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- เผยแพร่เมื่อ 7 ก.พ. 2025
- Limonene C10H16 (IUPAC: 1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene) is a cyclic-monoterpene aliphatic hydrocarbon. Monoterpenes are a class of terpenes that consists of two isoprene units bonded in a linear chain or in a cyclic shape. Isoprene is the foundamental unit of all terpenes.
Limonene is the main component of orange and lemon essential oil. Its quantity is variable, depending on the fruit. In orange essential oil, limonene percentage oscillates between 91-97% (depending on the orange’s origin)1 . Other components of orange essential oil are other terpenes (ex. alpha and beta Pinenes) and long chain alyphatic hydrocarbon alcohols and aldehydes. Limonene is a chiral molecule. The (R)- enantiomer (aka D-Limonene) defines orange’s fragrance.
I'm goinf to extract D-Limonene (90+%) from orange peels. The extraction will be performed by Steam Distillation
Steam distillation is a process that involves steam to co-distill a volatile substance. It is one of the most common method to extract natural products from plant materials. Although steam distillation and simple distillation seem to be identical, the theory behind the separation process is quite different. When the components of the starting mixture are immiscibile (ex polar and nonpolar chemicals mixed together), the vapour produced from this mixtures is different. The components act indipendently from one another. The partial pressure of the mixture is no longer defined by the molar fraction of the solute in the solvent, as instead during simple distillation, according to Raoult’s Law. The components of the mixture don’t mix each other in the liquid phase, but in the vapour phase. This allows the co-distillation.
A mixture boils when its vapour pressure reaches the atmospheric pressure (1 atm). Pure water reaches that value at 100°C. Because of the heterogeneous component (orange peels) that contribuites to the total pressure, the mixture is excpected to boil before 100°C. This is an important feature of steam distillation: it allows the extraction of the oil avoiding its decomposition (at high temperature).
Limonene is nonpolar. It’s not miscibile with water. It also has a lower density. Because of this, it forms a layer over the water. The initial mass of peels is 112g. The distillation has been stopped after 4 hours from its beginning. A total of 3ml has been collected. A water drop is observable in the test tube. Because of the much higher density of the water, the drop sinks to the bottom.
Recorded with a NIKON D7500 Digital Camera, DX SWM VR ED IF Aspherical 72 , Edited with Camtasia 9.
References:
Steam Distillation: Lisa Nichols Organic Chemistry Lab Techniques, 2nd edition 2017 organiclabtech...
D-Limonene: PubChem pubchem.ncbi.n...
Notes:
1 orange oil, wikipedia en.wikipedia.o...
Disclaimer: The following process is shown only for demonstration and entertainment purposes. It should not be replicated without proper knowledge. Limonene is a flammable, irritant and toxic chemical and must be handled carefully and safely.
very interesting practical this video really helps me because I'm having the practical today and i get it before getting to the Laboratory thanks so much for the update
Hii! thank you for the video. I wanted to ask, what ratio of water to plant material (orange peels) did you use? Just an approximate guess is fine. Thank you!
Isn't this considered hydrodistillation instead of steam distillation? From what I've looked into, steam distillation separates plant matter from the boiling water instead of the water and the plant matter all being together in a mixture. Does this separation of water and plant matter necessarily need to be the case in order for it to be considered steam distillation or does your method still count as steam distillation?
I use a Clevenger apparatus for essential oil extractions. Less losses of final product than when using a separatory funnel considering the small quantities.
Hi and thanks for a great video! Is it possible to juice the orange peel first. And then distill it?
@@NomadMakes juicing the peel is indeed another extraction method. If you juiced it, then you don't need to distill it. This is a no heat- method, I think more popular in large industrial scale.
@ Will that yield the same product though? Thank you for your reply, by the way. Cheers.
@@NomadMakes At this point, it depends on the machine you use to juice the peel. It should be lower though.
@@francesco.cinzano Yeah. But it seem strange to me at a normal screw type juicer should yield the same product as steam distilling, as simply juicing the zest seems so much easier. It is not that I disagree, I just don't understand.
Hello, this video has been a great help to my studies. May I ask what is the Physical or Chemical Test for limonene to determine it's purity?
For the quantification of chemical compounds mainly instrumental methodologies based on physical principles are used.
In this video, as you could see, a quantification was not carried out, but an estimate was based on the composition of the essential oil extracted.
To learn more about the methods of quantifying limonene, I refer you to this article:
www.perkinelmer.com/PDFs/downloads/APP_Limonene_In_Citrus_Rinds_By_GCMS.pdf
@@CinzLab Thank you very much for this. You are a blessing ♥️. We will be having a reporting about this and I am having a hard time coping up and how to explain it :(
Very interesting! Thanks for uploading.
how can you say that it's purely the limonene of orange is being obtained? great video btw!
We can't say it. It's not pure. We can assume it contains an appreciable amount of limonene since we know the typical high percentage contained in the orange. (The high evaporation rate confirms its presence in a high percentage, though)
Other molecules are also present in smaller quantities.
For a quantitative value of purity, we should carry out a quantitative analysis or an NMR.
Is this a laboratory or industrial
Laboratory right
thanks Guys, it's a really cool video. I'm interested in extracting for use in the kitchen. Ddo you know if the pesticide residues in the lime skin with be transferred to the limonene during the distilattion process?
For food use, such as when making liqueurs (like limoncello), always make sure to work with fruit that has not been treated with pesticides.
Hello CInz thks for the video!! ... how long the extract was in the separatory funnel?
It depends on how fast the oil goes down and separates. It takes about 30 min.
Amazing content. Few subscribers how come!!! let me add one to that.
@4:13 you dropped something into the flask. It looked like a white capsule. What was that please?
That's for mixing (magnetic stirrer)
@@francesco.cinzano Thanks.
what is the temperature required for the extraction of essential oils?
100°C (at standard pressure): the boilong point of water, that is able to safely codistill the oil without thermal-decompose it.
Other videos I have watched usually add a solvent to the hydrosol/oil mixture and use heat in order to separate, I don't understand why they bother.
I find confusing because the two should separate naturally with the oil being non polar as in your video. Is it a yield or purity thing?
The extraction with a solvent is the standard when we have to extract a liquid from another liquid. The extraction of Limonene is also possible with a solvent, like hexane or a non-polar one, and it definitely would maximize the yield.
The extraction of Limonene is also possible without a solvent just because limonene oil has a lower density compared with water. So it naturally floats on the surface.
If you performed an extraction with different oil, like the eugenol, it still won't mix with water, but its density is instead very similar, and the oil will form a suspension of very small oil droplets in water.
The purity of Limonene is directly reliant on the natural composition of the oil, which can slightly change from fruit to fruit. Limonene is however the major component (>80%) of the oil.
@@CinzLab Thank you so much for taking the time to reply to my question. I found it very confusing and you've explained it in a way that was easy to understand
Would ethanol extract more oil?
I do not recommend using ethanol in a hot apparatus due to the inflammable risk, unless in an approlriate lab.
Ethanol however is volatile and if you use it to extract the oil, separate the two will not be easy.
When you use solvent for extraction you use solvent with different density in order to easly separate the two. But then you need to remove the solvent without losing yield in the product.
what is the best solvent to extract limonene ?
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Limonene is totally apolar, being aliphatic, therefore a good solvent must necessarily preserve this characteristic. Furthermore, it must have an appreciable difference in terms of density with respect to water in order to float or sink and make it possible to extract only the apolar phase with the separator funnel. Finally, it must be volatile, in order to be easily removed. Hexane, DCM, acetone... should work.
@@CinzLab thank you !
Wait how is Limonene toxic? There are tons of cocktails that spray orange oil on drinks? You want to tell me that I didn't get poisoned yet?
"D-limonene is listed in the Code of Federal Regulations as generally recognized as safe (GRAS) for a flavoring agent and can be found in common food items such as fruit juices, soft drinks, baked goods, ice cream, and pudding. D-limonene is considered to have fairly low toxicity." pubmed.ncbi.nlm.nih.gov/18072821/
pubmed.ncbi.nlm.nih.gov/23573938/
Caution in chemistry is mandatory. Many harmless substances in small doses become dangerous in large quantities.
Limonene is also an flammable oil! Could be used as an biodiesel
Biodiesels are long chain fatty acid esters, obtained by vegetable oils (triglycerides) reacting with methyl/ethyl alcohols through a process called trans-esterification. Essential oils, like limonene, have different structure and properties and their flammability doesn't lead to an efficient and useful role in biodiesel.
@@CinzLab so it only runs a steam engine :/
@@giovannicesaramorim9adigan961 just water steam can manage it
@@CinzLab i was saying about fuel, like gasoline. Cuz in a steam engine it doesnt need to explode
Hello, may i ask? Can i check purity of d-limonene using FTIR? Also , would the presence be in solid or liquid? Help !
Yes. You can also perform an NMR to best evaluate purity!
What is the quantity of obtained limonene?
About 3mL of Limonene. The presence of that drop of water prevented me from carrying out an evaluation with the balance. I didn't remove it just because I thought it isn't worth it, as far as the yield is very low.
Usually the yield is about 1% (from NileRed) but it can widely change depending on the single orange.
Some organges contain a lot of essential oil, some less. Same for lemons.
Good information but painfully slow and you didn't even say what actual quantity you extracted in the end
My videos are set to be enjoyable and exhaustive as much as possible about every experiment. A slow and peaceful video is essential to allow people to understand the concepts and also to appreciate the clips. This’s
the compromise I found.
The reason why I didn't put the yield in the video is the following (I already answered to this question few comments below): as you can see from the video, a water drop joined along with the oil in the test tube and prevented me to quantify exactly the oil extracted. Removing that drop wouldn’t be worth it. I got about 3 ml of oil: the usual yield is claimed online to be 1%, depending on the variable quantity contained in every single fruit.
Thanks for the reply and info. Was that from about 5 oranges?
@@bodo9387 You're welcome. Yes, from 112g of peels. The yield could be maximise extracting the oil from the distillate with a solvent like DCM (di-chloro-methane) but I do not have a fumehood or an equipped workspace to handle it so I preferred to take advantage of its density property and separate it just with the funnel.
@@CinzLab many thanks, that's helpful. Or separating with a centrifuge?
@@bodo9387 that is a good technique too
hi can you tell me the difference between putting the water in with the peels and having the water in the bottom flask and the peels in a top flask,
There's no difference as long as the steam flows through the peels in the upper flask. It's the steam that extracts the essential oil.
@@CinzLab thanks for the reply, so I'm guessing this goes for all oil extractions. Thanks again.