This document is a project report submitted by Sujit Soumitra Sahoo, Basudev Baral, and Suchismitra Mishra for their M.Sc in Applied Chemistry. The report discusses diazotization reactions, the synthesis of various azo dyes including Methyl Red and Methyl Orange, and an analysis of the antimicrobial activities of the synthesized azo dyes. Key experiments included the diazotization of sulfanilic acid and anthranilic acid, and coupling reactions to synthesize the azo dyes. The report also provides background on diazonium salt reactions and applications of azo dyes as indicators and in sulfa drug synthesis.

1. DIAZOTISATION REACTIONS, SYNTHESIS AND APPLICATIONS
PORJECT REPORT
SUBMITTED IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE AWARD OF DEGREE
IN
M. Sc. IN APPLIED CHEMISTRY
BY
SUJIT SOUMITRA SAHOO
BASUDEV BARAL
SUCHISMITA MISHRA
UNDER THE GUIDANCE OF
DR.A.N.ACHARYA
ASSOCIATE PROFESSOR
DEPARTMENT OF CHEMISTRY
aacharya@cet.edu.in
DEPARTMENT OF CHEMISTRY,
COLLEGE OF ENGINEERING AND TECHNOLOGY
(A CONSTITUENT COLLEGE OF BPUT,ODISHA)
TECHNO CAMPUS,GHATIKIA,BHUBANESWER-751003.

2. www.cet.edu.in
DIAZOTISATION REACTIONS, SYNTHESIS AND APPLICATIONS
BY
SUJIT SOUMITRA SAHOO (REGD. NO. 1311106002)
BASUDEV BARAL (REGD. NO. 1311106007)
SUCHISMITA MISHRA (REGD. NO. 1311106011)
UNDER THE GUIDANCE OF
DR.A.N.ACHARYA
ASSOCIATE PROFESSOR
DEPARTMENT OF CHEMISTRY
aacharya@cet.edu.in
DEPARTMENT OF CHEMISTRY,
COLLEGE OF ENGINEERING AND TECHNOLOGY
(A CONSTITUENT COLLEGE OF BPUT,ODISHA)
TECHNO CAMPUS,GHATIKIA,BHUBANESWER-751003.
www.cet.edu.in
2

3. ABSTRACT
SYNTHESIS OF AZODYES(METHYL ORANGE, METHYL RED) AND THEIR
ANTIMICRBIAL ACTIONS STUDY. SIMPLE SYNTHESIS OF DIAZOTISED
IMIDASOLEAZO-BENZENE LIGAND IN LABROTARY CONDITIONS AND ITS UV-
VISIBLE SPECTRA STUDY.
KEYWORDS:DIAZOTISATION REACTION, DIAZOCOUPLING(METHYL
ORANGE,METHYL RED),UV-VISIBLE SPECTRA, ANTIMICROBIAL ANALYSIS.
3

4. CERTIFICATE
COLLEGE OF ENGINEERING & TECHNOLOGY, BHUBANESWAR
This is to certify that the project report entitled “DIAZOTISATION REACTIONS,
SYNTHESIS AND APPLICATIONS”, submitted to Biju Patnaik university of
technology, Odisha by Sujit Soumitra Sahoo, Basudev Baral, Suchismita Mishra
bearing registration number 1311106002, 1311106007, 1311106011 respectively,
for the award of the degree of 2-yr M.Sc. in Applied Chemistry, is a bona fide
record of an authentic work carried out by them under my supervision.
The candidates have fulfilled all the prescribed requirements. The project
is in standard fulfillment of all the requirements for the award of the degree of
Master of Science in Applied Chemistry.
To the best of my knowledge the matter embodied in this project report has been
submitted to any other university/institute for the award of degree or diploma.
Dr. A. N. ACHARYA HEAD DEPARTMENT
(PROJECT SUPERVISER) DEPT. OF CHEMISTRY
EXTERNAL EXAMINER
4

5. ACKNOWLEDGEMENTS
We express our deepest appreciation and gratitude to every individual who encouraged
and supported us during this project.
We express our deepest regards and thanks to Dr. A.N. Acharya for mentoring, guiding
and aiding the project. We thank Dr. A.N. Acharya for generously providing his valuable
time, knowledge and experience at al times. Without his encouragement this project
would have only been an idea in the sea of thoughts.
We are thankful to Miss. P. Jena madam and Miss. Reba madam for access to the
analytical research laboratory. We express our warm thanks to every individual with
whom we discussed this project, for their cooperation and the department of chemistry
for their moral support. We express our sincere thanks to Asst. Professor Dr. B.R. Das,
Head of the Department of Chemistry for the opportunity to undertake this project. We
also like to thank him for his kindness and guidance. We are thankful to Mr. B.
Samantray for his endeavor and advice that have removed many imperfections. We
would be committing grave injustice if we fail to mention Dr. D.K. Tripathy and Dr. S.
Das sir, who have been inspirational and a source of knowledge and hope.
A special thanks to Mani Didi of Dept. of Chemistry laboratory for her assistance. We
take this opportunity to thank all my classmates and friends.
Lastly we are thankful to Dr. B.C. Bhatta for his cooperation to solve the laboratory
problems.
SUJIT SOUMITRA SAHOO BASUDEV BARAL SUCHISMITA MISHRA
5

6. CONTENTS
1. INTRODUCTION (Diazotisation reaction)
2. APPLICATION (Indicators, Sulpha drugs)
3. OTHER DIAZONIUM SALT REACTIONS
(a) Reaction of Nucleophile at Nitrogen atom
(b) SN1 Reaction
(c) One electron reduction
4. EXPERIMENT
(a) Diazotisation
(b) Synthesis of azo dyes
(Methyle red, Methyle orange, Imidazole azo benzene[L])
5. STUDY OF ANTI MICROBIAL ACTIVITIES OF AZO DYES
6. CONCLUSION
7. REFERENCES
6

7. INTRODUCTION
DIAZOTISATION REACTION
A reaction in which –NH2 group is converted into diazo group (-N+
Ξ N) is called
diazotization. Primary amine forms diazonium salt at low temperature (0 – 5)O
C .
Addition of aqueous solution of NaNO2 to a solution of aniline in presence of HCl which
is cooled to below 0- 50
C, diazotization of primary aromatic amine occurs.
Diazonium salts are stable in cold aqueous solution.
The electrophile used to react with the amine to form the aryl diazonium salt is the mild
+
NO electrophile . The following mechanism shows how the aryl diazonium salt forms
from HCl and NaNO2 .The +
NO ion is resonance stabilized. So it forms readily.
7

8. After the +
NO electrophile forms, it reacts in acidbase form with the amine nitrogen.
The intermediate then loses water and forms the diazonium salt, thus completing the
diazotisatoin process.
8

9. Diazonium salts can be used as synthetic intermediate for a number of substituted
aromatic compound e.g. nucleophiles displaces the –N+
2 group, so aryl diazonium salts
can be used in reaction to prepare a number of substituted aromatic compounds.
Although diazonium salts are relatively weak electrophile, they do react well with
strongly activated aromatic rings. Diazonium salts can also be used as electrophiles to
substitute onto another system .This type of electrophilic aromatic substitution reaction
is called azo coupling .
Chemists mostly use the –OH and –NR2 groups to activate the ring. The product
formed in azo coupling reaction contains the azo functional group(-N=N-) and have the
general structure of Ar –N=N –Ar.
4-phenylazophenol(an azo compound)
9

10. APPLICATIONS
Most of azo compounds are highly coloured and make excellent dyes. These dyes are
called azo dyes and these are usually more stable and retain their bright colours better
than most other dyes.
10

11. INDICATORS
The colour of the conjugate acid and the conjugate base form of the azo dyes are
different for which these dyes are widely used as indicators.
e.g. (1) Methyl red (2) Methyl orange
These are prepared by coupling of dimethyl aniline with diazotized anthranilic acid and
diazotized sulphanilic acid respectively.
11

12. SULPHA DRUGS[PRONTOSIL]
sulfa drugs are active against bacterial infection. One of the sulfa drug discovered that
is p-[(2,4-diaminophenyl)azo]benzenesulfonamide .
p-[(2,4-diaminophenyl)azo]benzenesulfonamide
Gerhard Domagk, synthesized this azo dye analogue, was awarded the 1939 Nobel
Prize in medicine or physiology for this work.
OTHER DIAZONIUM SALT REACTIONS
1. The most common example of the azo substitution reaction is the Sandmeyer reaction.
2. Another example of an azo substitution reaction is the Schiemann reaction
3. To prepare an aryl iodide, stir the diazonium salt with KI at r.t. until the aryl iodide
forms.
12

13. 4. Another important reaction involving diazonium salts is the formation of phenols
by heating the solution .
5. In this reaction, the diazonium salt is mixed with hypophosphorus acid
(H3PO2).
6. Using deuteriohypophosphorus acid (D3PO2) instead of H3PO2, allows the
selective replacement of a deuterium on the ring.
REACTION OF NUCLEOPHILE AT NITROGEN
Nucleophiles react with diazonium ions to give covalent diazo-compounds.
13

14. Para azo phenol
SN1 REACTION
Diazonium salts decompose on warming into nitrogen and aryl cation which is highly
reactive and could be attacked by any nucleophile in its vicinity.
phenol
ONE ELECTRON REDUCTION
Diazonium ions could be reduced by single electron transfer to give an aryl radical and
nitrogen. Copper(I) is frequently used for this purpose and the aryl radical is highly
reactive capable of abstracting a ligand from the transition metal ion or a hydrogen
atom from a covalent bond.
Chloro benzene
14

15. EXPERIMENT
All the chemicas and or reagents used were of AR grade.
DIAZOTIZATION REACTION
Place 200 mg of sulfanilic acid in a 50-ml Erlenmeyer flask. Add 60 mg of anhydrous
Na2CO3 and 2-ml of water. Warm this mixture gently on the sand bath to dissolve the
solids. Then, cool the solution to room temperature. Add 85 mg of NaONO (sodium
nitrite). Stir to dissolve. Upon cooling in an ice-water bath add ~ 2 g of ice with six drops
of conc. HCl in a reaction tube. Pour this mixture into the Erlenmeyer flask. Stir
thoroughly. The diazonium salt should begin to form within 2-5 mins. It will appear as a
white suspended precipitate. Set this suspension aside in the ice-water bath in
preparation for the coupling reaction.
SYNTHESIS OF AZODYES
SYNTHESIS OF METHYL RED
REACTION
PROCESS
(A) Dissolve 10gm anthranilic acid with 2.5gm Na2CO3 in 100 ml water. Add solution
of 3 gm NaNO2 in 20 ml of water. Cool the mixture in ice bath to about 50
C. Add
a solution of 5ml HCl in 10 ml of water gradually keeping the temperature below
50
C.
15

16. (B) Prepare a solution of 6 ml N-N-Dimethylaniline in a mixture of 6ml conc. HCl and
20 ml of water. Cool to about 50
C. Add solution (B) into (A) with stirring. Make
the whole bulk alkaline by addition of 10% NaOH solution (20ml) drop wise.
Then add 10ml saturated sodium chloride solution. Heat the mixture to boiling. It
was filtered after cooling and washed with cold water and dried. Recrystallization
was made using hot water which gives deep red crystal.
SYNTHESIS OF METHYL ORANGE
Methyl orange
PROCESS
(A) Dissolve 10gm sulphanilic acid in the solution of 2.5gm Na2CO3 in 100ml water.
Add solution of 3gm NaNO2 in 20ml of water. Cool the mixture in ice bath to
about 50
c. Add a solution of 5ml HCl in 10 ml of water gradually keeping the
temperature below 50
c.
(B) Prepare a solution of 6 ml N-N-Dimethylaniline in a mixture of 6ml conc. HCl
and 20 ml of water. Cool to about 50
C. Add solution (B) into (A) with stirring.
Make the whole bulk alkaline by addition 10% NaOH solution (20ml) drop wise.
Then add 10ml saturated sodium chloride solution. Heat the mixture to boiling.
16

17. Cool first to room temperature and then in ice bath. Filter and wash with cold
water and dry . Recrystallized from hot water gives pale yellow crystal.
Synthesis of ligand[L] (Imidazoleazobenzene)
1.Take 6.5ml of aniline.It is dissolved in aq. HCl(6ml approx. conc.) and cool it within 0-
50
C in an icebath.
2.Take NaNO2 5g. dissloved in 20ml water and cool it within 0-5o
C in an ice bath.
3.Then aq.NaNO2 soln.is added slowly to the aniline hydrochloide soln. at 0-50
C.
4.When the resulting soln. indicated the presence of excess HNO2(indicated by starch
iodide paper blue),then the reaction is completed with formation of yellow diazonium
salt.
5.Take imidazole(10g) dissloved in 20ml water.The freshly prepared diazonium salt is
added to it over a period of 1hours at 0-5o
C with pH maintained at 8-9 with addtion of
Na2 CO3 (10g.in 50ml water).
6.Constant stirring is maintained while adding diazonium salt to the imidazole soln.
7.After 30 mins.,the mixture is neutralised with 2N HCl.
8.The resulting ppt. is recrystalised from chloroform-hexane(3:1) mixture (b.p.=173.04o
C).
17

18. RESULT AND DISSCUSSION
The ligand we got from experiment are taken into consideration as our required ligand
. we have to charecterise by uv-visible spectra analysis .
Charecterisition of Uv-visible spectra
First take 10mg of ligand in a 50ml volumetric flask . Add methanol and make up to
the volume and prepare solution . Now prepare three samples . In the first sample ,
(pH= 9.77)
4ml of that ligand(L) solution is taken in a 25ml volumetric flask. Now
add 0.1M NaOH (4 drops) and make up to the volume . Now 1 ml from the mixture is
diluted with 10 times water .
Take few drops and observe for uv-visible spectra . the followig spectra results a
smooth curve of Ʌmax= 361.97 nm and A = 0.23261 .
18

19. 200.0 250 300 350 400 450 500 550 600.0
0.002
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.500
nm
A
Wave length in (nm) absorption of 0.1M NaOH in ligand[L] solution
In the second sample (pH=3.74) ,
4ml of that ligand solution is taken in a 25ml volumetric flask . now add 0.1M
HClO4 (4 drops) and make up to volume . now 1ml of the mixture is diluted with 10
times water . take few drops and observe for uv-visible spectra . the following spectra
results a large peak at Ʌmax=355.01 nm and A= 0.26109 and a smll peak at Ʌmax=
233.09 nm and A=0.12163 .
19

20. 200.0 250 300 350 400 450 500 550 600.0
0.002
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.500
nm
A
Wavelength in (nm) absorption of 0.1M HClO4 in ligand [L] solution
In the third sample (Ph= 6.13)
4ml of that ligand solution is taken in a 25 ml volumetric flask. Now dilute the
solution with water and make up to volume . take 1 ml of the mixture dilute with 10
times water and few drops taken for uv-visible observation .the following spectr results
a large peak at Ʌmax=359.107 nm and A = 0.24665 and asmall peak at Ʌmax= 232.51
nm and A= 0.11223 .
(NOTE :- The standard of buffer taken for pH study = 6.84)
20

21. 200.0 250 300 350 400 450 500 550 600.0
0.002
0.05
0.10
0.15
0.20
0.25
0.30
0.35
0.40
0.45
0.500
nm
A
Wavelengt in(nm) absorption of dilute solution of 1ml ligand[L] solution
Determination of pK
[ L ] = ligand conc. , [LH+
] = conc. of ligand in acidic medium
€1 = extinction coeff. Of [LH+
] , €2 = extinction coeff. Of [L]
K= equilibriumconst. Of reversible reaction
Optical density(OD) = €1 [LH+
] + €2 [ L ]
21

22. K = [L][H+
]/[LH+
] ,
[LH+
] = [L][H+
] / K
Now , total ligand conc. = [LT] = [LH+
]+[L] = [L][H+
] / K + [L] = [L] { 1 + [H+
]/K}
 OD = €1[L][H+
] / K + €2 [L] = [L] { €1[H+
]/K + €2 }
 OD/ LT = 1/ (1+ [H+
]/K ) { €1[H+
]/K + €2 }
 €obs (1+ [H+
]/K ) = €1[H+
]/K + €2
 €obs + €obs [H+
]/K = €1[H+
]/K + €2
 €obs - €2 = [H+
]/K (€1 - €obs )
 (€obs - €2) / (€1 - €obs ) + 1 = [H+
]/K + 1
 (€obs - €2)+ (€1 - €obs ) / (€1 - €obs ) = [H+
]/K + 1
 €1 - €2 / €1 - €obs =[H+
]/K + 1
 1/€1 - €obs = 1/€1 - €2 + (1/€1 - €2 )([H+
]/K )
 1/OD1 – ODobs = 1/ OD1-OD2 + 1/OD1 –OD2 . [H+
]/K
 1/ ∆OD = 1/ OD1 – OD2 + 1/ OD1 – OD2 . [H+
]/K
 INTERCEPT(I) = 1/ OD1 – OD2
22

23.  SLOPE(S) = 1/ OD1 – OD2 . 1/K
 INTERCEPT(I)/SLOPE(S) = K
STUDY OF ANTIMICROBIAL ACTIVITY OF AZO DYES
The azo compounds synthesized were tested against antimicrobial activity. The three
azo dyes were further used individually to analyze its antimicrobial activity against six
human pathogens namely Escherichia coli, Bacillus cereus,Bacillus substilis,
Staphylococcus aureus, Pseudomona aeruginosa and Salmonella typhi. Antimicrobial
analysis of the azo dyes A, B and C were done using standard agar-well diffusion
methods. Antimicrobial activity was evaluated by measuring the diameters of the zone
of inhibition in mm against the test microorganisms. The antibacterial activity of the
synthesized azo dyes was compared with ciproflaxin.
TABLE
23

24. .
(RESULT OF ANTI MICROBIAL STUDY OF AZO DYES)
CONCLUSION
In summary, different types of diazotization reactions are presented along with their
synthetic procedures and some of their applications.
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