synthesis and spectral analysis of aspirin

Aspirin is a drug that is usually used to relieve minor aches and pain and other medical uses such as anti-inflammatory medication. Synthesis of Aspirin … In this experiment aspirin, also known as acetylsalicylic acid, was synthesized from salicylic acid and … The name aspirin was invented by the … Place approximately 200 mL of water into a 400 mL beaker and allow to warm to 70°C on a hot plate Further Analysis When was aspirin first synthesized, by whom, and for … Because neither of these values matches with those values on the acetic acid and salicylic acid IR spectra, it can be concluded that neither of the starting materials are present in the synthesized aspirin sample. A useful synthesis of acetylsalicylic acid was developed in 1893, patented in 1899, marketed under the trade name of “aspirin” by the Bayer Company in Germany. Salicylic acid was a white, chalky powder; acetic anhydride a clear, colorless liquid; and phosphoric acid a clear, yellow-tinted liquid. Spectral analysis plays an important role in the production of aspirin. Scheme 1: Synthesis of Aspirin O O H O O O O Na + Na + O H O H O O O O Na + MW = 152.15 MF = C 8 H 8 O 3 d = 1.18 g/ml pKa = 9.8 MW = 159.10 MF = C 7 H 4 O 3 Na 2 MW = 138.12 MF = C 7 H 6 O 3 MP = … The trial results of the synthesized aspirin titrations are listed below: By combining all three molecular weights, the average molecular weight was 1.7 x 102 g/mol. It is designed to be performed early rather than late; it starts from a naturally occurring material and requires two steps rather than one; and it utilizes FTIR spectroscopy to distinguish among oil of wintergreen starting material, salicylic acid intermediate, and aspirin product. The Synthesis of Aspirin 1. 2 0 obj A 50 mL burette was then washed with one 5 mL portion of NaOH, then filled to near the 0 mark of the burette with NaOH. All three synthesized aspirin titrations yielded a light pink color for 15 seconds, thus each trial was successful and used in calculations. Medicine Analysis – Synthesising Aspirin results After recrystallisation differences between the crude and purified aspirin were noted. The initial step of the experimental process was the synthesis of Aspirin, which required the reaction of salicylic acid, acetic anhydride, and phosphoric acid to produce aspirin and acetic acid. In the following experiment, Aspirin was synthesized and analyzed in a laboratory setting in order to recognize the chemical process behind a common drug like aspirin and to relate it to the conceptual study of organic chemistry. After aspirin synthesis was complete, the aspirin was analyzed using both IR and NMR spectrometers in order to determine the hydrogen atoms and organic functional groups present in the synthesized aspirin and to verify the overall identity of the aspirin. The molecular weight of commercial aspirin is 180.1574 g/mol, approximately 10 g/mol higher than that of the synthesized aspirin. Aspirin (acetylsalicylic acid) was synthesized by reacting salicylic acid and acetic anhydride with the aid of phosphoric acid as a catalyst. During IR spectroscopy, a pinhead sample of aspirin was placed on the diamond ATR plate of a Nicolet iS10 Infrared Spectrometer and the spectrum was printed. Most students know about aspirin, a pain-relieving compound, and they gain knowledge about the role of chemistry in real-life applications from its synthesis. CDCl3, used later for spectroscopy, is also a toxic chemical. The experiment differs in three ways from traditional aspirin synthesis experiments for general chemistry. After 15 minutes of maintained heat, the flask was removed from the water and 2 mL of DI water was added, producing an aromatic vapor. The proposed laboratory is a hybrid of both classic (synthesis of aspirin, TLC analysis, 1H, 13C NMR and IR spectra) and new (molecular modeling) chemistry elements. To begin the experiment, 2.00 g of salicylic acid (formula weight of 138.12 g/mol), 5.0 mL of acetic anhydride (density of 1.082 g/mL), and 5 drops of phosphoric acid were mixed in a 150mL Erlenmeyer flask, which was then placed in a beaker containing de-ionized (DI) water heated to 75°C on a hot plate. Utilizing 2.545 grams of salicylic acid and mixing it with 5mL of acetic anhydride, 6.051 grams of aspirin (acetylsalicylic acid) was obtained. Learn vocabulary, terms, and more with flashcards, games, and other study tools. The starting reading of NaOH was recorded. NMR was the first to be tested: a glass NMR tube was filled with the aspirin sample to a height of approximately 0.5 cm and 0.6 mL of CDCl3 was added in order to avoid large protein peaks. After aspirin synthesis was complete, the aspirin was analyzed using both IR and NMR spectrometers in order to determine the hydrogen atoms and organic functional groups present in the synthesized aspirin and to verify the overall identity of the aspirin. We suggest a simple and safe method for the synthesis of aspirin and its analysis … After the crystals were completely dry, the beaker was weighed a second time, including the crystals, in order to obtain the actual yield of synthesized aspirin: 2.1 g. This value was used, along with the theoretical yield value, to calculate the percent yield of the synthesized aspirin: 81%. The final mixture, a clear, colorless liquid, was stirred occasionally and the temperature of the water was monitored. When cold water was added, a by- product of acetic acid had formed … earlier paper described our ferrioxalate synthesis experiment (4). Do not lose this container or its contents, you will use them later. It is known from the NMR spectrum of acetone, which is a reference compound with only one type of hydrogen (that belonging to CH3), that the peak at 2 PPM in the acetic acid spectrum pertains to CH3 (table 2.3). The synthesis of aspirin … From these two analyses, it can be concluded that no reactants remain in the final product aspirin, and that the functional groups present in the synthesized aspirin NMR spectrum are CH3 and aromatic hydrocarbon (benzene). Start studying Experiment 34: Synthesis and Spectral Analysis of Aspirin. Overall, the purpose of this lab, to synthesis aspirin and prove its purity using organic functional groups, was accomplished successfully. Last week you made and purified aspirin. The moles of aspirin used was calculated and incorporated into a calculation of the average concentration of NaOH (mol/L) using the second and third trial amounts of NaOH. Looking again at the starting materials of the aspirin synthesis reaction, acetic acid and salicylic acid, each compound has one peak in the 1650 to 1850 cm-1 range on their IR spectra. Synthesis of Aspirin … 1) Calculate The Theoretical Yield Of Aspirin… The synthesized aspirin was also used in two different types of spectroscopy: NMR and IR. After the vapor dissipated, a second volume of DI water, 20 mL, was added. Determine The Purity Of Your Product By Measuring The Melting Point. Aspirin, also referred to as acetylsalicylic acid, is one of the most common synthetic medications found on the market today.1 Wh… Qualitative analysis of the Pure Aspirin Synthesized The pure Aspirin prepared was characterized qualitatively by physical constants, ferric chloride test, esterification and IR spectroscopic studies. Thus, the peak at 1679.70 cm-1 represents a carboxylic acid. This gas was acetic acid; an end product in the aspirin synthesis reaction, thus the NMR spectrum of acetic acid was analyzed. NSF CCLI Project Page 1 EXPERIMENT Aspirin: Synthesis and NMR Analysis Introduction: When salicylic acid reacts with acetic anhydride in the presence of an acid catalyst, acetylsalicylic acid, or aspirin, is … To do this, place an arbitrary amount of the substance to be … INTRODUCTION: Recall that last week you did the reaction shown to prepare aspirin… Acetic acid has a peak at 1704.69 cm-1 and salicylic acid has a peak at 1652.36 cm-1. Question: Organic Chemistry I: Synthesis Of Aspirin PURPOSE OF THE EXPERIMENT Synthesize Acetylsalicylic Acid. Next, NaOH was used to titrate commercial aspirin tablets – one tablet of aspirin, weighing 325 mg, was dissolved in methanol, and then 10 mL of DI water and 4 drops of phenolphthalein (indicator) were added. The aspirin is allowed to dry, weighed, and then the percent yield is … These trials’ pink solution were light, while the first trial’s pink solution was too dark, and resulted in a smaller concentration of NaOH. Excess anhydride reacts with water produced in esterification, which shifts the equilibrium in the forward direction and … Thus, the average concentration of NaOH was 5.0 x 10-2 mol/L. The two starting materials in the aspirin synthesis reaction were acetic anhydride and salicylic acid. This reaction is represented visually below: Figure 1.1 Aspirin synthesis: chemical reaction involving salicylic acid and acetic anhydride as reactants and aspirin and acetic acid as products. The two peaks in the 1650 to 1850 cm-1 range in the synthesized aspirin IR spectrum (figure 2.2) are at 1679.70 cm-1 and 1749.46 cm-1. stream In order to determine the purity of the aspirin, it must be characterized through various techniques based on an understanding of the energy of the system on the microscopic and atomic scale. • Take a small amount of the aspirin … The solution was then inserted into an Anasazi 60 MHz FT-Nuclear Magnetic Resonance Spectrometer and the spectrum was printed. The electronic spectra, percentage metal analysis … IR Spectral … The trial results of the commercial aspirin titrations are listed below: As mentioned in the experimental section, the first trial was not used in the final calculation of the average NaOH concentration. Acetic anhydride reacts with Salicylic acid to yield the ester (aspirin). The synthesis of this reaction obtained a percent yield of 98.19%. The table below lists IR standards from several IR spectra of functional group chemicals: There are several things to be taken away from the collected data in regards to the purity of the synthesized aspirin sample. Because the NMR spectrum of the synthesized aspirin sample does not have a peak at 11.0 PPM, it can be concluded that there is no leftover acetic acid in the final product. Because the range of peaks matches (table 2.3), with the aromatic hydrocarbon peaks, this range must represent the hydrogen atoms present in the benzene ring, and by process of elimination, the final peak at 9.1 PPM must be the remaining hydrogen in the alcohol in the structure of salicylic acid. Caution – acetic anhydride, salicylic acid, and phosphoric acid are all toxic chemicals and should not come into contact with the skin. I would like to acknowledge a few people who helped make this scientific paper better than it would have been: Kevin Braun, for supplying the materials of the experiment, assisting with the experiment, teaching NMR and IR spectroscopy, and reviewing the results of the experiment; *****, for assisting me with the interpretation of the NMR and IR spectra; ******, for assisting me with the IR worksheet assignment, experimental calculations, and proofreading; ********, for assisting me with the NMR worksheet assignment; and ******, for proofreading this paper. NMR spectra reflect the presence of hydrogen atoms, or protons, in a substance. Aspirin is an ester that has high molecular weight and it not soluble in water hence the solid can be separated by crystallization process. To finish the experiment, three titration trials were performed using the synthesized aspirin. H 2 SO 4 … The final product of synthesized aspirin contained no starting materials and its molecular weight was relatively close to that of pure aspirin, thus it was almost entirely pure. The remaining peak value from the synthesized aspirin is 1679.70 cm-1, which corresponds with values in both the ketone and carboxylic acid sections of table 2.4. %��������� This simple and effective form of laboratory testing provides valuable data that is required for maintaining the quality and purity of this widely used pharmaceutical. The flask was then scratched on the bottom and placed in an ice bath to encourage crystallization. The end point reading of NaOH was recorded. Each spectrometer yields further results regarding the purity of the aspirin. 0.3 g of aspirin was weighed by difference and dissolved in 5 mL of methanol in an Erlenmeyer flask for each trial. Day 1: Synthesis of Aspirin Lab Introduction: The Day 1 Aspirin Analysis PowerPoint Presentation (available for download) is an introduction to the lab experiment based on students having the lab … The Beer-Lambert law and two (FT-IR) permits continuous monitoring of the spectral chemometric approaches, partial least squares (PLS) baseline and simultaneous analysis of different compo- and … This paper describes the first of our organic synthesis experiments, the synthesis, purification, and qualitative spec-troscopic characterization of aspirin. In the reaction between acetic anhydride and water, a gas was released that gave off a smell similar to that of vinegar. Therefore, the second peak from acetic acid pertains to the hydrogen the carboxylic acid, at 11.0 PPM. Aspirin is an ester that has high molecular weight and it not soluble in water hence the solid can be separated by crystallization process. By matching the synthesized aspirin peak at 1749.46 cm-1 to the peak values in table 2.4, it is evident that this peak represents the ester in the structure of aspirin. This value, compared with the molecular weight of commercial aspirin, C9H8O4, will demonstrate the difference in purity. The proposed laboratory is a hybrid of both classic (synthesis of aspirin, TLC analysis, 1 H, 13 C NMR and IR spectra) and new (molecular modeling) chemistry elements. We suggest a simple and safe method for the synthesis … Add 5 mL (0.05 mole) of acetic anhydride, followed by 5 drops of conc. The table below lists NMR standards from several NMR spectra of functional group chemicals: NMR peak for functional groups (PPM range). It is possible to perform aspirin synthesis in a … Titration was then performed in three trials, each by adding NaOH to the mixture in the flask until the mixture turned light pink and maintained this color for 15 seconds. To summarize, both spectrometers give significant evidence suggesting the purity of the synthesized aspirin product. By using acetic acid’s spectrum as a reference for salicylic acid, it is known that the peak at 10.3 PPM is probably the hydrogen belonging to the carboxylic acid in the structure. However, looking at the structure of synthesized aspirin, the remaining component that has not been identified but is present in the structure is carboxylic acid. Although other testing methods are available, spectrophotometers offer the most versatile options in pharmaceutical testing and monitoring. This week you will use NMR, IR, and melting point to characterize your product. DI water and four drops of phenolphthalein were added, and the same process of titration was used. As shown in the above reaction, phosphoric acid, H3PO4 acts as a catalyst in the initial mixture of the reactants in order to speed up the reaction. The spectrum attained from IR spectroscopy is below: Figure 2.2 The IR spectrum of synthesized aspirin displays two peaks in the 1650 cm(^-1)  to 1850 cm(^-1) range at 1679.70  cm(^-1) and at 1749.46 cm(^-1). Many different laboratory techniques are used in the synthesis of Aspirin. Additionally, based on the IR spectra of the starting materials in the reaction, it is further conclusive that they are not present in the final product, and that the peaks on the IR spectrum of synthesized aspirin show functional groups ester and carboxylic acid in the final structure. Synthesis of Aspirin Lab Report The goal of this experiment was to synthesize aspirin. On the bottom and placed in a … synthesis of aspirin three synthesized aspirin titrations yielded light! Characterization of aspirin PURPOSE of this Lab, to synthesis aspirin and its... Acetic acid pertains to the hydrogen the carboxylic acid Lab, to synthesis and. 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