SYNTHESIS OF AZO DYE FROM 2, 4-DINITROANILINE, 3-AMINO-5-METHYLPYRAZOLE AND BYROSCARPUS COCCINEUS


SYNTHESIS OF AZO DYE FROM 2, 4-DINITROANILINE, 3-AMINO-5-METHYL PYRAZOLE AND BYROSCARPUS COCCINEUS  

ABSTRACT

Azo dye was synthesized from 2,4,-dinitroaniline which was diazotized and coupled with 3-amino-5-methylpyrazole. The product obtained was in turn diazotized under acidic medium and coupled with Byroscarpus coccineus to give a disazo dye. The dye produced was characterized using UV-visible and IR spectrophotometer. The UV-visible result showed that the dye gave an absorption band at 362nm and absorbance of 0.725. The major functional groups obtained from the IR spectrum of the dye were CH3, OH, NO2, C-N and C=O respectively.

TABLE OF CONTENTS

Cover Page    i

Certification    ii

Declaration    iii

Dedication    iv

Acknowledgement    v

Table of Contents    vi

Abstract    viii

CHAPTER ONE:  INTRODUCTION    1

1.1    Background of Study    1

1.2    Objectives of the Study    2

1.3    Colour  and its Chemical Constitution    3

1.4    Relevance of Study    4

1.5    Limitation of Study    4

1.6    Problems Encountered during the Study    4

CHAPTER TWO: LITERATURE REVIEW    5

2.1    Historical Development of Synthetic Dyes    7

2.2    Classification of Dyes    9

2.3    Properties of Azo Dyes    13

2.4    Synthesis of Azo Dyes    14

2.4.1    Diazotization    14

2.4.2    Azo coupling    16

2.5    Uses of Azo Dyes    18

CHAPTER THREE: MATERIALS AND METHOD    19

3.1    Apparatus    19

3.2    Instruments    19

3.3    Materials    20

3.4    Methods    20

3.4.1    Extraction of Byroscarpus coccineus    20

3.4.2    Synthesis of azo dye    21

3.4.3    Diazotization and coupling procedures    21

CHAPTER FOUR: RESULTS AND DISCUSSION    25

4.1    Results    25

4.2    Discussion on UV-visible Spectrum    25

4.3    IR Spectral Discussion    26

CHAPTER FIVE: CONCLUSION AND RECOMMENDATION    27

3.5    Conclusion    27

3.6    Recommendation    27

References    28

CHAPTER ONE:

INTRODUCTION

1.1            Background of Study: SYNTHESIS OF AZO DYE FROM 2, 4-DINITROANILINE, 3-AMINO-5-METHYLPYRAZOLE AND BYROSCARPUS COCCINEUS

 Azo compounds are a class of chemical compounds that are continuously receiving attention in scientific research (Kirkan, 2008; Otutu, 2013, Seferoglu, 2009). Azo dyes contain one or more azo groups (-N =N-) which are linked to SP2 hybridized carbon atoms, based on the number of such groups (Zollinger, 1991). The dyes known as monoazo dyes have only one (-N = N -) group while diazo and triazo dyes contain two and three (-N = N -) group, respectively.

The azo groups are generally connected to benzene and naphthalene rings, but can also be attached to aromatic heterocycles or enolizable aliphatic groups (Hunger, 2000).Synthetic dye manufacturing started in 1856, when the English chemist W.H. Perkin, in an attempt to synthetize quinine, obtained instead a bluish substance with excellent dyeing properties that later became known as aniline purple, Tyrian purple or mauveine. Henry Perkins 18 years old patented his invention and set up a production line. This concept of research and development was soon to be followed by others and new dyes began to appear on the market, a process that was strongly stimulated by Kekules discovery of the molecular structure of benzene in 1865. In the beginning of the 20th century, synthetic dyestuffs had almost completely supplanted natural dyes (Welham, 2001). The synthesis of most azo dyes involves diazotization of a primary aromatic amine, followed by coupling with one or more nucleophilic aromatic compound such as an aryl amine or a phenol (McCorthy, 1997). Azo dyes are the most important class of industrial dyes, both in number and amount. In addition, azo dyes have found wide application in dyeing wool, polyamide fiber, semi conductivity textile and food industries (Bluss, 1995). In the present study a new azo compounds was prepared and Identification by IR, UV–Visible spectroscopy was carried out.

1.2            Objectives of the Study: SYNTHESIS OF AZO DYE FROM 2, 4-DINITROANILINE, 3-AMINO-5-METHYLPYRAZOLE AND BYROSCARPUS COCCINEUS

The objectives of work are to

synthesize azo dyes from 2,4,­­- dinitroaniline and 3­- amino ­-5- methylpyrazole characterize the dyes using Infra-red spectroscopy and UV­­­­­­­­­­­­- visible spectroscopy

1.3            Colour and it's Chemical Constitution

After the synthesis of mauviene in 1856 by Henry Perkins, little was known of the chemistry of dyes and the constitution of mauviene was not established. However, following kekul’s proposal concerning the structure of benzene in 1865 which lead to theories concerning the influence of organic structures on the colour of molecules began. Graebe and Lieberman in 1867 observed that organic dyes know then were unsaturated compounds and that this unsaturation is destroyed by reducing agent which causes them to decolourise.

Witt 1876 put forward a theory that the colour of a substance is mainly due to the presence of an unsaturated group called chromophores (Greek chroma – colour, phores – bearing).the important chromophores  are the nitro(-NO2), Carbonyl (-C=O), azo (-N=N-), nitroso (-C=N-) the quinoid rings. He named the compounds containing chromphores chromogen. this chromogen do not behaves as dyes fibers unless they are also substituted by basic or weakly acidic groups called auxochromes e.g. -NH2, and OH .The presence of these groups increases the colour yielding  power of the chromophore.

1.4            Relevance of Study: SYNTHESIS OF AZO DYE FROM 2, 4-DINITROANILINE, 3-AMINO-5-METHYLPYRAZOLE AND BYROSCARPUS COCCINEUS

This study takes a critical look at ways of producing readily available and cheaper dyes. It also provides ways to explore synthetic dyes for scientific and technological advancement using azo dyes.

1.5            Limitation of Study: SYNTHESIS OF AZO DYE FROM 2, 4-DINITROANILINE, 3-AMINO-5-METHYLPYRAZOLE AND BYROSCARPUS COCCINEUS

This research is limited to the synthesis of azo dye using 2,4-dinitroaniline as the starting material.

1.6            Problems Encountered during the Study

The major problems encountered in this research work include;

Non availability and delay in the arrival time of the chemicals since they are imported. Difficulty in choosing a suitable solvent for the purification of dye sample produced, since the dye sample does not dissolve in some of the solvent readily available.

              CONCLUSION AND RECOMMENDATION

1.1    Conclusion

This synthesis of  azo dye using 2,4-dinitroaniline, 3-amino -5-methylpyrazole and Byroscarpus coccineus result in a good yield which involve diazotization and coupling reaction in acidic medium with sodium nitrite at a low temperature ranging from 0-5°C. The colour of the azo dye produced is dark green and it depends essentially on the coupling material. The dye sample was characterized with UV-Visible and IR spectrophotometer.   1.2    Recommendation

The prepared dye in this study was not applied on textile materials in order to determine the fastness properties. Thus this area is recommended for further studies.

.

SYNTHESIS OF AZO DYE FROM 2, 4-DINITROANILINE, 3-AMINO-5-METHYLPYRAZOLE AND BYROSCARPUS COCCINEUS



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