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Lindlar Catalyst




The catalyst is prepared by reduction of Palladium Chloride in the presence of a slurry of calcium carbonate followed by adding Lead Acetate . By grafting palladium in this way to a solid substrate a large catalytically active surface area is obtained. The Lindlar catalyst is effective with Hydrogen in the Organic Reduction of Alkyne s to Alkene s. Deactivation of the catalyst with Quinoline makes the catalyst very selective and the hydrogenation is not carried through to the Alkane . Alkyne reduction is Stereoselective with Syn Addition to the Cis-alkene . The reason for this is that one face of the triple bond is shielded by the catalyst surface restricting access for the hydrogen molecule to the other side. An example of alkyne reduction is the reduction of phenylacetylene to Styrene . The commercial Organic Synthesis of Vitamin A also involves an alkyne reduction with the Lindlar catalyst.

Other heterogeneous hydrogenation catalysts are Adam's Catalyst , Palladium Black and Raney Nickel .
Homogeneous catalysts include Wilkinson's Catalyst .


EXTERNAL LINKS

  • http://ptcl.chem.ox.ac.uk/MSDS/PA/palladium(poisoned).html



REFERENCES

  • Lindlar, H.; ''Helv. Chim. Acta'' 1952, ''35'', 446.

  • ''Palladium catalyst for the partial reduction of acetylenes'' H. Lindlar and R. Dubuis Organic Syntheses , Coll. Vol. 5, p.880; Vol. 46, p.89 Article