Clean synthesis of adipic acid using

optimized condition
Registration No. 2016-MS-CH-38
Contents
 Problem statement
 Objective
 Introduction
 Literature survey
 Experimentation
 Results and discussion
Problem Statement
 In Pakistan according to import data millions kg of adipic
acid has been imported in Pakistan last year therefore it
should be synthesis in Pakistan to improve the economy of
Pakistan.
 Current methods of adipic acid production units using nitric
acid as oxidant which produce 0.3kg of N2O per kg of adipic
acid. Therefore clean synthesis of adipic acid should be
consider.
Objectives
 To Select the clean, low cost and easily available chemicals to
make process clean and cost effective
 To find the optimized value of reactants and process
conditions to obtain maximize yield
 Determination of melting point, FTIR and physical
properties of adipic acid for the characterization of adipic
acid
Introduction
Introduction
 Adipic acid is the main ingredient for nylon-6,6. Adipic acid has its wide
application range in production of polyester and polyurethane resins and as an
additive in cosmetics, gelatins, fertilizers, adhesives, paper and waxes
 Global application share

Others
11%
Adipate Esters
14%
Polyamide6,6
54%
Polyurethane
21%
 Types of Adipic acid
 On the basis of manufacturing adipic acid is divided into two
types
 Bio based adipic acid
 Synthetic adipic acid
Global Production capacity of adipic acid
(2015)
Company Production Capacity
(Thousand tons)
Invista 684
Rhodia 608
Ascend 494
BASF 418
Lioyang Petrochemical 266

Ridici 228
Shandong Hongye 228
Asahi Kasei 190
Others 684
Total 3800
Literature survey
Literature survey
 Detailed literature survey.xlsx
 Basic Information Raw Material Tem. Total Conclusion
Pres. oC
Yield %
Time
Year Paper Title Base Material Oxidant Catalyst Remarks

1991
`
Synthesis Of Adipic Acid Via The Nitric Acid
Oxidation Of Cyclohexanol In A Two Step Batch
Process Cyclohexanol HNO3 Vanadium 1atm 95 22Hr 98 Highest Yield

Clean synthesis of adipic acid by direct oxidation of Sodium Environment

1999 cyclohexene with H2O2 over peroxytungstate Cyclohexene H2O2 tungstate 1atm 95 20Hr 95 Friendly

Time efficient
reaction &
Green Catalytic Oxidation of Cyclohexanone to Environment
2003 Adipic Acid Cyclohexanone H2O2 H2WO4 1atm 90 20Hr 91 friendly

Influence of reaction conditions on product Optimized

distribution of cyclohexene to adipic acid with Sodium processing
2011 hydrogen peroxide Cyclohexene H2O2 tungstate 1atm 80 7Hr 90.7 conditions

Dual catalytic function of the task-specific ionic

liquid: Green oxidation of cyclohexene to adipic acid Various In complete and
2013 using 30% H2O2 Cyclohexene H2O2 Catalyst 1atm 85 20Hr 85 expensive method

Hydrothermal synthesisofWO3 nano rods and their WO3 nano Environment

2014 performance in the adsorption of Rhodamine Cyclohexene H2O2 rods 1atm 90 24Hr 79 Friendly

Environment
Dawson-type polyoxometalates as green catalysts for Polyoxo friendly
2016 adipic acid synthesis Cyclohexene H2O2 metalates 1atm 90 12Hr 69 -

Conversion of cyclohexanone to adipic acid H2O2 Heteropoly

2016 catalyzed by heteropoly compounds Cyclohexanone compounds 1atm 100 24Hr 48 Not effective
Material and Methodology
Materials
 Cyclohexanone
 30% H2O2
 sodium tungstate dehydrate
 Sulfuric acid
 Sodium bisulfate
Experimental Setup
Flow Chart
Result and Discussion
 Characterization
 FTIR
99 100
94 95 96 97 98
Transmittance [%]
93
92

2951.18
2875.11

2658.33

1680.18

1460.04
1407.62
1358.07
1270.12
1184.63

1042.62

909.39

730.80
679.13
3500 3000 2500 2000 1500 1000
Wavenumber cm-1

D:\SYED ISRAR(CHEMICAL MSC)\MEAS\Sample = 002(a) Adipic Acid.0 Sample = 002(a) Adipic Acid Instrument type and / or accessory
08/12/2017

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Characterization
 The main group for the identification of adipic acid is
carbonyl group c=o stretch is between (1670-1820) ,O-H
stretch is between (2500-3300 ) and C-O stretch is (1210-
1320) show all the peaks in the graph and confirm the
identification of adipic acid.
Characterization
 Melting Point
 Theoretical melting point 148-152oC
 Actual melting point 149oC
 Characterization
 Physical properties:

Property Standard Value Sample Value

Color White White
Melting point 148-152 °C 149°C
Smell Odorless Odorless
Crystalline
Physicality Crystalline Powder
Powder
State Solid Solid
Optimization of reaction
 Factors which effect adipic acid yield
 Temperature
 Time
 Catalyst amount
 H2O2 molar ratio
 Molarity of acid
 Concentration of H2O2
Optimization of reaction
 Effect of temperature on yield
 Reaction Condition
 Molarity acid: 0.3M, H2O2: catalyst (218:1), Time: 8hr, Cyclohexanone: H2O2
1:4.5

60
50
40
Yield

30
20
10
0
60 70 80 90 100 110
Temperature (oC)
Optimization of reaction
 Effect of time on reaction
 Reaction Condition
 Morality (0.3M), H2O2: catalyst (218:1), Temperature 90oC,Cyclohexanone:
H2O2 (1:4.5)

80
Conversion %

70
60
50
40
30
20
10
0
0 5 10 15 20 25 30

Time (Hr)
Optimization of reaction
 Effect of Catalyst amount
 Reaction Condition
 Molarity acid 0.3M, Cyclohexanone: H2O2 (1:4.5) Temperature 90oC, Time
8hr

60

50
Conversion

40

30

20

10

0
0.3 0.5 0.7 0.9 1.1 1.3 1.5 1.7
Catalyst molar ratio with 218 moles
H2O2
Optimization of reaction
 Effect of molar ratio of H2O2 on reaction
 Reaction Condition
 Molarity of acid 0.3M, H2O2: catalyst (218:1), Temperature 90oC, Time 8hr

60
50
Conversion

40
30
20
10
0
3 3.5 4 4.5 5

Hydrogen peroxide molar ratio with cyclohexanone

Optimization of reaction
 Effect of molarity of acid on reaction
 Reaction Condition
 H2O2: catalyst (218:1), Time 8hr, Temperature 90oC Cyclohexanone: H2O2
(1:4.5)
60

50
Adipic Acid Yield

40

30

20

10

0
0 0.05 0.1 0.15 0.2 0.25 0.3 0.35 0.4 0.45
Sulfuric acid Molarity
Optimization of reaction
 Effect of concentration of H2O2 on reaction
Conclusion & Recommendation
Conclusion and Recommendation
 After optimizing reaction parameter we conclude that the
maximum yield we can obtain from reaction is 69%.
Conclusion and Recommendation
 To make reaction clean and cost effective we should
follow following rules
 Prevent or minimize the waste of work instead to treat at the end of life
 Minimize the number of reactants in a reaction
 Use clean chemicals to minimize the emission of dangerous gases
 Maximum produce desired product and non toxic material
 Use clean catalytic reactions rather
 Minimize the Use of solvents and auxiliary reagents or use less toxic
compounds
 Optimize the energy efficiency of processes
 Use as much as possible renewable raw materials
 Product must decompose at the end of the life into non toxic elements
 Maximize the control of chemical processes
Thank You