experiment 6 isolation of naproxen
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California Polytechnic State University, Pomona *
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2010L
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Chemistry
Date
Jan 9, 2024
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docx
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Karina Azabache
CHEM 2010L
Experiment 6: Isolation of Naproxen Purpose: The purpose of this experiment is to isolate the active ingredient in the anti-inflammatory drug
Naproxen Sodium.
Procedure: 1. Obtain 1 Naproxen Sodium tablet from your instructor. There is no need to weigh it because each tablet contains exactly 220 mg of Naproxen Sodium. 2. Use a clean “mortar & pestle” to grind the tablet to a fine powder. Transfer the powder to a large test tube. 3. Add 3 mL of ethyl acetate and 1 mL of 3M HCl and mix thoroughly by using the pipette to pull up the liquid and vigorously squirt it back into the tube. Allow the organic phase and aqueous phase to separate. 4. As best you can, pipette out the top organic layer, leaving some behind to avoid transferring any of the blue particulate filler from the capsule or aqueous solution. Transfer the organic layer into another clean test tube. 5. Add in another 2 ml of ethyl acetate to the aqueous acid solution, repeat the mixing and transfer of the organic
phase into the same tube as your first organic transfer. (Never use a contaminated pipette in any reagent bottle or you will contaminate the entire bottle.) Do this once more (extract 3 times for a total of about 7 mL of ethyl acetate). Each time leave the blue particulate filler behind in the aqueous layer. 6.
Save the aqueous phase in case you need to further extract it. When finished with the experiment, dispose of the aqueous fraction in the aqueous waste container. 7. Wash the combined organic layers with 1 mL of brine (i.e., saturated NaCl solution), by thoroughly mixing with a pipette (pull up the liquid with a pipette and squirt it back in). 8. Pipette off the lower brine layer, taking just a bit of the organic solvent with its removal. Your goal is to leave the maximum amount of organic phase (because naproxen
will stay in that phase), yet still remove all of the aqueous phase. Try not to leave any visible trace of water. 9. Add a small amount of anhydrous sodium sulfate for final drying. If there is still suspended particulate matter, you can do a crude filtration by inserting a small plug of cotton in a Pasteur pipette and pipetting the organic phase through that plug into a small, clean, dry pre-weighed round bottom flask or watch glass. Using sodium sulfate will help you avoid having any brine in the pure organic sample, which would contaminate your Naproxen with salt and also make it very difficult to dry your material. It will also affect your yield of product. 10. The ethyl acetate (solvent) is evaporated at the Rotovap (Rotary Evaporator), leaving white crystals (pure Naproxen). 11. Record the weight, obtain a melting point and an IR.
Reaction Scheme:
Chemical list and Chemical Properties:
Compound
Amount
M.W.
(g/mole)
Mol
Density
Melting Point (
℃
)
Boiling Point (
℃
)
Hazards
Naproxen Sodium
220 mg
252.24
0.000872
1.2 ± 0.1 g
/ cm
3
250-251
403.9
Upset stomach,
Nausea, Heartburn, Headache, Drowsiness, or Dizziness
Ethyl Acetate
7 mL
88.11
0.0717
.902 g /
cm
3
-83.6
77.1
Eye/skin irritant highly flammable
3 M HCl
1 mL
36.46
.0288
1.05 g /
cm
3
0
-85.05
Eye, nose, and respiratory tract irritation /
inflammation and pulmonary
edema
Brine
1 mL
76.46
.013
.999 g /
cm
3
-10
215
Serious Eye Damage / Eye Irritation
Carboxylic Acid Naproxen
N/A
230.26
N/A
1.2 ± 0.1 g
/ cm
3
152-155
403.9
Serious Eye Damage / Eye Irritation Respiratory Tract Irritation
Equipment List with Diagrams:
Theoretical Yield Calculation:
Naproxen Sodium 0.22g x 1
mol
252.24
g
= 0.000872185 mol
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a
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