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The Hive => Chemicals & Equipment => Topic started by: Vibrating_Lights on February 06, 2003, 05:44:00 AM

Title: Industrial Diethylamine Stnthesis
Post by: Vibrating_Lights on February 06, 2003, 05:44:00 AM

I dug this up somewhere...

Chemicals:

Ethanol (EtOH)
57% Hydrogen iodide (57% HI, see MISC section)
Zn metal
aqueous ammonia (NH3)
epsom

1-Add 119g of ethanol into a flask.
2-Add enough 57% HI to a separate flask so it conatins ~340g of HI.
3-Add a couple pinches of zinc metal to the HI, and reflux it until all of the Zn goes into the solution.
4-Cool the HI back down to room temp, and add it to the ethanol. Reflux solution for 3 hours.
5-When done, setup for distillation, and distill out unreacted ethanol/EtI (ethyl iodide) mixture (b.p. 72-79 deg C).
6-Split the EtI and ethanol fraction in half, and add enough ammonia solution one half the EtI/ethanol mix that contains ~44g of NH3.
7-Reflux that mix with cold ass water in the condensor, and a balloon over the flask to aid in keeping ammonia in, for about 1 hour.
8-When done refluxing, setup for distillation.
9-First distill out the ethylamine produced, then any unreacted EtI/Ethanol.
10-Add the other half of the EtI/ethanol solution to the freshly distilled ethylamine.
11-Reflux this solution for another hour or so.
12-Setup for distillation again, and distill out unreacted ethylamine. Then distill out your diethylamine.
13-Use procedure above to make your diethylamine anhydrous.


My question is.  Can HBr be substituted for the HI?????
Vl_

Title: seems like it could
Post by: darius on February 17, 2003, 02:29:00 AM

it seems like it should be able to, they are in the same period.  But Bromine is obviously weaker than Iodine because of it's placement on the period, so that means you'd need to adjust your amts. Whatsa matter with HI though? 

lata
D

Title: Nothing is keeping the ethyl iodide from ...
Post by: Rhodium on February 17, 2003, 02:34:00 AM

Nothing is keeping the ethyl iodide from alkylating the diethylamine, so you will end up with a lot of triethylamine too.

Title: Uncle fester
Post by: sYnThOmAtIc on March 18, 2003, 03:58:00 AM

Isn't that the same procedure that is in uncle festers book about acid production?

BTW what it the most common and practical way to make Diethylamine? I still have never found that procedure for making it from the pesticide in "OFF" bug repellant that everybody touted about being so good and "OTC" but never been able to locate more thatn a discussion on it. So could someone please direct me to that or any other source for finding dieam synths

Title: Left as an exercise.
Post by: terbium on March 18, 2003, 04:36:00 AM

I still have never found that procedure for making it from the pesticide in "OFF" bug repellant that everybody touted about being so good and "OTC" but never been able to locate more thatn a discussion on it.
That is perhaps because the procedure would be so trivial that it doesn't need to be stated in great detail. Hydrolyze by boiling in 20-30% HCl for a few hours then separate the toluic acid from the diethylamineHCl.

Title: Amide Hydrolysis
Post by: foxy2 on March 18, 2003, 04:41:00 AM

I still have never found that procedure for making it from the pesticide in "OFF" bug repellant that everybody touted about being so good and "OTC" but never been able to locate more thatn a discussion on it.

First I would try adding NaOH and distilling.
Maybe these?

Post 288046 (https://www.thevespiary.org/talk/index.php?topic=7728.msg28804600#msg28804600)

(Rhodium: "Amide hydrolysis with methoxide", Chemistry Discourse)

Post 244440 (missing)

(MaDMAx: "Re: diethylamine", Chemicals & Equipment)

Post 71976 (missing)

(halfapint: "Re: got dimethylamine?", Chemicals & Equipment)

Title: Wouldn't basic hydrolysis work to?
Post by: foxy2 on March 18, 2003, 04:45:00 AM

Wouldn't basic hydrolysis work to?

I don't know what the difference between acidic and basic hydrolysis would bee?