SOLUBILITY OF BENZOIC ACID TO WATER AND ETHANOL

› Solubility of Benzoic acid to Water

The solubility of benzoic acid to water varies in temperature, where it has low solubility
in cold or room temperature. The reason for the low solubility of benzoic acid in water at
room temperature/cold temperature is the carboxylic group is only polar to water, a polar
solvent, and the carbon backbone (benzene) is nonpolar, thus having a hard time to make
it soluble. There are no internal stabilizing structure that favor carboxylate, -COO(-), over
carboxylic acid, -COOH. But when the temperature is increased, the solubility increases
because some of the increased energy sufficiently lengthens the hydrogen-bonds, so that
ionization occurs. When ionization occurs, the ions will dissolve in the water.
Solubility of benzoic acid water in terms of temperature
Solubility (g/L) Temperature
1.7 g/L 0 °C
2.7 g/L 18 °C
3.44 g/L 25 °C
5.51 g/L 40 °C
21.45 g/L 75 °C
56.31 g/L 100 °C

› Solubility of Benzoic acid in Ethanol

The solubility of benzoic acid to ethanol is high whether it is in room temperature or
when the temperature is increased. The reason for this is the reaction between the
carboxylic acid substituent present in the benzoic acid and the ethanol (Fischer
esterification, thus making the benzoic acid more soluble. The reaction is further
enhanced when the solution is heated.

Solubility of benzoic acid in ethanol in terms of temperature

Solubility (g/L) Temperature
25.4 g/L -18 °C
47.1 g/L 15 °C
52.4 g/L 19.2 °C
55.9 g/L 23 °C

References:
 Seidell, Atherton; Linke, William F. (1952). Solubilities of Inorganic and Organic
Compounds. Van Nostrand. Retrieved 29 May 2014.
 http://chemister.ru/Database/properties-en.php?dbid=1&id=679
 https://sciencing.com/benzoic-acid-slightly-soluble-water-6392778.html
 https://pubchem.ncbi.nlm.nih.gov/compound/Benzoic-acid
 https://www.quora.com/Why-is-benzoic-acid-more-soluble-in-ethanol
 https://www.quora.com/What-happen-when-ethanol-reacts-with-benzoic-acid
 https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modul
es_(Organic_Chemistry)/Carboxylic_Acids/Reactivity_of_Carboxylic_Acids/Fisch
er_Esterification