Selective hydrogenation with non-dehalogenation using sulfur modified Pt/C

Sulfur-Modified Pt/C Catalyst for Selective Hydrogenation Without Dehalogenation

Platinum 3% on Carbon (Modified by Sulfur) (Pt/C, TCI code: P3305) is a heterogeneous catalyst with 3 wt% platinum supported on activated carbon and poisoned with sulfur. It is used for chemoselective hydrogenation of nitro groups and olefins, particularly in substrates bearing halogen groups, because dehalogenation is almost completely suppressed.²) The catalyst suits both laboratory and process scale.²) In brochure examples, 2% P3305 under H2 0.2 MPa in MeOH at 30°C for 2 h gave 99.0% product with the halogen retained and only 0.8% dehalogenated byproduct for a halogen-substituted nitroarene. For a bromo nitroarene, 98.6% was retained with 0.7% byproduct after 3 h.²) A chlorinated alkenyl arene gave 99.1% halogen-retained product in 45 min at 0.1 MPa.²) The product is supplied wetted with ca. 50% water because it can be flammable when dried.

Selective hydrogenation with non-dehalogenation using sulfur modified Pt/C
Source: TCI brochure RR208
Reduction of nitro group at low pressure and low temperature with LA type Pd/C
Source: TCI brochure RR208

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References

  1. Broad Survey of Selectivity in the Heterogeneous Hydrogenation of Heterocycles. T. W. Lyons, I. N. Leibler, C. Q. He, S. Gadamsetty, G. J. Estrada, A. G. Doyle, J. Org. Chem. 2024, 89, 1438. doi:10.1021/acs.joc.3c02028
  2. Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success. F. Lovering, J. Bikker, C. Humblet, J. Med. Chem. 2009, 52, 6752. doi:10.1021/jm901241e

Download TCI brochure Precious Metal Catalysts on Activated Carbon for Heterogeneous Selective Hydrogenation (PDF)

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