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Acetylene and Its Polymers 150+ Years of History Springerbriefs in Molecular Science SPRINGER BRIEFS IN MOLECULAR SCIENCE HISTORY OF CHEMISTRY Seth C. Rasmussen Acetylene and Its Polymers 150+ Years of History SpringerBriefs in Molecular Science History of Chemistry Series editor Seth C. Rasmussen, Department of Chemistry and Biochemistry, North Dakota State University, Fargo, ND, USA More information about this series at http://www.springer.com/series/10127 Seth C. Rasmussen Acetylene and Its Polymers 150+ Years of History 123 Seth C. Rasmussen Department of Chemistry and Biochemistry North Dakota State University Fargo, ND, USA ISSN 2191-5407 ISSN 2191-5415 (electronic) SpringerBriefs in Molecular Science ISSN 2212-991X SpringerBriefs in History of Chemistry ISBN 978-3-319-95488-2 ISBN 978-3-319-95489-9 (eBook) https://doi.org/10.1007/978-3-319-95489-9 Library of Congress Control Number: 2018947476 © The Author(s) 2018 This work is subject to copyright. All rights are reserved by the Publisher, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. The publisher, the authors and the editors are safe to assume that the advice and information in this book are believed to be true and accurate at the date of publication. Neither the publisher nor the authors or the editors give a warranty, express or implied, with respect to the material contained herein or for any errors or omissions that may have been made. The publisher remains neutral with regard to jurisdictional claims in published maps and institutional affiliations. This Springer imprint is published by the registered company Springer International Publishing AG part of Springer Nature The registered company address is: Gewerbestrasse 11, 6330 Cham, Switzerland Acknowledgements I would first and foremost like to thank the Department of Chemistry and Biochemistry at North Dakota State University (NDSU) for supporting my con- tinuing efforts in the history of chemistry. In addition, I need to acknowledge the American Chemical Society’s Division of the History of Chemistry (HIST) in providing the environment and encouragement which allowed the development of my initial historical interests into my current active research and contributions in the history of science. I also must acknowledge the Australian-American Fulbright Commission who supported my stay at the University of Newcastle as a Fulbright senior scholar for the spring of 2018, during which large sections of the current volume were written. The strength of this particular volume was due to the contributions of a number of friends and colleagues. As such, I would like to thank Prof. Alan Rocke (Case Western Reserve University) for helpful discussions on the issues of correctly determining molecular formulas of organic species during the nineteenth century, Dr. Vera V. Mainz (University of Illinois) and Elsa B. Atson (Science History Institute) for assistance with tracking down sources on Paul and Arnould Thenard, Dr. Reggie Hudson (NASA Astrochemistry Laboratory) for helpful discussions and feedback on cuprene, as well as for providing the color image of a cuprene film, Prof. Yasu Furukawa (Nihon University) for assistance in finding biographical information on Hatano and Ikeda, and Prof. Dennis Cooley (NDSU) for help with philosophy sources relating to the nature of discovery. Most critically, I would like to thank Prof. John Reynolds (Georgia Tech) for initially bringing the work of Smith and Berets to my attention, which initiated much of my detailed re-evaluation of the history of polyacetylene and Dr. Choon Do for his help in locating Dr. Hyung Chick Pyun and his assistance in collecting much of his biographical material. In addition, I need to acknowledge the Interlibrary Loan Department of NDSU, who went out of their way to track down many elusive and somewhat obscure sources, as well as my brother, Dr. Kent A. Rasmussen, for continued assistance with translations. I could not imagine doing historical work without both of these critical resources. I also need to thank the following current and former members of v vi Acknowledgements my materials research group for reading various drafts of this manuscript and providing critical feedback: Prof. Christopher L. Heth (Minot State University), Kristine L. Konkol, Even W. Culver, Dr. Eric J. Uzelac (Marvin Windows), and Trent E. Anderson. Finally, and perhaps most importantly, I must express my continued thanks to Elizabeth Hawkins at Springer, without whom this growing series of historical volumes would not have become a reality, as well as Sofia Costa who now oversees the series as its managing editor at Springer. Contents 1 Introduction ........................................... 1 1.1 Saturated Gaseous Hydrocarbons ........................ 5 1.2 Unsaturated Gaseous Hydrocarbons ...................... 9 1.3 Polymerization of Unsaturated Gaseous Hydrocarbons ........ 12 1.4 Scope of the Current Volume .......................... 15 References ............................................. 16 2 Acetylene ............................................. 21 2.1 Edmund Davy and Bicarburet of Hydrogen ................ 21 2.2 Marcelin Berthelot and Acetylene ....................... 24 2.3 Thomas Willson and Acetylene from Calcium Carbide ........ 30 References ............................................. 35 3 Cuprene .............................................. 37 3.1 Berthelot and the Initial Polymerization of Acetylene ......... 37 3.2 Paul and Arnould Thenard and the Effect of Electric Discharge on Acetylene .............................. 39 3.3 Additional Discharge Studies of Acetylene ................. 42 3.4 Erdmann and Polymerization Over Copper ................. 45 3.5 Sabatier and Cuprene ................................ 46 3.6 Alexander and More Studies of Acetylene Over Copper ....... 48 3.7 Gooch and Further Studies Over Copper Oxide ............. 49 3.8 Lozanić and a Return to Electric Discharge ................ 51 3.9 Daniel Berthelot and UV Polymerization .................. 53 3.10 Kaufmann and Discharge Versus Thermal Polymerization ...... 54 3.11 Mund and Polymerization via Alpha Particles .............. 56 3.12 Lind and the Polymerization of Acetylene Under Various Conditions ........................................ 58 3.13 What Exactly Is Cuprene? ............................. 60 References ............................................. 62 vii viii Contents 4 Polyenes and Polyvinylenes ................................ 67 4.1 Polyenes ......................................... 67 4.1.1 Richard Kuhn and the Study of Conjugated Double Bonds ................................ 68 4.1.2 Blout and the Spectroscopy of Polyenes ............. 72 4.1.3 Bohlmann and Higher Dimethylpolyenes ............. 73 4.1.4 Unfunctionalized Polyenes ....................... 75 4.2 Polyvinylenes ...................................... 78 4.2.1 Polyvinylenes from Poly(vinyl chloride) ............. 78 4.2.2 Polyvinylenes from Poly(vinyl alcohol) .............. 80 References ............................................. 81 5 Polyacetylene .......................................... 85 5.1 Natta and the Polymerization of Acetylenes ................ 85 5.2 Additional Studies of Acetylene Polymerizations ............ 90 5.3 Masahiro Hatano ................................... 92 5.4 Sakuji Ikeda ....................................... 96 5.5 Hideki Shirakawa and Polyacetylene Films ................ 99 References ............................................. 106 6 Doped Polyacetylene ..................................... 109 6.1 Berets and Smith ................................... 109 6.2 MacDiarmid, Heeger, and (SN)X ........................ 112 6.3 Development of Doped Polyacetylene Films................ 115 6.4 Continued Study of Doped Polyacetylene Films ............. 117 6.5 Naarmann and Efforts to Maximize Conductivity ............ 118 References ............................................. 120 7 2000 Nobel Prize in Chemistry ............................. 125 7.1 Details of the 2000 Nobel Prize in Chemistry ............... 126 7.2 What Is Discovery? ................................. 127 7.3 Legacy ........................................... 130 References ............................................. 130 Index ...................................................... 133 About the Author Seth C. Rasmussen is a professor of Chemistry at North Dakota State University (NDSU), Fargo ([email protected]). A native of the Seattle area, he received his B.S. in Chemistry from Washington State University in 1990, before continuing his graduate studies at Clemson University under the guidance of Prof. John D. Petersen. After completing his Ph.D. in Inorganic Chemistry in 1994, he moved to the University of Oregon to study conjugated organic polymers as a postdoctoral associate under Prof. James E. Hutchison. He then accepted a teaching position at the University of Oregon in 1997, before moving to join the faculty at NDSU in 1999. Attaining the rank of full professor in 2012,
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