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Catalyst compositions comprising a grubbs-hoveyda type complex and a terminal olefin and their use for hydrogenation of nitrile rubber

A technology of catalysts and compositions, applied in organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, chemical instruments and methods, etc., can solve the problem of uncontrolled use of catalysts, low hydrogenation catalysts, etc. problem, to achieve the effect of high hydrogenation activity and high degree of hydrogenation

Active Publication Date: 2014-09-03
ARLANXEO DEUT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0065] (3) Catalysts having both, i.e., catalytic activity for both metathesis and hydrogenation cannot be used in a controlled manner
[0067] However, to date no literature reports the preparation of HNBR with controlled molecular weight and thus Mooney viscosity using only a catalyst based on ruthenium or osmium, which is otherwise known for its metathesis activity
Also, to date there is no hydrogenation catalyst that can be used in NBR hydrogenation to high conversion at very low concentrations

Method used

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  • Catalyst compositions comprising a grubbs-hoveyda type complex and a terminal olefin and their use for hydrogenation of nitrile rubber
  • Catalyst compositions comprising a grubbs-hoveyda type complex and a terminal olefin and their use for hydrogenation of nitrile rubber
  • Catalyst compositions comprising a grubbs-hoveyda type complex and a terminal olefin and their use for hydrogenation of nitrile rubber

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0593] The preparation of the novel catalyst compositions can be carried out in suitable solvents which do not deactivate the catalysts used and which do not adversely affect the hydrogenation in any other way. Preferred solvents include, but are not limited to, dichloromethane, benzene, toluene, methyl ethyl ketone, acetone, tetrahydrofuran, tetrahydropyran, dioxane, cyclohexane, and chlorobenzene. Particularly preferred solvents are chlorobenzene and methyl ethyl ketone.

[0594] Formation of the novel catalyst composition takes place prior to introducing hydrogen into the reaction system.

[0595] Step b) of the method of the invention:

[0596] The hydrogenation of nitrile rubber can be carried out by bringing the nitrile rubber into contact with the catalyst composition formed in step a) of the process according to the invention in the presence of hydrogen.

[0597] The hydrogenation is preferably at a temperature ranging from 60°C to 200°C, preferably from 80°C to 180°...

example

[0678] Catalysts used in the examples:

[0679] Catalysts (1) and (2) were purchased from Sigma Aldrich or Strem Chemicals Inc. Catalyst (3) was purchased from Xian Kaili Co. (China). The structures of these catalysts are shown below, where "Mes" refers to mesityl (2,4,6-trimethylphenyl) and "Cy" refers to cyclohexyl:

[0680]

[0681] These catalysts have the following molecular weights:

[0682] catalyst

molecular weight

[g / mol]

(1)

626.62

(2)

733.75

(3)

925.22

[0683] Nitrile rubber used in the examples:

[0684] The nitrile rubber used in the examples is commercially available from LANXESS Germany GmbH and has properties as outlined in Table 1.

[0685] Table 1: Nitrile rubber (NBR) used

[0686]

[0687] *A terpolymer with one carboxylic acid trimer, trimer content: 1% by weight

[0688] Vinyl ethyl ether (VEE) was purchased from Sigma-Aldrich.

[0689] analysis test:

[0690] GPC test: the...

example 1

[0702] Example 1: (comparative example, using catalyst (3))

[0703] 18g 3431VP at 282g MCB ( The solution in 3431VP at a concentration of 6 wt%) was bubbled with nitrogen for 30 minutes in a 600 mL Parr autoclave and then heated to 120°C. Will Wilkinson catalyst (15mg) and PPh 3 (18 mg) was dissolved into another 22 g of degassed MCB and then added to the reactor. The hydrogenation was carried out at a hydrogen pressure of 4.137 MPa and a stirring speed of 800 rpm. Samples were taken from the reactor at intervals for FT-IR analysis to determine the degree of hydrogenation. After 5 hours of hydrogenation, the degree of hydrogenation reached 90.3%, the reactor was cooled to room temperature and the pressure was released. Final molecular weight and PDI are: Mn = 76,286, Mw = 260,572, PDI = 3.42.

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Abstract

This invention relates to novel Ruthenium- or Osmium-based complex catalysts based on Grubbs-Hoveyda, Grela or Zhan IB, and a catalyst composition comprising at least one vinyl group, preferably a specific promoter of ethyl vinyl ether, and to a process for selectively hydrogenating nitrile rubbers in the presence of such novel catalyst compositions. The process preferably comprises a metathesis step, wherein a complex catalyst used in the metathesis step is same with that used in the hydrogenating step.

Description

technical field [0001] The present invention relates to a novel catalyst composition based on a complex catalyst based on ruthenium or osmium having metathesis activity in a certain molar ratio and a specific cocatalyst and to a method for selectively Process for hydrogenating nitrile rubber. Background technique [0002] The term "acrylonitrile-butadiene rubber" or "nitrile rubber", also referred to as "NBR" for brevity, is to be interpreted broadly and refers to at least one α,β-unsaturated nitrile, at least one Rubbers of copolymers or terpolymers of a conjugated diene and, if desired, one or more additional copolymerizable monomers. [0003] Hydrogenated NBR, also referred to simply as "HNBR", is commercially produced by hydrogenating NBR. Therefore, the selective hydrogenation of carbon-carbon double bonds in diene-based polymers must be carried out without affecting the nitrile groups and other functional groups (such as carboxyl groups) in these polymer chains when ...

Claims

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Application Information

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IPC IPC(8): B01J31/22B01J31/02C08C19/02
Inventor 维尔纳·奥布雷赫特萨拉·戴维柳庆春魏真理
Owner ARLANXEO DEUT GMBH
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