[PDF] [PDF] Synthesis of Aspirin

[PDF] 8-Synthesis of Aspirin

Aspirin can be made by reacting salicylic acid with acetic acid in the presence of an acid catalyst If acetic anhydride is used instead of acetic acid, the reaction is much faster and has a higher yield (since acetic anhydride is much more reactive than acetic acid) The reaction is shown on the following page

[PDF] ASPIRIN SYNTHESIS - University of Helsinki

Measure 5,5 ml (6g) acetic anhydride and add into the flask 5 Start stirring and add 4 drops of strong sulfuric acid Place condenser Page 3 Unit of Chemistry 

[PDF] Synthesis of Aspirin - Bellevue College

In this experiment you will synthesize aspirin from acetic anhydride and salicylic acid using phosphoric acid as a catalyst to speed up the reaction (it is not a 

[PDF] Synthesis of Aspirin

Reaction OH OH O salicylic acid O O O acetic anhydride O OH HO O O acetyl salicylic acid (aspirin) OH O acetic acid H2SO4 heat + + 

[PDF] Synthesis of Aspirin - Carbon

Figure 5: Acetylation of salicylic acid Risk Assessment Acetylsalicylate and salicylic acid are combustible and harmful if swallowed Acetic anhydride is corrosive, 

[PDF] Synthesis of Aspirin

7 sept 2010 · Acetylsalicylic acid is an acetic acid ester derivative of salicylic acid The earliest known uses of the drug can be traced back to the Greek 

[PDF] Aspirin synthesis for AS/A2 Level chemistry - University of Reading

3 acetic anhydride OH O OH salicylic acid OH O C H 3 + + acetic acid 2- hydroxybenzoic acid ethanoic anhydride ethanoic acid aspirin [ H + ] cat Reflux

[PDF] Experiment 11 Synthesis and Analysis of Aspirin - CSUN

Caution The preparation of aspirin involves the use of two very hazardous materials - concentrated sulfuric acid and acetic anhydride Proceed only if you have a 

[PDF] 5012 Synthesis of acetylsalicylic acid (aspirin) from salicylic acid

5012 Synthesis of acetylsalicylic acid (aspirin) from salicylic acid 12 8 g (11 9 mL, 125 mmol) acetic anhydride is filled in the reaction flask and three drops of

[PDF] acetic anhydride in dmf

[PDF] acetic anhydride ir spectrum

[PDF] acetic anhydride is obtained by the reaction of acetic acid and

[PDF] acetic anhydride ka formula

[PDF] acetic anhydride lewis structure

[PDF] acetic anhydride line formula

[PDF] acetic anhydride literature boiling point

[PDF] acetic anhydride literature melting point

[PDF] acetic anhydride melting boiling point

[PDF] acetic anhydride molecular formula

[PDF] acetic anhydride molecular melting point

[PDF] acetic anhydride molecular weight

[PDF] acetic anhydride msds fisher

[PDF] acetic anhydride msds fisher scientific

[PDF] acetic anhydride msds merck

Synthesis of Aspirin

SynthesisSynthesis

Purification

Purification

Characterization

Characterization

Aspirin: some background

Patented by Bayer in 1893Patented by Bayer in 1893

One of the oldest drugsOne of the oldest drugs

One of the most consumed drugs One of the most consumed drugs (Production in the US is 10 million (Production in the US is 10 million

Kg/year)

Kg/year)

Aspirin: Biological activity

Analgesic (painkiller)Analgesic (painkiller)

Antipyretic (fever reducer)Antipyretic (fever reducer) AntiAnti--inflammatory (inhibition of the synthesis of inflammatory (inhibition of the synthesis of prostaglandins prostaglandins)) Side effects: gastric irritation, bleedingSide effects: gastric irritation, bleeding

Apparition of new analgesics (Tylenol)

Apparition of new analgesics (Tylenol)

Aspirin: The Molecule

OHHOO acetyl salicylic acid (aspirin)

Organic background

Alcohols

AlcoholsAlcohols

Aliphatic alcoholsAliphatic alcohols

: Hydroxyl derivatives of saturated hydrocarbons: Hydroxyl derivatives of saturated hydrocarbons

EnolsEnols

: Hydroxyl derivatives of unsaturated hydrocarbons: Hydroxyl derivatives of unsaturated hydrocarbons ROH COH methanol ethanol OHR enol phenol

Organic background

Carboxylic acids

OHO formic acidacetic acid benzoic acid

Organic background

Esterification

OHO HO R carboxylic acidalcool esterH

This is an equilibrium!

Organic background

Esterification mechanism

OHO HO R carboxylic acidalcool ester OHOH OHOH

Organic background

Acidity: a review

BronstedBronsted--Lowry acidLowry acid

Substance that can donate a protonSubstance that can donate a proton

Lewis acidLewis acid

Substance that accepts loneSubstance that accepts lone--pair electronspair electrons

AH + HAH + H

O O ""AA

+ H+ H = [= [HH ][A][A ] / [] / [AH]AH] = = --Log KLog K

11Sulfuric acidSulfuric acid3.75

3.75Formic acidFormic acid4.19

4.19Benzoic acidBenzoic acid4.75

4.75Acetic acidAcetic acid14.0

14.0waterwaterpK

AcidAcid

Reaction

OHO salicylic acid OOO acetic anhydride OHHOO acetyl salicylic acid (aspirin) OHO acetic acidH heat++

Reaction mechanism

HOO HOO OHO HOO +-H

Safety

Consult MSDS for safety information on all the chemicals Consult MSDS for safety information on all the chemicals

you plan to use. you plan to use. MSDS are available from the 2507 MSDS are available from the 2507 webpagewebpage..

Synthesis procedure

Mix salicylic acid (solid) with acetic anhydride (liquid) and a Mix salicylic acid (solid) with acetic anhydride (liquid) and a catalytic catalytic

amount of H amount of H SOSO

Heat for 10 min at 90Heat for 10 min at 90

C.C.

Cool down to room temperature and add water (crystallization Cool down to room temperature and add water (crystallization

solvent). solvent).

Induce crystallization.Induce crystallization.

Filter the crystals.Filter the crystals.

Purification by Recrystallization

WHAT IS WHAT IS

RECRYSTALLIZATION?

RECRYSTALLIZATION?

Rapid and convenient way of Rapid and convenient way of purifying a solid organic purifying a solid organic compound compound The material to be purified is The material to be purified is dissolved in the hot appropriate dissolved in the hot appropriate solvent solvent As the solvent cools, the As the solvent cools, the solution become saturated with solution become saturated with respect to the substance, which respect to the substance, which then crystallize then crystallize Impurities stay in solutionImpurities stay in solution

METHODMETHOD

Choose the solvent Choose the solvent

Dissolve the soluteDissolve the solute

(Filter suspended solids)(Filter suspended solids)

Crystallize the soluteCrystallize the solute

Collect and wash the Collect and wash the

crystals crystals

Dry the crystalsDry the crystals

Assessment of purity:

Looking for properties

Physical propertiesPhysical properties!!

Physical appearancePhysical appearance

SolubilitySolubility

Melting pointMelting point

Infrared spectraInfrared spectra

Chemical propertiesChemical properties!!

Percent yieldPercent yield

Potentiometric Potentiometric

titration titration

Phenol testPhenol test

Assessment of purity:

Physical appearance!!

Physical state (solid? liquid? ..)Physical state (solid? liquid? ..)

ColorColor

OdorOdor

TextureTexture

Homogeneity in compositionHomogeneity in composition

Assessment of purity:

Solubility

In a test tube, transfer a small amount of your In a test tube, transfer a small amount of your product (end of a spatula)quotesdbs_dbs2.pdfusesText_4