Lindlar catalyst

Lindlar catalyst

Chembox new
Name = Lindlar catalyst
ImageFile = Lindlar_eng.png ImageName =
OtherNames = Palladium on calcium carbonate, poisoned
Section1 = Chembox Identifiers
CASNo = 7440-05-3
RTECS =
Section2 = Chembox Properties
Formula = not a compound
Appearance = Gray powder
Section7 = Chembox Hazards
ExternalMSDS = [http://ptcl.chem.ox.ac.uk/MSDS/PA/palladium(poisoned).html External MSDS]
MainHazards = none
RPhrases = R20 R33 R36 R37 R38
SPhrases = S22 S27 S36 S37 S39
Section8 = Chembox Related
OtherCpds = Palladium on carbon

A Lindlar catalyst is a heterogeneous catalyst that consists of palladium deposited on calcium carbonate and treated with various forms of lead. The lead additive serves to deactivate the palladium sites. A variety of "catalyst poisons" have been used including lead acetate and lead oxide. The palladium content of the catalyst is usually 5% by weight. The catalyst is used for the hydrogenation of alkynes to alkenes.

As described by its inventor,Lindlar, H.; Dubuis, R. "Palladium Catalyst for Partial Reduction of Acetylenes" Organic Syntheses, Collected Volume 5, p.880 (1973).http://www.orgsyn.org/orgsyn/pdfs/CV5P0880.pdf] [Lindlar, H."Ein neuer Katalysator für selektive Hydrierungen"; "Helv. Chim. Acta" 1952, "35", 446-450, DOI|10.1002/hlca.19520350205.] the catalyst is prepared by reduction of palladium chloride in a slurry of calcium carbonate followed by adding lead acetate. By this approach, one obtains a catalyst with a large surface area. Further deactivation of the catalyst with quinoline enhances its selectivity, preventing formation of alkanes. An example of alkyne reduction is the reduction of phenylacetylene to styrene.

Alkyne reduction is stereoselective, occurring via syn addition to give the cis-alkene. [ Overman, L. E.; Brown, M. J.; McCann, S. F. "(Z)-4-(Trimethylsilyl)-3-Buten-1-ol" Organic Syntheses, Collected Volume 8, p.609 (1993). http://www.orgsyn.org/orgsyn/pdfs/CV8P0609.pdf] The commercial organic synthesis of vitamin A also involves an alkyne reduction with the Lindlar catalyst.

Other heterogeneous catalysts useful for hydrogenation are Adam's Catalyst, Palladium Black, and Raney nickel.

References


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