Evaluation of the performance profile of catalysts

Abstract

A searchable library of catalysts, wherein each catalyst is defined by a specific performance profile, is created by a series of steps. The first involves the selection of a catalyst, a substrate and at least two different chemical reactions for catalyst characterization. The next involves contacting the catalyst and substrate under conditions suitable for the selected reaction and measuring for each of the selected reactions a reaction parameter, which is associated with catalyst performance. The catalyst performance is then determined and a value assigned. The performance profile is a table including the performance values. The catalyst is then placed into a library, which is searchable based on the performance profile.

Description

BRIEF DESCRIPTION OF THE SEVERAL VIEWS OF THE DRAWINGS

FIG. 1 a) and b) show an illustration of the concept for catalyst profiling based on a set of sensitive test reactions.

FIG. 2 shows the catalytic performance profiles of four Pd(5-wt %)/C catalysts.

FIG. 3 shows the solids' characteristics profiles.

FIG. 4 shows a series of similarity plots for characterization profiles and for catalytic performance profiles involving DEG-cat 1, DEG-cat 2, DEG-cat 3, and DEG-cat 4.

FIG. 5 shows a reaction scheme which leads to selective formation of saturated alcohol.

FIG. 6 shows performance profiles of real catalysts.

FIG. 7 shows the ideal performance profile.

FIG. 8 shows the ranking of similarity of the sixteen Pd catalysts with respect to the hypothetical ideal profile shown in FIG. 7. Catalyst DEG-3 appears to be the preferable catalyst for the selective hydrogenation of hydroxy-olefin. DEG-16, DEG-14 and DEG-12 are expected to give also high yield of the saturated alcohol.

FIG. 9 shows a plot of the yield of saturated alcohol obtained by conversion of the 1-hydroxy-3,4-olefin versus the similarity values derived from the Euclidean distance between performance profiles of real catalysts and the ideal profile. The correlation is significant. The catalytic performance profiling appears to be a fast and unerring method for pre-selection of catalysts for hydrogenation of multi-functional substrates.

FIG. 10 shows catalyst DEG 5 as having excellent and unique catalytic performance for the selective hydrogenation of multiple C═C double bonds and the selective hydrogenation of Cl-nitro-aromatics. Therefore, it is the preferred catalysts for hydrogenation of multi-functional substrates comprising Cl-substituted nitro-aromatics as well as C═C double bonds.

FIG. 11 shows a catalytic performance profile where similarity to average is plotted against similarity to average rank.

Claims

1. (canceled)

2. (canceled)

3. Method for determining a specific performance profile for a catalyst comprising, a) selecting the catalyst substrate and at least two different chemical reactions for determination from: hydrogenation of carbonyl compoundshydrogenation of olefins or polyolefinshydrogenation of aromatics or heteroaromaticshydrogenation of nitro-compoundshydrogenation of nitrites,hydrogenation of imines,hydrogenation of hydroxylamines,hydrogenation of alkynes,reductive alkylation of primary or secondary amines,reductive amination of aldehydes or ketones by ammonia salts or by amines,hydrogenolysis of C—C bonds, ethers, carbamates, carbonates, amines or organic sulfides,hydrodehalogenation of halo-aromatics or haloaliphatics,dehydrogenation of cycloalkanes or cycloalkenes,isomerization of hydroxy-olefins,hydrogenation of multifunctional substrates having at least two of the following functional groups or structural units: CC-double bond CC-triple bond, nitro-, alcohol-, carbonyl-, carboxyl-, nitril-, imine, hydroxylamine-, azo-, diazo-, halogen-, ether-group or aromatic rings,oxidation of alcohols,oxidation of aldehydes,oxidation of olefins,oxidation of multifunctional substrates having at least two of the following functional groups: CC-double bond, CC-triple bond, alcohol-, carbonyl-, nitril-, imine, hydroxylamine-, azo or diazo-group,C—C coupling,enantioselective hydrogenation of carbonyl compounds,enantioselective reductive alkylation of primary or secondary amines,enantioselective reductive amination of aldehydes or ketones by ammonia salts or by amines,b) contacting the catalyst and substrate under conditions suitable for the selected reaction,c) measuring for each of the selected reactions a reaction parameter associated with catalyst performance,d) estimating and placing the catalyst performance in a table to establish the performance profile.

4. (canceled)

5. (canceled)

6. (canceled)

7. A method for producing a library of catalysts comprising a) selecting the catalyst, substrate and at least two different chemical reactions for determination from:hydrogenation of carbonyl compounds hydrogenation of olefins or polyolefinshydrogenation of aromatics or heteroaromaticshydrogenation of nitro-compoundshydrogenation of nitriles,hydrogenation of imines,hydrogenation of hydroxylamines,hydrogenation of alkynes,reductive alkylation of primary or secondary amines,reductive amination of aldehydes or ketones by ammonia salts or by amines,hydrogenolysis of C—C bonds, ethers, carbamates, carbonates, amines or organic sulfides,hydrodehalogenation of halo-aromatics or haloaliphatics,dehydrogenation of cycloalkanes or cycloalkenes,isomerization of hydroxy-olefins,hydrogenation of multifunctional substrates having at least two of the following functional groups or structural units: CC-double bond CC-triple bond, nitro-, alcohol-, carbonyl-, carboxyl-, nitril-, imine, hydroxylamine-, azo-, diazo-, halogen-, ether-group or aromatic rings,oxidation of alcohols,oxidation of aldehydes,oxidation of olefins,oxidation of multifunctional substrates having including at least two of the following functional groups: CC-double bond, CC-triple bond, alcohol-, carbonyl-, nitril-, imine, hydroxylamine-, azo- or diazo-group,C—C coupling,enantioselective hydrogenation of carbonyl compounds,enantioselective reductive alkylation of primary or secondary amines,enantioselective reductive amination of aldehydes or ketones by ammonia salts or by amines,b) contacting the catalyst and substrate under conditions suitable for the selected reactionc) measuring for each of the selected reactions a reaction parameter associated with catalyst performance,d) estimating and placing the catalyst performance in a table to establish the performance profile.e) placing the catalyst into the library, which is searchable.

8. A method for selecting a catalyst from the library of catalysts where a desired substrate and reaction can result in multiple products and selectivity is desired comprising selecting a catalyst based on a comparison of a desired performance profile for a substrate with a performance profiled of the catalyst of the library.

9. A method according to claim 8 wherein selection involves an algorithm including statistical similarity analysis.

10. The library of catalysts defined by a specific performance profile obtained by the method of claim 7.

11. The library according to claim 10 wherein the catalysts are heterogeneous catalysts.

12. The catalyst defined by a specific performance profile obtained by the method of claim 8.

13. The catalyst according to claim 12 wherein the catalyst is a heterogeneous catalyst.