Apply knowledge in context and assess learning with questions exploring natural polymers, including starch and amino acids. The theoretical yield of 5.22 g acetylsalicylic acid was stoichiometrically determined using the starting mass of salicylic acid (4.0 g) because it was the limiting reactant. In this laboratory exercise, you can prepare aspirin (acetylsalicylic acid) from salicylic acid and acetic anhydride using the following reaction: salicylic acid (C7H6O3) + acetic anhydride (C4H6O3) → acetylsalicylic acid (C9H8O4) + acetic acid (C2H4O2) First, gather the chemicals and equipment used to synthesize the aspirin. equation). Measure out all the substance individually. H 2 SO 4 ( use a dropper, H 2 SO 4 is highly corrosive ) and swirl the flask gently until the salicylic acid dissolves. By using this site, you agree to its use of cookies. Synthesis of Aspirin INTRODUCTION Aspirin is one of the milder and least expensive pain relievers available. If the experiment was to be done again the following recommendations would be given: ? ? It is used to treat pain, reduce fever, and to decrease the aggregation of platelets, such as to decrease blood clotting. A balanced equation for the synthesis of Aspirin from Salicylic Acid and Acetic Anhydride is the following: Salicylic acid + acetic anhydride –> Acetylsalicylic acid + Acetic acid (C7H6O3) + (C4H6O3) –> (C9H8O4) + (C2H4O2) 0. Then it will be discussed as to why the yield produced are the same or different and also why the melting point are the same or different. The BF3ŸOEt2, due to its toxicity, was added by the TA. salicylic acid (salicylate ion) to give a purple solution. Wait and observe a little longer until all of the aspirin has melted. Starting Melting point temperature of aspirin: 110. Why are the reasons for this yield? The report also mentions how there are factors in the production of aspirin and how they affect the yield and purity. The intensity of the purple color corresponds with the concentration of phenol functional groups present. This was done by providing a safety glass barrier that was placed in front of the fume cupboard to keep a safe distance. However when 70°C was reached and the heater was turned off, it was observed that the temperature on the thermometer had risen around 10°C more after this point. Add 10 mL of ethanol and gently warm the mixture on a hot plate to dissolve. °C ? The melting point of pure acetylsalicylic acid is 135 ˚C1. 20g of aspirin was produced. This procedure was repeated using pyridine (5 drops), boron trifluoride etherate (5 drops), then concentrated sulfuric acid (5 drops) as the catalyst. Balance: The balance used to calculate the mass of the wet and dry product along with the beaker was considerably outdated. Available from: http://chemistry. Filtration ? 80 ml acetic anhydride ? Transfer 20 drops of this aspirin-ethanol solution into tube A. Also bearing in mind it is very impossible to get 100% yield it is still possible to obtain a greater amount of yield. For example Acetic Anhydride could be harmful is inhaled in large amounts. "You must agree to out terms of services and privacy policy", Don't use plagiarized sources. However from the experiment that was been done it was concluded that 56. Enthalpies of other side reactions, such as the polymerization of salicylic acid may have also contributed to the temperature change, corrupting the data. Beaker 1 +/- 100 ml ? 3623 mol + 0. Assess learning with questions about the reactions of alkanes and alcohols. 5ml) ? Acids, unlike bases, catalyze the reaction at multiple steps because the acid’s proton is transferred around the molecule. com/od/demonstrationsexperiments/ss/aspirin_5. RP 10: Preparation of: a pure organic solid and test of its purity, a pure organic liquid. Principle: Synthesis of aspirin from salicylic acid occurs by acetylation process in acidic medium. Place the contents into a beaker with around 750 ml of cool water. In this lab, for recrystallization, the solution was allowed to cool to room temperature very slowly, but was then plunged rapidly into ice water. Using a round-bottomed Quick-fit flask mix the measured Salicylic acid and the acetic anhydride together. ����zV��e �,r��}�CCM9���nP�"���ST>4 about. This way an idea of the safety conditions and the handling of chemicals can be considered. This figure mainly reflects purchase of 16,000 tons of aspirin tablets or 80 million tablets a year. Filter paper ? The solubility of aspirin in water increases as the temperature increases. The reason for this is due to an increase in kinetic energy. What are the major differences between your experimental process and the process most widely used in industry? Salicylic acid, whose name comes from Salix, the willow family of plants, was derived fromwillow bark extracts. Aspirin Synthesis    Tap water was heated on a steam bath in a 250 mL beaker. Sodium acetate (0.20 g) was added to one test tube. Once aspirin is synthesized, it needs to be purified, and an estimation of its purity should be performed. The definition of rate of reaction is the change in concentration of products over the change in time (∆[P] / ∆t). ? Iron (III) chloride can be coordinated and then reduced by deprotonated phenol. The sample should have been slowly cooled to 0 ˚C by placing it in a refrigerator and slowly lowering the temperature. Although this sounds far fetched it was still a flaw in the experiment. This proves that the aspirin that had been made in the experiment was not 100% pure and contained some impurities. As soon as this occurs note the temperature. This could have affected the purity of the Aspirin formed at the end. Calculate the yield. After a minute, remove the flask from the water bath and add 20 mL of distilled water. Soc. Place a small amount of yield around 0. [i] ? Overall this shows that the experiment was a success as a large amount of aspirin was produced, however these results also showed that there was major errors or inefficiencies in the experiment. What is the actual yield produced in the experiment compared to the theoretical yield? App. ? All you need to do is fill out a short form and submit an order. How to Make Aspirin – Acetylsalicylic Acid. This second step rapidly precipitated large crystals, likely leading to high impurity. This site uses cookies from Google and other third parties to deliver its services, to personalise adverts and to analyse traffic. There were many reasons to this. 01 g of aspirin per gram of water. Add 5 mL (0.05 mole) of acetic anhydride, followed by 5 drops of conc. To most directly measure rate, the concentration of a product should be measured periodically over time. your own paper. 2, 291-300, 2 R.E. 5 +/- ml ? A small amount of a strong acid is used as a catalyst that speeds up the reaction. 5) ml or of concentrated sulphuric acid. The flask was heated for 5 minutes over a steam bath to hydrolyze excess acetic anhydride then rapidly cooled in an ice bath. 56. 66, 2116 – 20. Salicylic acid and acetic anhydride have heats of solvation in water, so aqueous catalyst would change the reaction’s rate of temperature change relative to the non-aqueous catalyst even if the catalysts were equally effective. 22g of aspirin produced. Figure 2. take longer time in completing the experiment ? The personal yield was nearly zero, likely due to side reactions. Experimental Plan: An experiment will take place producing aspirin (Acetylsalicylic acid) from Salicylic acid and acetic anhydride. 2%. From analysing the original data values it is possible to calculate the theoretical yield using moles and masses. In this, experiment, phosphoric acid will be used as the catalyst. The procedure was repeated using one drop of molecular iodine solution in place of iron (III) chloride solution. This is a possible source of error that would lead to a less consistent time and wider data spread/greater standard deviation. Synthesis of Aspirin INTRODUCTION Aspirin is one of the milder and least expensive pain relievers available. 3623 mol + 0. 4 0 obj Melting point apparatus checker ? This might explain the large data spread. com/lifescience/phar/ACETYLSALICYLIC%20ACID. Therefore moles acetylsalicylic acid (aspirin) = 0. According to the “Handbook of Chemistry and Physics” the melting point of aspirin is 135°C. 50g of salicylic acid ? You can get your custom paper from Bases catalyze the reaction by  deprotonating the carboxyl group on salicylic acid (or the phenol group in the minor pathway), activating the nucleophile. [ii] In boiling water, 1. use better apparatus that are 100% efficient ? This will be done by subtracting the mass of the dry weight by the mass of the beaker. The factors that contributed to the inaccuracy of the experiment are the following: Reflux: The apparatus used in the experiment were quite old. 4. The general mechanism for catalysation by a base, like the acetate ion or pyridine, is shown in Figure 2. Festival of Sacrifice: The Past and Present of the Islamic Holiday of Eid al-Adha. 3623 mol As we can see above the mole ratio is 1:1:1:1:1. As a result the action of condensing was not 100% efficient. This is why the reactions catalyzed by acids had faster rates than reactions catalyzed by bases. Using these ideas it will be deduced as how the temperature of water affects the solubility of the Aspirin. Instead of the normal procedural method, the measured amounts of each substance were given. ? (Do not allow temperature to exceed 70 degrees). This figure mainly reflects purchase of 16,000 tons of aspirin tablets or 80 million tablets a year. As the solution cools, crystals of aspirin will appear. Only the salicylate ion complexes to iron(III). However compared to the theoretical yield it is evident that there was a great loss of aspirin that should have been formed. The original data and obtained data are revealed, and then they are discussed with thorough interpretations along with conclusions made, as well as recommendations. htm [Accessed 05 MAR 2009] [iv] How products are made: Volume 1.

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