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Synthesis of Diethyl Ether from Ethanol

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 less likely to be aware of these dangers. Diethyl Ether vapors 'hug' the ground, and in dry air explosive peroxides can form. In other words, even in a spark/flame free environment, explosions can still happen when ether vapour 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 on days with extremely low humidity. Because diethyl ether is so flammable, and prone to ingition, this procedure 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 a brushless AC motor for the stirrer, because DC motors with brushes generally produce small sparks which could ignite any stray vapours. Diethyl ether is prepared from ethanol (a.k.a grain alcohol, ethyl alcohol, drinking alcohol) by heating it with 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 acid heated to 130°c-140°c. 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 water produced 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 130°c, the reaction is too slow and mostly ethanol will distill. Over 150°c, the ethyl sulfuric acid decomposes, forming ethylene instead of combining with ethanol to form ether.


100g of ethanol (dry ethanol is best) is placed in a 1/2 liter distilling flask. Dump the receiver flask contents into a large beaker or bowl and swirl with 10% Sodium Hydroxide solution until the pH is neutral. Diethyl Ether may be produced by the condensation of ethanol.. then do not use petroleum ether. you see a formula calling for ether. If. and continue heating till the contents of the reaction flask reach 135°C or so. Preparation 3 Diethyl Ether This is also called ethyl ether or ether and must not be confused with petroleum ether. etc. for example. by connecting it to another column and distilling it. and with good cooling. This may be converted to 100% ethanol by mixing the 95% with calcium oxide and distilling .10/20/13 Synthesis of Diethyl Ether from Ethanol 95% ethanol may be recovered from water + CH3CH2OH pulled from the bottom of the fractioning column (marked 'out'). 95% ethanol. Everclear) to the flask. 1. Ethanol is run in from the addition funnel at the same www. 1 = 2 moles. gasp. Make sure your condenser is well supplied with cold water. no column at all) will require slower distillation (and if you don't use a column. Let the last wash solution + Ether rest in the flask until everything has settled. The addition funnel should extend below the surface... and pour the Ether out of the top into a round bottom A shorter column (or. you will have to do some extensive washing of the product with saltwater). Once distillation commences. and a thermometer goes in the other side neck.the water is used up to make Calcium hydroxide! This in turn can be re-fed to the "FEED TANK" after cooling. Heat and maintain the mixture's temp at 140-145°c by heating on a sand bath. assemble a typical fractional distillation setup with a vigreux column and a three neck flask. and bring the flask up to 130C. then carefully drain off the wash. To do this. 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/100mL of water @ room temp).erowid. Don't forget to drop a stirrer magnet into the flask before clamping everthing up. Preparation 2 by Eleusis Though this is not the most pleasant process. then it refers to diethyl ether.. slowly add up to another 2x moles of Ethanol through the addition funnel at a rate equal to the drops coming from the condenser.ether. This flask needs a thermometer fitted. Distill the Ether from the Calcium Chloride by heating on a bath (oil or water) at no higher than 45C! Collect distillate that comes over in the range of 31-36°C. turn on the heat. so that the ethanol can be added below the surface of the acid. drop in stirrer magnet and stir for 2 hours. Add 2x moles (where the x is a multiplier. Turn on the stirrer. The vigreux column goes in the central neck. Add 15g of Calcium Chloride (Damp-Rid) for every mole of Ether.5 = 3 moles. Add 2x moles of concentrated (98%) Sulfuric Acid (ie .. you know).html 2/3 . and you will be heating this on an oil bath (no flames allowed when Ether is around.Instant Power Drain Opener) to the Ethanol slowly (it will heat because of the water).) of the azeotrope of Ethanol (ie. 2 moles of alcohol (114g) should take 1 hour with a decent vigreux column. 180g of concentrated sulfuric acid (98% H2SO4 is added slowly. an addition funnel in one side beck. if it does not specify petroleum ether. so that the bulb dips down below the liquid surface.

org/archive/rhodium/chemistry/ethyl. Note: Ether develops explosive peroxides upon sitting for any length of time. The distillate will require the following purification steps: Shake twice with 50 cc of 10% sodium hydroxide solution. Mark the flask before distilling. before handling ether. The ether is then dried over anhydrous calcium chloride for 24 hours and distilled on a water bath. Therefore. which has been stored.html 3/3 . Anhydrous Ethyl Ether. Shake twice with 50 cc of saturated sodium chloride solution.10/20/13 Synthesis of Diethyl Ether from Ethanol mixture's temp at 140-145°c by heating on a sand bath. This is for those formulas calling for dry. To keep peroxides from forming in fresh ether. Ethanol is run in from the addition funnel at the same rate as the liquid distills over (about 2 drops per second). Yield: 100g. so that you can be sure of the addition rate. collecting the fraction boiling at 35°C. The ether product from above is dried over thin slices of metallic sodium (metallic sodium wire works well also) for 24 hours. even if just purchased from a supply house. to free from ethanol. After about 150g of alcohol (ethanol) has been added. pure. add several sections of copper or iron wire to the dark container and store in a cool place.ether. www. shake with ferrous sulphate or with lead peroxide. over fresh (fresh means a different batch than what you used to dry with) metallic sodium.erowid. or anhydrous ether. to free from sulfuric acid. Then the ether is distilled on a water bath. stop heating.