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MrHomeScientist
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I think he's just upset this reaction can't be done with bleach and vinegar. He needs a title like Anders...
I did another run yesterday, using lower-boiling (~210C) Tiki torch fuel. It supposedly contains citronella but is colorless, unlike the yellow stuff
you usually find. The hope was that this would give more agitation from boiling, but it didn't really seem to make a difference. I'm starting to think
my thermocouple in the sand bath is reading a much different temperature than what's in the reaction flask, despite me placing it right outside the
flask.
Fairly routine reaction overall with little difference to my other runs - I'll inspect the products sometime in the next few days.
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blogfast25
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Agreed.
EC1: he's unlikely to accept you as an unbiased experimenter.
Interestingly, there's a US Patent (1,978,647) that describes the preparation of anhydrous, relatively pure (free of hydroxide) Na or K alkoxides from
the alkali metal hydroxides. Reaction of the MOH with an excess of the target alcohol, followed by precipitation of the anhydrous alkoxide by mixing
in anhydrous acetone. Sounds very doable. The 'Organics' contributors seem to swear by it...
[Edited on 17-4-2013 by blogfast25]
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MrHomeScientist
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Quote: Originally posted by AJKOER  | OK, no I am not upset, in fact, I am laughing hard.
But, I understand a good many of the followers on this thread worship at the altar of Magnesium as a great reducer or something. It does have a lot of
blinding flash, I give it that.
So it doesn't matter that I have revealed your prophet is a follower of someone who is even more clueless than the original author of the background
patent (blasphemy, I know).
The amount of ridiculousness you are willing to accept to preserve your false Mg god is inspiring (in plain view of patent inconsistencies on how it
could ever work, other peer reviewed research noting the power of Mg in CH3OH, a known creator of an active form of H2, not Mg, that I referenced
(some little known chemical journal), but excuse me while I laugh, and laugh, and laugh, after all, you have your 'authority' (but, may I dare
recommend, that you teach him how to balance and write at least two full equations).
And, do want to see magic? Cut your Mg dose in half (relative to KOH and ROH) and your false god is totally revealed. But none of you will, you are
devout mindless followers. It would be simply too irreligious, unthinkable.
But today is a new day, any more funny explanations (I noticed how you skipped over the small issue of K not reacting at all with water, vow, you are
a true devotee). I know, I feel bad, I shouldn't make fun of people with mindless convictions, so I just leave now and laugh privately.
I would recommend, however, that this thread be moved to Organic Chemistry section. They have the right to know that you are making fun and
discounting one of their gods - Hydrogenation (something about a Noble prize in Chemistry). Like we could have a 100 year religious war or something
(wait, we have already had one of those).
[Edited on 17-4-2013 by AJKOER] |
This post is the perfect example of the defeated "internet arguer." "Laughing" at our supposed ignorance, claiming someone's theory is "religious,"
and offering no real input of your own are the hallmarks of a bad (some might say trolling) post.
If you are so adamant about it, please conduct the experiment you propose. You can't really demand that we persue your own personal theory. We were
all able to get the chemicals, and so can you. Don't be an armchair chemist - anyone can balance equations in a vacuum, but the real value is testing
things in real world conditions. Personally I'd love to see more data about this reaction. Currently I'm focusing on improving coalescence in my
product, rather than exploring alternative hypotheses. I want to get the process down properly before branching out.
I recommend this whole chain of posts (including this one) be sent to detritus. It's clogging up an already tremendously long thread.
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blogfast25
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We'd all like to see more data about this reaction, Mr HS, but they're unlikely to pop up real soon, considering the resources needed for just one
run.
I've just found some isoamyl alcohol (3-methyl-1-butanol, the longest chain alcohol I've got in my larder), very dry, so I might try that patent to
synthesize the potassium alkoxide from that...
[Edited on 17-4-2013 by blogfast25]
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Nicodem
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Thread Split
18-4-2013 at 11:12 |
Nicodem
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Thread Split
18-4-2013 at 11:18 |
Nicodem
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WARNING: I don't want to hear another word about "nascent hydrogen" here!
The next member that tries to troll in this thread with such crackpot ideas will be sanctioned by posting-right suspension.
Is it possible that nobody noticed this thread already has 53 pages of posts, many of which are utterly unnecessary? The last thing we need here is to
feed trolls that come out with baits as idiotic as "nascent hydrogen".
I invested a lot of work to split of the dozens of these posts by AJKOER and replies to him. I'm sure I made some injustice to some replies that may
have contained other information and some of the posts left here clumsily refer to split off posts, but it is certainly better this way. I left the trolling thread active in Whimsy so that those who like to feed AJKOER can do so without harm to the scientific part of the forum.
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bfesser
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Thank you for all your hard work, Nicodem. It's appreciated.
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AJKOER
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First a review of my take on how the overall reaction is proceeding.
Aqueous phase since as much as 27% of KOH could be water:
Mg + 2 KOH + H2O --> [K2MgO2 + H2O] + H2* (g)
K2MgO2 + H2O <---> 2 KOH + MgO
Net:
Mg + H2O --KOH--> MgO + H2* (g)
Non-aqueous reaction:
KOH + ROH --> ROK + H2O
Mg + H2O --KOH--> MgO + H2* (g)
ROK + 1/2 H2* <---> ROH + K (s)
Net:
KOH + H2O ---> MgO + K (s) + 1/2 H2*
------------------------------------------------------
Comments: Per Wikipedia (http://en.wikipedia.org/wiki/Tert-Butanol ), to quote:
"For example, the commonly used organic reagent potassium tert-butoxide is prepared by refluxing dry tert-butanol with potassium metal.[5]
K + tBuOH → tBuO−K+ + 1/2 H2
The tert-butoxide species is itself useful as a strong, non-nucleophilic base in organic chemistry."
So, what I am postulating here is that activated hydrogen is formed (most likely via chemisorption, discussed more below) and that with excess H2*
(from the initial dehydration) and also pressure (balloon employment) the ROK formation reaction is reversed to some extent:
ROK + 1/2 H2* ---> ROH + K (s)
Now, more on this chemisorbed hydrogen most likely created via the presence of MgO. Here is an abstract (source: "H2 chemisorption and consecutive UV
stimulated surface reactions on nanostructured MgO", in Phys. Chem. Chem. Phys., 1999,1, 713-721 (link: http://pubs.rsc.org/en/Content/ArticleLanding/1999/CP/a80844... ). To quote from the abstract:
"MgO nanoparticles obtained by chemical vapour deposition (CVD) were exposed to H2 and subsequently to UV irradiation and/or molecular oxygen at room
temperature. A combined IR/EPR study reveals the role of low coordinated surface sites and anion vacancies in the diverse reaction steps. The hydride
groups emerging from the initial H2 chemisorption processes (heterolytic splitting) play an active role in the consecutive reactions. They provide the
electrons which are required for the UV induced formation of surface colour centres and for the production of superoxide anions (redox reaction). Both
the colour centres and the superoxide anions are EPR active. The hydroxy groups resulting from H2 chemisorption do not actively participate in the
consecutive reactions. Together with the OH groups formed in the course of colour centre formation they rather play the role of an observer. They
undergo specific electronic interactions with both the colour centre and the superoxide anion which are IR inactive (or IR inaccessible) surface
species. They may, however, be observed by IR spectroscopy via the specifically influenced OH stretching vibrations. This proves the intimate
interplay between IR and EPR spectroscopy as applied to the surface processes under investigation. As a result, two paths were found for the three
consecutive surface reaction steps: H2 chemisorption, colour centre formation and superoxide anion formation. In the first one a single, well defined
surface area element is involved, namely a low coordinated ion pair, the cation of which is a constituent of an anion vacancy. In the second path a
diffusion controlled intermediate step has to be adopted in which the electron required for the colour centre is transported by an H atom travelling
from a hydride group to a remote anion vacancy. In either case there is clear experimental evidence that the finally resulting superoxide anions are
complexed by the colour centre cations."
See also "Theoretical aspects of H2 and CO chemisorption on MgO surfaces", Surface Science (May 1982), 117 (1-3), pg. 571-580 at http://journals2.scholarsportal.info/details.xqy?uri=/003960...
to quote from the abstract:
"Preliminary ab initio calculations at the SCF level and beyond are reported for the chemisorption of H2 and CO at the (001) surface of MgO. It is
concluded that the dissociative chemisorption of H2 requires the presence of defects and that at anion vacancies, V− centres and self-trapped
holes the overall process is exothermic in each case. It is predicted to be non-activated at anion vacancies and possibly the same at the other two
defects. Binding energies are calculated for the interaction of CO with a non-defective (001) surface of MgO and at impurity ions therein. They range
from 2.5 kcal/mole at Al3+ to 20.8 kcal/mole at Cu2+ and are shown to be highly sensitive to lattice relaxation of the defective surface."
where there is an interesting reference to the role of impurities in the MgO.
Now, there are also so studies citing the reaction of between hydrogen and magnesium, but mostly as fine Mg powder (or nano). However, Mg surface
attacked by KOH, may be more amiable to H2. Probably, an important speculation is that absence MgO, no or reduced chemisorbed H2 formation, no
reduction reaction and no K is produced! Also, less than completely pure Mg, KOH or KOH, could produce detective surfaces on the MgO, increasing
yield.
I would speculate that MgO dust on Mg turnings may provide a good contact point for gaseous H2 and, with infrequent stirring to add ROK, help to form
potassium. Neither frequent or very infrequent (in agreement with the patent instructions) would be advisable.
Now why is Mg dust no good for this reaction? My speculations, first, the reaction rate would be too fast (also more heat) and limit gaseous contact.
Also, absence the Mg turnings, less support for formed MgO thereby limiting the H2 contact.
[Edited on 19-4-2013 by AJKOER]
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AJKOER
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So What Happens with Reduced Mg Input (or too much water)?
So for the non-aqueous reactions, we double the 1st equation to increase the water, and leave the magesium & water equation unchanged:
2 KOH + 2 ROH --> 2 ROK + 2 H2O
Mg + 2 H2O ---KOH---> MgO + H2O + H2* (g)
2 ROK + H2* <---> 2 ROH + K (s)
Net:
2 KOH + Mg ---> MgO + H2O + K (s) --> MgO + KOH + 1/2 H2 (g)
In other words, possibly zero yield on the potassium assuming full mixing occurs.
Interestingly, this result is not predicted by Blogfast (a suggested test of paths).
[Edited on 19-4-2013 by AJKOER]
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AJKOER
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Substitutes for Mg (MgO)?
Based on my presumed reaction mechanisms, are there any potential substitutes for Mg? To answer, I refer to Wikipedia on chemisorption (link: http://en.wikipedia.org/wiki/Chemisorption ), to quote:
"Due to specificity, the nature of chemisorption can greatly differ, depending on the chemical identity and the surface structure."
So, the apparent answer is there is, indeed, something special about Mg (MgO) and potential substitutes would be hard to come by.
Research appears to indicate, however, that Al2O3 with SiO2 and Fe may be a candidate fulfilling part of the requirements. This is based on a review
of some related research, for example, "Connection between Chemisorption Kinetics and Adsorption Equilibria of Organic ompounds on Oxide Surfaces†",
link (full paper is available): http://oscar.chem.ccu.edu.tw/~wugol/references/afile/Langmui... To quote from the paper:
"The Bronsted and Lewis acid-base sites are the main types of active sites on SiO2, TiO2, Al2 O3, and other pure and mixed oxide surfaces in different
chemisorption and catalytic transformations of organic compounds. The kinetics of organic reactions with OH groups of a silica surface is one of best
investigated cases among these oxides.1,2 It was established that one occurs through two main mechanisms, namely, electrophilic substitution of
hydrogen of this group by organic residue (SEi) and nucleophilic substitution of OH groups by this residue (SNi(Si)). Formation of precursors (linear
hydrogenbonded or cyclic donor-acceptor complexes between organic molecules and surface groups) have been proposed in the first stage of these
reactions.1,2 Of course, total activation energies, rates, and selectivities of surface reactions strongly depend on the precursor stability."
Another work, "Hydrogen Chemisorption on Al2O3-Supported Gold Catalysts" published in "J. Phys. Chem. B, 2005, 109 (30), pp 14581–14587, Copyright
© 2005 American Chemical Society. To quote from the abstract:
"Hydrogen is dissociatively adsorbed on the gold particles in Au/Al2O3 catalysts, as demonstrated by a combination of in-situ X-ray absorption
spectroscopy, chemisorption, and H/D exchange experiments. This chemisorption of hydrogen induces changes in the Au L3 and L2 X-ray absorption
near-edge structures. The gold atoms on corner and edge positions dissociate the hydrogen, which does not spill over to the face sites. Therefore, the
average number of adsorbed hydrogen atoms per surface gold atom increases with decreasing particle size. With temperature, the hydrogen uptake by
supported gold increases or remains constant, whereas it decreases for platinum. Furthermore, in H/D exchange experiments, the activity of Au/Al2O3
increases strongly with temperature. Thus, the dissociation and adsorption of hydrogen on gold is activated."
"Chemisorption of hydrogen on aluminum oxide", published by Bulletin of the Academy of Sciences of the USSR, Division of chemical science, January
1971, Volume 20, Issue 1, pp 148-149. From conclusions, to quote:
"1. A highly pure Al2O3 sample, degassed at 500°, does not chemisorb hydrogen. The absorption of microamounts of hydrogen was observed after
degassing at 800–900°.
2. The amount of absorbed hydrogen increased 10-fold when the amount of iron impurities in the Al2O3 was increased from 10−7 up to 10−3%."
---------------------------------
So, impure Al2O3 with SiO2 and Fe impurities may fill the chemisorption requirement. But, it is known that the reaction of Al and H2O is very slow
unless accelerated with a little I2, which may be unnecessary as the KOH is expected to attack the Al. My expansive take, nevertheless, on this
particular Iodine acceleration reaction with Aluminum, if employed, as to be aware of other possible side reactions:
Al + 3 I2 --> 2 AlI3
but, in the presence of water, a hydrolysis occurs:
2 AlI3 + 6 H2O --> 2 Al(OH)3 + 6 HI (see http://en.wikipedia.org/wiki/Aluminium_iodide )
removing some water. Also, with the newly created HI:
2 Al + 6 HI --> 2 AlI3 + 3 H2 (see Wiki same link)
or, for all three reactions the net reaction is:
4 Al + 6 H2O + 3 I2 ----> 2 Al(OH)3 (s) + 3 H2 (g) + 2 AlI3
and, upon adding 6 more H2O to each side:
4 Al + 12 H2O + 3 I2 ---> 4 Al(OH)3 (s) + 3 H2 (g) + 6 HI
and adding 2 more Al to each side:
6 Al + 12 H2O + 3 I2 ---> 4 Al(OH)3 (s) + 6 H2 (g) + 2 AlI3
Note, the process can be repeated, but the quantities '3 I2' and '2 AlI3' will remain constant while the amount of Al and H2O increase. As such, the
Iodine acts essentially as a catalyst (only a small amount is required to initiate the reaction regardless of the amount of water, and only that
initial Iodine is consumed). This analysis can also suggest the amount of excess Aluminum to employ to remove any water presence from the alcohol (my
calculations are 2/3 moles Al are needed to be added for each estimated moles of H2O to be removed). Also, note that when all the water is consumed,
the chain breaks and the initial number of moles of Iodine added is now 2/3 as many moles of AlI3.
-------------------------------
So a possible substitute for Mg would be to add impure Al ( Aluminum foil) sufficient to process all water in the aqueous and non-aqueous phase with a
little I2 which may be unnecessary as the KOH is expected to attack the Al. At the completion of the 1st phase, add Al2O3. Issues not addressed
include possible interaction of the small amount of Iodine and alcohol, best reaction temperature, and the expected loss in efficiency (reaction time)
of the chemisorption employing Al2O3 in place of MgO. An obvious solution: replace Al2O3 with the addition of prepared MgO from the dehydration of
inexpensive Mg(OH)2.
Overall, assuming their is some validity to my speculated reaction path, I would suspect that this could be an even more problematic synthesis than
with Magnesium, but replacing Mg with Al foil (perhaps a touch of I2), and prepared MgO (form say MgSO4), may significantly reduce material
accessibility and cost requirements.
[Edited on 20-4-2013 by AJKOER]
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blogfast25
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AJ, you'll never learn. No doubt your latest nonsense will soon be pruned onto your new whimsy thread, so why not post this stuff directly there? No
one's taking a blinding bit of notice here and they won't there either. You'd save Nicodem time and effort.
You're now officially acting in bad faith.
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AJKOER
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Blogfast:
Some background on what has occurred to date.
> I was put a whisper thread. I re-summarized and place my understanding solely on the whisper thread of what I believe is going on citing with
references to recent peer review work (not solely personal opinion or unsourced patent references).
> My whisper thread was apparently being placed on the main thread (for a time, this was unknown to me, or as to how this was occurring).
> I sent a U2U to Nicodem to bring the matter to his attention. I also requested, at his discretion, to remove my material on the main thread, and
replace a link to the whisper thread for those interested in a documented alternative hypothesis. I also stated to him that in spite my impeccable
sources, some may find my material undigestible based solely on presenting an alternate opinion as to reaction mechanism. As such, I told Nicodem that
he could use this alone as justification, with my consent, to move my material again.
So far, however, in spite of your apparent attempts to crush documented based alternative hypotheses, I am still here for now. The good news for you
as pending future experimental results, I probably have little added material to add. So barring U2Us to comment otherwise, please feel free to
present your personal opinion, sources (or lack thereof if you so wish) and any logic (or none) as I for one, promise, not to comment unless you
explicity ask me or materially mispresent my hypotheses, and then, my replies will be sourced based responses only.
[Edited on 20-4-2013 by AJKOER]
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blogfast25
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| Quote: Originally posted by AJKOER |
So far, however, in spite of your apparent attempts to crush documented based alternative hypotheses, I am still here for now.
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Next you'll invoke 'freedom of speech', idiots of your variety always do, sooner or later.
There's nothing to 'crush' here. There are no 'alternative hypotheses' being presented that are worth reading. Stick the rest of your nonsense where
it belongs: in whimsy, NOT HERE.
The alternative is to keep posting it here, where no one will read it and all you'll achieve is to further alienate people and to what good? To have
the last word?
[Edited on 20-4-2013 by blogfast25]
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Mailinmypocket
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I miss how this thread used to be up until a short time ago- with experiment results and ideas, pictures and discussions of successes and failures,
you know, all that good stuff... 
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blogfast25
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MIMP:
Well, we’ve recently seen another 2 member making potassium, so that’s quite positive. I’m sure we will see others follow suit.
Personally I’d like to see some more activity on the possible synthesis of other tertiary alcohols, as per this thread:
http://www.sciencemadness.org/talk/viewthread.php?tid=15171
But t-alcohols aren’t so easy to produce and unfortunately they are the only ones likely to work here.
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woelen
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@AJKOER: Didn't you notice how utterly annoying you are? People have asked you to stop adding more and more nonsense, but you seem unstoppable. I
suspended your account. After 2 weeks you'll be able to post again. I really do not like this kind of heavy handed moderation, but unfortunately I see
no other way to stop this annoying behavior.
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elementcollector1
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You know what would be interesting? What if I ran this reaction with calcium instead of magnesium metal? That would be a novel contribution
(although not necessarily welcome to the home chemist, given the availability of calcium metal vs. magnesium metal).
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woelen
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Experimenting is always welcome. Although calcium is less widely available than magnesium, it is interesting to see how it behaves. I do expect though
that you need small granules of calcium and the use of bulk material probably will not lead to acceptable reaction rates.
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Pyro
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How would one go about making small Ca granules from large chunks? A while ago on a warm dry day I used metal cutters to cut part of mine up into
5x5x4mm pieces, I can't realistically get smaller than that.
Would that be small enough?
Ebay has some good prices for Ca, I picked up 100g for 12eur.
all above information is intellectual property of Pyro.  |
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blogfast25
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Chips, shavings or shavings also work for Mg, so they might for Ca. But Ca is harder to obtain and tarnishes quickly in air, enormous drawbacks for
the hobbyist. Very much worth trying for those who have it though...
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Pyro
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but how will I make them?
http://www.benl.ebay.be/itm/CALCIUM-METAL-TURNING-AND-DENDRI...
i bought mine here
[Edited on 27-4-2013 by Pyro]
all above information is intellectual property of Pyro. |
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blogfast25
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That's quite a reasonable price.
Size reduction would have to be carried out under argon or under oil. It can be cut just about with a knife (acc. Wiki). Perhaps a small, dedicated
food processor or smoothie maker could be used? Load oil (kerosene) and metal, zap for some time and separate fines from coarser material
using a sieve. A calcium/kerosene smoothie, yum!
Then add catalyst and KOH and apply the procedure. Be a trailblazer! 
[Edited on 28-4-2013 by blogfast25]
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Pyro
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Nope, No way! it's bloody hard. I needed to put all my weight on the clippers to cut it. I would say it's harder than lead, a bit softer than copper
or something like that.
all above information is intellectual property of Pyro. |
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elementcollector1
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Really? I had to use a hacksaw to cut through mine, no idea that it could be cut with a straight blade.
Have I mentioned how difficult it is to hacksaw through a 1 cm round lump?
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blogfast25
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Pyro:
That hard, eh? Try grinding it with a mortar (and oil). But it's probably too soft for that...
EC1: seems your hacksaw and pyro's experience are in agreement.
But if it's sufficiently hard it should be obtainable as powder too...
It would be a real coup if someone could pull this off with Ca instead of Mg. Thermodynamically KOH + Ca == > K + CaO + 1/2 H2 is certainly
favourable, at least that's something!
[Edited on 29-4-2013 by blogfast25]
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elementcollector1
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Still, if I could cut through them at all, that'd be nice.
What would a mortar and pestle do? I'd imagine nothing, the calcium is far too hard to be affected by such a blunt instrument. Maybe a hammer on a
steel surface.
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