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Lab notes - Purified Tea Tree Oil Experiments for Making Sodium - October 13th 2018

NurdRage - 2018-10-13

In this video we purify tea tree oil by fractional distillation to extra to 4-terpineol. 4-Terpineol turns out to be a reasonably good catalyst for the sodium production reaction.

Related Videos: 
Using grignards to make tertiary alcohols: https://www.youtube.com/watch?v=EFQWD7-DCPI

Previous lab notes on making sodium involving tea tree oil: https://www.youtube.com/watch?v=v7o3ZfX0BQc

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#sodium #4-Terpineol #TeaTreeOil

TheQwarx - 2018-10-13

I have to say following this project has really been the best chemistry content I've followed in YouTube (or anywhere else) and I've just to thank you for that, your channel pretty much is what drove me to study chemistry. I don't know if making these kinds of lab notes videos take more or less effort than the kinds of you've usually made, but in my opinion these have been incredibly interesting to follow and to watch. Keep up the good work, these bigger projects like with the pyrimethamine synthesis have just been excellent to watch

NurdRage - 2018-10-13

why thank you!

Mora Fermi - 2018-10-14

I wish this kind of content existed when I was studying chemistry! It sure would help keep the interest flowing during all the slog...

David Fontenot - 2018-10-16

NurdRage has always made awesome video's that inspire a lot of people to give chemistry a try and he makes the video's in a way that just about any one can understand them.. As always great work NurdRage and keep it up...
There have been quite a few decent chemist's that have lost their channels or stopped making video's due to youtube strikes, if you enjoy chemistry content like this please like, share, subscribe and let youtube know that this is what we want to see ..

NurdRage - 2018-10-13

Lab gods, do what you must, for we have already won.

bormisha - 2018-10-19

Andy Lee Robinson, he is already a PhD.

nybotheveg - 2018-11-08

Have you considered hydroxylating the terpineol with sulphuric acid and water? It would get rid of the alkene functionality and introduce another tertiary alcohol center? It might be interestering to see how the diol would perform.

Alexander Baca - 2018-11-21

@Nurdrage it would be really cool if you could show an at home synthesis of pure magnesium metal!

bormisha - 2018-11-21

id523a, "exotic tertiary alcohol that any amateur chemist would have to buy specially" it may be even worse, such alcohols may not be available for sale to private people and be boring enough for the black market not to stock them either. The only solution may be to do it yourself, which is way harder than making sodium (and you will need sodium to perform that reaction in the first place). Honestly, I'd opt for the 'hot', non-catalyzed variation of the process if I were to try to reproduce it.

Ankit Nandi - 2019-04-01

I think the amount of catalyst used was proportional to the amoum=nt of magnesium used. Otherwise, a greater amount of catalyst would not have decreased yield. Keep it in mind next time.

twocvbloke - 2018-10-13

The lab gods will now send a plague of suicidal flies to ruin all future experiments... :P

Terminus Est - 2018-10-13

Meh not to worry. He can always put lots of fly paper around and keep his lab equipment sealed with paper towels. :P

RagingHammer - 2018-10-14

Next, the lab gods shall send beetles

Zivilyn The Wyrd - 2018-10-14

@RagingHammer Beeeeeees

Jon Black - 2018-10-13

This is by far the best documentet chemistry project suitable for amatures in video format in my opinion!

NurdRage - 2018-10-13


adfaklsdjf - 2018-10-14

It's fantastic. I've never done any chemistry, and making pure sodium is such a fun goal, these videos have me thinking about starting..

xuNsh1ne - 2018-10-13

Next: Potassium, Rubidium, Caesium :)

Mr Slinky dragon - 2018-10-14

@Karsten Hoff i wonder if that would work with the other group 1 metals

Karsten Hoff - 2018-10-14

@Mr Slinky dragon he also makes potassium from Na and KCl in the same way. Francium is obviously impossible

AllChemystery - 2018-10-17

Theres a few videos on making potassium and cesium on my channel. Its not exceedingly difficult if you have the equipment.

bormisha - 2018-10-19

Maybe also Francium?

AllChemystery - 2018-10-19

bormisha Nope. Francium requires a very expensive and highly specialised, hi tech lab to produce. And it’s unstable lasting hours before decaying.

10bee - 2018-10-13

How much of metallic sodium have you collected from all runs by now? :)

Eric Pham - 2018-10-13


Mylitla - 2018-10-14

I sure hope you plan on submitting a paper on your findings. You deserve some professional credit for your creativity and hard work.

RagingHammer - 2018-10-14

damn right he does

That One Slayer Fan - 2018-10-14


Edy Marin - 2018-10-13

I wonder how much sodium does he have.

Tom's Lab - 2018-10-14

How much sodium have you amassed in the course of these experiments?

Cooper Frazier - 2018-10-13

Why not use a vacuum distillation to reduce the boiling temperature?

Grak70 - 2018-10-14

I think he's trying to keep it accessible to a bigger group of amateurs. Vacuum distillation is a time consuming pain in the ass, not to mention your pump exhaust is going to make the whole house smell like an extremely pungent foot massage. :-)

William V - 2018-10-17

Grak70 with a scroll pump/diaphragm pump, the exhaust can be run through a condenser of sorts. Not much vac would be needed for a quality fractionation

Grak70 - 2018-11-14

William V well I tried this distillation myself and boy was it a mess. First off, water left over from the steam distillation bumped for a good hour, then thermal decomposition produced some impressive lacrymators! The acrid stink is incredible. I guess I’ll try vacuum distillation after all! At 30torr it should boil over around 90-95C and not decompose. I dunno how NurdRage did this without getting acrid black tar in his bottoms fraction.

TheDoctor - 2018-10-13

I would love to see if you can hydrogenate the tea tree oil using equipment other than a commercial hydrogenation apparatus.

Ryjelsum - 2018-10-14

I think he's working towards it - posted something on twitter about nickel chloride which can be used as a hydrogenation catalyst. He also made a tweet that said "OMG THIS NEW CATALYST IS AMAZING!!!" so I'm sure there's at least one or two new lab notes videos down the line about both the hydrogenation and whatever this mystery new catalyst is, if it's related to this project.

Jon Black - 2018-10-14

If nickel chloride is involved as a hydrogenation catalyst I assume it´s a urushibara nickel type catalyst, and yes they are amazing!

AguaFluorida - 2018-10-14

Yep, Urushibara is the way.

TheDoctor - 2018-10-14

@AguaFluorida Yeah Baby! Bring it on!

Ryjelsum - 2018-10-15

Cool! I am only in year 2 of my college education in this sorcery, so every discovery he makes along this path of research results in me learning like five new things. I'm loving this series, and honestly, following his twitter too. :)

The Crude Lab - 2018-10-13

NurdRage wins the noble prize for finding easy way to extract sodium!

Awsomiihill - 2018-10-14

imagine the smell in the lab after he opened that bottle of tea tree oil

Eric Wolf - 2019-06-17

you would NEVER get that smell out

OakC - 2018-10-13

I may have missed out on the giveaway, but we all receive the far greater prize of your sodium production process. It has been great being along for the ride.

Alex Potts - 2018-10-13

This has been great to watch from beginning to end. It's so rare to see real research being carried out on YouTube like this.

I'm wondering what your next big project will be.

Laharl Krichevskoy - 2018-10-13

If you need a more powerfull heater you can use one of those electric ceramic heaters with the resistor at plain saight that gets red hot. Those exist well over 1000W. You can drill a hole in the middle and inser a thermocuple to regulate it by hand or get a thermocouple kit for arduino and use an arduino to do it for you.

David W. Smith - 2018-10-13

Hey, have you considered a slow continuous drip after the initial 5ml of the catalyst, so that in each hour the percentage of un-degraded catalyst stays the same and the reaction continues instead of requiring a piecewise addition at 20h?

TheIdeanator - 2018-10-14

Hell yeah! This has been my favorite series for quite some time.

CarlitoNZ - 2018-10-13

haha i see the light at the end of the tunnel, Thanks for all your hard work !!!

mark wellman - 2018-10-18

Amazing Job keep up the good work, just got a new house w/ basement this is a must try!

Gareth Dean - 2018-10-14

Youtube: Here's the latest movie reviews.

Me: Eh.

Youtube: Here's a quarter hour of lab notes for something that lets you do something else.


Josuel Servin - 2018-10-14

It's been a great ride, and I'm glad you have archived a great result I hope the lab gods smile upon your glassware and you can perfect the process even more!

ejkozan - 2018-10-13

As for 4-terpineol... Maybe we don't need to make hydrogenation. What if we make simple acid catalyzed water addition to the double bond, and make double tertiary alcohol? In theory, it is just some cooking in diluted sulfuric acid. What do you think?

EDIT: after some search, I can say, that a lot of terpenes and terpenoids after treatment (some cooking) with diluted sulfuric acid rearrange to stuff similar to terpin. I feel that we can do that with crude tea tree oil, and products of this reaction would be just tertiary alcohols. If so, this would be robust, cheap catalytic system easy to obtain for any hobbyist.

NurdRage - 2018-10-14

Yeah that ain't working. i left it for three weeks now and nothing is coming out.

ejkozan - 2018-10-14

Sad information :/ But still I hope that something can be done in this direction.
For now: keep going! Wonderfull work which is getting better with each video :)

TMoD7007 - 2018-10-14

/edit: ignore that if obsolete! ;) I answered to an older reply! ;)

Quite some awesome wording to savour in these papers! ;) The German language is superbly capable for describing complex matter, but it's far to difficult for international cooperation in science...

Can you specify what you want to know exactly? Or could you point me to a relevant section that is unclear to you?

There is quite some interesting but in this case irrelevant clutter in there. The older source from 1907 starts like the equivalent of a scholar diss track against a guy named Semmler... ;)

ejkozan - 2018-10-14

Old publications had soul XD There should be a section about water addition to a double bond, but I was not able to pin it down :( Maybe there are "magic conditions" which would work. As @NurdRage wrote, just stirring for prolonged time don't work.

TMoD7007 - 2018-10-14

The 1907 publication just handles some criticismby this guy Semmler in an explanation why they are nonsense in the authors opinion. The author got the nobel prize for exactly that research topic, so it seems to be top notch of its time! ;)

It's not about water addition but hydrogen halide addition. Discussing melting points and possible arrangements resulting in different melting points and how the Halogen compounds can be considered evident if this or that other compound can also be detected. Bold deduction considering the analytic capabilities of the time without NMR spectroscopy, etc....

I'm reading the second one later.

liam gil - 2018-10-13

this has been my favorite series of videos on your channel. Haven't gotten to OCHEM yet, so I'm never entirely sure whats going on, but I really enjoy seeing your process.

Blake Lee - 2018-10-14

I'm in Ochem and I still am not quite sure whats going on 😂

piranha031091 - 2018-10-13

Congrats man! Looking forwards to the final video, where you sum up all that!

Zakrana Epsilon - 2018-10-20

I have seen you used Magnesium As Your Reactive Metal! Because it Was Mainly Used In Grigned Reaction! But Calcium Are A Little Reactive! You should Try Calcium

lm5050 - 2018-10-14

this has been an amazing series thankyou so much for your fantastic contributions to amateur chemistry hobbyists

r.m. renfield - 2018-10-13

Watching you go through this process of discovery is fascinating stuff. I'm happy you've broken the back of this problem but also glad you're going to exhaust the other options as well. Great videos, mate.

NurdRage - 2018-10-13

Why thank you!

Ryan Owens - 2018-10-15

I have really enjoyed this series, I like that you really showed a lot of background work and hurdles.

PartVIII - 2018-10-14

@NurdRage please take a TLC of the reaction mixture. I suspect magnesium is coordinating with the alcohol and alkene.
Alkenes also love undergoing radical condensation/polymerization/dimerization. I'm curious whether it formed a bridged ether or polymerized.

zacariah heim - 2018-10-14

This is amazing, i sincerely thank you on behalf of all humanity for your gift of openly sharing the formula's and your work!! This is amazing!!! Also.... this could potentially make sodium batteries faaaarr more economically viable!!! ooooo antsy

hoseja - 2018-10-13

Citric acid is a tertiary alcohol xD

aga - 2018-10-13

So it has to be a tertiary alcohol with just 1 -OH group ?
If all those O= knocking about on TSC pose no 'polarity' problem, what about asprin ?

6alecapristrudel - 2018-10-13

Maybe a tri-ester would be able to dissolve in the mineral oil and survive given that the solvent is dry so no hydrolysis can happen?

6alecapristrudel - 2018-10-13

Oh yeah, silly me. This kind of hydrolysis doesn't really need water to work lol.

Grak70 - 2018-10-14

Even if the base doesn't, sodium will completely deprotonate the acid as it's produced, causing it to salt out.

Amcia Apple - 2018-10-17

AFAIR Aspirin decomposes on contact with NaOH

DrJohnnyLemonhead - 2018-10-14

Thank you man, this is fantastic fundamental and original work for amateurs. It’s been a riveting journey and looking forward to where this goes.

Truman Burbank - 2019-03-17

Amazing chemistry skills.

Jafeth Méndez Gómez - 2018-10-14

Great job man, congratulations.

G - 2019-07-23

I'm a bit late to the party but once on board, I sat and watched this series from wire to wire. GLUED. 2 enthusiastic thumbs up!

Salman Abdullah Idrees - 2018-10-14

wow after my last video i watch was 2009
now i'm back again after 10 years

Chris Armour - 2018-10-14

Your lab must smell great now! :-)

AVIONN2 - 2018-10-13

Man ive been so excited for this tea tree oil vid

Jehu McSpooran - 2018-10-18

Loving your work. This is brilliant. I'm now wondering if adding the 4-terpineol in a constant metered dose would decrease the amount used as it would not decay like when it is dumped in all at the start. And then someone needs to figure out a replacement for dioxane.

That One Slayer Fan - 2018-10-14

Oooh shizzle, we’re clooose!

Kahleeb - 2018-10-14

Wow! This is so exciting!

Nandakishore Santhi - 2018-10-14

Wonderful work! Congratulations.
Don't remember if this was already tried or discussed: would glycerine/glycerol work as the alcohol catalyst? Looks like it is classified as either a primary or as a secondary alcohol, but due to its somewhat peculiar structure it might work?

Seven Proxies - 2018-10-14

This project is awesome. Frankly I think similar projects should function as introduction experiments in chemistry classes for bored high school students.

The teacher coming up with a mission of how to use easily accessible and cheap components refined into a more difficult product.

I think it would work as a very good "hook" to get the students attention because it would demonstrate how chemistry is useful in practical context that the beginner can understand.

When you begin by exposing students to theory and facts (as many chemistry teachers do), many students often question the usefulness of the information. If they have any interest at all, it's usually just about passing tests.

puckay - 2018-10-13

Time for some more suicidal flies I guess :)

O - 2018-10-25

I remember a time when Darth vader was the narator

Amos Backstrom - 2018-10-14

Awesome man. I hope to attempt this eventually

Dalton Growley - 2018-10-14

these videos are super interesting even to non chemists like myself

Pietro Tettamanti - 2018-10-13