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benzenediazonium chloride with
2-naphthol to 1-phenylazo-2-naphthol
T
T T ¼F ¤ +? T s; s; e>s; s
1017 Azocoupling of
EMBED ISISServer
Classification
Reaction types and substance classes
electrophilic substitution of aromatics, azocoupling
aromatics, diazonium salt, naphthol, dye
Work methods
stirring with magnetic stir bar, filtering, recrystallizing, use of an ice
cooling bath, heating with oil bath
batch scale 100 mmol, additional:
stirring with KPG-stirrer, adding dropwise with an addition funnel
Instruction (batch scale 10 mmol)
Equipment
250 mL Erlenmeyer flask, 100 mL Erlenmeyer flask, internal thermometer,
pipette, heatable magnetic stirrer, magnetic stir bar, suction flask, Büchner
funnel, desiccator, ice bath, oil bath
Substances
aniline hydrochloride (mp 199-202 °C)
1.43 g (11.0 mmol)
2-naphthol (mp 122-123 °C)
1.44 g (10.0 mmol)
sodium nitrite
759 mg (11.0 mmol)
conc. hydrochloric acid (35%)
2.5 mL
aqueous sodium hydroxide solution (1 M)
40 mL
ethanol for recrystallizing
about 50 mL
urea
small amount
potassium iodide starch test strips
ice
Reaction
Preparation of the diazonium salt solution:
13 g ice, 5 mL water and 2.5 mL conc. hydrochloric acid are filled in a 100
mL Erlenmeyer flask with magnetic stir bar and internal thermometer. To this
mixture 1.43 g (11.0 mmol) aniline hydrochloride are added. Under ice cooling
and stirring and at an internal temperature of 0-5 °C so much from a solution
of 759 mg (11.0 mmol) sodium nitrite in 3 mL water (about 2.5 mL) is added
slowly by using a pipette, that an excess of nitric acid is avoided. The test
for HNO2 is carried out with potassium iodide starch test strips by dropping
a sample of the reaction solution with a pipette on a test strip. A blue
coloured paper shows HNO2. So much sodium nitrite solution is added, that a
proof is positive still 5 minutes after the last addition of nitrite.
Excessive nitric acid is removed by addition of a small amount of urea.
Azocoupling:
1.44 g (10.0 mmol) 2-naphthol are dissolved in 40 mL 1 M sodium hydroxide
solution in a 250 mL Erlenmeyer flask. The solution is cooled. Under strong
stirring and ice cooling the ice cooled benzenediazonium salt solution is
added in portions. Towards the end of addition the pH value of the solution
is controlled. To keep the solution in the alkaline range, a 1 M sodium
hydroxide solution is added dropwise by means of a pipette, if necessary.
After the addition is finished, the mixture is stirred for 30 minutes at 0-5
°C.
Work up
The orange precipitated product is sucked off over a Buechner funnel and
repeatedly washed with water. The product is dried in the vacuum desiccator
until weight constancy. According to the vacuum and drying agent, the drying
procedure can last up to a few days.
Crude yield (humid): 6.5 g
Crude yield (dry): 2.20 g; mp 129 °C
The crude product is recrystallized from about 50 mL ethanol and then dried
in the vacuum desiccator.
Yield: 1.97 g (7.93 mmol, 79%); mp 134 °C
Waste management
Recycling
The ethanol from the mother liquor is evaporated, collected and redistilled.
Waste disposal
Waste Disposal aqueous filtrate solvent water mixtures,containing
halogen residue from the mother liquor dissolve in a small amount of
acetone, then: organic solvents, halogen free Time
4 hours, without time for drying
Break
Before recrystallization
Degree of difficulty
Medium
Instruction (batch scale 100 mmol)
Equipment
250 mL Erlenmeyer flask, 1 L beaker, internal thermometer, addition funnel,
heatable magnetic stirrer, magnetic stir bar, KPG-stirrer, suction flask,
Buechner funnel, desiccator, ice bath, oil bath
Substances
aniline hydrochloride (mp 199-202 °C)
14.3 g (110 mmol)
2-naphthol (mp 122-123 °C)
14.4 g (100 mmol)
sodium nitrite
7.59 g (110 mmol)
conc. hydrochloric acid (35%)
25 mL
aqueous sodium hydroxide solution (1 M)
400 mL
ethanol for recrystallizing
about 500 mL
urea
small amount
potassium iodide starch test strips
ice
Reaction
Preparation of the diazonium salt solution:
130 g ice, 50 mL water and 25 mL conc. hydrochloric acid are filled in a 100
mL Erlenmeyer flask with magnetic stir bar and internal thermometer. To this
mixture 14.3 g (110 mmol) aniline hydrochloride are added. Under ice cooling
and stirring and at an internal temperature of 0-5 °C so much from a solution
of 7.59 g (110 mmol) sodium nitrite in 3 mL water (about 25 mL) is added
slowly dropwise with an addition funnel, that an excess of nitric acid is
avoided. The test for HNO2 is carried out with potassium iodide starch test
strips by dropping a sample of the reaction solution with a pipette on a test
strip. A blue coloured paper shows HNO2. So much sodium nitrite solution is
added, that a proof is positive still 5 minutes after the last addition of
nitrite. Excessive nitric acid is removed by addition of a small amount of
urea.
Azocoupling:
14.4 g (100 mmol) 2-naphthol are dissolved in 400 mL 1 M sodium hydroxide
solution in a 1 L beaker. The solution is cooled. Under strong stirring with
a KPG-stirrer and ice cooling the ice cooled benzenediazonium salt solution
is added slowly in portions. Towards the end of the addition the pH-value is
checked. To keep the solution in the alkaline range, a 1 M sodium hydroxide
solution is added dropwise by means of a pipette, if necessary. After the
addition was finished, the mixture is stirred for 30 minutes at 0-5 °C.
Work up
The orange precipitated product is sucked off over a Buechner funnel and then
washed with 500 mL water in a 1 L beaker. The product is again sucked off
strongly and then dried in a vacuum desiccator until weight constancy.
According to the vacuum and drying agent, the drying procedure can last up to
a few days.
Crude yield (humid):160 g
Crude yield (dry): 21.5 g; mp 129 °C
The crude product is recrystallized from 500 mL ethanol and dried in the
vacuum desiccator.
Yield: 19.5 g (78.5 mmol, 79%); mp 134 °C
Waste management
Recycling
The ethanol from the mother liquor is evaporated, collected and redistilled.
Waste disposal
Waste Disposal aqueous filtrate solvent water mixtures, containing
halogen residue from the mother liquor dissolve in a small amount of
acetone, then: organic solvents, halogen free
Time
5-6 hours, without time for drying
Break
Before recrystallization
Degree of difficulty
Medium
Analytics
TLC
TLC-conditions:
adsorbant: Macherey and Nagel Polygram SilG/UV foil, 0.2
mm eluent: cyclohexane/acetic acid ethyl ester 8:2 Rf (1-phenylazo-2naphthol) 0.65 Rf (2-naphthol) 0.39
Traces of not reacted 2-naphthol can be detected in the crude product, and
also in the mother liquor from the recrystallization.
GC
GC-conditions:
column: ZB–1, 7 HM–G001-11, length 30 m, internal diameter 0.32 mm, film 0.25
µm
inlet: injector temperature 210 °C, split injection, injected volume 1
µL carrier gas: H2, pre-column pressure 50 kPa oven: 70 °C (2 min), heating
rate 10 °C/min, isotherme 300 °C (10 min) detector: FID, 310
°C integrator: Shimadzu Percent concentration was calculated from peak
areas.
GC of the product (not recrystallized)
Retention time (min) Substance Peak area %
naphthol) > 99 from 20 impurities
17.9 product (1-phenylazo-2-
IR spectrum of the pure product (KBr)
(cm-1) Assignment
valence, arene
3400 O-H-valence
3040 C-H-valence, arene
UV Spectrum (ethanol)
(max = 422 nm,
log ( = 4.05
(max = 478 nm,
log ( = 4.17
NOP
http://www.oc-praktikum.de
PAGE
PAGE
5
March 2006
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