Combinatorial discovery of metal co-catalysts for the carbonylation of phenol

Abstract The palladium-catalyzed carbonylation of phenol to form diphenyl carbonate (DPC) requires the presence of a metal co-catalyst to catalyze the reoxidation of palladium from Pd 0 to Pd 2+ in the presence of oxygen. In this study, we utilize a high throughput screening (HTS) methodology to rapidly study the nature of the co-catalyst with an emphasis on combinations of metal co-catalysts that appear to work in a synergistic manner to increase palladium usage. Critical new developments were made in using a small-scale reactor in diffusion controlled systems. The HTS system is described along with the optimized catalyst packages that were determined. Additionally, the results from HTS were used to better elucidate the mechanism of this potentially important commercial reaction.

[1]  J. Hanak,et al.  Calculation of composition of dilute cosputtered multicomponent films , 1973 .

[2]  A. Lapidus,et al.  Oxidative carbonylation of phenol , 1999 .

[3]  J. E. Hallgren,et al.  The Reactions of Carbon Monoxide and Phenols Promoted by Palladium Complexes , 1979 .

[4]  J. Gittleman,et al.  THE EFFECT OF GRAIN SIZE ON THE SUPERCONDUCTING TRANSITION TEMPERATURE OF THE TRANSITION METALS. , 1969 .

[5]  J. J. Hanak Monolithic solar cell panel of amorphous silicon , 1979 .

[6]  A. Vavasori,et al.  Multistep electron transfer catalytic system for the oxidative carbonylation of phenol to diphenyl carbonate , 1999 .

[7]  J. Baeckvall Palladium in some selective oxidation reactions , 1983 .

[8]  J N Cawse,et al.  Experimental strategies for combinatorial and high-throughput materials development. , 2001, Accounts of chemical research.

[9]  A. Battersby,et al.  Oxidative coupling of phenols , 1967 .

[10]  B. Abeles,et al.  SUPERCONDUCTING AND SEMICONDUCTING PHASES OF GRANULAR FILMS. , 1971 .

[11]  L. Hubert-Pfalzgraf,et al.  Synthesis, structural principles and reactivity of heterometallic alkoxides , 1990 .

[12]  J. Hanak Compositional Determination of rf Co-Sputtered Multicomponent Systems , 1971 .

[13]  Wolfgang A. Herrmann,et al.  High-Throughput-Katalysatorscreening unter Hochdruckbedingungen , 2001 .

[14]  S. Caddick Palladium reagents and catalysts: Innovation on Organic synthesis , 1997 .

[15]  Ferdi Schüth,et al.  The development of a high throughput reactor for the catalytic screening of three phase reactions , 2001 .

[16]  J. E. Hallgren,et al.  The palladium-catalyzed synthesis of diphenyl carbonate from phenol, carbon monoxide, and oxygen , 1981 .

[17]  J. Gittleman,et al.  Radio‐Frequency‐Sputtered Films of β‐Tungsten Structure Compounds , 1970 .

[18]  T. Kitamura,et al.  A new and efficient catalytic system for synthesis of diphenyl carbonate with W–Mo-heteropolyacids as a cocatalyst , 2000 .

[19]  J. Gittleman,et al.  The effect of grain size on the superconducting transition temperature of transition metals , 1971 .

[20]  J. E. Hallgren,et al.  The palladium-catalyzed synthesis of diphenyl carbonate from phenol, carbon monoxide, and oxygen : II. Aqueous sodium hydroxide as a base , 1981 .

[21]  Combinatorial Libraries: Studies in Molecular Recognition and the Quest for New Catalysts , 1997 .

[22]  Eric J. Amis,et al.  Combinatorial Materials Science: What’s New Since Edison? , 2002 .

[23]  J. Cargill,et al.  Automated combinatorial chemistry on solid phase , 1996 .

[24]  James Norman Cawse,et al.  Experimental Design for Combinatorial and High Throughput Materials Development , 2002 .

[25]  T. Kitamura,et al.  A new efficient Pd-catalyzed synthesis of diphenyl carbonate with heteropolyacid as a cocatalyst , 2001 .

[26]  R. Wehner,et al.  Calculation of Deposition Profiles and Compositional Analysis of Cosputtered Films , 1972 .

[27]  M. Goyal,et al.  Direct synthesis of diphenyl carbonate by oxidative carbonylation of phenol using Pd–Cu based redox catalyst system , 1999 .

[28]  J. Hanak The “multiple-sample concept” in materials research: Synthesis, compositional analysis and testing of entire multicomponent systems , 1970 .

[29]  Kevin Burgess,et al.  New Catalysts and Conditions for a CH Insertion Reaction Identified by High Throughput Catalyst Screening , 1996 .

[30]  P. Schultz,et al.  A Class of Cobalt Oxide Magnetoresistance Materials Discovered with Combinatorial Synthesis , 1995, Science.