The 100 Most Important Chemical Compounds: A Reference Guide Richard L Myers GREENWOOD PRESS The 100 Most Important Chemical Compounds A Reference Guide Richard L Myers GREENWOOD PRESS Westport, Connecticut • London Library of Congress Cataloging-in-Publication Data Myers, Rusty L The 100 most important chemical compounds : a reference guide / Richard L Myers p cm Includes bibliographical references and index ISBN-13: 978–0–313–33758–1 (alk paper) ISBN-10: 0–313–33758–6 (alk paper) Chemicals—Dictionaries I Title II Title: One hundred most important chemical compounds TP9.M94 2007 540—dc22 2007014139 British Library Cataloguing in Publication Data is available Copyright © 2007 by Richard L Myers All rights reserved No portion of this book may be reproduced, by any process or technique, without the express written consent of the publisher Library of Congress Catalog Card Number: 2007014139 ISBN-13: 978–0–313–33758–1 ISBN-10: 0–313–33758–6 First published in 2007 Greenwood Press, 88 Post Road West, Westport, CT 06881 An imprint of Greenwood Publishing Group, Inc www.greenwood.com Printed in the United States of America The paper used in this book complies with the Permanent Paper Standard issued by the National Information Standards Organization (Z39.48–1984) 10 Dedicated to Catalina and Poco Contents Preface xi Acknowledgments xv Introduction 10 11 12 xvii What Is a Chemical Compound? xvii Types of Chemical Compounds xix Organic and Inorganic Compounds xix Ionic and Molecular Compounds xxi Naming Compounds xxi Molecular and Structural Formulas xxiv Entry Format xxv Acetic Acid Acetone Acetylene Acetylsalicylic Acid Adenine Adenosine Triphosphate (ATP) Adipic Acid Aluminum(III) Oxide Al2O3 Ammonia Ascorbic Acid Aspartame Benzene 10 13 18 20 24 27 30 33 36 viii | Contents 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 Benzoic Acid Biphenyl and PCBs Butane Butene Butyric and Fatty Acids Caffeine Calcium Carbonate Calcium Oxide (Lime) Calcium Sulfate (Gypsum) Carbon Dioxide Carbon Monoxide Chloroform Chlorophyll Cholesterol Citric Acid Cocaine Cytosine, Thymine, and Uracil DDT DEET Dichlorodifluoromethane, CFC-12 Dopamine, L-Dopa Epinephrine (Adrenaline) Ethane Ethene (Ethylene) Ether Ethyl Alcohol (Ethanol) Ethylenediaminetetraacetic Acid (EDTA) Fluoxetine (Prozac) Formaldehyde Formic Acid Glucose Glycerol (Glycerin) Guanine Hydrochloric Acid Hydrogen Peroxide Hydrogen Sulfide Ibuprofen Indigo Insulin 40 43 46 49 52 55 59 62 65 68 72 75 78 81 85 88 92 95 98 101 105 108 111 113 117 120 124 127 130 132 134 138 140 141 144 147 150 152 156 Contents 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 Iron(III) Oxide Isooctane Isoprene L-Dopa See 33 Dopamine, l-Dopa Methane Methyl Alcohol (Methanol) Methylphenidate (Ritalin) Monosodium Glutamate Morphine Naphthalene Nicotine Nitric Acid Nitric Oxide Nitrogen Dioxide Nitrous Oxide Nitroglycerin Norethindrone Penicillin Phenol Phosphoric Acid Piperine Potassium Carbonate Potassium Nitrate Propane Propylene Quinine Saccharin Silicon Dioxide (Silica) Sodium Bicarbonate Sodium Carbonate Sodium Chloride Sodium Hydroxide Sodium Hypochlorite Strychnine Styrene Sucrose Sulfuric Acid Tetrafluoroethylene Tetrahydrocannabinol (THC) 160 164 167 171 171 174 178 181 184 188 191 194 197 197 197 202 205 209 214 218 221 224 227 231 234 238 241 244 247 249 252 257 260 263 266 268 271 275 278 | ix 314 | Glossary polymerization Process used to produce polymers porphyrin Structure of four pyrrole rings linked on opposite sides by four methine bridges pyridine ring Benzene with a nitrogen atom substituted for one of the hydrogen atoms, C6H5N pyrimidine Heterocyclic aromatic compound, pyrolysis Heating in low-oxygen atmosphere to break down a compound pyrrole C4H5N, pyrrolidine C4H9N, quarternary carbon A carbon atom bonded to four other carbon atoms by single bonds racemate A mixture of equal amounts of right-handed and left-handed enantiomers of a chiral compound racemic mixture Compound consisting of equal mixtures of levorotatory and dextrorota- tory reduction Process involving the gain of electrons reforming Process in which naphthas are converted into higher octane isoparaffins and aro- matics resin Sticky liquid organic substance exuded from plants that harden on exposure to air scrubber Device used to remove air pollutants from stacks and industrial exhausts steam reforming Method used to produce hydrogen by reacting methane with steam stereo isomers Molecules of the same compound with different spatial arrangements synaptic neurons Nerve cells that transmit information; information moves from presynaptic neuron to postsynaptic neuron tachycardia Abnormal rapid heart rate tacticity Arrangement of units along a chain in macromolecule or a polymer thermal cracking Use of high temperature (and pressure) to break hydrocarbons into smaller compounds transition metal An element with an incomplete d subshell or one that forms a cation with an incomplete d subshell Ziegler-Natta catalyst Organometallic compounds used in vinyl polymerization to control tacticity Selected Bibliography Aftalion, Fred A History of the International Chemistry Industry, 2nd ed Philadelphia: Chemical Heritage Foundation, 2001 Atkins, Peter William Molecules New York: Scientific American Library, 1987 Baird, Colin, and Michael Cann Environmental Chemistry, 3rd ed New York: W H Freeman and Company, 2004 Baker, David A., and Robert Engel Organic Chemistry St Paul: West Publishing Company, 1992 Brock, William H The Norton History of Chemistry New York: W W Norton and Company, 1993 Cambridge Soft Corporation ChemFinder.com The Web site is a searchable database giving structure, physical data, and links to other sites on compounds Chang, Raymond Chemistry, 7th ed Boston: McGraw-Hill, Inc., 2002 Chemical & Engineering News Top Pharmaceuticals 83(25): 44–139 Special issue published on June 20, 2005 devoted to reports on 46 of the most important drugs for human society Chemical Heritage Foundation This organization is devoted to preserving the history of chemistry Chemical Land21.com An industrial supplier that provides a comprehensive list of compounds with their structures, selected physical properties, and a general description Chemical Technology, An Encyclopedic Treatment New York: Barnes and Noble Books, 1972 Chenier, Philip J Survey of Industrial Chemistry, 3rd ed New York: Kluwer Academic/Plenum Publishers, 2002 Downing, Ralph C Fluorocarbon Refrigerants Handbook Upper Saddle River, NJ: Prentice Hall, 1988 Drug Enforcement Administration, Department of Justice Drugs of Abuse Provides general background information on illegal drugs 316 | Selected Bibliography European Fertilizer Manufacturers Association Best Available Techniques for Pollution Prevention and Control in the European Fertilizer Industry 2000 A comprehensive site with a wealth of information on ammonium, sulfuric acid, nitrates, and other compounds involved in making fertilizer The Formaldehyde Council, Inc Devoted to the uses, health and safety, and facts about formaldehyde Furniss, Brian S., Anthony J Hannaford, Peter W G Smith, and Austin R Tatchell Vogel’s Textbook of Practical Organic Chemistry, 5th ed Harlow: Longman Scientific & Technical, 1989 Garfield, Simon Mauve London: Faber and Faber Limited, 2000 Giunta, Carmen Selected Classic Papers from the History of Chemistry A site to access classical papers in the history of chemistry Guyton, Arthur C., and John E Hall Human Physiology and Mechanisms of Disease, 6th ed Philadelphia: W B Saunders, 1977 Hopp, Vollrath, and Ingo Hennig Handbook of Applied Chemistry Washington: Hemisphere Publishing Corporation, 1983 Hounshell, David A., and John Kenly Smith, Jr “The Nylon Drama.” Invention and Technology, Fall, 1988: 40–55 Idhe, Aaron J The Development of Modern Chemistry New York: Harper and Row, 1964 IMA Europe European site devoted to industrial minerals such as gypsum, calcium carbonate, and so forth International Directory of Company Histories Detroit: St James Press, 1988 Kent, James A Riegel ’s Handbook of Industrial Chemistry, 10th ed New York: Kluwer Academic/Plenum, 2003 Kirk-Othmer Encyclopedia of Chemical Technology, 5th ed New York: John Wiley & Sons Inc., 2004 Kress, Henriette King’s American Dispensatory by Harvey Wickes Felter and John Uri Lyold, 1898 February 8, 2002 A comprehensive work describing medicinal plants used at the beginning of the 20th century This pharmacopeia gives the history of natural compounds used from antiquity until the 20th century Landenburg, A Lectures on the History of the Development of Chemistry Since the Time of Lavoisier Translated by Leonard Dobbin Chicago: University of Chicago Press, 1911 LeCouteur, Penny, and Jay Burreson Napolean’s Buttons New York: Jeremy P Tarcher, 2003 May, Paul The Molecule of the Month Information and links on over 100 chemical compounds MayoClinic Clinic’s Web site provides background information on various diseases, conditions, and pharmaceuticals The Merck Index, 12th ed Whitehouse Station, NJ: Merck & Co Inc., 1996 Molecules Links to a journal of synthetic organic chemistry and natural products Provides scholarly articles on various compounds Morrison, Robert Thornton, and Robert Neilson Boyd Organic Chemistry Boston: Allyn and Bacon, Inc., 1959 Multhauf, Robert P Neptune’s Gift Baltimore: The John Hopkins Press, 1978 Myers, Richard L The Basics of Chemistry Westport, CT: Greenwood Press, 2003 National Institute of Health Third Report of the National Cholesterol Education Program September 2002 Comprehensive findings on research on cholesterol and health Selected Bibliography | National Lime Association Chemistry, uses, and production of various forms of lime National Toxicology Program, Department of Health and Human Services 11th Report on Carcinogens Overview of numerous carcinogenic compounds giving uses, production, exposure, and properties of these compounds The Nobel Foundation Acceptance speeches and background information on Nobel laureates Parker, Sybil P., Ed McGraw-Hill Dictionary of Chemical Terms New York: McGraw Hill Book Company, 1985 Plastics and Chemical Industries Association Chemical Fact Sheets Physical data, chemistry, and production processes of numerous chemical compounds Raven, Peter H., and George B Johnson Biology, 4th ed Dubuque, IA: Wm C Brown Publishers, 1996 Reusch, William Virtual Textbook of Organic Chemistry 1999 A comprehensive online text of organic chemistry Schatz, Paul W “Indigo and Tyrian Purple-In Nature and in the Lab.” Journal of Chemical Education 78 (November, 2001):1442–43 Sidgwick, N V The Chemical Elements and Their Compounds Volume I and Volume II Oxford: Clarendon Press, 1930 Snyder, Carl H The Extraordinary Chemistry of Ordinary Things, 3rd ed New York: John Wiley & Sons Inc., 1998 The Soap and Detergent Association Technology Information Group Chemical Market Reporter, Chemical Profiles http://www the-innovation-group.com/chemprofile.htm Production statistics and data on producers of various industrial compounds 3DChem.Com Chemistry, Structures and 3D Molecules Comprehensive site on compounds giving the top 50 pharmaceuticals, molecule of the month, and structures on more than 1,600 compounds Tobin, Allan J., and Jennie Dusheck Asking About Life Fort Worth, TX: Saunders College Publishing, 1998 United States Department of Energy Depleted UF6 Management Information Network Information on uranium compounds United States Energy Information Administration Gives information on alternative fuels such as ethanol, methanol, and pollutants United States Environmental Protection Agency Information on air pollutants such as nitrogen oxides, greenhouse gases, CFC’s, and toxic chemicals United States Geological Survey Minerals Yearbook Volume I—Metals and Minerals Background information and production statistics on various mineral compounds such as soda ash, salt, gypsum, etc Voet, Donald, Judith G Voet, and Charlotte W Pratt Fundamentals of Biochemistry Upgrade Edition New York: John Wiley & Sons, 2002 Walsh, Christopher Antibiotics: Actions, Origins, Resistance Herndon, VA: ASM Press, 2003 317 Index Abel, John Jacob, 108 Acetaldehyde, 121, 123, 233, 275 Acetic anhydride, 3, 123 Acetone cyanohydrin, Acetyl coenzyme A (CoA), 19 Acetylene torch, Acetylsalicylic acid, 10 –12 Acid precipitation, 274 Acrylonitrile, 169, 234 Adams, Stewart, 150 Adderall, 180 Adenine, 13 –16, 18, 93 – 94 Adenosine, 13 Adenosine diphosphate (ADP), 16 Adenosine triphosphate (ATP), 18 –19 Adipic acid, 20 –23 Albius, Edmond, 292 Alcoholic drinks, 120, 122 Aldrich, Thomas Bell, 108 “Alkali Acts” (1853), 250 Al-razi, Mohammad Ibn Zakariya, 271 Alumina, 24 –26 Ammonia, 27–29; in nitrification, 228 Ammonium carbamate, 289 Ammonium diuranate, 285–86 Anaerobic respiration, 147– 48 Anaphylaxis, 110 Angina pectoris, 204 Aniline, 39, 154 Antacid, 12, 143 Anthrahydroquinone, 144 Antiepilepsirine, 223 Apoliprotein, 82 Aqua regia, 196 Aragonite, 59 Archard, Franz Karl, 269 Arm and Hammer, 248 Artificial vanilla, 293 Aspartame, 133, 270 Aspartic acid, 34, 270 Aspirin, 10, 12 Atactic, 234 –35 Attention-deficit hyperactivity disorder, 178–79; and caffeine, 58; and nicotine, 193 Baekeland, Leo Hendrik, 131, 216 Baeyer, Adolph von, 155, 290 Baeyer, Friedlich, 11 Bakelite, 131, 216 Baking soda, 247– 48 Banting, Fredrick G., 157 Barbituric acid, 290 Base pairing, 15, 93 Baumann, Eugen, 295 Bayer, Karl Josef, 23 Bayer process, 23 Benadryl, 128 Benzaldehyde, 41, 284 Benzene derivatives, 38 Benzene sulfonic acid, 215 Benzoin, 36, 40 Benzoyl chloride, 42 Bergman, Torbern, 27 Bernigaut, Louis Marie Hilaire, 21 Bersworth, Frederick C., 125 Berthelot, Marcellin, 7, 132 320 | Index Berthier, Pierre, 24 Berthollet, Claude Louis, 27, 147 Berzelius, Jöns Jakob, 132, 288 Best, Charles Herbert, 158 B F Goodrich Company: polyvinyl chloride, 295 –96 Biological magnification, 96 Bisphenol A (BPA), 5, 216 Black, Joseph, 68 Bleach, 259 – 62; and EDTA, 126 Blood, buffering of, 70 Blyth, John, 266 Bosch, Karl, 28 Boyer, Paul D., 19 Boyle, Robert, 171, 174 Brand, Henning, 219 Breeder reactor, 287 BTEX, 303 – Burnt lime, 62 Burrows, Colin, 150 Butadiene, 9, 51; in rubber, 169 –70 Butanediol, Butlerov, Aleksandr, 130 Caffeine, 55 –58; content of food, 57 Calcination, 62, 65 Calcite, 59 Calcium acetate, Calcium carbide, 7– 8, 64 Calcium carbonate equivalent, 60 Calcium hydroxide See Slaked lime Cannabis, 278 –79 Canventou, Joseph Bienaimé, 79 Caprolactam, 216 –17 Capsaicin, 222–23 Carbaryl, 189 Carbohydrate, 70, 134; in human diet, 136 Carbonation of beverages, 69 Carbon dioxide, 68 –71; phase diagram, 70 Carbonic acid, 70, 273 Carlsson, Arvid, 106 Caro’s acid, 145 Carothers, Wallace Hume, 22 Carson, Rachael, 96 Castner, Hamilton Young, 257 Catechol 110; vanilla synthesis, 293 Catecholamines, 110 Cathodic protection, 162 Cavendish, Henry, 298 Cellulase, 136 Cellulose, 136 Cellulose acetate butyrate, 53 Chain, Ernest Boris, 211 Chelation, 124 –25 Chelation therapy, 126 Chevreul, Michel Eugène, 81 Chilean Saltpeter, 227, 229 –30 Chinese restaurant syndrome, 183 Chlorophyll, 78 – 81 Cholesterol, 81– 84; in common foods, 82 Chromophores, 261 Church, Austin, 248 Cinchonism, 239 Cis Configuration, 49, 54 Claus process, 148 Clorox, 261 Coal tar, 188 Coca-Cola, 90 Codeine, 186 – 87 Coffee, 55 Collip, James Bertram, 158 Coniferin, 293 Contraceptives, 204 – Cook, Captain James, 31 CO poisoning, 73 Cordite, Cordus, Valerius, 117 Corrosion, 162 Cortez, Hernando, 291 Corundum, 24, 26 Cotinine, 192 Cotzias, George C., 106 Cox inhibitor, 150 Crack cocaine, 90 Crawford, Albert C., 108 Crépieux, P., 192 Cruikshank, William Cumberland, 72 Crutzen, Paul, 103 Cumene, 5, 38 Currie, James A., 86 Cyclamates, 270 Cyclohexanol, 22 Cyclohexanone, 22 Cyclooxygenase (COX), 12, 150 Cyclopropane, 233 Cyclotrimethylenetrinitramine (RDX), 282 Da Gama, Vasco, 30 Davy, Edmund, Davy, Humphrey, 199 “D” Configuration, 134 de la Salle, Poulletier, 81 de Lassone, Joseph Marie François, 72 de Saussure, Nicholas Theodore, 79 de Vigenère, Blaise, 40 Decaffeination, 57 Index DEET, 98 –100 Deoxyribonucleic acid (DNA), 13 –16, 93 –94 Derosne, Jean François, 184 Deuterium, 148, 287 Dexter, 135 Diabetes, 137, 157–59 Dibenzofuran, 45 Diethylamine, 98 Dimethyl ketone, Dimethyl terephthalate (DMT), 175 Diosgenin, 206 –7 Dioxin, 45, 297 Diphenylhydramine, 128 Diphosphoric acid, 219 Dipropylene glycol dibenzoate, 42 Direct methanol fuel cell, 176 Djerassi, Carl, 207 Döbereiner, Johann Wolfgang, 56 Doering, William von E., 239 Dow Chemical Company, 261 Dow, Herbert Henry, 261 Drewson, Viggo, 155 Drierite, 66 Dry ice, 69 Duchesne, Ernest, 210 Dumas, Jean-Baptiste André, 4, 135 DuPont: CFCs, 101; synthetic fabrics 22; Teflon, 115, 275 –76 du Pont, Eleuthè Iréneé, 229 Dutrochet, René-Joachim-Henri, 79 Dwight, John, 248 Dynamite, 203 Eastman, George, 131, 216 Eau de Labarraque, 260 Edgar, Graham, 165 E85, 123 Empedocles, 298 Encephalitis lethargica, 106 Endothelium-derived relaxing factor (EDRF), 201 Epichlorohydrin, 139 Epinephrine, 108 –10 Epoxide ring, 145 – 46 Erlenmeyer, Richard August Carl Emil, 188 Ethylbenzene, 116, 266 Ethyl benzoate, 42 Ethylenediamine tetraacetic acid (EDTA), 124 –26 Ethylene oxide, 115 Eugenol, 293 Extractive distillation, 50 Faber, Herbert, 151 Fahlberg, Constantin, 241 Familial hypercholesterolemia, 83 Faraday, Michael, 36, 111, 167, 188 Fatty acid, 52–54 Fermentation, 121 Fertilizer, 195, 219, 272 Fischer, Emil, 290 Fischer, Franz, 73 Fischer, Hans, 79 Fisher, Samuel, 132 Fleming, Alexander, 210 Florey, Howard Walter, 211 Flourens, Marie Jean Pierre, 75 Formate, 76, 133 Formica company, 131 Frankland, Edward, 111 Freon, 101–2 Freud, Sigmund, 89 Frobenius, August Siegmund, 117 Frohlich, Theodore, 31 Fuller, Ray W., 127 Fuming nitric acid, 194–95 Funk, Casmir, 105 Furan, 45 Gabelle, 253 Gaedcke, Friedrich, 89 Gahn, Johann, 219 Gamma-aminobutyric acid, 54 Gaoni, Yehiel, 279 Garden, Alexander, 188 Gasohol, 123 Gasoline, 164 – 66 Gates, Marshall D., 187 Gay-Lussac, Joseph Louis, 132, 185, 272 Geber, 85, 141, 194 Geometric isomers, 49 Gerhardt, Charles Frederic, 10–11, 214 Girdler-Sulfide (G-S) process, 148 Glacial acetic acid, Glass, 63 Glauber, Johann Rudolph, 214, 229 Global warming potential, 173 Glover, John, 272 Glucogenesis, 137 Glutamate, 181 Glycerine, 138 Glycerol, 138–39 Glycine, 264 Glycogen, 137 Glycogenesis, 137 Glycolysis, 19, 136 Gobley, Nicholas-Theodore, 292 Goethe, Johann Wolfgang von, 56 | 321 322 | Index Goodyear, Charles, 168 Gore, Wilbert, 277 Gore-Tex, 277 Government rubber styrene (GR-S), 169 Greenhouse gas, 71, 173, 200 Grégoire, Marc, 276 Gregory,William, 167 Grignard reagent, 118 –19 Ground calcium carbonate, 60 Guaiacol, 293 Guanine, 13, 15, 93 –94, 140 –41 Guano, 140 Guggenheim, Marcus, 106 Gulland, John Masson, 187 Guthrie, Samuel, 75 Haarmann, Wilhelm, 293 Haber, Fritz, 28, 230 Haber-Bosch process, 28 Haber process, 28 Halite, 252, 254 Hall, Charles Martin, 258 Hall-Héroult process, 258 Halons, 103 Hardie, Thomas G., 276 Hartmann, Max, 178 Haworth, Norman, 31 Hayes, Arthur, 34 Heatley, Norman, 211 Heavy water, 148; reactor, 287 Hemolytic anemia, 189 Henne, Albert Leon, 102 Herodotus, 50, 279 Heroin, 12, 186 Héroult, Paul L T., 25, 258 Heumann, Karl Von, 155 Hexuronic acid, 31 High-density lipoprotein (HDL), 82 High-density polyethylene (HDPE), 51, 115, 236 Hill, Julian, 22 Hippocrates, 1, 10 Hirst, Edmund, 31 Hodgkin, Dorothy Mary Crowfoot, 213 Hoffman, Felix, 11 Hoffmann, August Wilhelm von, 130, 266 Holst, Alex, 31 Holtz, Peter, 106 Hooke, Robert, 20 Hopkins, Samuel, 225 Hydrochlorofluorocabon (HCFC), 75 –76 Hydrogen bonding, 299 –300 Hydrogen sulfide, 147– 49 Hypoglycemia, 159 Ibn Haygan, Jabir (Geber), 85, 141, 194 Ikeda, Kikunae, 182 Indican, 153 Indigo carmine, 155 Indigotine, 155 Indole-3 butyric acid, 54 Indoxyl, 259 Ingenhousz, Jan, 79 Iron Age, 160 Iron, smelting, 160 Islets of Langerhans, 157 Isobutane, 46 – 47 Isobutylene, 47, 51 Isoeugenol, 293 Isooctane, 47, 50, 164 – 66 Isopropyl alcohol, 236 Isotactic, 235 Jackson, Charles T., 118 Jesuit powder, 238 Johnson, Treat B., 94 Kellner, Karl, 257 Ketosis, Kidd, John, 188 King, Charles G., 31 Klatte, Friedrich Heinrich August, 295 Knowles, William S., 107 Kolbe, Adolph Wilhelm Hermann, 111 Kolbe synthesis, 111 Kossel, Albrecht, 140 Kraft bleaching, 145 Kraft pulp, 145 Krebs, Hans Adolf, 18 Krebs cycle 17, 19, 87 Labarraque, Antoine Germaine, 260 Ladenburg, Albert, 222 Laevus, 135 Langerhans, Paul, 157 Laughing gas, 198 –99 Lauric acid, 52 Laveran, Charles Louis Alphonse, 238 Lavoisier, Antoinne, 66, 229, 298 Lawes, John Bennett, 219 “L” Configuration, 134 Leblanc, Nicolas, 250 Leblanc process, 250 Le Chatelier, Henry-Louis, 8, 28 Leucoindigo, 154 L-glucose, 134 Lieben, Adolf, 52 Liebig, Justus von, 4, 40, 75 Index Ligand, 210 Lilly, Eli: Prozac, 128 Lime causticization, 257 Lind, James, 28 Lipman, Fritz, 18 Liquefied petroleum gas (LPG), 46 Liquer de Javel, 260 List, Adolf, 241 Lister, Joseph, 210, 214 Long, Crawford Williamson, 118 Low density lipoprotein (LDL), 82 Low density polyethylene (LDPE), 51, 114, 235 –36 Lullus, Raymundus, 117 Lysozyme, 210 Macleod, John James Richard, 157–58 Malaria, 238 – 40 Marggraf, Andreas Sigismund, 135 Mariani, Angelo, 89 Marijuana, 279– 80; medical, 279 Marker, Russell Earl, 206 Maumee Process, 243 Mauve, 155 Mazur, Robert Henry, 33 McCormick, Cyrus, 208 McCormick, Katherine, 208 McIntire, Ray, 267 McNary, Robert Reed, 102 Mechoulam, Raphael, 279 Mehring, Joseph von, 290 Melamine, 289–90 Melsens, Louis Henri, 192 Metallocene catalyst, 235 Methane, 171–73; hydrate, 173 Methanogenesis, 171 Methanol, 174 –77; poisoning, 174 –75 Methyl benzoate, 42 Methyl ethyl ketone (MEK), 51 Methyl methacrylate (MMA), Midgley, Thomas, 101–2, 165 Miramontes, Luis Ernesto, 207 Mitscherlich, Eilhardt, 36 Molina, Mario, 102 Molloy, Bryan B., 127 Monsanto: company, 242; aspartame, 34; PCBs, 43 – 45 Montreal Protocol, 76, 103, 142 Morgan, Hugh, 292 Morphine rule, 185 Morren, Charles François Antoine, 292 Morren, Marcel, Mortar, 63 Morton, William Thomas Green, 118 Moyer, Andrew J., 212 M-toluoyl chloride, 98 See also DEET Müller, Paul, 95 Münz, Ferdinand, 125 Muriatic acid, 141 Mylar, 304 Nahcolite, 247 Naphthalene, 155, 188 –90 Natta, Giulio, 170 Neumann, A., 94 Niacin, 19, 192 Nicholas-Vauquelin, Louis, 192 Nicholson, John, 150 Nicot, Jean, 191 Nicotinamide adenine dinucleotide phosphate hydrogen (NADPH), 80 Nicotine, 191–93 Nicotinic acid, 192 Niemann, Albert, 89 Nitrobenzene, 38 Nobel, Alfred, 202–3 Nobel, Emil, 203 Nobel, Immanuel, 202–3 Norepinephrine, 109, 179 Norethynodrel, 207–8 NO synthase (NOS), 201 Nuclear power, 286 Nucleoside, 93 Nucleotide, 14–15 Nutra-Sweet, 270 Nylon, 20, 22 O’Conor, Daniel, 131 Octane number, 50, 123, 166 Oersted, Han Christian, 222 Oleic acid, 53 Oliver, George, 108 Omega-3 fatty acid, 53, 84 Opium, 184–85 Opium Wars, 185 Ortho-xylene, 303 Ostwald, Wilhelm, 194 Ostwald method, 194 – 95 Oxidative phosphorylation, 19 Ozone, 103 Palmitic acid, 53 Panizzon, Leandro, 178 Paracelsus, 117, 184 Para-xylene, 303 Parkinson, James, 106 | 323 324 | Index Parkinson’s disease, 106 Pasteur, Louis, 214, 260 PCB numbering system, 44 Pearlash, 224 Pellagra, 192 Pelletier, Pierre-Joseph, 79 Pelouze, Théophile-Jules, 138 Pemberton, John Smith, 90 Pentaerythritol tetranitrate (PETN), 282 Pepper, 221–23 Peptidoglycan, 209 Peracetic acid, 145 Perchloroethylene (PERC), 70, 115 Perfluorooctanoic acid, 276 Perkins, William Henry, 154 pH, 301 Phillip II of Spain (king), 89 Phenylalanine, 34–35, 270 Phenylketonuria, 34, 270 Phillips, Frank, 232 Phillips, Peregrine, 272 Phosphoric acid, 218 –20 Photosynthesis, 70, 78 – 80 Photosystem, 79 Phthalic acid, 304 Phthalic anhydride, 189 Picric acid, 281– 82 Pictet, Amé, 192 Pig iron, 161 Pincus, Luis, 207 Piperine, 221–23 Plant pigments, 80 Plaster of Paris, 65– 66 Pliny the Elder, Plunkett, Roy J., 275 pOH, 301 Polychlorinated biphenyl (PCB), 43 – 44 Polyethylene terephthalate (PET), 175, 304 Polytetrafluoroethylene (PTFE), 115, 275 –76 Polyvinyl chloride, 295 –97 Portland cement, 63 Posselt, Wilhelm, 192 Potash, 141, 224 –25, 229 Precipitated calcium carbonate (PCC), 60, 64 Priestley, Joseph: ammonia, 27; carbon dioxide, 69; carbon monoxide, 72; chlorophyll, 78 –79; isoprene; 167; nitrogen oxides, 199; water, 298 Progesterone, 206 – Propionic acid, 48, 231 Propylene oxide, 237 Propylene oxide/styrene monomer process (PO/SM), 266 Prozac, 127–29 Purine, 13 Pyrimidine, 93 Pyrolysis, 112 Pyrolysis gas, 39 Pyrrole, 78, Pyruvate, 19, 136 Queeny, John Francis, 242 Quinine, 238–40; and indigo, 154 Ramazzini, Bernardino, 148 Rayon, 21 Rebok, Jack, 275 Regnault, Henri-Victor, 295 Reichstein, Thadeus, 31 Reichstein process, 31 Reimann, Karl Ludwig, 192 Reimer, Karl, 293 Remsen, Ira, 241 Remsen-Fahlberg process, 243 Reppe process, Ribonucleic acid (RNA), 13 –16, 93 –94 Ribose, 13 –14 Ritalin, 178–79 Ritthausen, Karl Heinrich, 182 Robinson, Frank, 263 Robinson, Robert, 187 Rock, John, 208 Roebuck, John, 272 Roselius, Ludwig, 57 Rosenkranz, George, 207 Ross, Ronald, 238 Rossi, Antonio, 52 Rouelle, Hilaire Marin, 288 Rowland, F Sherwood, 102 Royal Demolition Explosive, 282 Rubber, 51, 167–70 Rügheimer, Leopold, 222 Runge, Friedlieb Ferdinand, 56 Rust, 160 – 61 Sabatier, Paul, 172 Sabatier process, 172 Saccharin, 241– 43 Sachs, Oliver, 106 Sainte-Claire Deville, Henri-Etienne, 283 Salicin, 11 Salicylic acid, 11 Salt, 252–56 Saltpeter, 227–30 Salt tax, 253 Sanger, Margaret, 208 Saponification, 138 Index Sarsasapogenin, 206 Scheele, Carl Wilhelm, 85, 138, 147, 219, 260 Schlatter, James M., 33 Schmiegel, Klaus K., 127 Scholtz, M., 222 Schweppe, Jacob, 69 Scoville, Wilbur L., 223 Scoville Organoleptic Scale, 223 Scurvy, 30 –31 Sea salt, 254 Seguin, Armand, 185 Selective serotonin uptake inhibitor (SSRI), 127 Semon, Waldo Lonsbury, 295 Senebier, Jean, 79 Serotonin syndrome, 129 Sertürner, Friedrich Wilhelm, 185 Sharpley-Schaffer, Edward Albert, 108 Sheehan, John C., 214 Sherwin-Williams method, 243 Simon, Eduard, 265 Simpson, James Young, 75 Skou, Jens C., 19 Slaked lime, 63 Smith, Adam, 253 Snelling, Walter, 232 Sobrero, Ascanio, 202 Soda, 63, 69, 245 Soda ash, 225, 249–51 Sodium benzoate, 41 Sodium chloride, 252–56 Sodium salicylate, 11 Solution mining, 247, 253 –54 Solvay, Ernest, 29, 250 Solvay process, 29, 69, 142, 247, 250 Souberian, Eugéne, 75 Sour natural gas, 147 Starch, 134, 137 Statin, 84 Staudinger, Hermann, 266 Stearic acid, 52 Steel, 161– 62 Steroid, 205 Stomach acid, 137, 142 Stork, Gilbert, 239 Stradonitz, August Kekulé von, 36 Sucralose, 270 Sugar, 268–70 Sulfuric acid, lead-chamber process, 271–74 Supercritical fluid, 69 Superphosphate fertilizer, 219 Superphosphoric acid, 218 Swarts, Frédéric, 101 Sweet-N-Low, 242 Syndiotactic, 234 Syn gas, 172 Syntex, 206 Szent-Györgyi, Albert, 31 Tacticity, 234, 313 Takamine, Jokichi, 108 Tefal, 276 Teflon, 115, 275–77 Tennant, Charles, 260 Terephthalic Acid, 304 Tetrafluoroethylene (TFE), 275 –77 Tetrahydrocannabinol (THC), 278 – 80 T-fal, 276 Thenard, Louis-Jacques, 144 Theophrastus, 69 Thilorier, Charles, 69 Tiemann, Ferdinand, 292 Tobacco, 191–93 Todd, Alexander, 18 Toluene, 283–84; in benzene production, 39; in benzoic acid, 41 Toluene disproportionation, 39 Toluene hydrodealkylation, 39 Toluene 2,4-diisocyanate, 284 Toluene 2,6-diisocyanate, 284 Tonic water, 240 Topham, Charles, 21 Trichloroacetaldehyde, 76 Trichloroacetone, 76 Tricyclic antidepressant, 127 Triglyceride, 138; and cholesterol, 83; and soap, 259 Trihalomethanes, 77 Trinitrotoluene (TNT), 281–82 Triple superphosphate (TSP), 273 Triuranium octaoxide, 285–87 Trona, 247, 249 Tropsch, Hans, 73 Tschudi, Gilg, 187 Tsvett, Mikhail Semenovich, 79 2-ethyl anthrahydroquinone, 145 2-nitrobenzaldehyde, 155 Uenaka, Keizo, 108 Umami, 182 Uranium hexafluoride, 286 Uranyl nitrate hexahydrate, 286 Urea, 288 –90 Van Helmont, Jan Baptista, 68 Vanilla, 291–94 Vanilloid, 222; receptor, 222 | 325 326 | Index Veillon, Louis, 242 Very-low-density lipoprotein (VLDL), 82 Villanova, Arnold of, 72 Vinegar, 1–3 Vinyl acetate, 115 Vinyl chloride, 9, 115, 142, 295 –97 Vitamin C, 30 –32 Volta, Alessandro, 171 Vulcanization, 168 Walker, John E., 19 Walter, Phillipe, 283 Washing soda, 69, 249, 251 Water, 298–302; phase diagram, 300 Watt, Charles, 257 Wehmer, Carl, 86 Weizmann, Chaim, Wells, Horace, 118 Wheeler, Henry Lord, 94 Wickham, Henry, 169 Wilbrand, Joseph, 281 Wiley, Harvey W., 242 Williams, Charles Hanson Greville, 167 Williamson Synthesis, 119 Willson, Thomas, Willstätter, Richard Martin, 79 Woad, 152 Wöhler, Friedrich, 40, 288 Wong, David T., 127 Woodward, Robert Burns, 239 Wray, John, 132 Wright, C R Alder, 186 Xylene, 39, 303 –5 Yellow cake, 285 Ziegler, Karl, 170 About the Author RICHARD L MYERS is Professor of Environmental Science at Alaska Pacific University He has taught chemistry, oceanography, meteorology, and physics classes and conducted research on urban environmental issues His work has appeared in the Journal of Environmental Health, The Northern Engineer, Journal of Chemical Education, and Journal of College Science Teaching His teaching awards include the Carnegie Foundation Alaska Professor of the Year, Higher Education Award from the United Methodist Church, President’s Forum Teaching Award, and Ohaus Award for Innovations in College Science Teaching He teaches undergraduate and graduate courses in chemistry, statistics, and environmental science Dr Myers’ published research includes work on air quality, water quality, science education, and science and the humanities ... leading to their 1899 patent for a drug they called aspirin, the most used medicine since 1900 The story of aspirin and 99 other compounds is the subject of The 100 Most Important Chemical Compounds:... Teflon, T-fal, and ibuprofen appear, helping the reader relate to the material Numerous stories involving the 100 chemicals are included in The 100 Most Important Chemical Compounds so that the reader... of these compounds is unique, but collectively they shape our physical world The 100 Most Important Chemical Compounds introduces the reader to the most notable of these compounds I hope the