Sciencemadness Discussion Board - Cinnamaldehyde from cinnamon bark powder

Cinnamaldehyde from cinnamon bark powder

Random - 5-11-2010 at 01:53

I am thinking about extracting cinnamaldehyde from cinnamon bark powder which can be bought (or maybe the better source is just cinnamon bark?). I would add MEK based nail polish remover to it to extract it and then I would filter the solution. After that I would leave it to evaporate in the air (mek should evaporate). Then I would add water and try to extract cinnamaldehyde from water with potassium metabisulphite.

Is this method good or do you have any more suggestions for that?

bbartlog - 5-11-2010 at 03:14

'MEK based nail polish remover... MEK should evaporate...'

And the other stuff in the nail polish remover, what about that? I don't know what constraints you're operating under but acquiring (either buying or purifying/distilling yourself) some solvent(s) of known composition seems like a good idea. You can't just assume that the other stuff in the nail polish remover won't screw things up somehow.
Here is one extraction described (uses ether): http://lhs2.lps.org/staff/sputnam/Ent801/lab9.htm

digitalemu - 5-11-2010 at 09:32

Fractional distillation under vacuum would be your best bet as you will have your end product in hours, not days. Much less waste, time and effort that way plus you would end up having to distill anyways after the MEK will extract not only your product but other oils too.

digitalemu - 5-11-2010 at 09:39

Quote: Originally posted by bbartlog

'MEK based nail polish remover... MEK should evaporate...'

And the other stuff in the nail polish remover, what about that? I don't know what constraints you're operating under but acquiring (either buying or purifying/distilling yourself) some solvent(s) of known composition seems like a good idea. You can't just assume that the other stuff in the nail polish remover won't screw things up somehow.
Here is one extraction described (uses ether): http://lhs2.lps.org/staff/sputnam/Ent801/lab9.htm

As this page mentions "Purification by flash chromatography", I highly doubt someone who is trying to get MEK from nail polish will have such a setup available to them, nor the ability to acquire such things like isooctane.

not_important - 5-11-2010 at 12:54

Is this true cinnamon, or cassia? In the US cassia is labled as cinnamon, in much of the rest of the world doing so is illegal or at least considered dishonest (if you don't know the flavour difference between cinnamon and cassia, you should learn that).

Within the cassias the Vietnamese or Saigon variety (Cinnamomum loureiroi) has a higher oil content than Chinese cassia or 'cinnamon' (Cinnamomum aromaticum). True cinnamon (Cinnamomum verum) has less cinnamaldehyde than cassia but more of other flavour components, it is 'sweeter' and has overtones of orange or other citrus. True cinnammon's bark is thinner that that of the cassias, almost paper-like and easy to crush in your hand; in the US it can be found in stores catering to folks from Latin America; they know the difference between cassia and cinnamon, unlike the gringos.

Best way to extract is to purchase cassia bark, crush it, and steam distill the oil off. Solvent extract tends to pull out other stuff as well. The bark is tough, not uncommonly a half cm thick; I crush it in a large rough stone mortar from SE Asia, used for mushing chilies and other plants. You can find the bark in Asian stores, particularly herb/medicinal stores.

zed - 6-11-2010 at 04:12

I concur. Try steam distilling it. Nice clean process. Simple equipment.

digitalemu - 6-11-2010 at 08:46

Quote: Originally posted by zed

I concur. Try steam distilling it. Nice clean process. Simple equipment.

Sure, steam distill the bark to get the raw oil, but you will get cinnamon oil and not pure cinnamaldehyde. You still need to perform fractional distillation to get the pure product.

arsphenamine - 6-11-2010 at 09:48

Quote: Originally posted by digitalemu

Sure, steam distill the bark to get the raw oil, but you will get cinnamon oil and not pure cinnamaldehyde. You still need to perform fractional distillation to get the pure product.

Aldehydes have classically been purified by precipitation of the bisulfite adduct, filtration and washing of the solid, and regeneration by gentle hydrolysis with bicarbonate or acid as circumstances dictate.

TLC roughly shows you how impure it is. GC exactly shows you, but doing TLC using coffee filter strips is often all you need.

You can purify by vacuum distillation if you need something analytically pure although you lose some product to the pot.

OrgSynth has a good prep for 3-methyl phenylpropanal.

The money shot:

A completely pure sample of the aldehyde is readily obtained by stirring the crude aldehyde with excess saturated aqueous sodium bisulfite solution for several hours, filtering the solid bisulfite adduct, washing with ether, and liberating the aldehyde with excess aqueous sodium bicarbonate.

The WiZard is In - 6-11-2010 at 12:20

Quote: Originally posted by Random

I am thinking about extracting cinnamaldehyde from cinnamon bark powder which can be bought (or maybe the better source is just cinnamon bark?). I would add MEK based nail polish remover to it to extract it and then I would filter the solution. After that I would leave it to evaporate in the air (mek should evaporate). Then I would add water and try to extract cinnamaldehyde from water with potassium metabisulphite.

Is this method good or do you have any more suggestions for that?

Noted in passing by the book owning analogue guy —

JW Purseglove & et al
Spices
Longman
2 vols 813 pages
1981

p. 126. The finest cinnamon bark oil is produced by steam-
or hydro-distillation with cohobation, and Arctander (1960)
recommends that solvent extraction of the distillate is desirable
to obtain the best quality of oil.

The finest cinnamon bark oils are produced from selected
materials (high-grade) cinnamon quills) in the USA and
Western Europe by steam distillation using modern equipment.
English distilled oil contain about 60 per cinnamaldehyde and about
10 per cent eugenol....

...Sri Larkan bark oil 51 to 76 per cent (av 55) aldehyde...
eugenol 5 tom 18 percent...

And other chemicals! See page 135 for a list. [21 chemicals]
Page 140 for Cassia.

I will leave to others — how-to remove the eugenol.

djh
---
Who is looking for —
Cinnamon and Clove, life-savers candy.

[Edited on 6-11-2010 by The WiZard is In]

Random - 9-11-2010 at 11:27

Well, while MEK based nail polish remover has only impurities water, isopropyl alcohol and calcium chloide (and something like methoxyisopropanol - but it's last on the list so there is maybe a small amount). All that Can be removed after I will solvent extract the oil and evaporate to leave just the oil by using filter paper and then making adduct of cinnamaldehyde with metabisulphite. Cinnamaldehyde will precipitate and then I just need to recover it again

not_important - 9-11-2010 at 12:00

No -start with a pure solvent, which will still extract additional compounds from the cassia, giving a more complex workup that just steam distilling the bark. If you use tech grade solvents it is worthwhile to distill them before use. Starting with crappy solvent mixes, in order to extract complex mixtures, and expecting to easily obtain reasonable pure compounds is generally in the realms frequented by those consuming quantities of herb on a daily basis.

Also
http://pubs.acs.org/doi/abs/10.1021/jf60182a023

Random - 9-11-2010 at 12:04

The only problem is that I don't have distillation equipment so I have to do it with solvents if I am doing it. I would be happy if it would be even just 70% pure, maybe I could later purify it more by other means.

not_important - 9-11-2010 at 12:23

Steam distillation takes little equipment, stainless steel or copper works well for this sort of thing - essential oils from plants. If you use that ugly source of MEK you'll end up having to steam distill anyway. Get pure MEK, or fractionate the MEK out of the polish remover, or use other pure solvents such as ethanol, isopropanol, or DCM. If you use tech grade solvents it is worthwhile to distill them before use.

BTW - distillation was one of the earliest processes used by proto-chemists. While borosilicate ground jointed glassware is nice, much distillation was done with vessels made of other materials although additional care was usually needed to avoid breakage. I've distilled solvents using no more than milk bottles, corks, soda-lime glass tubing, and a slow cooker as a water bath.

[Edited on 9-11-2010 by not_important]

Random - 9-11-2010 at 13:26

Interesting, thanks for that distillation info. So you used glass milk bottles? I don't have glass tubing, could I use plastic tubing that has water soaked paper towel around it for condenser? Also I am thinking about light bulbs, is their glass more heat resistant? Those could be interesting flask (aluminium can be removed with hcl from the light bulb). How dangerous could be distillation in non heat resistant glass? I don't want to be shot with glass bullets while performing it

[Edited on 9-11-2010 by Random]

not_important - 9-11-2010 at 13:57

Plastic tubing generally contains plasticisers, which leach out in organic solvents which thwarts the purpose of distilling. Light bulbs aren't any better, they are very thin and so withstand thermal stress (fast changes in temperature) better, but are also much more mechanically fragile.

Just don't change the temperature quickly, thus the use of a water bath that is heated after the still pot is placed in it - slow cookers are slow, takes a log time to get hot enough which is both bad/annoying but also good.

Random - 9-11-2010 at 15:04

It looks that I should get some copper tubing then, only if I could make some tubing from aluminium foil.. Are there some alternatives to that?

crystalXclear - 18-4-2011 at 19:08

As to the glass, I have made and sucsessfully used a thin flurosent light bulb tube within a larger one, cooled by a recycling pond pump. But as not_important mentioned, they are v-fragile & heat sensative, but great when used with care.
I even used some old heat resistant bricks from a storage heater to create a heat chamber, heated by blow torch to make a verry crude Allihn condenser,
I first sealed the end of one of the smaller tubes up,
then heated it up at intervals & blew down it creating small bubbles along it's length. v-time consumming & broke three before I mannaged it, but man did it work well. lots of fun

Stainless steel works great, but I live in a farming comunity, so from old milk parlours to deralict dairy proseessing buisneses, stainless tubeing and dairy glass are common place here.

I did think about useing that internaly braided clear pipe used on fire extinguishers. It comes in a good range of sizes & has some chemical resistance. could be worth a try.
I allways wanted to try and use it in combination with the glass.
let me know if you do try it, I would love to here of your results.

Anyone know what the new plastic alternative to copper pipe is like? They should be fine with water and alcohols.
There is a thermal pipe of the above that (MAY) be of some use. proberbly not worth the risk though, plastisisers are more of a problem with recycled plastic, but are allway's there.

Just a few thaughts. good luck Xtal

Mailinmypocket - 24-3-2012 at 13:30

I recently attempted to extract some cinnamon oil from about 20 grams of freshly crushed cinnamon sticks, it was a lot of fun and done without soxhlet extractor. I did a steam distillation followed by extraction with dichloromethane and drying the latter over sodium sulfate. Filtered and distilled the dry DCM and was left with a small amount of amazing smelling oil. I dont have the exact yield information or procedure handy at the moment but I can definitely get the info if there is interest

Here is a picture of the final product with a quarter for size comparison.

(Couldnt help myself from tasting the oil on a toothpick, very nice taste... sort of like a cinnamon breath mint without any sweetness!)

[Edited on 24-3-2012 by Mailinmypocket]

hjhearle - 6-11-2012 at 01:46

Trying to extract cinnamon for my final year school chemistry project usin reduction tube setup. A few problems encountered though.....

1) The product lost its distinctive cinnamon smell and turned a dark brown colour. I have tested for oxidation to cinnamic acid but pH was neutral so this can't be it. Any ideas? I ditched this sample (perhaps I shouldn't of?)

2) What viscosity should it be? My freshest sample (right colour and smell so far!

) appears somewhat watery even though I removed what water I could by boiling it off and using anhydrous sodium sulphate. About 3.5ml of it so far.

3) Once I extract a suitable amount I'm going to test its purity with TLC against a known pure sample and react it with 2,4-dinitrophenylhydrazine. What is the definite melting point of the hydrazone and the accepted IUPAC name? I've tried looking this up but results are not concurrent it says 246,255,262 etc.....

Please help! I'll try to upload some photos..... :cool: