Synthesis of Acid-Base Indicators

▪ Clean and oven dry 3-4 test tubes 2021/03/02 revised

▪ Collect test tube holder, latex gloves, and
dropper
▪ Reactants are corrosive; avoid
contacting with skin and eyes
▪ Latex gloves and goggles must be
worn at all times
▪ Use test tube holders to hold and
carry test tubes
▪ Place solid waste in capped recycling
bottles separately to prevent evaporating
and inhalation of the vapor
▪ Fume hood:
– Conc. sulfuric acid, phenol and guaiacol
– Use alcohol lamp to heat the reactants
1
▪ Wash hands after experiment
 Objective and Techniques
◼ Objective
◼ Learn the chemical structure, preparation, and color
change of the acid-base indicator phenolphthalein
◼ Change the substituent of phenolphthalein to change
the color
◼ Use the similar procedures to prepare the fluorescent
yellow and highlighters

◼ Techniques
◼ Alcohol lamp
◼ Decantation

2
 Preparation of Phenolphthalein

I. O O
Conc. H2SO4
C C
(catalyst)
O + 2 OH O + H2O
C C

Phthalic anhydride Phenol

HO OH

O O
Phenolphthalein
C C
O + H+ O H
C C
Conc.
O sulfuric acid O

Protonated phthalic
Phthalic anhydride anhydride
(electrophilic)
3
 Color of Phenolphthalein Indicator

O O O

C C O C O
O
OH- OH- C
C C + H2O + H2O
H+ H+

O
HO OH OH O
O
Phenolphthalein in Phenolphthalein in Phenolphthalein in
acidic soln neutral soln basic soln
(colorless) (light yellow) (magenta)

4
 Effect of Substituent on Color
O

II. O Conc.
C
O
C H2SO4 C
O + 2 OH + H2O
C H3CO OCH3
O OCH3
HO OH
Phthalic anhydride
Guaiacol Diguaiacol phthalein

O
III. C
O HO
Conc. O
C sulfuric acid
O + 2 OH C

C
O HO O OH
Phthalic anhydride
Fluorescent
Resorcinol Yellow 5
 Color of Diguaiacol Phthalein
II. O O
C C O
O
C 2OH- C
2H+ + 2H2O
OCH3 OCH3
H3CO H3CO

OH O
HO O

Diguaiacol phthalein in Diguaiacol phthalein in

acidic soln (colorless) basic soln (blue)

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 Synthesis of Fluorescent Yellow
O
III. O HO Conc. C
C H2SO4 O
O + 2 OH C + H2O
C
O
Resorcinol HO OH
OH OH
Phthalic anhydride

O
C
O O
O
C C
H2SO4 OH 2OH- O
C
-H2O C
2H + C + 2H2O

HO O OH HO O O O O O

Green Fluorescing
Fluorescent Tautomer Substance
Yellow in basic soln
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 Flow Chart I
Operate in hood React Product appearance
O
2 d. phenol
C
2 d. Conc.
O
OH Orange
C H2SO4

O

Stir and mix

2 d. guaiacol 
½ spoon Heat on flame
Phthalic OH  Purple
anhydride React
OCH3 
½ spoon resorcinol Color change
HO

Solid reactant Dark brown
disappear
OH

8
 Flow Chart II
Product from Add H2O in hood Acid-base test

Phenol Add 3 mL H2O Obtain some Add

 solid product NaOH(aq)
Stir and mix  

Product Dissolve in Add
Guaiacol precipitate out 95% ethanol HCl(aq)
 
Decant
supernatant Observe
and get solid color
Resorcinol product change

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 Procedure I - Preparation

1. One 250 mL beaker

2. One dry test tube with 1/2
spoon phthalic anhydride
3. A test tube with 3 mL H2O
4. Glass rod
5. Test tube holder

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 Procedure I. Synthesis of
Phenolphthalein

Obtain dry test tube Heat on flame for 5 s. Add 3 mL D.I. water Dissolve with 95%
ethanol
Add 1/2 spoon of Move out of flame Stir to mix and
phthalic anhydride product precipitate out Add drops of 1 M
Stir and heat NaOH to observe
2 d. phenol and 2 d.
repeatedly Decant the the color change
conc. sulfuric acid
supernatant
Mix thoroughly with Stop heating after all Add drops of 1 M
glass rod solids have dissolved Transfer a portion of HCl
solid to test tube
• Phenol and sulfuric Record color change Record color
acid are corrosive.
change
• Wear gloves 11
 Procedure II. Synthesis of
Diguaiacol Phthalein
Caution:
• Mix the reactants thoroughly
• Heat on flame for 5 s
• Move out of flame and mix
Obtain dry test tube again
• Repeat the operation till color
Add 1/2 spoon of phthalic
change and solid reactant
anhydride
disappear
• Reaction is faster than phenol
Add 2-3 d. guaiacol and
and avoid overheating
2 d. conc. sulfuric acid
• Product is sticky with dark blue
Heat to synthesize to purple color
Separate products by
adding water 12
 Procedure III. Synthesis of
Fluorescent Yellow

Obtain dry test tube Obtain a portion of Obtain 2~3 d. of soln. A

product into another test tube
Add 1/2 spoon of phthalic
anhydride Dissolve with 95% Dilute with 10%
ethanol (soln. A) ethanol until light
Add 1/2 spoon of yellow
resorcinol
2 d. conc. sulfuric acid
Caution:
Heat to synthesize The fluorescent yellow decomposes at 315°C.
Test tube should be moved in-and-out of flame
Separate products by
to avoid over heating 13
adding water
 Fluorescence Observation

Add drops of 1 M NaOH Fluorescence Take portions of soln. A

under UV light
Use black paper as
background Add polyvinyl alcohol glue

Observe fluorescence Stir with glass rod to write on paper

under UV lamp (with long /
short wavelength)
14
Caution: Avoid exposing your eyes and skin to UV light
 Fluorescent Plastic

▪ The chain of polyvinyl alcohol (PVA) can be

cross-linked by borate to form an elastomer

Cross-linking with Cross-linking with

covalent bonding hydrogen-bonding
15
 Procedure IV. Fluorescent Plastic

◼ Add 3 d. fluorescent yellow ◼ Add 4 mL PVA glue

(soln. A) in 100 mL beaker ◼ Mix with glass rod
◼ Add 1 d. of 1 M NaOH ◼ Add borate soln. drop by drop

◼ Mix thoroughly with

glass rod
◼ Observe the change
in color and viscosity
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 Notice Brief report

▪ Phenol, conc. sulfuric acid…etc. are corrosive; gloves

and goggles should be worn at all times
▪ Do not take more than 2 d. of conc. sulfuric acid.
▪ Limit the use of chemicals: the amount of chemicals used in
this experiment does not need to be precise.
▪ Take small amounts of chemicals into test tube and give out
excess chemicals to others
▪ Mix reactants thoroughly before heating
▪ Hold test tube with test tube holder, heat the reactants for ca.
5 s., and move out of flame continuously to avoid overheating
▪ Avoid exposing eyes and skin to UV light
▪ After experiment, clean test tubes with 10% alcohol, pour the
first rinsed waste liquid into recycling bin then clean with
water 17