Oxalicacidmanufacturing 201231154014

Commercial Production of Oxalic Acid
By
Mr. Muhammad Ullah Afridi
Institute of Chemical Sciences, University of Peshawar.
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MANUFACTURING OF
OXALIC ACID
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Introduction
• Oxalic acid, H2C204 is a colorless crystalline dicarboxylic acid.
It produces a colorless solution on dissolving in water.
• If we consider the acid strength, it is a much stronger acid than
acetic acid. Oxalic acid is a reducing agent and its conjugate
base is called as oxalate.
• Oxalate acts as a chelating agent for metal cations. Typically,
oxalic acid also exists in the form of dihydrate.
• Ingestion of oxalic acid through skin contact or orally proves to
be fatal.
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• Scheele in 1776 discovered the oxalic acid.
• Scheele produced oxalic acid by the oxidation
of sugar using nitric acid and it was called
saccharic acid.
• It is odorless with molecular formula
126.07gram per mole.
• It is orthorhombic colorless crystal
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Manufacturing of Oxalicacid
There are three methods for manufacturing of
oxalic acid:
 Oxalic acid from sodium formate
 Oxalic acid from propylene
 Oxalic acid dimethyl oxalate process
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1. Oxalic acid from sodium formate

Raw material
 Solid sodium hydroxide (97-98%)
 carbon monoxide
Working
 Solid sodium hydroxide (97-98%) and carbon monoxide react
at a 2000 0C temperature and 150psi pressure in an autoclave
to produce sodium formate.
 On completion of this reaction, the pressure in the autoclave
is gradually reduced and the temperature is increased to
4000C. The ceasing of the evolution of hydrogen results in
the completion of the reaction.
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 The reaction mixture was collected in a precipitator and
calcium hydroxide was added to it with stirring.
 This was followed by the filtration of the calcium oxalate
and then sodium hydroxide was concentrated that could be
reused.
 The filter cake of crude calcium oxalate is taken to an acidifier
with a small amount of calcium carbonate and then treated
with dilute sulfuric acid.
 The precipitation of calcium results in the formation of
calcium sulphate dihydrate (CaSO4.2H2O).
 The mother liquor was then taken to a crystallizer and
concentrated to the specific gravity of 300 Be.
 Finally, Crystals of oxalic acid in the form of
dehydrating was obtained which was then washed and
dried.
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 The yield of oxalic acid dehydrate was nearly 80% by
weight depending on sodium formate.
 It is generally sold and used in the form of dihydrate.
 But anhydrous oxalic acid can also be obtained by
heating the dihydrate to 1000C by the loss of two
molecules of water.
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 The direct acidification of sodium oxalate with methanol in
the ratio of 1:3 and in the presence of 0.8 parts of
concentrated sulfuric acid also produces oxalic acid.
 Then the insoluble sodium sulfate can be separated, from the
methyloxallatemethanol sulfuric acid solution. The sodium
sulfate is then filtered and the mother alcohol is hydrolyzed
by the addition of 3.5 parts water. This yields oxalic acid and
methanol. The methanol obtained is then distilled and
recycled.
 The crude oxalic acid solution is then concentrated and
crystallized producing the oxalic acid. Molasses can be
oxidized with nitric acid to also produce oxalic acid.
Similarly, oxidation of organic compounds like glycol,
alcohol, fats, and other cellulosic materials in the presence of
nitric acid also produces oxalic acid.
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2. Oxalic acid from propylene

• This method involves the oxidation of propylene with nitric acid
to produce oxalic acid.
• It involves a two-step process, wherein the first step propylene
gets converted into a-nitratolactic acid and the second step
allows the oxidation of a-nitratolactic acid to oxalic acid.
• In the first reactor, propylene was introduced where it reacts
with nitric acid. The molar ratio of propylene and nitric acid is
kept at 0.01 -0.5. The mixture from the first reactor was taken
into the second reactor where it reacts with oxygen
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 In this step, the vapor of nitric acid continuously evolves
from the top of the vessel.
 The stream from the vessel has intermediate and a trace
amount of nitric acid.
 It was then taken into the reservoir tank where acid was
evolved. a-nitratolactic acid from the reservoir was then
collected into an autoclave where it oxidization occurs at 45 -
1000C in the presence of mixed acid as catalyst.
 In this step, a- nitratolactic acid gets converted into oxalic
acid dihydrate. The crude product was then taken into a
crystallizer where oxalic acid crystals are obtained.
 The slurry obtained from crystallizer is filtered and sent for
drying operation to generate dried oxalic acid.
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3. Oxalic acid dimethyl oxalate process

• In this process, methyl nitrite is regenerated from circulating gas
containing CO and from regeneration column it was pressurized
and then fed to the reactor.
• In this vessel, dimethyl oxalate was produced but the
consumption of methyl nitrite takes place.
• Freshly brewed dimethyl oxalate and unconverted mixture were
then taken into the condenser where methanol was added.
• Uncondensed vapour containing methyl nitrite, water and
methanol were drawn to regeneration column accompanied by
the addition of NOx and oxygen to regenerate the methyl nitrite
which is to be recycled.
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 Condensed dimethyl oxalate from the condenser,
when taken into the distillation column, removes
water vapours while dimethyl oxalate was
hydrolysed.
 After the completion of hydrolysis of oxalate, the
slurry was sent to the crystallizer to generate a
crystal of oxalic acid.
 The slurry is then filtered and passed from the dryer
to store dried oxalic acid.
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 In propylene process, the usage of sulfuric acid

results into corrosion problem at the oxidation step.
The oxidation reaction can be enhanced by a large
reactor. There is a possibility of unstable by-product
formation along with a-nitratolactic acid and it may
even lead to explosion or decomposition.
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Applications
 Oxalic acid can be used as a mordant(substance
used to treat leather before dyeing aids) in dying
processes
 Oxalic acid can remove rust and thus can be used
for cleaning or bleaching
 Bee keepers use 3.2% solution of oxalic acid or its
vaporized form
 Helps in the removal of mustard, ink, different
food stains as well as other types of stains.
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Commercial Production of Oxalic Acid

1. Oxalic acid from sodium formate

2. Oxalic acid from propylene

3. Oxalic acid dimethyl oxalate process

 In propylene process, the usage of sulfuric acid

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