Synthesis of Triphenylmethanol by Markus Arnoldini

Synthesis of Triphenylmethanol by Markus Arnoldini

Laboratory Report

Synthesis of

Adipic acid

by Markus Arnoldini

1. Method

Oxidation of cyclohexanone with potassiumpermanganate and sodiumhydroxide as catalyst.

2. Reaction Equation

3. Mechanism

4. Physical properties of the substances

Potassium permanganate[1]
KMnO4 / molar weight / 158.04g/mol
density / 2.70g/cm3 (20ºC)
melting point / 240ºC(Zersetzung)
boiling point / -
refraction index / -
WGK / 3
GK (CH) / 3
R-phrases / 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-phrases / 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]
/ molar weight / 98.15g/mol
density / 0.95g/cm3 (20ºC)
melting point / -31ºC
boiling point / ~155ºC
refraction index / 1.4507 (20ºC)
WGK / 1
GK (CH) / 4
R-phrases / R 10 (Flammable)
R 20 (Harmful by inhalation)
S-phrases / S 25 (Avoid contact with eyes)
Sodium Hydroxide (spots)[1]
NaOH / molar weight / 40.00g/mol
density / 2.13g/cm3 (20ºC)
melting point / 323ºC
boiling point / 1390ºC (1013hPa)
refraction index / -
WGK / 1
GK (CH) / -
R-phrases / R 35 (Causes severe burns)
S-phrases / 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 / 36.46 g/mol
density / ~1.19g/cm3 (20ºC)
melting point / -
boiling point / -
refraction index / -
WGK / 1
GK (CH) / 2
R-phrases / R 34 (causes burns)
R 36 (irritates eyes)
R 37 (irritates respiratory system)
R 38 (irritates skin)
S-phrases / S 26 (in case of contact with eyes rinse with a lot of water and seek medical help)
Adipic Acid [1]
/ molar weight / 146.14g/mol
density / 1.360g/cm3 (25ºC)
melting point / 152-154ºC
boiling point / ~330ºC (1013hPa)
refraction index / -
WGK / 1
GK (CH) / 4
R-phrases / R 36 (Irritates eyes)
S-phrases / -

5. 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%:

6.Experimental setup

7. Analytical results

Melting point:149 – 153 °C

Peaks in IR Spectrum (in cm-1):2900-2980: C-H

1600-1730:C=O

1250-1300:C-O

8. Sources

[1]

[2] meanings of R-phrases:

[3] meanings of S-phrases:

1