Sciencemadness Discussion Board

how to make Oxalic acid ?

rstar - 8-10-2012 at 04:19

da subject says the question.

but are there any simple and easy ways to make the ox acid ?

i've heard about 'the nitic acid oxidising sucrose' technique, but i dont hav conc. HNO3 or V2O5,

help...:mad:

Pyro - 8-10-2012 at 04:22

If you want to make it for use I suggest you buy it from some garden shop. they sell it to bleach wooden garden furniture.
if you are asking out of interest, how about making HNO3?

rstar - 8-10-2012 at 05:04

i wanna make it

(if i cant then i will buy :D)

pls tell some methods to make it

weiming1998 - 8-10-2012 at 05:09

Quote: Originally posted by rstar  
da subject says the question.

but are there any simple and easy ways to make the ox acid ?

i've heard about 'the nitic acid oxidising sucrose' technique, but i dont hav conc. HNO3 or V2O5,

help...:mad:


Oxidation of ethylene glycol. The final product would be oxalic acid (if CO2 is not counted). I'm not sure how you would prevent the accidental oxidation of the oxalic acid to CO2.

I found two other processes on Wikipedia, one being the carbonylation of alcohols (practically impossible at home) and the other being the hydrolysis of cyanogen (Extremely toxic!)

watson.fawkes - 8-10-2012 at 05:50

Quote: Originally posted by rstar  
are there any simple and easy ways to make the ox acid ?
As I recall, the old method is roasting cellulosic material with caustic soda (NaOH). I don't have a reference handy, but it goes back to 19th c. industry, so expect unfamiliar kinds of sources. Perhaps check a compendium of the chemical industry prior to WW I.

rstar - 8-10-2012 at 05:53

Quote: Originally posted by weiming1998  

I found two other processes on Wikipedia, one being the carbonylation of alcohols (practically impossible at home) and the other being the hydrolysis of cyanogen (Extremely toxic!)


:D thats why i wanted some simple and easy techniques
and btw how to get ethylene glycol :(?

@watson.fawkes
can ya write an equation for cellulose + NaOH ?

AJKOER - 8-10-2012 at 05:57

Before you start, Oxalic acid has commercial applications as a stain and rust remover. As such, it is commercial available and even if you do not have HNO3, someone in the business of making compounds, would probably be manufacturing it for sale.

Ways to prepare include reacting nitrogen and acetylene with an an electrical spark or discharge (this is the cyanogen route), and repeat the historical experiment of Wöhler in 1824 with the treatment of the toxic cyanogen with aqueous ammonia, which also produces urea as a white crystalline solid. This represented the first synthesis of a known natural product.

With respect to the toxic cyanogen preparation (not recommended generally and certainly without necessary safety equipment including fume hood, gas mask, etc.), per Wikipedia (http://en.wikipedia.org/wiki/Cyanogen ) to quote:

"Cyanogen is typically generated from cyanide compounds. One laboratory method entails thermal decomposition of mercuric cyanide:

2 Hg(CN)2 → (CN)2 + Hg2(CN)2

Alternatively, one can combine solutions of copper(II) salts (such as copper(II) sulfate) with cyanides, an unstable copper(II) cyanide is formed which rapidly decomposes into copper(I) cyanide and cyanogen.[7]

2 CuSO4 + 4 KCN → (CN)2 + 2 CuCN + 2 K2SO4

Industrially, it is created by the oxidation of hydrogen cyanide, usually using chlorine over an activated silicon dioxide catalyst or nitrogen dioxide over a copper salt. It is also formed when nitrogen and acetylene are reacted by an electrical spark or discharge.[8]"

There are also other industrial routes to quote from a good source (page 4 at http://www.scribd.com/doc/30134128/Oxalic-Acid ) :"Many industrial processes have been employed for the manufacture of oxalic acid since it was first synthesized. The following processes are in use worldwide: oxidation of carbohydrates, the ethylene glycol process, the propylene process, the dialkyl oxalate process, and the sodium formate process."

Also, "The sodium formate process is comprised of six steps: (1) the manufacture of sodium formate from carbon monoxide and sodium hydroxide, (2) manufacture of sodium oxalate by thermal dehydrogenation of sodium formate at 360◦C, ( 3) manufacture of calcium oxalate (slurry), (4) recovery of sodium hydroxide, (5) decomposition of calcium oxalate where gypsum is produced as a by-product, and (6) purification of crude oxalic acid. This process is no longer economical in the leading industrial countries."

After review of the above, I hope your conclusion is the best path is to just buy it, which would be the cheapest and safest path.

[Edited on 8-10-2012 by AJKOER]

rstar - 8-10-2012 at 06:40

Quote: Originally posted by AJKOER  
Before you start, Many industrial processes have been employed for the manufacture of oxalic acid since it was first synthesized. The following processes are in use worldwide: oxidation of carbohydrates, the ethylene glycol process, the propylene process, the dialkyl oxalate process, and the sodium formate process.


oxidation of carbohydrates.....
can it be done using KMnO4 ?

blogfast25 - 8-10-2012 at 08:21

Quote: Originally posted by rstar  
oxidation of carbohydrates.....
can it be done using KMnO4 ?


Even if it could be done (I don't know) you end up with a virtually inseparable mess of oxalic acid, an Mn2+ salt and excess acid. Come to think of it, Mn(II) oxalate, as most oxalates, is either very sparingly soluble or insoluble, so you'd end up with that. Extricating the pure oxalic acid from it is difficult and certainly not worth the trouble. So let the industrial wizzkids do the work and buy some. There's so much interesting stuff to be done with OA that it's better to concentrate on that, rather than frustratingly try to synthesise minute amounts of it.

watson.fawkes - 8-10-2012 at 11:22

Quote: Originally posted by rstar  
can ya write an equation for cellulose + NaOH ?
Nope. Didn't study the process in detail, which also why I don't have a handy reference for you either.

Hexavalent - 8-10-2012 at 12:15

Quote: Originally posted by blogfast25  
There's so much interesting stuff to be done with OA


Any ideas? I've done the usual stuff, e.g. pyrophoric iron, preparation of salts etc...

CHRIS25 - 8-10-2012 at 12:44

Can be prepared simply with Rhubarb. I saw it somewhere and must find it again myself because I need some oxalic acid for many different uses in my photography.

Just found a quick recipe here:
http://www.ehow.com/how_5941703_extract-oxalic-acid-rhubarb-...

[Edited on 8-10-2012 by CHRIS25]

and here is another one:

http://www.nuffieldfoundation.org/practical-chemistry/rates-...

[Edited on 8-10-2012 by CHRIS25]

AJKOER - 8-10-2012 at 15:49

Quote: Originally posted by CHRIS25  
Can be prepared simply with Rhubarb. I saw it somewhere and must find it again myself because I need some oxalic acid for many different uses in my photography.....


Per this link (http://www.independent.co.uk/life-style/science-molecule-of-... ): Rubarb contains about 1/2 of 1% of Oxalic acid. Now, as Rubarb isn't exactly cheap to acquire (unless you are a farmer) and as it is a laxative, this could be quite a synthesis.

Oxalic acid

cal - 8-10-2012 at 17:29

Quote: Originally posted by rstar  
da subject says the question.

but are there any simple and easy ways to make the ox acid ?

i've heard about 'the nitic acid oxidising sucrose' technique, but i dont hav conc. HNO3 or V2O5,

help...:mad:


In 1919, it was found that Oxalic acid could be prepared from Acetylene, nitric acid and mercuric nitrate. J. Am. Chem. Soc., 1923, 45 (3), pp 795–799

Oxalic acid production by Aspergillus niger:
an oxalate-non-producing mutant produces
citric acid at pH 5 and in the presence
of manganese
http ://mic.sgmjournals.org/content/145/9/2569.full.pdf

A method for the preparation of oxalic acid from sawdust

Citation

Alcock, Joseph R. (1923) A method for the preparation of oxalic acid from sawdust. Bachelor's thesis, California Institute of Technology. http://resolver.caltech.edu/CaltechETD:etd-02042005-103712 http://thesis.library.caltech.edu/487/

Production of oxalic acid via the nitric acid oxidation of hardwood (red oak) sawdust Jack M. Sullivan , Joseph W. Williard , David L. White , Yong K. Kim
Ind. Eng. Chem. Prod. Res. Dev., 1983, 22 (4), pp 699–709

Sugar Oxidation, Saccharic and Oxalic Acids by the Nitric Acid Oxidation of Dextrose C. L. Mehltretter , C. E. Rist
J. Agric. Food Chem., 1953, 1 (12), pp 779–783
DOI: 10.1021/jf60012a005
Publication Date: September 1953

rstar - 9-10-2012 at 04:30

any sources where i can buy OXA ?:)

elementcollector1 - 9-10-2012 at 05:11

McLendon's, Ace Hardware, Home Depot, etc. Sold as "Davy's Oxalic Acid" or simply "Wood Bleach". The one I bought was expensive, though...

MrHomeScientist - 9-10-2012 at 05:40

I found mine at a boating store, sold as crystals in a plastic bottle. It's used as wood bleach for the decks of boats.

rstar - 9-10-2012 at 05:56

any other sources?

watson.fawkes - 9-10-2012 at 08:33

Quote: Originally posted by watson.fawkes  
As I recall, the old method is roasting cellulosic material with caustic soda (NaOH).
Oxalic Acid from Sawdust - Optimum Conditions for Manufacture
Donald F. Othmer , Carl H. Gamer , Joseph J. Jacobs
Ind. Eng. Chem., 1942, 34 (3), pp 262–267
DOI: 10.1021/ie50387a003

http://pubs.acs.org/doi/abs/10.1021/ie50387a003

Yep, that Othmer. Roasting temperature is about 200 °C. Acetic acid is a co-product. Methanol and formic acid are by-products.

learningChem - 15-12-2013 at 00:00

So, that link goes to some site where fucktards want 40 something dollars to access some two pages pdf? What's the point of linking that kind of garbage?

so called 'public access' self-parody?


[Edited on 15-12-2013 by learningChem]

confused - 15-12-2013 at 02:15

its used as a stain remover for ferric chloride stains
http://www.farnell.com/datasheets/316649.pdf

violet sin - 15-12-2013 at 03:38

@ learningchem: the link goes to a paper that can be requested if you are interested, in the wanted references and needed translations (9) thread. a lill further up thread here though, is another link ( by cal ) that goes to a thesis paper.
" Alcock, Joseph R. (1923) A method for the preparation of oxalic acid from sawdust. Bachelor's thesis, California Institute of Technology. http://resolver.caltech.edu/CaltechETD:etd-02042005-103712 http://thesis.library.caltech.edu/487/ " you can view the whole thing there in pdf. totally diff paper, but if you don't feel like requesting its ready for a read thru.

blogfast25 - 15-12-2013 at 14:20

Quote: Originally posted by learningChem  
What's the point of linking that kind of garbage?

[Edited on 15-12-2013 by learningChem]


Yeah, I mean, the American Chemical Society, they really are the dregs of the world of science, aren't they? (Not)

Hint: wrong. While I would prefer all science to be open source, running a science journal cost money and as any business they need to recoup that and make a profit. Much of what is peer reviewed science is now behind pay walls (but if you search deep, chances are you'll find a free version of the article somewhere), but it was always kind of thus: subscriptions to science journals aren't free and never were.

S.C. Wack - 15-12-2013 at 14:48

Quote: Originally posted by learningChem  
What's the point of linking that kind of garbage?


It's known as giving references.
Quote: Originally posted by violet sin  
the link goes to a paper that can be requested if you are interested, in the wanted references and needed translations (9) thread.


Hard to believe, but it's already been posted, more than once. The subject somehow came up before.

[Edited on 15-12-2013 by S.C. Wack]

macckone - 17-12-2013 at 22:19

One source not mentioned is the extraction from barkeeper's friend and similar cleaners. Not exactly a chemistry reaction but a good reasonably safe extraction (don't ignite the acetone).

http://www.erowid.org/archive/rhodium/chemistry/oxalic.otc.h...

elementcollector1 - 17-12-2013 at 22:31

Quote: Originally posted by macckone  
One source not mentioned is the extraction from barkeeper's friend and similar cleaners. Not exactly a chemistry reaction but a good reasonably safe extraction (don't ignite the acetone).

http://www.erowid.org/archive/rhodium/chemistry/oxalic.otc.h...

The yields must be terrible though. From memory, isn't that stuff 5-10% oxalic acid?

macckone - 24-12-2013 at 00:13

Quote: Originally posted by elementcollector1  

The yields must be terrible though. From memory, isn't that stuff 5-10% oxalic acid?


The article I posted shows it is possible.
The actual amount in a 12 oz can is something more than 16.8g.
This is an expensive way to produce oxalic acid but it is interesting.

Keep in mind that rhubarb only contains about .5% so this is 10 times
as concentrated.