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Catalyst compositions 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 low hydrogenation catalysts and uncontrollable use of catalysts, etc. problem, to achieve the effect of high hydrogenation activity

Active Publication Date: 2014-08-06
ARLANXEO DEUT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0064] (3) Catalysts having both, i.e., catalytic activity for both metathesis and hydrogenation cannot be used in a controlled manner
[0066] 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 and their use for hydrogenation of nitrile rubber
  • Catalyst compositions and their use for hydrogenation of nitrile rubber
  • Catalyst compositions and their use for hydrogenation of nitrile rubber

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0410] The preparation of the novel catalyst compositions can be carried out in the presence or absence of a suitable solvent which does not deactivate the catalyst used and which does not adversely affect the hydrogenation in any other way. Preferably, an organic solvent is used to dissolve the complex catalyst. More 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. Typically, a vinyl compound is added to the solution of the complex catalyst.

[0411] Formation of the novel catalyst composition takes place prior to introducing hydrogen into the reaction system.

[0412] Step b) of the method according to the invention:

[0413] Thereafter, the hydrogenation of the nitrile rubber is carried out by contacting the nitrile rubber with hydrogen and the catalyst c...

example

[0494] Catalysts used in the examples:

[0495] Catalysts (1) to (3) were purchased from Sigma Aldrich or Strem Chemicals Inc. Catalyst (4) 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:

[0496]

[0497] These catalysts have the following molecular weights:

[0498] catalyst

molecular weight

[g / mol]

(1)

822.96

(2)

848.97

(3)

885.55

(4)

925.22

[0499] Nitrile rubber used in the examples:

[0500] The nitrile rubber used in these examples had the properties summarized in Table 1.

[0501] Table 1: Nitrile rubber (NBR) used (“CAN” means acrylonitrile)

[0502]

[0503]

[0504] Vinyl ethyl ether (VEE) was purchased from Sigma-Aldrich.

[0505] analysis test:

[0506] GPC test: the apparent molecular weight Mn and Mw are determined by Worcester (Waters) GPC ...

example 1

[0511] Example 1: (comparative example, using catalyst (4))

[0512] 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 catalyst compositions based on Ruthenium- or Osmium-based complex catalysts and specific co-catalysts and to a process for selectively hydrogenating nitrile rubbers in the presence of such catalyst compositions.

Description

technical field [0001] The present invention relates to novel catalyst compositions obtainable from reacting complex catalysts based on ruthenium or osmium with specific cocatalysts and to a process for the selective hydrogenation of nitrile rubber in the presence of such novel catalyst compositions method. 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 polym...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22B01J31/18B01J31/24B01J31/02C08C19/02
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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