Sciencemadness Discussion Board

Ethyleneurea

FibreChannel - 29-3-2008 at 11:00

Hi ,

im from Austria ,and im not very good in english :)

Im searching for a synthesis rule of ethyleneurea ,please help me ^^

greetings ,FC

2-Imidazolidinone

smuv - 29-3-2008 at 15:14

ETHYLENE UREA. I. SYNTHESIS FROM UREA AND ETHYLENEDIAMINE and ETHYLENEUREA. II. SYNTHESES FROM ETHYLENE GLYCOL OR
ETHANOLAMINE AND UREA (OR CARBON DIOXIDE AND AMMONIA)

J. Org. Chem. 15, 471-480 (1950)

Attachment: ethylene_urea_JACS_1.pdf (674kB)
This file has been downloaded 3452 times

Since I cant figure how to post w/ 2 attachments

smuv - 29-3-2008 at 15:19

Transesterification of urea and ethylene glycol to ethylene carbonate as an important step for urea based dimethyl carbonate synthesis

Green Chemistry, 2003, 5, 429–432

Attachment: ethylene_urea_GC.pdf (81kB)
This file has been downloaded 1616 times

FibreChannel - 29-3-2008 at 16:20

ohh thanx ,nice ^

Formatik - 29-3-2008 at 16:49

From ethyleneglycol, ethylenediamine or ethyleneoxide and ammonium carbonate. The preparation is described in USP2430874. The reaction with ethyleneglycol: (CH2OH)2 + (NH4)2CO3 -> O=C(NHCH2)2 + 4 H2O. And ethylenediamine: (CH2NH2)2 + (NH4)2CO3 -> O=C(NHCH2)2 + 2 NH3 + 3 H2O.

The patent mentions it was first prepd. from Fisher and Koch in 1885 by heating ethylenediamine and ethyl carbonate around 180 deg. Also formed by electrolysis of parabanic acid, or by desulfuring ethylene thiourea with HgO, and heating water solutions of ethyleneguanidine or ethylenediisocyanate. A more detailed synthesis from the diamine and NH4 carbonate is also given.

[Edited on 29-3-2008 by Hammerl]

[Edited on 29-3-2008 by Hammerl]

Axt - 29-3-2008 at 19:49

http://www.sciencemadness.org/talk/viewthread.php?tid=4282&a...

I've previously attempted both methods in the attachment smuv gave, no luck with ethyleneglycol but then nor was I able to accurately replicate the literature method. I did have success with ethylenediamine though at what purity is unknown, pure wasn't needed as there should be only one stable nitration product (EDNA).

[Edited on 30-3-2008 by Axt]

Formatik - 30-3-2008 at 04:23

Quote:
Originally posted by Axt
http://www.sciencemadness.org/talk/viewthread.php?tid=4282&a...

I've previously attempted both methods in the attachment smuv gave, no luck with ethyleneglycol but then nor was I able to accurately replicate the literature method. I did have success with ethylenediamine though at what purity is unknown, pure wasn't needed as there should be only one stable nitration product (EDNA).


Could there be a difference in the success between urea and ammonium carbonate? This is the patent method using ammonium carbonate:
Quote:
Two hundred and ninety-one grams of ethylenediamine and 480 grams of ammonium carbonate were slowly mixed and when frothing ceased, the mixture was heated in a flask placed in an oil bath and connected to a reflux condenser. The temperature of the mixture was gradually raised to about 145°. and held at this point for several hours. Upon removing the source of heat and cooling the flask to room temperature, a viscous liquid mass was obtained. This mass was then extracted with alcohol, and from the residue obtained by distilling off the alcohol, a white crystalline compound was obtained having a melting point of 131°c., which agrees closely with the melting point of 131.8°C. fror pure ethyleneurea.

Axt - 1-4-2008 at 10:14

Yeh, the only example given is for ethylenediamine and ammonium carbonate, so no advantage over urea which is much more readily available. They do mention ethylene glycol + ammonium carbonate, no example so they could just be covering all possibilities whether it has merit or not.

I also would have thought trying to reflux ammonium carbonate at those temperatures would be very messy, where it would decompose and reform in the condensor. I already had that happening with urea, where it had to be continually removed.

Though thanks for the patent, I hadn't seen it before.