Green Solvents, Volume 4 E-Book

• Herausgeber: Wiley-VCH
• Kategorie: Wissenschaft und neue Technologien
• Serie: Handbook of Green Chemistry
• Sprache: Englisch

Seitenzahl: 1007

Veröffentlichungsjahr: 2014

Beschreibung

The shift towards being as environmentally-friendly as possible has resulted in the need for this important volume on the topic of supercritical solvents. Edited by the leading experts in the field, Professors Walter Leitner and Phil Jessop, this is an essential resource for anyone wishing to gain an understanding of the world of green chemistry, as well as for chemists, environmental agencies and chemical engineers.

Leseprobe

CONTENTS

Cover

Related Titles

Title Page

Copyright

Foreword

Preface

About the Editors

List of Contributors

Chapter 1: Introduction

1.1 What is a Supercritical Fluid (SCF)?

1.2 Practical Aspects of Reactions in Supercritical Fluids

1.3 The Motivation for Use of SCFs in Modern Chemical Synthesis

1.4 The History and Applications of SCFs

References

Chapter 2: High-pressure Methods and Equipment

2.1 Introduction

2.2 Infrastructure for High-pressure Experiments

2.3 High-pressure Reactors

2.4 Auxiliary Equipment and Handling

2.5 Dosage Under a High-pressure Regime

2.6 Further Regulations and Control in Flow Systems

2.7 Evaporation and Condensation

2.8 Complete Reactor Systems for Synthesis with SCFs

2.9 Conclusion

References

Chapter 3: Basic Physical Properties, Phase Behavior and Solubility

3.1 Introduction

3.2 Basic Physical Properties of Supercritical Fluids

3.3 Phase Behavior in High-Pressure Systems

3.4 Factors Affecting Solubility in Supercritical Fluids

References

Chapter 4: Expanded Liquid Phases in Catalysis: Gas-expanded Liquids and Liquid–Supercritical Fluid Biphasic Systems

4.1 A Practical Classification of Biphasic Systems Consisting of Liquids and Compressed Gases for Multiphase Catalysis

4.2 Physical Properties of Expanded Liquid Phases

4.3 Chemisorption of Gases in Liquids and their Use for Synthesis and Catalysis

4.4 Using Gas-expanded Liquids for Catalysis

4.5 Why Perform Liquid–SCF Biphasic Reactions?

4.6 Biphasic Liquid–SCF Systems

4.7 Biphasic Reactions in Emulsions

References

Chapter 5: Synthetic Organic Chemistry in Supercritical Fluids

5.1 Introduction

5.2 Hydrogenation in Supercritical Fluids

5.3 Hydroformylation and Related Reactions in Supercritical Fluids

5.4 Oxidation Reactions in Supercritical Fluids

5.5 Palladium-mediated Coupling Reactions in Supercritical Fluids

5.6 Miscellaneous Catalytic Reactions in Supercritical Fluids

5.7 Cycloaddition Reactions in Supercritical Fluids

5.8 Photochemical Reactions in Supercritical Fluids

5.9 Radical Reactions in Supercritical Fluids

5.10 Biotransformations in Supercritical Fluids

5.11 Conclusion

References

Chapter 6: Heterogeneous Catalysis

6.1 Introduction and Scope

6.2 General Aspects of Heterogeneous Catalysis in SCFs and GXLs

6.3 Selected Examples of Heterogeneously Catalyzed Conversions in SCFs and GXLs

6.4 Outlook

References

Chapter 7: Enzymatic Catalysis

7.1 Enzymes in Non-aqueous Environments

7.2 Supercritical Fluids for Enzyme Catalysis

7.3 Enzymatic Reactions in Supercritical Fluids

7.4 Reaction Parameters in Supercritical Biocatalysis

7.5 Stabilized Enzymes for Supercritical Biocatalysis

7.6 Enzymatic Catalysis in IL–scCO2 Biphasic Systems

7.7 Future Trends

References

Chapter 8: Polymerization in Supercritical Carbon Dioxide

8.1 General Aspects

8.2 Polymerization in scCO2

8.3 Conclusion

References

Chapter 9: Synthesis of Nanomaterials

9.1 Introduction

9.2 Metal and Semiconductor Nanocrystals

9.3 Metal Oxide Nanoparticles

9.4 Carbon Nanomaterials

9.5 Nanocomposites

9.6 Conclusion

References

Chapter 10: Photochemical and Photo-induced Reactions in Supercritical Fluid Solvents

10.1 Introduction

10.2 Photochemical Reactions in Supercritical Fluid Solvents

10.3 Photo-initiated Radical Chain Reactions in Supercritical Fluid Solvents

10.4 Conclusion

References

Chapter 11: Electrochemical Reactions

11.1 Introduction

11.2 Electrochemical Methods

11.3 Analytes

11.4 Electrolytes

11.5 Electrochemical Cell and Supercritical Fluid Delivery System

11.6 Electrodes

11.7 Solvents

11.8 Applications

11.9 Conclusion and Outlook

References

Chapter 12: Coupling Reactions and Separation in Tunable Fluids: Phase Transfer-Catalysis and Acid-catalyzed Reactions

12.1 Introduction

12.2 Phase Transfer Catalysis

12.3 Near-critical Water

12.4 Alkylcarbonic Acids

12.5 Conclusion

References

Chapter 13: Chemistry in Near- and Supercritical Water

13.1 Introduction

13.2 Properties

13.3 Synthesis Reactions [1, 3–5]

13.4 Biomass Conversion

13.5 Supercritical Water Oxidation (SCWO)

13.6 Inorganic Compounds in NSCW

13.7 Conclusion

13.8 Future Trends

References

Index

End User License Agreement

List of Tables

Table 1.1

Table 1.2

Table 2.1

Table 2.2

Table 2.3

Table 2.4

Table 2.5

Table 2.6

Table 2.7

Table 2.8

Table 2.9

Table 3.1

Table 3.2

Table 3.3

Table 3.4

Table 3.5

Table 3.6

Table 4.1

Table 4.2

Table 4.3

Table 4.4

Table 4.5

Table 4.6

Table 4.7

Table 4.8

Table 5.1

Table 6.1

Table 6.2

Table 7.1

Table 7.2

Table 8.1

Table 8.2

Table 8.3

Table 11.1

Table 11.2

Table 12.1

Table 12.2

Table 12.3

List of Illustrations

Figure 1

Figure 1.1

Figure 1.2

Figure 1.3

Figure 1.4

Figure 1.5

Figure 1.6

Figure 1.7

Scheme 1.1

Figure 1.8

Figure 2.1

Figure 2.2

Figure 2.3

Figure 2.4

Figure 2.5

Figure 2.6

Figure 2.7

Figure 2.8

Figure 2.9

Figure 2.10

Figure 2.11

Figure 2.12

Figure 3.1

Figure 3.2

Figure 3.3

Figure 3.4

Figure 3.5

Figure 3.6

Figure 3.7

Figure 3.8

Figure 3.9

Figure 3.10

Figure 3.11

Figure 3.12

Figure 3.13

Figure 3.14

Figure 3.15

Figure 3.16

Figure 3.17

Figure 4.1

Figure 4.2

Figure 4.3

Figure 4.4

Figure 4.5

Figure 4.6

Figure 4.7

Figure 4.8

Figure 4.9

Figure 4.10

Figure 4.11

Figure 4.12

Figure 4.13

Figure 4.14

Figure 4.15

Figure 4.16

Figure 4.17

Figure 4.18

Scheme 4.1

Scheme 4.2

Scheme 4.3

Scheme 4.4

Figure 4.19

Figure 4.20

Figure 4.21

Figure 4.22

Figure 4.23

Figure 4.24

Figure 4.25

Figure 4.26

Figure 4.27

Scheme 4.5

Scheme 4.6

Figure 4.28

Scheme 4.7

Scheme 4.8

Figure 4.29

Figure 4.30

Figure 4.31

Scheme 4.9

Figure 4.32

Scheme 4.10

Scheme 4.11

Figure 4.33

Scheme 4.12

Scheme 4.13

Figure 4.34

Figure 4.35

Figure 4.36

Figure 4.37

Figure 4.38

Scheme 4.14

Figure 4.39

Figure 4.40

Scheme 4.15

Figure 4.41

Figure 4.42

Figure 4.43

Figure 4.44

Figure 4.45

Figure 4.46

Scheme 4.16

Figure 4.47

Figure 4.48

Scheme 4.17

Scheme 4.18

Scheme 4.19

Scheme 4.20

Figure 4.49

Figure 4.50

Figure 4.51

Scheme 4.21

Scheme 4.22

Scheme 5.1

Scheme 5.2

Scheme 5.3

Scheme 5.4

Scheme 5.5

Scheme 5.6

Scheme 5.7

Scheme 5.8

Scheme 5.9

Scheme 5.10

Scheme 5.11

Scheme 5.12

Scheme 5.13

Scheme 5.14

Scheme 5.15

Scheme 5.16

Scheme 5.17

Scheme 5.18

Scheme 5.19

Scheme 5.20

Scheme 5.21

Scheme 5.22

Scheme 5.23

Scheme 5.24

Scheme 5.25

Scheme 5.26

Scheme 5.27

Scheme 5.28

Scheme 5.29

Scheme 5.30

Scheme 5.31

Scheme 5.32

Scheme 5.33

Scheme 5.34

Scheme 5.35

Scheme 5.36

Scheme 5.37

Scheme 5.38

Scheme 5.39

Scheme 5.40

Scheme 5.41

Scheme 5.42

Scheme 5.43

Scheme 5.44

Scheme 5.45

Scheme 5.46

Scheme 5.47

Scheme 5.48

Scheme 5.49

Figure 5.1

Scheme 5.50

Scheme 5.51

Scheme 5.52

Scheme 5.53

Scheme 5.54

Scheme 5.55

Scheme 5.56

Scheme 5.57

Scheme 5.58

Scheme 5.59

Scheme 5.60

Scheme 5.61

Scheme 5.62

Scheme 5.63

Scheme 5.64

Scheme 5.65

Scheme 5.66

Scheme 5.67

Scheme 5.68

Scheme 5.69

Scheme 5.70

Scheme 5.71

Scheme 5.72

Scheme 5.73

Scheme 5.74

Scheme 5.75

Scheme 5.76

Scheme 5.77

Scheme 5.78

Scheme 5.79

Scheme 5.80

Scheme 5.81

Scheme 5.82

Scheme 5.83

Scheme 5.84

Scheme 5.85

Scheme 5.86

Figure 6.1

Figure 6.2

Figure 6.3

Figure 6.4

Figure 6.5

Figure 6.6

Figure 6.7

Figure 6.8

Figure 6.9

Figure 6.10

Figure 6.11

Figure 6.12

Figure 6.13

Figure 6.14

Scheme 7.1

Figure 7.1

Scheme 7.2

Figure 7.2

Figure 7.3

Scheme 7.3

Scheme 7.4

Figure 7.4

Figure 7.5

Figure 7.6

Figure 8.1

Figure 8.2

Figure 8.3

Figure 8.4

Scheme 8.1

Scheme 8.2

Scheme 8.3

Figure 8.5

Figure 8.6

Scheme 8.4

Scheme 8.5

Scheme 8.6

Scheme 8.7

Scheme 8.8

Scheme 8.9

Scheme 8.10

Figure 9.1

Figure 9.2

Figure 9.3

Figure 9.4

Figure 9.5

Figure 10.1

Figure 10.2

Figure 10.3

Figure 10.4

Scheme 10.1

Scheme 10.2

Scheme 10.3

Scheme 10.4

Figure 10.5

Scheme 10.5

Scheme 10.6

Scheme 10.7

Scheme 10.8

Scheme 10.9

Figure 10.6

Figure 10.7

Figure 12.1

Figure 12.2

Figure 12.3

Figure 12.4

Figure 12.5

Figure 12.6

Figure 12.7

Figure 12.8

Figure 12.9

Scheme 12.1

Figure 12.10

Figure 12.11

Figure 12.12

Figure 12.13

Figure 12.14

Figure 12.15

Figure 12.16

Scheme 12.2

Scheme 12.3

Figure 12.17

Figure 12.18

Figure 12.19

Figure 12.20

Scheme 12.4

Figure 12.21

Figure 13.1

Figure 13.2

Scheme 13.1

Scheme 13.2

Scheme 13.3

Figure 13.3

Scheme 13.4

Scheme 13.5

Scheme 13.6

Scheme 13.7

Scheme 13.8

Scheme 13.9

Scheme 13.10

Scheme 13.11

Scheme 13.12

Scheme 13.13

Figure 13.4

Guide

Cover

Table of Contents

Preface

Chapter 1

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Handbook of Green Chemistry

Volume 4Supercritical Solvents

Volume Edited by Walter Leitner and Philip G. Jessop

All books published by Wiley-VCH are carefully produced. Nevertheless, authors, editors, and publisher do not warrant the information contained in these books, including this book, to be free of errors. Readers are advised to keep in mind that statements, data, illustrations, procedural details or other items may inadvertently be inaccurate.

Library of Congress Card No.:

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A catalogue record for this book is available from the British Library.

Bibliographic information published by the Deutsche Nationalbibliothek

The Deutsche Nationalbibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data are available on the Internet at http://dnb.d-nb.de.

© 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

All rights reserved (including those of translation into other languages). No part of this book may be reproduced in any form – by photoprinting, microfilm, or any other means – nor transmitted or translated into a machine language without written permission from the publishers. Registered names, trademarks, etc. used in this book, even when not specifically marked as such, are not to be considered unprotected by law.

ISBN: 978-3-527-32590-0

Foreword

For several centuries, Chemistry has strongly contributed to a fast and almost unlimited trend of progress and innovation that have deeply modified and improved human life in all its aspects. But, presently, chemistry is also raising fears about its immediate and long-term impact on environment, leading to a growing demand for development of “green chemistry” preserving environment and natural non-renewable resources. Changing raw materials to renewable sources, using low energy-consumption processes, reprocessing all effluents and inventing new environment-friendly routes for the manufacture of more efficacious products are immense challenges that will condition the future of mankind.

In this context of sustainable development, Supercritical Fluids (SCF) and Gas-Expanded Liquids (GXL) are of rapidly-growing interest because either they are non-toxic and non-polluting solvents (like carbon dioxide or water) or they help one to avoid harmful intermediates through new processing routes. After two decades of development of new extraction/fractionation/purification processes using SCFs - mainly CO2 - with about 250 industrial-scale plants now in operation around the world, other applications have been and will be at the centre of new developments for the present decade and the coming one:

Manufacture of high-performance materials including pharmaceutical formulations, bio-medical devices and many specific polymeric, inorganic or composite materials, either by physical processes or chemical synthesis;

New routes of chemical or biochemical synthesis, coupled with product purification;

Innovative waste management and recycle.

It has to be understood that moving to SCF or GXL media for chemical synthesis shall not be considered as a “simple” substitution of “classical” organic solvents, but imposes a complete “reset” of knowledge of synthesis routes, reaction schemes and parameters. One main difference is related to the physico-chemical properties of these fluids that are both “tunable” solvents and separation agents. Some are also reactants at the same time. Because of these properties, reaction rate and selectivity are very different from those observed in liquid media, as well exemplified by hydrogenation reactions over heterogeneous catalysts. Moreover, many new environmentally-friendly processes using CO2 and water lead to innovative high-tech materials (especially nano-structured materials), biomass conversion and waste treatment such as, for example, PET-residues recycling by hydrothermal depolymerisation.

This is why this new edition, deeply revised and dealing with new areas, arrives at an optimal moment when scientists and engineers are facing the new challenges of sustainable development and demand for higher-performance products. In the fast-changing world of science, this update is a necessary tool offered to help the scientific community appreciate the opportunities presented by these fluids and to prepare chemists and engineers to incorporate these techniques in their process “tool-box”.

March 2009

Michel Perrut

Preface

Reactions under supercritical conditions have been used for industrial production on various scales for most of the 20th century, but the current intense academic interest in the science and applications of supercritical fluids (SCFs) dates from the mid 1980's (Figure 1) and the application of SCFs in the chemical synthesis of organic molecules or materials became a “hot topic” starting in the early 1990's. Processes involving SCFs can be conducted in a fully homogeneous monophasic fluid or in biphasic systems. Biphasic conditions can involve a supercritical or subcritical gas as the upper phase and a gas-expanded liquid (GXL) below. The optimum situation is often a delicate balance of thermodynamic and kinetic boundaries for a given transformation. This book is intended to introduce the reader to the wide range of opportunities provided by the various synthetic methodologies developed so far for synthesis in SCFs and GXLs.

Figure 1 Publications on the topic of supercritical fluids per year (data mined from the Chemical Abstracts Service).

Applications of SCFs include their use as solvents for extractions, as eluents for chromatography, and as media for chemical reactions. All of these are worthy topics for extensive scientific and technical discussion, and in fact have been topics of books in the past. We decided that a satisfactory coverage of all three topics would not be possible in a single monograph of a reasonable size, and therefore we chose to cover only one. While extractions such as decaffeination of coffee and chromatography such as the supercritical CO2-based preparative chromatography used in the pharmaceutical industry are great examples of the environmental and economic benefits of SCFs, we focus here on chemical synthesis where the fluid is not only used as a mass separation agent, but also directly affects the molecular transformation.

Supercritical fluids and gas-expanded liquids may be alternatives to liquid solvents, but they are neither simple nor simply replacements of solvents. The experimental chemist could not modify a written synthetic method by simply crossing out the word “benzene” and replacing it with the words “supercritical carbon dioxide”. Many other modifications to the procedure would be necessary, not only because of the need for pressurized equipment but also because of the inferior solvent strength of many SCFs. On the other hand, additional degrees of freedom in the reaction parameters emerge from the high compressibility of SCFs, allowing density to be introduced as an important variable. At the same time, mass transfer can be greatly enhanced in the presence of SCFs. Selective separation and compartmentalization of elementary processes in multiphase systems offer another parameter that can be exploited especially in catalytic processes. These are only some of the reasons why the result of a chemical synthesis can sometimes be dramatically changed, often for the better, by this solvent switch. If such beneficial effects can be combined with the benign nature of many SCFs such as CO2 or H2O, they can contribute to the development of more sustainable chemical processes, explaining why SCFs and GXLs are often referred to as “Green Solvents”.

It is only fair to say that we are still far away from a detailed understanding of all the effects of using SCFs and GXLs. More basic research will be needed before we learn how to exploit the benefits in the most efficient way. In the meantime, it is our hope that the chemist or engineer considering using one of these fluids as a medium for a reaction will turn to this volume to find out both what has been done, how to do it, and, more importantly, what new and innovative directions are yet to be taken.

At this point, we must offer a safety warning and disclaimer. Supercritical fluids are used at high pressures and in some cases at elevated temperatures. The chemist contemplating their use must become acquainted with the safety precautions appropriate for experiments with high pressures and temperatures. Some SCFs also have reactive hazards. The safety considerations mentioned in Chapters 1 and 2 are meant neither to be comprehensive nor to substitute for a proper investigation by every researcher of the risks and appropriate precautions for a contemplated experiment.

We have selected the chapter topics to guide the reader through the process of planning and carrying out chemical syntheses in SCFs and GXLs. The subjects include a brief overview of the historical development and current use, as well as a description of equipment, methods, and phase behaviour considerations. The properties of biphasic conditions and gas-expanded liquids are spelled out in chapter 4, and all these themes are elaborated upon in the largest part of the book which is devoted to various types of chemical reactions involving SCFs and GXLs as solvents and/or reactants. The emphasis is on synthetic reactions, rather than reactions tested for the purpose of investigating near-critical phenomena.

This book represents a partial update of our 1999 book on “Chemical Synthesis Using Supercritical Fluids”, but most of the chapters are entirely new and the selection of topics is not the same. We therefore encourage readers, if they want more information, to look up the 1999 book.

The contributors to the present volume, all leading experts in the field, have given us a wide view of the types and methods of chemistry being performed in supercritical fluids and expanded liquids. Many of the techniques that the reader will find described in these pages have been laboriously developed by these contributors and their colleagues. We gratefully thank all of the contributors for agreeing to take time out from their research schedules to write chapters for this volume.

We also thank the following people and institutions for providing us with information or photographic material on the historical aspects and the industrial use of SCFs: Dr. J. Abeln (Forschungszentrum Karlsruhe), Dr. U. Budde (Schering AG), Dr. H.-E. Gasche (Bayer AG), Dr. P. Møller (Poul Møller Consultancy), Dr. T. Muto (Idemitsu Petrochemical), Prof. G. Ourisson and the Académie des Sciences, Dr. A. Rehren (Degussa AG), M.-C. Thooris (Ecole Polytechnique Palasieau) and representatives of Eco Waste Technology and General Atomics.

Special thanks are due to Dr. Markus Höslcher at ITMC, RWTH Aachen, and Drs. Elke Maase and Lesley Belfit at Wiley-VCH for their competent help and collaboration in producing this book. Furthermore, we wish to express our sincere thanks to all the members of our research groups, for their talents and their enthusiasm, which make our research efforts devoted to SCFs and GXLs so much fun.

Finally, and most importantly, we dedicate our own contribution to this book to our wives and families, for all their love and understanding throughout the years and especially during the preparation of this volume.

February 2009

Philip Jessop and Walter Leitner

About the Editors

Series Editor

Paul T. Anastas joined Yale University as Professor and serves as the Director of the Center for Green Chemistry and Green Engineering there. From 2004–2006, Paul was the Director of the Green Chemistry Institute in Washington, D.C. Until June 2004 he served as Assistant Director for Environment at the White House Office of Science and Technology Policy where his responsibilities included a wide range of environmental science issues including furthering international public-private cooperation in areas of Science for Sustainability such as Green Chemistry. In 1991, he established the industry-government-university partnership Green Chemistry Program, which was expanded to include basic research, and the Presidential Green Chemistry Challenge Awards. He has published and edited several books in the field of Green Chemistry and developed the 12 Principles of Green Chemistry.

Volume Editors

Philip Jessop is the Canada Research Chair of Green Chemistry at Queen's University in Kingston, Ontario, Canada. After his Ph.D. (Inorganic Chemistry, UBC, 1991) and a postdoctoral appointment at the University of Toronto, he took a contract research position in the Research Development Corp. of Japan under the supervision of Ryoji Noyori, investigating reactions in supercritical CO2. As a professor at the University of California-Davis (1996–2003) and then at Queen's University, he has studied green solvents, the conversion of waste CO2 to useful products, and aspects of H2 chemistry. He has presented popular chemistry shows to thousands of members of the public. Distinctions include the Canadian Catalysis Lectureship Award (2004), a Canada Research Chair (2003 to present), and the NSERC Polanyi Award (2008). He has chaired the 2007 CHEMRAWN and ICCDU Conference on Greenhouse Gases, will chair the 2010 3rd International IUPAC Conference on Green Chemistry, and serves as Technical Director of GreenCentre Canada.

Walter Leitner was born in 1963. He obtained his Ph.D. with Prof. Henri Brunner at Regensburg University in 1989 and was a Postdoctoral Fellow with Prof. John M. Brown at the University of Oxford. After research within the Max-Planck-Society under the mentorship of Profs. Eckhard Dinjus (Jena) and Manfred T. Reetz (Mülheim), he was appointed Chair of Technical Chemistry and Petrochemistry at RWTH Aachen University in 2002 as successor to Prof. Willi Keim. Walter Leitner is External Scientific Member of the Max-Planck-Institut für Kohlenforschung and Scientific Director of CAT, the joint Catalysis Research Center of RWTH Aachen and the Bayer Company.

His research interests are the molecular and reaction engineering principles of catalysis as a fundamental science and key technology for Green Chemistry. In particular, this includes the development and synthetic application of organometallic catalysts and the use of alternative reaction media, especially supercritical carbon dioxide, in multiphase catalysis. Walter Leitner has published more than 170 publications in this field and co-edited among others the first edition of “Synthesis using Supercritical Fluids” and the handbook on “Multiphase Homogeneous Catalysis”. Since 2004, he serves as the Scientific Editor of the Journal “Green Chemistry” published by the Royal Society of Chemistry. The research of his team has been recognized with several awards including the Gerhard-Hess-Award of the German Science Foundation (1997), the Otto-Roelen-Medal of Dechema (2001), and the Wöhler-Award of the German Chemical Society (2009).

List of Contributors

Douglas C. Barnes

University of Leeds

School of Chemistry

Leeds LS2 9JT

UK

Uwe Beginn

University of Osnabrück

Institute for Chemistry

Organic Materials Chemistry

Barbarastrasse 7

49076 Osnabrück

Germany

Teresa De Diego

Universidad de Murcia

Facultad de Química

Departamento de Bioquímica y Biología Molecular “B” e Inmunología