Download Carbon Monoxide in Organic Synthesis by Jürgen Falbe, Ch.R. Adams PDF

By Jürgen Falbe, Ch.R. Adams

This booklet reports a few vital reactions of carbon monoxide in natural chemistry: hydroformylation, steel carbonyl- and acid catalyzed carbonylation and ring closure reactions with carbon monoxide. it isn't simply a translation of the German variation which seemed in 1967 however the textual content has been thoroughly revised. This was once precious simply because this chemistry is swiftly constructing in examine in addition to in technical software, that is underlined by way of the rise of creation of e. g. oxo chemical substances from approximately 1.4 million lots in 1967 to 2.7 million lots in 1969, approximately a doubling inside of 2 years. a range of of latest examine effects have been released over the past years, and those extra references were brought up within the English variation. many of the new papers stated care for hydroformylation reactions: despite the fact that, some of the papers reviewed additionally record very important new features in carboxylation and ring closure reactions. the writer is indebted to a couple of colleagues who helped to gather those new information and feature given him precious tricks and want to thank pass over 1. Forster, Dr. B. Cornils, Dr. D. Hahn, Dr. P. Schneller, Dr. H. Tummes, and Dr. J. Weber for his or her cooperation, and to Prof. Dr. F. Piacenti (University of Pisa, Italy) for discussions on response mecha­ nisms. the writer is principally thankful to Dr. Charles R. Adams of the Shell improvement corporation, Emeryville, California, for his cooperation in translating the German text.

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The composition of the isomeric products depends greatly on the structure of the starting olefin and the reaction conditions (see chapters 3 and 4). Table 9 gives several examples of products obtained from olefins ofvarious structures. Hydroformylation of Various Structures Table 9. omerizable olefin! 1)-heptane Methyl-(l-naphthyl)-acetaldehyde C I9-Aldehydes 30 91 * Reference [24, 29, 205, 226,1052] [173] [205] 29 54 [24] [24,756] * Rhodium catalyst Hydroformylation of linear terminal olefins under the standard conditions of the technical Oxo process (90-150 °C, 100-300 atm, cobalt catalyst) give linear aldehydes (50-80 %), together with a smaller amount of branched aldehydes.

HaC=CH-CH=CHa + HCo(CO), co ~ H3C-CH=CH-CHa-C-CO(CO)i II o (1) However, as reported by B. Fell and W. Rupilius [1034], dialdehydes can be made from conjugated diolefins using modified rhodium catalysts. 7% tri-n-butylphosphine and obtained 80-90% yields of hydroformylation products which contained 40-45 % of Ca- and C7-dialdehydes respectively. Surprisingly the Co-monoaldehyde fraction contained more than 96% n-valeraldehyde and only 4% of iso-valeraldehyde. -GI CH-CH. -·CH. -CH-CH,-CHO I CHO It may be assumed that dialdehyde formation can be achieved because the isomerisation of the intermediate nonconjugated unsaturated aldehyde to the conjugated aldehyde (which would only give monoaldehyde by hydrogenation) is not catalyzed by the modified rhodium catalyst (see also chapter on reaction mechanism of the hydroformylation reaction, p.

It is obvious that no dialdehyde can be formed from this allenyl compound. It probably reacts with hydrogen to form Hydroformylation of Various Structures 41 Table 13. Hydroformylation of conjugated, acyclic dienes and trimes (Cobalt catalyst) Diene I Pressure (atm) I I Temp. (0C) Products Butadiene 212-282 145-175 2-Methylbutadiene 1-Phenylbutadiene 212-282 3-Methylpentadiene-1,3 2,3-Dimethylbutadiene Cyclopentadiene 2,3-Dimethylbutadiene 2,5-Dimethylhexadiene-2,4 Isoprene dimer 150 212 145-150 260 145-175 353 145-175 200 120 Cycloheptatriene IRef.

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