Beruflich Dokumente
Kultur Dokumente
materials processing
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Springer Series in
materials processing
Series Editors: H. Warlimont E. Weber W. Michaeli
This series is focused on the science and application of materials processing as an essential
part of progress in the materials f ield. It addresses researchers and process engineers alike.
The scope of the series includes all classes of materials metals, inorganic non-metallic
materials, polymers and composites in the form of bulk materials, thin f ilms and layered
structures as well as micro- and nanostructured forms. All aspects of materials processing
from fundamental understanding to innovative strategies and methods of practical process
implementation and control are covered. It is the aim of the series to provide comprehensive
information on the science and application of leading-edge and well-established processing
technologies.
Supercritical Fluids
Molecular Interactions, Physical Properties,
and New Applications
13
Professor Yasuhiko Arai
Kyushu University, Graduate School of Engineering
Hakozaki 6-10-1, Higashi-ku, 812-0053 Fukuoka, Japan
arai@chem-eng.kyushu-u.ac.jp
Professor Takeshi Sako
Shizuoka University, Faculty of Engineering
Johoku 3-5-1, Hamamatsu-shi, 432-8561 Shizuoka, Japan
ttsako@ipc.shizuoka.ac.jp
Dr. Yoshihiro Takebayashi
National Institute of Advanced Industrial Science and Technology
Higashi 1-1, Tsukuba-shi, 305-8565 Ibaraki, Japan
chikulin@ni.aist.go.jp
Series Editors:
Professor Dr. H. Warlimont
f Festkorper-
Institut fur und Werkstofforschung e.V.,
Helmholtzstrasse 20, 01069 Dresden, Germany
This work is subject to copyright. All rights are reserved, whether the whole or part of the material is
concerned, specif ically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting,
reproduction on microf ilm or in any other way, and storage in data banks. Duplication of this publication or
parts thereof is permitted only under the provisions of the German Copyright Law of September 9, 1965, in its
current version, and permission for use must always be obtained from Springer-Verlag. Violations are liable
for prosecution under the German Copyright Law.
http://www.springer.de
Springer-Verlag Berlin Heidelberg 2002
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The use of general descriptive names, registered names, trademarks, etc. in this publication does not imply,
even in the absence of a specif ic statement, that such names are exempt from the relevant protective laws and
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Typesetting by the editors
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Scientists have been aware of the novel characteristics of a dense gas or su-
percritical fluid as a solvent for more than a century. More recently, super-
critical fluids or substances in a dense gas state have been recognized to have
many favorable characteristics for use in the chemical industry. Research into
supercritical fluid science and technology has lead to the development of in-
dustrial processes, including coffee and tea decaffeination, hops and flavor
extraction, and pharmaceutical separations. During the past decade, there has
been renewed interest in supercritical fluids especially for water, carbon diox-
ide, and alcohols, since these solvents can be expected to provide new tech-
nologies for green or sustainable chemistries.
The physical properties of supercritical fluids and their mixtures continue
to be of importance in these developments and there is increased activity re-
garding reactions in supercritical fluids. In Japan, one of the earliest reports on
anomalous behavior of reactions at supercritical conditions was by Toriumi and
Hara (1941), who noted a pronounced increase in the oxidation of ammonia and
sulfur dioxide in the critical region. Since then, there have been many devel-
opments in fractionation, drying, materials processing, chemical recycling, and
waste treatment. Since 1992, the fundamentals and applications of supercritical
fluids have been studied as a priority research area, supported by the Japanese
government and also through various other research initiatives. This book
summarizes some of the latest research into supercritical fluid science and
technology in terminology that is suitable for industrialists, scientists, and en-
gineers.
Supercritical fluids can lead to promising technologies in many fields
such as separation, chemical reaction, material processing, waste treatment,
plastic recycling and others. They can provide environmentally friendly and
advanced industrial processes with less energy consumption and high effi-
ciency. Supercritical carbon dioxide, water and alcohol are excellent candidates
for industrial use because of their unique and suitable solvent properties, safety,
small impact on the Earths environment, and their economic advantages. Su-
percritical carbon dioxide with a critical temperature near room temperature can
be used as an alternative for toxic organic solvents in the fields of separation,
reaction and material processing. Supercritical water with a high critical tem-
perature and pressure can decompose refractory harmful organics easily and
depolymerize polymers to monomers and oligomers rapidly. This fluid has been
applied to waste treatment, recycling of plastics, inorganic material processing,
VI Preface
October 2001
.............................................. 1
1.1 Introduction.......................................................................................... 1
1.1.1 What is a Supercritical Fluid? ................................................... 1
1.1.2 Studies of Supercritical Fluids at the Molecular Level ............. 2
1.2 Solvation Structure from Spectroscopy ............................................... 3
1.2.1 Introduction ............................................................................... 3
1.2.2 Electronic Transitions ............................................................... 4
1.2.3 Vibrational Spectra.................................................................. 10
1.3 Solvation Structure from Molecular Simulations............................... 18
1.3.1 Molecular Interactions in Supercritical Fluids ........................ 18
1.3.2 Introduction to Molecular Simulation ..................................... 23
1.3.3 Solvation Structure in Supercritical Fluids.............................. 30
1.4 Static Properties of Supercritical Fluids............................................. 36
1.4.1 Excess Thermodynamic Quantities ......................................... 37
1.4.2 Solubility ................................................................................. 42
1.4.3 Adsorption............................................................................... 47
1.5 Dynamic Properties of Supercritical Fluids ....................................... 51
1.5.1 Dynamics of Clusters in Supercritical Fluids.......................... 51
1.5.2 Diffusion and Viscosity........................................................... 59
References ................................................................................................. 64
.................................................. 71
2.1 Thermophysical Properties of Supercritical Fluids............................ 71
2.1.1 Behavior of Supercritical Fluids.............................................. 71
2.1.2 Measurement of the Critical Point of Liquid and Vapor ......... 77
2.2 Phase Equilibria for a Mixture with a Supercritical Fluid ................. 78
2.2.1 Phase Rule ............................................................................... 78
2.2.2 Phase Equilibria and Phase Diagrams ..................................... 79
2.2.3 Experimental Phase Diagrams for a Binary Mixture .............. 84
2.3 Measurement of Phase Equilibria ...................................................... 85
2.3.1 Static Method .......................................................................... 85
2.3.2 Dynamic Method..................................................................... 90
VIII Contents
.......................................127
3.1 Viscosity ...........................................................................................127
3.1.1 Definition and General Behavior of Viscosity .......................128
3.1.2 Measurement of Viscosity......................................................131
3.1.3 Correlation..............................................................................138
3.1.4 Critical Anomaly of Viscosity................................................142
3.1.5 Remarks..................................................................................146
3.2 Thermal Conductivity .......................................................................147
3.2.1 Definition and Units of Thermal Conductivity ......................147
3.2.2 Measurement of Thermal Conductivity .................................148
3.2.3 General Behavior of Thermal Conductivity...........................154
3.2.4 Correlation..............................................................................157
3.2.5 Critical Anomaly of Thermal Conductivity ...........................166
3.3 Binary Diffusion Coefficient ............................................................172
3.3.1 Definition of Binary Diffusion Coefficients ..........................173
3.3.2 Measurement of Binary Diffusion Coefficient.......................174
3.3.3 Correlations ............................................................................181
3.3.4 Pseudo-Binary Diffusion Coefficients in Mixture Solvents...191
3.3.5 Critical Anomaly of Diffusion Coefficient ............................193
3.3.6 Remarks..................................................................................198
References ................................................................................................199
Contents IX
s ..................... 207
4.1 Principles for Supercritical Fluid Separation ................................... 207
4.1.1 Introduction ........................................................................... 207
4.1.2 Solubility of a Nonvolatile Compound
in a Supercritical Fluid .......................................................... 207
4.1.3 Solubility of a Solid Solute Mixture
in a Supercritical Fluid .......................................................... 210
4.1.4 Fluid-Liquid Equilibria for a Ternary Mixture..................... 214
4.1.5 Adsorption in the Presence of a Supercritical Fluid.............. 216
4.1.6 Supercritical Fluid Extraction ............................................... 218
4.1.7 Supercritical Fluid Fractionation of Polymers ...................... 221
4.1.8 Multistaged Countercurrent Extraction ................................. 222
4.1.9 Chromatographical Separation Using Supercritical Fluid..... 223
4.1.10 Reduction of Organic Solvent Usage in Extraction .............. 224
4.2 Process Development Studies for Separation of Chemicals ............ 224
4.2.1 Introduction ........................................................................... 224
4.2.2 Separation of Organic + Water Liquid Mixtures................... 224
4.2.3 Crystallization Separation of Aromatic Hydrocarbons ......... 226
4.2.4 Supercritical Fluid Adsorption Process ................................. 231
4.2.5 Polymer Processing ............................................................... 234
4.2.6 Treatment of Various Waste Streams.................................... 237
4.3 Extraction and Separation of Natural Products ................................ 239
4.3.1 Phase Equilibria for Components in Natural Materials......... 239
4.3.2 Solid Material Processing...................................................... 242
4.3.3 Liquid Material Processing ................................................... 246
4.3.4 Pressure Swing Adsorption ................................................... 256
4.4 Separation and Analysis by Supercritical Fluid Chromatography ... 260
4.4.1 Introduction ........................................................................... 260
4.4.2 Characteristics of Supercritical Fluid Chromatography ........ 260
4.4.3 Instrumentation...................................................................... 266
4.4.4 Control of Retention and Selectivity ..................................... 273
4.4.5 Measurement of Solubility and Phase Behavior
Using Supercritical Fluid Chromatography Techniques ....... 274
References ............................................................................................... 276
.................................. 281
5.1 Fractionation, Debindering and Drying ........................................... 281
5.1.1 Fractionation of Polymers ..................................................... 281
5.1.2 Phase Separation of Polymer Solutions................................. 283
X Contents
..........................................................347
6.1 Reactions and Reaction Theory in Supercritical Fluids ....................347
6.1.1 Introduction ............................................................................347
6.1.2 Characteristics of Reactions in Supercritical Fluids...............347
6.1.3 Reaction Mechanism and Reaction Rate
in Supercritical Fluids ............................................................350
6.2 Characteristics of Supercritical Fluids as Reaction Solvents ............357
6.2.1 Introduction ............................................................................357
6.2.2 Supercritical Carbon Dioxide.................................................360
6.2.3 Supercritical Water.................................................................360
6.2.4 Supercritical Methanol ...........................................................362
6.3 Oxidation and Hydrolysis Reactions in Supercritical Water ............364
6.3.1 Oxidation and Related Reactions ...........................................364
6.3.2 Hydrolysis Reactions..............................................................374
6.4 Organic and Catalytic Reactions in Rupercritical Carbon Dioxide ..381
6.4.1 Introduction ............................................................................381
6.4.2 Recent Advances in Organic Reactions
in Supercritical Fluids ............................................................383
6.4.3 Homogeneous Catalytic Reactions in Supercritical Fluids ....388
6.4.4 Concluding Remarks ..............................................................402
Contents XI
................................................................................................... 437
............................................................................................... 441
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g((r ) radial distribution function
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i, j component of fluid
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1.4 Static Properties of Supercritical Fluids 47
The enrichment of substances onto a solid surface from a fluid is called ad-
sorption. The surface potential that attracts molecules is due to dispersion,
induction and electrostatic interactions between solid atoms and molecules.
Since molecular concentrations obey the Boltzmann distribution law in a clas-
sical equilibrium system, substances that attractively interact with a surface are
preferentially concentrated in the first monolayer on the surface where the po-
tential is the deepest. This explains the reason why substances are enriched on
the surface from gases diluted in an inert gas; however, the understanding of
adsorption characteristics of substances diluted in a supercritical fluid (SCF)
requires two more factors: the competitive adsorption of solvent molecules in
the adsorbed phase and the enhanced solubility in the SCF phase. It is essen-
tially important to recognize that the adsorption in SCF is characterized by
mixed-gas adsorption.
Adsorption equilibrium in an SCF is determined from the thermodynamic
criterion of equilibrium: the equality of the chemical potentials of each sub-
stance in two phases, i.e. the adsorbed and fluid phases. Therefore, the surface
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102 2 Phase Equilibria and Static Properties
Correlation results of vapor-liquid equilibria for CO2 (1) + linalool (2) [12]. Re-
printed from: High-pressure vaporliquid equilibria for carbon dioxide + linalool: Y. Iwai,
N. Hosotani, T. Morotomi, Y. Koga, Y. Arai, J. Chem. Eng. Data (American Chemical So-
ciety) , 900 (1994).
iV Py i iL Px i , (2.4.8)
where xi and y i are the mole fractions of component i in the liquid phase
and vapor phase, respectively, and superscripts V and L denote the vapor
phase and liquid phase, respectively. The vapor-liquid equilibria can be calcu-
lated if i can be evaluated by an appropriate equation of state.
Figure 2.4.1 shows the correlation results of vapor-liquid equilibria for
CO2 (1) + linalool (2) by the PR equation of state using the conventional mixing
rules with two interaction parameters, k12 and l12 [12, 13]. The properties of li-
nalool are estimated by the method of Lydersen and Edmister [14], a kind of
group contribution method. The interaction parameters, k12 and l12 , are treated
as the adjustable parameters and they are determined to give good representation
of experimental data. The experimental data are correlated with good agreement
by using the interaction parameters ( k12 = 0.053, l12 = -0.035; 313.2 K), ( k12 =
0.046, l12 = -0.038; 323.2 K), and ( k12 = 0.051, l12 = -0.027; 333.2 K).
Several empirical methods using the fluid density or solubility parameter have
been proposed as correlation or prediction methods of solubilities of the solid
component in the supercritical fluid. The relationship between solubility, y 2
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acridine 106 Candida cylindacea (CCL) 404,
activated carbon 216, 232 406
activation volume 382, 383 capacity factor 264
activity coefficient 110 carbon dioxide (CO2)
adsorption 4751, 216, 244 supercritical see super-
competitive 47, 50 critical CO2
equilibrium constant 253 carbon monooxide (CO) 172, 367
adsorption separation 231 catalytic reaction
adsorption/desorption enzyme 402, 403, 405
process 252 heterogeneous 403, 415
aerogel 295 homogeneous 388
aerosol OT (AOT) 404, 412 phase transfer 402
aggregate 403 CC bond formation 362, 396,
alcogel 293 400
alkylation 362 cellulose 376
FriedelCrafts 396, 420
ChapmanEnskog theory 138,
anthracene 212, 307 160, 173, 423
argon (Ar) 167, 172 chemical potential 42, 47, 98,
196, 354
azeotropic point 214, 226
chemical recycling 362
azobis(butyronitrile)
(AIBN) 386, 402 citronellol 407
citrus oil 244, 251
cluster 4, 5,15, 34, 51, 60, 107,
162
Buckinghams approach 13 definition of 52
benzene 49, 58, 177, 187, 218, effect in reaction 348, 362,
287 384, 386
benzoic acid 104 coadsorption effect 48
benzonitrile 375 collision cross section 160
benzophenone 384 column efficiency 223
benzyl radical 353 compressibility
bisphenol A (BPA) 374, 380 factor 98
bubble point 80, 88 isothermal 1, 41, 73, 145,
254, 382
convection 148, 166
correlation length 145, 162
440 Subject Index