Isolation of Cinnamaldehyde from Cinnamon


Introduction
Commercial cinnamon consists of dried, ground bark from the cinnamon tree, and contains about 2% cinnamaldehyde, which is responsible for its distinct flavor and odor.


The isolation will be accomplished by steam distillation. This means that the solid cinnamon will be boiled in water, and the steam will be condensed and collected. Since cinnamaldehyde is soluble in steam (but not in water), it will be carried up with the distillate and form a finely distributed emulsion, which will appear milky upon cooling. Many other essential oils can be isolated in this way – anisole from anise, camphene from nutmeg, carvone from caraway and spearmint, cuminaldehyde from cumin, eugenol from cloves, safrole from sassafras, and limonene from citrus peel.
A common way of isolating cinnamonoil along with cinnamaldehyde fromcinnamon bark, even in industrial scale, isthrough steam distillation. The cinnamon oilisolated through steam distillation containsroughly around 90% trans-cinnamaldehyde.Cinnamaldehyde contains a formylgroup, and is therefore an aldehyde. Itsstructure has a phenyl group attached to an
unsaturated aldehyde. It named throughIUPAC nomenclature as 3-phenyl-2-Propenal.The experiment aimed to isolatecinnamon oil from cinnamon bark by steamdistillation. From cinnamon oil,cinnamaldehyde could be extracted bymultiple extractions using DCM as a solvent,through aqueous dispersion. In theexperiment done, cinnemaldehyde wasanalyzed by subjecting it to Tollen’s test andPhenylhydrazone test, both of which test forthe presence of aldehydes

Procedure
Steam distillation of the cinnamon:
• Obtain a 100 ml Erlenmeyer flask with a 14/20 ground glass joint from the instructor.
• Add 15 ml of distilled water, 2 drops of Triton X-100 (a surfactant which reduces
foaming), 2.0 g of cinnamon, and a long stir bar.
• Attach a Hickman still to the flask, then top it with a reflux condenser. Attach the reflux
condenser to the water hoses and turn on the water. Insulate the top of the flask below the
neck of the still with aluminum foil.
• Turn on the stirrer and begin to heat the cinnamon mixture slowly until it begins to boil.
• If it foams up into the still, you are heating too quickly – if the foam gets into the lip of
the still, you'll have to take it off and clean it before continuing.
• Remove the distillate with a pipet as it collects and place it in a beaker or flask.
• If, after collecting some distillate, the still begins to look dry, add up to 1 ml of water (no
more!). Try not to bake the cinnamon onto the glassware, as it is hard to clean out.
• You should collect about 5 ml of distillate; once it no longer turns milky on cooling, most
of the cinnamaldehyde has been removed.
Isolation of the cinnamaldehyde from the distillate:
• Place a sep funnel on the clamp and put a beaker underneath it. After making sure the
stopcock is closed, transfer the distillate to the sep funnel.
• Extract it by adding about 5-10 ml of dichloromethane, shaking, allowing it to separate,
and draining off the dichloromethane.
• Repeat two more times, combining all of the dichloromethane layers that you drain off.
Don't throw away anything until you are sure you have what you want!
• Dry the dichloromethane solution by adding sodium sulfate until it is free flowing.
• Transfer the solution to a tared (preweighed) round bottom flask and rinse the solid
sodium sulfate with a little more dichloromethane. Evaporate the solution on the rotovap.
• Observe the product that you have obtained and record your observation. Authentic
cinnamaldehyde is a clear, slightly yellow liquid with a strong odor of cinnamon.
• When the flask is cool, obtain the mass of the cinnamon oil that you have extracted.
Calculate the % recovery of cinnamaldehyde.
• Discuss the odor, appearance, mass, and percent recovery of the cinnamaldehyde in your
conclusion.

11 komentar:

Vebria Ardina mengatakan...

Cinnamaldehyde cannot be distilled directly because it decomposes before it reaches a boiling
point (about 248o C). How does steam distillation avoid this difficulty?

elsa yanti mala mengatakan...

i find an article about steam distilation.
Steam distillation is used to separate mixtures of compounds having a boiling point reached 200 ° C or more. Steam distillation to vaporize these compounds with temperatures approaching 100 ° C under atmospheric pressure using steam or boiling water.
The basic principle of steam distillation distilling a mixture of compounds is below the boiling point of each compound mixtures. Besides steam distillation can be used to mix the water insoluble at all temperatures, but can be distilled with water.
Steam distillation serves to purify the substance / liquid compound that is not soluble in water, and the boiling point is high, whereas before the liquid reaches its boiling point, the liquid is biodegradable, oxidized or undergo conversion reactions (rearranagement), the liquid can not be purified by simple distillation or distillation rise, but must be distilled by steam distillation. i think this information could help your problem. thank's

choirunnisa mayara mengatakan...

vebria, i have a question for you about this. What would happen if you evaporated the dichloromethane solution without drying it first?

yulia mengatakan...

Dried cinnamon bark advance
grinded into powder size of 100
mesh. Cinnamon powder has
mashed weighed as much as 200 g,
then performed with distilled water
Clevenger method using a Dean
Stark for 6 hours. Refining done
10 times. The oil obtained
collected, dried with Na2SO4
anhydrous, and determined the yield of oil
roughness (w / w). Components of oil compounds
rough identified using GCMS
based library Willey W8N08 year
, 2008. In addition, specific gravity determined and
refractive index of cinnamon oil
obtained using Pycnometer
and Abbe refractometer '.

Lina Purwanti mengatakan...

i red your material about this "Many other essential oils can be isolated in this way – anisole from anise, camphene from nutmeg, carvone from caraway and spearmint, cuminaldehyde from cumin, eugenol from cloves, safrole from sassafras, and limonene from citrus peel".
so my question is whether these examples has the same distillation process?
Can give examples for limonene from citrus peel distilation process?
give your comment

Vebria Ardina mengatakan...

Thanks for your comment Elsa. i wanna ask one more "does not damage the structure of the steam distillation of flavonoids? and whether flavonoids can be insulated properly?"

Vebria Ardina mengatakan...

Thanks for your Question. according me afer i read some journal,i found Thus, removing water and other impurities from a solution can become an arduous task but is necessary if the reagents are also sensitive towards water.Grignard reagents or in cases where water has a detrimental effect on the yield or rate of the reaction.
May be any other answer From Chemist? Share your answer here

Vebria Ardina mengatakan...

Thanks Yuli, by the way any other way that faster? I think 6 hours is too long

Vebria Ardina mengatakan...

Thanks for your question Lina. i've read other journal and i found This Link "http://fainweb.uncoma.edu.ar/termodinamica/index/orange%20oil,%20JSCF%202005.pdf" you may checked it for more complete

dini oktaviani mengatakan...

what is the use of Cinnamaldehyde in the health field?

Unknown mengatakan...

all process i have done to isolation of that. but how to find the % of cinamaldehyde in our oil contain and it is sis or trans cinnamaldehde???

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