NurdRage - 2018-09-21
In this video we explore a bit of chemistry of the catalyst and verify that primary alcohols can't work and that some sort of catalyst i necessary. Tea tree oil is found to have lackluster but still promising potential as a catalyst. Related Videos: Using grignards to make tertiary alcohols: https://www.youtube.com/watch?v=EFQWD7-DCPI Using 7-hexyl-7-tridecanol to test if sodium production was even possible: https://www.youtube.com/watch?v=D4vDwQ4TyIc Previous lab notes on making sodium: https://www.youtube.com/watch?v=juWlrKdsjm4 Donate to NurdRage! Through Patreon (preferred): https://www.patreon.com/NurdRage Through Bitcoin: 1NurdRAge7PNR4ULrbrpcYvc9RC4LDp9pS Glassware generously provided by http://www.alchemylabsupply.com/ Use the discount code "nurdrage" for a 5% discount. Twitter: https://twitter.com/NurdRage Reddit: https://www.reddit.com/r/NurdRage/ Facebook: https://www.facebook.com/NurdRageYoutube/ Instagram: https://www.instagram.com/nurdrageyoutube/
1-Octen-3-ol is mosquito attractant, it's easy to get,unsaturated medium length secondary alcohol
So easy to get... if someone would have told Nilered before is long synthesis :D. Octenol could be a possibility. But as he sayed, it´s also an alkene and would maybe lead to side reactions and thus prohibit the reaction.
yeah, but I think hydrogenation of such alcohol wouldn't so difficult
but that´s not easy for the amateure
This whole line of research is awesome! Scientific rigor and a dash of humor. "Poor lithium." 😂🤣
thanks!
Thank you for all you do. You're taking remarkable steps toward opening certain avenues to the amateur chemist, and I truly appreciate it. This sort of thing is just fascinating, even if I never perform any of the reactions out of need.
Why thank you!
Please for moreee I live for these videos
What a wonderfully productive line of research this is! I can barely imagine the amount of sheer labor this represents, and wish to thank you for it all.
Not sure if tea tree oil will pan out. But we'll see, maybe i'll need to hydrogenate off the alkene group.
@Dustin Smith amines are gonna be harder to get for a hobbyist
@Sam Winfield I'd be curious to see if menthol would work despite the fact it's a sec alcohol
That's exactly what I was thinking! The cyclohexanols are pretty sterically hindered - which may be helpful - but terpinen-4-ol might be too hindered. There's also the possible curve-ball from the double bond. Menthol being fully saturated removes that complication.
It's worth considering the absolute configuration of the hydroxy group in menthol. It is effectively stereochemically locked by the greatly preferred equatorial orientation of the isopropyl group. This in turn affects the ease of elimination reactions involving hydrogen atoms adjacent to the hydroxy group. (Avoiding these elimination reactions is probably an important reason why tertiary alcohols are used. This suggests α-hydride elimination is the reason for primary and secondary alcohols failing to work. The Meerwein-Ponndorf reaction, for example, utilises α-hydride elimination from aluminium isopropoxide in the reduction of ketones.)
A close look at the theoretical ease of hydride elimination from menthol under the reaction conditions could save wasting time and reagents if it looks as though it really wouldn't work. And having thought about it, I get the feeling that menthol probably wouldn't work.
It would be lovely to be wrong about this...
Looking into this a bit more, linalool can be used in an easy preparation of terpin - a diol with two tertiary hydroxy groups.
"It can be prepared from other volatile oils like Geraniol, Linalol and Nerol by adding Dilute acids (5% H2SO4) to them. "
https://en.wikipedia.org/wiki/Terpin
Great to see a reagent coming from my own backyard :P
Okay, I'll stay cautiously optimistic...
Nope, not working, switching to super excited.
Wow, something that needs alchohol more than me.
i love your videos, it is interesting to see actual research being done. many other youtube channels, even many of the good ones, just go for the "i'ma do a science" rout without pushing things further. if it does not fit in 1-2 videos than it dies and they move onto something else. you on the other hand, publish much less frequently but with something to add. it is not just a cool reaction, it is something to learn.
why thank you!
Refers to the self as an amateur... lol
amateur with Ph.D. xD
@Blu Deat watch his equipment. I think you see the point.
yea I know his isnt doing it in pro laboratory or in university but in his backyard... but still it sounds little bit paradoxically :D
The term "amateur" simply means "one who does something for the love of it."
...which in slightly more modern terms means rather than being paid to do it, which is exactly the case here.
1. It seems like this reaction need alcohol with highly reactive conjugate base.
2. Probably the easiest accessable tertiary alcohol is citric acid, his sodium salt would eliminate problem with carboxylic group, but i don't know what is his solubility in non polar solvent and resistance for high temperature which can cause decarboxylation and dehydrogenation
If the sodium salt isn't soluble enough, maybe he could make an ester out of it, with ethanol for example. That way he could maybe protect the carboxylic group. Hydrolysation of the ester shouldn't be a problem as there is no water present in the reaction. I don't know whether the ester functionality changes it's resistance for decarboxylation
@Stan Albatross off course it's very good idea, but I was looking for the easiest way because he's trying to do this reaction makeable for amateurs and esterification especially in this reaction is very hard
@Marcin Kwidziński On had to try out. In the best cast case get citric acid with ethanol as educt and solvent and a sulfuric acid as catalyst. All easy to get chemicals. You could remove the water but not everyone has the needed glasware. But with that much access of ethanol you should get product, and the citric acid should be easy enough to remove as well as ethanol. All chemicals are easy to obtain and cheap
@Stan Albatross yeah but citric acid is sensitive even for catalytic amount of sulfuric acid what can cause decarboxylation, dehydrogenation and other damage to citric acid, so it ester should be made by other reaction
@Marcin Kwidziński But I like the idea. Maybe also try out tataric acid.
When the bubbler backflows, what enters the flask?
mineral oil since the bubbler is filled with mineral oil
Just rinse the sieve under the tap. You need more excitement in your life.
Great video. I really enjoy this lab note format.
Plant oils have different ingredients depending on place, weather, harvest time even if it's the same plant which it's never. Get accustomed to first purify your wanted substance from oils.
One crazy idea: What about using cellulose as the alcohol group donor? i know it can decompose at the reaction temperature and very probably fail while making a gooey mess, but hey paper is inexpensive.
Cellulose is only a secondary alcohol though. I'd be interested to see if something like phenol or catechol would work.
I don't think they would work, as aromates produce a tary mess in this reaction. Nurdrage found this out when trying to use tetrahydronaphtalin as a solvent.
@Safety Lucas I wouldn't call phenol amateur friendly. As far as I know phenol is neurotoxic. And from experience at work I can confirm that you have to quite careful when handling it
Does this qualify for a PhD thesis yet? I’ve learned so much from these videos, so thank you, thank you, thank you!!
I think it certainly qualifies for a journal paper.
This project is so neat! Keep up the great work!
I know you had some early trepidation about these "progress update" videos, so I'd like to reaffirm that I really enjoy them!
Did you try tert-Butyl alcohol?
Yep works just fine. But it's not as easy to buy as tea tree oil.
Sure, but I have it on hand that's why I asked. Thanks for your answer.
meganie8 I'd advise washing them /s
I know NurdRage said it works, but I tried this two weeks ago and had no success. I did the lithium drying step and let it run for three days. Seeing as t-butanol is the smallest tertiary alcohol, perhaps the sensitivity of this reaction to confounding factors is inversely proportional to the size of the alcohol.
1:27 Does the bottle on the left yell rude things at you drunkenly when you open it?
I love these lab notes videos! Always good to see how you tackle problems and figure out what the next steps should be.
I love these lab notes videos. Following the process of discovery makes it so much more understandable even though I'm not strong with chemistry.
This 'Lab Notes' series has been absolutely fantastic. Keep up the good work.
Excellent OTC research, really great to hear about your progress!
Great work, keep it up!! :)
I wonder if chlorobutanol would work even with the 3 Cl's. It's super easy to make from chloroform and acetone.
Wow so many up watched videos this is the first notification/ subscription notification I have gotten in months
Had you consider that the driving force for the magnesium reduction might be the MgO lattice energy?
Sorry, I was thinking about why lithium might not react as well or as rapidly as magnesium. How about a hydrocarbon soluble crown ether to complex and solubilize the Na+ ions.
The project seems to be really coming along nicely.
This is amazing, so your planning to buy tea tree oil and isolate the alcohol?You could also hydrogenate the alkene to an alkane with a nickel catalyst and test if it would work better.
@NurdRage I'd suggest trying linalool (either pure or using coriander oil), perhaps some phenols like thymol (can be bought pure on ebay) or eugenol (can also be bought pure, or from clove oil), and maybe some secondary alcohols like menthol (can also be bought pure).
And if you're willing to go for hydrogenation, try hydrogenating linalool too! (check that paper out, they do exactly that using nickel from old NiMh batteries! https://pubs.rsc.org/en/content/articlepdf/2008/gc/b806034g )
Maybe you could do some screening: by running the reaction on a much smaller scale, you can have multiple runs going at the same time, and test a whole variety of alcohols.
Have you though about trying phenol? It's relatively easy to make for the amateur.
Alternatively you could look into dyes. A fair number are tertiary carbocations that will react in situ with the sodium hydroxide to give tertiary alcohols.
Just came from @NileRed 's video on making phthalic anhydride from latex gloves and noticed the tertiary alcohol 2-ethyl hexanol is formed as a byproduct of the base ester hydrolysis of DEHP. Could this be extracted and used as a cheap and easily obtainable catalyst for this reaction? I would test it myself but, alas, my heating mantle is broken right now. Any thoughts?
I'm just here to watch the magic show.
Can you use linalool as well, it's a tertiary as well in lavender oil
That's a cool idea, although the two double bonds, one of them allylic w.r.t. the alcohol, probably won't help much.
Looking into this a bit more, linalool can be used in an easy preparation of terpin - a diol with two tertiary hydroxy groups.
"It can be prepared from other volatile oils like Geraniol, Linalol and Nerol by adding Dilute acids (5% H2SO4) to them. "
https://en.wikipedia.org/wiki/Terpin
Awesome video, love it
If your attempts with stearic acid work out then sunflower oil has some stearic acid and is high in oleic and linoleic acids which can be hydrogenated to form 95% stearic acid with the remaining 5% being palmitic acid.
Maybe try to mix tea tree oil with another alcohol like isopropanol
Exciting!
Good luck with the oil!
now i wanna know if thc works
Might as well get t-butanol in that case, much cheaper.
@NurdRage id say worth a try :D
no, cost is excessive. the point of this project is to make sodium accessible to the amateur, not push it further away with chemicals that cost hundreds of times more than the sodium itself.
Soa video on plants and radiation in hope to mutate it !!!
your are awesome!
The synthesis of potassium works also with 2-Butanol!
I can't afford magnesium because it costs me almost $100 for 1000 grams. I always wanted to make sodium metal from $1.5/kg sodium hydroxide but i can't 😥. If anyone here knows any other way to make good amount of sodium from sodium hydroxide then please let me know.
history in the making!
If tea tree oil will work as a tertiary alcohol, b/c it prevents elimination side reactions you should try eugenol, clove oil. A phenolic compound. Available in nearly 100% purity in natural food stores.
I think it is also more soluble than tea tree oil.
Aromatic groups tended to create a tarry mess, which is why he avoided them...
That tea tree oil business is amusing, would be fun to get it to work.
What about glycerol
It is 3 primary alcohols propane-1,2,3 triol
Was just about to ask the same. Might be worth a try.
primary alcohols don't seem to work for this.
Would Mentol work??
Calyo Delphi - 2018-09-21
Seriously dude keep it up with these lab notes videos. If anything they showcase the absolute objective rigor that you put into your research, and it's so wonderful to see the scientific method in action like this. <3
NurdRage - 2018-09-21
thanks!
wwwelkam - 2018-09-21
i second that