Friday, May 17, 2019

organic chemistry - Difference between Lindlar and Rosenmund catalysts


Is there any difference between the Lindlar and Rosenmund catalysts? I've checked around, and it seems the same compounds are used to make both. Is there a difference in their reactivities or are they essentially the same?



Answer



This is a rather interesting question because these names actually refer to classes of reactions (specific to certain reagents and products), and aren't constrained by specific proportions of substances or even the identity of these substances.


$\hspace{4cm}$enter image description here


A Rosenmund catalyst is used to reduce acyl chlorides to their corresponding aldehydes, and is typically composed of palladium supported on $\ce{BaSO4}$, and poisoned by sodium acetate, N,N-dimethylaniline, thiourea, thiophene, dibenzothiophene, ethyldiisopropyl amine, or, most commonly, quinoline.


A Lindlar catalyst is used to reduce alkynes to cis alkenes, and is typically composed of palladium supported on $\ce{BaCO3}$, $\ce{CaCO3}$, or carbon, and poisoned by lead acetate and quinoline.


The broad list of poisons which cause nearly identical catalytic activity of the supported palladium in both Lindlar and Rosenmund catalysts tells that the poisons are not involved in the catalytic process itself, but rather are affecting the surface of the catalyst. Interestingly, Lindlar-active palladium shows no activity for the conversion of benzoyl chloride to benzaldehyde under various conditions. This demonstrates that despite similar catalyst preparation procedures, the two reactions are catalyzed by different active sites.$^{[1]}$





$[1]$ Mcewen, A. B.; Guttieri, M. J.; Maier, W. F.; Laine, R. M.; Shvo, Y. The Journal of Organic Chemistry 1983, 48 (23), 4436–4438.


No comments:

Post a Comment

digital communications - Understanding the Matched Filter

I have a question about matched filtering. Does the matched filter maximise the SNR at the moment of decision only? As far as I understand, ...