Lindlar catalyst is commercially available but can also be created by reducing palladium chloride in a slurry of calcium carbonate (CaCO3) and adding lead acetate.[1][2] A variety of other "catalyst poisons" have been used, including lead oxide and quinoline.[3] 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.
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.[5]
See also
Rosenmund reduction, a reduction using palladium on barium sulfate, poisoned with sulfur compounds.
Urushibara Nickel, a nickel based catalyst used to hydrogenate alkynes to alkenes.
^Lindlar, H. (1 February 1952). "Ein neuer Katalysator fur selektive Hydrierungen". Helvetica Chimica Acta. 35 (2): 446–450. doi:10.1002/hlca.19520350205.
^Davister, Michèle; Laszlo, Pierre (1993). "Explanation of a paradoxical selectivity in Friedel-Crafts alkylation under heterogeneous catalysis". Tetrahedron Letters. 34 (3). Great Britain: Pergamon Press: 535.