Lab 3_Caffeine_Report

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University of Pennsylvania *

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Chemistry

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Feb 20, 2024

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Caffeine Lab Report 1. Methylene chloride (dichloromethane) is not an environmentally friendly solvent. What are some other solvents that could possibly replace halogenated solvents in this extraction procedure? Generally, what are the ways that coffee and tea are decaffeinated commercially? What are the drawbacks to these methods? Give references. (10 pts) Some other solvents that could be used instead of halogenated solvents for this extraction would be ethyl acetate and toluene. In general, coffee and tea are commercially decaffeinated using DCM, ethyl acetate, and supercritical CO2. This method uses solvents that are not environmentally friendly or are toxic, and traces of DCM (a carcinogen) can remain in the coffee or tea. The other method is the Swiss water process, which avoids having DCM in decaf coffee, but also uses a large quantity of water. And using this much water can remove some of the flavor from the coffee or tea. LINKS 2. Calculate the percent recovery of crude caffeine that was isolated from the tea bags. (5 pts) 3. Calculate the percent yield of the pure caffeine recrystallized from your crude product. (5 pts) 4. What was the melting point of your caffeine? Was it pure? (4 pts) 5. What is the purpose of the sodium hydroxide washes? Include any relevant reaction mechanism(s). (5 pts) The purpose of the NaOH is to remove tannins. These tannins have an acidic OH group which NaOH can deprotonate. In fact, the tannins are polyphenols, meaning they have multiple OH groups so they must be deprotonated multiple times. They will then be positively charged and can move from the organic to the aqueous layer, which is then discarded.
6. What other impurities could be present in the caffeine? How did you try to remove them? (6 pts) The tannins were removed using NaOH as described above. Other impurities include water, which was removed using the drying agent sodium sulfate. Additionally, there can be impurities in the form of chlorophyll and xanthines, for example theophylline and theobromine which are removed by recrystallization. 7. The following chemicals are commonly used organic solvents in an organic chemistry lab. Determine whether each chemical a suitable organic phase when extracting with water. If the chemical is a suitable extraction solvent, determine where the organic layers would be if extracting with each solvent. (10 pts) Chemical Water solubility (g/100 g H 2 O) Density (g/mL) Suitable for extraction? (Y/N) If suitable, top or bottom layer? (T/B) Ethyl acetate 8.7 0.895 Y T Acetone Miscible 0.785 N NA Methanol Miscible 0.791 N NA Dichloromethane 1.32 1.32 Y B Hexane 0.0014 0.659 Y T 8. 400 mL of a solution of aniline in H 2 O (0.125 mg/mL) is extracted with 100 mL of ether. The distribution coefficient or partition coefficient (K p ) for aniline (ether/H 2 O) = 3.5. How much aniline will be extracted into the ether layer? (10 points) 9. If the same solution of aniline was extracted with two 50 mL portions of ether, how much aniline would be extracted in total? Which is a better method? (10 points)
This is a better method because more aniline was extracted (25.81 mg compared to 23.33 mg). 10. We used recrystallization to purify our caffeine. However, caffeine also has an interesting physical property that not all solids possess. What would be another method for purifying the crude caffeine that would take advantage of this property? How might this be advantageous versus a recrystallization? (5 points) The property that caffeine possesses is sublimation, so it can sublime at normal atmospheric pressure. So, sublimation can be used instead of recrystallization because the impurities cannot sublime. This would be more effective because xanthines have a similar solubility to caffeine, reducing the effectiveness of recrystallization, but they cannot sublime.
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