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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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

QQ

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 -