OXALIC

ACID
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 Key Concepts

• Introduction of oxalic acid

• Formula of oxalic acid
• Preparations of oxalic acid
• Chemical reactions of oxalic acid
• Uses of oxalic acid
• Impact of oxalic acid on health
• Summary

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Formula of oxalic acid

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 Introduction of oxalic acid
• Oxalic acid is an organic compound with the
formula of C2H2O4.
• It is a white crystalline solid that forms a colorless
solution in water and is also known as a
dicarboxylic acid.
• Oxalic acid is a reducing agent.
•  It is a chelating agent (A chemical compound that binds
tightly to metal ions. In medicine, chelating agents are used
to remove toxic metals from the body)for metal cations. 
• Its acid strength is much greater than that of acetic
acid.
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 Introduction of oxalic acid

• Oxalic acid occurs as the dihydrate with the formula

C2H2O4·2H2O. It occurs naturally in many foods, but
excessive ingestion of oxalic acid or prolonged skin
contact can be dangerous.
• Scheele in 1776 discovered the oxalic acid.
• Its name is derived from Greek word ‘OXEYES’
meaning sharp acidic. It is transparent, odourless and
colourless crystal. Its boiling point is 149 to 160 degree
Celsius whereas melting point is 101.5 degree Celsius.
Commercially it is available as dehydrate which is in
crystalline form with two water molecules attached to
each molecule of oxalic acid (HOOCCOOH.2H2O).
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 Preparation of oxalic acid
From sodium formate
Oxalic acid is usually prepared by heating sodium formate with sodium hydroxide
to form sodium oxalate, which is converted to calcium oxalate and treated with
sulfuric acid to obtain free oxalic acid.

•2HCOONa + NaOH 375 °C

(COO)2Na2 + H2

•(COO)2Na2 + Ca (OH)2 (COO)2Ca + 2NaOH

•(COO)2Ca + H2SO4 (COOH)2 + CaSO4

•From propylene
Oxalic acid is produced by absorbing propylene in strong nitric acid and then
heating the solution while removing the oxides of nitrogen formed, preferably after
introducing oxygen into the solution.
CH3-CH=CH2 + HNO3 CH 3-CH-COOH + H2O
•
• ONO2

• CH3-CH-COOH + 5/2 O2 H 2C2O4 + HNO3 + NO2 + H2O

•
• ONO2 6
 Preparation of oxalic acid
• From oxidation of glucose
• In lab, oxalic acid can be prepared by
oxidizing sugar using nitric acid in presence of
vanadium pentoxide as catalyst.

• C6H12O6 + 6 HNO3 H2SO4 60 °C

3C2H2O4. 2H2O + 6 NO
V 2O 5

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 Chemical reactions of oxalic acid
• Reaction of oxalic acid with oxygen
• C2H2O4 + O2 2 CO2 + 2 H2O
• Acid base reaction
• Oxalic acid is weak organic dicarboxylic acid and NaOH is a strong mono
acidic base. The reaction between them is acid base neutralization reaction. 
• C2H2O4 + 2NaOH Na2C2O4 + H2O

• Reaction of oxalic acid with KMnO4

• Potassium permanganate (KMnO4) reacts with oxalic acid (H2C2O4) in aqueous
sulphuric acid according to following equation.

• 5C2H2O4 + 2KMnO4 + 3H2SO4 K2SO4 + 2MnSO4 + 10CO2 +8H2O

• KMnO4 oxidizes (COOH)2 to give CO2 and H2O.

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 Chemical reactions of oxalic acid
• Reaction of oxalic acid with methyl alcohol
• Dimethyl oxalate can be obtained by esterification of oxalic acid with methanol
using sulphuric acid as a catalyst:

• C2H2O4 + CH3OH H SO
2 4 (CH3 )2C2O4 + 2H2O
• (dimethyl oxalate)

• Decomposition of oxalic acid

• The decomposition of oxalic acid proceeds at temperatures above 80°C; the
activation energy of the reaction is 18.6 kcal/mol.
• C2H2O4 H2SO4 CO + CO2 +H2O

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 Uses of oxalic acid
• Oxalic acid can be used as a mordant in dying process.
• Oxalic acid can remove rust and thus can be used for
cleaning or bleaching.
• Beekeepers use oxalic acid solution.
• Oxalic acid helps in the removal of mustard, ink and
different food stains.
• It is the reducing agent used for the developing
photographic film
• Calcium can be removed from waste water using oxalic
acid.
• Oxalic acid can be reused. It is present in leaves, roots of
various plants in many forms. 10
 Impact of oxalic acid on health
• Oxalic acid corrode tissue.
• Inhaled is harmful and it may result in severe
irritation.
• Ingestion of it result in renal damage.
• In contact with skin, severe itching and burning
sensation prevail.
• Eye contact may result in corrosive effect.
• Chronic exposure may lead to inflammation.
• Oxalic acid removes calcium in the blood forming
calcium oxalate and severe damage to kidney.
• Has a harmful effect on environment due to pH shift.
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 Summary

• Oxalic acid is a comparatively strong organic

dicarboxylic acid..
• It is endogenously produced in humans.
• Oxalic acid is used in woodwork.
• Oxalic acid used in textile industry.
• Oxalic acid used as disinfectant.
• Oxalic acid is occurring naturally in honey.

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