Iodine Chemistry and Applications - 2014 - Kaiho - Front Matter

Iodine Chemistry
and Applications
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Iodine Chemistry
and Applications
Tatsuo Kaiho
Edited by
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Published by John Wiley & Sons, Inc., Hoboken, New Jersey
Published simultaneously in Canada
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Library of Congress Cataloging-in-Publication Data:

Kaiho, Tatsuo.
Iodine chemistry and applications / edited by Dr. Tatsuo Kaiho, Kanto Natural Gas Development Co.,
Ltd., Brine Resources R&D Division, Chiba, Japan.
pages cm
Includes index.
ISBN 978-1-118-46629-2 (cloth)
1. Iodine. 2. Iodine–Industrial applications. 3. Iodine–Therapeutic use. I. Title.
TP245.I6K35 2014
661′.1–dc23
2014017643
Cover Image: Courtesy of Tatsuo Kaiho
Printed in the United States of America
10 9 8 7 6 5 4 3 2 1
LIST OF CONTRIBUTORSix
xiii
15
25
55
75
v
Characteristics, elemental of iodine
3 Analytical Methods for Iodine and Iodides

Hirofumi Kanoh and Takehisa Konishi
Physical Properties of Iodine
Ion Chromatography
CONTENTS
Inorganic Iodides
Organic Iodides
Tsugio Kitamura
Anna Błaz ̇ewicz
Overview
Tatsuo Kaiho
Tatsuo Kaiho
Tatsuo Kaiho
Preface
Part I
1

viCONTENTS
7 Hypervalent Iodine 103

Toshifumi Dohi and Yasuyuki Kita
8 Iodine and Halogen Bonding 159

Giancarlo Terraneo, Giuseppe Resnati, and Pierangelo Metrangolo
Part II Production of iodine 195
9 History of Iodine 197

James L. Marshall and Virginia R. Marshall
10 Production Process in the Past 207

Tatsuo Kaiho
11 Iodine Production from Caliche 213

Armin Lauterbach
12 Iodine Production from Oilfield Brine 221

Stanley T. Krukowski
13 Iodine Production from Natural Gas Brine 231

Nobuyuki Kaneko and Tatsuo Kaiho
14 Recycling of Iodine 243

Tatsuo Kaiho
Part III Synthesis of iodine compounds 249
15 Iodinating Reagents 251

Haruhiko Taguchi
16 Oxidizing Agents 277

17 Reaction of Iodo Compounds 303

18 Metal Iodides–Mediated Reaction 329

Makoto Shimizu, Iwao Hachiya, and Junji Inanaga
CONTENTS vii
Part IV Biological Application of iodine 353
19 Iodinated X-Ray Contrast Agents 355

Werner Krause
20 Iodine as Disinfectant 375

Waldemar Gottardi
21 Synthetic Thyroid Hormone 411

Steven E. Rokita
22 Iodine Deficiency Disorders and Their Correction

Using Iodized Salt and/or Iodine Supplements 421
Michael B. Zimmermann
23 Pharmaceuticals: Therapeutic Agents 433

Tatsuo Kaiho
24 Agrochemicals and Anthelmintics 439

Peter Jeschke and Tatsuo Kaiho
Part V Industrial Application of iodine 457
25 Diaryliodonium Salt Photoacid Generators 459

James V. Crivello
26 Polarizing Films 479

Bart Kahr and Kevin M. Knowles
27 Iodine in Polymer Synthesis: An Important Element

for Precision Polymerizations 489
Mitsuo Sawamoto
28 Iodine in Dye-Sensitized Solar Cells 501

Lars Kloo
29 Fluorinated Repellents 513

Toyomichi Shimada
30 Etching Gas 523

Seiji Samukawa
31 Other Industrial Applications 547

Tatsuo Kaiho
viiiCONTENTS
555
557
591
603
605
Index625
Environmental Chemistry of iodine
32 Iodine Bioinorganic Chemistry: Physiology, Structures,

Part VI BIOINORGANIC chemistry and
Radioisotope of iodine
Frithjof C. Küpper and Peter M.H. Kroneck
33 Atmospheric Chemistry of Iodine
34 Radioactive Iodine
Yoshifumi Shirakami
and Mechanisms
Lucy J. Carpenter
Part VII
LIST OF CONTRIBUTORS
Anna Błażewicz Department of Analytical Chemistry, Medical University of

Lublin, Lublin, Poland
Lucy J. Carpenter Wolfson Atmospheric Chemistry Laboratories, University of
York, Heslington, York, UK
James V. Crivello Department of Chemistry and Chemical Biology, Rensselaer
Polytechnic Institute, Troy, New York, NY, USA
Toshifumi Dohi College of Pharmaceutial Sciences, Ritsumeikan University,
Kusatsu, Shiga, Japan
Waldemar Gottardi Department of Hygiene, Microbiology and Social Medicine,
Division of Hygiene and Medical Microbiology, Innsbruck Medical University,
Innsbruck, Austria
Iwao Hachiya Department of Chemistry for Materials, Mie University, Tsu, Mie,
Japan
Junji Inanaga Institute for Molecular Chemistry and Engineering, Kyushu
University, Fukuoka, Japan
Peter Jeschke Bayer CropScience AG, Monheim am Rhein, Germany
Bart Kahr Department of Chemistry and Molecular Design Institute, New York
University, New York, NY, USA
Tatsuo Kaiho Nihon Tennen Gas Co., Ltd., Chiba, Japan
ix
x LIST OF CONTRIBUTORS
Nobuyuki Kaneko Institute for Geo-Resources and Environment, Geological

Survey of Japan, AIST, Tsukuba, Ibaraki, Japan
Hirofumi Kanoh Chiba University, Chiba, Japan
Yasuyuki Kita Emeritus Professor of Osaka University, Ritsumeikan University,
Kusatsu, Shiga, Japan
Tsugio Kitamura Department of Chemistry and Applied Chemistry, Graduate
School of Science and Engineering, Saga University, Saga, Japan
Lars Kloo KTH Royal Institute of Technology, Stockholm, Sweden
Kevin M. Knowles Department of Materials Science and Metallurgy, University of
Cambridge, Cambridge, UK
Takehisa Konishi Chiba University, Chiba, Japan
Werner Krause Bayer Healthcare Pharmaceuticals, Berlin, Germany
Peter M.H. Kroneck Department of Biology, University of Konstanz, Konstanz,
Germany
Stanley T. Krukowski Oklahoma Geological Survey, Mewbourne College of Earth
and Energy, The University of Oklahoma, Norman, OK, USA
Frithjof C. Küpper Oceanlab, University of Aberdeen, Newburgh, UK
Armin Lauterbach SQM, Santiago, Chile
James L. Marshall Department of Chemistry, University of North Texas, Denton,
TX, USA
Virginia R. Marshall Department of Chemistry, University of North Texas, Denton,
TX, USA
Pierangelo Metrangolo Laboratory of Nanostructured Fluorinated Materials
(NFMLab), Department of Chemistry, Materials, and Chemical Engineering
“Giulio Natta”, Politecnico di Milano, Milan, Italy
Giuseppe Resnati Laboratory of Nanostructured Fluorinated Materials (NFMLab),
Department of Chemistry, Materials, and Chemical Engineering “Giulio Natta”,
Politecnico di Milano, Milan, Italy
Steven E. Rokita Department of Chemistry, Johns Hopkins University, Baltimore,
MD, USA
Seiji Samukawa Tohoku University, Sendai, Japan
Mitsuo Sawamoto Department of Polymer Chemistry, Graduate School of
Engineering, Kyoto University, Kyoto, Japan
Toyomichi Shimada Asahi Glass Co., Ltd., Tokyo, Japan
LIST OF CONTRIBUTORS xi
Makoto Shimizu Department of Chemistry for Materials, Mie University, Tsu,

Mie, Japan
Yoshifumi Shirakami Research Centre Nihon Medi-Physics, Co., Ltd., Sodegaura,
Chiba, Japan
Haruhiko Taguchi Tokyo Chemical Industry Co., Ltd., Tokyo, Japan
Giancarlo Terraneo Laboratory of Nanostructured Fluorinated Materials
(NFMLab), Department of Chemistry, Materials, and Chemical Engineering
“Giulio Natta”, Politecnico di Milano, Milan, Italy
Michael B. Zimmermann Laboratory for Human Nutrition, Department of Health
Science and Technology, Swiss Federal Institute of Technology (ETH) Zürich,
Zurich, Switzerland
Preface
A member of the halogen group on the periodic table, iodine is found in seaweeds,
the brine extracted along with natural gas, and Chilean caliche deposits. Iodine is a
micronutrient element that is fundamental to a living body and is essential for the
subsistence and growth of humans and animals. The goiter-preventing effects of
iodine in seaweeds were known to the legendary Chinese emperor Shen-Nung as
early as around 3000 BC, and the knowledge of this treatment was available in
Greece by the time of Hippocrates. Nevertheless, iodine was not isolated and recog-
nized as an element until the early nineteenth century. In 1811, Barnard Courtois of
France found that violet vapor with a strong smell was generated while producing
niter from seaweed ashes, and that when the vapor was cooled down, it turned into
purplish-black flake-like crystalline material having a metallic luster. His friend, who
was entrusted with the research of this unknown material, announced his results on
December 9, 1813. In the following year, 1814, based on the results obtained from
Joseph Louis Gay-Lussac’s research, it was clarified that this material was a chemical
element similar to chlorine. This was the beginning of iodine, named from “iodes” in
Greek. Industrial production began in the same year, and in 1816, iodine was used as
a medical sterilizing agent. Today it is used in many areas. Iodine use is closely
linked to our daily lives. Products include medicated gargle, X-ray contrast media,
and antimicrobial agents. In addition, iodine is useful as an industrial catalyst and has
many applications in the field of agriculture. Recently, iodine has found a wide range
of applications in innovative materials, such as liquid-crystal display (LCD)
polarizing film and electrolytes of dye-sensitized solar panels.
About 90% of iodine in the world is produced in Chile (50–60%) and Japan
(30–40%). In Japan, iodine is positioned as one of the most valuable resources
because Japan is scarce in nonbiological resources. Chiba is the richest prefecture for
xiii
xivPreface
iodine resources in Japan and, thus, the Forum of Iodine Utilization (FIU) was
organized on June 1, 1998, at Chiba University for further development on iodine
utilization in academic and industrial fields under the cooperation of volunteers from
industry, academia, and government. On July 1, 2007, the FIU was progressively
reorganized to the Society of Iodine Science (SIS) based on its successful activities.
In 2011, the Commemorative Symposium of Iodine Science was held at Chiba
University in Japan on the occasion of the bicentennial anniversary of iodine dis-
covery by Bernard Courtois. The special review article entitled “Commemorating
Two Centuries of Iodine Research: An Interdisciplinary Overview of Current
Research” was also issued in the Angewandte Chemie International Edition on
December 2, 2011. Since iodine was officially recognized as a novel element in 1813
by Bernard Courtois and his friends, it is worth publishing a comprehensive book
about iodine in 2013 to celebrate the bicentennial anniversary of this event.
Chiba, Japan Tatsuo Kaiho

December 2013

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Iodine Chemistry

Published by John Wiley & Sons, Inc., Hoboken, New Jersey

Published simultaneously in Canada

Library of Congress Cataloging-in-Publication Data:

Cover Image: Courtesy of Tatsuo Kaiho

Printed in the United States of America

3 Analytical Methods for Iodine and Iodides

7 Hypervalent Iodine 103

8 Iodine and Halogen Bonding 159

Part II Production of iodine 195

9 History of Iodine 197

10 Production Process in the Past 207

11 Iodine Production from Caliche 213

12 Iodine Production from Oilfield Brine 221

13 Iodine Production from Natural Gas Brine 231

14 Recycling of Iodine 243

Part III Synthesis of iodine compounds 249

15 Iodinating Reagents 251

16 Oxidizing Agents 277

17 Reaction of Iodo Compounds 303

18 Metal Iodides–Mediated Reaction 329

Part IV Biological Application of iodine 353

19 Iodinated X-Ray Contrast Agents 355

20 Iodine as Disinfectant 375

21 Synthetic Thyroid Hormone 411

22 Iodine Deficiency Disorders and Their Correction

23 Pharmaceuticals: Therapeutic Agents 433

24 Agrochemicals and Anthelmintics 439

Part V Industrial Application of iodine 457

25 Diaryliodonium Salt Photoacid Generators 459

26 Polarizing Films 479

27 Iodine in Polymer Synthesis: An Important Element

28 Iodine in Dye-Sensitized Solar Cells 501

29 Fluorinated Repellents 513

30 Etching Gas 523

31 Other Industrial Applications 547

32 Iodine Bioinorganic Chemistry: Physiology, Structures,

33 Atmospheric Chemistry of Iodine

Anna Błażewicz Department of Analytical Chemistry, Medical University of

Nobuyuki Kaneko Institute for Geo-Resources and Environment, Geological

Makoto Shimizu Department of Chemistry for Materials, Mie University, Tsu,

Chiba, Japan Tatsuo Kaiho

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3 Analytical Methods for Iodine and Iodides

7 Hypervalent Iodine 103

8 Iodine and Halogen Bonding 159

Part II Production of iodine 195

9 History of Iodine 197

10 Production Process in the Past 207

11 Iodine Production from Caliche 213

12 Iodine Production from Oilfield Brine 221

13 Iodine Production from Natural Gas Brine 231

14 Recycling of Iodine 243

Part III Synthesis of iodine compounds 249

15 Iodinating Reagents 251

16 Oxidizing Agents 277

17 Reaction of Iodo Compounds 303

18 Metal Iodides–Mediated Reaction 329

Part IV Biological Application of iodine 353

19 Iodinated X-Ray Contrast Agents 355

20 Iodine as Disinfectant 375

21 Synthetic Thyroid Hormone 411

23 Pharmaceuticals: Therapeutic Agents 433

24 Agrochemicals and Anthelmintics 439

Part V Industrial Application of iodine 457

25 Diaryliodonium Salt Photoacid Generators 459

26 Polarizing Films 479

28 Iodine in Dye-Sensitized Solar Cells 501

29 Fluorinated Repellents 513

30 Etching Gas 523

31 Other Industrial Applications 547

33 Atmospheric Chemistry of Iodine

Chiba, Japan Tatsuo Kaiho