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249 Lemons!1!!

Poppy - 12-8-2012 at 16:26

Ok right now I have 249 lemons in my hands, freshly bushed. I'm planning to experiment with its vitamin C and citric acid.
So, any ideas, suggestions, I'll do it, it will just depend on the chemicals available to perform all the stuff here!!

Here they are, reagent grade

[Edited on 8-13-2012 by Poppy]

Mailinmypocket - 12-8-2012 at 16:40

Grate the zest off all of them and do a huge extraction of limonene!

cyanureeves - 12-8-2012 at 16:42

lemonade for sure and maybe you can come up with some kind of mosquito repellant. mosquitos hate lemon grass so maybe they dont like lemons either.

[Edited on 13-8-2012 by cyanureeves]

Poppy - 12-8-2012 at 18:46

Mailinmypocket:

Lemonene theorically is said to be distillable without decomposing. But the ammounts that would be found are so small a solvent extraction must be performed in place. Guess alcohol will do it? Familiar to limoncello liquors?

After peeling..'n smashin... Yuurayy! Lemonade for half a year! As they would never survive invitro like that, instead let they feed the backyard chem! Look, Im not torturing the lemons, they would rotten anyways!

Mailinmypocket - 12-8-2012 at 19:53

Steam distillation of the zest goes quite well, although I should have said orange/lemon oil and perhaps not limonene specifically. I can't find the procedure I followed a few months back when I steam distilled orange oil, below is a similar process except I extracted the oily layer from the distillate with ether and dried that over sodium sulfate and distilled off the ether which gave a powerful smelling extract reminiscent of the scent of Pledge furniture cleaner.

http://www.rsc.org/learn-chemistry/content/filerepository/CM...

Upon further searching I found this more in-depth experiment on extractions:

http://infohost.nmt.edu/~jaltig/SteamDistill.pdf

I thought it was more interesting to isolate the product as much as possible using a solvent extraction of the distillate

[Edited on 13-8-2012 by Mailinmypocket]

hyfalcon - 13-8-2012 at 02:06

D-limonene is a byproduct of making orange juice. I don't think it even takes steam to get the orange oil out of the peels, they just press it. The d-limonene is a fraction of the expressed orange oil, about 85-90% I think if I remember correctly.

[Edited on 13-8-2012 by hyfalcon]

Poppy - 13-8-2012 at 06:36

85%???

Its seems reliably easy to do the extraction. For it will render the first usage of my distillation apparatus!!

Later on the oil will be kept and, after producing ether, further extracted according to the files you provided above.
It's a lot o peel, hope it works, I just have to improvise hooks for my glassware

Thx

vmelkon - 13-8-2012 at 07:19

I say do it.
I did it a couple of weeks ago using orange peel. I had been collecting the peels for months every time I eat an orange and I put it in the freezer. The stuff that distills over is mostly water and a tiny bit of limonene. The limonene floats on top of the water. Once finished, I left the bottle on a table but after a while, it a film formed on top of the limonene. I placed the bottle in a freezer for now.

Poppy - 13-8-2012 at 10:33

Here they are! Ready to bake!

Obs.: Did you pickled the peels in small chips? Once you finish the distillation they would never come off the mouth of the baloon the way they are !

Mailinmypocket - 13-8-2012 at 11:19

Quote: Originally posted by Poppy

Here they are! Ready to bake!

Obs.: Did you pickled the peels in small chips? Once you finish the distillation they would never come off the mouth of the baloon the way they are !

Nice! You will have a much larger batch than I did

As for the skins I used a cheese grater to scrape the colored part of the skin off and then used a blender to pulverize it even further into a mash which looked like a bright orange stew in the rbf as seen in the first picture

The second picture is what the distillate looks like, you can see small droplets of oil sticking to the glass

The third picture is the yield from 5 large oranges after a DCM extraction of the distillate

*edit* Why are you baking the peels? Is it to preserve them for doing the extraction later on?

(sorry for the second picture being sideways, it's the only way the forum let me upload it)

[Edited on 13-8-2012 by Mailinmypocket]

Poppy - 13-8-2012 at 11:49

Quote: Originally posted by Mailinmypocket

As for the skins I used a cheese grater to scrape the colored part of the skin off and then used a blender to pulverize it even further

What? Did you scraped it directly from the fruit? It seems hard to pick the peels individually

Quote: Originally posted by Mailinmypocket

*edit* Why are you baking the peels? Is it to preserve them for doing the extraction later on?

No no.. noo! Haha its use of the habit I mean't "Baking" as referring to processing all this stuff.

EDIT: Between, my condesator is a Grahan Type, 600mm long. Guess the oil won't get stuck there, at least not if I process the whole of the peels?

[Edited on 8-13-2012 by Poppy]

Mailinmypocket - 13-8-2012 at 19:35

Ah! Of course, baking! lol

Just run the distillation for a bit after the distillate is no longer milky looking which indicates no more oil is coming over... The steam and water should flush out the residues that are in your condenser.

dennisfrancisblewettiii - 14-8-2012 at 02:10

Lemon pie. Lemon meringue pie. Lemon sherbert. Lemonade... mmm

[Edited on 14-8-2012 by Genecks]

Poppy - 14-8-2012 at 18:19

Alright I have now synthesized, from the aproximately yield of 12L of juice, more than 500g calcium citrate.

Mold is so cruel,it would consume all of the lemon contents in a matter of days, extracting the citrate was a priority!

Calcium citrate is a very low density substance, it forms upon heating lemon juice in a stainless pan to no less than 70 degrees celsius, and then throwing a 10% stoichometric excess slurry of calcium hydroxide and boiling water into it, filtering the content with a household strainer, and drying. Oil strainer suits best. Calcium citrate can be put to dry in the oven or open air.

The peels are two days old now. Hopefully the oil has not deteriorated. Tomorrow the distillation shall be carried out as by now I was privated of the proper supports for the apparattus, which were now provided.

If anyone's interested I'll post a picture on the citrate later on.

Quote: Originally posted by Genecks

Lemon pie. Lemon meringue pie. Lemon sherbert. Lemonade... mmm

[Edited on 14-8-2012 by Genecks]

Ah! and Grandma Saint Edwigs must certanly have dilicious recipes profiting from the usage of citric acid!!!

[Edited on 8-15-2012 by Poppy]

vmelkon - 15-8-2012 at 04:31

Quote: Originally posted by Mailinmypocket

Ah! Of course, baking! lol

Once I was finished with my oranges, I cleaned my 1 L flask, then added some water and distilled. It helps to clean the insides of the glassware (condenser, claisen adapter, glass stoppers, thermometer sidearm adapter).

[Edited on 15-8-2012 by vmelkon]

Ephesian - 15-8-2012 at 04:37

Quote:

Ok right now I have 249 lemons in my hands

Wow you must have very large hands

Poppy - 2-9-2012 at 07:26

OMGosh, blame on my parents. They threw away my lemon skins, in fact I took them out of the freezer to melt its ice, but forgot it for too long and in a matter of a single day it rottened :mad:

Below a pitcure of my distilling apparattus. A lot of trouble occurred with this, causing delays that untimately led to lemon skin failure.
For some reason the amianthus plate diminishes much the heating power of the flame to the point water drips veeery slowly from the tip of the condenser.

[Edited on 9-2-2012 by Poppy]

Poppy - 2-9-2012 at 07:26

double post

[Edited on 9-2-2012 by Poppy]

vmelkon - 2-9-2012 at 11:30

Is that a 3 L flask? I like the graham condenser. That is very long. As for the receiving beaker, I would use something that has a lower diameter to help the droplets of limonene coalesce. Remember that a lot of the distillate will be water and there will be very little limonene floating on the water. Some of the limonene will stick to the sides of the beaker and won't even rise to the top of the water.

Poppy - 2-9-2012 at 13:31

vmelkon,
That's a 1L flask. The two liters one, bigger, cracked on stading directly upon flame.
There must be a heating process which works best, like oil bath, sand bath or even copper powder bath someone has mentioned around. Guess there can be made a "poorman's" iron powder bath LOL

Whatever, distilling like that is unbelievebly crazy and some kind of solvent extraction must come in place.

Mailinmypocket - 2-9-2012 at 13:51

Try using a hot plate and making an air bath to heat the flask, you can make a tin foil tent around it to keep the heat in. Also, I would suggest getting one of these U adapters... It would allow you to run your graham condenser vertically. As it is, it won't perform perfectly since the condenser is at an angle. It creates these "traps" of condensate which make it hard to have a good flow of vapor.

Check here for the adapter mentioned!

Solvent extraction of citrus, in my experience, is annoying and difficult.. The result is always colored with fruit pigments and you need to mash it a lot and let it soak in the solvent. Then getting the citrus oil out of that is hard because you need to distill the solvent out to get a concentrate. The concentrate becomes this gunky stuff which is hard to clean, let alone get the oils out of.

Your set up looks good actually, all you need is one of those U adapters to properly attach the graham.

And also, grate the skins off the lemon with a fine grater. Its a pain in the ass but just shave the yellow off the lemons and then blend the skins in a blender into a paste. Add the paste to water and boil that in your distilling flask! I've always has great results

[Edited on 2-9-2012 by Mailinmypocket]

S.C. Wack - 2-9-2012 at 14:13

Google: ecuelle a piquer

Poppy - 2-9-2012 at 15:11

Alright seems the adptor is really needed indeed. Sometimes the condenser spills the loaded water like puke, its not anything even close to a constant flow.

As for the process Écuelle à Piquer, what a hell is this? How exactly it works?? Google says it requires a high speed motor and also one must elaborate the proper spikes, I think its promissing if ammounts like those 249 lemons are loaded each time.

Mainlimypocket, as you showed, the yield is quite high really, destillation may work fine.
As for solvent extraction, If suitable alcohol is used, you can soak that for a couple days, filter the zest, recycle the alcohol 5 or 10 more times, then bring the alcohol to oxydise with dichromate, this will make the alcohol evaporate as gaseous aldehyde, while the dichromate wont hurt the lemonene, since its just like a horned aromatic. What about it?

Lambda-Eyde - 2-9-2012 at 15:17

Quote: Originally posted by Mailinmypocket

Also, I would suggest getting one of these U adapters... It would allow you to run your graham condenser vertically. As it is, it won't perform perfectly since the condenser is at an angle. It creates these "traps" of condensate which make it hard to have a good flow of vapor.

Check here for the adapter mentioned!

Reading this reminds me of how pissed off I am at those cocks on eBay selling distillation kits with graham condensers mounted horizontally. Why the hell are they specializing in selling something they don't even know how to use?

[Edited on 2-9-2012 by Lambda-Eyde]

Mailinmypocket - 2-9-2012 at 15:34

Quote: Originally posted by Lambda-Eyde

Quote: Originally posted by Mailinmypocket

So stupid! They just try to mount something that looks as sciencey as possible. In this configuration a liebig would probably be the way to go.

Mailinmypocket - 2-9-2012 at 15:41

Quote: Originally posted by Poppy

Alright seems the adptor is really needed indeed. Sometimes the condenser spills the loaded water like puke, its not anything even close to a constant flow.

As for the process Écuelle à Piquer, what a hell is this? How exactly it works?? Google says it requires a high speed motor and also one must elaborate the proper spikes, I think its promissing if ammounts like those 249 lemons are loaded each time.

Mainlimypocket, as you showed, the yield is quite high really, destillation may work fine.
As for solvent extraction, If suitable alcohol is used, you can soak that for a couple days, filter the zest, recycle the alcohol 5 or 10 more times, then bring the alcohol to oxydise with dichromate, this will make the alcohol evaporate as gaseous aldehyde, while the dichromate wont hurt the lemonene, since its just like a horned aromatic. What about it?

Possibly, but I would just concentrate on extracting the oils as easily as possible (steam distillation, extraction of distillate with water immiscible solvent, separation, distillation etc) rather than muddle around with dichromate alcohol oxidations as well as try to get the target product at the same time.

If you can, there is nothing wrong with tilting the apparatus a bit and adjusting things a bit so the condenser is straight and the flask is at a bit of angle... The condenser is key... keep it vertical!

[Edited on 2-9-2012 by Mailinmypocket]

Poppy - 2-9-2012 at 16:23

Quote: Originally posted by Mailinmypocket

Quote: Originally posted by Lambda-Eyde

Quote: Originally posted by Mailinmypocket

So stupid! They just try to mount something that looks as sciencey as possible. In this configuration a liebig would probably be the way to go.

That aside some conical flasks with colored liquids in. The biggest mishap I found is the absurd price of a f*ckn support and rod around 80 bucks only for the vertical axis and nothing else!!! WTF
Had to build those myself lol
Btw one who mounts the graham in the diagonal must be halfway an idiot!

-------------------------
Pìcture: calcium citrate

Nothing special, thats the average yield from 1L of pure lemon juice, 60g. The lemons provided around 15L of juice.
The density of the citrate in fact is not that low: 1,4g/cm³

[Edited on 9-3-2012 by Poppy]

Quote: Originally posted by Mailinmypocket

Look, acetaldehyde boils at near 20°C, thats ridiculous, if you manage to pour the dichromate inside the alcohol you manage to produce moar of the aldehyde over the other possible product, the carboxilic acid, only then distilling the remaining concentrate. That would save a lot of losses ...

[Edited on 9-3-2012 by Poppy]

Poppy - 5-9-2012 at 15:43

New lemons have been bushed, only 59 this time.
Pics!
Forgive my lazyness, but thankfully the destillation method for extracting limonene has already been demonstrated, thus a solvent method has been applied this time. The skins were shred with a pair of scissors, and submerged in 1L approx. of 95% grain alcohol. This will be pickled in that jar for a month shaking everyday.
Firmly its seen a 3L yield from only 59 lemons, which gives each lemon an everage 50mL juice

You can see this juice is far from clear homemade lemonade composed of hand squeezed fruits, as it was all put in a blender and filtered the thicker chips only.

The last pic is the calcium citrate being washed. In an article entitled Manufacture of Calcium Citrate and Citric Acid from Lime Juice. (F. H. S. Warneford , F. Hardy Ind. Eng. Chem., 1925, 17 (12), pp 1283–1285) its described some compound oxydises during citric acid production and thus the salt must be throughly washed to give clear citrate salt. Actually, many of the coloring agents believely are includes charcoal, sugar and caramel, given the nauseating sweet smell coming from broken cell parts of the lemon fruitbody.

Obtention of citric acid by treatment of calcium citrate with dilute sulfuric acid has been hard a dick infernal pain as I can't determine the reaction worked or not, the articles tell more about extracting techniques but I have limited acess to this document :<

[Edited on 9-5-2012 by Poppy]

platedish29 - 5-9-2012 at 16:00

Cool.. What kind of lemons are those?

Poppy - 14-9-2012 at 12:49

Quote: Originally posted by platedish29

Cool.. What kind of lemons are those?

Not sure really.
EDIT: Citrus limonia Osbeck
-----

For the solvent extraction with ethanol, it failed. Not because ethanol was not apolar enough to do the job, but because at room temperature limonene makes an azeotrope with ethanol that evaporates faster than you can collect. When remais is the water from the skins with no smell at all, although the alcoholic extracted had a smell. I'll keep that, and see if the repels any mosquitos at all
lol

[Edited on 9-15-2012 by Poppy]