The Extraction of Benzoic Acid Organic Chemistry Lab 1 Lauren Parrette 9-6-2013

Introduction Often, chemists observe and measure the mixture of compounds in the natural world. Based on these observations and measurements, they try to apply their discovery to preexisting laws, theories, or data findings. Most importantly, they are usually prone to separate a mixture of compounds in order to configure their individual structures, and to identify reactivity and other unique properties. Mixtures of compounds can be separated in many ways.

Extraction is used to describe the partition processes based on differences of substances in two different immiscible solvents, and it is a very common laboratory procedure used when isolating or purifying a product. The partition could be between two liquid phases or between a liquid and a solid phase, which depends on the subject of the experiment. (Pg. 128, Padias) First, the liquid-liquid extraction uses the distinct solubilities of different solutes in immiscible solvents, and as a consequence, two obvious layers will form. The top layer contains the solvent that has lower density whereas the lower layer will have higher density. Usually, the two layers are organic, which is insoluble, and aqueous, which is soluble, respectively. Usually, a chemist employs the Separatory Funnel to operate the liquid-liquid extraction. (Pg. 129, Padias)

In this procedure, a mixture of benzoic acid, methyl orange, and cellulose was obtained, and the purpose of this experiment is to separate benzoic acid from the mixture. Ether was used as a solvent in this experiment because its oxygen atom has nonbonding electron pairs that can form hydrogen bonds with other molecules having O-H or N-H bonds. According to the like dissolves like concept, ether will attract benzoic acid and methyl orange by hydrogen bonding. Cellulose on the other hand is bulky and inflexible due to hydrogen bondings aligning with each other. It was filtered out by using the Vaccum Filtration technique, which is used to separate a

solid from a liquid solution. In the absence of cellulose, the NaOH was added to the mixture of benzoic acid and methyl orange, which formed two layers: an aqueous layer and an organic layer. The aqueous layer contained water and salt of the benzoic acid. On the other hand, the organic layer was taken up by methyl orange and ether since they both have limited solubility in water. The ether, or organic, layer is on the top because ether has lower density than water. The salt of benzoic acid was extracted since it is in the aqueous layer, which is on the bottom. To obtain a solution of benzoic acid, the filtrate was later acidified with HCl. Experimental

First, 4 g of the crude benzoic acid mixture was obtained and placed in a 25 mL Erlenmeyer flask. Then, 50 mL of diethyl ether was added to the 125 mL Erlenmeyer flask. Some boiling stones were added to the Erlenmeyer flask so as to prevent bumping before the mixture was heated. Heating was stopped when it just started boiling. Next, Buchner funnel vacuum filtration was used to remove the ether insoluble material from the solution. The filtrate was added in a 500 mL separatory funnel and then 30 mL of 1M NaOH was added. As the two layers formed in the separatory funnel, the aqueous layer was drained into a 250 mL beaker. The addition of 30 mL of 1 M NaOH was repeated again so as to drain all the benzoic acid residue. The aqueous extraction solutions were then cooled on ice. Lastly, the solution was acidified with 50 mL of 6 M HCl. Collect the solid precipitate with a Buchner funnel by using vacuum filtration. (Pg. 2122, Ochem Lab Mannual)

Results:

When the ether was heated, the boiling point was reached within 30 seconds. It was seen that the brownish solid was left on the filter paper when the first Buchner filtration was operated. After disposing cellulose, the filtrate, faint yellow-brownish, was poured into a separatory funnel. There were no layers formed at that time. When a 30 mL of 1 M NaOH was added, two layers appeared. The top layer was transparent with a spot of orange color, and the bottom layer was slightly yellow. The solution, which was the bottom layer drained into a beaker, was added with a 50 mL of 6 M HCl. A sight of pink color was immediately observed when the hydrochloric acid was added. After cooling the filtrate with ice, more and more faint pink precipitate/flakes formed gradually. Originally, the mass of the benzoic acid mixture was 4.00 g, but only 2.92 g of the pure benzoic acid was produced. Consequently, percent composition = 2.92 g of the pure benzoic acid/ 4.00 g of the crude mixture of benzoic acid x 100 = 73.00%. Discussion: Ether has a boiling point 94.28F (34.6C), which is only several degrees above normal room temperature. Its low boiling point explains why it was heated up extremely fast in comparison to other solvents, for example, water. It is flammable and in order to avoid fire hazard, it was heated on a steam bath, which will work for ether because of its low boiling point. In addition, ether is characterized by an oxygen atom bonded to two alkyl groups, so it is polar and prefers to have hydrogen bonding with other polar compounds such as methyl orange and benzoic acid from this experiment. Its density is 0.7 g/mL, which is lower than waters density, 1.0 g/mL. This is the reason that the ether layer was on top of the water layer. The cellulose, the brownish precipitate observed during experiment, was filtered out at the beginning. Cellulose (see Figure-1) is a natural polysaccharide consisting of a long chain of linked sugar molecules, which gives its remarkable strength. It is very bulky and inflexible, in a sense that it is usually

not soluble. Also, it is not polar because of its symmetric structure, so it did not dissolve in ether according to like dissolves like concept. Since cellulose is flammable and usually decomposes at a temperature that is slightly above room temperature, it does not have a boiling point. The brown precipitate seen in the funnel was actually the break down from cellulose (Senese, 2010). A spot of orange appeared in the organic layer indicates that the methyl orange was present. Since it is polar, it dissolves in ether by hydrogen bonding. The bottom layer is made of water and salt (the product of benzoic acid and sodium hydroxide). It was an acid-base reaction, or a neutralization reaction, that sodium hydroxide deprotonated the benzoic acid and induced it to form a salt with sodium ion (see Figure-2). The reason that ether filtrate turned slightly pink when the hydrochloric acid was added is that there were some methyl orange residue, which acts as an indicator, remained in the filtrate. It was not long for all the benzoic acid to precipitate in the funnel because benzoic acid has extremely high boiling point and melting point. Once it was placed in a jar of ice, the precipitate/flakes formed faster. Out of 4.00 g of the crude benzoic acid mixture, only 2.92 g of the pure benzoic acid was obtained. It was approximately 73.00% of the crude benzoic acid mixture. There were several factors that resulted the high measure of impurities. First, the crude mixture contained the methyl orange and cellulose. They both have higher molecular weight, respectively 327.33 g/mol and 630.00 g/mol, than benzoic acid does. Therefore, a small fraction of cellulose or methyl orange present in the filtrate might lead to such a high measure of impurity. While the aqueous layer, includes the benzoic acid, was drained into a flask, few drops of ether, might contain methyl orange, from the top layer was also accidentally drained. Secondly, transferring solids from a container to another container also contributes to some loss. Last but not least, cooling the filtrate will form the benzoic solid, but it is possible that not all the

benzoic solid precipitated out of the filtrate. Those three factors might contribute to the loss of pure benzoic acid.

Figure-1: Cellulose

Figure-2: The Reaction of Benzoic acid with Sodium Hydroxide

References: http://antoine.frostburg.edu/chem/senese/101/consumer/faq/what-is-cellulose.shtml