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02 Methodology
1
Introduction Background of Phenol
Aromatic organic compound with
hydroxyl (-OH) group attached to
Colorless liquids or white an aromatic ring.
solids at room temperature.
2
Introduction Background of problems
4
Introduction Scope of work
1. Using Aspen Plus ver. 9.0 to simulate
the phenol production process.
Objectives
2. Sizing and costing all of the major
1. To design and compared a equipments in this process.
phenol production processes
from alternative way between 3. The purity of phenol product will be
cumene and toluene. at least 99.00 % by weight.
6
Simulation & Result Process flow diagram: Phenol production from cumene
17
Cumene
Acetone
Cumene Hydroperoxide Oxygen Phenol
1 3 15
5 Cumene 19
Condenser
2
4
Air
Plug Flow Reactor
Heater
Flash Drum
14
13
6
16 18
20
Sulphuric acid 8 9
7 Acetophenone
17
Cu mene Recycle Cumene
Fresh Cumene 1
2 Mixer 3
Oxygen To 1st reactor
Air
8
Simulation & Result Process flow diagram: Reactor Section
17
Cumene
Acetone
Cumene Hydroperoxide Oxygen Phenol
1 3 15
5 Cumene 19
2
Condenser
4
Air
Plug Flow Reactor
Heater
Flash Drum
14
13
6
16 18
20
Sulphuric acid 8 9
7 Acetophenone
Purge
9
Simulation & Result Reactor section : 1st reactor (Plug flow)
3 4
Stream S3 S4
Temperature (°C) 39.68 40
Pressure (bar) 6 6 Plug Flow Reactor
Flow rate Mass
Component Unit RPLUG
(kg/hr) Fraction
Oxygen 14,399 1,003 0.015 Temperature (°C) 40
Cumene 52,371 2,054 0.03 Pressure (bar) 6
Cumene Hydroperoxide 0 63,736 0.95
Cumene + O2 Cumene Hydroperoxide
k 0.35
Ea (kcal/mol) 19.35
Chen E.C.M.(1980)
10
Simulation & Result Reactor section : Before enter CSTR
11
Simulation & Result Reactor section : 2nd reactor (CSTR)
Cumene
Acetone
Cumene Hydroperoxide Oxygen Phenol
1 3 15
5 Cumene 19
2
Condenser
4
Air
Plug Flow Reactor
Heater
Flash Drum
14
13
6
16 18
20
Sulphuric acid 8 9
7 Acetophenone
Separation section
Recycle acid
12
10
11
Purge
13
Simulation & Result Separation section
Phenol Purity 53 %
Stream S10 S13 Unit Flash Drum
Crude phenol
Temperature (°C) 185 185 Temperature (°C) 185
Pressure (bar) 1 1
Pressure (bar) 1 13
Flow rate (kg/hr)
Cumene 104.86 1926.3
CHP 17.77 245.84
Sulfuric Acid 6,606.8 805
Phenol 4,610.7 35,400 From CSTR 9
Acetone 248.62 22,500
Acetophenone 1,303.8 3,753.4 Flash drum
Alpha Methyl Styrene 16.5 209.5 Flash Drum
DMBA 17.1 29.72 Recycle acid
Methanol 6.59 1,059.4 12
10
11
Splitter
Purge
Split fraction (Purge) 0.175
14
Simulation & Result Process flow diagram: Purification Section
17
Cumene
Acetone
Cumene Hydroperoxide Oxygen Phenol
1 3 15
5 Cumene 19
2
Condenser
4
Air
Plug Flow Reactor
Heater
Flash Drum
14
13
6
16 18
20
Sulphuric acid 8 9
7 Acetophenone
Purge
15
Simulation & Result Purification section – 1st distillation
Recycle Cumene
17
Stream S14 S15 S16 Acetone
15
Acetone Phenol
Temperature (°C) 60 55.20 177.30 Purity 95 % 19
Condenser
Pressure (bar) 1 1 1
Flow rate (kg/hr) Heater
Crude
Oxygen 59.3 59.3 0 14 1
phenol
Cumene 1,926.3 1.36 1,925
CHP 245.84 0 245.84 16 18
Acetophenone
Acetophenone 3,753.4 0 3,753.4
Alpha Methyl Unit RADFRAC2
209.5 180.5 29
Styrene
Stage 16
Feed stage 9
Reflux ratio 7.10
Distillate to feed ratio 0.06
17
Simulation & Result Purification section – 3rd distillation
Recycle Cumene
17
Stream S18 S19 S20 Phenol Purity 99 %
Acetone
Phenol
Temperature 15
184.59 182.28 210.03 19
(°C) Condenser
Pressure
1 1 1
(bar) Heater
Flow rate (kg/hr) Crude 14
Cumene 30.16 30.16 0 phenol 3
CHP 223.56 223.56 0
Sulfuric Acid 805 0 805 16 18
Unit RADFRAC3
Stage 20
Feed stage 7
Reflux ratio 1.83
Distillate to feed ratio 0.89
18
Simulation & Result Toluene oxidation process
Crystallizer section
1st Reaction
Oxidation
to Benzoic acid
2nd Reaction
Oxidation of
Benzoic acid to
phenol
19
Simulation & Result Toluene oxidation process
Toluene distillation
system
16 v Water
From reactor 15 T-202
system
To the
nd
2 reactor
20
Simulation & Result Toluene oxidation process
Simulation model from Aspen V.9
21
Simulation & Result Toluene oxidation process
Process Flow Diagram
Purge
Purge 31
31 Recycle Toluene
29
29
Recycle Toluene E-204
30
D-203
E-204
Feed preparation
12 D-203
T-201 system
30 E-203
E-205
Oxygen 3 4 5 6
E-202
11 D-202 12
13
T-201 Reactor system
E-201
Toluene 1
2
7
E-203
R-201 E-205
Oxygen 3
P-201
4 5 6
E-202
D-201 10 14
Separation and
11 D-202 16 v Water
Purification system
v
9
13
T-202
Water 8 E-201 15
17
2 V-201
7
Toluene 1 C-201
R-201
E-209
P-201 v Vent gas
D-201
25
10 14
D-205 18
v
Phenol 28
v
9
26
E-207 V-202 E-206
Water 8
15 T-202
R-201
17
Benzoic E-208 V-201
acid
Purge 31 29
Recycle Toluene
C-201 E-204
30 E-209 D-203
12 T-201
E-203
Oxygen 3 4 5 6
E-202 25 E-205
v Vent gas
D-202
D-205
11
13
E-201
2
7
18
Toluene 1
v R-201
Phenol P-201 28
D-201 10 14
T-203 D-204 24 23 22 21 20 16 19 v
v
Oxygen
Water
v
9
Water 8
15 T-202
17
V-201
26
E-207 V-202 E-206
C-201
E-209
D-205
25
R-201 18
v Ve nt gas
v
Phenol 28
22
T-203 D-204 24 23 22 21 20 19 v Oxy gen
Benzoic E-208 26
E-207 V-202
R-201
E-206
acid
Benzoic
acid
E-208
Simulation & Result Toluene oxidation process
1. Oxidation of toluene to form benzoic acid section From toluene
recycle stream
Feed preparation system
30
P-201
Table 1 The values of the rate constants and activation energies of the
Stream 6 Mass flow %wt T(°C),P(bar)
kinetic reactions at 155 °C and 10 bar. (PINGHUA TAN et al, 2010)
(kg/hr)
Equation k, (min-1) Ea, kJ/mol Toluene 30,100 24.13
4.1 0.0016 69.54 Oxygen 464 0.37
4.2 0.126 66.84
Benzoic Acid 80,991 64.94
4.3 0.001169 123.91 155,10
4.4 0.135 81.27 Water 12,079 9.68
Benzaldehyde 774 0.62
Ref : Kinetic Models for Liquid-Phase Catalytic Oxidation of Toluene to Benzoic Acid with
Benzyl Alcohol 307 0.25
24
Pure Oxygen, PINGHUA TAN et al, 2010
Simulation & Result Toluene oxidation process
1. Oxidation of toluene to form benzoic acid section
Phase separation system
12
Distillation Unit D-202
system
T (°C) 283
P(bar) 1
From the E-202
1st reactor 11 D-202
13
D-201 10 14
9 16 v Water
v
Water 8 15 T-202
V-201
Unit T-202
Unit D-201 T (°C) 263
To the
T (°C) 30 nd
2 reactor P(bar) 1
P(bar) 10
25
Simulation & Result Toluene oxidation process
1. Oxidation of toluene to form benzoic acid section
Phase separation system
Unit D-201
T (°C) 30
Distillation
12
system P(bar) 10
%Water removal 70
From the E-202
1st reactor 11 D-202
Stream7 Mass flow : kg/hr T(°C),P(bar)
7
Oxygen 464
9 16 v Water Water 12,079
v
Water 8 15 T-202
Benzoic Acid 80,991
V-201
Benzaldehyde 774
To the Benzyl Alcohol 307
2nd reactor
26
Simulation & Result Toluene oxidation process
1. Oxidation of toluene to form benzoic acid section
Distillation
12
Phase separation system Stream8 Mass flow : kg/hr T(°C),P(bar)
system
Toluene 4 30,10
E-202 Oxygen 105
From the
Water 8342
1st reactor 11 D-202
Benzoic Acid 423
7
Benzaldehyde 179
Benzyl Alcohol 0
D-201 10 14
Stream9 Mass flow : kg/hr T(°C), P(bar)
Toluene 30096 30,10
9 16 v Water
v Oxygen 359
Water 8 15 T-202
Water 3737
V-201 Benzoic Acid 80568
Benzaldehyde 595
To the Benzyl Alcohol 307
nd
2 reactor
27
Simulation & Result Toluene oxidation process
1. Oxidation of toluene to form benzoic acid section
Phase separation system Unit D-202
T (°C) 283
P(bar) 1
12
Distillation
system Vapor Fraction 0.8
From the E-202
1st reactor D-202 Mass flow : T(°C),
11
Stream 11
kg/hr P(bar)
7
13 Toluene 30096
D-201 10 14
Oxygen 359
9 16 v Water Water 3737
v
Water 8 15 T-202
V-201
Benzoic Acid 80568 283,1
7
13
Stream 14 Mass flow : T(°C),P(bar)
D-201 10 14 kg/hr
From
separation 12 T-201 Stream 12 Mass flow : kg/hr
system Toluene 30,025
E-205 Oxygen 358
Water 827
To
separator 13
Benzoic Acid 61,111
T-202 Benzaldehyde 578
Benzyl Alcohol 299
30
Simulation & Result Toluene oxidation process
1. Oxidation of toluene to form benzoic acid section Stream 13 Mass flow : kg/hr
Toluene purification system Toluene 1
Oxygen 0
To toluene
mixer
29
Water 817
Recycle Toluene
Benzoic Acid 57,871
E-204
Benzaldehyde 7
D-203 Benzyl Alcohol 34
From
separation 12 T-201 Stream 29 Mass flow : kg/hr
system Toluene 30,025
E-205 Oxygen 358
Water 9
To
Benzoic Acid 3,240
separator 13
T-202 Benzaldehyde 571
31
Simulation & Result Toluene oxidation process
1. Oxidation of toluene to form benzoic acid section
Phase separation system
Unit T-202
T (°C) 263
12
Distillation P(bar) 1
system
%Water removal 99
7
Toluene 71
Oxygen 0
D-201 10 14
Water 3,728
v
263,1
9 16
Water Benzoic Acid 77,327
v
Water 8 15 T-202
17
Benzaldehyde 24
V-201
Benzyl Alcohol 43
To the
2nd reactor
32
Simulation & Result Toluene oxidation process
1. Oxidation of toluene to form benzoic acid section
Stream16 Mass flow : kg/hr T(°C),P(bar)
Phase separation system
Toluene 0
12
Distillation Oxygen 0
system
Water 3691 263,1
E-202 Benzoic Acid 0
From the
1st reactor 11 D-202 Benzaldehyde 0
13
Benzyl Alcohol 0
7
Toluene 71
9 16 v Water
v
8 15 T-202
Oxygen 0
Water
17 Water 37 263,1
V-201
Benzoic Acid 77,327
To the Benzaldehyde 24
2nd reactor
Benzyl Alcohol 43 33
Simulation & Result Toluene oxidation process
2. Oxidation of benzoic acid to phenol section
Feed preparation system
34
Simulation & Result Toluene oxidation process
2. Oxidation of benzoic acid to phenol section Unit R-201
Reactor system T (°C) 221
Benzoic acid P(bar) 10
from separator Volume (m3) 520
(1st oxidation section)
Stream21 Stream22
Catalyst : cupric benzoate catalyst
18 T(°C) 221 221
P(bar) 10 10
To separation 22 21 20 19 v Oxygen
system Mass flow(kg/hr) 91102 91102
E-206
Toluene 71 71
R-201
Oxygen 13600 7665
Water 37 37
Table 2 The values of the rate constants and activation energies of Benzoic Acid 77,327 32,031
the kinetic reactions at 221 °C and 10 bar. ( M. STOLCOVA and et
al,1986) Benzaldehyde 24 24
Benzyl Alcohol 43 43
Equation k, (min-1) Ea, kJ/mol
4.5 0.124 69 Phenol 0 34907
Carbon dioxide 0 16324
Ref : Oxidation of Benzoic Acid to Phenol in the Vapor Phase, M. STOLCOVA et al, 1986
35
Simulation & Result Toluene oxidation process
2. Oxidation of benzoic acid to phenol section Vent gas
25 v
Phase separation system
To Distillation From
D-204 24 23
2nd reactor
system
V-202
26 E-207
Benzoic v E-208
Toluene 33 acid
27
Water 0 Toluene 0
Oxygen 0
Benzoic Acid 1500
Water 21
Benzaldehyde 24 Benzoic Acid 30512
Benzyl Alcohol 43 Benzaldehyde 0
Benzyl Alcohol 1
Phenol 34214
Phenol 7
Carbon dioxide 88 39
Carbon dioxide 0
Simulation & Result Comparison of two alternatives
phenol production processes
40
Simulation & Result Work Plan
June July August
Project plan Week 2 Week 3 Week 4 Week 1 Week 2 Week 3 Week 4 Week 1
Problem Understanding
- Problem Definition
- Process Description
- Work Plan and Strategy
Process Simulation
- Flow Synthesis
- Mass & Energy balance
- Design of Unit Operation
Equipment Design
- Equipment Sizing
- Costing
Economic Evaluation
- Cash Flow Analysis
- Complete Final Report
41
Thank you
42