GREEN CHEMISTRY

[Pages:395]Life

Water

Earth

Technology

GREEN CHEMISTRY

Air

AND THE TEN COMMANDMENTS OF SUSTAINABILITY

Stanley E. Manahan

manahans@missouri.edu

ChemChar Research, Inc. 2005

THE ELEMENTS

Atomic number

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56

Name

Symbol

Hydrogen H

Helium

He

Lithium

Li

Beryllium Be

Boron

B

Carbon

C

Nitrogen

N

Oxygen

O

Fluorine

F

Neon

Ne

Sodium

Na

Magnesium Mg

Aluminum Al

Silicon

Si

Phosphorus P

Sulfur

S

Chlorine

Cl

Argon

Ar

Potassium K

Calcium

Ca

Scandium Sc

Titanium

Ti

Vanadium V

Chromium Cr

Manganese Mn

Iron

Fe

Cobalt

Co

Nickel

Ni

Copper

Cu

Zinc

Zn

Gallium

Ga

Germanium Ge

Arsenic

As

Selenium

Se

Bromine

Br

Krypton

Kr

Rubidium Rb

Strontium Sr

Yttrium

Y

Zirconium Zr

Niobium

Nb

Molybdenum Mo

Technetium Tc

Ruthenium Ru

Rhodium

Rh

Palladium Pd

Silver

Ag

Cadmium Cd

Indium

In

Tin

Sn

Antimony Sb

Tellurium Te

Iodine

I

Xenon

Xe

Cesium

Cs

Barium

Ba

Atomic mass

1.00794 4.0026 6.941 9.01218 10.811 12.011 14.0067 15.9994 18.9984 20.1797 22.9898 24.305 26.98154 28.0855 30.973 32.066 35.4527 39.948 39.0983 40.078 44.9559 47.88 50.9415 51.9961 54.938 55.847 58.9332 58.6934 63.546 65.39 69.723 72.61 74.9216 78.96 79.904 83.8 85.4678 87.62 88.9056 91.224 92.9064 95.94 98 101.07 102.9055 106.42 107.8682 112.411 114.82 118.710 121.757 127.60 126.9045 131.29 132.9054 137.327

Atomic number Name

Symbol

Atomic mass

57

Lanthanum La

138.9055

58

Cerium

Ce

140.115

59

Praseodymium Pr

140.9077

60

Neodymium Nd

144.24

61

Promethium Pm

145

62

Samarium Sm

150.36

63

Europium

Eu

151.965

64

Gadolinium Gd

157.25

65

Terbium

Tb

158.925

66

Dysprosium Dy

162.50

67

Holmium

Ho

164.9303

68

Erbium

Er

167.26

69

Thulium

Tm

168.9342

70

Ytterbium Yb

173.04

71

Lutetium

Lu

174.967

72

Hafnium

Hf

178.49

73

Tantalum

Ta

180.9497

74

Tungsten

W

183.85

75

Rhenium

Re

186.207

76

Osmium

Os

190.2

77

Iridium

Ir

192.22

78

Platinum

Pt

195.08

79

Gold

Au

196.9665

80

Mercury

Hg

200.59

81

Thallium

Tl

204.383

82

Lead

Pb

207.2

83

Bismuth

Bi

208.98

84

Polonium

Po

209

85

Astatine

At

210

86

Radon

Rn

222

87

Francium

Fr

223

88

Radium

Ra

226.0254

89

Actinium

Ac

227.0278

90

Thorium

Th

232.038

91

Protactinium Pa

231.0359

92

Uranium

U

238.0289

93

Neptunium Np

237.048

94

Plutonium Pu

244

95

Americium Am

243

96

Curium

Cm

247

97

Berkelium Bk

247

98

Californium Cf

251

99

Einsteinium Es

252

100 Fermium

Fm

257.1

101

Mendelevium Md

258.1

102 Nobelium No

255

103 Lawrencium Lr

260

104 Rutherfordium Rf

261.11

105

Dubnium

Db

262.11

106 Seaborgium Sg

263.12

107 Bohrium

Bh

262.12

108 Hassium

Hs

265

__1_0_9______M__e_it_n_e_ri_u_m_____M__t______2_6_6_______

1 Elements above atomic number 92 have been

made artificially.

GREEN CHEMISTRY

AND THE TEN COMMANDMENTS OF SUSTAINABILITY 2nd ed

Stanley E. Manahan

2006

ChemChar Research, Inc Publishers

Columbia, Missouri U.S.A.

Copyright ? 2006 by Stanley E. Manahan All Rights Reserved. No part of this publication may be reproduced in any form or by any means, electronic or mechanical, including photocopy, recording, or any information storage and retrieval system, without permission in writing from the publisher.

ChemChar Research, Inc. 2005 Woodlea Drive Columbia, MO 65201 U.S.A. chemchar@

International Standard Book Number: 0-9749522-4-9

Printed in the United States of America

TABLE OF CONTENTS

Chapter 1. Chemistry, Green Chemistry, and Environmental Chemistry . . . . . . . . . . . 1 1.1. Chemistry Is Good . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 1.2. The Environment and the Five Environmental Spheres . . . . . . . . . . . . . . . . . . . . . 3 1.3. What Is Environmental Chemistry? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .5 1.4. Environmental Pollution . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5 1.5. What Is Green Chemistry? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .9 1.6. Green Chemistry and Synthetic Chemistry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 10 1.7. Reduction of Risk: Hazard and Exposure . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 12 1.8. The Risks of No Risks . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 14 1.9. Waste Prevention . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 15 1.10. Basic Principles of Green Chemistry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 16 1.11. Some Things to Know About Chemistry before You Even Start . . . . . . . . . . . . 17 1.12. Combining Atoms to Make Molecules and Compounds . . . . . . . . . . . . . . . . . . 18 1.13. The Process of Making and Breaking Chemical Bonds: Chemical Reactions . 20 1.14. The Nature of Matter and States of Matter . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 22

Chapter 2. The Elements: Basic Building Blocks of Green Chemicals . . . . . . . . . . . 27 2.1. Elements, Atoms, and Atomic Theory . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 27 2.2. Hydrogen, the Simplest Atom . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 30 2.3. Helium, the First Noble Gas . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 33 2.4. Lithium, the First Metal . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 35 2.5. The Second Period of the Periodic Table . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 36 2.6. The Special Significance of the Octet of 8 Outer Shell Electrons . . . . . . . . . . . . 33 2.7. Completing the 20-Element Periodic Table . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 44 2.8. The Brief Periodic Table Is Complete . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 49

Chapter 3. Compounds: Safer Materials for a Safer World . . . . . . . . . . . . . . . . . . . . 55 3.1. Chemical Bonds and Compound Formation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 55 3.2. Electrons Involved in Chemical Bonds and Octets of Electrons . . . . . . . . . . . . . . 57 3.3. Sodium Chloride and Ionic Bonds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 58

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3.4. Covalent Bonds in H2 and Other Molecules . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 64 3.5. Covalent Bonds in Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 64 3.6. Covalent Bonds and Green Chemistry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 65 3.7. Predicting Covalently Bound Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 67 3.8. Chemical Formulas, the Mole, and Percentage Composition . . . . . . . . . . . . . . . . 71 3.9. What Are Chemical Compounds Called? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 73 3.10. Acids, Bases, and Salts . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 74

Chapter 4. Chemical Reactions: Making Materials Safely Without Damaging the Environment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 81

4.1. Describing What Happens With Chemical Equations . . . . . . . . . . . . . . . . . . . . . . 81 4.2. Balancing Chemical Equations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 83 4.3. Just Because You Can Write It Does Not Mean That It Will Happen . . . . . . . . . . 84 4.4. Yield and Atom Economy in Chemical Reactions . . . . . . . . . . . . . . . . . . . . . . . . 86 4.5. Catalysts That Make Reactions Go . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 87 4.6. Kinds of Chemical Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 88 4.7. Oxidation-Reduction Reactions and Green Chemistry . . . . . . . . . . . . . . . . . . . . . 90 4.8. Quantitative Information from Chemical Reactions . . . . . . . . . . . . . . . . . . . . . . . 93 4.9. Stoichiometry By the Mole Ratio Method . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 95 4.10. Limiting Reactant and Percent Yield . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 97 4.11. Titrations: Measuring Moles By Volumes of Solution . . . . . . . . . . . . . . . . . . . 98 4.12. Industrial Chemical Reactions: The Solvay Process . . . . . . . . . . . . . . . . . . . . 102

Chapter 5. The Wonderful World Of Carbon: Organic Chemistry and Biochemicals . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 109

5.1. Rings and Chains of Carbon Atoms . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 109 5.2. Compounds of Carbon and Hydrogen: Hydrocarbons . . . . . . . . . . . . . . . . . . . . 110 5.3. Lines Showing Organic Structural Formulas . . . . . . . . . . . . . . . . . . . . . . . . . . . 116 5.4. Functional Groups . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 118 5.5. Giant Molecules from Small Organic Molecules . . . . . . . . . . . . . . . . . . . . . . . . 123 5.6. Life Chemicals . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 126 5.7. Carbohydrates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 127 5.8. Proteins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 128 5.9. Lipids: Fats, Oils, and Hormones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 129 5.10. Nucleic Acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 131

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Chapter 6. Energy Relationships . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 133

6.1. Energy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 133 6.2. Radiant Energy from the Sun . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 136 6.3. Storage and Release of Energy By Chemicals . . . . . . . . . . . . . . . . . . . . . . . . . . 140 6.4. Energy Sources . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 142 6.5. Conversions Between Forms of Energy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 144 6.6. Green Engineering and Energy Conversion Efficiency . . . . . . . . . . . . . . . . . . . 147 6.7. Conversion of Chemical Energy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 148 6.8. Renewable Energy Sources . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 150 6.9. Nuclear Energy: Will it Rise Again? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .155

Chapter 7. Water, the Ultimate Green Solvent: Its Uses and Environmental Chemistry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 159

7.1. H2O: Simple Formula, Complex Molecule . . . . . . . . . . . . . . . . . . . . . . . . . . . . 162 7.2. Important Properties of Water . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 162 7.3. Water Distribution and Supply . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 163 7.4. Bodies of Water and Life in Water . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 164 7.5. Chemical Processes in Water . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 167 7.6. Fizzy Water from Underground . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 168 7.7. (Weak) Acid from the Sky . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 169 7.8. Why Natural Waters Contain Alkalinity and Calcium . . . . . . . . . . . . . . . . . . . . 170 7.9. Metals in Water . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 171 7.10. Water Interactions with Other Phases . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 171 7.11. Heavy Metal Water Pollutants . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 173 7.12. Inorganic Water Pollutants . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 175 7.13. Organic Water Pollutants . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 177 7.14. Pesticides in Water . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 179 7.15. Polychlorinated Biphenyls (PCBs) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 183 7.16. Radioactive Substances in Water . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 185 7.17. Water Treatment . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 185

Chapter 8. Air and the Atmosphere . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 195

8.1. More Than Just Air to Breathe . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 195 8.2. Atmospheric Chemistry and Photochemical Reactions . . . . . . . . . . . . . . . . . . . 199

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8.3. Energy and Mass Transfer in the Atmosphere . . . . . . . . . . . . . . . . . . . . . . . . . . 201 8.4. Atmospheric Oxygen and Nitrogen . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 204 8.5. Atmospheric Pollutant Particles . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 205 8.6. Pollutant Gaseous Oxides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 207 8.7. Acid Rain . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 210 8.8. Miscellaneous Gases in the Atmosphere . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 212 8.9. CO2: The Ultimate Air Pollutant? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 213 8.10. Photochemical Smog . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 217

Chapter 9. The Biosphere: How the Revolution in Biology Relates to Green Chemistry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 223

9.1. Green Chemistry and the Biosphere . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 223 9.2. Biology and the Biosphere . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 224 9.3. Cells: Basic Units of Life . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 227 9.4. Metabolism and Control in Organisms . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 229 9.5. Reproduction and Inherited Traits . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 233 9.6. Stability and Equilibrium of the Biosphere . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 233 9.7. DNA and the Human Genome . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 236 9.8. Genetic Engineering . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 240 9.9. Biological Interaction With Environmental Chemicals . . . . . . . . . . . . . . . . . . . 242 9.10. Biodegradation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 243 9.11. The Anthrosphere in Support of the Biosphere . . . . . . . . . . . . . . . . . . . . . . . . 245

Chapter 10. The Geosphere, Soil, and Food Production: The Second Green Revolution . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 251

10.1. The Solid Earth . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 251 10.2. Environmental Hazards of the Geosphere . . . . . . . . . . . . . . . . . . . . . . . . . . . . 253 10.3. Water in and on the Geosphere . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 256 10.4. Anthrospheric Influences on the Geosphere . . . . . . . . . . . . . . . . . . . . . . . . . . . 258 10.5. The Geosphere as a Waste Repository . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 259 10.6. Have You Thanked a Clod Today? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 260 10.7. Production of Food and Fiber on Soil -- Agriculture . . . . . . . . . . . . . . . . . . . . 263 10.8. Plant Nutrients and Fertilizers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 265 10.9. Pesticides and Agricultural Production . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 267

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