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CPP-1.5 (1.1) Practical Organic Chemistry
DOS & R in Organic Chemistry, TUT Page 1
Prepared By
Dr. Krishnaswamy G
Faculty
DOS & R in Organic Chemistry
Tumkur University
Tumakuru
CPP-1.5 (1.1) Practical Organic Chemistry
DOS & R in Organic Chemistry, TUT Page 2
Oxidation of Cyclohexanol or Preparation of Adipic
acid from cyclohexanol
AIM:
To prepare Adipic acid from cyclohexanol by oxidation.
PRINCIPLE:
Adipic acid is a dicarboxylic acid with IUPAC name Hexane-1,6-dioic
acid with the formula (CH2)4(COOH)2. Fromm an industrial perspective,
it is the most important dicarboxylic acid used as monomer for the
production of nylon by polycondensation reaction with hexamethylene
diamine forming 6, 6,-nylon. Hence, the purpose of this experiment is to
synthesize Adipic acid through oxidation of cyclohexanol using 50%
nitric acid in presence of catalyst ammonium metavanadate.
CHEMICALS REQUIRED:
Cyclohexanol, Concentrated nitric acid, Ammonium metavanadate.
APPARATUS:
Conical flask, Thermometer, Beaker, Funnel, Measuring cylinder, Filter
paper.
PROCEDURE:
CPP-1.5 (1.1) Practical Organic Chemistry
DOS & R in Organic Chemistry, TUT Page 3
 In a 250 mL round bottom flask or conical flask 15 mL of 50%
HNO3 was placed and the acid solution was heated on water bath
nearly to 65-70oC.
 A pinch of ammonium metavanadate (~0.05 g) was added to hot
acid solution.
 1 mL of cyclohexanol was added dropwise to the acid solution
maintaining the temperature at 65-70oC.
 The reaction progress was indicated by the evolution of brown gas
i.e. oxides of nitrogen.
 After complete addition of cyclohexanol, maintain the temperature
for 10 more minutes till evolution of brown gas ceases.
 The reaction mixture was cooled to lab temperature and was then
placed in an ice bath. Crystallization of Adipic acid takes place as
light yellow/white crystals.
 The light yellow/white crystals were then collected by filtration
and washed with cold 50% HNO3. (Do not wash with excess)
 The light yellow/white crystals were then dried and weighed.
Calculate the yield and obtain melting point.
REACTION:
OH
COOH
COOH50 % HNO3
Cat. NH4VO3
65-70o
C
CALCULATIONS:
CPP-1.5 (1.1) Practical Organic Chemistry
DOS & R in Organic Chemistry, TUT Page 4
Compound Amount
Molecular
Weight
Moles Equivalent
Cyclohexanol 1 mL
100.1
D = 0.96 g/cm3
- -
50 % HNO3 15 mL - - -
NH4VO3
Pinch
(~0.05g)
- - -
THEORETICAL CALCULATION:
100.1 g of cyclohexanol gives 146.14 g of Adipic acid
1 g of cyclohexanol will forms X g of Adipic acid
Theoretical yield =
Practical yield =
% Yield = (Practical yield) / (Theoretical yield) X 100
CHEMICAL TESTS:
Reaction with NaHCO3
Cyclohexanol: No evolution of gas (-Ve)
Adipic Acid: Evolution of gas (+Ve)
Litmus test:
Cyclohexanol: Blue litmus remain to blue and red litmus remain to red
(Neutral)
Adipic Acid: Blue litmus remain turns to red and red litmus remain to
red (Acidic)
CPP-1.5 (1.1) Practical Organic Chemistry
DOS & R in Organic Chemistry, TUT Page 5
MECHANISM:
OH
50 % HNO3
OH2
NO3
-H2O
O
N
O
O
H
O
HNO2 HNOH2O
OHO
N
O
NOH
O
O
COOH
COOHVO3
H2O
Keto-Enol tautomerism
H
O
-HNO2
Oxidation
CPP-1.5 (1.1) Practical Organic Chemistry
DOS & R in Organic Chemistry, TUT Page 6
REPORT:
Structure
and name
of the
compound
Theoretical
yield
Practical
yield
Percentage
yield
Theoretical
Melting
point
Experimental
Melting
point
COOH
COOH
Adipic acid
152oC
REFERENCES:
1. https://www.scribd.com/doc/114328909/Oxidation-of-
Cyclohexanol-to-Adipic-Acid.
2. Organic Syntheses, Coll. Vol. 1, p.18 (1941); Vol. 5, p.9 (1925).
3. https://www.academia.edu/31380866/PREPARATION_OF_ADIP
IC_ACID_FROM_CYCLOHEXENE_Chem_126_4.doc.

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Oxidation of cyclohexanol or preparation of adipic acid

  • 1. CPP-1.5 (1.1) Practical Organic Chemistry DOS & R in Organic Chemistry, TUT Page 1 Prepared By Dr. Krishnaswamy G Faculty DOS & R in Organic Chemistry Tumkur University Tumakuru
  • 2. CPP-1.5 (1.1) Practical Organic Chemistry DOS & R in Organic Chemistry, TUT Page 2 Oxidation of Cyclohexanol or Preparation of Adipic acid from cyclohexanol AIM: To prepare Adipic acid from cyclohexanol by oxidation. PRINCIPLE: Adipic acid is a dicarboxylic acid with IUPAC name Hexane-1,6-dioic acid with the formula (CH2)4(COOH)2. Fromm an industrial perspective, it is the most important dicarboxylic acid used as monomer for the production of nylon by polycondensation reaction with hexamethylene diamine forming 6, 6,-nylon. Hence, the purpose of this experiment is to synthesize Adipic acid through oxidation of cyclohexanol using 50% nitric acid in presence of catalyst ammonium metavanadate. CHEMICALS REQUIRED: Cyclohexanol, Concentrated nitric acid, Ammonium metavanadate. APPARATUS: Conical flask, Thermometer, Beaker, Funnel, Measuring cylinder, Filter paper. PROCEDURE:
  • 3. CPP-1.5 (1.1) Practical Organic Chemistry DOS & R in Organic Chemistry, TUT Page 3  In a 250 mL round bottom flask or conical flask 15 mL of 50% HNO3 was placed and the acid solution was heated on water bath nearly to 65-70oC.  A pinch of ammonium metavanadate (~0.05 g) was added to hot acid solution.  1 mL of cyclohexanol was added dropwise to the acid solution maintaining the temperature at 65-70oC.  The reaction progress was indicated by the evolution of brown gas i.e. oxides of nitrogen.  After complete addition of cyclohexanol, maintain the temperature for 10 more minutes till evolution of brown gas ceases.  The reaction mixture was cooled to lab temperature and was then placed in an ice bath. Crystallization of Adipic acid takes place as light yellow/white crystals.  The light yellow/white crystals were then collected by filtration and washed with cold 50% HNO3. (Do not wash with excess)  The light yellow/white crystals were then dried and weighed. Calculate the yield and obtain melting point. REACTION: OH COOH COOH50 % HNO3 Cat. NH4VO3 65-70o C CALCULATIONS:
  • 4. CPP-1.5 (1.1) Practical Organic Chemistry DOS & R in Organic Chemistry, TUT Page 4 Compound Amount Molecular Weight Moles Equivalent Cyclohexanol 1 mL 100.1 D = 0.96 g/cm3 - - 50 % HNO3 15 mL - - - NH4VO3 Pinch (~0.05g) - - - THEORETICAL CALCULATION: 100.1 g of cyclohexanol gives 146.14 g of Adipic acid 1 g of cyclohexanol will forms X g of Adipic acid Theoretical yield = Practical yield = % Yield = (Practical yield) / (Theoretical yield) X 100 CHEMICAL TESTS: Reaction with NaHCO3 Cyclohexanol: No evolution of gas (-Ve) Adipic Acid: Evolution of gas (+Ve) Litmus test: Cyclohexanol: Blue litmus remain to blue and red litmus remain to red (Neutral) Adipic Acid: Blue litmus remain turns to red and red litmus remain to red (Acidic)
  • 5. CPP-1.5 (1.1) Practical Organic Chemistry DOS & R in Organic Chemistry, TUT Page 5 MECHANISM: OH 50 % HNO3 OH2 NO3 -H2O O N O O H O HNO2 HNOH2O OHO N O NOH O O COOH COOHVO3 H2O Keto-Enol tautomerism H O -HNO2 Oxidation
  • 6. CPP-1.5 (1.1) Practical Organic Chemistry DOS & R in Organic Chemistry, TUT Page 6 REPORT: Structure and name of the compound Theoretical yield Practical yield Percentage yield Theoretical Melting point Experimental Melting point COOH COOH Adipic acid 152oC REFERENCES: 1. https://www.scribd.com/doc/114328909/Oxidation-of- Cyclohexanol-to-Adipic-Acid. 2. Organic Syntheses, Coll. Vol. 1, p.18 (1941); Vol. 5, p.9 (1925). 3. https://www.academia.edu/31380866/PREPARATION_OF_ADIP IC_ACID_FROM_CYCLOHEXENE_Chem_126_4.doc.