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Robitaille, Clément, Chapuzet and Lessard 283Results and DiscussionReduction of nitroaryl groupsNitrobenzene (1) was used as a model to determine the best conditions for the“chemical catalytic hydrogenation” (CCH) using the Raney Cu alloy. In this work,we used ethanol as organic co-solvent because it is greener than methanol. The bestconditions for CCH were 0.05 M KOH in ethanol-water (45:55 v/v) (pH ≈ 12.5), atroom temperature and under a nitrogen atmosphere, using an amount of alloycorresponding to 3 equation of Al. The conversion was complete after 5 h and anilinewas obtained in a quantitative yield (100% by vapor phase chromatography). TheECH of nitrobenzene at Raney Cu electrodes in alkaline aqueous methanol givesaniline in a nearly quantitative yield (99%) (7).When these CCH conditions were applied to o-iodonitrobenzene (1), o-iodoaniline (2) together with iodoaniline (4) and nitrobenzene (1) were obtained inthe yields indicated in Scheme 1 (88% mass balance), which corresponds to a 62%selectivity for the formation of o-iodoaniline (3). Under the same conditions, theECH of o-iodonitrobenzene (2) gave aniline (90% yield) as the sole product. Therewas complete hydrogenolysis of the C−I bond (no selecti-vity). Thus, in basicmedium (pH ≈ 12.5), CCH method is much more selective than ECH. However, inweakly acidic medium (pH 3, pyridine.HCl buffer), it has been reported that ECH ata RCu cathode in methanol-water 95:5 (v/v) gave o-iodoaniline in a 97% yield (1, 3).NO 2NH 2NH 2 NO 2II2 3 4 1CCH (pH 12.5) 55% 28% 5%ECH (pH 12.5) 0% 90% 0%ECH (pH 3) (1, 3) 97% n.d n.dScheme 1The CCH of p-nitroacetophenone (5) (Scheme 2) was inefficient and unselectivegiving p-aminoacetophenone (6) in about 20% yield together with some 10-12% ofunindentified compounds (30% mass balance). Attempts to recover more materialwere unsuccessful. The ECH at a RCu cathode in an alkaline (0.28 M KOH, pH ≈13.5) MeOH-H 2 O (1.5% of H 2 O) solution was reported to give exclusively p-aminoacetophenone(6) (79% yield of isolated product) (3,8).OONO 2NH 25 CCH (pH 12.5) 20% 6ECH (pH 13.5) (3,8) 79%Scheme 2
284 Chemoselective HydrogenationThe CCH and ECH of p-cyanonitrobenzene (7) at pH 12-13 gave the threeproducts shown in Scheme 3 with low selectivities for the formation of p-cyanoaniline (8) respectively of 8-13% (82% mass balance) and 7% (65% massbalance). In neutral medium, the ECH of 7 has been reported to be very efficient,giving only p-cyanoaniline (8) in a quantitative yield (1, 3).NCNO 2NH 2NH 2NH 2HN NHCCNN7 8 910CNCCH (pH 12.5) 36-47% 17-8%29-27%ECH (pH 12.5) 27% 10% 38%ECH (pH 6) (1, 3) 100% n.d n.dScheme 3The CCH and ECH of the o-nitrodioxolane 11 was very selective giving onlythe corresponding o-aminodioxolane 12 (Scheme 4). No cleavage of the dioxolanering giving the aminodiol 13 and cyclohexanone by hydrogenolysis of the benzylicC−O bond was observed. Such cleavage did occur upon ECH on a RNi electrodeunder the same basic conditions (60% yield of 13).ONO 2OONH 2OHONH 2OH11 12CCH (pH 12.5) 100%ECH (pH 12.5) 92%13Scheme 4The CCH of 2-(p-nitrobenzyl)-2-nitropropane (14) allowed the selectivereduction of the nitroaryl group, without reduction of the tertiary nitroalkyl group,giving 85-93% of 2-(p-aminobenzyl)-2-nitropropane (15) (Scheme 5). No diamino
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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
Page 260 and 261: Ostgard et al. 233In conclusion, th
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Page 264 and 265: Kuusisto, Mikkola and Salmi 237100A
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Page 269 and 270: 242 1-Phenyl-1-Propyneof cis-β-met
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Page 294 and 295: Rothenberg et al. 267Table 1. Parti
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Page 298 and 299: Angueira and White 27131. Novel Chl
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Page 304 and 305: Angueira and White 277Table 1. 27 A
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Page 323 and 324: 296Chiral Ferrocene LigandsTable 1.
Page 325 and 326: 298Chiral Ferrocene Ligandsprevents
Page 327 and 328: 300Chiral Ferrocene LigandsConclusi
Page 329 and 330: 302Chiral Ferrocene Ligandsextracte
Page 331 and 332: 304 Catalyst Library DesignIn gas p
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Page 343 and 344: 316 Dendrimer TemplatesWe are devel
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Page 355 and 356: 328Rearrangement of 3,4-Epoxy-1-But
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334Rearrangement of 3,4-Epoxy-1-But
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336Rearrangement 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
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348Heteropoly AcidsSOOO O+ +OS1 2 3
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350Heteropoly AcidsTable 3. Acylati
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352Heteropoly AcidsSiO 2 is the bes
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Diez, Di Cosimo and Apesteguia 3554
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Diez, Di Cosimo and Apesteguia 357T
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Diez, Di Cosimo and Apesteguia 359A
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Diez, Di Cosimo and Apesteguia 3630
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378 Polyurethane from Natural OilMe
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380 Polyurethane from Natural Oilco
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382 Polyurethane from Natural Oilfr
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384 Polyurethane from Natural OilTh
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386 Carbonylation of Chloropinacolo
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396 Recycling Homogeneous Catalysts
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406“Green” Catalysts for Biodie
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416 Production of BiodieselTable 1.
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418 Production of Biodieselto a mas
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420 Production of BiodieselEthyl st
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422 Production of Biodiesel10080Sel
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424 Production of Biodieselproduct
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Marincean et al. 42747. Glycerol Hy
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Marincean et al. 429Experimental Se
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Marincean et al. 431neutralize all
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Marincean et al. 433suggesting that
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Kocal 43748. Developing Sustainable
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Kocal 439description of the four st
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Kocal 441metallurgy in parts of the
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Kocal 443that capital investment co
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Kocal 4455. J.J. Siirola, An Indust
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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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