ALL CHAPTERS COVERED
SOLUTIONS MANUAL
,Contents
Preface.......................................................................................................................xi
Chapter 1 Introduction .......................................................................................... 1
1.1 What This Book Is About..........................................................1
1.2 Structure ....................................................................................2
1.3 How to Use the Book ................................................................. 3
Chapter 2 Synthesis Plan Analysis ....................................................................... 5
2.1 Synthesis Tree Diagrams ...........................................................5
2.1.1 Terms, Definitions, and Examples ............................... 5
2.1.2 Problems ..................................................................... 13
2.2 Linear Synthesis Plans ............................................................ 15
2.2.1 Terms, Definitions, and Examples ............................. 15
2.2.2 Problems ..................................................................... 16
2.3 Convergent Synthesis Plans ..................................................... 19
2.3.1 Terms, Definitions, and Examples ............................. 19
2.3.2 Problems .....................................................................34
2.4 Reaction Networks .................................................................. 36
2.4.1 Terms, Definitions, and Examples ............................. 36
2.4.2 Problems ..................................................................... 41
2.5 Ranking Synthesis Plans According to Material
Efficiency ................................................................................. 45
2.5.1 Terms, Definitions, and Examples ............................. 45
2.6 Excel Spreadsheet Tools: Part 1 .............................................. 82
2.6.1 Synthesis-Plan-Analysis-Basis-Materials-Metrics.xls ......82
2.6.2 Template-SYNTHESIS.xls ........................................ 82
2.6.3 Calculator-Cumulative-PMI.xls ................................. 83
2.7 Problems .................................................................................. 83
References ........................................................................................ 147
Chapter 3 Environmental Impact Metrics ........................................................ 153
3.1 Life Cycle Assessment........................................................... 153
3.1.1 Terms, Definitions, and Examples ........................... 155
3.2 Multi-Compartment Model ................................................... 166
3.2.1 Terms, Definitions, and Examples ........................... 166
3.3 Environmental Impact Potentials .......................................... 169
3.3.1 Terms, Definitions, and Examples ........................... 169
3.4 Benign Index ......................................................................... 191
3.4.1 Terms, Definitions, and Examples ........................... 191
vii
,viii Contents
3.5 Excel Spreadsheet Tools: Part 2 ............................................ 196
3.5.1 Descriptions of Spreadsheets ................................... 196
3.5.2 Assumptions and Dealing with Missing Data.......... 198
3.6 Problems ................................................................................200
References ........................................................................................208
Chapter 4 Safety-Hazard Impact Metrics ......................................................... 215
4.1 Parameters ............................................................................. 215
4.1.1 Terms, Definitions, and Examples ........................... 215
4.2 Safety-Hazard Impact Potentials ........................................... 223
4.2.1 Terms, Definitions, and Examples ........................... 223
4.3 Safety-Hazard Index .............................................................. 241
4.3.1 Terms, Definitions, and Examples ........................... 241
4.4 Excel Spreadsheet Tools: Part 3 ............................................ 247
4.5 Problems ................................................................................248
References ........................................................................................ 251
Chapter 5 Energy Metrics ................................................................................. 253
5.1 Thermodynamic Preliminaries ............................................. 255
5.1.1 Terms, Definitions, and Examples ........................... 255
5.1.2 Predicting Thermochemical Properties ................... 274
5.2 Thermodynamic Calculations ............................................... 285
5.2.1 Determination of Phases of Input Materials in a
Given Chemical Reaction......................................... 285
5.2.2 Determination of Molar Volume of a Substance
at a Given Pressure and Temperature for a Given
Cubic Equation of State............................................ 285
5.2.3 Derivation of ∫ pdV Expressions for Various
Cases in P-V Diagrams Related to Determining
Work Done by Fluids During Reversible
Isothermal Expansion or Contraction ...................... 289
5.2.4 Derivation of Expressions for ∫ p (V ) dV for
Various Equations of State ....................................... 295
5.2.4.1 van der Waals EOS ................................... 295
5.2.4.2 Redlich–Kwong EOS ................................ 296
5.2.4.3 Peng–Robinson EOS................................. 296
5.2.5 Determination of Expressions for Enthalpy
Change due to Temperature and Pressure
Contributions ............................................................ 297
5.2.5.1 Case I: State 1 (gas) to State 2 (gas) ......... 297
5.2.5.2 Case II: State 1 (liquid) to State 2 (gas) .... 301
5.2.5.3 Case III: State 1 (liquid)
to State 2 (liquid) ......................................302
5.2.5.4 Case IV: State 1 (gas) to State 2 (liquid) ...... 303
5.2.6 Worked Examples.....................................................307
, Contents ix
5.3 Types of Energy Metrics ....................................................... 319
5.3.1 Terms, Definitions, and Examples ........................... 319
5.4 Excel Spreadsheet Tools: Part 4 ............................................ 335
5.5 Problems ................................................................................ 337
References ........................................................................................ 341
Chapter 6 Algorithms........................................................................................ 345
6.1 Environmental Assessment Tool for Organic Synthesis ....... 345
6.1.1 Description of Program ............................................ 345
6.1.2 Instructions for Using Program ................................348
6.2 EcoScale ................................................................................ 355
6.2.1 Description of Algorithm ......................................... 355
6.2.2 EcoScale-Template.xls ............................................. 355
6.3 Edwards–Lawrence Algorithm ............................................. 357
6.3.1 Description of Algorithm ......................................... 357
6.3.2 Edwards-Lawrence-Template.xls ............................. 358
6.4 GreenStar ............................................................................... 361
6.4.1 Description of Algorithm ......................................... 361
6.4.2 GreenStar-Template.xls ............................................ 362
6.5 Multivariate Method .............................................................. 362
6.5.1 Description of Algorithm ......................................... 362
6.5.2 Multivariate-Template.xls......................................... 368
6.6 UTGCI Method ..................................................................... 368
6.6.1 Description of Algorithm ......................................... 368
6.6.2 UTGCI-Template.xls ................................................ 370
6.7 Andraos Algorithm................................................................ 370
6.7.1 Description of Algorithm ......................................... 370
6.8 Rowan Solvent Greenness Index ........................................... 377
6.8.1 Description of Algorithm ......................................... 377
6.8.2 Rowan-Solvent-Greenness-Index.xls ....................... 380
6.9 Epilogue ................................................................................. 385
6.10 Problems ................................................................................ 387
References ........................................................................................ 389
Chapter 7 Examples from the Chemical Industry ............................................ 391
7.1 Terms, Definitions, and Examples......................................... 391
7.2 Problems ................................................................................ 392
References ........................................................................................ 499
Appendix: Other Terminologies ......................................................................... 503
Index ......................................................................................................................509
SOLUTIONS MANUAL
,Contents
Preface.......................................................................................................................xi
Chapter 1 Introduction .......................................................................................... 1
1.1 What This Book Is About..........................................................1
1.2 Structure ....................................................................................2
1.3 How to Use the Book ................................................................. 3
Chapter 2 Synthesis Plan Analysis ....................................................................... 5
2.1 Synthesis Tree Diagrams ...........................................................5
2.1.1 Terms, Definitions, and Examples ............................... 5
2.1.2 Problems ..................................................................... 13
2.2 Linear Synthesis Plans ............................................................ 15
2.2.1 Terms, Definitions, and Examples ............................. 15
2.2.2 Problems ..................................................................... 16
2.3 Convergent Synthesis Plans ..................................................... 19
2.3.1 Terms, Definitions, and Examples ............................. 19
2.3.2 Problems .....................................................................34
2.4 Reaction Networks .................................................................. 36
2.4.1 Terms, Definitions, and Examples ............................. 36
2.4.2 Problems ..................................................................... 41
2.5 Ranking Synthesis Plans According to Material
Efficiency ................................................................................. 45
2.5.1 Terms, Definitions, and Examples ............................. 45
2.6 Excel Spreadsheet Tools: Part 1 .............................................. 82
2.6.1 Synthesis-Plan-Analysis-Basis-Materials-Metrics.xls ......82
2.6.2 Template-SYNTHESIS.xls ........................................ 82
2.6.3 Calculator-Cumulative-PMI.xls ................................. 83
2.7 Problems .................................................................................. 83
References ........................................................................................ 147
Chapter 3 Environmental Impact Metrics ........................................................ 153
3.1 Life Cycle Assessment........................................................... 153
3.1.1 Terms, Definitions, and Examples ........................... 155
3.2 Multi-Compartment Model ................................................... 166
3.2.1 Terms, Definitions, and Examples ........................... 166
3.3 Environmental Impact Potentials .......................................... 169
3.3.1 Terms, Definitions, and Examples ........................... 169
3.4 Benign Index ......................................................................... 191
3.4.1 Terms, Definitions, and Examples ........................... 191
vii
,viii Contents
3.5 Excel Spreadsheet Tools: Part 2 ............................................ 196
3.5.1 Descriptions of Spreadsheets ................................... 196
3.5.2 Assumptions and Dealing with Missing Data.......... 198
3.6 Problems ................................................................................200
References ........................................................................................208
Chapter 4 Safety-Hazard Impact Metrics ......................................................... 215
4.1 Parameters ............................................................................. 215
4.1.1 Terms, Definitions, and Examples ........................... 215
4.2 Safety-Hazard Impact Potentials ........................................... 223
4.2.1 Terms, Definitions, and Examples ........................... 223
4.3 Safety-Hazard Index .............................................................. 241
4.3.1 Terms, Definitions, and Examples ........................... 241
4.4 Excel Spreadsheet Tools: Part 3 ............................................ 247
4.5 Problems ................................................................................248
References ........................................................................................ 251
Chapter 5 Energy Metrics ................................................................................. 253
5.1 Thermodynamic Preliminaries ............................................. 255
5.1.1 Terms, Definitions, and Examples ........................... 255
5.1.2 Predicting Thermochemical Properties ................... 274
5.2 Thermodynamic Calculations ............................................... 285
5.2.1 Determination of Phases of Input Materials in a
Given Chemical Reaction......................................... 285
5.2.2 Determination of Molar Volume of a Substance
at a Given Pressure and Temperature for a Given
Cubic Equation of State............................................ 285
5.2.3 Derivation of ∫ pdV Expressions for Various
Cases in P-V Diagrams Related to Determining
Work Done by Fluids During Reversible
Isothermal Expansion or Contraction ...................... 289
5.2.4 Derivation of Expressions for ∫ p (V ) dV for
Various Equations of State ....................................... 295
5.2.4.1 van der Waals EOS ................................... 295
5.2.4.2 Redlich–Kwong EOS ................................ 296
5.2.4.3 Peng–Robinson EOS................................. 296
5.2.5 Determination of Expressions for Enthalpy
Change due to Temperature and Pressure
Contributions ............................................................ 297
5.2.5.1 Case I: State 1 (gas) to State 2 (gas) ......... 297
5.2.5.2 Case II: State 1 (liquid) to State 2 (gas) .... 301
5.2.5.3 Case III: State 1 (liquid)
to State 2 (liquid) ......................................302
5.2.5.4 Case IV: State 1 (gas) to State 2 (liquid) ...... 303
5.2.6 Worked Examples.....................................................307
, Contents ix
5.3 Types of Energy Metrics ....................................................... 319
5.3.1 Terms, Definitions, and Examples ........................... 319
5.4 Excel Spreadsheet Tools: Part 4 ............................................ 335
5.5 Problems ................................................................................ 337
References ........................................................................................ 341
Chapter 6 Algorithms........................................................................................ 345
6.1 Environmental Assessment Tool for Organic Synthesis ....... 345
6.1.1 Description of Program ............................................ 345
6.1.2 Instructions for Using Program ................................348
6.2 EcoScale ................................................................................ 355
6.2.1 Description of Algorithm ......................................... 355
6.2.2 EcoScale-Template.xls ............................................. 355
6.3 Edwards–Lawrence Algorithm ............................................. 357
6.3.1 Description of Algorithm ......................................... 357
6.3.2 Edwards-Lawrence-Template.xls ............................. 358
6.4 GreenStar ............................................................................... 361
6.4.1 Description of Algorithm ......................................... 361
6.4.2 GreenStar-Template.xls ............................................ 362
6.5 Multivariate Method .............................................................. 362
6.5.1 Description of Algorithm ......................................... 362
6.5.2 Multivariate-Template.xls......................................... 368
6.6 UTGCI Method ..................................................................... 368
6.6.1 Description of Algorithm ......................................... 368
6.6.2 UTGCI-Template.xls ................................................ 370
6.7 Andraos Algorithm................................................................ 370
6.7.1 Description of Algorithm ......................................... 370
6.8 Rowan Solvent Greenness Index ........................................... 377
6.8.1 Description of Algorithm ......................................... 377
6.8.2 Rowan-Solvent-Greenness-Index.xls ....................... 380
6.9 Epilogue ................................................................................. 385
6.10 Problems ................................................................................ 387
References ........................................................................................ 389
Chapter 7 Examples from the Chemical Industry ............................................ 391
7.1 Terms, Definitions, and Examples......................................... 391
7.2 Problems ................................................................................ 392
References ........................................................................................ 499
Appendix: Other Terminologies ......................................................................... 503
Index ......................................................................................................................509
