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Hallett, Pollet, Eckert and Liotta 399Our fluorous silica technology was also tested (1) on the catalytic hydrogenationof styrene. The fluorous silica phase contained a fluorinated version of Wilkinson’scatalyst (Figure 3) deposited onto the surface of the fluorous silica. The organicphase consisted of styrene dissolved in cyclohexane. No fluorous solvent was used.F-(F 2 C) 6 -H 2 C-H 2 CPRhClFigure 3. Fluorinated Wilkinson’s catalyst33H 2 and then CO 2 pressure were applied, forming a GXL. The fluorinatedcatalyst then partitioned off of the fluorinated silica support and into the CO 2 -expanded organic phase. The reaction was assumed to occur in the expanded liquidphase in which reactants (styrene, hydrogen) and catalyst (fluorinated Wilkinson’scatalyst) are homogeneously present. After the reaction was completed, the pressurewas released and the catalyst then partitioned back onto the silica surface.The recyclability of the fluorinated catalyst was investigated. Five consecutiveruns were carried out successfully with the same initial fluorinated catalyst/silica.The styrene hydrogenation activity proved to be relatively consistent (TOF from250-400 h -1 ) for each of the five runs, indicating minimal loss of catalytic activity.Another way to omit the fluorous solvent would be to utilize a catalystimmobilization solvent that is not fluorinated, such as water. We demonstrated theapplication of a phase change after reaction permits facile recycle of hydrophiliccatalysts. This method is called OATS (Organic-Aqueous Tunable Solvent) (15).Changes in composition or temperature give relatively incomplete separations –the addition of CO 2 has a far more profound effect on system phase behavior. CO 2 ismiscible with most organics but virtually immiscible with water. Addition of CO 2can result in a phase separation of a miscible organic/water mixture (16), ordrastically change distribution coefficients in a two-phase organic/water system (17).In addition, it provides for benign recycle of hydrophilic organometallic catalysts(14). For example, with the traditional aqueous biphasic catalysis technique,popularized by the Ruhrchemie/Rhône-Poulenc process (18), catalyst recovery canbe achieved most easily by maintaining an aqueous catalyst-rich phase separate fromthe substrate-containing (nonpolar) organic phase. The catalyst is immobilized in anaqueous phase by modifying the catalyst ligands with one or more polarfunctionalities, such as sulfonate or carboxylate salts (19). This renders the catalystcompletely insoluble in the substrate- (and later product-) containing organic phase,so that decantation of the organic phase results in no loss of catalyst. The aqueouslayer can be recycled many times, yielding high catalyst turnover with little metallic
400 Recycling Homogeneous Catalystscontamination of the product. This “heterogenized” homogeneous system canimprove the lifetime of organometallic catalysts by orders of magnitude.The Ruhrchemie/Rhône-Poulenc process is performed annually on a 600,000metric ton scale (18). In this process, propylene is hydroformylated to formbutyraldehyde. While the solubility of propylene in water (200 ppm) is sufficient forcatalysis, the technique cannot be extended to longer-chain olefins, such as 1-octene(
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Catalysis ofOrganic Reactions
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14. Catalyst Manufacture: Laborator
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62. Catalysis of Organic Reactions,
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108. Metal Oxides: Chemistry and Ap
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CRC PressTaylor & Francis Group6000
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xiii14. The Transformation of Light
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xviien Catalisis y Petroquimica (UN
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xix56. Transition Metal Removal fro
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xxiiiChronology of Organic Reaction
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To Zsuzsanna and Tim
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Jones et al. 31. On the Use of Immo
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Jones et al. 5three-phase tests in
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Jones et al. 7In the HKR of rac-epi
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Jones et al. 9term performance char
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Jones et al. 115. A. S. Gruber, D.
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Moses et al. 132. Supported Re Cata
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Moses et al. 15perrhenate, followed
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Moses et al. 17SnCOSnMe 4≡SiOReO
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Moses et al. 19(AlOSi) of the cube.
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Moses et al. 212.510 3 k obs / s -1
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Wang et al. 233. Catalytic Hydrogen
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Wang et al. 25The rate expressions
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Wang et al. 27Schiff’s base forma
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Wang et al. 29AcknowledgementsWe gr
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32Halophosphite LigandsIn 1970, Pru
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34Halophosphite LigandsThe ligands,
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36Halophosphite LigandsTable 2 Temp
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38Halophosphite Ligands3. P. W. N.
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40Monolithic Bioreactorstrength for
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42Monolithic BioreactorMenten equat
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Gőbölös et al. 456. Highly Selec
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Gőbölös et al. 47was practically
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Gőbölös et al. 49noteworthy that
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Gőbölös et al. 51Figure 2 NMR sp
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Gőbölös et al. 53internal TMS in
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56Hydrotalcite-like Catalysts[A n-
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58Hydrotalcite-like Catalystssample
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Mantilla, Tzompantzi, Torres and G
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68Synthesis of MIBKwe examined the
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70Synthesis of MIBK1412Conversion (
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72Synthesis of MIBK4,4’-dimethyl
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74Synthesis of MIBKobtained for MIB
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Ardizzi et al. 7710. The Control of
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Ardizzi et al. 79type acidity at th
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Ardizzi et al. 81procedure describe
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84Phenol Benzoylationconsecutive Fr
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86Phenol BenzoylationThis does not
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II. Symposium on Catalytic Oxidatio
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92Oxidation with Microchannel Immob
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100 Propylene Partial OxidationThe
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102 Propylene Partial OxidationSiO
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104 Propylene Partial Oxidation0.01
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106 Propylene Partial Oxidation0.02
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108 Propylene Partial OxidationRefe
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110Oxidation of n-Pentanemethacryli
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112Oxidation of n-PentaneFReqox1ox2
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114Oxidation of n-Pentanethe presen
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116Oxidation of n-PentaneIn the mec
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118Oxidation of n-PentaneReferences
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120TEMPO Oxidation of Alcoholsthe u
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122TEMPO Oxidation of AlcoholsThe r
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124TEMPO Oxidation of Alcoholsany d
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126TEMPO Oxidation of Alcoholsconce
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128TEMPO Oxidation of AlcoholsMNT :
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130TEMPO Oxidation of Alcoholsuptak
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132Aminoalcohols to Aminocarboxylic
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142Bromine-Free TEMPO-Based Catalys
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148CO OxidationP25 TiO 2 , respecti
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150CO Oxidation0.02(a)21802110(b)21
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152CO Oxidationcarboxylate species
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Yamauchi 15519. 2006 Murray Raney A
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Yamauchi 157transformation is schem
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Yamauchi 159The X-ray diffraction p
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Yamauchi 161was -0.0009, -0.0032 an
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Yamauchi 163shown in Fig. 12. It wa
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Yamauchi 165These fine particles we
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168Nitrobenzene Hydrogenationfurthe
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170Nitrobenzene Hydrogenationhydrog
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172Nitrobenzene HydrogenationThe co
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174Nitrobenzene HydrogenationHence
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176Nitrobenzene Hydrogenation10. G.
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178 Hydrogenation of Dehydrolinaloo
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188Modeling Mass Transfer Hydrogena
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198 Fructose HydrogenationHOHCCH 2O
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200 Fructose HydrogenationTable 1.
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202 Fructose Hydrogenationmmol form
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204 Fructose Hydrogenationthe subst
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206 Fructose Hydrogenationcleave th
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208 Fructose Hydrogenationfulfills
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210 Fructose Hydrogenationis not th
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Disselkamp et al. 21324. Cavitating
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Disselkamp et al. 215column. In a p
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Disselkamp et al. 217selectivity es
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Disselkamp et al. 219hydrogenated (
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Disselkamp et al. 221A somewhat mor
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Disselkamp et al. 223Scheme 4.cis-2
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Disselkamp et al. 225conventional c
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Ostgard et al. 22725. The Treatment
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Ostgard et al. 229Table 1. The reac
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Ostgard et al. 231metal atoms. Thes
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Ostgard et al. 233In conclusion, th
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Kuusisto, Mikkola and Salmi 23526.
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Kuusisto, Mikkola and Salmi 237100A
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Kuusisto, Mikkola and Salmi 2399. B
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242 1-Phenyl-1-Propyneof cis-β-met
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244 1-Phenyl-1-Propynealkene. When
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Musolino, Apa, Donato and Pietropao
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Gőbölös and Margitfalvi 25329. R
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Gőbölös and Margitfalvi 255maxim
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Gőbölös and Margitfalvi 257Y=421
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Rothenberg et al. 26130. How to Fin
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Rothenberg et al. 263By dividing th
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Rothenberg et al. 265pre-define the
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Rothenberg et al. 267Table 1. Parti
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Rothenberg et al. 269Experimental S
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Angueira and White 27131. Novel Chl
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Angueira and White 273optimizedgeom
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Angueira and White 275F igure 4 - c
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Angueira and White 277Table 1. 27 A
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Angueira and White 279obtained from
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Robitaille, Clément, Chapuzet and
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Cao, White, Wang and Frye 28933. Se
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Cao, White, Wang and Frye 291Experi
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294Chiral Ferrocene Ligandsnew Twin
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296Chiral Ferrocene LigandsTable 1.
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298Chiral Ferrocene Ligandsprevents
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300Chiral Ferrocene LigandsConclusi
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302Chiral Ferrocene Ligandsextracte
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304 Catalyst Library DesignIn gas p
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306 Catalyst Library Designd−(b 0
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308 Catalyst Library DesignBasic Pr
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310 Catalyst Library DesignD in com
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312 Catalyst Library DesignCatalyst
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314 Catalyst Library Design27. S. H
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316 Dendrimer TemplatesWe are devel
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318 Dendrimer TemplatesThe differen
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320 Dendrimer TemplatesWe encounter
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322 Dendrimer TemplatesThe 100 cm -
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328Rearrangement of 3,4-Epoxy-1-But
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3382,5-Dimethyl-2,4-Hexadieneharves
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3402,5-Dimethyl-2,4-Hexadienestabil
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3422,5-Dimethyl-2,4-Hexadiene10086Y
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3442,5-Dimethyl-2,4-Hexadienereacti
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3462,5-Dimethyl-2,4-Hexadiene8. www
Page 375 and 376: 348Heteropoly AcidsSOOO O+ +OS1 2 3
Page 377 and 378: 350Heteropoly AcidsTable 3. Acylati
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Page 409 and 410: 382 Polyurethane from Natural Oilfr
Page 411 and 412: 384 Polyurethane from Natural OilTh
Page 413 and 414: 386 Carbonylation of Chloropinacolo
Page 423 and 424: 396 Recycling Homogeneous Catalysts
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Page 433 and 434: 406“Green” Catalysts for Biodie
Page 443 and 444: 416 Production of BiodieselTable 1.
Page 445 and 446: 418 Production of Biodieselto a mas
Page 447 and 448: 420 Production of BiodieselEthyl st
Page 449 and 450: 422 Production of Biodiesel10080Sel
Page 451 and 452: 424 Production of Biodieselproduct
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Page 475 and 476: 448Propylene Oxidation to POSupercr
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450Propylene Oxidation to POTable 1
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452Propylene Oxidation to PO
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Riermeier et al. 45550. catASium ®
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Riermeier et al. 457It is interesti
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Riermeier et al. 459Reaction of the
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Riermeier et al. 461References1. I.
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464 Chiral 2-Amino-1-Phenylethanolp
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466 Chiral 2-Amino-1-PhenylethanolI
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468 Chiral 2-Amino-1-Phenylethanola
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470 t-Butanol DehydrationResults an
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472 t-Butanol Dehydrationcomprises
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Pohlmann et al 47553. Leaching Resi
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Pohlmann et al 477this study. In th
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Pohlmann et al 479Experimental Sect
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482 Reductive AlkylationSince the p
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484 Reductive AlkylationTable 2. Re
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Wolf, Seebald and Tacke 48755. Acce
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Wolf, Seebald and Tacke 489100Norma
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Wolf, Seebald and Tacke 4911,88Figu
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Woods et al. 49356. Transition Meta
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Woods et al. 495Effect of oxidation
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Woods et al. 497
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Woods et al. 499removed the samples
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502 Electroreductive Catalytic Ullm
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504 Electroreductive Catalytic Ullm
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Catalysis of Organic Reactions 507A
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Catalysis of Organic Reactions 509K
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Catalysis of Organic Reactions 511T
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514 Keyword Indexcarboncarbon dioxi
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516 Keyword Indexethanolamine 16 13
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518 Keyword IndexNi, activated 25 2
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520 Keyword Indexsuccinimido ketone
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