Lindlar catalyst

Synthesis

Lindlar catalyst is commercially available but can also be created by reducing palladium chloride in a slurry of calcium carbonate (CaCO3) or barium carbonate (BaCO3) and adding lead acetate. A variety of other "catalyst poisons" have been used, including lead oxide and quinoline. The palladium content of the supported catalyst is usually 5% by weight.

Catalytic properties

The catalyst is used for the hydrogenation of alkynes to alkenes (i.e. without further reduction into alkanes). The lead serves to deactivate the palladium sites, and further deactivation of the catalyst with quinoline or 3,6-dithia-1,8-octanediol enhances its selectivity, preventing formation of alkanes. Thus if a compound contains a double bond as well as a triple bond, only the triple bond is reduced. An example being the reduction of phenylacetylene to styrene.

Alkyne hydrogenation is stereospecific, occurring via syn addition to give the cis-alkene. For example the hydrogenation of acetylenedicarboxylic acid using Lindlar catalyst gives maleic acid rather than fumaric acid.

An example of commercial use is the organic synthesis of vitamin A which involves an alkyne reduction with the Lindlar catalyst. These catalysts are also used in the synthesis of dihydrovitamin K1.

References

References

1. McEwen, Alan B.. (2002-05-01). "Metallic palladium, the actual catalyst in Lindlar and Rosenmund reductions?".
2. (1966). "Palladium Catalyst for Partial Reduction of Acetylenes".
3. (1 February 1952). "Ein neuer Katalysator fur selektive Hydrierungen". Helvetica Chimica Acta.
4. (1993). "Explanation of a paradoxical selectivity in Friedel-Crafts alkylation under heterogeneous catalysis". [[Pergamon Press]].
5. Overman, L. E.. (1993). "(Z)-4-(Trimethylsilyl)-3-Buten-1-ol".
6. Fritz Weber, August Rüttimann "Vitamin K" Ullmann's Encyclopedia Of Industrial Chemistry, 2012, Wiley-VCH, Weinheim. {{doi. 10.1002/14356007.o27_o08