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Polymer Chemistry

The document discusses the synthesis and properties of various dyes, including methyl red, methyl orange, Congo red, malachite green, p-rosaniline, phenolphthalein, fluorescein, and eosin. Each dye is characterized by its chemical composition, synthesis process, and pH-dependent color changes, making them useful as indicators in various applications. The document highlights the significance of these dyes in chemistry and their practical uses in staining and titration.

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43 views18 pages

Polymer Chemistry

The document discusses the synthesis and properties of various dyes, including methyl red, methyl orange, Congo red, malachite green, p-rosaniline, phenolphthalein, fluorescein, and eosin. Each dye is characterized by its chemical composition, synthesis process, and pH-dependent color changes, making them useful as indicators in various applications. The document highlights the significance of these dyes in chemistry and their practical uses in staining and titration.

Uploaded by

mahileshgomathi
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PPTX, PDF, TXT or read online on Scribd
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Dye Chemistry : Synthesis of Methyl Red

As an azo dye, methyl red may be prepared by diazotization of anthranilic acid,


followed by reaction with dimethylaniline

Methyl red (2-(N,N-dimethyl-4-aminophenyl) azobenzenecarboxylic acid), also


called C.I. Acid Red 2, is an indicator dye that turns red in acidic solutions. It is an
azo dye, and is a dark red crystalline powder. 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

Color transition of methyl red solution under different acid–base


conditions. Left: acidic, middle: about pH 5.1 (the pKa), right: alkaline
Dye Chemistry : Properties of Methyl Red

The color of methyl red is pH dependent, because protonation causes it to adopt a


hydrazone/quinone structure
Dye Chemistry : Synthesis of Methyl Orange

The reaction of sulfanilic acid in the presence of sodium nitrite and hydrochloric acid
(temperature, 0-5C) and N,N-dimethylaniline gives the product Methyl orange.

IUPAC of methyl orange is Sodium-4-{ [4- (dimethylamino)phenyl]diazenyl}benzene-


1-sulfonate
Dye Chemistry : Properties of Methyl Orange

Methyl orange is a pH indicator frequently used in titration because of its clear and
distinct color variance at different pH values. Methyl orange shows red color in acidic
medium and yellow color in basic medium

In a solution that decreases in acidity, methyl orange moves from the color red to
orange and finally to yellow with the opposite occurring for a solution increasing
in acidity. This color change from yellow to red occurs because the protons in the
acidic solution react with the N=N bond of the molecule, protonating one of them
and changing the visible light absorption of the molecule to reflect more red light
than orange/yellow.

In an acid, it is reddish and in alkali, it is yellow. Methyl orange has a pKa of 3.47
in water at 25 °C
Dye Chemistry : Synthesis and Properties of Congo Red

Congo red is a benzidine-derived dye that is prepared by azo coupling of the bis
(diazonium) derivative of benzidine with naphthionic acid.

It is a carcinogenic dye and has fallen into disuse-derived dye


Congo red is an organic compound, the sodium salt of 3,3′-([1,1′-biphenyl]-4,4′-
diyl)bis(4-aminonaphthalene-1-sulfonic acid)

Congo red (pH indicator)


below pH 3.0 above pH 5.2
3.0 ⇌ 5.2
Dye Chemistry : Synthesis and Properties of Malachite Green

Malachite green is an organic compound that is used as a dyestuff and


controversially as an antimicrobial in aquaculture.

Malachite green is traditionally used as a dye for materials such as silk, leather,
and paper.

Despite its name the dye is not prepared from the mineral malachite; the name just
comes from the similarity of color
Dye Chemistry : Synthesis and Properties of Malachite Green

Malachite green is classified in the dyestuff industry as a triarylmethane dye and also
using in pigment industry.

Malachite green is prepared by the condensation of benzaldehyde and dimethylaniline to


give leuco malachite green (LMG):
C6H5CHO + C6H5N(CH3)2 → (C6H5N(CH3)2)2C6H5 + H2O

Second, this colorless leuco compound, a relative of triphenylmethane, is oxidized to the


cation that is MG:
C6H5CH(C6H4N(CH3)2)2 + HCl + ½ O2 → [C6H5C(C6H4N(CH3)2)2]Cl

Malachite green (first transition) (pH indicator) Malachite green (second transition) (
pH indicator)
below pH 0.2 above pH 1.8
below pH above pH
0.2 ⇌ 1.8 11.5 13.2
11.5 ⇌ 13.2
Dye Chemistry : Synthesis and Properties of p-Rosaniline

It is prepared by the condensation of aniline and p -aminobenzaldehyde

It is used to dye polyacrylonitrile fibers. It is used to detect sulfur dioxide

Pararosaniline is used as a colorimetric test for aldehydes, in the Schiff test.

It is the only basic fuchsine component suitable for making the aldehyde-fuchsine stain for
pancreatic islet beta cells
Dye Chemistry : Synthesis and Properties of p-Rosaniline
Dye Chemistry : Synthesis and Properties of Phenolpthalein

The synthesis is carried out by condensation of phthalic anhydride with


phenol, and involves an (acid-catalyzed) reaction.

Phenolphthalein is often used as an indicator in acid–base titrations. For this


application, it turns colorless in acidic solutions and pink in basic solutions. It
belongs to the class of dyes known as phthalein dyes

Phenolphthalein (pH indicator)


below pH 8.3 above pH 10.0
8.3 ⇌ 10.0
Dye Chemistry : Synthesis and Properties of Phenolpthalein and
Fluorescein
Dye Chemistry : Synthesis and Properties of Fluorescein

The method involves the reaction of phthalic anhydride and resorcinol,


Approximately 250 tons were produced in the year 2000.

In some cases, acids such as zinc chloride and methanesulfonic acid are
employed to accelerate the Friedel-Crafts reaction as catalyst

Fluorescein under UV illumination


Fluorescein is an organic compound and dye based on the xanthene tricyclic
structural motif, formally belonging to triarylmethine dyes family. It is available as a
dark orange/red powder slightly soluble in water and alcohol. It is used as a
fluorescent tracer in many applications.

Red color in acidic medium and green in basic medium

In acidic media (1) cyclizes to form a lactone (2)


Dye Chemistry : Synthesis and Properties of Eosin

Eosin is synthesized by bromination of Fluoresein or Nitration of fluorescien

Eosin is the name of several fluorescent acidic compounds which bind to


and form salts with basic, or eosinophilic, compounds like proteins
containing amino acid residues such as arginine and lysine, and stains them
dark red or pink as a result of the actions of bromine on eosin. In addition to
staining proteins in the cytoplasm, it can be used to stain collagen and
muscle fibers for examination under the microscope.
Dye Chemistry : Synthesis and Properties of Eosin

Left side: Eosin Y; Right Side: Eosin B


Eosin is the most commonly used dye to stain the cytoplasm. This dye is acidic in nature
that binds to basic cell components like proteins in the cytoplasm.

It produces vibrant pink colour. Thus, it is used in many experiments based on water
transportation through the xylem in plants.

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