DYE SYNTHESIS AND IT’S

CHARACTERISTICS
SUBMITTED BY
MANAS RANJAN SWAIN
MANISHA MANASWINI
MANMATH RANJAN MOHANTY
MINAKSHI SAHOO
NIBEDITA NISHANK

GUIDED BY :-
MR. BASANTA KUMAR SAHOO
( READER IN CHEMISTRY )

NAYAGARH
AUTONOMOUS COLLEGE,NAYAGARH
 CONTENTS :-
INTRODUCTION
CLASSIFICATION
EXPERIMENTAL PART
UV– ANALYSIS
CONCLUSION
 INTRODUCTION :-
DYE

A natural or synthetic substances used to add a colour to or change the colour

of something such substances with considerable colouring capacity are widely
employed in the production of consumer products ,including
paints,textile,printing inks,pharmaceutical, food ,cosmetics, plastics,
photographic and paper industries .
A Dye is a coloured compound ,normally used in solution which is capable of
being fixed to a fabric
REASON BEHIND COLOUR OF DYE :-
The colour of the Dye is caused by the absorbance of electromagnetic variation
( 400-700 nM)
If any part of this curve is in visible range , the Dye will
appeared coloured . White light is a mixture of wavelengths . Some
Of these have a relationship to the energy in the delocalised electron
Cloud of the Dye molecule.

WHAT MAKES THE DYES COLOURED ?

Dyes are basically ionising and aromatic compounds , they
have chromophores present in them . Their structure have aryl
rings that has delocalised electron systems these stuctures are said
to be responsible for the absorption of electromagnetic radiation that
has varying wavelengths based upon the energy of the electron clouds .
BASICS FOR COLOUR:-
1. Absorb light in the visible spectrum (400-700nM)
2. Have at least one chromophore (colour bearing
groups )
3. Have conjugated system i.e structure with alternating

double and single bonds .

4.exhibit resonance of electrons , which is a stabilizing
force in organic compounds .
 Most Dyes also contain groups known as auxochromes
( colour helpers)
Example:- carboxylic acid , sulphonic acid , amino acid and
hydroxyl group.
 Wavelength Colour Colour
Absorbed (nm) Absorbed observed

400-435 violet Yellow-green

435-480 Blue Yellow

480-490 Green-blue Orange

490-500 Blue-green Red

500-560 Green Purple

560-580 Yellow-green Violet

580-595 Yellow Blue

595-605 Orange Green-blue

605-700 Red Blue -green

 General Application :-
Dyes are widely applied on paper ,leather ,fur ,hair ,drugs,waxes,
cosmetics, greases , plastics ,textiles materials . There are different
types of dyes for dyeing textiles goods . These dyes have different
nature in fiber .
 CLASSIFICATION
There are several ways of classification of dye .
 Each class of dye has a very unique chemistry structure and
particular way of bonding , while some dyes can react chemically
with the substrates forming strong bonds in the process, others
can be held by physical forces .
some of the prominent ways of classifications are
 Based on the sources of material
 Based on the nature of their respective chromophores
Classification by methods of application
1. Based on the source of materials ;
a. Natural Dyes
b. synthetic dyes
 DYES
NATURAL SYNTHETIC

PLANT ANIMAL AZODYE NON-AZODYE

BASED BASED

TYRIAN
MADDER
PURPLE

ACIDIC BASIC REACTIVE DISPERSE SULFUR

Natural Dyes
 Natural Dyes or colorants derived from plants , invertebrates or
mammals .
 The majority of animal dyes are vegetable dyes from plant
sources .
Eg:- roots , berries , bark , leaves and wood
 Others organic sources include fungi and
Synthetic Dyes:-
Almost all the colours that you see today are synthetic dyes .
Synthetic dyes are used every where in every thing from clothes to
paper , from food to woods . This is because they are cheaper to
produce , brighter , more colour fast and easy to apply fabric
Eg :- Acid dyes , azo dyes , Basic dyes , mordant dyes etc..
a. Acid Dyes :-
 An acid dye is a dye , that is typically applied to atextile at low pressure . They are
mainly used to dye wool , not cotton fabrics .
 Some acid dyes are used as food colorants , and some can also be used to stain
organi in the medical field .
Eg :-Nigrosine , Picric acid , Acid faschin , congored , Alizarin ,
Methyl red

b. Basic Dyes :-
 Basic dye is a cationic stain and reacts with material , that is negatively charged .
 Usually available in synthetic form , these act as bases and are actually aniline
dyes .
 Basic dyes are used for dyeing wool, sick and crylic and modacrylic fibres .
Eg :-Crystal violet ,Methelene blue , safranin, basic fuschin
c. Disperse Dyes :-
 Disperse dyes are the only water – ion soluble dyes that dye polyester and
acetate fibres .
 Disperse dyes molecules are the smallest dye molecules among all dyes .
Eg :- Anthraquinone , nitroquinone

d. Reactive Dyes :-
 In a reactive dye ,a chromophore contains a substituent that reacts with substrate
.
 It has good fastnes properties owing to the covalent bonding that occurs during
dyeing .
 Reactive dyes are most commonly used in dyeing of cellulose like cotton or flax
or wool.
Eg:-Monochloro triazine ,Dichloro triazine , Vinyl suphone
D . Sulfur Dyes :-
 Sulfur dyes are most commonly used dyes manufactured for cotton in
terms of volume
 They are in expensive , generally have god wash –fastness and are
easy to apply
 Sulfur dyes are predominantly black ,brown , dark blue , red and lighter
scarlet colour is available .
Eg:- lindo phenol ,
In our project work we consider 3 types of Dye .
1. Azo Dye
2. Alizarine
3.Methyl red

1.Azo dye :-
Azo Dyes are organic compounds bearing the functional group R-N=N-R’ ,In
Which R and R’ are usually aryl.
 They are a commercially important family of azo compounds . That is
compounds containing the linkage C-N=N-C .
 Azo dyes are widely used to treat textiles ,leather articles , and some foods .
 Chemically related to azo dyes are azo pigments ,which are insoluble in water
and other solvents .
 Properties :-
 Azo dyes are insoluble in water .
 They are not readymade dyes ,the colour is formed in the fibre by two component
usually referred to as napthols and bases .
 The dyed goods have very good to excellent light fastness .
 The dyes have good washing fastness .
 The dyes goods suffer ,poor rubbing fastness and this can be overcome by proper
treatment .
 Alizarin:-
 It is an organic compound with formula C14H8O4 that has been used throughtout
history as a prominent red dye , principally for dyeing textile fabrics .
 Historically it was derived from the roots of plants of the madder genus .
 In 1869 ,it became the first natural dye to be produced synthetically .
 IUPAC Name – 1,2 Dihydroxyanthracene-9,10 dione
 Other name – Mordant red (||)
Turkey red
Alizarinred
 Properties :-
 Chemical formula – C14H8O4
 Molar mass -240.2149 mol
 Appearance – Orange red crystals or powder
 Density – 1.540 g/cm3
 Melting point – 279 to 2830 C
 Boiling point – 4300C(703K)
 Acidity (Pka) – 6.94
 Alizarin is the main ingredient for the manufacture of the madder lake pigments
know to painters as rose madder and alizarin crimson .
.
METHYL RED :-
 Methyl red is also called C.I acid red , is an indicator dye that turns red in
acidic solution .
 Methyl red is a PH indicator . It is red in PH under 4.4 ,yellow in PH over 6.2
and orange in between with a pka of 5.1 .
 IUPAC NAME -2{[1-(Dimethyl amino )phenyl]diazeny}benzoic acid

Properties :-
Chemical formula –C15H5N3O2
Molecular mass –
Density – 0.719 g/cm3
Melting point – 179-1820c(432-455k)
Solubility-
 Experimental part :-
AZODYE :-
CHEMICAL REQUIREDS :-
1. Napthol – 3gm
2. Aniline – 10 ml
3. NaoH solution – 5ml
4. Sodium nitrite – 2gm
PROCEDURE :-
 Prepare NaoH sdolution by dissolving sodium palet in water in a beaker .
 Weight 3gm of napthalene -2-ol and dissolve it into the sodium hydroxide
solution .
 Stir the mixture until complete dissolution , cool the sodium with ice –water
bath .
 In another beaker we take 10ml aniline and then add 2gm of sodium nitrate
into it and cool the solution with ice water bath .Then add slowly 3-4 drops of
concentrated hydrochloric acid and stir the mixture . The slightly turbid pale
grey solution is benzenediazonium salt solution is obtained .
 To the alkaline naphthalene-2-ol solution, add the benzene diazonium salt
solution slowly . Then stirred efficiently and brick red precipitate is formed .
 Filter the mixture by filter paper in a glass funnels and transfer the product to
a watch glass . Allow the product to dry .
 METHYL RED :-
CHEMICAL REQUIRED :-
1. Anthranilic acid (4.75 mol)
2. HCl
3. Sodium nitrite
4. Dimethyl aniline
5. Sodium acetate
6. Sodium hydroxide
OBSERVATION :-
 When the water was first add to the anthranilic acid ,it looked like the colour and
consistency of plain oatmeal with bubbles and foam on the surface .
 When the mixture stopped swirling ,a light tan solid formed at the buttom of
the flask . As the HCl was add dropwise ,the solution turned a medium and
darker red-brown .
 The solution then turned back to a light peach solid with cooling in the ice
bath . With stirring and the addition of the sodium nitrate solution , the solid
turned into a clear ,light amber liquid .
 As the N,N – dimethylaniline was added ,the solution turned a deep ,clear
orange , and then turned clear red as the stirring apparatus was turned on .
 The red depended after stirring for 5minutes , and then with the addition of
sodium acetate ,it turned dark and opaque with a red orange residue on the
sides of the flask.
 It looked like thinner cough syrup .After the NaOH was added , it looked
like grape juice .
 The final compound that was collected after the vacuum filtration was brick
red and pasty .
 Alizarin:-
Chemical required :-
1. Sodium perchlorate
2. Potassium hydroxide
3. Anthraquinone
4. HCl
5. Sodium hydroxide
6. Sulphuric acid
Procedure :-
 25 ml of water , 7.5 gm sodium perchlorate (NaClO4.H2O) , 75 g potassium
hydroxide and 25 g of anthraquinone are mixed in the 250 ml porcelain beaker ,
and the mixture was heated in an oil bath at 2000c for 2 hours .
 The resulting melt upon cooling is dissolved in 100 – 150 ml of warm water .
Through the obtained solution for 15 min . Air is purged then water and an
excess of line are added until no more precipitate formed .
 The released Ca salt of alizarin is filtered , suspended in water and it is
decomposed by heating with excess HCl .
 The hot solution was filtered and the precipitate was dissolved in 10% of NaOH
solution .The solution was filtered , the filtrate was heated to boiling and alizarin
was precipitate by adding hot dilute H2So4(1:1).
 The mixture was refluxed for 1 hr. ,filtered and washed with hot water to remove
H2So4 .
 Alizarin is dried in air and purified by sublimation at 3000c in a sand bath between
watch glass .
 Uv-analysis
AZODYE :-
 We pass on to describing the experimental procedure employed to obtain the
data linking the anchoring energy strengths and dichloric ratio as a measure of
photoinduced ordering .
 To this end we carried oud absorption spectra and anchoring energy
measurement for azo dye films irradiated at varying exposure time .
 Thus we used samples prepared at different irradiation doses to measure the
anchoring strengths and the dichloric ratio in relation to the dose .
 The data then can be recalculated to obtain the required anchoring energy vs
dichoric ratio dependence .
 Methyl Red:-
 It shows three UV spectra of 1.537*10-5 mol.dm-3 m-MR at the pH values 7.27 ,3.61 ,
and 2.51 representing three different forms of the dye ; the basic , neutral and di –
protonated forms ,respectively.
 In figure , the intensities of the main bands in the visible and UV region decrease with
lowering pH ,as a result of the gradual transformation of m-MR From it’s basic form
with a strong yellow colour to it’s red coloured neutral form .
 The neutral form of azo dye generally has a weaker absorption band and hence less
intense colour .
 Another important observation is that a band around 218nm starts to appear as result
of the protonation of the carboxylate ion to form the carboxyl group , which absorbs
generally around 220 nm .
 The presence of an isobestic point at 508nm in figure it is an indication of the
presence of the first equilibrium between the basic and neutral forms of the m-MR
where a shoulder at 530nm grows with decreasing pH, resulted from the formation of
the neutral form.
 Alizarin

  UV –spectra of alizarin red S in aqueous media exhibit to major absorption
bands in region 300-600 nm . Both bands are the * transition owing to the
presence of the p-benzoquinone group ,condensed between two rings , in
the structure of alizarin red S dye giving absorption maximum at 330 and
426 nm respectively .
 The n−𝜋* of diketones in the diketo form gives rise to two bands ; one in the
usual region near 290nm and a second that stretches in to the visible 340-
440 nm to give yellow colour to some of these compounds that seems true
for our dicarbonyl organic dye attributed to slight shift of bands at longer
due to two hydroxyl groups (auxochromes ) at the substituted benzene
ring .
 Change in absorption at maximum wavelength may also be result of
structure strength and chromophore distortion .
CONCLUSION
 YO U
ANK
TH