Dina Karina Lab performed: 1/22/15
Chem 2203-012 Report due: 1/29/15
TA: Kavitha Akula
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
Objective
The purpose of this experiment is to familiarize oneself with the general procedures determining a partition coefficient at the microscale level and learn in weighing milligram quantities of materials on an electronic balance, the use of automatic pipets, the use of transfer pipet, and the use of a vortex mixer. Also, to familiarize oneself with extraction
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Experiment 4B
After dissolving benzoic acid in 1.0mL CH2Cl2 and 1.0mL 10% NaHCO3 solution, two layers are created, the top layer is 10% NaHCO3 solution and the bottom is CH2Cl2.
After putting the CH2Cl2 to a beaker containing the drying agent anhydrous sodium sulfate, a sticky white solid was recovered.
After heating, a very few amount of solid white-greyish benzoic acid was recovered.
Calculations
Questions
1. The purpose of sodium sulfate is as the drying agent. I rinsed the sodium sulfate with additional methylene chloride to have a more accurate amount of benzoic acid in case the benzoic acid precipitated.
2. a. It is not necessary because as the drying agent it does not influence the substrate concentration.
b. If it is too much the all of the solution will precipitate including the benzoic acid. If it is too little than then it will take a long time to heat the solution in order to acquire the benzoic acid.
3. a. The first error will be when transferring the benzoic acid from the weigh paper to the vial. The benzoic acid is spilled. Then, the second one will be when pipetting and transferring the methylene chloride because I might spill some of the methylene chloride. The third one will be when pipetting the two layers, either I could not pipet all of the bottom layer or I accidentally pipet the top layer.
b. As I mentioned above that I spilled some of the benzoic acid therefore the initial mass
Sodium sulfate has a molar mass of 142.04 g/mol. It has a melting point of 884°C and can be an irritant.
The wet, crude product was placed into the 50 mL Erlenmeyer flask. Small amounts of CaCl2 were added to dry the solution. The flask was sealed and the mixture was swirled and left to settle. Once
A few sources of potential error are as follows: loss of product on glassware throughout the experiment, inadequate measuring of chemicals, "impure" chemicals being worked with, and loss of final product during crystallization processes.
Mass of dry recrystallized benzoic acid is smaller than the initial mass because the impurities are removed. Experiment
Wash (swirl and shake) the organic layer with one 10-mL portion of water and again drain the lower aqueous layer. Transfer the organic layer to a small, dry Erlenmeyer flask by pouring it from the top of the separatory funnel. Dry the crude t-pentyl chloride over 1.01 g of anhydrous calcium chloride until it is clear (see Technique 12, Section 12.9). Swirl the alkyl halide with the drying agent to aid the drying.
Experiment 55 consists of devising a separation and purification scheme for a three component mixture. The overall objective is to isolate in pure form two of the three compounds. This was done using extraction, solubility, crystallization and vacuum filtration. The experiment was carried out two times, both of which were successful.
1) Pour 25 mL of the 1 M hydrochloric acid into the beaker and rinse the solid by swirling the acid around in the bottom of the beaker.
The objective of this experiment is to separate a 50:50 mixture of benzoic acid and benzil by using macroscale extraction. In the experiment, organic solvent diethyl ether is used. After adding 1.0 gram of the 50:50 mixture of benzoic acid and benzil to a 25ml Erlenmeyer flask, diethyl ether was added to the flask to dissolve the mixture. Benzoic acid and benzil dissolve in diethyl ether. Once the mixture dissolved in
One milliliter of 6.00-M phosphoric acid was placed into a 125-mL Erlenmeyer flask using a volumetric pipette. Using a slightly larger pipette, six milliliters of 3.00-M sodium hydroxide was transferred into a 50-mL beaker. Then a disposable pipette was used to slowly mix the sodium hydroxide into the phosphoric acid while the solution was swirled around. Then both the beaker and flask were rinsed with 2-mL of deionized water and set aside. A clean and dry evaporating dish was weighed with watch glass on a scale. Then the solution was poured into the dish and the watch glass was placed on top. The solution was then heated with a Bunsen burner to allow for the water to boil off to reveal a dry white solid. After the dish cooled to room temperature it was once again weighed and the new mass was recorded.
If necessary the centrifuge can also be used to further separate the two layers. A final means of drying the ester product is the addition of granular sodium sulfate.
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
The purpose of this experiment was to use solvent extraction techniques in order to separate a mixture consisting of a carboxylic acid (p-toulic acid), a phenol (p-tert-butylphenol), and a neutral compound (acetanilide). Extraction is the process of selectively dissolving one or more of the compounds of a mixture into an appropriate solvent, the solution that contains these dissolved compounds is called an extract (Manion, 2004).
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
Discard the solution in the appropriate container as directed to you by your lab instructor.
Objective: The objective of this experiment is to use acid-base extraction techniques to separate a mixture of organic compounds based on acidity and/or basicity. After the three compounds are separated we will recover them into their salt forms and then purify them by recrystallization and identify them by their melting points.