EXPERIMENT 12 UV/VIS Spectroscopy and Spectrophotometry: Spectrophotometric Analysis of a Commercial Aspirin Tablet
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1 EXPERIMENT 12 UV/VIS Spectroscopy and Spectrophotometry: Spectrophotometric Analysis of a Commercial Aspirin Tablet utcomes After completing this experiment, the student should be able to: 1. Prepare standard solutions. 2. Construct calibration curve based on Beer s Law. 3. Use Beer s Law to determine molar absorptivity. 4. Explain the fundamental principal behind spectrophotometric analysis. Introduction Acetyl salicylic acid (ASA) is one of the oldest synthetic drugs. First synthesized in Germany by the Bayer company and marketed under the name Aspirin it has remained one of the most popular over the counter drugs of all time. Its main effect is as a pain killer and fever depressant, but in addition there is strong evidence that in low daily dosages it lowers the incidence of heart attacks. In the last few decades other drugs such as acetaminophen (commercial trade name Panadol, also Tylenol) and ibuprofen (trade name Advil) have taken much of the market for ASA, but ASA remains an important and widely used medicine. Drugs, in addition to their active compound, often contain other inactive ingredients (called excipients in the pharmaceutical industry) such as binders, fillers, dyes, drying agents, etc. The content of active ingredient in a tablet will always be stated on the package. In this experiment we will determine the percent active compound in a commercial aspirin tablet. Aspirin is the trade name for acetylsalicylic acid (ASA). The ASA in the tablet will be reacted with Fe 3+, forming an intensely violet coloured complex. The concentration of the complex will be determined by means of spectrophotometry, using a UV/VIS spectrophotometer. Finally, we will be able to calculate the weight and the weight% of ASA in the commercial tablet. The determination of acetyl salicylic acid by spectrophotometry Acetylsalicylic acid is the acetate (ethanoate) ester of salicylic acid, 2-hydroxybenzoic acid. The acetyl ester is rapidly hydrolyzed to the salicylate anion in basic medium, as shown in the following reaction. C H CH 3 + 3H + CH 3 C + 2H 2 Acetyl salicylic acid Salicylate dianion acetate anion nce the de-esterification is complete, the solution is acidified, and FeCl 3 is added. The salycilic acid will react with the Fe 3+ to form a coloured complex ion: H + + Fe(H 2 ) 3+ 6 Fe(H 2 ) 4 +H 2 +H
2 The spectrum of the Fe salicylate complex was shown in figure 1, plotted as T vs. wavelength. Note that the lowest transmission (i.e., the largest absorption of light) is in the blue green and yellow areas of the spectrum, resulting in the violet colour. Maximum absorption (minimum transmittance) is just above 500 nm, and the concentration measurement will be done at this wavelength. In order to calculate the concentration of the complex we would need to know the value of ε and l. Instead, we will measure the absorbance of Fe-salicylate complex solutions of known concentration, and plot the absorbances of a number of such known solutions vs. the concentration. This is known as a calibration curve. The calibration solutions are prepared by first making a solution of the Fesalicylate complex of known concentration. This solution is called the stock solution. Next we make 5 standard solutions by diluting a known amount of stock solution. The Absorbance of each of these 5 solutions is measured, and plotted vs. their concentration resulting in a linear calibration curve of A vs C. Next we measure the azsbsorbance of the solution prepared from the commercial aspirin solution, and find its concentration by comparing its absorbance value on the calibration curve. SAMPLE CALCULATIN The following calculations are as an example only: in your report(() use your own mass of SA and ASA samples, and your own Absorbance data! 1. Standard solutions and Beer s law calibration curve Mass of SA: mg = g Molar mass of salicylic acid (SA), HC 6 H 4 CH = 138 g/mol (1) Moles SA = mass/molar mass = /138 = mol SA The SA is quantitatively transferred to a 100 ml volumetric flask, so: (2) Concentration of SA stock solution = mol/0.100l = /0.100 = mol/l (3) Concentration of SA dilution 5 (0.5 ml stock to 10 ml) = (0.5/10)x = 0.05x = mol SA/L This is (SA)5 Same for concentrations of solutions 4 1 with 0.4, 0.3, 0.2, 0.1 ml stock Solution 4: (0.4000/10)x = mol SA/L (SA)4 Solution 3: (0.3000/10)x = mol SA/L (SA)3 Solution 2: (0.2000/10)x = mol SA/L (SA)2 Solution 1: (0.1000/10)x = mol SA/L (SA)1 You have recorded the absorbances, A of the 5 solutions (with the FeCl 3 subtracted already by zeroing the instrument with the FeCl 3 solution in the cuvette). Record the absorbance values for solutions 1-5 in the table (below), and graph A vs concentration for these 5 standard solutions. Make your horizontal scale the concentration (e.g. from 0 to M with divisions of , and your vertical scale the absorbance, e.g. 0 to 1 with divisions of Analysis of unknown Aspirin tablet Note that now your initial mass is the mass of the aspirin (or ASA) tablet, which is not pure salicylic acid! Molar mass ASA = 180. Again, the numbers here are as an example only, use your own weight of the ASA tablet, and ASA UNKNWN Absorbance (1) Mass of aspirin tablet = g 66
3 (2) Absorbance (A) of ASA UNKNWN = (3) Concentration of ASA in unknown as determined from the calibration curve below: C ASA, unknown = (5.28 x 10-4 ) mol/l (see below) (4) Concentration of ASA UNKNWN : prepared by dilution ml to 10.0 ml, so the concentration in the STCK UNKNWN was 10/0.3, therefore C ASA stock = (10/0.3)xC ASA,unknown = 10x /0.3000= mol/l The aspirin tablet was dissolved and hydrolyzed and then diluted to 100 ml, therefore: moles ASA in 100 ml unknown = C stock unknown (mol/l)x0.100(l) = x0.100= mol ASA Mass of acetylsalicylate (ASA) = mol x molar mass = x180 = g ASA or 317 mg. % ASA in commercial tablet = g ASA/mass tablet = 0.317/0.354 = 89.5% ASA stated on the box is 325 mg. f course this is a fictitious example, we would expect most students to come within 10 mg (3%) of the 300 mg, possibly even better! Calibration Curve: Make graph of Absorbance A (absorbance units, y-axis) vs. concentration C (mol/l, x-axis) SA Solution Concentration, M From (3) above Absorbance (examples only) Absorbance ASA solution Concentration (from graph) For this example, the graph of A vs. M would be as follows: 67
4 The concentration of the ASA sample now can be read directly from the graph (the value of M at A = 0.802) If you use Excel to make the graph (the program used in this example), you can use the equation for the trendline (linear option) to find M from the equation. Safety precautions 1.0M NaH is caustic. Avoid contact with skin, wear gloves and safety glasses at all times. Be particularly careful when heating the ASA-NaH mixture on the hot plate, cover with watch glass to prevent spattering. Materials and chemicals UV/VIS spectrophotometer and polystyrene cuvettes, hot plate, 1 10 ml graduated cylinders, ml volumetric flask, 6 10 ml volumetric flasks, 1 ml graduated pipet or micropipette, ml Erlenmeyer flasks or 150 ml beakers, watch glass. Salicylic acid (reagent grade), 1.0 M NaH, 0.02M FeCl 3 (buffered to ph = 1.6 with HCl/KCl) Commercial Aspirin TM or ASA tablets for analysis (not to be used for your headache caused by this experiment!). Disposal The remaining NaH and Fe-salicylate solutions can be combined and neutralized before disposal. Procedure 1. peration of the spectrophotometer. Follow the instructions in the laboratory. Use FeCl 3 as the blank solution to zero the absorbance reading. 2. Preparation of the Fe-salicylate standard solutions and ASA unknown The preparation and measurements of the SA standards and ASA unknown can be done simultaneously. Salicylic Acid (SA) 1. Weigh approximately g SA directly into small dry beaker. Record the mass (g). Aspirin (ASA) 1. Weigh ASA tablet in beaker, record the mass, crush tablet. 2. Add 5 ml NaH. 3. Heat on hot plate until dissolved. Cool. 4. Transfer solution to 100 ml volumetric flask. Fill to the mark with distilled water. This is your stock SA solution 5. Prepare 5 standard solutions in 10.0 ml volumetric flasks: use micropipet to add 100, 200, 300, 400, and 500 μl stock SA into 10.0 ml volumetric flasks. Fill each flask to the mark with acidified FeCl 3 solution. Solutions will vary from light to dark violet colour. Mark the flasks 1 (100 μl) to 5 (500 μl) 6. Measure and record the absorbance of each solution at 530 nm, using the FeCl 3 solution as blank. 2. Add 5 ml NaH. 3. Heat on hot plate until dissolved (some fine non-active ingredients may still be visible). Cool. 4. Transfer solution to 100 ml volumetric flask. Fill to the mark with distilled water. This is your stock ASA solution 5. Prepare one ASA solution: use micropipet to add 300 μl ASA stock in 10.0 ml volumetric flask. Fill the flask to the mark with acidified FeCl 3 solution. The solution will have a medium dark violet colour. 6. Measure and record the absorbance at 530 nm 67
5 Experimental General Chemistry 1 Experiment 12: Analysis of a Commercial Aspirin or ASA Tablet Laboratory Data Sheet Name: Section: Brand name of commercial tablet: Calculations. 1. Standard solutions and Beer s law calibration curve (1) Mass of SA = g Molar mass of salicylic acid (SA), HC 6 H 4 CH = g/mol (2) Moles SA = mass/molar mass = mol SA The SA is hydrolyzed and quantitatively transferred to a 100 ml volumetric flask, so: (3) Concentration of SA stock solution = mol/0.100l = (2)/0.100 = mol/l (4) Concentration of SA solution 5 (0.5 ml stock to 10 ml) = (0.5/10)x(stock solution concentration) = mol/l A 5 = SA solution 4 (0.4 ml stock to 10 ml) = mol/l A 4 = SA solution 3 (0.3 ml stock to 10 ml) = mol/l A 3 = SA solution 2 (0.2 ml stock to 10 ml) = mol/l A 2 = SA solution 1 (0.1 ml stock to 10 ml) = mol/l A 1 = Enter these concentrations and absorbance in an Excel sheet and create a calibration curve. Attach this calibration curve with this report. 2. Analysis of unknown Aspirin tablet Note that now your initial mass is the mass of the aspirin (or ASA) tablet, which is not pure salicylic acid! (1) Mass of tablet = g Aspirin (2) Absorbance of ASA UNKNWN = (3) Concentration of ASA in unknown diluted solution as determined from the calibration curve, C ASA, unknown = mol/l (4) Concentration of ASA UNKNWN : prepared by dilution 0.3 ml to 10 ml, so the concentration in the STCK UNKNWN was 10/0.3, therefore 78
6 C ASA stock unknown = (10/0.3)xC ASA,unknown = mol/l The aspirin tablet was dissolved and hydrolyzed and then diluted to 100 ml, so moles ASA in unknown = Cstock unknown(mol/l)x0.100(l) = mol ASA Molar mass of ASA = 180 g/mol Mass of acetylsalicylate (ASA) = mol x molar mass = g ASA % ASA in commercial tablet = g ASA/mass tablet x 100% = % Make graph of Absorbance A (absorbance units) vs. concentration C (mol/l) You may want to enter concentrations and absorbances of solutions 1-5 in a table in Excel and graph the calibration curve in Excel! Compare your result to the mg/tablet noted on the label of the box! Conclusion and Comments: 78
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