Phenol and acetone from cumene process [108-95-2]

CONTENTS OF FACTORY GATE TO FACTORY GATE

LIFE CYCLE INVENTORY SUMMARY

Chemistry
Process Summary
Summary of LCI Information
Process Diagram Interpretation Sheet
Process Diagram or Boundary of LCI
Mass Balance of Chemicals in each Process Stream (Highlighting Chemicals that are Wastes and the
Physical State when Lost)
Graph of Cumulative Chemical Losses through Manufacturing Process
Graph of Cumulative Non-Contaminated Water Use/Emission through Manufacturing Process
Energy Input for each Unit Process, Cumulative Energy Requirements, Cooling Requirements
(exotherms), and Assumed Heat Recovery from Hot Streams Receiving Cooling
Graph of Cumulative Energy Requirements

Authors C.J. Gonzalez and Y. Li

Peer reviews, name (date) MR Overcash (3-3-2000); MR Overcash (2-6-2008)
Gtg report last modified on 10-4-2010
Additional notes

Checked for database consistency on 10-4-2010

First gtg version finalized on 3-3-2000
Modification history, Author (date) EMG (10-4-2010), YL (2-6-2008), and CJG (3-3-2000)

Products Phenol, Acetone

Standard inputs Benzene, Oxygen, Propylene

Methodology: Environmental Clarity gtg lci reports are based on industrial practice information, standard
methods of engineering process design, and technical reviews. These reports are intended to be
representative of industrial production based on the stated route.
Terms of use: Environmental Clarity does not assume any liability due to use of these lci data. Integration
of these data with lci data based on other methodologies is the responsibility of the user. Each report may
be updated to improve model accuracy or representativeness.
Users of this report should cite: E. Griffing and M. Overcash, Chemical Life Cycle Database,
www.environmentalclarity.com, 1999 - present.

CHEMISTRY:
H3PO4 O2 H2SO4
C6H6 + C3H6 C9H12 C9H12O2 C6H6O + C3H6O
Benzene Propylene Cumene Cumene Hydroperoxide Phenol Acetone

updated on 10/4/2010 1
Griffing and Overcash, Chemical Life Cycle Database, www.environmentalclarity.com, 1999-present.
PROCESS:
The first step of the process is the alkylation of benzene. Chemical or refinery-
grade propylene is added to benzene and reacted at 230 C and 500 psig using 1% by
mass phosphoric acid as a catalyst. Cumene is yielded in this process and is then sent to
the oxidizer where it is mixed with oxygen. This oxidation reaction produces cumene
hydroperoxide at 110 C and 80 psig. Cumene hydroperoxide in the presence of sulfuric
acid is converted to acetone and phenol at the acidifier. Phenol is purified by a centrifugal
separator.

updated on 10/4/2010 2
Griffing and Overcash, Chemical Life Cycle Database, www.environmentalclarity.com, 1999-present.
SUMMARY OF LCI INFORMATION
Product: Phenol
Basis: 1,000 kg/hr phenol
Reference: CHE 450 Report on phenol, Fall 1998
Ullmanns, Encyclopedia of industry chemistry
Faith, Keyes, and Clark's Industrial chemicals. New York : Wiley,
[1975]
Encyclopedia of Chemical Technology, Kirk and Othmer, New
York : Wiley, [1992]
Plant Location:
Comments: All mass and energy units per hour are equivalent to per 1,000 kg
of phenol

This LCI summary data has been updated by Yong on 02-06-2008. Fugitive emission
makeups are added to the input chemicals. Unknown organic waste from original lci
report is assumed to be Acetophenone because it's the main organic waste from the
process. Inorganic waste is neglected because inorganic acids input are negligible.
Standard inputs
UID Name Flow Purity Units Comments
71-43-2 Benzene 919 - [kg/hr]
7782-44-7 Oxygen 387 - [kg/hr]
115-07-1 Propylene 493 - [kg/hr]
Total 1799 [kg/hr]
Non-reacting inputs
UID Name Flow Purity Units Comments
7732-18-5 Water 48.0 - [kg/hr]
Total 48.0 [kg/hr]
Ancillary inputs
UID Name Flow Purity Units Comments
7664-38-2 Phosphoric 0.700 - [kg/hr]
acid
7664-93-9 Sulfuric acid 0.800 - [kg/hr]
Total 1.50 [kg/hr]
Products
UID Name Flow Purity Units Comments
108-95-2 Phenol 1000 99.9 [kg/hr]
67-64-1 Acetone 623 99.0 [kg/hr]
Total 1623 [kg/hr]
Benign outflows
UID Name Flow Purity Units Comments
7732-18-5 Water 48.0 - [kg/hr]
Total 48.0 [kg/hr]

updated on 10/4/2010 3
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Process emissions
UID Name Gas Liquid Solid Solvent Units Comments
98-83-9 alpha- 5.00 0 0 0 [kg/hr]
Methylstyrene
67-64-1 Acetone 12.5 0 0 0 [kg/hr]
98-86-2 Acetophenone 0 151 0 0 [kg/hr]
71-43-2 Benzene 9.00 0 0 0 [kg/hr]
98-82-8 Cumene 27.0 0 0 0 [kg/hr]
80-15-9 Cumene 10.0 0 0 0 [kg/hr]
Hydroperoxide
108-95-2 Phenol 5.00 10.0 0 0 [kg/hr]
115-07-1 Propylene 2.50 0 0 0 [kg/hr]
Total 71.0 161 0 0

Mass balance
Total inputs 1849
Total outflows 1903
Net input -54.5

Energy use
Energy type Amount Units Comments
electricity 1588 [MJ/hr] Net electricity use at
plant
heating steam 7439 [MJ/hr] heating by steam
(0.85 efficiency
included)
Net input 9028 [MJ/hr] Net of energies
requirement input to system
cooling water - 1.48E+04 [MJ/hr] net cooling by
cooling water
potential recovery -4390 [MJ/hr] potential energy
recovery (negative)
Net energy 4638 [MJ/hr] Net input
requirement -
potential recovery

updated on 10/4/2010 4
Griffing and Overcash, Chemical Life Cycle Database, www.environmentalclarity.com, 1999-present.
PROCESS DIAGRAM INTERPRETATION SHEET

1) As much as possible, standard symbols are used for all unit processes.

2) Only overall input and output chemicals are labeled on these diagrams. All
intermediate information is given on the attached Process Mass Balance sheet

3) The physical state of most streams is shown (gas, g; liquid, l; solid, s)

4) The process numbering is as follows,

generally numbers progress from the start to the end of the process
numbers are used for process streams
C i , i = 1,..n are used for all cooling non-contact streams
S j, j = 1,...n are used for all steam heating non-contact streams
5) Recycle streams are shown with dotted lines

6) For most streams, the temperature and pressure are shown, if the pressures are greater
than 1 atm

updated on 10/4/2010 5
Griffing and Overcash, Chemical Life Cycle Database, www.environmentalclarity.com, 1999-present.
PROCESS DIAGRAM
Phosphoric Acid 1.0 kg/hr Propylene 490 kg/hr
2(l) 5(l) 3(g) 20C
20C 6(g)
Compressor A

Pump A
4(l)
Mixer A
Pump B 9(l) 97C

1(l)
7(l)
20C
20C
Benzene
8(l) 20C
910 kg/hr

S2
Pump C 130C Compressor B
Heat Exchanger 13(l)
230C
1 atm 11(l)
14(l) Benzene Alkylation Reactor 265C
128C 15(l)
500 psig
18.2 kg/hr C3 C24
Pump D 50C C22 230C 50C
Hydrogen
20C
20(g) 20C C23
Cooler A
C2 Pump M
C25
20C 16(l)
20C Compressor C
110C 12(l)
C1 Turbine A 230C
Pump E
21(g) 20C 500 psig
17(l)
Pump F 110C
C26
20C Hydrogenator
Centrifugal Phosphoric Acid Recycle
Separator A
19(l) 18(l) 110C
23(g) C27 110C
Pump O
110C 50C
22(l) 152C
Compressor D
A 24(g) 276C 80 psig B

updated on 10/4/2010 7
Griffing and Overcash, Chemical Life Cycle Database, www.environmentalclarity.com, 1999-present.
 A Oxygen 387 kg/hr
24(l)
25(g) 20C
C28 C29 276C B
20C 20C 26(g) Compressor E
127C
Oxidizer
Pump P 80 psig
28(l) C30
110C 50C
27(l)
Turbine B 110C
Washer 29a (l) Water 48 kg/hr
C6
50C S2
29(s/l) Salt 24 kg/hr
130 C
Water 48 kg/hr 1,000 kg/hr
0.8 kg/hr
30(l) Sulfuric Acid Phenol
32(l) 80C 34(l)
110C 35(l) 80C 99.9%
Cooler B 33(l) 20C 45(l)
31(l) Preheater A
Pump I Cumene Recycle 20C
Pump G
38(l) S1 22(l)
C5 130 C Acetone 623 kg/hr
80C 152C
C4 20C 99%
C33 C20 Phenol C21
20C 50C 46(l) 20C 50C
Acidifier C17 C18 C19 Cooler
C16 20C 20C 50C 20C
20C
Pump H C32
Pump J Acetone Cooler Pump L
20C C12 C15 44(l)
Pump K C9 C11 C13 C14
C31 50C 181C
36(l) 50C 50C
20C C8 C10 20C 20C 20C
C7
Pump Q 80C 20C 20C
20C
37(l) Conden C
Conden A Conden B
Pump R 41(l) Pump S Pump T
Centrifugal
10(l) 56C 56C
Separator
Waste Product
40(l) 42(l)
39(l) Acetophenone
56C 152C
80C C36 S7 43(l)
50C S5
S3 130C 181C
C35 130C 130C S6
C34 S4 161 kg/hr
20C 20C 130C S8 0.46 Acet
Acetone 130C Cumene Finishing Column
Cooler C
Distillation Column Distillation Column 130C 0.46 Byprod
0.08 Phenol
Pump N

updated on 10/4/2010 8
Griffing and Overcash, Chemical Life Cycle Database, www.environmentalclarity.com, 1999-present.
 Mass Balance of Chemicals in each Process Stream Mass Balance of Chemicals in each Process Stream

Mass Flow (kg/1000kg product)

Physical State of Chemical Losses

Gas
Liquid
Solid

Cumene Sulfu- a- Inorga-

Total Benze Phospho- Aceto- Acetophe- Sat'd Sat'd Temp
Stre-ams Propylene Cumene O2 Hydropero- ric Phenol H2 methyl nic Ogranics
Flow ne ric Acid ne none Steam Water (C)
xide Acid styrene Salts
1 910 910 20
2 1 1 20
3 490 490 20
4 910 910 20
5 1 1 20
6 490 490 20
7 1,409 910 490 9 20
8 1,409 910 490 9 20
9 1,409 910 490 9
10 5,924 3,118 1,010 623 1,022 74 77 56
11 1,409 910 490 9
12 1,409 9 1,386 14 230
13 1,409 9 1,386 14 230
14 1,409 9 1,386 14

updated on 10/4/2010 9
Griffing and Overcash, Chemical Life Cycle Database, www.environmentalclarity.com, 1999-present.
 Cumene Sulfu- a- Inorga-
Total Benze Phospho- Aceto- Acetophe- Sat'd Sat'd Temp
Stre-ams Propylene Cumene O2 Hydropero- ric Phenol H2 methyl nic Ogranics
Flow ne ric Acid ne none Steam Water (C)
xide Acid styrene Salts
15 1,409 9 1,386 14
16 1,409 9 1,386 14 110
17 1,409 9 1,386 14 110
18 9 9 110
19 1,401 1,386 15 110
20 18 18 20
21 18 18 20
22 4,140 3,118 1,022 152
23 5,560 5,543 17 110
24 5,560 5,543 17 110
25 387 387 20
26 387 387 20
27 5,947 3,118 1,667 1,022 24 74 42 110
28 5,947 3,118 1,667 1,022 24 74 42 110
29a 48 48 20
29 72 24 48
30 5,923 3,118 1,667 1,022 74 42 110
31 5,923 3,118 1,667 1,022 74 42 110
32 5,923 3,118 1,667 1,022 74 42 80
33 1 1 20
34 1 1 20
35 1 1 80
36 5,940 3,118 16 1,010 623 1,022 74 77 80
37 16 16 80
38 16 16 80

updated on 10/4/2010 10
Griffing and Overcash, Chemical Life Cycle Database, www.environmentalclarity.com, 1999-present.
 Cumene Sulfu- a- Inorga-
Total Benz Phospho- Aceto- Acetophe- Sat'd Sat'd Temp
Stre-ams Propylene Cumene O2 Hydropero- ric Phenol H2 methyl nic Ogranics
Flow ene ric Acid ne none Steam Water (C)
xide Acid styrene Salts
39 5,924 3,118 1,010 623 1,022 74 77 80
40 5,301 3,118 1,010 1,022 74 77 56
41 623 623 56
42 1,161 1,000 74 77 152
43 161 10 74 77 181
44 1,000 1,000 181
45 1,000 1,000 20
46 623 623 20
Fugitive
75 9 3 27 2 10 5 13 5
losses
C1 555 555 20
C2 555 555 20
C3 555 555 50
C4 2,922 2,922 20
C5 2,922 2,922 20
C6 2,922 2,922 50
C7 7200 7,200 20
C8 7200 7,200 20
C9 7200 7,200 50
C10 31125 31,125 20
C11 31125 31,125 20
C12 31125 31,125 50

updated on 10/4/2010 11
Griffing and Overcash, Chemical Life Cycle Database, www.environmentalclarity.com, 1999-present.
 Cumene Sulfu- a- Inorga-
Total Benz Phospho- Aceto- Acetophe- Sat'd Sat'd Temp
Stre-ams Propylene Cumene O2 Hydropero- ric Phenol H2 methyl nic Ogranics
Flow ene ric Acid ne none Steam Water (C)
xide Acid styrene Salts
C13 11,502 11,502 20
C14 11,502 11,502 20
C15 11,502 11,502 50
C16 452 452 20
C17 452 452 20
C18 452 452 50
C19 3,577 3,577 20
C20 3,577 3,577 20
C21 3,577 3,577 50
C22 16,367 16,367 20
C23 16,367 16,367 20
C24 16,367 16,367 50
C25 1,087 1,087 20
C26 1,087 1,087 20
C27 1,087 1,087 50
C28 20,541 20,541 20
C29 20,541 20,541 20
C30 20,541 20,541 50
C31 20,329 20,329 20
C32 20,329 20,329 20
C33 20,329 20,329 50
C34 2,560 2,560 20

Cumene Sulfu- a- Inorga-

Total Benze Phospho- Aceto- Acetophe- Sat'd Sat'd Temp
Stre-ams Propylene Cumene O2 Hydropero- ric Phenol H2 methyl nic Ogranics
Flow ne ric Acid ne none Steam Water (C)
xide Acid styrene Salts

updated on 10/4/2010 12
Griffing and Overcash, Chemical Life Cycle Database, www.environmentalclarity.com, 1999-present.
C35 2,560 2,560 20
C36 2,560 2,560 50
S1 0.10 0 130
S2 0.10 0 130
S3 409 409 130
S4 409 409 130
S5 2,895 2,895 130
S6 2,895 2,895 130
S7 935 935 130
S8 935 935 130

updated on 10/4/2010 13
Griffing and Overcash, Chemical Life Cycle Database, www.environmentalclarity.com, 1999-present.
Graph of Cumulative Chemical Losses through Manufacturing Process

Cumalative Chemical Loss/1000 kg Product vs. Process Stream Number

300

250
kg Waste/1000 kg Product

200

150

100

50

0
1 5 9 13 17 21 25 29 33 37 41 45 C3 C7 C11 C15 C19 C23 C27 C31 C35 S3 S7 Fug
Stream Number

updated on 10/4/2010 14
Griffing and Overcash, Chemical Life Cycle Database, www.environmentalclarity.com, 1999-present.
Graph of Cumulative Contaminated Water Use/Emission through Manufacturing Process

Cumulative Contaminated Water

60
50
40
kg

30
20
10
0

15
21

27
33
1
7

S3
S9
3

9
13
19
25

31
37

43
C

C
C
C

C
C
Graph of Cumulative Non-Contaminated Water Use/Emission through Manufacturing Process

updated on 10/4/2010 15
Griffing and Overcash, Chemical Life Cycle Database, www.environmentalclarity.com, 1999-present.
 Cumulative Non-Contaminated Water

140000

120000

100000
kg/1000 kg product

80000

60000

40000

20000

0
10

12

14

16

18

20

22

24

26

28

30

32

34

36

S2

S4

S6

S8

0
4

S1
C

updated on 10/4/2010 16
Griffing and Overcash, Chemical Life Cycle Database, www.environmentalclarity.com, 1999-present.
Energy Input for each Unit Process, Cumulative Energy Requirements, Cooling Requirements (exotherms), and
Assumed Heat Recovery from Hot Streams Receiving Cooling
Energy Input (MJ/1000 kg Product) Cooling Requirements (MJ/1000 kg Product)

Unit Operation Energy Input Unit Operation Cumulative Unit Operation Energy Loss* Cumulative Heat Recovered** Temp C
Pump A 5.98E-08 Pump A 5.98E-08 Cooler A -59 -59 -15 128
Pump B 2.97E-02 Pump B 2.97E-02 Cooler B -310 -369 -78 110
Compressor A 28 Compressor A 2.80E+01 Acetone Cooler -48 -417 0 56
Mixer A 0.537 Mixer A 2.86E+01 Phenol Cooler -380 -797 -171 181
Pump C 0.492 Pump C 2.91E+01 Cooler C -272 -1069 -68 80
Heat Exchanger Heat Exchanger 2.91E+01 Benz Alk React -1739 -2808 -783 265
Compressor B 349 Compressor B 3.78E+02 Hydrogenator -115 -2923 -29 110
Pump M 0.992 Pump M 3.79E+02 Oxidizer -2182 -5105 -546 110
Pump D 0.181 Pump D 3.79E+02 Acidifier -2160 -7265 -540 80
Pump E 0.054 Pump E 3.79E+02 Condenser A -765 -8030 0 56
Pump F 0.146 Pump F 3.79E+02 Condenser B -3307 -11337 -1488 152
Cent Separator A 6.7 Cent Separator A 3.86E+02 Condenser C -1222 -12559 -550 181
Compressor C 21 Compressor C 4.07E+02 Turbine A -7.5 -12567 -8 230
Pump O 8.30E-06 Pump O 4.07E+02 Turbine B -4.2 -12571 -4 110
Compressor D 1087 Compressor D 1.49E+03 Heat Exchanger -250 12821 -113 230
Compressor E 85 Compressor E 1.58E+03 Total -4391
Pump P 8.24E-04 Pump P 1.58E+03
Washer 1.34 Washer 1.58E+03
Pump G 0.152 Pump G 1.58E+03 *Energy loss to cooling streams
Pump H 0.261 Pump H 1.58E+03 **Energy gained with cooling water streams
Pump I 4.00E-05 Pump I 1.58E+03
Preheater B 0.21 Preheater B 1.58E+03
Pump Q 1.40E-03 Pump Q 1.58E+03
Cent Separator B 6.7 Cent Separator B 1.59E+03
Pump N 0.378 Pump N 1.59E+03
Pump J 1.20E-05 Pump J 1.59E+03
Ac Dist Column 765 Ac Dist Column 2.35E+03
Pump R 0.007 Pump R 2.35E+03
Pump K 4.08E-02 Pump K 2.35E+03
Cumene Dist Col 4262 Cumene Dist Col 6.62E+03
Pump S 6.39E-02 Pump S 6.62E+03
Finishing Col 1296 Finishing Col 7.91E+03
Pump T 0.054 Pump T 7.91E+03
Pump L 0.337 Pump L 7.91E+03 -14775.29
Heat Recovered -4391 Heat Recovered 3.52E+03 -4390.80

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Griffing and Overcash, Chemical Life Cycle Database, www.environmentalclarity.com, 1999-present.
*Energy Loss to Cooling Streams
**Energy that can be gained from HX with Cooling Water Streams.
Based on 85% Efficiency for all HX, Coolers, and Condensers.

updated on 10/4/2010 18
Griffing and Overcash, Chemical Life Cycle Database, www.environmentalclarity.com, 1999-present.
Graph of Cumulative Energy Requirements

Cumulative Energy Input

9.00E+03

8.00E+03

7.00E+03

6.00E+03
MJ/1000 kg product

5.00E+03

4.00E+03

3.00E+03

2.00E+03

1.00E+03

0.00E+00

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updated on 10/4/2010 19
Griffing and Overcash, Chemical Life Cycle Database, www.environmentalclarity.com, 1999-present.