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CHRIS25
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Possible to make Tartaric acid from Cream of Tartar?
Tartaric acid has a formula of C4H6O6; Sodium Bitartrate (cream of Tartar) has KC4H5O6. Now the stupid thought I had - If I can take away the
Potassium and kick out a single hydrogen atom then I have Tartaric acid? Laugh later but that was my immediate logic. Otherwise is there any 'Home'
method I could use to get tartaric acid?
Looking at the chemistry supplier I have a choice of two products the L+tartaric which is hugely expensive 1Kg for 82 Euros; but then there is the
other one which is called by another name of Dihydroxybutane Dioic Acid at 23 euros for 500 grams. I read that the former is the acid in its natural
state, but I am not sure what they mean by this, natural state?
‘Calcination… is such a Separation of Bodies by Fire, as makes ‘em easily reducible into Powder; and for that reason ‘tis call’d by some
Chymical Pulverization.’ (John Friend, Chymical Lectures London, 1712)
Right is right, even if everyone is against it, and wrong is wrong, even if everyone is for it. (William Penn 1644-1718)
The very nature of Random, Chance development precludes the existence of Order - strange that our organic and inorganic world is so well defined by
precision and law. (me)
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arsphenamine
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It's slightly more complicated than expected.
The prep is a two pot reaction that relies on the lower solubilities of calcium salts.
Generate the calcium tartrate from cream of tartar and later acidify with sulfuric acid.
http://www.youtube.com/watch?v=Bt36jpk02Pk
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CHRIS25
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Hi thanks for the video, watched, will try. Just hope my calcium carbonate is pure.
‘Calcination… is such a Separation of Bodies by Fire, as makes ‘em easily reducible into Powder; and for that reason ‘tis call’d by some
Chymical Pulverization.’ (John Friend, Chymical Lectures London, 1712)
Right is right, even if everyone is against it, and wrong is wrong, even if everyone is for it. (William Penn 1644-1718)
The very nature of Random, Chance development precludes the existence of Order - strange that our organic and inorganic world is so well defined by
precision and law. (me)
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unionised
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There's another route. Add a slight excess HCl which produces tartaric acid + salt then dry the solution down and dissolve the tartaric acid into
alcohol (which doesn't dissolve salt, but will dissolve the acid.)
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Hexavalent
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Any specific alcohol, unionised? I assume you mean EtOH.
"Success is going from failure to failure without loss of enthusiasm." Winston Churchill
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unionised
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I meant ethanol, but I think IPA would also work.
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CHRIS25
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Quote: Originally posted by unionised  | | There's another route. Add a slight excess HCl which produces tartaric acid + salt then dry the solution down and dissolve the tartaric acid into
alcohol (which doesn't dissolve salt, but will dissolve the acid.) |
Can you elaborate please. When you said add excess HCL, at what point what you referring to? Add HCL directly to the Cream of Tartar? And actually
I don't think I can get hold of ethanol, the best I have is surgical spirit which is 90% ethanol and 5% methanol and the other 5% I have no idea.
And what is IPA? Indian pale ale?
Just browsing through my catalogue and was very surprised to read that while they sell Pure 100% ethanol very expensive, very expensive, However they
also sell what is called: Industrial methylated spirit at 99%, or 0.8g per mL weight. Now I have methylated spirit but it is no way this pure. So
would the above work, or would it have to be the full grade purified ethanol?
[Edited on 28-10-2012 by CHRIS25]
[Edited on 28-10-2012 by CHRIS25]
‘Calcination… is such a Separation of Bodies by Fire, as makes ‘em easily reducible into Powder; and for that reason ‘tis call’d by some
Chymical Pulverization.’ (John Friend, Chymical Lectures London, 1712)
Right is right, even if everyone is against it, and wrong is wrong, even if everyone is for it. (William Penn 1644-1718)
The very nature of Random, Chance development precludes the existence of Order - strange that our organic and inorganic world is so well defined by
precision and law. (me)
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Hexavalent
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The surgical spirit should work just fine.
IPA is isopropyl alcohol.
"Success is going from failure to failure without loss of enthusiasm." Winston Churchill
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CHRIS25
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Is this correct then: HCL+C4H5NaO6=C4H6O6+NaCL as simple as this? and if so, is the more labour intensive method as first proposed a bit redundant?
and how do I then get the acid out of the alchohol?
[Edited on 28-10-2012 by CHRIS25]
[Edited on 28-10-2012 by CHRIS25]
‘Calcination… is such a Separation of Bodies by Fire, as makes ‘em easily reducible into Powder; and for that reason ‘tis call’d by some
Chymical Pulverization.’ (John Friend, Chymical Lectures London, 1712)
Right is right, even if everyone is against it, and wrong is wrong, even if everyone is for it. (William Penn 1644-1718)
The very nature of Random, Chance development precludes the existence of Order - strange that our organic and inorganic world is so well defined by
precision and law. (me)
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Random
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| Quote: Originally posted by CHRIS25 |
Is this correct then: HCL+C4H5NaO6=C4H6O6+NaCL as simple as this? and if so, is the more labour intensive method as first proposed a bit redundant?
and how do I then get the acid out of the alchohol?
[Edited on 28-10-2012 by CHRIS25]
[Edited on 28-10-2012 by CHRIS25] |
yeah add hcl, evaporate until dry, add alcohol, filter, evaporate
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unionised
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The last time I checked, surgical spirit had things like castor oil, methyl salicylate, and diethyl phthalate in it and those won't evaporate off the
tartaric acid easily.
It might work.
The way to check would be to let some of the spirit evaporate from a clean dish and see if there's any residue. If there is then you would do better
to use something else.
The reason they don't do this commercially is that HCl is generally more expensive than H2SO4 and also alcohol is rather expensive.
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CHRIS25
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| Quote: Originally posted by unionised | The last time I checked, surgical spirit had things like castor oil, methyl salicylate, and diethyl phthalate in it and those won't evaporate off the
tartaric acid easily.
It might work.
The way to check would be to let some of the spirit evaporate from a clean dish and see if there's any residue. If there is then you would do better
to use something else.
The reason they don't do this commercially is that HCl is generally more expensive than H2SO4 and also alcohol is rather expensive.
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I thought I answered this one, anyway I am doing what you suggest. Will see.
‘Calcination… is such a Separation of Bodies by Fire, as makes ‘em easily reducible into Powder; and for that reason ‘tis call’d by some
Chymical Pulverization.’ (John Friend, Chymical Lectures London, 1712)
Right is right, even if everyone is against it, and wrong is wrong, even if everyone is for it. (William Penn 1644-1718)
The very nature of Random, Chance development precludes the existence of Order - strange that our organic and inorganic world is so well defined by
precision and law. (me)
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DJF90
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All these suggestions seem horribly convoluted. Dissolve the potassium bitartrate in e.g. 2M HCl, and extract the acidic solution with an organic
solvent (I intend to use DCM). Evaporate the DCM to get the tartaric acid. I suspect the commercial salt is of the "natural" (although the other
enantiomer also occurs naturally just more rarely) L-(+)-tartaric acid. Identification of enantiopure vs racemic acid can be done via melting point,
but determination of which enantiomer is present is done by polarimetry or microscopy of well-formed crystals. The racemic acid can be produced by
extended reflux in sodium hydroxide solution (I think the procedure is given in a textbook by Cohen, 1910, possibly in the forum library).
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unionised
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| Quote: Originally posted by DJF90 | | All these suggestions seem horribly convoluted. Dissolve the potassium bitartrate in e.g. 2M HCl, and extract the acidic solution with an organic
solvent (I intend to use DCM). Evaporate the DCM to get the tartaric acid. I suspect the commercial salt is of the "natural" (although the other
enantiomer also occurs naturally just more rarely) L-(+)-tartaric acid. Identification of enantiopure vs racemic acid can be done via melting point,
but determination of which enantiomer is present is done by polarimetry or microscopy of well-formed crystals. The racemic acid can be produced by
extended reflux in sodium hydroxide solution (I think the procedure is given in a textbook by Cohen, 1910, possibly in the forum library).
|
LOL
Tartaric acid isn't soluble in chloroform, so I rather doubt it's soluble in DCM.
http://www.sciencelab.com/msds.php?msdsId=9925165
Your procedure simply won't work.
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CHRIS25
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Also mr.Oxford, you might as well have been speaking chinese in code! But thanks for the excerpt from ye olde book.
And Unionised, nothing out of the ordinary with the surgical spirit, it seems to have evaporated without leaving a trace of anything...I presume then
that I simply place my solution of tartaric acid and sodium chloride mixtute into the methanol and let filter, whereby the sodium chloride would be
left behind in the filter bag? Or is this all too simple.....
‘Calcination… is such a Separation of Bodies by Fire, as makes ‘em easily reducible into Powder; and for that reason ‘tis call’d by some
Chymical Pulverization.’ (John Friend, Chymical Lectures London, 1712)
Right is right, even if everyone is against it, and wrong is wrong, even if everyone is for it. (William Penn 1644-1718)
The very nature of Random, Chance development precludes the existence of Order - strange that our organic and inorganic world is so well defined by
precision and law. (me)
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Vargouille
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It's probably that simple. What I would do, mind you, is give the tartaric acid a recrystallization or two afterwards to get rid of any other
contaminants.
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CHRIS25
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| Quote: Originally posted by Vargouille | | It's probably that simple. What I would do, mind you, is give the tartaric acid a recrystallization or two afterwards to get rid of any other
contaminants. |
Hi, whoops, you've got me there. How on earth do I re-crystallize? Do you mean dissolve it in water again and then de-hydrate?
Except of course it won't filter - it's too viscous. So scrub round the above. Just forgot to look at it, it can not be filtered. And I made silly
mistake, it's potassium bitartrate not sodium, as I erroneously kept referring to it, so KC4H5O6...
[Edited on 29-10-2012 by CHRIS25]
[Edited on 29-10-2012 by CHRIS25]
‘Calcination… is such a Separation of Bodies by Fire, as makes ‘em easily reducible into Powder; and for that reason ‘tis call’d by some
Chymical Pulverization.’ (John Friend, Chymical Lectures London, 1712)
Right is right, even if everyone is against it, and wrong is wrong, even if everyone is for it. (William Penn 1644-1718)
The very nature of Random, Chance development precludes the existence of Order - strange that our organic and inorganic world is so well defined by
precision and law. (me)
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Vargouille
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Typically it's done by dissolving it in a minimum of hot water to dissolve most of it, filtering, or in your case, decanting, and allowing to cool
slowly.
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CHRIS25
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Ok. Well I just read that Potassium chloride is only partially soluble in Ethanol. So I should still get a reasonable tartaric produce. Otherwise I
will have to opt for the long winded process from the YouTube demonstration. I have a little tartaric acid from a chemistry set, so I have the real
thing for comparison.
‘Calcination… is such a Separation of Bodies by Fire, as makes ‘em easily reducible into Powder; and for that reason ‘tis call’d by some
Chymical Pulverization.’ (John Friend, Chymical Lectures London, 1712)
Right is right, even if everyone is against it, and wrong is wrong, even if everyone is for it. (William Penn 1644-1718)
The very nature of Random, Chance development precludes the existence of Order - strange that our organic and inorganic world is so well defined by
precision and law. (me)
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DJF90
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@unionised: I was working off the top of my head without reference to any data. However thats not to say what I suggested won't work, it just needs a
little tweaking. Performing the extraction with DCM might not work very well due to solubility reasons, but what about other organic solvents; ethyl
acetate springs to mind, as does the use of chlorofom-ipa (7:3 might be appropriate in this case) - a well known solvent mixture for extraction of
highly water soluble organics. Sorry to piss on your fire, asshole.
[Edited on 30-10-2012 by DJF90]
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unionised
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| Quote: Originally posted by DJF90 | @unionised: I was working off the top of my head without reference to any data. However thats not to say what I suggested won't work, it just needs a
little tweaking. Performing the extraction with DCM might not work very well due to solubility reasons, but what about other organic solvents; ethyl
acetate springs to mind, as does the use of chlorofom-ipa (7:3 might be appropriate in this case) - a well known solvent mixture for extraction of
highly water soluble organics. Sorry to piss on your fire, asshole.
[Edited on 30-10-2012 by DJF90] |
LOL again.
Bad language doesn't stop you being wrong.
Since tartaric acid is very soluble in water it's unlikely that you will find an immiscible solvent with a usable partition coefficient.
For example, what springs to your mind isn't good enough: you need evidence so, for example, here is a page which gives the solubility of tartaric
acid in ethyl acetate
http://www.biochemicaldiagnostics.com/pdffiles/um17psilocin....
The solubility is 1 mg/ml.
On the other hand, the solubility in water is about 1500 mg/ml.
From that we can estimate the partition coefficient as being about 1/1500.
If you had 100 ml of a solution of tartaric acid and you wished to extract half the acid with ethyl acetate, you would need 150 litres of solvent.
It's an oversimplification- not least because all the water would dissolve with that much solvent- but it does show that your idea is still utter
nonsense.
Next time you see fit to work off the top of your head, find a better one.In particular, if you are about to post something on line, check with Google
that you are not making a fool of yourself.
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CHRIS25
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Well that was a pointless exercise in nothingness. Having filtered the potasssium chloride (white) The solution in the beaker was a yellowish colour
of methanol (surgical spirit), and I began to heat it it on a hotplate for 5 minutes. the smell was pleasant but pungent - knocked me backwards. I
decided to read about heating this stuff and read that it was highly flammable and dangerous fumes. So removed it from the heat. I had hoped that
there was tartaric acid hidden in this somewhere - but do not know what to do now.
The Whole yellow solution has now evaporated into emptiness, a magical example of nothingness, not even one grain.......So what is this with the
alchohol treatment and collecting the tartaric acid through evaporation.Anyone?
[Edited on 31-10-2012 by CHRIS25]
‘Calcination… is such a Separation of Bodies by Fire, as makes ‘em easily reducible into Powder; and for that reason ‘tis call’d by some
Chymical Pulverization.’ (John Friend, Chymical Lectures London, 1712)
Right is right, even if everyone is against it, and wrong is wrong, even if everyone is for it. (William Penn 1644-1718)
The very nature of Random, Chance development precludes the existence of Order - strange that our organic and inorganic world is so well defined by
precision and law. (me)
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Hexavalent
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Not being funny, but something I do sometimes is discard my product and keep the waste. Are you certain you've not done that this time?
"Success is going from failure to failure without loss of enthusiasm." Winston Churchill
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CHRIS25
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| Quote: Originally posted by Hexavalent | | Not being funny, but something I do sometimes is discard my product and keep the waste. Are you certain you've not done that this time?
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Hi there, no, I have actually thrown nothing away at all. I have the filtered white mass still in a filter, and the beaker full of NO(th)Ingn.3ss
still sitting there with the Alchohol residue at the bottom where the dry tartaric acid should be.
‘Calcination… is such a Separation of Bodies by Fire, as makes ‘em easily reducible into Powder; and for that reason ‘tis call’d by some
Chymical Pulverization.’ (John Friend, Chymical Lectures London, 1712)
Right is right, even if everyone is against it, and wrong is wrong, even if everyone is for it. (William Penn 1644-1718)
The very nature of Random, Chance development precludes the existence of Order - strange that our organic and inorganic world is so well defined by
precision and law. (me)
|
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Hexavalent
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What have you filtered?
"Success is going from failure to failure without loss of enthusiasm." Winston Churchill
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