AlchemicalDane
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Registered: 28-5-2013
Location: Denmark
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Mood: Curious
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Eugenol extraction - something happened
Dear fellow chemists,
I figured I should introduce myself before I start asking questions.
I have another user on this forum, but since I have put chemistry as a hobby on the shelf for a while, I decided to make a fresh start.
First of all, I want to make clear that I am NOT interested in the synthesis of ANY form of illegal substances. I am only practicing chemistry as a
hobby because of all the amazing aspects it can be seen from. As we all know, the world of chemistry never ends, and my interest is based on the
curiosity induced by the limitlessness of this world. Now, on to my introduction: I am a hobby chemist situated in Denmark. I have had a huge interest
in chemistry for many, many years, despite my age of 18. I will not go in depth about myself here, however, if you are interested, have a look at my
blog, which can be found here: Alchemical Dane - Tumblr
Now, as you can see in the headline of this topic and on my blog, given that you have looked at it, I have recently tried to extract eugenol from
ground cloves. I have literally no idea about what I am going to use the eugenol for. I did it just for the "doing".
I followed the procedure posted here on the forum (Link to PDF) and doubled the amounts. After the extraction of the acidified aqueous extract with dichloromethane (DCM), I dried it with a
half-saturated solution of NaCl in distilled water. I then left the DCM, containing the eugenol, stand for a couple of hours (a man has to have his
dinner ;-)) and when I came back, the solution had turned all cloudy with a more dense cloudiness in the top of the DCM. I decided to leave it alone
until the next day, and when I came back, it was still cloudy.
From what I have been able to conclude so far, the eugenol does not hydrolyze upon standing with water, and neither does it react with NaCl or DCM.
So, I decided to try and wash the DCM with dilute (2.5%) HCl(aq) to see if that helped. The DCM cleared up a bit, but the particles were still
visible. They did not dissolve in either water or DCM. It remains a puzzle to me what could have happened here.
Any advise on what the product might be or what could have caused the cloudiness in the DCM would be appreciated.
Thank you all in advance for helping me out!
- AlchemicalDane
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AlchemicalDane
Harmless
Posts: 6
Registered: 28-5-2013
Location: Denmark
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Mood: Curious
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Maybe it is worth mentioning that I have excluded the possibility of water causing the cloudiness. The bottle in which the semi-dried DCM/eugenol is
stored was dry when the contents were added. Also, it looks nothing like "wet" DCM. I am quite certain that the cloudiness is caused by some sort of
precipitation as it could be seen in the dilute hydrochloric acid when I tried washing the DCM/eugenol again. When I washed the DCM/eugenol with dil.
HCl again, I noticed that at the face of the two liquids, there was sort of a thick foam or stringy substance. I hope this can help us finding out
what happened here.
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zed
International Hazard
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Registered: 6-9-2008
Location: Great State of Jefferson, City of Portland
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Mood: Semi-repentant Sith Lord
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Well, you could do it that way. But, steam distillation might be easier.
http://www.westfield.ma.edu/cmasi/organic_lab/organic1_lab/i...
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AlchemicalDane
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Posts: 6
Registered: 28-5-2013
Location: Denmark
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As stated, I already steam distilled the cloves. The organic extraction was done on the distillate.
The procedure you posted is very similar to the one I followed.
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AlchemicalDane
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Posts: 6
Registered: 28-5-2013
Location: Denmark
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Mood: Curious
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Can anyone please help me out here? I'm kinda stuck...
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AlchemicalDane
Harmless
Posts: 6
Registered: 28-5-2013
Location: Denmark
Member Is Offline
Mood: Curious
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Since nobody was able to deduce an answer for my question, I decided to vacuum filter the rather large amount of impurities out of the DCM solution. I
then dried it again with a half-saturated NaCl solution and added enough anhydrous sodium sulphate to completely dry the DCM. The DCM was then
filtered and transferred to a clean, dry, amber bottle. Now awaits the distillation of solvent to leave back, hopefully, only pure eugenol.
I just wanted to round up this topic, and the thread is considered closed.
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