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Olefin hydroformylation catalyst composition and hydroformylation process

A technology of hydroformylation catalysts and compositions, applied in chemical instruments and methods, physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, etc., can solve the problem that 2-methylbutyraldehyde cannot achieve Intermittent response, etc.

Active Publication Date: 2021-09-14
SHANGHAI HUAYI GRP CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, it was also found that when using tris (2,4-di-tert-butylphenyl) phosphite as a ligand in a batch reaction, the ratio of 2-methylbutyraldehyde in the product can be higher than 60%; but in butene, In the continuous reaction of continuous aeration of syngas, the ratio of 2-methylbutyraldehyde can never achieve the effect of batch reaction

Method used

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  • Olefin hydroformylation catalyst composition and hydroformylation process
  • Olefin hydroformylation catalyst composition and hydroformylation process
  • Olefin hydroformylation catalyst composition and hydroformylation process

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preparation example Construction

[0053] The preparation method of the monodentate complex of the present invention is not particularly limited, and may be a conventional preparation method known in the art. In an example of the present invention, the preparation method includes dissolving a ligand (eg, ligand L-3) and a metal compound (eg, rhodium dicarbonyl acetylacetonate) with a solvent (eg, aromatic hydrocarbon, valeraldehyde, etc.) in a certain proportion , added to the autoclave. After the synthesis gas is introduced for replacement (for example, 3 times of replacement), the pressure is charged (for example, the pressure is charged to 1-2 MPaG, preferably 1.5 MPaG), and the reaction is heated (for example, heated to 60-90 ° C, preferably 80 ° C for 0.5-2 hours. , preferably 1 hour), that is, the formation of a monodentate complex (eg, a monodentate complex I-3).

[0054] In one example of the present invention, suitable solvents are neutral solvents such as benzene, toluene, xylene or mixtures thereof,...

Embodiment 1

[0116] Into a 200mL stainless steel autoclave equipped with a pressure gauge, add 100g of anhydrous toluene solution dissolved with the following catalyst components:

[0117]

[0118]The molar ratio of Rh / P was controlled to be 1:18, the concentration of Rh was 60 ppm, and the molar ratio of rhodium complex to free phosphite ligand was 1:7. After replacing the gas in the kettle three times with synthesis gas (hydrogen: carbon monoxide=1:1), add 10 g of propylene, stir with an electromagnetically driven mechanical stirrer, feed the synthesis gas to a pressure of 0.5 MPaG in the kettle, and heat up to a temperature of 80 °C in the kettle. ℃, feed synthesis gas (hydrogen: carbon monoxide = 1:1) to a total pressure of 1.5 MPaG, maintain the temperature and pressure in the kettle for 0.3 h, and calculate on the basis of propylene, the conversion rate is 98%, and the total amount of butyraldehyde generated in the reaction is 98%. The selectivity was 98.9%, and the molar ratio of...

Embodiment 2

[0120] Into a 200mL stainless steel autoclave equipped with a pressure gauge, add 100g of anhydrous toluene solution dissolved with the following catalyst components:

[0121]

[0122] The molar ratio of Rh / P was controlled to be 1:18, the concentration of Rh was 60 ppm, and the molar ratio of rhodium complex to free phosphite ligand was 1:7. After replacing the gas in the kettle three times with synthesis gas (hydrogen: carbon monoxide=1:1), add 10 g of propylene, stir with an electromagnetically driven mechanical stirrer, feed the synthesis gas to a pressure of 0.5 MPaG in the kettle, and heat up to a temperature of 80 °C in the kettle. ℃, feed synthesis gas (hydrogen: carbon monoxide = 1:1) to a total pressure of 2.0 MPaG, maintain the temperature and pressure in the kettle for 0.3 h, and calculate with propylene as the benchmark, the conversion rate is 97.4%, and the total amount of butyraldehyde generated by the reaction is 97.4%. The selectivity was 98.1%, and the mol...

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Abstract

An olefin hydroformylation catalyst composition and a hydroformylation process are disclosed. The composition includes (a) a catalyst of a formula (I) wherein R11-R35 are hydrogen or C1-20 alkyl, M is selected from rhodium, cobalt, iridium, ruthenium, iron, nickel, palladium, platinum, osmium, or a combination thereof; (b) a monophosphite of a formula (II) or a mixture of the monophosphite of the formula (II) and an oxide of a formula (III), wherein R'11-R'35 and R''11-R''35 are each independently selected from hydrogen or C1-20 alkyl; and (c) a C1-20 alkyl substituted triphenylphosphine. The amount of component (b) is 1 to 10 moles and the amount of the component (c) is 5 to 10 moles, based on 1 mole of the component (a).

Description

technical field [0001] The present invention relates to hydroformylation catalyst compositions and their use in the catalytic formation of isomeric aldehydes such as isobutyraldehyde from olefins such as propylene. High proportions of isobutyraldehyde can be obtained, for example, in the hydroformylation of propylene with the catalyst of the invention. Background technique [0002] Hydroformylation reaction is to make olefins from petrochemical industry and synthesis gas (CO, H 2 ) react to generate normal aldehydes and isomeric aldehydes. Since the reaction product aldehyde can be oxidized or hydrogenated to obtain aldehyde derivatives (such as acids and alcohols) or further hydrogenated through self-condensation to obtain longer chain alcohols and acids, it is widely used as a solvent, additive, and plasticizer raw material , lubricant raw materials, etc. The hydroformylation reaction is the largest homogeneous catalytic reaction process in production so far, and plays ...

Claims

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Application Information

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IPC IPC(8): B01J31/24C07C47/02C07C45/50
CPCB01J31/2409C07C45/505B01J2531/822B01J2231/321C07C47/02
Inventor 杨旭石赖春波马利群费利江易明武范曼曼陈毅立
Owner SHANGHAI HUAYI GRP CO
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