Synthesis of Aspirin.edited

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Technical University of Mombasa *

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Chemistry

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Nov 24, 2024

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docx

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1 SYNTHESIS OF ASPIRIN Student’s Name Institutional Affiliation Course Instructor’s Name Date
2 Synthesis of Aspirin Objective To react 2.1 gram of salicylic acid with 5 gram of acetic anhydride in the presence of concentrated sulphuric acid to form Aspirin. To prepare benzoic acid by reacting 5 gram of ethyl benzoate with 50 cm3 of sodium hydroxide, and finally test the purity of Aspirin and the functional group present. Materials and Equipment’s Thermometer Stopwatch Magnetic stirrer Erlenmeyer flask Test tube Dropper Clamp and stand Flat bottomed flask Beaker Buchner funnel Filter paper Spatula
3 Reflux apparatus Stirrer rod NAME FORMULA AND STRUCTURE MW (G/ ML) MP ( ) BP ( ) DENS ITY (G/C M3) COLOU R SOLID/L IQUID WATER H2O 18.0 2 0 100 1 colorless liquid ETHANOL C2H60 46.0 1 - 114. 5 78.5 0.789 colorless liquid SODIUM HYDROXIDE NaOH 39.9 97 318. 4 1388 2.13 white solid IRON (III) CHLORIDE FeCl3 162. 2 306 315 2.9 Dark green solid HYDROCHLORI C ACID HCl 36.4 58 - 114. 22 - 85.0 5 1.2 Colorless liquid CONCENTRATE D SULPHURIC ACID H2SO4 98.0 79 10 337 1.83 colorless liquid
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4 SALICYLIC ACID C7H6O3 138. 12 211 158. 6 1.44 White crystals solid BENZOIC ACID C7H6O2 122. 12 122. 3 249. 2 1.27 colorless liquid METHYL BENZOATE C8H8O2 136. 15 -15 199 1.08 colorless liquid ASPIRIN C9H8O4 180. 158 135 140 1.4 White crystals solid ACETIC ANHYDRIDE C4H6O3 102. 09 - 73.1 139. 8 1.08 colorless liquid
5 Procedure Procedure observations 1. Weigh 2.1 gram of salicylic acid 2. Put this mass into an Erlenmeyer flask in a water bath maintained at 45 degrees Celsius to 50 degrees Celsius. 3. Add 5 ml of acetic anhydride into the Erlenmeyer flask. 4. Add a magnetic stirrer as the flask is in a heating mantle that allows stirring. 5. Add five drops of concentrated sulphuric acid. 6. Allow the Erlenmeyer flask to cool to allow the product to recrystallize. If it doesn't recrystallize, scratch the inside of the wall with an ice cube. Cloudy so formed 7. Add 30 ml of ice-cold water, and place it in the ice cubes. 8. Set the vacuum filtration apparatus 9. Transfer the solution into the Buchner funnel to allow filtration 10. Add 30 ml of water to the Buchner funnel will help to get rid of impurity. 11. Collect a tiny amount of residue for purity analysis 12. Add five ethanol to the filtrate on a
6 heating mantle to recrystallize 13. Add 40 ml of water into the beaker and allow it to cool to room temperature for recrystallization. Scratch the walls with an ice cube to allow the crystals to form 14. Put the beaker in the ice cube and set up the vacuum filtration apparatus. 15. Put the solution in the Buchner funnel to allow filtration. Rinse the funnel with ice-cold water after filtration 16. Take a small amount of the filtrate (pure Aspirin) for analysis. Procedure for Purity Analysis FeCl3 Test Procedure Observations Place a small amount of salicylic acid into a beaker Colorless solution To this beaker and the two other beakers containing pure and crude Aspirin, add I ml of 95% ethanol. Colorless solution Add 1 ml of 25 % into the three beakers In the Crude Aspirin Purple color In salicylic acid Purple color Pure Aspirin No colorless
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7 Saponification of Ester Preparation of Benzoic acid Objective To react 5 gram of ethyl benzoate with 50 cm3 of sodium hydroxide in the presence of hydrochloric acid to produce benzoic acid Procedure procedure Observation 1. Weigh 5 gram of ester, ethyl benzoate, in a conical flask 2. Add 50 cm3 of NaOH into the solution. 3. Add boiling chip and turn on the heating mantle. 4. Set up the reflux apparatus, and perform a reflux experiment 5. Cool the mixture to room temperature and transfer into a beaker 6. Add 30 cm3 of hydrochloric acid into the mixture in the beaker White precipitate formed 7. Setup the vacuum filtration apparatus and filter the reaction mixture. Wash with water to allow the total transfer. 8. Transfer the residue into a beaker 9. Add 100cm3 of water into the Clear solution formed
8 benzoic acid and stirrer continuously, and heat to 60 cm3 to 20 cm3 to all the benzoic acid to dissolve. 10. Filter the solution via vacuum filtration and allow it to recrystallize 11. Transfer the filtrate into a beaker, and allow it to cool to room temperature Cloudy solution formed 12. Set up the vacuum filtration and filter pure benzoic acid. Wash out the beaker with water to ensure complete transfer 13. Transfer the benzoic acid crystals into a preweighed petri dish. And allow it to dry and weigh. Results Synthesis of Aspirin 2.1 g Salicylic acid 5 ml of acetic anhydride 1 ml of concentrated sulphuric acid
9 From the equation provided, the mole ratios are 1:1 Hence the number of moles of salicylic acid is equal to the number of moles of Aspirin. The number of moles of salicylic = weighed mass/ relative mass Weighed mass = 2.0g Relative mass = 138.12 g/mol Thus, number of moles = (2.0g/138.12g/mol) = 0.0145moles These moles are equal to those in aspirin Thus, theoretical weight = no. of moles * MW MW of Aspirin = 180.158 g/mol Theoretical weight = 0.0145 *180.158 = 2.6087g Actual weight = 1.1 g % percent yield = (actual weight/theoretical value) *100 = (1.1g/2.6087g) *100 = 42.1666% = 42.17% Preparation of Benzoic acid 0.9 g of Methyl benzoate 50 cm3 of sodium hydroxide
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10 0.54g Benzoic acid From the equation provided, the mole ratios are 1:1 Hence the number of moles of methyl benzoate is equal to the number of moles of Benzoic. The number of moles of methyl benzoate = weighed mass/ relative mass Weighed mass = 0.9g Relative mass = 136.15 g/mol Thus, number of moles = (0.9g/136.15g/mol) = 0.0066moles These moles are equal to those in Benzoic Acid Thus, theoretical weight = no. of moles * MW MW of benzoic acid = 122.12g/mol Theoretical weight = 0.0066 *122.12 = 0.805992g Actual weight = 0.54 g % percent yield = (actual weight/theoretical value) *100 = (0.54g/0.805992g) *100 = 66.9982% = 66.99% Discussion 2.1 g of salicylic acid was reacted with 5 ml of acetic anhydride in the presence of 1 ml of concentrated sulphuric acid, which acted as a catalyst. When concentrated sulphuric acid was
11 added to the solution, a cloudy solution was formed, which indicated Aspirin's presence. The solution was carried out at 50 degrees Celsius for 5 minutes, which ensures enough heat and time for everything to react. The product (Aspirin) was precipitated, collected, and recrystallized to purify it. Water was added to the funnel to get rid of impurities. Acetic anhydride is eliminated by the rinsing of the funnel and the beaker with water. When iron (III) chloride was added to either the pure or crude Aspirin and salicylic color change was observed, which identified if the pure Aspirin was pure. In the purity test, ethanol was employed as it has a low boiling point and high volatility hence efficient recrystallization. In the test tube containing salicylic acid and crude Aspirin, a dark purple color was observed to indicate that the solution in those test tubes contained a phenol group with an OH connected directly to it. The test tube with pure Aspirin color change was not observed; hence pure Aspirin was synthesized. Furthermore, the results formed when FTIR analysis was carried out an OH, CO (carbonyl group) were marked by peaks in those regions. In the preparation of Benzoic acid, 5 g of ethyl benzoate was reacted with 50 cm3 of sodium hydroxide in hydrochloric acid as a catalyst and hence creating a conducive environment for the reaction. The formation of the white precipitate by the addition of hydrochloric acid indicated the formation of benzoic acid. This product was filtrated and recrystallized to form pure benzoic acid. To form crystals, the solution was allowed to cool at room temperature, and during filtration, water was added to ensure the total transfer of the solution of benzoic acid. Conclusion This lab experiment was a success by forming Aspirin, by reacting 2.1-gram salicylic acid by 5 ml acetic acid in the presence of concentrated sulphuric acid. Also, the preparation of
12 benzoic acid by reacting methyl benzoate with sodium hydroxide in hydrochloric presence was a success as pure benzoic acid was reacted. In both, 100 % yield was not observed. In the synthesis of Aspirin, 42.17% was observed, while 66.99% yield was observed in benzoic acid preparation. A significant reason for this discrepancy was due to transfer losses. That is, total transfer was not a success. Also, the reflux in the preparation of benzoic acid may not have gone to completion. Some of the Aspirin and benzoic acid may have dissolved in water. The results were taken in rounded figures for great precision. References https://labmonk.com/synthesis-of-aspirin-from-salicylic-acid-using-acetic- anhydride#:~:text=Principle%3A%20Synthesis%20of%20aspirin%20from,a %20molecule%20of%20acetic%20acid . https://labmonk.com/synthesis-of-benzoic-acid-from-alkyl-benzoate
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