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Ruthenium- or osmium-based complex catalysts

A complex and alkyl technology, applied in physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, organic chemistry, etc., can solve problems such as no Ru or Os-alkylene structure

Active Publication Date: 2016-03-09
ARLANXEO DEUT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0045] This object has now been solved by providing novel ruthenium-based or osmium-based complex catalysts comprising a Schiff base-type ligand on the one hand and an N-heterocyclic carbene ("NHC") ligand on the other hand. body, but no Ru or Os-alkylene structure

Method used

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  • Ruthenium- or osmium-based complex catalysts
  • Ruthenium- or osmium-based complex catalysts
  • Ruthenium- or osmium-based complex catalysts

Examples

Experimental program
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example

[0403] abbreviation:

[0404] phr per 100 rubber (weight)

[0405] rpm revolutions per minute

[0406] HD degree of hydrogenation

[0407] Mn number average molecular weight

[0408] Mw weight average molecular weight

[0409] PDI polydispersity index, defined as Mw / Mn

[0410] PPh 3 Triphenylphosphine

[0411] MCB monochlorobenzene

[0412] Rt. room temperature(22+ / -2℃)

[0413] RDB residual double bonds, in %, RDB = (1 - degree of hydrogenation) * 100%, where NBR has 100% RDB

[0414] NHCN-heterocycle-carbene

[0415] Cycyclohexyl

[0416] IMesN,N'-bis(trimethylphenyl)imidazol-2-ylidene

[0417] SIMesN,N'-bis(trimethylphenyl)imidazolidin-2-ylidene, also known as H2-Imes

[0418] IPrN,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene

[0419] ItBuN,N'-bis(tert-butyl)imidazol-2-ylidene

[0420] 1. Catalyst preparation according to route 1

[0421] 1.1 Complex (3a)-PCy 3

[0422]

[0423] From the complex RuHCl(CO)(PCy 3 ) 2Preparation of complex (3a)-...

example 1

[0516] Hydrogenation of 2-pentene

[0517] 15 g of 2-pentene were dissolved in 235 g of MCB in a 600 mL autoclave. The solution was sparged with nitrogen for 20 minutes and heated to 130°C. Complex (Ia)-SIMes was dissolved in 15 mL of degassed MCB and the complex solution was injected into the autoclave. Hydrogen is subsequently introduced into the autoclave up to the desired pressure. After 5 hours of reaction, the degree of hydrogenation reached 99+%.

example 2

[0519] Hydrogenation of 1-Tetradecene

[0520] Charge 300 mL of 1-tetradecene into a 600 mL autoclave. The liquid was sparged with nitrogen for 20 minutes and heated to 130°C. Complex (Ia)-SIMes was dissolved in 15 mL of degassed MCB and the complex solution was injected into the autoclave. Hydrogen is subsequently introduced into the autoclave up to the desired pressure. After 5 hours of reaction, the degree of hydrogenation reached 68%.

[0521] The reaction conditions and results for Examples 1 and 2 are summarized in Table 2.

[0522] Table 2: Example 1 and Example 2

[0523]

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Abstract

The present invention provides novel ruthenium or osmium based complex structures with a unique combination of ligands comprising a Schiff-base type ligand, a N-heterocyclic carbene ligand and a CO ligand which can be prepared according to two different routes involving easily accessible starting materials and which represent excellent catalysts for hydrogenating unsaturated compounds, oligomers and polymers, in particular at unforeseeably low temperatures.

Description

technical field [0001] The present invention relates to ruthenium-based and osmium-based complex structures, their synthesis and their use as catalysts for the hydrogenation of unsaturated compounds. Background technique [0002] Ruthenium-based or osmium-based catalysts have played an important role in the homogeneous hydrogenation of different substrates for many years, as summarized in Handbook of Homogeneous Hydrogenation (HandbookofHomogeneousHydrogenation), 2007, volume 1, pages 45-70 (by DeVries, JohannesG. , Elsevier, edited by CornelisJ). [0003] Ruthenium- and osmium-based complex catalysts containing bidentate Schiff base ligands have been disclosed in WO99 / 26949A1 and Organometallics 1998, 17(16), 3460. Such complex catalysts are reported to be suitable for olefin metathesis. It is further described that these ruthenium- or osmium-based Schiff base complexes are highly stable towards air, moisture and temperature and exhibit catalytic activity even in polar pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00B01J31/22C08C19/02C08L15/00
Inventor 魏真理柳庆春
Owner ARLANXEO DEUT GMBH