EXPERIMENT 5 PREPARATION OF OXALIC ACID

I.

Introduction

Oxalic acid with the molecular formula, H2C2O4, is known systematically as acid
ethandiova. It contains two carboxylic acids making it a comparatively strong and acidic organic
compound. Oxalic acid naturally occurs in fleshy fruits of buckwheat, black pepper, parsley,
poppy seed, spinach, most nuts and beans.
It exists as a solid, water-soluble white crystalline substance. It is poisonous and highly
corrosive and hence, should be handled carefully. Because of its acidity, it is widely used as an
acid rinse where it could form a soluble complex with insoluble iron compounds.

Figure 1 Oxalic Acid structure

Oxalic acid can be synthesized by the oxidation of carbohydrates such as glucose,
sucrose, starch, dextrin, cellulose with nitric acid. This oxidation process split carbon atoms off
in pairs to give oxalic acid.
C12H22O11 + 9O2 ----> 6(COOH)2 + 5H2O
Figure 2 Oxidation of sucrose to yield oxalic acid

II.

DATA AND RESULTS

Table 1 Data Gathered from the Preparation of Oxalic Acid

Amount/Mass
Sucrose
5.01g
HNO3
26mL
Filter paper [a]
0.5908g
Filter paper + oxalic acid [b]
0.6774g
Oxalic acid product/ experimental yield [b-a]
0.0866g
Calculation of Theoretical Yield
Balanced Reaction:
C12H22O11 + 9O2 ----> 6(COOH)2 + 5H2O
Based on the balanced reaction, 1 mol of sucrose will produce 6 mol of oxalic acid.

T heoretical Yield=5.01 g Sucrose

1 mol Sucrose
6 mol Oxalic acid 90.03548 g Oxalic acid

=7.91 g S
342.30008 g Sucrose
1 mol Sucrose
1mol Oxalic acid

Yield
0.0866 g Oxalic acid
100 =(
100 =1.09
( Experimental
)
Theoretical Yield
7.91 g Oxalic acid )

Percentage Yield=

III.

DISCUSSION

Oxalic acid was prepared by oxidizing sucrose with nitric acid. Sucrose (figure 3) is a
naturally occurring carbohydrate most commonly known as table sugar. It is a nonreducing
disaccharide with a molecular formula of C12H22O11. When hydrolysed, it breaks down into
monosaccharide glucose and fructose.

Figure 3 Sucroses chemical structure. The glucose and fructose are linked by an acetal
oxygen bridge in the alpha orientation.
Nitric acid is a strong acid and a powerful oxidizing agent. It oxidizes organic
compounds such as carbohydrates to their highest oxidation states with the formation of
nitrogen dioxide for concentrated acid and nitric oxide for dilute acid. Nitric acid oxidizes an
aldose into a dicarboxylic acid, aldaric acid. The aldehyde carbonyl and the terminal
CH2OH are oxidized in this reaction.

Figure 4 Oxidation of glucose which is an example of an aldose into glucaric acid, an aldaric
acid.

Sucrose was made to oxidize with nitric acid. Around 5 grams of sucrose and 26 ml of
concentrated nitric acid were allowed to react in a beaker and were heated until red fumes
appeared. These red fumes are NO2 and NO gases which are highly toxic. Proper ventilation
is needed. The mixture was then set to evaporate to approximately 10 ml when the fumes
disappeared. However in the experiment, the red fumes in the mixture took too long to
disappear that led to an excessive evaporation of the mixture. The mixture was then taken out
of the hot plate and was added 10 ml even if there are still red fumes generating. It was again
evaporated to 10 ml to finish off the reaction.
C6H12O6 + 12HNO3 3C2H2O42H2O + 3H2O + 3NO + 9NO2
Oxalic acid dihydrate

Brown/Red Gas

Figure 5 Oxidation reaction of glucose and nitric acid forming oxalic acid dehydrate and NO2
gas.
The mixture was then crystalized to collect pure oxalic acid. In the experiment, however,
instead of getting pure white crystal like solid, the oxalic acid was yellowish in color. This would
indicate that the oxalic acid must have had some nitric acid that did not completely react as the
consequence of the red fumes still generating when the 10 ml water was added and was again
evaporated. Personal errors might also take account in the experiment such not proper handling
of the chemicals. Vacuum filtration was used to separate the oxalic acid crystals from its liquid
impurities. The impurities remained in the liquid solution and were passed though the Buchner
funnel. The obtained oxalic acid was weighed and the percentage yield was calculated. The data
is summarized on table 1 (see Data and Results). Only 1.09% percentage yield was attained in
the experiment. This low percentage yield might be caused of the excessive evaporation that
occurred in the first few steps in the experiment. Excessive washings during vacuum filtration is
also a factor in this low percentage yield.
Conclusion
Oxalic acid is the simplest dicarboxylic acid is prepared by oxidizing sucrose with nitric acid.
Sucrose is a nonreducing disaccharide compromising monosaccharaides glucose and fructose.
Nitric acid is a strong oxidizing agent which converts aldose (glucose) into a dicarboxylic acid.
Sucrose undergoes the same oxidation process with nitric acid forming an oxalic acid, a
dicarboxylic acid. Vacuum filtration was used to isolate the pure oxalic acid separating it from its
liquid impurities. Only 1.09% oxalic acid percentage yield was obtained in the experiment.

References

McMurry, J. (2012). Biomolecules: Carbohydrates. Organic Chemistry, 8th Edition. Canada:

Cengage Learning.
Smith, J. (2011). Carbohydrates. Organic Chemistry, 3rd Edition. New York: McGraw-Hill
Companies.