Separating Acids and Neutral Compounds by Solvent Extraction

2. To titrate a hydrochloric acid solution of “known” concentration with standardized 0.5M sodium hydroxide.

There are various techniques to separate a mixture of compounds from each other. One of the commonly used way to isolate compounds from a mixture of two compounds is called extraction. This method of extracting two compounds from each other relies on the different solubility of the compounds in two different solvents.

This experiment combined all the knowledge of the previous labs performed throughout the semester. An unknown mixture containing an organic acid or base and an organic neutral compound in nearly equal amounts needs to be separated to its separate components. An understanding of solubility, extraction, crystallization and vacuum filtration is necessary in order to

In the first acid extraction of benzocaine, the compound was dissolved in the organic solvent of dichloromethane. When the mixture was shaken with HCl, benzocaine’s amine group gained a proton and became more soluble in water than dichloromethane. This allowed the newly formed hydrochloric salt to migrate to the aqueous layer. However, the addition of NaOH to the acidic aqueous layer regenerated benzocaine by deprotonation, making it insoluble in the aqueous layer. The precipitation of an ionic salt was therefore recovered by vacuum filtration and had a tested melting point range of 85.1C-87.4C compared to 88C-90C, the literature melting point of benzocaine. The similarity in melting point ranges, but low percent yield of 30.37% proves that the extract was somewhat successful. Lower yields may be the result of spillage performed in the lab. In the second basic extraction, the organic layer now included benzoic acid and benzamide. When treated with NaOH to deprotonate benzoic acid, the newly formed sodium benzoate transitioned to the aqueous layer as a sodium salt. Benzoic acid is regenerated once again after the addition of HCl and became insoluble in the aqueous layer after protonation. Its precipitation was then filtered out for a 65.87% recovery. Compared to its literature melting point of 122.41C, the resulting 120.9C-123.5C melting range of the sample also supports the accuracy of the separation due to its similarities and high percent yield. In conclusion, the usage of base and acid liquid extraction was mostly successful in this experiment because it was able to efficiently and properly isolate the impure mixture into two separate components of benzocaine and benzoic acid. By performing the techniques of extraction and vacuum filtration, the similarities between literature and tested

Me and my lab partner, obtained a mixture of a un known proportion from the instructor and then flow the guide line in our lab manual to separate the mixture by applying the separation method motioned in our lab manual pages 33-40 . In this experiment, the separation methods were decantation,

The objective of this extraction experiment was to achieve a comprehensive understanding, as well as master the practice, of the technique of separating various individual components of a compound.

In order to isolate benzoic acid, benzocaine and 9-fluorenone, each component needed to be separated from one another. All three compounds began together in one culture tube, dissolved in methylene chloride and formed into a homogenous mixture. In this culture tube, two milliliters of aqueous three molar hydrochloric acid was added, which immediately formed two layers, the top acidic aqueous layer was clear in color and contained benzocaine, and the bottom organic formed was yellow and contained benzoic acid and 9-fluorenone. Benzocaine’s amino group is protonated by the aqueous layer hydronium. This protonation forms the conjugate acid of benzocaine, benzocaine hydrochloride. Thus, the conjugate acid, benzocaine hydrochloride is a salt in which is soluble in water and furthermore can be isolated from the organic mixture. When testing out the pH levels in benzocaine, the pH test strip was dark blue in color, indicating a pH level of around 5 to 7. When isolating benzoic acid, two milliliters of aqueous three molar sodium hydroxide was added, which deprotonates the carboxylic group in benzoic acid, forming its conjugate base, sodium benzoate. As with benzocaine hydrochloride, sodium benzoate is a water soluble ionic salt in the aqueous layer that can then be separated from the bottom organic layer containing the 9-fluorenone. The pH test strip was a vibrant red for benzoic acid, indicating a pH of 2. Now the 9-fluorenone is left, deionized water is added to remove any excess

These layers can be separated through the use of a seperatory funnel which drains the bottom layer into a separate container. This method uses the understanding of partition ratios of solutes to different paired solvents to produce an equilibrium leaning towards one solvent over another, thereby extracting a compound from one liquid to the other (Padias 128-37). For example, consider a mixture containing two solutes, solute A and solute B, and two immiscible solvents, solvent A and solvent B. If solute A dissolves well into solvent A, but not very well into solvent B, and solute B dissolves well into solvent B but not very well into solvent A, there would be a higher ratio of solute A in solvent A than in solvent B, and a higher ratio of solute B into solvent B than in solvent A. One can then see that, through the use of different solvents, two dissolved solutes can be separated from a mixture. This ratio of a solute concentration to different solvents is defined by K, the distribution constant. Successive filtrations yield’s a higher percentage of products.

1.5mL of phosphoric acid including 3-4 boiling chips were also added to the 25mL flask. The short path distillation apparatus was set up as shown in Figure 1. A heating mantle was used to heat up the 25mL flask. The solution was distilled to the receiving flask until a small amount of liquid remained in the initial RBF flask. At this point the presence of thick grey smoke pulling over into the entire apparatus was observed. The apparatus was then left to cool down. Through the use of pasture pipette, the aqueous layer from the distilled solution was drawn out. Sodium carbonate was then added to the remaining organic solution in order to check the pH and to verify the basicity of the solution. The aqueous layer was again drawn out from the solution. Next, 0.5g of sodium sulfate was added to the remaining organic layer and was swirled until the liquid appeared to be dry and clear. The alkenes were transferred into a clean 10mL flaks using another clean pasture pipe. The apparatus from the first distillation was rinsed off with

After about 1 minute of shaking, the two layers separated. The organic layer on the top layer (consisted of ethyl acetate and naphthalene) collected for further experiment; by adding Sodium Sulfate into organic phase and filtering the Na2So4 from the solution using the wool. The dried organic layer was weighed to get its mass and the residue of Na2SO4 were rinsed with ethyl acetate under vacuum (rotary evaporator). The acid extract on the bottom layer which is a combination of benzoic acid and NaOH were collected in the 50 mL Erlenmeyer beaker for the recovery of acid.

The crude product was washed by taking the reaction product in the separatory funnel and adding 23 mL of deionized H2O. The mixture was shaken and allowed to settle until layers were observable. The top layer was the desired product and approximately 25 mL of aqueous layer was extracted from the separatory funnel. Next, 25 mL of 5% NaHCO3 was added to the separatory funnel in order to neutralize the acid. This mixture was swirled, plugged with the stopper and inverted. Built-up gas was released by turning the stopcock to its opened and closed positions, releasing CO2 by-product. This was done four times in one minute intervals. The solution was allowed to settle until layers were observable. The bottom layer that contained salt, base and water was extracted from the separatory funnel. The crude product was washed again as mentioned previously.

Throughout the course of the experiment, the weight of the beaker and liquid, the weight of the Alka-Seltzer tablet, the weight of the beaker with liquid plus the weight of the tablet, and the weight of the beaker with all of the contents after the bubbling ceased remained roughly constant and did not vary widely. However, a trend is able to be seen in Figure 1. It is clear that as the mL of vinegar used in each experiment run increased, the mass percent of NaHCO3 increased as well. During the construction of Figure 1, experiment runs four and six were deleted to create the expected graph which consists of a gradual increase and eventually leveling off into a plateau.

In this experiment, 0.31 g (2.87 mmol) of 2-methylphenol was suspended in a 10 mL Erlenmeyer flask along with 1 mL of water and a stir bar. The flask was clamped onto a hotplate/stirrer and turned on so that the stir bar would turn freely. Based on the amount of 2-methylphenol, 0.957 mL (0.00287 mmol) NaOH was calculated and collected in a syringe. The NaOH was then added to the 2-methylphenol solution and allowed to mix completely. In another 10 mL Erlenmeyer flask, 0.34 g (2.92 mmol) of sodium chloroacetate was calculated based on the amount of 2-methylphenol and placed into the flask along with 1 mL of water. The sodium chloroacetate solution was mixed until dissolved. The sodium chloroacetate solution was poured into the 2-methylphenol and NaOH solution after it was fully dissolved using a microscale funnel.

Experiment 4A: Determination of a Partition Coefficient for Benzoic Acid in Methylene Chloride and Water, and Experiment 4B: Solvent Extraction I: Acid-Base Extraction Using the System Benzoic Acid, Methylene Chloride, and Sodium Bicarbonate Solution

In this experiment were used three separation techniques: extraction, sublimation and recrystallization. During the first method, 0.70 g sample of salicylic acid-naphthalene mixture was dissolved in 10 ml of diethyl ether. The solution was placed in a separatory funnel and 10 ml of saturated aqueous sodium bicarbonate solution was added to it. After the initial gas was