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Mass spectrometric screening of catalysts

A technology of catalyst and catalytic reaction, which is used in mass spectrometer, library screening, chemical analysis using catalysis, etc., and can solve problems such as being unsuitable for high-throughput screening.

Inactive Publication Date: 2002-03-13
苏黎世公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Common methods used to evaluate these properties of polymers, such as size exclusion chromatography (also known as gel permeation chromatography or gpc), light scattering, viscometry, or colligative measurements, all require large samples and / or careful Calibration, and neither is suitable for high-throughput screening

Method used

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  • Mass spectrometric screening of catalysts
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Examples

Experimental program
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Embodiment Embodiment 1

[0048] Examples Example 1: Screen a small group of Brookhart Pd(II) complexes, these complexes have different aryl groups on the diimine ligand 1aR=CH 3 ; R′=H; R″=H1bR=CH 3 : R′=CH 3 ; R″=H1cR=CH 3 ; R′=CH(CH 3 ) 2 ; R″=H

[0049] The screening process was carried out in accordance with the reaction in Table 1. The solution is composed of complexes 1a, 1b and 1c (see Table 1), where each substance is in CH 2 Cl 2 Is approximately 10 -3 M, the solution was saturated with ethylene and reacted at -30°C for 1 hour, then quenched with dimethyl sulfoxide (DMSO), and finally diluted 100 times. The solution was immediately electrosprayed in the Finnigan MAT TSQ-7000 tandem mass spectrometer, and the operation of the mass spectrometer was carried out as described previously (Hinderling, C. et al. (1997) Angew. Chem. 109: 272; Hinderling, C .et al. (1997) J. Am. Chem. Soc. 119: 10793; Feichtinger, D. and Plattner, DA (1997) Angew. Chem. 109: 1796; Feichtinger, D. et al...

Embodiment 2

[0049] The screening process was carried out in accordance with the reaction in Table 1. The solution is composed of complexes 1a, 1b and 1c (see Table 1), where each substance is in CH 2 Cl 2 Is approximately 10 -3 M, the solution was saturated with ethylene and reacted at -30°C for 1 hour, then quenched with dimethyl sulfoxide (DMSO), and finally diluted 100 times. The solution was immediately electrosprayed in the Finnigan MAT TSQ-7000 tandem mass spectrometer, and the operation of the mass spectrometer was carried out as described previously (Hinderling, C. et al. (1997) Angew. Chem. 109: 272; Hinderling, C .et al. (1997) J. Am. Chem. Soc. 119: 10793; Feichtinger, D. and Plattner, DA (1997) Angew. Chem. 109: 1796; Feichtinger, D. et al.. (1998) J Am. Chem. Soc. 120: 7175; Hinderling, C. et al. (1998) Angew. Chem. 110: 2831). The electrospray mass spectrum recorded by scanning the first quadrupole in Figure 1A is complex and shows a series of oligomer and polymer ions correspon...

Embodiment 3

[0053] in Figure 3A It clearly shows that corresponding to ion 4c, the mass peak at m / z=511 is dominant, and ion 4c is formed by collision-induced β-hydride removal of the hydrocarbon chain on the ion formed by catalyst 1c. The small "sharp" peak at m / z=405 corresponds to the secondary fragmentation product of the diimine ligand without palladium. By scanning the precursor ion on the mass of 4 and the secondary fragment, it can be seen that the secondary fragment [4-Pd] (or [4e-Pd-Br]) is clearly connected to the original ion 4. This result clearly shows that among the eight possible catalysts 1a-h, complex 1c is the best actual polymerization catalyst, which is inconsistent with previous reports. [1] Is consistent. Similarly, the product ion mass spectrum with lower mass cutoff mass (Figure 3B) shows that the second best catalysts are 1b, 1d, and 1e. The consistency of mass spectrometry and traditional detection methods proves the effectiveness of the catalyst screening method of...

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Abstract

Screening methods to identify catalysts or to identify improved catalysts using mass spectrometric analysis of products of catalysis, particularly catalyst-bound intermediate products in the catalytic cycle. The methods are applicable, in particular, to screening of organometallic compounds for catalytic function. Moreover, the methods are applicable, in particular, to screening for catalysts for polymerization reactions. More specifically, the methods employ a two stage (or two step) mass spectrometric detection method in which ions formed in a first stage ionization and which are linked to catalyst performance are selected and the catalyst associated with the selected ion is identified in a second stage employing tandem mass spectrometry. In specific embodiments, the screening methods of this invention avoid explicit encoding because the identity of the catalyst is implicitly contained in the product molecular mass (typically an intermediate product), since the catalyst (or a portion thereof) remains attached to the product.

Description

Background of the invention [0001] This application describes a rapid screening method using mass spectrometry to identify compounds with catalytic activity. Examples show that this method uses tandem mass spectrometry and gas phase ion-molecule reactions to rapidly screen polymerization catalysts, and can be specifically used to screen organometallic catalysts used in polyolefin production. The advantages of the screening method of the present invention are high sensitivity (on the order of milligrams), short detection time (1 hour), and direct and competitive screening of multiple types at the same time according to high polymer formation tendency (rather than derivative properties such as exotherm). Catalysts, good prospects for scaling up into large-scale combinatorial groups, and implicitly encoding catalyst identities by quality. Simple ion-molecule reactions are used to simplify the mass spectrum of complex mixtures produced during the screening process. [0002] People hav...

Claims

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Application Information

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IPC IPC(8): C07B61/00C40B30/08C40B40/18G01N31/10H01J49/42
CPCC40B30/08B01J2219/00738C40B40/18B01J2219/00707G01N31/10B01J2219/00747B01J2219/00745H01J49/00
Inventor P·陈C·希德林
Owner 苏黎世公司
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