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Experiment 16: Synthesis of 1-Phenylazo-2-Napthol: Pre-Lab and Post-Lab Discussion + Experimental Results

The amine component is the portion with the -NH2 group. The coupling component is the portion containing the -N=N- bond, which coincides with the site of electrophilic aromatic substitution (C1 position) that has more electron donating groups (EDGs).

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Bianca Virtudaso
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141 views

Experiment 16: Synthesis of 1-Phenylazo-2-Napthol: Pre-Lab and Post-Lab Discussion + Experimental Results

The amine component is the portion with the -NH2 group. The coupling component is the portion containing the -N=N- bond, which coincides with the site of electrophilic aromatic substitution (C1 position) that has more electron donating groups (EDGs).

Uploaded by

Bianca Virtudaso
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Experiment 16: Synthesis of

1-phenylazo-2-napthol
Pre-lab and Post-lab Discussion + Experimental Results
Pre-Lab Discussion
Objectives
• To synthesize a red-orange azo dye called SUDAN-1 or 1-PHENYLAZO-
2-NAPHTHOL using the two-pot synthesis method

• To purify the synthesized dye using recrystallization

• To utilize ingrain dyeing to color cotton fabric using the synthesized


dye
Sudan-1
• also known as CI Solvent Yellow 14 and
Solvent Orange R
• organic dye classified as an azo dye
• it has a red orange color and historically
used to color waxes, oils, petrols, and
solvents
• was also used to color food but was
banned because it was found to be a
carcinogen
What is an Azo dye
• conjugated compounds containing the ‘azo’ (R−N=N−R′) functional
group
• generally used to dye textiles, leather, amd some food items.
(e.g. Sudan-1)
What is an Azo dye
Azo group

Azo group
Procedure
Two pot synthesis
a synthesis method where the
precursors are prepared at
separate vessels
Preparation of Phenyldiazonium

1 2 3
Preparation of β-Naphtoxide

1
Synthesis of Sudan-1
• Combine phenyldiazonium
and β-naphtoxide

• purify the crude product via


recrystallizion using 30mL
hot ethanol
• recall the exp 2 (benzoic acid)
Ingrain Dyeing

1 2 3
Experimental Results
Theoretical results
Sudan-1 is a red orange powder as shown
in the photo.
It has a MP range of 131-133oC

Ingrain dyed fabric


Post-Lab Discussion
Synthesis of Sudan-1
• Two-pot synthesis
method was done in
synthesizing Sudan-1
Synthesis of Sudan-1 (cont.)
Reaction Mechanism
• General reaction → Electrophilic Aromatic Substitution
Two-Pot Synthesis
• In conducting the two-pot synthesis, two reaction systems must be
prepared
▪ Beta-Napthoxide ion
▪ Phenyldiazonium ion
• After preparing the precursors, the dye was then synthesized due to
the coupling reaction of the precursors
Preparation of Beta-napthoxide ion
• NaOH enhances the electron donating capability of the -OH group in
the napthoxide by converting it into an oxide
Sources of error (Preparation of Beta-
napthoxide ion)

- The presence of acid in the system could protonate the hydroxyl


group which in turn forms a carbocation due to the loss of water
- The presence of the carbocation makes the napthoxide ion very
reactive
Preparation of phenyldiazonium ion
- In the preparation of phenyldiazonium ion, diazotization process
was employed (conversion of primary aromatic amines to its
diazonium form)
- Only in strongly acidic solutions

- Step 1: Formation of nitrosyl cation


Preparation of phenyldiazonium ion
- Step 2: Reaction with primary amine
Sources of errors (Preparation of
phenyldiazonium ion)
- Temperature kept below 5 °C to prevent side reactions

- High pH will also cause side reactions


Coupling Reaction
- Mechanism: Electrophilic aromatic substitution
- Electrophile: Phenyldiazonium ion
Coupling Reaction
- There are two possible sites of attack for the electrophile →:C1 or
C3
- C1 is more favorable than C2 due to the presence of more stable
intermediates since there are larger number of contributing
resonance species in C1 (7 structures -> C1 ; 6 structures -> C2)
Applications of Sudan Dyes
- Mostly used for coloring solvents, oils, waxes, petrol, shoe , and
floor polishes
- But they are now rarely used because of the health risks it imposes
- It was found to be carcinogenic
Determination of the Amine and Coupling
component of an Azo dye

1. Locate the -N=N- group


Determination of the Amine and Coupling
component of an Azo dye

2. Label the substituents as either EDG or EWG

EWG EDG
Determination of the Amine and Coupling
component of an Azo dye

3. Locate the sites of electrophilic aromatic substitution

EWG EDG
Determination of the Amine and Coupling
component of an Azo dye
4. Check if the -N=N- bond coincides with EAS marks, that portion is
the coupling component.

EWG EDG
Note:
The side which is more
activated towards EAS
(more EDGs) is the
coupling component
most of the time.
Determination of the Amine and Coupling
component of an Azo dye

Try this on your own.


Clue: The portion with more EDGs is the coupling component.

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