PROCESS ECONOMICS
PROGRAM
Abstract
SRI INTERNATIONAL
Menlo Park, California
94025
Process Economics Program Report No. 171B
PESTICIDES AND INTJMMIIDIATES
(September 1986)
This report presents the technology and economics of the manufac-
ture of benomyl, a fungicide, and phenmedipham, a pesticide, and their
intermediates.
Commercially, benomyl is made from o-phenylenediamine, methyl
chloroformate, cyanamide, and n-butyl isocyanate. Phenmedipham is made
from m-aminophenol, methyl chloroformate, and m-tolyl isocyanate. The
two isocyanates are made from their corresponding amines. Some among
these intermediates are produced by two manufacturing processes. Thus,
the processes evaluated in this report are benomyl and phenmedipham
from the intermediates mentioned before; o-phenylenediamine from
o-chloronitrobenaene and fram o-dichlorobenzene; methyl chloroformate
from methanol and Phosgene; cyanamide from calcium cyanamide and carbon
dioxide; n-butyl isocyanate from n-butylamine; n-butylamine from
n-butyl alcohol and from Irbutyraldehyde; m-aminophenol from nitroben-
eene via sulfonation, reduction and caustic fusion, and m-aminophenol
from resorcinol; m-tolyl isocyanate from m-toluidine; and m-toluidine
from toluene by nitration, reduction and isomer separation, and
m-toluidine from m-cresol.
PEP'85 YCY
I I a cl
Report No. 171 B
PESTICIDES AND INTERMEDIATES
SUPPLEMENT B
by YEN-CHEN YEN and DIN-JIN LIN
with contributions by CHIH-WEI LEE
September 1666
A private report by the
PROCESS ECONOMICS PROGRAM
Menlo Park, California 94025
For detailed marketing data and information, the reader is
referred to one of the SRI programs specializing in marketing
research. The CHEMICAL ECONOMICS HANDBOOK Program covers
most major chemicals and chemical products produced in the
United States and the WORLD PETROCHEMICALS Program covers
major hydrocarbons and their derivatives on a worldwide basis.
In addition, the SRI DIRECTORY OF CHEMICAL PRODUCERS services
provide detailed lists of chemical producers by company, prod-
uct, and plant for the United States and Western Europe.
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2
0
3
a
4 BENCMYL .........................................................
CONTENTS
INTRODUCTION .................................................... 1
SUMMARY ......................................................... 3
General Aspects .................................................
Technical Aspects ...............................................
Benomyl ...................................................... o-Phenylenediamine from o-Nitrochlorobenzene ................. o-Phenylenediamine from o-Dichlorobenzene .................... Methyl Chloroformate ......................................... Cyanamide .................................................... n-Butyl Isocyanate from n-Butyl Amine ........................ n-Butyl Amine from n-Butyraldehyde ........................... n-Butyl Amine from n-Butanol ................................. Phenmedipham ................................................. m-Aminophenol from Nitrobenzene .............................. m-Aminophenol from Resorcinol ................................ m-Tolyl Isocyanate .......................................... m-Toluidine from Toluene ..................................... m-Toluidine from m-Cresol ....................................
INDUSTRY STATUS .................................................
3
7
7 7 7 8 8 8 8 9 9 9 10 10 10 11
Methyl Chloroformate ............................................
n-Butyl Isocyanate and m-Tolyl Isocyanate .......................
m-Aminophenol and m-Toluidine ...................................
n-Butyl Amine ...................................................
o-Phenylenediamine ..............................................
Cyanamide .......................................................
Review of Processes .............................................
A. Processes from o-Phenylenediamine to Methyl Benzimidazole-2-ylcarbamate (Formula II) ....................
B. Processes from Methyl Benzimidazole-2-ylcarbamate (Formula II) to Benomyl (Formula I) .........................
C. Processes from o-Phenylenediamine to Aminobenzimidazole (Formula III in Figure 4.1) ..................................
D. Processes from Aminobenzimidazole (Formula III) to Methyl Benzimidazole-2-ylcarbamate (Formula II) .....................
E. Other Processes ..............................................
Process Description .............................................
Process Discussion ..............................................
Cost Estimates ..................................................
13
14
15
15
15
18
18
23
24
24
29
29
30 31
32
40
40
. . . -lll-
CONTENTS
5 o-PHENYLENEDIAMINE .,,.........................*................. 47
Review of Processes ............................................. 47
Reduction of o-Nitroaniline .................................. 47 Amination of o-Dichlorobenzene ............................... 48 Direct Amination of Aniline .................................. 48 Other Processes .............................................. 49
A Process for Preparing o-Phenylenediamine from o-Nitrochlorobenzene via o-Nitrolaniline ....................... 50
Process Description .......................................... 50 Process Discussion ........................................... 57 Cost Estimates ............................................... 57
A Process for Preparing o-Phenylenediamine from o-Dichlorobenzene .............................................. 63
Process Description .......................................... 63 Process Discussion ........................................... 70 Cost Estimates ............................................... 70
0 ME!CHYL CHLOROFORMATB ............................................ 75
Review of Processes ............................................. 75
Process Description ............................................. 78
Process Discussion .............................................. 81
Cost Estimates .................................................. 81
7 CYANAMIDE . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 89
Chemistry ....................................................... 8Q
Process Description ............................................. 91
Process Discussion .............................................. 97
Cost Estimates .................................................. 97
8 n-BUTYL ISOCYANATF. AND n-BUTYLAMINE . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 101
Review of Processes for Making n-Butyl Isocyanate ............... 101
From Phosgene and n-Butylamine ............................... 101 Processes Using Phenyl Chloroformate or Phenyl Carbonate ..... 103 Nonphosgenation Processes .................................... 103
Review of Processes for Preparation of n-Butylamine ............. 103
From n-Butanol ............................................... 103 From n-Butyraldehyde ......................................... 104 From n-Butyl Chloride ........................................ 105 Other Processes .............................................. 105
A Process for the Production of n-Butyl Isocyanate from n-Butylamine .................................................. 106
Process Description .......................................... 106 Process Discussion ........................................... 115
-iv-
CONTENTS
8 n-BUTYL ISOCYANATE AND n-BUTYLAM INE (Continued)
Cost Estimates ............................................... 115
A Process for the Manufacture of n-Butylamine from n-Butyraldehyde ................................................ 122
Process Description .......................................... 122 Process Discussion ........................................... 128 Cost Estimates ............................................... 128
A Process for Producing n-Butylamine from n-Butanol ............. 132
Process Description .......................................... 132 Process Discussion ........................................... 139 Cost Estimates ............................................... 139
Q PHENMEDIPHAM .................................................... 143
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a
Review of Processes ............................................. 143
Process Description ............................................. 146
Process Discussion .............................................. 159
Cost Estimates .................................................. 159
10 m-AMINOPHENOL . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 165
Review of Processes ............................................. 165
From Metanilic Acid by Alkali Fusion ......................... 165 From Resorcinol by Amination ................................. 166 From m-Aminobenzoic Acid by Caustic Fusion and Acidification ............................................... 166 From 3-Aminocyclohexanone by Dehydrogenation ................. 167 From m-Phenylenediamine by Hydrolysis ........................ 167 From Oxidation of Aniline by Peroxide ........................ 168 From m-Nitrophenol by Reduction .............................. 168
A Process for Manufacture of m-Aminophenol from Nitrobenxene via Metanilic Acid ................................ 168
Process Description .......................................... 168 Process Discussion ........................................... 177 Cost Estimates ............................................... 178
A Process for Producing q -Aminophenol from Resorcinol ........... 182
Process Description .......................................... 182 Process Discussion ........................................... 188 Cost Estimates ............................................... 188
11 m-TOLYL ISOCYANATE AND m-TOLUIDINE .............................. 193
Review of a Process for the Preparation of III-Tolyl Isocyanate ... 193
Review of Processes for Preparation of q -Toluidine .............. 193 From Nitrotoluene ............................................ 193 From m-Cresol ................................................ 195 From Benzaldehyde ............................................ 195
CONTENTS
m-TOLYL ISOCYANATE AND m-TOLUIDINE (Continued)
By the Direct Amination of Toluene ........................... 195 Other Processes .............................................. 196
A Process for Producing m-Tolyl Isocyanate ...................... 198
Process Description .......................................... 198 Process Discussion ........................................... 205 Cost Estimates ............................................... 205
A Process for Preparing Toluidines from Toluene via Nitration and Reduction Followed by Isomer Separation .......... 212
Process Description .......................................... 212 Process Discussion ........................................... 224 Cost Estimates ............................................... 224
A Process for the Preparation of m-Toluidine from m-Cresol ...... 229
Process Description .......................................... 229 Process Discussion ........................................... 235 Cost Estimates ............................................... 235
APPENDIX A: COST ESTIMATION METHOD . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 239
APPENDIX B: BENOMYL AND PHENMEDIPHAM: GENERAL DESCRIPTION OF PROPERTIES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 241
APPENDIX C: PHYSICAL DATA . . . . . . . . ..*............................... 245
CITED REFERENCES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 275
PATENT REFERENCES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 287
ILLUSTRATIONS
4.1
4.2
5.1
5.2
6.1
7.1
8.1
8.2
8.3
9.1
10.1
10.2
11.1
11.2
11.3
Processes for Preparation of Benomyl and Its Precursors . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Benomyl Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
o-Phenylenediamine from o-Nitrochlorobenzene Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..*......
o-Phenylenediamine from o-Dichlorobenzene Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..*...........
Methyl Chloroformate Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..*...........
Cyanamide Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ...*
n-Butyl Isocyanate from n-Butylamine Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
n-Butylamine from n-Butyraldehyde Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..*......
n-Butylamine from n-Butanol Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Phenmedipham Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..a*...
m-Aminophenol from Nitrobenzene via Metanilic Acid Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
m-Aminophenol from Resorcinol Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
m-Tolyl Isocyanate from m-Toluidine Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
m-Toluidine from Toluene Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
m-Toluidine from m-Cresol Flow Sheet . . . . . ..a......................................
25
295
297
299
301
303
305
307
309
311
315
317
319
321
325
- vii -
2.1
2.2
3.1
3.2
3.3
3.4
3.5
3.6
3.7
3.8
4.1
4.2
4.3
4.4
4.5
4.6
4.7
4.8
4.9
4.10
5.1
5.2
5.3
5.4
TABLES
Cost Features of Benomyl and Phenmedipham ...............
Cost Features of Intermediates for Making Benomyl and Phenmedipham ...........................................
World Producers of Benomyl and Phenmedipham (1985) ......
World Producers of Methyl Chloroformate (1984) ..........
World Producers of n-Butyl Isocyanate and m-Tolyl Isocyanate (1984) ..............................
World Producers of m-Aminophenol (lQ84) .................
World Producers of m-Toluidine (1984) ...................
World Producers of Alkylamines, Including n-Butyl Amine (1984) ...........................................
World Producers of o-Phenylenediamine (1984) ............
World Producers of Cyanamide ............................
Manufacture of Benomyl and Its Precursors Summary of Du Pont Patents ..............................
Benomyl and Its Precursors and Homologs Summary of Patents Assigned to Others than Du Pont ......
Benomyl Production Design Bases and Assumptions ............................
Benomyl Stream Flows ............................................
Benomyl Major Equipment .........................................
Benomyl Utilities Summary .......................................
Benomyl Total Capital Investment ................................
Benomyl Production Costs ........................................
Costs of Raw Materials for Benomyl and Prices Assumed for Du Pont ....................................
Du Pont's Probable Production Cost of Benomyl ...........
o-Phenylenediamine Preparation Patent Summary ..........................................
o-Phenylenediamine from o-Nitrochlorobenzene Design Bases and Assumptions ............................
o-Phenylenediamine from o-Nitrochlorobenzene Stream Flows ............................................
o-Phenylenediamine from o-Nitrochlorobenzene Major Equipment .........................................
- ix -
4
5
14
16
17
18
19
20
21
21
253
254
33
35
37
39
42
43
45
46
259
51
52
54
5.5
5.6
5.7
5.8
5.9
5.10
5.11
5.12
5.13
5.14
6.1
6.2
6.3
6.4
6.5
6.6
6.7
6.8
7.1
7.2
7.3
TABLES
o-Phenylenediamine from o-Nitrochlorobenzene Utilities Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
o-Phenylenediamine from o-Nitrochlorobenzene Total Capital Investment ,,..............................
o-Phenylenediamine from o-Nitrochlorobenzene Production Costs . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Production of o-Nitroaniline and o-Phenylenediamine in Two Processes Cost Features . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
o-Phenylenediamine from o-Dichlorobenzene Design Bases and Assumptions ,,,,..........,,,,,,,,......
o-Phenylenediamine from o-Dichlorobenzene Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
o-Phenylenediamine from o-Dichlorobenzene Major Equipment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
o-Phenylenediamine from o-Dichlorobenzene Utilities Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
o-Phenylenediamine from o-Dichlorobenzene Total Capital Investment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
o-Phenylenediamine from o-Dichlorobenzene Production Costs . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Methyl Chloroformate Manufacture Patent Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..*.........
Methyl Chloroformate Design Bases and Assumptions . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Methyl Chloroformate Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Methyl Chloroformate Major Equipment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Methyl Chloroformate Utilities Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Methyl Chloroformate Capital Investment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Methyl Chloroformate Production Costs . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Methyl Chloroformate without Recovery of HCl Cost Features . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Preparation of Cyanamide Patent Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Cyanamide from Calcium Cyanamide Design Bases and Assumptions . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Cyanamide from Calcium Cyanamide Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
56
59
60
62
64
66
67
69
72
73
261
77
78
79
80
83
85
87
92
94
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TABLES
7.4
7.5
7.6
7.7
8.1
8.2
8.3
8.4
8.5
8.6
8.7
8.8
8.9
8.10
8.11
8.12
8.13
8.14
8.15
8.16
8.17
Cyanamide from Calcium Cyanamide Major Equipment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ...*....*
Cyanamide from Calcium Cyanamide Utilities Summary .,.......,........................,....
Cyanamide from Calcium Cyanamide Total Capital Investment .,..........................*...
Cyanamide from Calcium Cyanamide Production Costs . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
n-Butyl Isocyanate Preparation Patent Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Preparation of n-Butylamine Patent Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..*....*.
n-Butyl- Isocyanate from n-Butylamine Design Bases and Assumptions . . . . . . . . . . . . . . . . ..*.*.......
n-Butyl Isocyanate from n-Butylamine Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . . . . ...*..........*..
n-Butyl Isocyanate from n-Butylamine Major Equipment . . . . . . . . . . . . . . . . . . . . ..*......*.......a...
n-Butyl Isocyanate from n-Butylamine Utilities Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..a....
n-Butyl Isocyanate from n-Butylamine Capital Investment . . . . . . . . . . . . . . . . ..*...................
n-Butyl Isocyanate from n-Butylamine Production Costs . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
n-Butyl Isocyanate from n-Butylamine Cost Features . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..*...........
n-Butylamine from n-Butyraldehyde Design Bases and Assumptions . . . . . . . . . . . . . . . . . ..**...*...
n-Butylamine from n-Butyraldehyde Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ...*.
n-Butylamine from n-Butyraldehyde Major Equipment . . . . . . . . . . . . . . . . . . . . . . . ..*...............
n-Butylamine from n-Butyraldehyde Utilities Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
n-Butylamine from n-Butyraldehyde Total Capital Investment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
n-Butylamine from n-Butyraldehyde Production Costs . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
n-Butylamine from n-Butanol Design Bases and Assumptions . . . . . . . . ...***...........*..
n-Butylamine from n-Butanol Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
- xi -
95
96
98
263
265
107
109
112
114
117
119
121
123
124
125
127
129
130
133
134
TABLES
8.18
8.19
8.20
8.21
9.1
9.2
9.3
Q.4
9.5
Q.6
9.7
10.1
10.2
10.3
10.4
10.5
10.6
10.7
10.8
10.9
10.10
n-Butylamine from n-Butanol Major Equipment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
n-Butylamine from n-Butanol Utilities Summary ,......................................
n-Butylamine from n-Butanol Total Capital Investment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
n-Butylamine from n-Butanol Production Costs . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Phenmedipham Patent Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Phenmedipham Design Bases and Assumptions . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Phenmedipham Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Phenmedipham Major Equipment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Phenmedipham Utilities Summary ,......................................
Phenmedipham Capital Investment by Section . . . . . . . . . . . . . . . . . . . . . . . . . . .
Phenmedipham Production Costs . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
m-Aminophenol Preparation Patent Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
m-Aminophenol from Nitrobenzene Design Bases and Assumptions . . . . . . . . . . . . . . . . . . . . . . . . . . . .
m-Aminophenol from Nitrobenzene via Metanilic Acid Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
m-Aminophenol from Nitrobenzene via Metanilic Acid Major Equipment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
m-Aminophenol from Nitrobenzene via Metanilic Acid Utilities Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
m-Aminophenol from Nitrobenzene via Metanilic Acid Total Capital Investment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
m-Aminophenol from Nitrobenzene via Metanilic Acid Production Costs . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
m-Aminophenol from Besorcinol Design Bases and Assumptions . . . . . . . . . . . . . . . . . . . . . . . . . . . .
m-Aminophenol from Besorcinol Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
m-Aminophenol from Besorcinol Major Equipment ..,..,.............................‘.....
136
138
140
141
268
147
150
155
158
161
163
269
16s
172
174
176
179
180
182
184
185
a
0
- xii -
TABLES
a
a
a
a
0
a
10.11
10.12
10.13
11.1
11.2
11.3
11.4
11.5
11.6
11.7
11.8
11.9
11.10
11.11
11.12
11.13
11.14
11.15
m-Aminophenol from Resorcinol Utilities Summary . . . . ..I................................
m-Aminophenol from Resorcinol Total Capital Investment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
m-Aminophenol from Resorcinol Production Costs . . . . . ..*................*...............
m-Toluidine Preparation Patent Summary . . . . . . ..*.......*......*.*................
m-Tolyl Isocyanate from m-Toluidine Design Bases and Assumptions . . . . . . . . . . ..*...............
m-Tolyl Isocyanate from m-Toluidine Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . . . . ..*..............
m-Tolyl Isocyanate from m-Toluidine Major Equipment *........,.......,........**,............
m-Tolyl Isocyanate from q -Toluidine Utilities Summary ,.......,,....*............*...........
m-Tolyl Isocyanate from m-Toluidine Total Capital Investment . . . . . . . . . . . . . . . . . . ..**..........
q -Tolyl Isocyanate from m-Toluidine Production Costs . . . . . . . . . . . . . . . . . . . . ..*.....*...........
q -Tolyl Isocyanate from m-Toluidine (Without HCl Recovery) Cost Features . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..a............
Toluidine from Toluene via Nitration, Hydrogenation, and Isomer Separation Design Bases and Assumptions . . . . . . . . . . . . . . ..*...........
Toluidines from Toluene via Nitration, Hydrogenation, and Isomer Separation Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . . ..*................
Toluidines from Toluene via Nitration, Hydrogenation, and Isomer Separation Major Equipment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Toluidines from Toluene via Nitration, Hydrogenation, and Isomer Separation Utilities Summary . . . ..*.......**.........**......*......
Toluidines from Toluene via Nitration, Hydrogenation, and Isomer Separation Capital Investment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Toluidines from Toluene via Nitration, Hydrogenation, and Isomer Separation Production Costs . . . ..*..................................
m-Toluidine from q -Cresol Design Bases and Assumptions ,,...a......................
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187
189
190
271
199
200
202
204
207
209
211
215
216
220
223
225
227
229
11.16
11.17
11.18
11.19
11.20
q -Toluidine from m-Cresol Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
m-Toluidine from m-Cresol ldajor Equipment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
m-Toluidine from q -cresol Utilities Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
m-Toluidine from m-Cresol Total Capital Investment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
m-Toluidine from m-Cresol Production Costs . . . ..o..................................
231
232
234
236
237
-
0
- xiv -
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