulfuric Acid (ie - Instant PowerDrain Opener) to the Ethanol slowly (it will heat because of the water). Turn on the stirrer, turn on the heat,

and bring the flask up to 130C. Make sure your condenser is well supplied with cold water, and continueheating till the contents of the reaction flask reach 135C or so.

Once distillation commences, slowly add up to another 2x moles of Ethanol through the addition funnel at a

rate equal to the drops coming from the condenser. 2 moles of alcohol (114g) should take 1 hour with adecent vigreux column. A shorter column (or, gasp, no column at all) will require slower distillation (and ifyou don't use a column, you will have to do some extensive washing of the product with saltwater).

Dump the receiver flask contents into a large beaker or bowl and swirl with 10% Sodium Hydroxide solutionuntil the pH is neutral. Pour this mixture into a separatory funnel to separate the Ether from the aqueous

hydroxide and wash twice more with equal volumes of half-saturated Sodium Chloride solution (~18g/100mLof water @ room temp). Let the last wash solution + Ether rest in the flask until everything has settled, thencarefully drain off the wash, and pour the Ether out of the top into a round bottom flask. Add 15g of Calcium

Chloride (Damp-Rid) for every mole of Ether, drop in stirrer magnet and stir for 2 hours.

Distill the Ether from the Calcium Chloride by heating on a bath (oil or water) at no higher than 45C! Collectdistillate that comes over in the range of 31-36C.

Preparation 3

Diethyl Ether

This is also called ethyl etheror etherand must not be confused with petroleum ether. If, for example,

you see a formula calling for ether, then it refers to diethyl ether, if it does not specify petroleum ether, thedo not use petroleum ether. 100g of ethanol (dry ethanol is best) is placed in a 1/2 liter distilling flask, andwith good cooling, 180g of concentrated sulfuric acid (98% H2SO4is added slowly. This flask needs a

thermometer fitted, so that the bulb dips down below the liquid surface. The addition funnel should extend

below the surface, so that the ethanol can be added below the surface of the acid. Heat and maintain the'


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- .rate as the liquid distills over (about 2 drops per second). Mark the flask before distilling, so that you can besure of the addition rate. After about 150g of alcohol (ethanol) has been added, stop heating. The distillate

will require the following purification steps: Shake twice with 50 cc of 10% sodium hydroxide solution, to frefrom sulfuric acid. Shake twice with 50 cc of saturated sodium chloride solution, to free from ethanol. Theether is then dried over anhydrous calcium chloride for 24 hours and distilled on a water bath, collecting the

fraction boiling at 35C. Yield: 100g.

Anhydrous Ethyl Ether. This is for those formulas calling for dry, pure, or anhydrous ether. The etherproduct from above is dried over thin slices of metallic sodium (metallic sodium wire works well also) for 24

hours. Then the ether is distilled on a water bath, over fresh (fresh means a different batch than what youused to dry with) metallic sodium. Note: Ether develops explosive peroxides upon sitting for any length oftime, even if just purchased from a supply house. Therefore, before handling ether, which has been stored,

shake with ferrous sulphate or with lead peroxide. To keep peroxides from forming in fresh ether; addseveral sections of copper or iron wire to the dark container and store in a cool place.

synthesis of diethyl ether from ethanol

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