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A kind of isomerization and hydroformylation reaction method and catalyst of internal olefin

A catalyst and isomerization technology, applied in the direction of organic compound/hydride/coordination complex catalyst, carbon monoxide reaction preparation, physical/chemical process catalyst, etc. The effect of low n-iso and high n-aldehyde and iso-aldehyde ratio and high conversion rate

Active Publication Date: 2019-10-11
广东欧凯新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] Aiming at the defect of low positive-to-isotropic ratio of aldehyde products in the existing internal olefin hydroformylation catalytic system, the technical problem to be solved by the present invention is to provide a catalyst and internal olefin combined with a rhodium-ruthenium bimetallic and tridentate phosphorus ligand. Hydroformylation method

Method used

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  • A kind of isomerization and hydroformylation reaction method and catalyst of internal olefin
  • A kind of isomerization and hydroformylation reaction method and catalyst of internal olefin
  • A kind of isomerization and hydroformylation reaction method and catalyst of internal olefin

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Effect test

Embodiment 1

[0033] Embodiment 1: adopt rhodium acetylacetonate dicarbonyl (Rh(acac)(CO) 2 ) and 2,2,6-tris(diphenylphosphinemethyl)-1,1’-biphenyl (Tribi) hydroformylation (different phosphorus-rhodium ratio L / Rh)

[0034] The rhodium catalyst Rh(acac)(CO) was weighed in the glove box according to the different molar ratios of phosphorus ligand to rhodium listed in Table 1 below. 2 (2.6mg, 0.01mmol), 2,2,6-tris(diphenylphosphinemethyl)-1,1'-biphenyl (Tribi) (7.5mg, 0.01mmol; 15mg, 0.02mmol; 22mg, 0.03mmol ; 30mg, 0.04mmol; 45mg, 0.06mmol) into the complexing bottle, then put the toluene (Toluene, 1.73g, 18.8mmol) solvent of deoxygenation / water into the bottle, stir to make it dissolve to form rhodium and biphenyl triphenyl Complex solutions of phosphorus ligands. Put the autoclave into the glove box, pipette 200 μl of the complexed rhodium catalyst solution into the reaction bottle (5ml) with a magnet, add 100 μl of internal standard n-decane and 400 μl of toluene solvent , and finally ...

Embodiment 2

[0039] Embodiment 2: adopt rhodium acetylacetonate dicarbonyl (Rh(acac)(CO) 2 ) and 2,2,6-tris(diphenylphosphinomethyl)-1,1’-biphenyl (Tribi) hydroformylation (different reaction temperatures)

[0040] The rhodium catalyst Rh(acac)(CO) was weighed in a glove box according to the molar ratio of phosphorus ligand to rhodium (4:1) listed in Table 2 below. 2 (2.6mg, 0.01mmol), 2,2,6-tris(diphenylphosphinemethyl)-1,1'-biphenyl (Tribi) (30mg, 0.04mmol) into the complexation bottle, and then deoxygenated / water toluene (Toluene, 1.73g, 18.8mmol) solvent was placed in the bottle, and stirred to dissolve it to form a complex solution of rhodium and biphenyl triphosphorus ligand. Put the autoclave into the glove box, pipette 200 μl of the complexed rhodium catalyst solution into the reaction bottle (5ml) with a magnet, add 100 μl of internal standard n-decane and 400 μl of toluene solvent , and finally 2-octene (cis-trans mixture) (224.4 mg, 2 mmol) was added. Subsequently, the react...

Embodiment 3

[0044] Embodiment 3: adopt rhodium acetylacetonate dicarbonyl (Rh(acac)(CO) 2 ) and 2,2,6-tris(diphenylphosphinomethyl)-1,1'-biphenyl (Tribi) hydroformylation reaction (different reaction pressure, S / C=2000, S / C is the reaction molar ratio of catalyst to catalyst)

[0045] According to example 2, the rhodium catalyst complex solution of the same concentration is prepared in the glove box, the autoclave is put into the glove box, and the rhodium catalyst solution that 200 μ l is complexed is pipetted to the reaction that the magneton is placed In the bottle (5ml), add 100μl internal standard n-decane and 400μl toluene solvent, and finally add 2-octene (cis-trans mixture) (224.4mg, 2mmol). Subsequently, the reaction kettle with the reaction bottle was taken out from the glove box, and was washed with H 2 Replace the high-purity argon in the kettle 3 times with CO / H 2Raise the total pressure of the reactor to 4 bar, 5 bar, 10 bar, 20 bar and 40 bar at a pressure ratio of 1:1, ...

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Abstract

A reaction method and catalyst for long-chain internal olefin isomerization and hydroformylation, adopting two metal complexes of rhodium and ruthenium as catalysts, and further adopting a tridentate phosphorus ligand. The catalytic system can perform a homogeneous internal olefin isomerization and hydroformylation reaction under a certain temperature and pressure to obtain an aldehyde product with a high normal-to-iso ratio. The method is suitable for a long-chain internal olefin (>C8), and is also suitable for an internal olefin with less than 8 carbons.

Description

technical field [0001] The invention relates to a reaction method and catalyst for isomerization and hydroformylation of internal olefins, in particular to a catalytic system combining a rhodium-ruthenium double metal complex and a biphenyl triphosphorus ligand, which is used in a homogeneous reaction system Isomerization and hydroformylation of long-chain internal olefins. Background technique [0002] The hydroformylation reaction of alkenes with carbon monoxide and hydrogen produces aldehyde compounds, which are not only used as chemicals such as fragrances, but also important intermediates. The obtained aldehydes can be further hydrogenated, oxidized and aminated to be converted into compounds such as alcohols, carboxylic acids and amines, which are used in bulk chemicals, plasticizers, coatings and other optical materials. Hydroformylation technology, also known as "oxo synthesis method", has been accidentally discovered by Professor Otten Roelen in 1938 (Chem. After ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/24B01J31/30C07C45/50C07C47/02
Inventor 张绪穆张润通陈震陈才友
Owner 广东欧凯新材料有限公司
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