StudentShare
Contact Us
Sign In / Sign Up for FREE
Search
Go to advanced search...
Free

Preparation of Acetyl Salicylic Acid (Aspirin) - Lab Report Example

Cite this document
Summary
Preparation of Acetyl Salicylic Acid (Aspirin) 13th December 2011 Introduction: Aspirin is the most widely used over the counter non-prescription drug in the United States. The drug is an effective analgesic that can reduce nerve pain, toothache and headache…
Download full paper File format: .doc, available for editing
GRAB THE BEST PAPER96.5% of users find it useful
Preparation of Acetyl Salicylic Acid (Aspirin)
Read Text Preview

Extract of sample "Preparation of Acetyl Salicylic Acid (Aspirin)"

?Preparation of Acetyl Salicylic Acid (Aspirin) 13th December Introduction: Aspirin is the most widely used over the counter non-prescription drug in the United States. The drug is an effective analgesic that can reduce nerve pain, toothache and headache. It also acts as an antipyretic drug where it reduces fever and an anti-inflammatory agent capable of reducing the swelling and redness associated with inflammation. Due to its ability to acts as an anticoagulant, aspirin is an effective agent in the prevention of strokes and heart attack. In the following experiment we embark to acquaint ourselves with a simple laboratory protocol for the synthesis of aspirin. This procedure will use acetic anhydride and sulfuric acid as the acid catalyst of the reaction. Objective: To illustrate the synthesis of the drug, aspirin and determine its purity by a chemical test Materials and methods: Synthesis of Aspirin A water- bath was prepared by filling half-way a 400mL beaker with water and the water heated to boiling point. 2.004g of salicylic acid was placed in a 125mL Erlenmeyer flask. Carefully 3mL of acetic anhydride was added to the flask and while swirling 3 drops of concentrated sulfuric acid were added. To avoid eye irritation and burns caused by acetic anhydride and sulfuric acid respectively, the chemicals were handled in the hood in gloves. The reagents were mixed and then the flask was placed in the boiling water-bath and heated for 15minutes. The setting of the practical is as shown in the diagram 1.1 below. This dissolved any solid while the solution was occasionally swirled. The Erlenmeyer flask was removed from the bath and left to cool to approximately the room temperature. The solution in the flask was then poured into a 150-mL beaker containing 20mL of ice water and mixed thoroughly before placing the beaker in an ice bath. The water destroyed any remnant of unreacted acetic anhydride and caused the insoluble aspirin to precipitate from the solution. The crystals were collected by filtering under suction with a Buchner funnel as shown in diagram 1.2 below. The side-arm of a 250mL filter flask was connected to a water aspirator with heavy wall vacuum rubber tubing. The Buchner funnel was inserted into the filter flask through a one-hole rubber stopper and a filter paper placed into the Buchner funnel making sure the paper covered all the holes. Finally the water was poured to the paper to wet it and then the water aspirator was turned on to a maximum water flow and the solution in the beaker poured into the funnel. The crystals were washed with two portions of cold water each 5mL and then followed by a one 10mL portion of cold ethanol. The suction of air was continued through the crystal for several minutes so as to dry them. The crystals were placed between several sheets of filter paper using a spatula and press-dried. A 50mL beaker was weighed before placing the crystals and reweighing the beaker. The weight and percentage yield of the crude aspirin was determined. Diagram 2: filtering using the Buchner funnel Procedure to determination of aspirin purity Three test tubes each 100 x 13 mm were labeled 1, 2, 3 and a few crystals of salicylic acid placed in the test tube-1 and in test tube-2 a small sample the newly synthesized aspirin was placed whereas for test tube-3 a small sample of crushed commercial was placed. In each of the test tubes, 5mL of distilled water was added and test tubes shaken to dissolve the crystals and a further 10 drops of 1% aqueous ferric chloride was also added to each test tube. Observation and comparisons were made from the three test tubes and recorded. Results and Discussion Theoretical yield 2.004g salicylic acid X Weight of 50-mL beaker = 39.21 Weight of the aspirin and the beaker = 40.69 Weight of aspirin = Weight of the aspirin and the beaker - Weight of 50-mL beaker 40.69 – 39.21 = 1.48 g Weight of crude aspirin = 1.48 g Percent yield = 56.70% Chemical test with ferric chloride Presence of unreacted salicylic acid can be detected with 1% ferric chloride which reacts with the phenol group in salicylic acid to give a violet color. This is the absolute test for a pure sample of aspirin which will not react with the ferric chloride. The aspirin from our experiment had a violet color as seen below in plate 1 indicating there was some salicylic acid which did not react. In plate 2 below is a spectrum obtained from our dried purified aspirin from the analyses carried in the Fourier Transform Infrared (FTIR) spectrophotometer. The functional groups are recognized from their various absorption peaks that are observed in the spectrum. A comparison was made between the spectrums generated from our re-crystallized sample and a known spectrum of aspirin in figure 1 below. The IR spectrum of Acetylsalicylic acid (aspirin) is as shown below Figure 1: Known spectrum of acetylsalicylic acid Absorption peaks for the functional groups present in aspirin C=C (aromatic), 1600 – 1400cm-1 C=O (ester), 1750 – 1730cm-1 C=O (carboxylic acid), 1725 – 1700cm-1 C-O (ester/carboxylic acid), 1300 – 1000 cm-1 O-H (carboxylic acids), 3300 – 2500 cm-1 The spectrum obtained from our experiment did not replicate the known absorption peaks for the various functional groups present in acetylsalicylic acid. This indicates that our sample failed the purity test and may be contaminated with unreacted reactants. Prelab questions 1. A person took aspirin because it is an antipyretic. What is the trying to accomplish Aspirin has anti –inflammatory potential where it reduces the swelling and redness symptoms which accompany inflammation. 2. Draw the structure of aspirin. Should this compound test positive with 1% ferric chloride solution? Explain your answer. No, aspirin is not a phenol and will not form the violet color in the presence of ferric compound. Usually a positive test with 1% ferric chloride indicates the presence of a phenol. 3 ArOH + FeCl3 3. Aspirin can irritate the stomach. What is usually done in the formulation of the drug that reduces this side effect? The active agent in aspirin, salicylic acid contains the phenolic group and carboxylic acid that results in the compound being harsh to the stomach lining. A formulation of the drug with ester acetylsalicylic acid is a lesser irritant and does not irritate the stomach. The ester hydrolyzed in the small intestine to salicylic acid which was absorbed into the bloodstream. In order to lower the irritability of this drug, the drug is coated with magnesium hydroxide, magnesium carbonate and Aluminium glycinate which are mixed into a formulation of aspirin. 4. What is the active ingredient that gives aspirin its therapeutic properties? Salicylic acid is the active agent that confers aspirin with the therapeutic properties. 5. What is the purpose of the concentrated sulfuric acid in the preparation of aspirin? Could some other acid be used? Sulfuric acid is the acid catalyst that speeds up the reaction of acetic anhydride with salicylic acid in the formation of aspirin though phosphoric acid can be used in place of sulfuric acid. 6. If in step no. 11 of the procedure, you failed to dry completely your aspirin preparation by omitting the drying between filter paper, what would happen to your percent yield? The percent yield is a ratio of the actual aspirin from the experiment verses the theoretical aspirin weight therefore omitting this step will led to a higher actual weight of aspirin hence giving a higher percent yield of aspirin which is false. 7. A student expected 8.4 g of acetylsalicylic acid, but obtained only 5.3g. What is the percentage yield? 5.3/8.4% Percentage yield = 63.10% 8. Tylenol also is an analgesic often taken by people allergic to aspirin. The active ingredient is acetaminophen . Would acetaminophen give a positive phenol test? Explain your answer. Does this compound contain the ester functional group? If not, what functional group is present? Yes, it has a phenol group in its structure and therefore will give a positive phenol test. This compound lacks an ester functional group and in its place is an ethanamide group. Conclusion The experimental results indicate that our aspirin was not in pure form as demonstrated by the ferric chloride chemical test and the absorption peaks of the various functional groups in the molecule as seen in the spectrum obtained from Fourier Transform Infrared spectrophotometer. In conclusion we were able to demonstrate a simple protocol for synthesizing aspirin and also demonstrated how the purity of this substance can be determined. Read More
Tags
Cite this document
  • APA
  • MLA
  • CHICAGO
(“Preparation of Acetyl Salicylic Acid (Aspirin) Lab Report”, n.d.)
Retrieved from https://studentshare.org/chemistry/1440083-preparation-of-acetyl-salicylic-acid-aspirin
(Preparation of Acetyl Salicylic Acid (Aspirin) Lab Report)
https://studentshare.org/chemistry/1440083-preparation-of-acetyl-salicylic-acid-aspirin.
“Preparation of Acetyl Salicylic Acid (Aspirin) Lab Report”, n.d. https://studentshare.org/chemistry/1440083-preparation-of-acetyl-salicylic-acid-aspirin.
  • Cited: 0 times

CHECK THESE SAMPLES OF Preparation of Acetyl Salicylic Acid (Aspirin)

Technical Definition and Description

This chemical is converted into salicylic acid once ingested by a person and is widely used to manufacture aspirin.... Aspirin undergoes esterification whereby salicylic acid is mixed with acetic anhydride.... This results in a chemical reaction which turns the hydroxyl group in salicylic acid into an ester (R-OH R-OCOCH3).... How aspirin Works Institution Introduction The basic concern in pharmacology is the causal-effect of different drugs....
3 Pages (750 words) Essay

Synthesis of Aspirin

072 mol) of salicylic acid, 3 ml (0.... The obtained Your Module Synthesis of Aspirin The purpose of the experiment is to synthesize aspirin form salicylic acid and acetic anhydride according to the following reaction: Figure 1: Synthesis of aspirin (Clayden, et al.... 072 mol) of salicylic acid, 3 ml (0.... The obtained product was tested for unreacted salicylic acid.... Aspirin product was added to the first test tube and salicylic acid was added in the second test tube....
1 Pages (250 words) Research Paper

Aspirin as One of the Major and Oldest Pain Killers

In 1838, Raffaele Piria [an Italian chemist] then working at the Sorbonne in Paris, split salicin into a sugar and an aromatic component (salicylaldehyde) and converted the latter, by hydrolysis and oxidation, to an acid of crystallized colorless needles, which he named salicylic acid (Bellis, 2012) acetyl salicylic acid is the chemical name of Aspirin.... Chemical Formula As mentioned earlier, acetyl salicylic acid is the chemical name of Aspirin.... acetyl salicylic acid is the chemical name of Aspirin and C9H8O4 is the chemical formula of aspirin....
7 Pages (1750 words) Assignment

Acetic acid from methanol

There exists none other huge volume chemical may claim the different feedstock and generation methods acetic acid can.... Methanol production can be achieved from various… Cativa system has been used largely to produce acetic acid from methanol through a number of processes that we shall discuss for the production of 250,000 t/year of acetic acid....
4 Pages (1000 words) Essay

Product Formulation Portfolio; Evaluation pro-forma 4 (PFPE4)

New formula (including new ingredients/replacement ingredients) formula evaluation Pyridine New Formula: C7H6O3 (salicylic acid) +C2OH3Cl (acetyl chloride) C9H8O4 (Aspirin) + HCl (hydrogen chloride)Old Ingredient New ingredient Why replacing the old one (is it better?... cts as a high quality acetylation agent due to its high reactivity and ability to produce irreversible reactions with weak acids such as salicylic acid....
1 Pages (250 words) Essay

Product Formulation Portfolio; Evaluation pro-forma 5 (PFPE5)

This Product Formulation Portfolio; Evaluation pro-forma 5 (PFPE5) Table 5 How new formula does defer from the old formula including amount for ingredients (include the full list of new formula) Old Formula: C7H6O3 (salicylic acid) + C4H6O3 (Acetic anhydride)  C9H8O4 (Aspirin) + C2H4O2 (Acetic acid)  Pyridine New Formula: C7H6O3 (salicylic acid) +C2OH3Cl (acetyl chloride) C9H8O4 (Aspirin) + HCl (hydrochloric acid)Old Ingredient Amount New ingredientAmount Justification of new ingredient amount is it suitable for this formulation (for example some chemicals can only be used certain concentrations in human consumption products, see MHRA, FDA, EMEA or any scientific resources) Acetic anhydride (CH3CO)2O)2ml for every 1gram of salicylic acid= (4ml for 2gms of salicylic acid)Acetyl Chloride (C2OH3Cl)1mlThe amount of the new ingredient used is justified because it is within the allowed concentrations of Acetyl Chloride in human consumption products as recommended by the US Food and Drug Administration (FDA) agency....
2 Pages (500 words) Essay

Chemistry and Society

nbsp; In the ancient time, spiraea and willow bark plant extract of which the active ingredient was salicylic acid had been used to ease pain, headaches and fevers.... In the year 1763, Edward Stone isolated the active element of aspirin when he discovered salicylic acid.... n the year 1859, von Gilm obtained acetylsalicylic acid through the reaction of acetyl chloride and salicylic acid (Watson, 2011).... The product was derived from Filipendula ulmaria species which had a less digestive upset as compared to the pure salicylic acid....
8 Pages (2000 words) Essay

Role of Chemistry in Pharmaceutical Industry

"Role of Chemistry in Pharmaceutical Industry" paper focuses on medicinal chemistry which is the application of techniques related to medical research to the synthesis of pharmaceuticals.... Today, scientists in this ground are equally anxious about the creation of new synthetic drug compounds.... hellip; Dr....
8 Pages (2000 words) Coursework
sponsored ads
We use cookies to create the best experience for you. Keep on browsing if you are OK with that, or find out how to manage cookies.
Contact Us