(Springer Series in Materials Processing) Professor Yasuhiko Arai, Professor Takeshi Sako (auth.), Professor Yasuhiko Arai, Professor Takeshi Sako, Dr. Yoshihiro Takebayashi (eds.)-Supercritical Fluid.pdf

Springer Series in
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Springer Series in
materials processing
Series Editors: H. Warlimont E. Weber W. Michaeli
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Low-Pressure Synthetic Diamond. Manufacturing and Applications

Editors: B. Dischler and C. Wild
Supercritical Fluids Molecular Interactions, Physical Properties, and New Applications
Editors: Y. Arai, T. Sako, and Y. Takebayashi
Purication Process and Characterization of Ultra High Purity Metals. Application of Basic
Science to Metallurgical Processing
Editors: Y. Waseda and M. Isshiki
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Y. Arai T. Sako Y. Takebayashi (Eds.)
Supercritical Fluids
Molecular Interactions, Physical Properties,
and New Applications
With 301 Figures and 37 Tables
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
Professor Dr. E. Weber

Materials Science and Mineral Engineering, University of California
587 Evans Hall, Berkeley, CA 94720-1760, USA
Professor Dr.-Ing. Walter Michaeli

Institut fr Kunststoffverarbeitung, RWTH Aachen
Pontstrae 49, 52056 Aachen, Germany
ISSN 1434-9795
ISBN 978-3-642-62515-2 ISBN 978-3-642-56238-9 (eBook)
DOI 10.1007/978-3-642-56238-9
Library of Congress Cataloging -in-Publication-Data
Supercritical uid science and technology / Y. Arai, T. Sako, Y. Takebayashi (eds.). p. cm. (Springer series in
materials processing, ISSN 1434-9795) Includes bibliographical references and index.
ISBN 3540412484 (alk. paper) 1. Supercritical uids. I. Arai, y. (Yasuhiko) II. Sako, T. (Takeshi) III. Takebayashi,
Y. (Yoshihiro) IV. Series. TP156.E8.S837 2002 660.28423dc21 00-049717
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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
hydrogen production from heavy hydrocarbons, and so on. Supercritical

methanol has a critical temperature between those of carbon dioxide and water.
It is employed in selective methylation with or without a catalyst and in
chemical recycling of waste plastics.
To date several books on supercritical fluid science and its applications
have been published in specific areas. This text, on the other hand, attempts to
provide six well-balanced chapters so that the reader can obtain an overview of
some of the main future areas in supercritical fluid science and its potential for
supporting the development of new technologies. The first section (Chaps. 1-3)
provides a description of supercritical fluids and their interactions which is
based on our knowledge after many years of research in the spectroscopic,
molecular simulation, and thermodynamic fields. The second section (Chaps.
4-6) covers applications in extractions, separations, materials processing, and
reactions. It is our hope that the text will contribute to our understanding of
fluids in their supercritical state and help to inspire both young and established
researchers to explore and develop new chemical and related processes which
are friendly to our environment. We would like to take this opportunity to thank
all the authors for their participation. We would also like to thank Springer for
their guidance and encouragement during the preparation of the manuscript.
Fukuoka Yasuhiko Arai

Hamamatsu Takeshi Sako
Tsukuba Yoshihiro Takebayashi
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
2.4 Prediction of Phase Equilibria.............................................................98

2.4.1 Fundamental Equations ............................................................98
2.4.2 Empirical Equation of State .....................................................99
2.4.3 Mixing Rules..........................................................................101
2.4.4 Correlation of Vapor-Liquid Equilibria ................................101
2.4.5 Correlation of Solubility of the Solid Component
in a Supercritical Fluid ...........................................................102
2.4.6 Correlation of Entrainer Effect...............................................105
2.5 Group Contribution Method..............................................................108
2.5.1 Prediction of Excess Gibbs Free Energy Using the Group
Contribution Method (ASOG and UNIFAC) .........................110
2.5.2 EOS-Group Contribution Method ..........................................111
2.5.3 Group Contribution Equation of State (GC-EOS) .................119
References ................................................................................................122
.......................................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
5.1.3 Devolatilization of Polymers..................................................285

5.1.4 Debindering of Molded Fine Ceramics ..................................289
5.1.5 Drying of Alcogels .................................................................293
5.2 Crystallization Using a Supercritical Fluid .......................................299
5.2.1 Rapid Expansion of Supercritical Solutions (RESS) .............299
5.2.2 Gas Anti-Solvent (GAS) ........................................................310
5.3 Processing of Polymeric Materials Using Supercritical Fluids.........319
5.3.1 Solubility and Diffusivity of Gases in Polymers....................320
5.3.2 Crystallization of Plastics Induced by Supercritical Fluid .....324
5.3.3 Batchwise Production of Microcellular Thermoplastics ........326
5.4 Hydrothermal Synthesis of Metal Oxide...........................................331
5.4.1 Principle of Hydrothermal Synthesis
in Supercritical Water.............................................................331
5.4.2 Key Features of Hydrothermal Synthesis
5.4.3 Applications of Hydrothermal Synthesis
References ................................................................................................340
..........................................................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
6.5 Reactions of Enzymes and Molecular Aggregates

in Supercritical Fluids...................................................................... 403
6.5.1 Introduction ........................................................................... 403
6.5.2 Enzymatic Reactions in Supercritical Carbon Dioxide ......... 405
6.5.3 Reactions in Microemulsions Formed
in Supercritical Fluids ........................................................... 411
6.5.4 Concluding Remarks ............................................................. 414
6.6 Heterogeneous Catalysis in Supercritical Fluids.............................. 415
6.6.1 Introduction ........................................................................... 415
6.6.2 Fischer-Tropsch Synthesis in Supercritical Fluids ............... 416
6.6.3 Synthesis of Fine Chemicals in Supercritical Fluids............. 420
6.6.4 Kinetics of Heterogeneous Catalysis
in Supercritical Fluids ........................................................... 421
6.6.5 Concluding Remarks ............................................................. 425
References ............................................................................................... 426
................................................................................................... 437
............................................................................................... 441
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1.4 Static Properties of Supercritical Fluids 47
Monte Carlo calculation results for reduced mean-square end-to-end separations

of paraffins at 308.2 K [23]. Reprinted from: Y. Iwai, Y. Koga, Y. Arai: Monte Carlo
simulation of nparaffins and higher alcohols in supercritical carbon dioxide: Fluid Phase
Equilibria (Elsevier Science) 267 (1996).
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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4.2 Process Development Studies for Separation of Chemicals 233
Comparison of breakthrough curves for toluene using activated carbons regener-

ated by steam as well as supercritical CO2 [11]. Reprinted from: C. H. Tan, D. C. Lion:
Regeneration of activated carbon loaded with toluene by supercritical carbon dioxide,
Separation Sci. Technol. (Marcel Dekker) , 111 (1989).
on an anion exchange resin (Arnberlite IRA-904) and second the indole-free

oil entered the bed of acidic adsorbent (10 wt% aluminum sulfate supported
on silica gel).
After the ion exchange resin and the adsorbent were saturated with indole
and quinoline, the feed of methylnaphthalene oil was stopped and adsorbed
indole and quinoline were recovered by solvent extraction using methanol and
tetrahydrofuran respectively. Figure 4.2.7 [12] shows a schematic process
flow. Slightly acidic indole and basic quinoline can be selectively recovered
by continuous supercritical CO2 extraction with the two fix beds of adsorb-
ents. The recovery of indole and quinoline can be done using methanol and
tetrahydrofuran as entrainers.
Novel process for separation of indole and quinoline from crude naphthalene oil
[12]
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272 4 Extraction and Separation Using Supercritical Fluids
Effect of sample volume on peak shape in packed column SFC. Conditions: Su-
perpak Crest C18 (15 cm 4.6 mm i.d., 5 m), 60 C, CO2, 140 atm, 3 ml/min, UV
210 nm, 500 ppm alkylbenzenes in methylene chloride
mobile phase. The allowable injection volume without degradation of peak

shape seems to be smaller in SFC than in LC. Figure 4.4.11 shows the effect
of sample volume on the peak shape in packed-column SFC with a conven-
tional analytical column, indicating that the sample volume should be less than
10 1 for this column [14], although this may be dependent on the properties
of the sample solvent and the chromatographic conditions.
For open tubular column SFC, the situation is more severe, because of
the small column dimensions. A commercially available injector with a sam-
ple volume of 0.06 l is often used. However, injecting such a small volume
makes it difficult to analyze trace components. A peak as low as 100 pg can be
detected with FID. If it is desired to have a detection limit of 100 ppb in terms
of solute concentration in the solution injected, the required injection volume
would be 1 l. Direct injection of this volume corresponding to the 0.5 m
length of a 50 m i.d column will spread solute over a meter or more of the
column, resulting in the skewed or split peaks. So far various injection tech-
niques allowing the injection of volumes of the order of a microliter have been
developed; these are usually based on separating the solvent and solutes and
then reconcentrating the solutes at the column inlet as a narrow band followed
by pressure programming. Figure 4.4.12 shows an example with one of the in-
jection methods, in which a joint with a small volume was placed ahead of the
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5.2 Crystallization Using a Supercritical Fluid 307
Influence of degree of dilution R on forming anthracene crystals: ( ) R =0, ( )

R = 2 [8]
For the purpose of developing a new separating method, RESS crystallization

experiments were performed for the naphthalene + phenanthrene system using
the same apparatus as shown in Fig. 5.2.3 [7]. The morphology as well as the
composition of the collected solid particles were analyzed by optical micros-
copy and gas chromatography. The maximum purity of naphthalene in the
formed solid mixture reached 0.96 mole fraction, which is 1.08 times higher
than the saturated solubility. Figure 5.2.7 shows solid particles produced by
widely varying the feed concentration of the solute mixture to the nozzle. Pure
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5.2 Crystallization Using a Supercritical Fluid 309
Crystals of anthracene + phenanthrene mixture obtained via RESS [8]
A mixture of anthracene + phenanthrene forms a solid solution in solid-liquid

equilibrium. The solubility and RESS behavior for this solid solution were in-
vestigated by Liu and Nagahama [8]. As the number of Gibbs degrees of free-
dom in the solid-fluid equilibrium for CO2 + anthracene + phenanthrene is
equal to three, the solubility of this mixture can be determined when given not
only the temperature and pressure, but also a fixed solid composition. This
means the solubilities of anthracene + phenanthrene in CO2 change depending
on the solid composition.
Figure 5.2.8 is a photograph of crystals formed by RESS. Comparing
Fig. 5.2.8 with Figs. 5.2.6 (pure anthracene) and 5.2.7 (c) (pure phenanthrene),
the crystal shapes and sizes in Fig. 5.2.8 are completely different from those in
Figs. 5.2.6 and 5.2.7 (c). This suggests that the crystals of Fig. 5.2.8 may not
be a mixture of pure solids but may be a solid solution. Also X-ray diffraction
observation gave further support for this fact.
One advantage of RESS is the relatively narrow distribution of particle size

with small average value (about micrometers). Furthermore, it is very rapid
and dose not require a vacuum. From a process management standpoint, crys-
tallization and drying occur simultaneously and leave products free from sol-
vent. And also RESS reduces the waste volumes required for filtration and
washing by simplifying solid separation [9].
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368 6 Reactions in Supercritical Fluids
Arrhenius plots for direct oxidation and water-gas shift reaction in the SCWO of
carbon monoxide [1] Reprinted from: Carbon monoxide oxidation in supercritical water: H.
R. Holgate, P. A. Webley, J. W. Tester and R. K. Helling, Energy and Fuels (American
Chemical Society) , 586 (1992).
Normalized hydrogen decay profiles in the SCWO of hydrogen at 550 C [2].

[H2O]0 = 4.2510-3 mol/cm3. p: [H2]0 = 3.0610-6, [O2]0 = 1.5510-6 mol/cm3; : [H2]0 =
2.0610-6, [O2]0 = 1.0410-6 mol/cm3; : [H2]0 = 1.06510-6, [O2]0 = 0.5410-6 mol/cm3.
Curves are exponential fits to data
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acetone 12, 114, 180 cage effect 353, 382, 386, 402
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
corresponding-state principle 140, diffusion coefficient 5964, 127,

154, 170 172199
cosolvent 210, 239, 358, 360, 389 binary 172, 187, 191
Coulombic interaction 10, 19 critical anomaly of 193
countercurrent extraction effect in reaction 285, 348
process 247 mutual 60, 196
multistaged 222 of gas in polymer 324
critical anomaly 1 of isomers 195
of diffusion coefficient 193 pseudo-binary 191
of thermal conductivity 166 self- 21, 29, 33, 51, 59, 186,
of viscosity 142
187
critical compressibility factor 2 diffusion coefficient correlation
critical constant 2, 441 181190
Dymond free volume
critical enhancement 60, 74, 158
equation 181
of thermal conductivity 158,
empirical correlation 181
161, 164, 166
Schmidt number correlation
critical exponent 146 173, 186
critical locus 79, 276 WilkeChang equation 181,
critical opalescence 77 423
critical point (CP) 1, 71, 79, 359 diffusion coefficient measurement
crossover pressure 228 174181
crystal violet (CV) 412 capillary tube method 180
crystallization 226, 299324 near critical region 193
of plastics 324 Taylor dispersion method
cyclization 396 173, 193
diffusion-limited reaction 352
dimethylnaphthalene 44, 233
debindering 289 dioxin 372
DebyeHuckel expression 355 drying 293, 309
degree of polymerization 236
dehydration 214, 226, 362
dehydrogenation 362 enantiomeric excess (ee) 393, 407
density fluctuation 1 enantioselectivity 391
detection limit 272 enhancement factor 208
dielectric constant 7, 11, 127 ensemble
effect in reaction 331, 348, grand cannonical (mVT) 48
350, 354, 358, 365, 369 microcannonical (NVE) 22,
local 4, 5, 76, 356 28
dielectric continuum model 5 NPT 28, 39
DielsAlder reaction 357, 383, NVT 21, 22, 28, 48
386 entrainer 105, 107, 210, 262
enzyme 402, 403, 405
equation of motion 25
Subject Index 441
equation of state (EOS) 41, 196 Fourier's law 147

BenedictWebbRubin Freundlich-type adsorption
(BWR) 37, 100, 138 model 244
empirical 37, 99, 146 fugacity 42, 98, 101
group contribution (GC) 109, fugacity coefficient 98, 103, 111,
119 354
PengRobinson (PR) 99,
109, 213, 243, 250
porposed by Yu et al. 104,
105, 213 gas antisolvent (GAS) 299, 310
SanchezLacombe (SL) 321
319
SoaveRedlichKwong gas chromatography (GC) 223,
(SRK) 99, 109, 111, 213, 250 260
van der Waals (vdW) type Gibbs phase rule 78
99, 101, 120 glass transition pressure 320
virial expansion type 99 glass transition temperature 320
esterification 385, 406, 420 glucose 376
ethane 12, 38, 84, 116, 172 group contribution (GC)
ethanol 84, 115, 118, 214, 224 method 108
euctic mixture 307 ASOG 109, 110, 119
excess Gibbs free energy 110 equation of state
excess internal energy 40 (EOS) 109111
UNIFAC 109, 110
excess thermodynamic
quantities 37
extended critical region 161
HartreeFock calculation 9, 20
HeckMizoroki reaction 400
fatty acid 121, 186, 239 Henry's constant 42, 321
Ficks law 173, 243, 287, 352 heterogeneously nucleated
bubble 329
first solvation shell 9, 56
hexane 189, 192
FischerTropsch reaction 416
high-density polyethylene
fitting in time domain (FTD)
(HDPE) 321
method 175
high-pressure liquid chromatogra-
flame ionization detector (FID)
phy (HPLC) 178, 376
176, 263, 269
homogeneously nucleated
FloryHuggins interaction
bubble 329
parameter 320
hydration 362
FloryHuggins theory 241
hydroformylation 395
fluidliquid equilibrium
(FLE) 214 hydrogel 293
fluorescence spectroscopy 6 hydrogen 332, 367
fluorocarbon 170 hydrogen atom transfer 384, 395
fluoropolymer 402 hydrogen bond 16, 30, 348, 362
formic acid 393
442 Subject Index
hydrogenation 360, 362, 390 liquid-liquid equilibrium

asymmetric 391 (LLE) 88
enantioselective 421 local density enhancement 5, 51,
hydrolysis 8, 362, 374 56
hydrothermal synthesis 331340 lower critical end point
hydroxybenzoic acid 227 (LCEP) 81, 286
lower critical solution temperature
(LCST) 285
indole 233 lumping strategy 371
infrared (IR) spectroscopy 4, 16,
408, 414
interaction parameter 43, 101, 241 maleic anhydride 383
ion product 76, 348, 361, 365, mass transfer 218, 243, 415
375 mean square displacement
isomer separation 226, 231 (MSD) 59
isoprene 357, 383 meniscus observation 77
metal oxide fine particle 331
metastable zone 311
KamletTaft value 406 metathesis 397
KamletTaft * value 5, 360, 362 methane 172, 367
Kay's rule 284 methanol 106, 296, 367
KirkwoodBuff theory 61 supercritical see supercritical
Kirkwood's expression 354, 375 methanol
Kramer's turnover 350 methyl acrylate 357
methyl palmitate 120
micelle 389
Michael addition 385
Langmuirtype adsorption model
5, 9, 217, 244, 254, 320 microcellular plastic 319, 326
law of rectilinear diameters 77 microemulsion 411
LennardJones fluid 28, 30, 39, mixing rule 98, 101, 241
59, 181 conventional 101, 108
HuronVidal 101, 111
LennardJones potential function
local mole fraction 101
19, 24, 43, 48, 63
MHV1 and MHV2 114
light scattering detector 267 MR1 115
limonene 241, 250 PRASOG 119
linalool 102, 250 PSRK 115
linear low-density polyethylene WangSandler 117
(LLDPE) 234 mixture critical curve 275
linoleic acid 192 modifier 262
lipase 406 molded alumina 290
liquid chromatography (LC) 223, molecular dynamics (MD) simula-
260 tion 3, 7, 20, 30, 51, 59, 197
Subject Index 443
molecular interaction 3, 18, 23 PausonKhand reaction 396

molecular orbital (MO) calculation PCB 239, 372
10, 16, 18 pentane 118
monodisperse polymer 236 peppermint oil 244
Monte Carlo (MC) simulation 3, periodic boundary condition 21,
10, 23, 36, 43, 48 24, 53
phase diagram 1
for binary mixture 84
N,N-dimethylaminobenzonitrile phase equilibrium measurement
(DMABN) 6 8598
naphthalene 104, 209, 229, 305 dynamic method 90
naphtol 44, 104 flowtype method 96
natural product 239 phase recirculation method
neutron diffraction 30, 32 91
static analytical method 86
Newtons law 128
static nonanalytical method
nitrogen 154, 172, 321, 327 89
nitrous oxide (N2O) 143, 172 phase equilibrium prediction 98
NMR spectroscopy 32, 180, 362, 108
395 phase separation 73, 78
Norrish type I photolysis 386 of polymer solution 283
number of degrees of freedom 28, phenanthrene 210, 229, 308
78, 212, 230, 309 phenol 44, 238, 369
number of theoretical plates 260 photo Fries rearrangement 386
photoisomerization 385
Pitzers ascentric factor 101, 105
oligomer processing 236 plasticizing effect 285
oligomeric cyclic ether plate height 262
(OCE) 285 polarity parameter (ET) 4, 12, 18,
Onsagers reaction field theory 5, 360
7, 12, 18 polydimethyl siloxane 281
open tubular column 260 polyethylene terephthalate
orange oil 250, 255 (PET) 324, 330, 362, 374, 380
oxidation 399, 421 polyvinyl acetate (PVAc) 287
supercritical water see super- polyvinyl benzoate 320
critical water
polyethylene (PE) 320
oxygen 172, 332
polymer
devolatilization of 285
foaming of 319
packed column 260 fractionation of 221, 234,
pair correlation function 32 281
paraffin 47, 116 polymerization 402, 412
partial molar volume 30 polymethylmethacrylate
partial oxidation 362 (PMMA) 236, 325
444 Subject Index
polypropylene (PP) 321 shrinking core model 246

polystyrene (PS) 286, 321, 327 silica gel 255
pore density 48 single crystal growth (SCG) 301
pore diffusion 243 slow expansion of supercritical
pressure drop 264 solutions (SESS) 301
pressure programming 267 SN2 reaction 9, 375
pressure swing adsorption soil remediation 238
(PSA) 256 solid solution 309
pressurization pattern 313 solubility 4247, 50, 102
propanol 122, 215 effect in material processing
PVT measurement 77, 136 299, 310
PVT relation 37 effect in reaction 360, 382,
pyrene 55 388
effect in separation 207, 227,
262, 274
enhanced by adsorption 47
quinoline 233 of gas in polymer 320
of isomers 44
solubility parameter 102, 106
radial distribution function 7, 9, solution model 106
11, 30, 45, 61 solvent composition programming
radical chain reaction 370 267
radical recombination 353 solvent/feed (S/F) ratio 249
Raman Spectroscopy 4, 11, 362, specific heat 142
369 at constant pressure 74, 148,
rapid expansion of supercritical 162
solution (RESS) 229, 299310 at constant volume 74
Rayleigh number 166, 170 spectral shift 4, 11, 356
reaction rate 352, 358, 365 speed of sound 75
reaction selectivity 358, 384 static structure factor 34
refractive index 267 stearic acid 108
restrictor 268 stearyl alcohol 109
retention time 263 stereoselectivity 404, 405
retrograde crystallization 227 StokesEinstein equation 174,
retrograde phenomenon 208, 253 181, 352
retrograde vaporization 228 sulfur hexafuloride (SF6) 171,
reverse solubility 321 172
supercritical antisolvent
(SAS) 285, 299
saturated liquid 71, 79, 129 supercritical aqueous solution 35,
saturated vapor 71, 79, 129 332
Schmidt number correlation 173, supercritical carbon dioxide
181, 186 (scCO2)
adsorption of 49
Subject Index 445
analytic potential function for supersaturation 300

18 surface diffusion 218, 243
binary diffusion coefficient in surface reaction 417
180195 surfactant 389, 388, 402, 411
diffusion coefficient in 60 syngas transfer 421
excess property of binary sys-
tem 38
number of cluster member in
55 Taylor dispersion method 173,
predicted phase equilibria for 193
114122 temperature inversion effect 208
properties of 347, 358 temperature programming 267
PVT diagram of 131, 361 tetracosane 117
reaction in 364, 381403 thermal conductivity 127, 147
solubility in 43, 104109, 172, 186, 348, 358
202213 background 159
thermal conductivity of 156 critical anomaly of 166
viscosity of 129 critical enhancement of 158,
supercritical fluid chromatography 161, 166
(SFC) 191, 216, 223, 236, 260 excess 158, 164
274 of dilute gas 160
supercritical fluid extraction (SFE) thermal conductivity correlation
172, 191, 218, 224259, 285 157
supercritical fluid separation 207 thermal conductivity measurement
259, 347 176, 148154, 166
supercritical methanol concentric cylinder method
KamletTaft parameter of 151, 166
363 parallel plates method 152,
properties of 359 166
reaction in 360 transient hot-wire method
supercritical water (SCW) 149, 166
dielectric constant of 76 thermal diffusivity 148, 161
ion product of 77, 361 thermal expansion coefficient 41,
isothermal compressibility of 73
73 toluene 116, 286
MD simulation for 31 tomato seed oil 246
oxidation (SCWO) 350, 364 transition metal complex 388
properties of 359 transition state theory 354, 383
PVT surface of 71 trifluoromethane (CHF3) 6, 12,
reaction in 350, 360, 365 139, 144
381
triple point 72
specific heat of 75
speed of sound of 76
thermal expansion coefficient
of 74 ultraviolet (UV) absorption detec-
tor 176, 267
446 Subject Index
ultraviolet (UV)-visible spectros- viscosity correlation

copy 310, 18, 107 Chung et al. 138
upper critical end point LeeThodos 138
(UCEP) 81 VesovicWakeham (VW)
upper critical solution temperature 140, 147
(UCST) 283 viscosity measurement 131138,
165
near critical region 142
van Deemter curve 263
van der Waals (vdW) interaction
19, 52 waste water treatment 237
van der Waals loop 36 water
vaporliquid coexistence region supercritical see supercritical
71, 80 water
vaporliquid equilibrium (VLE) watergas shift reaction 362, 367
78, 85, 101, 110, 214, 225
virial coefficient 22, 117, 119
viscometer xenon 172, 189
capillary-flow 131 xerogel 294
oscillating-body 131, 146 X-ray diffraction 32
viscosity 60, 127147, 160, 162, xylene 226
174, 186 xylenol 44
critical anomaly of 142
effect in reaction 348, 358,
386
excess 144
zeolite 231

(Springer Series in Materials Processing) Professor Yasuhiko Arai, Professor Takeshi Sako (auth.), Professor Yasuhiko Arai, Professor Takeshi Sako, Dr. Yoshihiro Takebayashi (eds.)-Supercritical Fluid.pdf

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(Springer Series in Materials Processing) Professor Yasuhiko Arai, Professor Takeshi Sako (auth.), Professor Yasuhiko Arai, Professor Takeshi Sako, Dr. Yoshihiro Takebayashi (eds.)-Supercritical Fluid.pdf

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Springer Series in

Low-Pressure Synthetic Diamond. Manufacturing and Applications

Series homepage http://www.springer.de/phys/books/ssmp/

With 301 Figures and 37 Tables

Professor Dr. E. Weber

Professor Dr.-Ing. Walter Michaeli

hydrogen production from heavy hydrocarbons, and so on. Supercritical

Fukuoka Yasuhiko Arai

2.4 Prediction of Phase Equilibria.............................................................98

5.1.3 Devolatilization of Polymers..................................................285

6.5 Reactions of Enzymes and Molecular Aggregates

Definitions of other symbols are presented on the spots.

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