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Author: Subject: Diethylamine from Ammonium Hydroxide

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Registered: 8-11-2016
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[*] posted on 8-11-2016 at 20:23
Diethylamine from Ammonium Hydroxide

SWIM is interested in producing diethylamine (purely as an intellectual curiosity)

Based on Practical LSD Manufacture by Uncle Fester diethylamine can be made from ethyl iodine and liquid ammonia (assumed to be anhydrous ammonia). However, anhydrous ammonia is not easily available so SWIM is wondering about substituting ammonium hydroxide for anhydrous ammonia.

Here is the basic equation (pretty sure it is balanced correctly but some additional water would likely be on both sides of the equation as the NH4OH is mixed with water) :
3NH4OH + 6CH3CH2I --> 6HI + CH3CH2NH2 + (CH3CH2)2NH +(CH3CH2)3N+3H2O

Here is the synthesis:
Cool all reagents to 0 degrees C

1). Add 175 ml ethyl iodine to a tightly sealed beaker
2). Add 1750 ml 30% ammonium hydroxide to this tightly sealed beaker
3). Place beaker in ice bath and maintain temperature at 0 deg. C
4). Shake beaker every 5 minutes for 30 minutes
5). Slowly add dilute sodium hydroxide (90g NaOH dissolved in 100 ml H2O) to neutralize HI. This should yield freebase ammonia, ethlyamine, diethlyamine, and triethlyamine.
6). Extract freebase with toluene using a sep. funnel (this should remove any water produced in the reaction with ammonium hydroxide and added during neutralization).
7). Fractionally distill toluene extract saving the portion that is recovered at 55 degrees C (diethlyamine).
8). Dry diethlyamine over potassium hydroxide chips.

Note: Any remaining ammonium hydroxide would come off as ammonia gas at a low temperature during the distillation (should gas off at around 25 degrees C). Obviously any water would be left in the distillation flask as it does not boil until 100 degrees C (however, this should have been removed during the toluene extraction).

Does anyone see any basic problems with this?
Would the extra hydroxide group mess up this reaction?
Is ammonium hydroxide too stable to react with ethyl iodine without increasing the temperature over 0 degrees C? If so, at what temperature could this reaction occur at?

Thank you in advance!!


[Edited on 9-11-2016 by MyNameIsReserved]

[Edited on 9-11-2016 by MyNameIsReserved]

[Edited on 9-11-2016 by MyNameIsReserved]

[Edited on 9-11-2016 by MyNameIsReserved]
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[*] posted on 8-11-2016 at 22:00

Your post actually detracts from the sum total of human knowledge.

At no point on your rambling, incoherent question were you even close to anything that could be considered a rational thought. Everyone here is now dumber for having read it.
I award you no points, and may god have mercy on your soul.

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[*] posted on 9-11-2016 at 00:18

We don't SWIM here, this is a chemistry forum.

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