Weigh 6 gs of salicylic acid and transfer it to a clean and dry 250 ml conical flask. In practice, I decided to perform the reaction in a single flask and use concentrated sulfuric acid to complete both steps at the same time. %PDF-1.2 %����
0000007424 00000 n If base-catalyzed hydrolysis is used, both acids will likely be deprotonated, and acid will need to be added to separate the salicylic acid (water insoluble) from the acetic acid (water soluble). Principle: Synthesis of aspirin from salicylic acid occurs by acetylation process in acidic medium. trailer << /Size 102 /Info 75 0 R /Root 77 0 R /Prev 190016 /ID[<2d4afc2c761e351bf9150f76bbe78a83><2d4afc2c761e351bf9150f76bbe78a83>] >> startxref 0 %%EOF 77 0 obj << /Type /Catalog /Pages 72 0 R >> endobj 100 0 obj << /S 298 /Filter /FlateDecode /Length 101 0 R >> stream Water is added to quench the reaction, destroy the excess acetic anhydride, and cause crude aspirin to crystallize.
0000004204 00000 n Vogel’s text book of Practical Organic Chemistry, Page No. Use: Our starting material is aspirin (acetylsalicylic acid). The final solution had a brown-orange tint which is the result of contamination since methyl salicylate should be a colorless oil. Add 8.5 ml acetic anhydride and 3-4 drops of concentrated sulphuric acid to the flask carefully and mix thoroughly. If I acquire additional glassware in the future, I will perform a distillation to purify the results. It reduces the risk of transient ischemic attacks in men. Salicylic acid interacts with acetic anhydride in presence of few drops of concentrated sulphuric acid to produce aspirin and a molecule of acetic acid. The impromptu reflux setup for the synthesis. 0000009817 00000 n After synthesis and analysis, it will be deter-mined if the crude and recrystallized samples were composed solely of either salicylic acid, acetylsalicylic acid, or a combination of both (3). The second step is a standard Fisher esterification. 0000008424 00000 n 0000006303 00000 n 136-137 °C.). (X) g of aspirin, % Yield = (Practical Yield)/(Theoretical Yield) × 100, Aspirin was synthesized and the yield was found to be ——— %. Synthesis of aspirin from salicylic acid using acetic anhydride. Heat for 10 min at 900C.! 0000001504 00000 n
76 0 obj << /Linearized 1 /O 78 /H [ 923 371 ] /L 191664 /E 11064 /N 22 /T 190026 >> endobj xref 76 26 0000000016 00000 n BACKGROUND Principle: Sulphanilamide can beprepared by taking acetanilide and treating it with excess of chlorosulphonic acid, which gives p-acetamidobenzenesulphonyl... BACKGROUND Principle: The reaction of conjugated dienes with the ethylenic or acetylenic compound to form a six member cyclic... BACKGROUND Principle: In the first step catalytic reduction of nitrobenzene is occurring forming N-phenylhydroxylamine in presence of zinc and... BACKGROUND Principle: Aromatic aldehyde condense with aliphatic or mixed aryl alkyl ketone in presence of aqueous alkali to form... BACKGROUND Principle: In the first step alcohol group of benzoin is oxidized to ketone group forming benzil in presence... BACKGROUND Principle: It is an associative type of reaction, like Dials-Alder reaction (pericyclic) but more a free radical reaction... BACKGROUND Principle: This is a method of condensation of an aryl 1,2-diamine with a 1,2-dicarbonyl compound by heating in... BACKGROUND Principle: Here a modified Friedel-crafts acylation reaction is occurring. 0000001294 00000 n Quenching with water will leave both acid products in their protonated form. Get a piece of filter paper that fits in the funnel, and place it flat in the funnel.
The reaction that is used for the synthesis is shown below. This removes the acetate from the aspirin. Clamp a side-arm flask to the ring stand, and connect a piece of rubber tubing to the side-arm. This reaction uses an excess of acetic anhydride, sulfuric acid as a catalyst, and heat to push the equilibrium toward the products. 0000001819 00000 n Cool down to room temperature and add water (crystallization solvent).! Water is added to quench the reaction, destroy the excess acetic anhydride, and cause crude aspirin to crystallize. In this experiment, you will prepare aspirin from salicylic acid and acetic anhydride using sulfuric acid as a catalyst.
Principle: Synthesis of aspirin from salicylic acid occurs by acetylation process in acidic medium. 0000004183 00000 n The proton is returned to the acid in the end so it is just a catalyst. Practical Organic Chemistry by Frederick George Mann and Bernard Charles Saunders Published by Longan Inc., Fourth Edition; Page No. Synthesis procedure! Substituting Lewis structures for molecular formulas in chemical reactions provides more information. 0000003024 00000 n This removes the acetate from the aspirin. Methyl salicylate is an organic ester responsible for the minty smell of wintergreen. Salicylic acid interacts with acetic anhydride in presence of few drops of concentrated sulphuric acid to produce aspirin and a molecule of acetic acid.
0000009838 00000 n Dry the synthesized product in an oven at 90 °C and calculate the yield. H���Mn�8��9�N����,� s��L�;�Ff�j��������]U���wv?�]���_?���ܯ�X��eO�U���_�}Br��|} ��v�[�ͭ��Ŧ���vCK�}]��)�tl��]���kW 0000008237 00000 n After refluxing, the resulting solution smelled quite strongly of wintergreen which indicates that the experiment was successful. ment (synthesis of aspirin masses, theoretical yield, percent yield and error, and TLC analysis). (The product is obtained as colourless crystals, yield 11 g and m.p. Connect the other end of the rubber tubing to an aspirator in the lab. Bacterial growth curve cultivation of anaerobs. H�b```���r�����ea�����&0t�%����m�����9�U����=y���MK+K/���vb�V�:�������f�[�W,�{oQ���.���`"�D5���� ��?ѱ��l�V�gW�����������}�]~���+������4 b��pC(�IA@&�����t��bYp`�2�p_(���豀�� �}�]�s�a�2��6,9>|�~a� - �W endstream endobj 101 0 obj 262 endobj 78 0 obj << /Type /Page /Parent 71 0 R /Resources 79 0 R /Contents [ 82 0 R 84 0 R 86 0 R 88 0 R 90 0 R 92 0 R 96 0 R 98 0 R ] /Rotate 90 /MediaBox [ 0 0 612 792 ] /CropBox [ 37 37 574 754 ] >> endobj 79 0 obj << /ProcSet [ /PDF /Text ] /Font << /TT2 94 0 R >> /ExtGState << /GS1 99 0 R >> /ColorSpace << /Cs5 80 0 R >> >> endobj 80 0 obj [ /CalRGB << /WhitePoint [ 0.9505 1 1.089 ] /Gamma [ 2.22221 2.22221 2.22221 ] /Matrix [ 0.4124 0.2126 0.0193 0.3576 0.71519 0.1192 0.1805 0.0722 0.9505 ] >> ] endobj 81 0 obj 1105 endobj 82 0 obj << /Filter /FlateDecode /Length 81 0 R >> stream 0000000923 00000 n ,l��{�n�����W0 ɾ�����,ߝ��FO��R���s���\��>�r�|WwWJrJ���g�Y��d���f�P}y�e�J���w,�]�ȼ�|;�U��[�:�O}����C{e�\[m��y���Jc��ƃc���&[�ا����/6�s�з�N��˹o���1o[��軱ҵ���N��߾��\V�slZ�]�d�^����Q��ׁ}��2*24I�l�T)��He�-�lȒb;�:�)�k��$�HDKr�C�*H�L��צH�K�Rc^jKr3����w��r�G���y�·ΰ���S��,�yt_}Wnp��b�q3b���<_�X����;����r�b�-h�R#�����(Ǘ꒔�;��ԗ|��r���. Here limiting reagent is salicylic acid; hence yield should be calculated from its amount taken. Warm the mixture on water bath at 60 degrees about 20 min with frequent stirring. This hydrolysis reaction can be accomplished through either acid or base catalysis. In the first step, water is used to break the ester bond. Synthesis of Aspirin By: Jon Torre.
(adsbygoogle = window.adsbygoogle || []).push({}); We Labmonk, some scientific researchers unite to design a platform for getting sources of different lab protocols and discuss various research related issues. Molecular formula of salicylic acid = C7H6O3, Molecular formula of acetylsalicylic acid (aspirin) = C9H8O4, Molecular weight of salicylic acid = 138 g/mole, Molecular weight of acetyl salicylic acid (aspirin) = 180 g/mole, 138 g of salicylic acid gives 180 g of aspirin, Therefore, 6 g of salicylic acid will give ? The reaction that is used for the synthesis is shown below.
1290. Purpose: To determine which of four catalysts yields the fastest reaction rate in the acetylation of salicylic acid (1) to form acetylsalicylic acid (2). It is recommended for arthritis and related arthritic conditions, myocardial infarction prophylaxis. The purpose of adding sulphuric acid (catalyst) is to aid and augent the process of detaching the acetate ion (CH3COO–) from acetic anhydride which ultimately gets associated with H+ ion from phenolic hydroxy group in salicylic acid to be eliminated as a mole of acetic acid.1. The synthesis is broken down into two parts: hydrolysis of the aspirin and esterification. Filter the crystals. The upper Erlenmeyer flask is filled with ice water to act as a reflux column. Put a Büchner funnel with a rubber stopper in the flask. This reaction will connect the salicylic acid to the methanol with concentrated sulfuric acid as the catalyst. Filter the crude product on a Buchner funnel using suction, wash with cold water. Induce crystallization.! This reaction uses an excess of acetic anhydride, sulfuric acid as a catalyst, and heat to push the equilibrium toward the products. The synthesis is broken down into two parts: hydrolysis of the aspirin and esterification. 0000001272 00000 n Allow the contents in the flask to cool and pour into 100 ml cold water in 250 ml beaker with constant Stirring. The acid serves to protonate one double bonded oxygen on the acetic anhydride this makes the reaction with the salicylic acid faster. 0000009008 00000 n Subscribe our Telegram channel for regular updates. 0000001841 00000 n 0000001639 00000 n
Recrystallize from boiling water along with small quantities of methylated spirit. 0000006281 00000 n Mix salicylic acid (solid) with acetic anhydride (liquid) and a catalytic amount of H2SO4.! This reaction is a series of electrophilic aromatic substitutions,... Production of alcohol from sugarcane Punit Tripathi, Vectors in Gene Cloning Plasmids Yogita Salgar, Bacterial growth curve cultivation of anaerobs Suman Kumar Mekap, Neuro Humoral Transmission Suman Kumar Mekap, Principles & Mechanism of Drug Action Suman Kumar Mekap. 0000003046 00000 n 0000010832 00000 n 0000005262 00000 n Aim: To prepare aspirin from salicylic acid.
In the first step, water is used to break the ester bond. 0000000868 00000 n 0000005241 00000 n The bottom beaker has a stir bar with the methanol salicylic acid, and sulfuric acid. The sulfuric acid came from hardware-store drain cleaner which contained some impurities and was also not as concentrated as I would have liked. Used for the relief of minor pains/aches and also mild to moderate pain. In this reaction, the –OH on the salicylic acid acts as the alcohol and the acetic anhydride acts like a carboxylic acid.
0000008987 00000 n
Our starting material is aspirin (acetylsalicylic acid). 110. 0000007403 00000 n
This procedure will use starting materials that can be found at a supermarket including aspirin, antifreeze, and drain cleaner.
This hydrolysis reaction can be accomplished through either acid or base catalysis. Click here to subscribe: Get great contents delivered straight to your inbox, just a click away, Subscribe Now, Synthesis of sulphanilamide from acetanilide, Synthesis of 9, 10-dihydroanthracene-9, 10-endo-α, β-succinic anhydride from anthracene, Synthesis of p-aminophenol from nitrobenzene, Synthesis of chalcone from benzaldehyde and acetophenone, Synthesis dihydroxytriptycene of from anthracene and p-benzoquinone, Synthesis of fluorescein from resorcinol and phthalic anhydride. Reactions: Procedure and Results: Aspirin Synthesis Tap water was heated on a steam bath in a 250 mL beaker.The temperature of an alcohol thermometer was equilibrated in a beaker of room temperature tap water.
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