Catalysis : an Integrated Approach to Homogeneous ...

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2 -CATALYTIC PROCESSES IN INDUSTRY 65 OAc L O AC OAc G O AC 1 1 OAc TsOH + CHO I CHo YHO OAc -A. OAc J NaOAc, HOAc Fig. 3.30. Synthesis of vitamin A intermediate. The C5 aldehyde intermediate is produced from butadiene via catalytic oxidative acetoxylation followed by rhodium-catalyzed hydroformylation (see Fig. 2.30). Two variations on this theme have been described. In the Hoffmann-La-Roche process a mixture of butadiene, acetic acid and air is passed over a palladium/tellurium catalyst. The product is a mixture of cis- and truns-1,4diacetoxy-2-butene. The latter is then subjected to hydroformylation with a conventional catalyst, Rh.H(CO)(Ph$)~, that has been pretreated with sodium borohydride. When the aldehyde product is heated with a catalytic amount of p-toluenesulphonic acid, acetic acid is eliminated to form an unsaturated aldehyde. Treatment with a palladium-on-charcoal catalyst causes the double bond to isomerize, forming the desired C5-aldehyde intermediate. In the BASF process the 1,2-diacetate is the substrate for the hydroformylation step. It can be prepared either directly via oxidative acetoxylation of butadiene using a selenium catalyst or via PtCb-catalyzed isomerization of the 1,4-diacetate (see above). The latter reaction affords the 1,Zdiacetate in 95% yield. The hydroformylation step is carried out with a rhodium catalyst without phosphine ligands since the branched aldehyde is the desired product (phosphine ligands promote the forma- tion of linear aldehydes). Relatively high pressures and temperatures are used and the desired branched aldehyde predominates. The product mixture is then treated with sodium acetate in acetic acid to effect selective elimination of acetic acid from the branched aldehyde, giving the desired C5 aldehyde.
66 2 - CATALYTIC PROCESSES IN INDUSTRY 2.15 IBUPROFEN Feedstock p-Isobutylbenzene (see Fig. 2.31). IBUPROFEN I COlPd Fig. 2.31. Two routes for the production of ibuprofen.
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Studies in Surface Science and Cata
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Studies in Surface Science and Cata
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Preface Catalysis is a fascinating
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industrial context of the features
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Contents Preface ..................
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4.3.4 P-Elimination and Deinsertion
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7.4.1 Scope .......................
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12.3 Adsorption Isotherms .........
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List of contributors E.B.M. Doesbur
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Introductory section
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Chapter 1 History of catalysis 1.1
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1 -HISTORY OF CATALYSIS 5 One of th
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1 - HISTORY OF CATALYSIS 7 was disc
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1 -HISTORY OF CATALYSIS exlenaed em
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1 -HISTORY OF CATALYSIS 11 aromatiz
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1 -HISTORY OF CATALYSIS 13 had a gr
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4 - BONDING AND ELEMENTARY STEPS IN
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Chapter 5 Heterogeneous catalysis 5
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5 -HETEROGENEOUS CATALYSIS 161 a. _
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5 -HETEROGENEOUS CATALYSIS 163 appr
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5 -HETEROGENEOUS CATALYSIS 165 In r
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5 - HETEROGENEOUS CATALYSIS 167 lit
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5 - HETEROGENEOUS CATALYSIS 169 An
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5 -HETEROGENEOUS CATALYSIS 171 A ma
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5 - HETEROGENEOUS CATALYSIS 173 2 L
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5 - HETEROGENEOUS CATALYSIS 175 (3)
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5 -HETEROGENEOUS CATALYSIS 177 20 '
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5 -HETEROGENEOUS CATALYSIS 179 with
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5 - HETEROGENEOUS CATALYSIS 181 In
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5 -HETEROGENEOUS CATALYSIS 183 Info
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5 -HETEROGENEOUS CATALYSIS 185 0 20
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5 - HETEROGENEOUS CATALYSIS 187 TAB
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5 -HETEROGENEOUS CATALYSIS 189 i)U
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5 -HETEROGENEOUS CATALYSIS 600 560
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5 -HETEROGENEOUS CATALYSIS 193 b H
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Chapter 6 Homogeneous catalysis wit
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6 -HOMOGENEOUS CATALYSIS WlTH TRANS
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6 - HOMOGENEOUS CATALYSIS WlTH TRAN
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6 -HOMOGENEOUS CATALYSIS WITH TRANS
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6 - HOMOGENEOUS CATALYSIS WlTH TRAN
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6 - HOMOGENEOUS CATALYSIS WITH TRAN
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6 -HOMOGENEOUS CATALYSIS WTH TRANSI
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Applied catalysis
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Chapter 7 Catalytic reaction engine
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7 -CATALYTIC REACTION ENGINEERING 2
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7 - CATALYTIC REACTION ENGINEERING
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7 -CATALYTIC REACTION ENGINEERING I
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Ca ta I ys t preparation
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Chapter 8 Preparation of catalyst s
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8 - PREPARATION OF CATALYST SUPPORT
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8 -PREPARATION OF CATALYST SUPPORTS
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Chapter 9 Preparation of supported
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PREPARATION OF SUPPORTED CATALYSTS
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Catalyst characterization
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Chapter 10 Ca ta I yst characteriza
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10 -CATALYST CHARACTERIZATION WITH
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I0 -CATALYST CHARACTERJZATION WITH
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Chapter 11 Temperature programmed r
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11 -TEMPERATURE PROGRAMMED REDUCTIO
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Chapter 12 The use of adsorption me
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12 -ADSORPTION METHODS 421 pairs of
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12 -ADSORPTION METHODS 423 of multi
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12 -ADSORPTION METHODS 425 son of t
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12 - ADSORPnON METHODS 427 equation
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12 - ADSOWON METHODS / Fig. 12.4. T
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12 - ADSOFSTION METHODS 431 - a i-
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12 -ADSORPTION METHODS 433 uptake o
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12 - ADSOlU'TION METHODS 435 gives
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12 - ADSOFSTION METHODS 437 condens
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Future trends
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Chapter 13 Future trends The large
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13 - FUTURE TRENDS 443 control of t
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13 -FUTURE TRENDS 445 the conversio
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Subject Index x-Acceptor Iigands, 2
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SUBJECT INDEX 449 - see also Extend
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SUBJECr INDEX 451 Ethane, 143 Ethen
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SUBJECT INDEX 453 Hydrogen peroxide
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SDJJTT INDEX 455 Octane number, 24,
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SUBJECT INDEX 457 RBS, 383 Reaction
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SUBJECT INDEX 459 - see also Ruther
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STUDIES IN SURFACE SCIENCE AND CATA
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Volume 35 Volume 36 Volume 37 Volum
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Volume 70 Volume 71 Volume 72 Volum
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