1. Acetylsalicylic Acid By: Jeraun Pogue Tierra Dixon Chemistry ll Mrs. Hall October 27,2008

2. Abstract The study’s main objective was to find the purity aspirin throughout six different experiments. In Standardization of a Pipette, the determine to calculate values that are not measurable with the equipment provided. The average amount of drops per one mL was 18.33;there is 0.33 mL for every one drop. Synthesis of Aspirin lab showed how to make aspirin. The lab Determination of Melting Point was used to get the melting point of each lab because melting point shows aspirin purity. Several sample compounds were placed into a Mel-Temp apparatus and melted a high temperatures. Relative Purity was also used to check chemical compounds color before and after they mixed with iron(III)chloride. Introduction to Digital Spectrophotometer lab familiarized groups with the functions of the Spectrophotometer 20-D machine. Spectrophotometric Analysis of Aspirin lab purpose was to determine the amount of aspirin in a commercial aspirin product. This lab may also be used to determine the purity of the aspirin produced in the Microscale Synthesis of Acetylsalicylic Acid lab. The study’s main objective was to find the purity aspirin throughout six different experiments. In Standardization of a Pipette, the determine to calculate values that are not measurable with the equipment provided. The average amount of drops per one mL was 18.33;there is 0.33 mL for every one drop. Synthesis of Aspirin lab showed how to make aspirin. The lab Determination of Melting Point was used to get the melting point of each lab because melting point shows aspirin purity. Several sample compounds were placed into a Mel-Temp apparatus and melted a high temperatures. Relative Purity was also used to check chemical compounds color before and after they mixed with iron(III)chloride. Introduction to Digital Spectrophotometer lab familiarized groups with the functions of the Spectrophotometer 20-D machine. Spectrophotometric Analysis of Aspirin lab purpose was to determine the amount of aspirin in a commercial aspirin product. This lab may also be used to determine the purity of the aspirin produced in the Microscale Synthesis of Acetylsalicylic Acid lab. The overall conclusion to the study found was the Chemistry II sample aspirin was not pure. The chemicals used to make the samples were not pure either. the Chemistry IA and Chemistry IB sample aspirin was not pure either. The chemicals used in the making the aspirin were originally pure but mixed together they came out in an impure form. The standardization of a pipette was a cause for an impure result. Relative purity showed the impure state. Melting points showed the chemicals used in the making of the aspirin were impure.

3. History of Aspirin Aspirin is used as a pain reliever and fever depressant. It was originally made from willow bark extract but today is made from salicylic acid (sodium calculate). Hippocrates was the first scientist to prescribe bark tree leaves as a pain reliever. A German scientist named Felix Hoffman that lived in Bayer Germany was the first person to stabilize acetylsalicylic acid when he used it to relieve his father’s rheumatism in 1897. Aspirin is used as a pain reliever and fever depressant. It was originally made from willow bark extract but today is made from salicylic acid (sodium calculate). Hippocrates was the first scientist to prescribe bark tree leaves as a pain reliever. A German scientist named Felix Hoffman that lived in Bayer Germany was the first person to stabilize acetylsalicylic acid when he used it to relieve his father’s rheumatism in 1897.

4. In 1828 the active ingredient in willow bark was isolated by Johann Buchner into a bitter tasting yellow needle- crystal form called salicin. Around 1920, aspirin was used to treat symptoms of pain related to rheumatism, lumbago, and neuralgia. As years past aspirin history expanded. In 1988, aspirin became used as a potential lifesaver; it was approved by the FDA to prevent mini- strokes in men and made standard therapy for previous strokes in men. In 1828 the active ingredient in willow bark was isolated by Johann Buchner into a bitter tasting yellow needle- crystal form called salicin. Around 1920, aspirin was used to treat symptoms of pain related to rheumatism, lumbago, and neuralgia. As years past aspirin history expanded. In 1988, aspirin became used as a potential lifesaver; it was approved by the FDA to prevent mini- strokes in men and made standard therapy for previous strokes in men. History of Aspirin

5. Standardization of a Pipette The purpose of this experiment is to determine to calculate values that are not measurable with the equipment provided. The purpose of this experiment is to determine to calculate values that are not measurable with the equipment provided.

6. Data Number of Drops per 1mL Trial 1 20 drops Trial 2 16 drops Trial 3 19 drops Formula for Average # of drops per 1mL = T 1 + T 2 + T 3 / 3 Average: __________18.33_____________ Formula for # of mL per drop: 1 drop x 1mL 1 # of drops 1 drop: __________0.33________mL

7. Results The results in this experiment were not precise due to a non-repeating pattern, such as, plus or minus one. The numbers came out to plus three then plus one. The accepted value for this experiment is 20. the results: 20, 16,19 came out to be 91.65% accurate with a random error of 8.35% because the results were above and below the accepted value. To improve the lab there should be a more accurate and precise counting of the droplets, and there should most likely be more test to make sure the results are as precise as possible. The results in this experiment were not precise due to a non-repeating pattern, such as, plus or minus one. The numbers came out to plus three then plus one. The accepted value for this experiment is 20. the results: 20, 16,19 came out to be 91.65% accurate with a random error of 8.35% because the results were above and below the accepted value. To improve the lab there should be a more accurate and precise counting of the droplets, and there should most likely be more test to make sure the results are as precise as possible.

8. Synthesis of Aspirin The purpose of this experiment is to make aspirin that is equivalent to half of an aspirin tablet. The purpose of this experiment is to make aspirin that is equivalent to half of an aspirin tablet.

9. Data Mass of salicylic acid used 0.914 g Mass of salicylic acid used 0.914 g Mass of filter paper and product 0.139 g Mass of filter paper and product 0.139 g Mass of filter paper 1.76 g Mass of filter paper 1.76 g Mass of product after drying 0.846 g Mass of product after drying 0.846 g

10. Results In synthesis of aspirin the conclusion formed was that the product had 21.16% error being 78.84% accurate. The measurements compared to the standard were precise but the results were not. The lab also had a theoretical yield of 37.3%. Reasons the results were not precise could be that some of the chemicals were still in the sample or when the sample was vacuum packed some of the sample could have been absorbed. Also the sample could not have been fully made. In synthesis of aspirin the conclusion formed was that the product had 21.16% error being 78.84% accurate. The measurements compared to the standard were precise but the results were not. The lab also had a theoretical yield of 37.3%. Reasons the results were not precise could be that some of the chemicals were still in the sample or when the sample was vacuum packed some of the sample could have been absorbed. Also the sample could not have been fully made.

11. Melting Point The purpose of this experiment is to determine the melting point of observed compounds because it shows the purity of a compound. The purpose of this experiment is to determine the melting point of observed compounds because it shows the purity of a compound.

12. Data for Melting Point Sample Compounds Trail 1 Observed Melting Point/ Range Trail 2 Observed Melting Point/ Range Trail 3 Observed Melting Point/ Range Average (of all 3 Trails) Observed Melting Point/ Range PossibleContaminant Acetylsalicylic Acid 140°C140°C140°C140°C 4% increase Unknown containment Salicylic Acid 168°C168°C168°C168°C 9% increase with an unknown contaminant Phosphoric Acid 42.35°C42.35°C42.35°C42.35°CStandard

13. Data for Melting Point cont. Acetic Anhydride -73°C-73°C-73°C-73°CStandard Water0°C0°C0°C0°CStandard Chemistry II Sample 16.6°C16.6°C16.6°C16.6°CStandard Chemistry I A Sample 124°C124°C124°C124°C Contaminated with acetylsalicylic acid, salicylic acid, phosphoric acid, and acetic anhydride Chemistry I B Sample 150°C150°C150°C150°C Contaminated with acetylsalicylic acid, salicylic acid, phosphoric acid, and acetic anhydride

14. Data for Melting Point cont. Enteric Aspirin 169°C169°C169°C169°C Contaminated with acetylsalicylic acid, salicylic acid, phosphoric acid, and acetic anhydride Acetic Acid 16.6°C16.6°C16.6°C16.6°C Contaminated with acetylsalicylic acid, salicylic acid, phosphoric acid, and acetic anhydride Assured Aspirin 150°C150°C150°C150°C Contaminated with acetylsalicylic acid, salicylic acid, phosphoric acid, and acetic anhydride

15. Results The conclusion for melting points was that acetylsalicylic acid had a temperature of 140*C this 4% increase had an unknown cause. Salicylic acid had temperature of 168*C this 9% had an unknown contaminant. Phosphoric acid was a standard because of its temperature 42.35*C. Acetic anhydride was a standard with a -73*C temperature. Water was a standard with a 0*C temperature. Chemistry II sample aspirin was a standard with a temperature f 16.6*C. Chemistry IA sample was Contaminated with acetylsalicylic acid, salicylic acid, phosphoric acid, and acetic anhydride. The conclusion for melting points was that acetylsalicylic acid had a temperature of 140*C this 4% increase had an unknown cause. Salicylic acid had temperature of 168*C this 9% had an unknown contaminant. Phosphoric acid was a standard because of its temperature 42.35*C. Acetic anhydride was a standard with a -73*C temperature. Water was a standard with a 0*C temperature. Chemistry II sample aspirin was a standard with a temperature f 16.6*C. Chemistry IA sample was Contaminated with acetylsalicylic acid, salicylic acid, phosphoric acid, and acetic anhydride.

16. Relative Purity The purpose of the this experiment is to check the purity of certain such as: salicylic acid, assured aspirin, enteric aspirin, Chemistry IA sample aspirin, Chemistry IB sample aspirin, Chemistry II sample aspirin, acetylsalicylic acid, acetic anhydride, acetic acid, phosphoric acid. The purpose of the this experiment is to check the purity of certain such as: salicylic acid, assured aspirin, enteric aspirin, Chemistry IA sample aspirin, Chemistry IB sample aspirin, Chemistry II sample aspirin, acetylsalicylic acid, acetic anhydride, acetic acid, phosphoric acid.

17. Data Chemical compound Color before FeCl3 Color after FeCl3 Salicylic acid WhitePurple Assured aspirin WhiteClear Enteric aspirin White Light pink Chemistry IA sample aspirin WhiteYellow Chemistry IB sample aspirin WhitePurple

18. Data cont. Chemistry II sample aspirin WhiteYellow Acetylsalicylic acid WhiteYellow Acetic anhydride ClearGold Acetic acid ClearOrange Phosphoric acid ClearClear

19. Results The conclusion based on the results of the mixture of each of the ten chemicals with Iron (III) chloride (FeCl3) was determined by each chemicals color after the mixture. If any of the chemicals are composed of six molecules of phenol combined with one Iron (III) ion should produce a positive (purple) test with Iron (III) chloride. Salicylic acid and chemistry IB sample aspirin were originally white, and then mixed with FeCl3 they turned purple meaning they produced a positive test. Salicylic acid would be a standard because it was tested at its pure state and the chemistry IB sample aspirin contains a high amount of salicylic acid. Chemistry IA sample aspirin, chemistry II sample aspirin, and acetylsalicylic acid were white and had yellow results meaning they were not positive. Acetylsalicylic acid would be used be used as a standard and it would be known that that it can be found in the chemistry IA sample aspirin and chemistry II sample aspirin. Acetic Anhydride was clear ending in a golden color being negative and a standard. Phosphoric acid was clear with clear results and it is also a standard meaning assured aspirin contains a large amount of phosphoric acid because of its clear results. All the chemicals that turned out to be a standard were that way because when they were at their purest form. Mistakes made would be adding to much FeCl3. Improvements to this lab would be to be more precise with the amount the amount of chemicals used and recorded.

20. Intro to Specs 20-D The purpose of the this experiment is to familiarize you with the basic technology and workings of the Spec- 20D- how to prepare a sample, which knob or button does what, and how to read and understand the display.

21. Data ColorRedOrangeYellowGreenBlueViolet Wavelength630590569500460400

22. Results With all the facts gathered from the experiment the conclusion made was that the spec-20 D is used to calculate absorbance, transmittance, and concentration of a certain wavelength. In the experiment it was able to be determined that certain colors were produced with certain wavelength. It was able to be known the function of each part of the machine. The lab could’ve went wrong if the controls were not working or if the students didn’t pay attention. Improvements to lab are unknown.

23. Specs To determine the amount of aspirin in a commercial aspirin product. This lab may also be used to determine the purity of the aspirin produced in the Microscale Synthesis of Acetylsalicylic Acid lab. To determine the amount of aspirin in a commercial aspirin product. This lab may also be used to determine the purity of the aspirin produced in the Microscale Synthesis of Acetylsalicylic Acid lab.

24. Data Chart for Absorbance Average Sample 2.52.01.51.00.5 salicylic acid 0.35100.31630.28000.17970.1113 assured aspirin 0.0470.0383330.040.0246670.009667 enteric aspirin 0.1073330.2013330.0873330.0743330.116 Chemistry IA 0.040.0126670.029-0.009333-0.018 Chemistry IB -0.020333-0.0966670.096-0.008-0.022333 Chemistry II 0.001-0.017333-0.021333-0.030333-0.036333 acetylsalicylic acid 0.0780.0683330.0623330.0826670.025667 acetic anhydride 0.0953330.087667-30.68033-0.028-0.071667 acetic acid 0.014667-0.0193330.0053330.0030.006 phosphoric acid 0.4613330.2733330.1823330.1333330.108333

25. Data Chart for Transmittance Average Sample 2.52.01.51.00.5 salicylic acid 44.666748.266752.866766.200077.4000 assured aspirin 84.1333386.93333 91.8 enteric aspirin 77.9333363.8666755.784.2666777.73333 Chemistry IA 9197.3333393.6102.1333104.4667 Chemistry IB 111.1333110.533380.4101.6667105.5 Chemistry II 100105.1333 107.2108.6667 acetylsalicylic acid 83.685.486.694.9333394.2 acetic anhydride 76.3333381.2104.9333105.9333116.1333 acetic acid 64.3403371.1323366.93965.0633366.33767 phosphoric acid 59.30568.3146767.12466.7816767.38133

26. Salicylic Acid

27. Assured Aspirin

28. Enteric Aspirin

29. Chemistry I A

30. Chemistry I B

31. Chemistry II

32. Acetylsalylic Acid

33. Acetic Anhydride

34. Acetic Acid

35. Phosphoric Acid

36. Absorbance Chart

37. Transmittance Values

38. Results In conclusion, none of the samples reached the absorbance standard. They all crossed each other but none reached the standard point. In transmittance, salicylic acid, acetic acid, phosphoric acid, and enteric acid all crossed the standard during the 0.5 line. The samples were not pure.

39. Conclusion The overall conclusion to the study found was the Chemistry II sample aspirin was not pure. The chemicals used to make the samples were not pure either. The Chemistry IA and Chemistry IB sample aspirin was not pure either. The chemicals used in the making the aspirin were originally pure but mixed together they came out in an impure form. The standardization of a pipette was a cause for an impure result. If the students were more precise with the count then when used in the making of acetylsalicylic acid the impurity would not have been thrown off. Relative purity showed the impure state. Reasons the relative purity possibly showed an impure result would be because the students put too much sample in the capillary tube to be tested so since the students were going off results written down instead of the first results from when the samples were made it would most likely have been pure. Melting points showed the chemicals used in the making of the aspirin were impure. Since the melting points of the chemicals of the chemical samples were not closely related to the standard they were impure because of contamination. The spec lab was the most obvious when it came to showing the impurity of the sample. The results showed in charts 2and 3 were nowhere near the standard.

40. References http://www2.volstate.edu/CHEM/1110/Labs/ Spectrophotomery.htm http://www2.volstate.edu/CHEM/1110/Labs/ Spectrophotomery.htm http://inventors.about.com/library/blaspirin.h tm http://inventors.about.com/library/blaspirin.h tm http://www.ic.sunysb.edu/class/chel34/lectu res/134pll.pdf http://www.ic.sunysb.edu/class/chel34/lectu res/134pll.pdf ©2000, 2003 by Science in Motion. All rights reserved  Darryl Rodgers and Carlos McCants