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Ostgard et al. 233In conclusion, the treatment of activated Ni, activated Co and Ni/SiO 2 catalystswith formaldehyde improves the primary amine selectivity of nitrile hydrogenation.This treatment works better for the activated Ni catalyst than it did for the activatedCo and these sponge-type catalysts respond better to it than the Ni/SiO 2 . The bestmodifiers (e.g., formaldehyde) are those that decompose into strongly adsorbingcompounds (e.g., CO) and the presence of hydrogen in the modifying compound isbeneficial. The improved primary amine selectivity appears to be caused byelectronic and/or steric effects such as the formation of smaller ensembles via thedeposition of the appropriate carbonaceous residues on the catalyst. While thistreatment improves the primary amine selectivity for aliphatic nitriles, it enhancesthe primary amine selectivity for aromatic nitriles even more so as seen by the 99.7%yield of Grewe diamine from pynitrile.Experimental SectionThe hydrogenation of pynitrile was carried out in an autoclave with either 5 grams ofan activated Ni (B 113 W), 10 grams of an activated Co (B 2112 Z) or 8 grams of aNi/SiO 2 catalyst under the conditions described in Table 1. Only in the case of theacetone treated activated Ni catalyst was the amount increased to 6 grams for thehydrogenation of pynitrile. Benzaldehyde, pyridine-3-carbonitrile and valeronitrilewere hydrogenated with 5.7 to 6.0 grams, 5.3 grams and from 20 to 21.9 grams of anactivated Ni catalyst respectively according to the conditions in Table 1. Themodification treatments were carried out as the aqueous suspensions of the catalystwith the modifier under the conditions described in Table 2.AcknowledgmentsThe authors thank DSM Nutritional Products Ltd. and Degussa AG for thepermission to present this work.References1. http://www.dsm.com/en_US/html/dnp/prod_vit_b1.htm2. http://www.chm.bris.ac.uk./webprojects2002/schnepp/viatminb1.html3. V. Tanphaichitr, Thiamin, in Modern Nutrition in Health and Disease, 9 th ed.,William & Wilkins, Baltimore, 1999, 391-399.4. M. Kimura, Y. Itokawa and M. Fujiwara, J.Nutr.Sci.Vitaminol, 36, 17-24 (1990)5. J.H. Hui, Encyclopedia of Food Science and Technology, John Wiley, New York,1992.6. Degischer, O.G. and Roessler, F. EP 1108469 to Hoffmann-La Roche AG(2000).7. L.J. Richter and W. Ho, J. Chem. Phys, 83, 5, 2165-2169 (1985).8. J.T. Yates and D.W. Goodman, J.Chem. Phys., 73, 10, 5371-5375 (1980).9. A. Bandara, S. Katano, J. Kubota, K. Onda, A. Wada, K. Domen and C. Hirose,Chem. Phys Lett., 290, 261-267 (1998).
234 Hydrogenation of Pynitrile10. A. Bandara, S. Dobashi, J. Kubota, K. Onda, A. Wada, K. Domen, C. Hirose andS.S. Kano, Surf. Sci., 387, 312-319 (1997).11. A. Bandara, S.S. Kano, K. Onda, S. Katano, J. Kubota, K. Domen, C. Hirose andA. Wada, Bull. Chem. Soc. Jpn., 75, 1125-1132 (2002).12. D. Ostgard, M. Berweiler and S. Laporte, Degussa AG, unpublished results.13. R.H. Newton, B.F. Dodge, J.Am. Chem. Soc., 55, 4747-4759 (1933).14. S. Ruozhi, D. Ostgard and G.V. Smith, Chemical Industries (Dekker), 47 (Catal.Org. React.), 337-349 (1992).
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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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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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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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Wang et al. 233. Catalytic Hydrogen
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Wang et al. 25The rate expressions
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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. 47was practically
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Gőbölös et al. 51Figure 2 NMR sp
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56Hydrotalcite-like Catalysts[A n-
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58Hydrotalcite-like Catalystssample
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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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84Phenol Benzoylationconsecutive Fr
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86Phenol BenzoylationThis does not
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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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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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180 Hydrogenation of Dehydrolinaloo
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Cao, White, Wang and Frye 28933. Se
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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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322 Dendrimer TemplatesThe 100 cm -
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328Rearrangement of 3,4-Epoxy-1-But
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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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378 Polyurethane from Natural OilMe
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386 Carbonylation of Chloropinacolo
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406“Green” Catalysts for Biodie
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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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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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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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482 Reductive AlkylationSince the p
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502 Electroreductive Catalytic Ullm
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504 Electroreductive Catalytic Ullm
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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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