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12thealchemist
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Quote: Originally posted by stamasd  | | Quote: Originally posted by 12thealchemist | | If you're doing NurdRage's sodium metal production reaction with borneol, it is possible that camphor may work, if a hypothesis of mine is correct. I
hypothesise that it is the enolate that is the active catalyst, and borneol (or another secondary alcohol) is just a pre-catalyst. The enolate would
be formed from the corresponding ketone via alpha-hydrogen elimination. |
I know of one way of testing that hypothesis.  But I need borneol for that. 
(7 years of graduate school has taught me the importance of controls)
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This is very true. However, since NurdRage has already tested borneol, it is not inconceivable that it would work under the slight modifications you
would be using. On the other hand, it is better to do a small amount of good science than lots of bad science.
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stamasd
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One problem with using a shortcut would be, if it doesn't work I won't know if it's a problem with the reaction mechanism, or with my technique. I
need a positive control, as close as possible.
[Edited on 13-12-2018 by stamasd]
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12thealchemist
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That is a very good point. Once you establish that you can replicate the reaction, while it would be interesting to see if camphor works, it is
entirely up to you.
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stamasd
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So I received today the "borneol" I had ordered from India. What a surprise, it's not borneol. It's camphor. It looks like camphor, it smells like
camphor; if I put this and a sample of camphor next to each other I cannot distinguish them by appearance or smell. Moreover the package it came in is
labeled "camphor" and the invoice included has "camphor" handwritten. In a few days I'll have time to determine its MP and conclusively prove it's not
borneol.
Scratch this source.
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Σldritch
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Dithionite reduces ketones to alcohols and can be bought as a reductant for indigo. The hard part would be choosing a suitable solvent.
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stamasd
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| Quote: Originally posted by Σldritch | | Dithionite reduces ketones to alcohols and can be bought as a reductant for indigo. The hard part would be choosing a suitable solvent.
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According to unionist's post on the first page it is known not to work for camphor.
I don't have dithionite (though I could get some easily) but I do have some amino(imino)methanesulfinic acid (AKA thiourea dioxide) and could try it
sometime next week, when hopefully I will have some time to attempt the Urushibara reduction too. I assume an alcohol should be a suitable medium for
the reaction.
[Edited on 21-12-2018 by stamasd]
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unionised
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These
"known not to work" and
"The hard part would be choosing a suitable solvent."
May be two ways to say the same thing.
The paper I cited says it fails because the camphor sublimes out of the mixture.
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stamasd
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| Quote: Originally posted by unionised | These
"known not to work" and
"The hard part would be choosing a suitable solvent."
May be two ways to say the same thing.
The paper I cited says it fails because the camphor sublimes out of the mixture. |
I agree, that's why I'm willing to try it.
Probably in a reflux setup so that the refluxing alcohol can bring back the sublimated reagent.
http://reag.paperplane.io/00002692.htm
[Edited on 21-12-2018 by stamasd]
[Edited on 21-12-2018 by stamasd]
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Σldritch
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Sorry i just skimmed through the thread and thought it was mostly about Sodium Borohydride. Having read it again i suggest you separate the borneol
and camphor by simply polymerizing the ketone in alcoholic hydroxide for a while and then filter off the resulting crap and distill/sublimate out your
product.
I was about to suggest Thiourea dioxide too until i opened that link last second.  I think there is plenty of ways to reduce ketones to alcohols but i can not remember any more now.
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zed
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Ummm. Read Na procedures. Borneol worked the best .
Sadly, best online Camphor reduction procedures, explored so far, require Borohydride.
There are some Chinese patent postings... utilizing MPV, but they are more or less unintelligible.
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XeonTheMGPony
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https://www1.eere.energy.gov/hydrogenandfuelcells/pdfs/revie...
http://www.sciencemadness.org/talk/viewthread.php?tid=3151
Make some NaBH4
thankfully I have a bottle of distilled trymethelboride
[Edited on 8-1-2019 by XeonTheMGPony]
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icelake
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Too good to be true?
https://www.jstor.org/stable/pdf/25138688.pdf
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oberkarteufel
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Rather not.
Sodium in alcohol seems like very plausible way to reduce a ketone. However, we're using sodium to produce borneol to produce sodium 
So I think my idea from the first page of using Na-MgO aggregate is slightly more effort-effective.
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icelake
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True, but Nurdrage's method requires few grams of sodium jump start anyway (to protect Borosilicate glassware).
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judithwright
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Sodium borohydride is likely to be the easiest option by far.
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XeonTheMGPony
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https://www.youtube.com/watch?v=XxCIVTdXWQU
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oberkarteufel
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Trust me - everyone truly interested in this topic has already seen this update
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XeonTheMGPony
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Gotta make sure! I been downloading every single one since you tube proved less then reliable stewards of knowledge.
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zed
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2 days? Hardly anyone had seen that update!
Thank you, Xeon.
So it seems, folks online, are claiming to be selling Borneol, but they aren't?
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TheOtherKindOfDoc
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zed
I found a seller on alibaba, "Shandong Look Chemical Co., Ltd". They seem legit, and I ordered borneol from them. Just some issues, first they have a
minimum order size of 1kg, which is kind of a lot when you are using it as a catalyst for a hobby. Second, it is not cheap, cost me $200 including
transport.
3rd, and most importantly, I cannot yet vouch 100% for the authenticity of the borneol. It does smell somewhat different from camphor, and the
crystals are different, but testing the melting point turned out to be a bit tricky.
I made some 1,4-dioxane today (pending purification) and will let you know if I can recommend them as a supplier when I have time to go through all
the remaining steps.. If I get the Na production going it will be a pretty definite confirmation that it is indeed borneol.
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Endo
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| Quote: Originally posted by stamasd | So I received today the "borneol" I had ordered from India. What a surprise, it's not borneol. It's camphor. It looks like camphor, it smells like
camphor; if I put this and a sample of camphor next to each other I cannot distinguish them by appearance or smell. Moreover the package it came in is
labeled "camphor" and the invoice included has "camphor" handwritten. In a few days I'll have time to determine its MP and conclusively prove it's not
borneol.
Scratch this source. |
I had this exact same experience with "Borneol" from the Ping Jian (India) same seller. Same labeled invoice as camphor, and an explanation from the
seller indicating it is borneol and that they use camphor as a name interchangeably.
Melting point was not crisp and I was not able to use MP to discern between the two. I noted that the density differences should have borneol heavier
than water and camphor lighter than water. Distilled water, at exactly 20C and a small crystal carefully pushed beneath the surface (no clinging
bubbles) slowly drifted up to the surface of the water.
I tried the half mole reaction with lithium as a jump start and was able to get product, however it took three days and an added addition of the
'borneol' catalyst at day 2.
A full mole run a few days later with both menthol and suspect "borneol" gave much better results and finished in a bit more than two days with better
product.
Good Luck!
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