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Reppe chemistry

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Reppe chemistry refers to a class of carbonylation reactions that are useful in the synthesis of organic compounds. Classic Reppe reactions include hydrocarboxylation and esterification of alkenes, involving the metal-catalysed reaction with carbon monoxide and water or alcohols.

Reactions involving alknes

The hydrocarboxylation of alkenes is a prominent example of Reppe chemistry. In industry, propanoic acid is mainly produced by the hydrocarboxylation of ethylene using nickel carbonyl as the catalyst:

H2C=CH2 + H2O + CO → CH3CH2CO2H

The hydroesterification is similar, but entails the addition of alcohols instead of water, affording esters.

Reactions involving alknes

The high pressure reactions catalysed by heavy metal acetylides, especially copper acetylide, or metal carbonyls are called Reppe Chemistry. Reactions can be classified into various classes. The vinylization according to the equation:

Preparing ethynyldiols from aldehydes according to the equation:

Reactions with carbon monoxide:

This simple synthesis was used to prepare acrylic acid derivatives for the production of acrylic glass.

References

  1. El Ali, B.; Alper, H. "Hydrocarboxylation and hydroesterification reactions catalyzed by transition metal complexes" In Transition Metals for Organic Synthesis, 2nd ed.; Beller, M., Bolm, C., Eds.; Wiley-VCH:Weinheim, 2004. ISBN: 978-3-527-30613-8
  2. W. Bertleff; M. Roeper; X. Sava. "Carbonylation". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_217. ISBN 978-3527306732.{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link)
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