Synthesis of Dye para Red from AnilineVia a Multi step sequence

Step 1:preparation of acetanilide

prepared by :Aras Jabar

Shaxawan Rahim & Tishko Mhamad

University of slemani

School of science

Chemistry department

Content

• Introduction

• Reactions

• Mechanism

• I.R spectrum

• NMR 1H Estimation

• Property

• Uses

• Toxicology

introduction

• Para Red is prepared by diazotisation of para-nitroaniline at ice-cold temperatures, followed by coupling with β-naphthol

• Chemical formula:C16H11N3O3

• Molar mass: 293.28gm/mol

• Appearance: Red solid

• Melting point: 248 to 252 °C

Reaction of synthesis Azo Dye para red

Nitric acid will react with NH2 to form a salt or it will oxidise the NH2 to NO2

Synthesis of acetanalide

Mechanism of acetylation reaction:

Mechanism of acetylation reaction by using acid catalyst:

I.R spectrum

IR for reactant(aniline) IR for product(Acetanilide)

NMR 1H Estimation

NMR 1H Estimation

Chemical and physical properties of acetanilide

Appearance: It is a white solid with a flaky appearance.Odor: This is an odorless compound.Solubility: Acetanilide is a little soluble in water. It is also

soluble in diethyl ether, ethanol, benzene and acetone.Molecular Weight: Its molecular weight is 135.17 g/mol.Melting Point: It has a melting point of 114.3 °C.Boiling Point: The boiling point for this substance is 304

°C.Density: The density of Acetanilide is 1.219 g/ cm3.Specific Gravity: It has a specific gravity of 1.214.

Uses

• It has application as an inhibitor in hydrogen peroxide.

• This compound is also used for stabilizing cellulose ester varnishes.

• It is applied in the intermediation in accelerator synthesis of rubber.

• This organic compound is used for manufacturing 4-acetamidobenzenesulfonyl chloride which is one of the key ingredients for producing sulfa drugs.

• This compound is used as a precursor for synthesizing pharmaceuticals like penicillin.

• It was experimentally used as a photographic developer in the 19th century.

Toxicology

Direct skin and eye contact will result in severe irritation. It can cause skin allergies and irritation of the respiratory tract. More serious effects may include blood abnormalities. This organic powder targets different human organs including blood, central nervous system, kidney and skin

procedure:

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