Synthesis of Triphenylmethanol
by Markus Arnoldini
Laboratory Report
Synthesis of
Adipic acid
O
OH
HO
O
by Markus Arnoldini
1
Synthesis of Triphenylmethanol
1.
by Markus Arnoldini
Method
Oxidation of cyclohexanone with potassiumpermanganate and sodiumhydroxide as
catalyst.
2.
Reaction Equation
O
O
KMnO4
NaOH
H2O
OH
HO
O
3.
Mechanism
O
O
KMnO4, NaOH, H2O
OH
HO
O
- MnO3
OH
O
O
O
O
O
O
OH
Mn
Mn
O
O
O
O
OH
O
O
O
O
OH
O
O
Mn
OH
Mn
O
O
O
O
H2O
OH
OH
O
O
O
O
- MnO2
Mn
O
O
O
Mn
O
O
O
O
2
Synthesis of Triphenylmethanol
4.
by Markus Arnoldini
Physical properties of the substances
Potassium permanganate [1]
molar weight
density
melting point
boiling point
refraction index
WGK
GK (CH)
R-phrases
KMnO4
S-phrases
158.04 g/mol
2.70 g/cm3 (20 ºC)
> 240 ºC (Zersetzung)
3
3
R 8 (Contact with
combustible material may
cause fire)
R 22 (Harmful if
swallowed)
R 50/53 (Very toxic to
aquatic organisms, may
cause long-term adverse
effects in the aquatic
environment)
S 60 (This material and its
container must be disposed
of as hazardous waste)
S 61 (Avoid release to the
environment. Refer to
special instructions /
Safety data sheets)
Cyclohexanone [1]
O
molar weight
density
melting point
boiling point
refraction index
WGK
GK (CH)
R-phrases
S-phrases
3
98.15 g/mol
0.95 g/cm3 (20 ºC)
-31 ºC
~ 155 ºC
1.4507 (20 ºC)
1
4
R 10 (Flammable)
R 20 (Harmful by
inhalation)
S 25 (Avoid contact with
eyes)
Synthesis of Triphenylmethanol
by Markus Arnoldini
Sodium Hydroxide (spots) [1]
molar weight
density
melting point
boiling point
refraction index
WGK
GK (CH)
R-phrases
S-phrases
NaOH
40.00 g/mol
2.13 g/cm3 (20 ºC)
323 ºC
1390 ºC (1013 hPa)
1
R 35 (Causes severe burns)
S 26 (In case of contact
with eyes, rinse
immediately with plenty of
water and seek medical
advice)
S 36/37/39 (Wear suitable
protective clothing, gloves
and eye/face protection)
S 45 (In case of accident or
if you feel unwell, seek
medical advice
immediately. Show the
label where possible)
Hydrochloric Acid (conc.) [1]
HCl
molar weight
density
melting point
boiling point
refraction index
WGK
GK (CH)
R-phrases
S-phrases
4
36.46 g/mol
~ 1.19 g/cm3 (20 ºC)
1
2
R 34 (causes burns)
R 36 (irritates eyes)
R 37 (irritates respiratory
system)
R 38 (irritates skin)
S 26 (in case of contact
with eyes rinse with a lot
of water and seek medical
help)
Synthesis of Triphenylmethanol
by Markus Arnoldini
Adipic Acid [1]
molar weight
density
melting point
boiling point
refraction index
WGK
GK (CH)
R-phrases
S-phrases
O
OH
HO
O
5.
146.14 g/mol
1.360 g/cm3 (25 ºC)
152 - 154 ºC
~ 330 ºC (1013 hPa)
1
4
R 36 (Irritates eyes)
-
Experimental accomplishment
In a 250 mL round bottom flas, 9.15 g of KMnO4 were dissolved in 75 mL of water
and, while stirring, 2.95 g (0.03 mol) of cyclohexanone were added. The resulting
mixture was haeated to 30 °C and some drops of 10 % (w/w) NaOH solution were
added. Temperature was then raised to 50 °C for 20 min and then to 100 °C for 1 min.
The mixture was then cooled down to room temperature and acidified to pH 0 with
concentrated HCl. Then it was put in the fridge overnight. The resulting crystals were
then filtered, washed with cold water and characterized. An amount of 2.79 g (0.019
mol) of product was received.
For the calculation of the yield the molar amount of received product was
divided by the molar amount of reactants used, and then multiplied by 100. This
calculation yields a percentage of 63.3%:
0.017 mol
 100%  63.3%
0.03mol
6.
Experimental setup
LaboBib©
300
50
1500
AN
AN
AUS
AUS 1000
100
0 U/min
250
500
o
C
200
150
5
750
Synthesis of Triphenylmethanol
7.
by Markus Arnoldini
Analytical results
Melting point:
149 – 153 °C
Peaks in IR Spectrum (in cm-1):
2900-2980:
1600-1730:
1250-1300:
C-H
C=O
C-O
8.
Sources
[1]
[2]
http://ch.chemdat.info/mda/ch/de/
meanings of R-phrases:
http://www.chemie.fu-berlin.de/chemistry/safety/r-saetze_en.html
meanings of S-phrases:
http://www.chemie.fu-berlin.de/chemistry/safety/s-saetze_en.html
[3]
6