Author Topic: Advanced Chemistry: Isolation of Cinnamaldehyde from Cinnamon Sticks  (Read 329 times)

cheesie

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Advanced Chemistry: Isolation of Cinnamaldehyde from Cinnamon Sticks
« on: June 14, 2009, 04:53:29 PM »
1. Set up an immersion heater in a 400 mL beaker with 300 mL of water
2. Break up a cinnamon stick into small slivers (15 x 3 mm). Place the pieces into a tarred reaction vial and mass
the cinnamon and vial. Use about 1.5-2.0 g of cinnamon. Record the mass of the vial and vial/cinnamon
3. Add 5 mL of tap water to the reaction vial and seal the flask with a Teflon-coated cap.
4. Place the vial into the hot water and check for bubbles. If bubbles appear, remove the vial and tighten the cap.
5. Heat the vial for 25 minutes. After 25 minutes, remove the vial and allow to air cool for a few minutes. After
cool, place into a beaker with cold water for about three minutes.
6. Open the vial slowly. Remove the aqueous solution of cinnamaldehyde into a clean reaction vial. Do not transfer
any of the cinnamon pieces. These may be discarded into the garbage.
7. Smell the mixture. Record.
STOP FOR THE DAY. CLEAN UP YOUR LAB. LABEL YOUR VIAL CLEARLY AND SET ASIDE FOR
TOMORROW.
8. Extract the cinnamaldehyde with ethyl ether. Add about 2-3 mL of ethyl ether to the aqueous solution. Tightly
cap the vial and mix the two layers by inverting the vial several times. Be careful not to shake the vial as an
emulsion (layer of bubbles between the two layers) can be created thus increasing the separation time.
9. Allow the two layers to separate. Transfer the upper organic solvent layer into a clean reaction vial using a
pipette. This layer will contain ethyl ether and cinnamaldehyde.
10. Repeat steps 10 and 11. Combine the ethyl ether solutions from the two extractions into one reaction vial.
11. Dry the cinnamaldehyde solution with anhydrous magnesium sulfate. Add only a small amount (~2-3 mm on
the bottom of the vial). If the magnesium sulfate is clumped up, add a little more until the magnesium sulfate stops
clumping. Transfer the ethyl ether solution containing cinnamaldehyde to a clean, tarred evaporating dish using a
pipette. Rinse the magnesium sulfate with 2-3 mL of clean ethyl ether and combine with the cinnamaldehyde
solution in the evaporating dish. Record the mass of evaporating dish and evaporating dish /cinnamaldehyde
solution.
12. Place the evaporating dish in a fume hood for 5-10 minutes allowing the ethyl ether to evaporate. Small
droplets of cinnamaldehyde will remain after all the ethyl ether has evaporated. Ethyl ether has a low boiling point
(40-70 oC). Cinnamaldehyde has a boiling point of 248 oC.
13. Smell the evaporating dish after all the ethyl ether has evaporated. The oily droplets will have a strong
cinnamon smell.

Vesp

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Re: Advanced Chemistry: Isolation of Cinnamaldehyde from Cinnamon Sticks
« Reply #1 on: June 14, 2009, 09:06:47 PM »
Cool. I bet there will be other impurities besides the aldehyde though. It is likley that one could further purify it, if they felt necessary by forming bisulfite adducts with the aldehydes, leaving the other junk behind.
I don't know what there would be other then some oils from the plant, etc. Probably isn't needed for a lot of things.
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Sedit

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Re: Advanced Chemistry: Isolation of Cinnamaldehyde from Cinnamon Sticks
« Reply #2 on: June 14, 2009, 11:00:56 PM »
using 1.5-2.0 g of cinnamon bark how much aldahyde could one even possibly expect to get. If one wanted to go thru the trouble of getting Cinnamaldehyde from the bark it makes much more sence to just grind it up and steam distill it instead of getting a few mg at a time from a method like this. Steam distillation will more then likely yeild a purer product and you will not have to waste a mess load of ether in the process.

What are the plans for any Cinnamaldehyde that one would get from extraction Cheesie?

BTW I got a freind that goes by that name and is in a band you aint any good at Gee Tar are ya?
There once were some bees and you took all there stuff!
You pissed off the wasp now enough is enough!!!

RePHluX

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Re: Advanced Chemistry: Isolation of Cinnamaldehyde from Cinnamon Sticks
« Reply #3 on: December 12, 2009, 01:33:47 AM »
(*@#$^^*@#&(@#!!!!!!!!!!!   WHY?!?!

I understand that you want to test out your wings a bit.  Maybe can't order it but.......?

ANyways...

DOn't mean to offend anyone as I am new to this site..........ORDER IT!  IT IS DIRT CHEAP!!!

jon

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Re: Advanced Chemistry: Isolation of Cinnamaldehyde from Cinnamon Sticks
« Reply #4 on: December 16, 2009, 06:18:53 AM »
ever heard of cassia oil???

poisoninthestain

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Re: Advanced Chemistry: Isolation of Cinnamaldehyde from Cinnamon Sticks
« Reply #5 on: December 20, 2009, 01:50:23 AM »
Word. The percentage of aldehyde/kilo sticks isn't economical in the slightest as the oil percentage only numbers in the single digits if mem serves right. Raw cinnamaldehyde is dirt cheap as it's been said before me. Steam distill a la pressure cooker would be much easier if it had to be done. I use one for anything oil from plant material be it sass, piper, and your other major plant EO's.  Just sayin.

hypnos

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Re: Advanced Chemistry: Isolation of Cinnamaldehyde from Cinnamon Sticks
« Reply #6 on: April 18, 2011, 03:58:56 AM »
do you use the pressure cooker as a 'source of steam' to pass through the plant matter, and then into another container,, or do you reflux the whole lot together, and then separate?
  I havent used a pressure cooker for this purpose, yet, but i imagine thet could/would be a good way to go....what's your opinion poision man?
 hyppy
"the two things you can give away and never lose, are what you know, and how you feel...."

poisoninthestain

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Re: Advanced Chemistry: Isolation of Cinnamaldehyde from Cinnamon Sticks
« Reply #7 on: April 18, 2011, 06:33:42 PM »
throw the whole mess into the pressure cooker with a nice excess h2o then take off the steam release valve to replace it with some long tubing which youll feed into your condenser...then just use propane as your heat source...heating on a hotplate takes forever...quick ghetto...i get very nice saf this way from bark...technically "indirect steam distillation"

salat

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Re: Advanced Chemistry: Isolation of Cinnamaldehyde from Cinnamon Sticks
« Reply #8 on: April 18, 2011, 06:43:58 PM »
You can distill it in a microwave as well.  I've got a thread on microwave chemistry going at wetdreams with lots of reference papers etc.

Grind up the cinnamon (cassia is available cheap from oriental grocers).
Soak it in distilled water -
Put the wet cinnamon in a flask. 
Put the flask in a microwave with a hole drilled in the top (safe as long as hole is < 1/4 the wavelength)

See pics for setup, you need a heating source for the glassware outside the microwave and insulation for the flask inside the microwave because glass is transparent to microwaves and doesn't heat.  Also takes too long for it to heat up without the heating tape.

Microwave at 20% for 5 minutes to get it started, then 10% until the cinnamon dries out.  Be careful because once it dries out, the heating gets intense and will burn.

The distillation goes faster if the media is more finely ground - probably only a minute at 20% for the initial warm up phase.  I'm just getting this working after a couple of months of playing with it, so more refinements will be forthcoming.  This looks like a really fast and economical way to get essential oils.

Salat
Salat

hypnos

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Re: Advanced Chemistry: Isolation of Cinnamaldehyde from Cinnamon Sticks
« Reply #9 on: April 19, 2011, 01:46:39 PM »
   
Quote
throw the whole mess into the pressure cooker with a nice excess h2o then take off the steam release valve to replace it with some long tubing which youll feed into your condenser
   Yeah, thats how I imagined it,,thanx for the reply 8)

    DO you need to keep topping up the h2O very often?     M  at  ey I reckon this method, using a pressure cooker and a loooong polypipe to a condensing unit is the most 'sensible Home route, one can do---bar none--soxhlets are far too complex, :P,Not 'ghetto' at all! ::)---how do you stop the plant product from blocking the steam hole?-- and how 'full' do you fill it, first time?-what kind of ratios do you usa ,,plant matter% to H2O %? or is it a basic "Ya gotta suck it and see.." type thing...play it by 'feel' more so?

  Cheers poision man
   
          Hyppy
"the two things you can give away and never lose, are what you know, and how you feel...."