Handbook of Solvents - George Wypych - ChemTech - Ventech!

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14.21.1 Use of solvents in manufacture of drugs 979 14.21.1.2 Where are solvents used in the manufacture of pharmaceutical drugs? 14.21.1.2.1 Intermediates of synthesis, DS and excipients 14.21.1.2.1.1 General points Raw materials are now produced by the chemical industry and involve the use of solvents at different steps in their production. These materials are usually produced by: • chemical synthesis • an extraction process, a fermentation process • or a biotechnology process The goal of this chapter is, of course, not to deal with the criteria for selection in relationship to their use in particular chemical reactions or extraction processes but rather to stress that impurities present in solvents could have an impact on the purity of the substances obtained, on their stability and potentially on their safety. These three concepts are of paramount importance in the pharmaceutical field. A list of solvents which are commonly used in the chemical industry 5 is presented in Table 14.21.1.1. Table 14.21.1.1. Solvents commonly used in the chemical industry Alcohols Ethanol Butanol 2-Ethylhexanol Isobutanol Isopropanol Methanol Propanol Propyleneglycol Amide Dimethylformamide Amine Pyridine Aliphatic hydrocarbons Cyclohexane Hexane Ketones Acetone Methyl ethyl ketone Methyl isobutyl ketone Methyl isopropyl ketone Mesityl oxide Ethers 1.4-Dioxane Butyl ether Ethyl ether Diisopropyl ether Tetrahydrofuran Tert-butyl methyl ether (MTBE) Nitriles Acetonitrile Water Halogenated solvents Ethylene bromide Chloroform Ethylene chloride Dichloromethane Tetrachloroethylene Carbon tetrachloride Trichloroethylene Sulphur-containing Dimethylsulfoxide Aromatics hydrocarbons Toluene Xylene Esters Ethyl acetate It is generally relatively easy to know for pharmaceutical industry the nature of solvents to be looked for in a DS because it produces itself the active component or because it
980 Michel Bauer, Christine Barthélémy can have by contract an access to the DS Mater File or because there is a compendial monograph giving occasionally some indications (e.g., search for benzene in carbomers). As a consequence of the ICH Guideline Q3C 4 dealing with the residual solvents in pharmaceutical products (see Chapter 16.2), the use of solvents of class I (solvents to be avoided) like benzene is no more possible. It is known that carbopol resins (carbomer), used to modify the rheology of polar systems and as a binder in sustained release tablets, were up to now polymerized in benzenic medium. In the current quality of poloxamers it was possible to retrieve up to 1000 ppm of benzene. The ICH limit being 2 ppm, it was impossible to achieve this goal. The manufacturers have consequently developed new polymerization media 6 containing either ethyl acetate alone or a mixture of ethyl acetate and cyclohexane, the first one belonging to class III (no safety concern), the second one belonging to class II (ICH limit 3880 ppm). 14.21.1.2.1.2 Criteria of purity This is a difficult matter. Purity in chemistry is an ideal concept referring to a situation where a product consists of one type of molecules only. This is a theoretical situation which can only be EXPERIMENTALLY approached more or less closely. 7 The purity of a product is a relative notion and is dependant on the analytical methods used and their performances. More practically the quality finally chosen for a solvent will depend on the specific use for which this solvent is intended to be utilized. 8 A solvent is considered sufficiently pure if it does not contain impurities able in nature and in quantity to interfere on the admissible quality of the product in the manufacture of which it participates. 7 14.21.1.2.1.3 Solvents as reaction medium In this case the solvents should have a range between the melting point and the boiling point as extended as possible and a good thermal and chemical stability. The purity should be of good degree but could depend on the step considered of the global synthesis. As an example let us consider the case of the dimethylformamide (DMF). 5 If it is used in reactions evolving in anhydrous media, it will be mandatory to control the level of water at the ppm level. The specification regarding the water content will be of course loosened if the DMF in the chemical step considered is used in conjunction with water as reaction media. We will see further that solvents contain actually a lot of chemical impurities which could be reactive vis a vis the main molecule undergoing the chemical reaction and leading to additional impurities other than those coming from the mechanism of reaction itself. 14.21.1.2.1.4 Solvents for crystallization They should be carefully chosen in such a way that they show a high solubility at high temperature and a low solubility at low temperature of the substance to be crystallized or recrystallized. Of course the solvent should be absolutely inert and of the highest achievable purity for at least two reasons: • The first one being identical to the one mentioned for solvents as reaction media: possibility to produce other impurities. • The second one being linked to the crystallization process itself. It is well known that the presence of impurities whatever the origin could have serious effects on the nucleation and growth process. We will tell a little bit more about that further in the text.
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HANDBOOK OF SOLVENTS George Wypych,
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Preface Although the chemical indus
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Preface xxix contain or to have use
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1654 Acknowledgments 10.3 Solvent e
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Table of Contents Preface .........
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Table of contents iii 4.3 Polar sol
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Table of contents v 7.2.1.1 Rheolog
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Table of contents vii 9.4.4 Solvent
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Table of contents ix 12.2.2.1 Chemi
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Table of contents xi 14.4.3.1 Intro
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Table of contents xiii 14.19 Paints
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Table of contents xv 15.1.20 Gas ch
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Table of contents xvii 17.2.2 Movem
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Table of contents xix 18.4.7 Dry cl
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Table of contents xxi 20.7.1 Introd
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Table of contents xxiii 21.4.1.3 Pr
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Table of contents xxv 23.2.1.3 Sour
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2 Christian Reichardt aliphatic nit
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4 Christian Reichardt the knowledge
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2 Fundamental Principles Governing
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2.1 Solvent effects on chemical sys
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2.2 Molecular design of solvents 37
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2.3 Basic physical and chemical pro
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66 George Wypych Aprotic/Protic Ter
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68 George Wypych Biodegradability T
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70 George Wypych Figure 3.2.1. Sche
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72 George Wypych Figure 3.3.4. Simp
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74 George Wypych Synthetic routes a
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76 George Wypych Property minimum V
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96 Tilman Hahn, Konrad Botzenhart,
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98 Tilman Hahn, Konrad Botzenhart,
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General Principles Governing Dissol
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4.1 Simple solvent characteristics
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4.2 Effect of system variables on s
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4.3 Polar solvation dynamics 133 tr
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4.3 Polar solvation dynamics 135 Fo
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4.3 Polar solvation dynamics 137 at
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4.3 Polar solvation dynamics 139 li
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4.3 Polar solvation dynamics 141 Fi
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4.3 Polar solvation dynamics 143 Fi
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4.3 Polar solvation dynamics 145 ta
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4.4 Measurement of solvent activity
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Solubility of Selected Systems and
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5.1 Solubility parameters 245 ln P
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5.1 Solubility parameters 247 Accep
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5.1 Solubility parameters 249 media
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5.1 Solubility parameters 251 Polym
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5.2 Prediction of solubility parame
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5.3 Methods of calculation of solub
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5.4 Mixed solvents - polymer solubi
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5.5 The phenomenological theory of
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306 E. Ya. Denisyuk, V. V. Tereshat
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318 V V Tereshatov, V Yu. Senichev,
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328 Vasiliy V. Tereshatov, Valery Y
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340 George Wypych where: τM the mo
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342 George Wypych ξ 0.55 0.5 0.45
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344 George Wypych Self-diffusion co
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346 George Wypych Temperature, K 31
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348 George Wypych Diffusion distanc
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350 George Wypych • evaporation-i
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352 George Wypych Water volume frac
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354 George Wypych Diffusion coeffic
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356 Semyon Levitsky, Zinoviy Shulma
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386 Seung Su Kim, Jae Chun Hyun 7.3
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388 Seung Su Kim, Jae Chun Hyun rat
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390 Seung Su Kim, Jae Chun Hyun The
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392 Seung Su Kim, Jae Chun Hyun whe
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394 Seung Su Kim, Jae Chun Hyun beg
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396 Seung Su Kim, Jae Chun Hyun 7.3
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398 Seung Su Kim, Jae Chun Hyun Fig
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404 Seung Su Kim, Jae Chun Hyun sol
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406 Seung Su Kim, Jae Chun Hyun Tab
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408 Seung Su Kim, Jae Chun Hyun and
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410 Seung Su Kim, Jae Chun Hyun to
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412 Seung Su Kim, Jae Chun Hyun The
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414 Seung Su Kim, Jae Chun Hyun cau
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416 Seung Su Kim, Jae Chun Hyun Nu
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Interactions in Solvents and Soluti
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8.2 Basic simplifications of quantu
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8.2 Basic simplifications of quantu
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8.4 Two-body interaction energy 425
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8.5 Three- and many-body interactio
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8.6 The variety of interaction pote
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8.6 The variety of interaction pote
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8.7 Theoretical and computing model
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8.8 Practical applications of model
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8.9 Liquid surfaces 493 to study th
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8.9 Liquid surfaces 495 The potenti
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8.9 Liquid surfaces 497 out of equi
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8.9 Liquid surfaces 499 tions) of t
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8 Interactions in solvents and solu
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8 Interactions in solvents and solu
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9 Mixed Solvents Y. Y. Fialkov, V.
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9.2 Chemical interaction between co
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9.2 Chemical interaction between co
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9.3 Physical properties of mixed so
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9.4 Mixed solvent influence on the
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9.5 The mixed solvent effect on the
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9 Mixed solvents 563 22 Minkin V.,
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10 Acid-base Interactions 10.1 GENE
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10.1 General concept of acid-base i
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10.1 General concept of acid-base i
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10.2 Effect of polymer/solvent acid
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10.3 Solvent effects based on pure
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10.4 Acid-base equilibria in ionic
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11 Electronic and Electrical Effect
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11.1 Theoretical treatment of solve
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11.2 Dielectric solvent effects 681
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12 Other Properties of Solvents, So
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12.1 Rheological properties, aggreg
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12.2 Chain conformations of polysac
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738 Roland Schmid Figure 13.1.1. Re
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740 Roland Schmid HB interactions,
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742 Roland Schmid AN = -133.8 - 0.0
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744 Roland Schmid ated by the macro
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746 Roland Schmid turns out, polar
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748 Roland Schmid Packing density
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750 Roland Schmid tween calculated
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752 Roland Schmid over the solute-s
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754 Roland Schmid of the empirical
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756 Roland Schmid From X-ray and ne
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758 Roland Schmid Table 13.1.5. Sol
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760 Roland Schmid ΔG = ΔG + ΔG [
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762 Roland Schmid very recent paper
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764 Roland Schmid Solvent ΔvH/RT
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766 Roland Schmid E r = E i + E s [
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768 Roland Schmid from the explicit
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770 Roland Schmid sequently, there
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772 Roland Schmid simulations. 188-
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774 Roland Schmid 23 N. A. Lewis, Y
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776 Roland Schmid 132 R. R. Dogonad
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778 Michelle L. Coote and Thomas P.
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798 Maw-Ling Wang 13.3 EFFECTS OF O
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800 Maw-Ling Wang [13.3.2] Inverse
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802 Maw-Ling Wang Both cation and a
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804 Maw-Ling Wang Table 13.3.2. Eff
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806 Maw-Ling Wang Table 13.3.3. Ext
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808 Maw-Ling Wang Table 13.3.5. Eff
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810 Maw-Ling Wang reacts with pheno
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812 Maw-Ling Wang Figure 13.3.3. Ef
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814 Maw-Ling Wang the organic solve
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816 Maw-Ling Wang crease. Therefore
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818 Maw-Ling Wang (F) Polymerizatio
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820 Maw-Ling Wang Table 13.3.16. Sy
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822 Maw-Ling Wang 13.3.1.4 Effect o
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824 Maw-Ling Wang Table 13.3.19 Eff
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826 Maw-Ling Wang quaternary salt c
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828 Maw-Ling Wang Table 13.3.24. Ef
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830 Maw-Ling Wang Solvent Dielectri
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832 Maw-Ling Wang ied. 82,83,97,101
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834 Maw-Ling Wang substitution, suc
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836 Maw-Ling Wang (2) the ion excha
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838 Maw-Ling Wang REFERENCES 1 A. A
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840 Maw-Ling Wang 101 D. C. Sherrin
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842 Norio Tsubokawa [13.4.2] PAI is
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844 Norio Tsubokawa Table 13.4.2. I
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846 Norio Tsubokawa more easily tha
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848 George Wypych methyl amyl keton
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850 George Wypych Peel strength, N/
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852 George Wypych 8 P Enenkel, H Ba
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854 George Wypych Table 14.2.2. Tot
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856 M Matsumoto, S Isken, JAMdeBont
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866 Tilman Hahn, Konrad Botzenhart
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872 Tsuneo Yamane 14.4.3 CHOICE OF
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874 Tsuneo Yamane Very trace amount
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876 Tsuneo Yamane It has been shown
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878 Tsuneo Yamane [ ( kcat Km) ( kc
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880 George Wypych 11 A. Zaks, in En
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882 George Wypych rected towards im
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884 Kaspar D. Hasenclever than 55°
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886 Kaspar D. Hasenclever The same
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888 Kaspar D. Hasenclever Figure 14
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890 Kaspar D. Hasenclever Computer
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892 Kaspar D. Hasenclever • Solve
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894 Martin Hanek, Norbert Löw, And
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920 George Wypych 20 N. L�w, EPP
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922 George Wypych Table 14.9.2. Rep
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924 Phillip J. Wakelyn, Peter J. Wa
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926 Phillip J. Wakelyn, Peter J. Wa
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Page 1005: 978 Michel Bauer, Christine Barthé
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Page 1025 and 1026: 998 An Li This discussion is intend
Page 1027 and 1028: 1000 An Li Trade Name Cosolvent vol
Page 1029 and 1030: 1002 An Li Figure 14.21.2.1. Effect
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1030 Mohamed Serageldin, Dave Reeve
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1040 George Wypych Table 14.27.2. R
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1050 George Wypych Table 14.32.5. T
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1052 George Wypych The traditional
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1054 George Wypych The acidity of b
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1056 George Wypych except water whi
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1058 George Wypych solution is 2.73
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1060 George Wypych presence of igni
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1062 George Wypych method of determ
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1064 George Wypych used. A thermal
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1066 George Wypych 15.1.26 REFRACTI
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1068 George Wypych Table 15.1.1. Ty
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1070 George Wypych Wexcluded solven
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1072 George Wypych 25 ASTM D 2108-9
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1074 George Wypych 68 ASTM D 3844-9
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1076 George Wypych BS 506-2.84. Met
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1078 Myrto Petreas 15.2 SPECIAL MET
Page 1107 and 1108:
1080 Myrto Petreas In short, biolog
Page 1109 and 1110:
1082 Myrto Petreas cients of some i
Page 1111 and 1112:
1084 Myrto Petreas lection at the a
Page 1113 and 1114:
1086 Myrto Petreas and legal reperc
Page 1115 and 1116:
1088 Myrto Petreas • The solvent
Page 1117 and 1118:
1090 Myrto Petreas of time after ex
Page 1119 and 1120:
1092 Myrto Petreas even after log-l
Page 1121 and 1122:
1094 Myrto Petreas 26 M Petreas, J
Page 1123 and 1124:
1096 James L. Botsford In Europe ma
Page 1125 and 1126:
1098 James L. Botsford Figure 15.2.
Page 1127 and 1128:
1100 James L. Botsford cussed. Neit
Page 1129 and 1130:
1102 James L. Botsford n Ave. Var.
Page 1131 and 1132:
1104 James L. Botsford (Calleja et
Page 1133 and 1134:
1106 James L. Botsford Table 15.2.2
Page 1135 and 1136:
1108 James L. Botsford the test is
Page 1137 and 1138:
1110 James L. Botsford Table 15.2.2
Page 1139 and 1140:
1112 James L. Botsford Geiger, D. L
Page 1141 and 1142:
1114 Christine Barthélémy, Michel
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Page 1145 and 1146:
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Page 1151 and 1152:
Page 1153 and 1154:
1126 George Wypych n-heptane molecu
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1128 George Wypych MEK P PA Fat-fre
Page 1157 and 1158:
1130 Michel Bauer, Christine Barth
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Page 1161 and 1162:
Page 1163 and 1164:
Page 1165 and 1166:
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Page 1175 and 1176:
17 Environmental Impact of Solvents
Page 1177 and 1178:
17.1 The environmental fate and mov
Page 1179 and 1180:
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Page 1183 and 1184:
Page 1185 and 1186:
Page 1187 and 1188:
Page 1189 and 1190:
17.2 Fate-based management 1163 dat
Page 1191 and 1192:
17.2 Fate-based management 1165 bre
Page 1193 and 1194:
17.2 Fate-based management 1167 gra
Page 1195 and 1196:
17.3 Environmental fate of glycol e
Page 1197 and 1198:
Page 1199 and 1200:
Page 1201 and 1202:
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Page 1205 and 1206:
Page 1207 and 1208:
Page 1209 and 1210:
Page 1211 and 1212:
Page 1213 and 1214:
Page 1215 and 1216:
17.4 Organic solvent impacts on tro
Page 1217 and 1218:
Page 1219 and 1220:
Page 1221 and 1222:
Page 1223 and 1224:
Page 1225 and 1226:
Page 1227 and 1228:
18 Concentration of Solvents in Var
Page 1229 and 1230:
18.1 Measurement and estimation of
Page 1231 and 1232:
Page 1233 and 1234:
Page 1235 and 1236:
Page 1237 and 1238:
Page 1239 and 1240:
Page 1241 and 1242:
Page 1243 and 1244:
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Page 1249 and 1250:
Page 1251 and 1252:
Page 1253 and 1254:
18.2 Prediction of organic solvents
Page 1255 and 1256:
Page 1257 and 1258:
Page 1259 and 1260:
Page 1261 and 1262:
18.3 Indoor air pollution by solven
Page 1263 and 1264:
Page 1265 and 1266:
Page 1267 and 1268:
Page 1269 and 1270:
Page 1271 and 1272:
Page 1273 and 1274:
Page 1275 and 1276:
Page 1277 and 1278:
18.4 Solvent uses with exposure ris
Page 1279 and 1280:
Page 1281 and 1282:
Page 1283 and 1284:
Page 1285 and 1286:
Page 1287 and 1288:
Page 1289 and 1290:
Page 1291 and 1292:
Page 1293 and 1294:
1268 Carlos M. Nu�ez ter or habit
Page 1295 and 1296:
1270 Carlos M. Nu�ez CAS No. Chem
Page 1297 and 1298:
Page 1299 and 1300:
Page 1301 and 1302:
Page 1303 and 1304:
Page 1305 and 1306:
Page 1307 and 1308:
1282 Carlos M. Nu�ez tronic circu
Page 1309 and 1310:
1284 Carlos M. Nu�ez EPA Region 6
Page 1311 and 1312:
1286 Carlos M. Nu�ez i.e., entire
Page 1313 and 1314:
1288 Carlos M. Nu�ez Table 19.6.
Page 1315 and 1316:
1290 Carlos M. Nu�ez Schedule Sou
Page 1317 and 1318:
1292 Carlos M. Nu�ez The CAA prov
Page 1319 and 1320:
1294 Carlos M. Nu�ez CWA to estab
Page 1321 and 1322:
1296 Carlos M. Nu�ez amended to i
Page 1323 and 1324:
1298 Carlos M. Nu�ez Figure 19.5.
Page 1325 and 1326:
1300 Carlos M. Nu�ez environmenta
Page 1327 and 1328:
1302 Carlos M. Nu�ez For comparis
Page 1329 and 1330:
1304 Carlos M. Nu�ez tives. Four
Page 1331 and 1332:
1306 Carlos M. Nu�ez • Program
Page 1333 and 1334:
1308 Carlos M. Nu�ez 31 Federal R
Page 1335 and 1336:
1310 Carlos M. Nu�ez HSWA Hazardo
Page 1337 and 1338:
Page 1339 and 1340:
20 Toxic Effects of Solvent Exposur
Page 1341 and 1342:
20.1 Toxicokinetics, toxicodynamics
Page 1343 and 1344:
Page 1345 and 1346:
Page 1347 and 1348:
Page 1349 and 1350:
Page 1351 and 1352:
20.2 Cognitive and psychosocial out
Page 1353 and 1354:
Page 1355 and 1356:
Page 1357 and 1358:
20.3 Pregnancy outcome following so
Page 1359 and 1360:
Page 1361 and 1362:
Page 1363 and 1364:
Page 1365 and 1366:
Page 1367 and 1368:
Page 1369 and 1370:
Page 1371 and 1372:
Page 1373 and 1374:
Page 1375 and 1376:
Page 1377 and 1378:
Page 1379 and 1380:
20.4 Industrial solvents and kidney
Page 1381 and 1382:
Page 1383 and 1384:
Page 1385 and 1386:
Page 1387 and 1388:
20.5 Lymphohematopoietic study of w
Page 1389 and 1390:
Page 1391 and 1392:
Page 1393 and 1394:
Page 1395 and 1396:
Page 1397 and 1398:
Page 1399 and 1400:
20.6 Chromosomal aberrations 1375 2
Page 1401 and 1402:
20.6 Chromosomal aberrations 1377 p
Page 1403 and 1404:
20.7 Hepatotoxicity 1379 8 Mitelman
Page 1405 and 1406:
20.7 Hepatotoxicity 1381 to convert
Page 1407 and 1408:
20.7 Hepatotoxicity 1383 Table 20.7
Page 1409 and 1410:
20.7 Hepatotoxicity 1385 toxicity o
Page 1411 and 1412:
20.7 Hepatotoxicity 1387 early pote
Page 1413 and 1414:
20.7 Hepatotoxicity 1389 vents. It
Page 1415 and 1416:
20.7 Hepatotoxicity 1391 19 Slater
Page 1417 and 1418:
20.8 Solvents and the liver 1393 20
Page 1419 and 1420:
20.8 Solvents and the liver 1395 Cu
Page 1421 and 1422:
20.8 Solvents and the liver 1397 th
Page 1423 and 1424:
20.8 Solvents and the liver 1399 cu
Page 1425 and 1426:
Page 1427 and 1428:
Page 1429 and 1430:
20.9 Toxicity of environmental solv
Page 1431 and 1432:
Page 1433 and 1434:
Page 1435 and 1436:
Page 1437 and 1438:
Page 1439 and 1440:
Page 1441 and 1442:
Page 1443 and 1444:
21 Substitution of Solvents by Safe
Page 1445 and 1446:
21.1 Supercritical solvents 1421 So
Page 1447 and 1448:
21.1 Supercritical solvents 1423 Fi
Page 1449 and 1450:
Page 1451 and 1452:
Page 1453 and 1454:
21.1 Supercritical solvents 1429 K
Page 1455 and 1456:
21.1 Supercritical solvents 1431 ai
Page 1457 and 1458:
21.1 Supercritical solvents 1433 Th
Page 1459 and 1460:
21.1 Supercritical solvents 1435 wh
Page 1461 and 1462:
21.1 Supercritical solvents 1437 *
Page 1463 and 1464:
21.1 Supercritical solvents 1439 In
Page 1465 and 1466:
21.1 Supercritical solvents 1441 21
Page 1467 and 1468:
21.1 Supercritical solvents 1443 Ta
Page 1469 and 1470:
21.1 Supercritical solvents 1445 Re
Page 1471 and 1472:
21.1 Supercritical solvents 1447 Re
Page 1473 and 1474:
21.1 Supercritical solvents 1449 ta
Page 1475 and 1476:
Page 1477 and 1478:
Page 1479 and 1480:
Page 1481 and 1482:
Page 1483 and 1484:
21.2 Ionic liquids 1459 85 M. Polia
Page 1485 and 1486:
21.2 Ionic liquids 1461 be used. Th
Page 1487 and 1488:
21.2 Ionic liquids 1463 Figure 21.2
Page 1489 and 1490:
21.2 Ionic liquids 1465 Table 21.2.
Page 1491 and 1492:
21.2 Ionic liquids 1467 been utiliz
Page 1493 and 1494:
21.2 Ionic liquids 1469 One specifi
Page 1495 and 1496:
21.2 Ionic liquids 1471 lustrates t
Page 1497 and 1498:
21.2 Ionic liquids 1473 these alloy
Page 1499 and 1500:
21.2 Ionic liquids 1475 ( ) ln = K
Page 1501 and 1502:
21.2 Ionic liquids 1477 According t
Page 1503 and 1504:
21.2 Ionic liquids 1479 Acidic melt
Page 1505 and 1506:
21.2 Ionic liquids 1481 21 C.L. Hus
Page 1507 and 1508:
21.2 Ionic liquids 1483 110 G.P. Li
Page 1509 and 1510:
21.3 Oxide solubilities in ionic me
Page 1511 and 1512:
Page 1513 and 1514:
Page 1515 and 1516:
Page 1517 and 1518:
Page 1519 and 1520:
Page 1521 and 1522:
21.4 Alternative cleaning technolog
Page 1523 and 1524:
Page 1525 and 1526:
Page 1527 and 1528:
Page 1529 and 1530:
Page 1531 and 1532:
1508 Klaus-Dirk Henning Application
Page 1533 and 1534:
1510 Klaus-Dirk Henning 22.1.2.2 Ad
Page 1535 and 1536:
1512 Klaus-Dirk Henning point the a
Page 1537 and 1538:
1514 Klaus-Dirk Henning Figure 22.1
Page 1539 and 1540:
Page 1541 and 1542:
1518 Klaus-Dirk Henning Table 22.1.
Page 1543 and 1544:
Page 1545 and 1546:
1522 Klaus-Dirk Henning Regeneratio
Page 1547 and 1548:
1524 Klaus-Dirk Henning • activit
Page 1549 and 1550:
1526 Klaus-Dirk Henning adsorption
Page 1551 and 1552:
Page 1553 and 1554:
Page 1555 and 1556:
Page 1557 and 1558:
1534 Klaus-Dirk Henning vent conden
Page 1559 and 1560:
Page 1561 and 1562:
Page 1563 and 1564:
Page 1565 and 1566:
1542 Klaus-Dirk Henning 12 H. Krill
Page 1567 and 1568:
1544 Isao Kimura Table 22.2.1. Appl
Page 1569 and 1570:
1546 Isao Kimura Table 22.2.2. Typi
Page 1571 and 1572:
1548 Isao Kimura 22.2.4 SOLVENT REC
Page 1573 and 1574:
1550 Isao Kimura Figure 22.2.9. Flo
Page 1575 and 1576:
1552 Isao Kimura • Difficult in d
Page 1577 and 1578:
1554 Isao Kimura Figure 22.2.12. Fl
Page 1579 and 1580:
1556 Denis Kargol Figure 22.3.1. So
Page 1581 and 1582:
1558 Denis Kargol Figure 22.3.4. AS
Page 1583 and 1584:
1560 K. A. Magrini, et al. and Olli
Page 1585 and 1586:
1562 K. A. Magrini, et al. ysis of
Page 1587 and 1588:
1564 K. A. Magrini, et al. Figure 2
Page 1589 and 1590:
1566 K. A. Magrini, et al. On the l
Page 1591 and 1592:
1568 K. A. Magrini, et al. ating te
Page 1593 and 1594:
1570 K. A. Magrini, et al. Cummings
Page 1595 and 1596:
1572 Hanadi S. Rifai, Charles J. Ne
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1618 Barry J. Spargo, James G. Muel
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Page 1655 and 1656:
1632 George Wypych number of 1 or e
Page 1657 and 1658:
1634 George Wypych In addition to t
Page 1659 and 1660:
1636 George Wypych d diameter of gr
Page 1661 and 1662:
1638 George Wypych wax-containing c
Page 1663 and 1664:
1640 George Wypych product of inven
Page 1665 and 1666:
1642 George Wypych selection of sol
Page 1667 and 1668:
1644 George Wypych fining processes
Page 1669 and 1670:
1646 George Wypych requires several
Page 1671 and 1672:
1648 George Wypych crease color str
Page 1673 and 1674:
1650 George Wypych tion. The patent
Page 1675 and 1676:
1652 George Wypych 75 M Solinas, T
Page 1677 and 1678:
1658 Index anhydrous form 282 anili
Page 1679 and 1680:
1660 Index 1-chlorooctane 826 chlor
Page 1681 and 1682:
1662 Index term 750 dipole moment 1
Page 1683 and 1684:
1664 Index Friedel-Crafts alkylatio
Page 1685 and 1686:
1666 Index method 245 laser 689 lat
Page 1687 and 1688:
1668 Index O octane 127,185 1-octan
Page 1689 and 1690:
1670 Index Prandtl number 392 Praus
Page 1691 and 1692:
1672 Index function 137 preferentia
Page 1693 and 1694:
1674 Index change 350 time scale 33
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