Xiao 101083582 Report1

CHEM 2203
Experiment 1- Solubility & Recrystallization

Zhiqiao Xiao
101083582
Results and calculations
Table1. The solubility in hot and cold conditions of five different compounds (Anthracene,
Benzoic acid, Phthalic acid, resorcinol and sodium naphthionate) in four different solvents
(ligroin, toluene, ethanol and water), with observation of recrystallization.
Ligroin Toluene Ethanol Water
Anthracene Cold: insoluble Cold: insoluble Cold: insoluble Cold: insoluble
Hot: not dissolve Hot: not Hot: sightly Hot: not
dissolve dissolve dissolve
Needles formed
Benzoic acid Cold: insoluble Cold: insoluble Cold: insoluble Cold: insoluble
Hot: dissolve Hot: dissolve Hot: dissolve Hot: not
dissolve
Needle like crystals Needle like

formed crystals formed
Phthalic acid Cold: insoluble Cold: insoluble Cold: insoluble Cold: insoluble
Hot: moderately Hot: not Hot: not Hot: not
dissolve dissolve dissolve dissolve
Resorcinol Cold: insoluble Cold: insoluble Cold: insoluble Cold: insoluble

Hot: not dissolve Hot: not Hot: dissolve Hot: dissolve
dissolve completely
Needles formed
Sodium Cold: insoluble Cold: insoluble Cold: insoluble Cold: insoluble
naphthionate hot: not dissolve Hot: not Hot: sightly Hot: dissolve
dissolve dissolve
For anthracene, it was insoluble under cold conditions of all solvents, yet it sightly
dissolved in hot ethanol and needles formed after cooling. For Benzoic acid, it was
insoluble in cold condition of four of the solvents, it dissolved in hot condition of
ligroin, toluene, and ethanol. Needle like crystals formed in ligroin and water after
cooling down. Resorcinol was insoluble in all the cold solvents, it dissolved in hot
ethanol and hot water and needles formed in Toluene after chilling. Sodium
naphthionate was insoluble in all the solvents in cold condition, but sightly
dissolve in hot ethanol and hot water and no recrystallization were observed.
Percent recovery of salicylic acid
The initial weight of the material was recorded to be 1.00g, the weight of the
recovered salicylic acid was 0.833g.
mass of recovered material

percent recovery = mass of initial material
× 100
0.833 g
percent recovery = 1.00 g × 100 = 83.3%
Discussion
The objective of this experiment is to test the solubility of five compounds
including anthracene, benzoic acid, phthalic acid, resorcinol, and sodium
naphthionate using four solvents (ligroin, toluene, ethanol, and water). Also,
purification and recrystallization of salicylic acid would be applied to determine its
percent recovery.
Like-dissolve-like theory explain the ability for solutes to dissolve in solvent

depends on their polarity (Ying et al., 2019). For instance, polar solutes tend to
dissolve in polar solvents and non-polar solutes tend to dissolve in non-polar
solvents (Montes et al., 2003). In this experiment, benzoic acid and toluene both
consist of benzene ring, thus they are likely to be dissolved when mixing.
Resorcinol and ethanol both have alcohol (OH)group, thus they are likely to be
dissolved when mix together as well.
Phthalic acid can only be partially dissolved in hot condition of ligroin, there are
functional group of carboxyl in phthalic acid, it should be dissolved in ethanol and
water because they share similar polarity.
Recrystallizations occur when an impure solid compound mixed with a heated

solvent, after the solution being cool down, solubility of the compound decreases
and thus form pure crystals (White and Buchanan, 2022). When it comes to a good
solvent for recrystallization, it follows the characteristic that solids have low
solubility in cold condition and high solubility in hot condition (Lavino etal.,
2021). Water is being used as the solvent for recrystallizations of salicylic acid
since it it’s a good solvent when being heated.
The percent recovery of salicylic acid was yielded to be 83.3%. The recovery of
salicylic acid was through reduction of Alizarin Yellow by charcoal. Technique
being applied through Erlenmeyer flask and suction filtration. One possible error
causes a lower yield is that excess amount of distilled water being added. Another
cause of a lower yield would be the silicify acid compound remain at the filter
paper.
Techniques to determine if the salicylic acid is pure can be through visual

inspection. If there is present of precipitate, then there are impurity remain. If the
solution is appeared to be clear and uniform, then the compound is pure. The
second technique is to check the substances by chromatography and compared the
fingerprint to that of the literature values (Tivert and Vessman, 2005).
Conclusion
The purpose of this experiment is to test the solubility of anthracene, benzoic acid,
phthalic acid, resorcinol, and sodium naphthionate in solvents of ligroin, toluene,
ethanol, and water. Further familiarize the theory of “like dissolves like”. Also,
purification and recrystallization of salicylic acid. Anthracene sightly dissolve in
hot ethanol with needles formed. Benzoic acid dissolve in hot ligroin, toluene as
well as ethanol, needles like crystals formed Phthalic acid moderately dissolve in
hot ligroin. Resorcinol dissolve in hot ethanol forming needle crystals, also
dissolve and water. Sodium naphthionate sightly dissolve in hot ethanol and
dissolve in water, no observation of needles.
The percent recovery of salicylic acid was yielded to be 83.3%. According to the
results, the objective of the experiment was achieved and the further analysis of the
purity of the salicylic acid can be through infrared spectrometry.
References
Lavino, A.; Ferrari, M.; Barresi, A.; Marchisio, D. Effect of different good solvents in flash nano-
precipitation via multi-scale population balance modeling-CFD coupling approach. Chemical
Engineering Science 2021 245(14), 116833.
https://doi.org/10.1016/j.ces.2021.116833.
Montes, I.; Lai, C.; Sanabria, D. Like Dissolves Like: A Guided Inquiry Experiment for Organic
Chemistry. Journal of Chemical Education 2003 80(4), 447.
https: //DOI: 10.1021/ed080p447.
Tivert, A.M.; Vessman J. Pharmaceutical analysis: Overview. Encyclopedia of Analytical

Science (2nd Edition) 2005, pp.78-89.
White C.A.; G.W. Buchanan. Solubility Tests and Recrystallization. CHEM 2203/2204- Organic
Chemistry Laboratory Manual 2022-2023. pp.5-12.
Ying Z. Xin X.; Yuwei P.; Liting X.; Minghua Z. Pre-magnetized Fe0 activated persulphate for
the degradation of nitrobenzene in groundwater. Separation and Purification
Technology 2019, 212, 555-562.
https://doi.org/10.1016/j.seppur.2018.11.074

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CHEM 2203

Experiment 1- Solubility & Recrystallization

Needle like crystals Needle like

Resorcinol Cold: insoluble Cold: insoluble Cold: insoluble Cold: insoluble

Percent recovery of salicylic acid

mass of recovered material

Like-dissolve-like theory explain the ability for solutes to dissolve in solvent

Recrystallizations occur when an impure solid compound mixed with a heated

Techniques to determine if the salicylic acid is pure can be through visual

Tivert, A.M.; Vessman J. Pharmaceutical analysis: Overview. Encyclopedia of Analytical

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