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    Preparation of Aspirin in Lab

    Uploaded by

    Muhammad Sanan Javed
    The document describes the synthesis of aspirin (acetylsalicylic acid) from salicylic acid and acetic anhydride. It provides the step-by-step procedure for the synthesis including heating the reactants in the presence of sulfuric acid, cooling to allow crystallization, filtering and washing the product. It also describes tests to check for the presence of unreacted starting materials and calculations for determining the theoretical and percent yield of the reaction.

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    Preparation of Aspirin in Lab

    Uploaded by

    Muhammad Sanan Javed
    39 views5 pages
    The document describes the synthesis of aspirin (acetylsalicylic acid) from salicylic acid and acetic anhydride. It provides the step-by-step procedure for the synthesis including heating the reactants in the presence of sulfuric acid, cooling to allow crystallization, filtering and washing the product. It also describes tests to check for the presence of unreacted starting materials and calculations for determining the theoretical and percent yield of the reaction.

    Original Description:

    How to prepare aspirin

    Original Title

    aspirin

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    The document describes the synthesis of aspirin (acetylsalicylic acid) from salicylic acid and acetic anhydride. It provides the step-by-step procedure for the synthesis including heating the reactants in the presence of sulfuric acid, cooling to allow crystallization, filtering and washing the product. It also describes tests to check for the presence of unreacted starting materials and calculations for determining the theoretical and percent yield of the reaction.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    39 views5 pages

    Preparation of Aspirin in Lab

    Uploaded by

    Muhammad Sanan Javed
    The document describes the synthesis of aspirin (acetylsalicylic acid) from salicylic acid and acetic anhydride. It provides the step-by-step procedure for the synthesis including heating the reactants in the presence of sulfuric acid, cooling to allow crystallization, filtering and washing the product. It also describes tests to check for the presence of unreacted starting materials and calculations for determining the theoretical and percent yield of the reaction.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 5

    Preparation of Aspirin in Lab

    Many compounds obtained from nature have been used to cure ills or to produce
    an effect in humans. These natural products have been obtained from plants,
    minerals, and animals. In addition, various transformations of these and other
    compounds have led to even more medically useful compounds. Analgesics are
    compounds used to reduce pain, antipyretics are compounds used to reduce fever.
    One popular drug that does both is aspirin. The Merck Index, which is an
    encyclopedia of chemicals, drugs and biologicals, lists the following information
    under aspirin: acetylsalicylic acid; monoclinic tablets or needle-like crystals; mp
    135 °C (rapid heating); is odorless, but in moist air it is gradually hydrolyzed into
    salicylic and acetic acids;.

    synthesis of aspirin by reacting excess acetic anhydride with a determined mass of 2-


    hydroxybenzoic acid which is also known as salicylic acid in the presence of an acid catalyst
    which was concentrated sulfuric acid. Aspirin belongs to the family of organic compounds
    known as esters and is an acetyl derivative of salicylic acid. The esterification process involves
    the reaction of a carboxyl group with a phenol group and the reaction is reversible.

    Aspirin is one of the most inexpensive, yet safest pain-killers available in today’s market, with
    approximately 35,000 metric tons of consumption annually. It has analgesic, antipyretic and anti-
    inflammatory properties which could be used to treat fevers, minor pains, discomfort and
    lowering of inflammation in the body. The salicylic acid extracted straight from these plants
    were unfortunately too harsh for oral ingestion.

    SYNTHESIS OF ASPIRIN (acetylsalicylic acid)


    Mechanism of aspirin synthesis
    Procedure

    1. Place 1.5 g – 2g of salicylic acid in a 125-mL Erlenmeyer flask.


    2. Add 5 mL (0.05 mole) of acetic anhydride, followed by 5 drops of conc.
    H2SO4 (use a dropper, H2SO4 is highly corrosive) and swirl the flask gently
    until the salicylic acid dissolves.
    3. Heat the flask gently on the steam bath for at least 10 minutes.
    4. Allow the flask to cool to room temperature. If acetylsalicylic acid does not
    begin to crystallize out, scratch the walls of the flask with a glass rod. Cool
    the mixture slightly in an ice bath until crystallization is completed. The
    product will appear as a solid mass when crystallization is completed.
    5. Add 50 mL or 100ml of water and cool the mixture in an ice bath. Do not
    add the water until crystal formation is complete.
    6. Vacuum filter the product using a Buchner funnel. You can use some of the
    filtrate to rinse the Erlenmeyer flask if necessary.
    7. Rinse the crystals several times with small portions (5 mL) of cold water and
    air dry the crystals on a Buchner funnel by suction until the crystals appear
    to be free of solvent. Test this crude product for the presence of unreacted
    salicylic acid using the ferric chloride test. Record the weight of the crude
    solid which probably contains water.
    8. Stir the crude solid with 25 mL of a saturated aqueous sodium bicarbonate
    solution in a 150 mL beaker until all signs of reaction have ceased (evolution
    of CO2 ceases).
    9. Filter the solution through a Buchner funnel to remove any insoluble
    impurities or polymers that may have been formed. Wash the beaker and the
    funnel with 5 to 10 mL of water.
    10. Carefully pour the filtrate with stirring, a small amount at a time, into an ice
    cold HCl solution (ca 3.5 mL of conc. HCl in 10 mL of water) in a 150-mL
    beaker and cool the mixture in an ice bath. Make sure that the resulting
    solution is acidic (blue litmus paper) and that the aspirin has completely
    precipitated out.
    11. Filter the solid by suction and wash the crystals with 5 mL of cold water
    each. Remove all the liquid from the crystals by pressing with a clean
    stopper or cork. Air dry the crystals and transfer them to a watch glass to
    dry. Test a small amount of the product for the presence of unreacted
    salicylic acid using the ferric chloride solution.
    12. When the product is completely dry, weigh the product, determine its
    melting point (lit mp 135-136 °C) and calculate the percentage yield.

    FERRIC CHLORIDE TEST FOR SALICYLIC ACID

    Add 10 drops of aqueous 1% ferric chloride solution to a test tube containing a few
    crystals of the compound to be tested dissolved in 5 mL water and note the color.
    Do this test with 1.phenol, 2. salicylic acid, and 3. your crude product. Formation
    of an iron-phenol complex with Fe(lll) gives a definite color ranging from red to
    violet, depending upon the particular phenol present.

    Calculations: a) Calculate the Mr (relative molecular mass) of the substances.

    Ar : C = 12, H = 1, O = 16 So,

    Mr : • Salicylic acid = C7O3H6 = (12x7)+(16x3)+(6x1) = 138 g

    • Ethanoic Anhydride = C4O3H6 = (12x4)+(16x3)+(6x1) = 102 g

    • Aspirin = C9O4H8 = (12x9)+(16x4)+(8x1) =180 g

    b) Change the grams to moles for salicylic acid to calculate moles


    Salicylic acid= 1.5 g. 1.5 ÷ 138 = 0.01086 moles

    c) Calculate the mass of Ethanoic Anhydride

    The density is 1.082 g/cm3 1.082 x 5 = 5.41 g 5.41/102= 0.0442moles

    d) Which chemical compound is the Limiting Reagent:

    1 mole: 1 mole ratio

    The same values 0.0186: 0.0442

    The lowest value is the Limiting Reagent which is Salicylic Acid

    e) Calculate the Theoretical yield mass in grams for Aspirin Salicylic Acid mole
    value multiply by Aspirin molecular mass 0.01086 x 180 = 1.9548 g

    f) Calculate the Percent Yield.

    %Yield = Actual Yield of Aspirin / (g) Theoretical Yield of Aspirin (g) × 100%

    The actual mass obtained of Aspirin is 0.686 g

    so, the percent yield = 0.686 ÷ 1.9548 × 100% = 35.09%

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