Hurst The Effect of pH on Sodium Benzoate Introduction In this experiment solid sodium benzoate was reacted with aqueous

hydrochloric acid to produce solid benzoic acid. Sodium benzoate is a commonly used food preservative and when placed in a highly acidic environment, such as the Human stomach (pH 2), sodium benzoate reacts and changes to benzoic acid. Aqueous hydrochloric acid was used in this experiment to simulate the acidity of the Human stomach. Observations The production of solid benzoic acid (C6H5COOH) from solid sodium benzoate (C6H5COONA) by the addition of 10% aqueous hydrochloric acid (HCl) was carried out according to the following reaction: C6 H 5COONa ( s ) + HCl (aq ) C6 H 5COOH ( s ) + NaCl ( s ) or alternately:
O ONa O OH

HCl

NaCl

. 2.001 g of sodium benzoate was dissolved in 10.0 mL of water. 4.0 mL of hydrochloric acid was then added to the solution. Additional hydrochloric acid was than added drop wise until the pH of the solution reached pH 2; 5.2 mL of hydrochloric acid was added in total. After the pH had reached 2 it was cooled in an ice bath until the temperature of the solution was less than 10 C. The solution was then filtered and washed by vacuum filtration for 20 minutes. The remaining product was than weighed.

Hurst Data Experimental Data Mass of sodium benzoate Volume of hydrochloric acid Volume of water Mass of filter paper Mass of measurement boat Mass of benzoic acid pH Calculations Data Value 2.001 g 5.200 mL 10.000 mL 0.124 g 1.725 g 2.287 g 2

Theoretical Yield C6 H 5COONa = 2.001g C6 H 5COONa 1 mol C6 H 5COONa 144.100 g C6 H 5COONa 1 mol C6 H 5COOH 1 mol C6 H 5COOH 122.100 g C6 H 5COOH 1 mol C6 H 5COOH = 1.695 g C6 H 5COOH

Actual Yield C6 H5 COOH = 4.136 g (1.725 g + 0.124 g) = 2.287 g

Percent Yield C6 H 5COOH = Results Benzoic acid (C6H5COOH) was obtained through the acid/base reaction of 10% hydrochloric acid (HCl) and sodium benzoate (C6H5COONa). The percent yield for the experimental reaction was calculated at 134.926%. At room temperature sodium benzoate was a water soluble white crystalline solid with a molecular weight of 144.1 amu. The experimentally obtained benzoic acid at room temperature was a nearly water insoluble white powder solid with a molecular weight of 122.1 amu and a melting point of 122 C. Discussion The purpose of this lab was to discover if, at a simulated pH of the human stomach, sodium benzoate would react with the acid in the stomach and form a new compound. Sodium benzoate is a commonly used a food preservative as it inhibits the growth of bacteria, yeasts, and molds. Acids found in the human stomach are acidic and this acidity was stimulated using hydrochloric acid (HCl). It was found that at a pH of 2 sodium 2.287 g C6 H 5COOH 100 = 134.926% 1.695 g C6 H 5COOH

Hurst

benzoate was converted to benzoic acid in the presence of hydrochloric acid according to the chemical equation found in the observations section. The major problem to be noted with this experiment was that the percent yield of benzoic acid obtained was greater than 100%. Obviously the actual product yield can not be greater than the theoretical yield produced mathematically. The most apparent solution to this problem was in the excess of water that was still found in the benzoic acid solution filtered by vacuum filtration. Possible solutions to this issue include allowing additional drying time via vacuum filtration, long-term air drying, or using an oven set at a temperature lower than 90 C (to prevent sublimation) for a period of time . Using any of these methods would have eliminated any excess water left in the benzoic acid and thus decreasing the mass of the sample and linearly the percent and experimental yields. Although it is impossible at this level to do determine the exact identity of the compound found in the benzoic acid solution it is possible to ascertain that a new compound was formed. When the pH of the aqueous sodium benzoate solution dropped to a point low enough for the conversion reaction of sodium benzoate to benzoic acid to occur a precipitate dropped out of solution. Examining the characteristic water solubility of sodium benzoate and benzoic acid it becomes apparent that the compound that dropped out of solution was not sodium benzoate (water solubility 61.2) but most likely benzoic acid (water solubility 0.34). Combining this inference with the chemical equation of the reaction of sodium benzoate with hydrochloric acid it becomes apparent that benzoic acid was the likely product of the reaction.