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Method for preparing aldehyde compound by olefin hydroformylation

A technology of aldehyde compounds and olefin hydroformyl, which is applied in the chemical industry, can solve the problems of high solvent toxicity, complicated process, and many high boiling substances, and achieve the effects of increasing solubility, stable catalytic system, and easy separation

Active Publication Date: 2016-03-23
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method can effectively remove the cobalt catalyst in the hydroformylation product (can be removed to below 1ppm), the process is relatively complicated, requiring mechanical coalescence and electric field treatment, many equipment and complicated operation
[0006] In view of the deficiencies in the above-mentioned processes, it is urgent to develop a new type of hydroformylation catalytic system and hydroformylation method to overcome the existing problems in current production that using products or other organic substances as solvents can easily lead to many high boiling substances and high solvent toxicity , partial direct hydrogenation of olefins, activation in the catalyst recovery process, etc.

Method used

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  • Method for preparing aldehyde compound by olefin hydroformylation
  • Method for preparing aldehyde compound by olefin hydroformylation
  • Method for preparing aldehyde compound by olefin hydroformylation

Examples

Experimental program
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Effect test

preparation example

[0029] Phosphorus ligand L1 and its catalyst mother liquor Q 1 and Q 2 Preparation of:

[0030] 43.3g phenylethylenediamine Mix well with 24.3g of 37% formaldehyde aqueous solution, react at 60°C for 70min, then add 13.7g of PCl dropwise to the system 3 With 24.8g 2-chloroethanol, add 100g deionized water at the same time, continue to stir for 50min, obtain the aqueous solution containing phosphorus ligand L1, the concentration is 36.6wt%, adopt NMR qualitative, 1 HNMR data (CDCl 3 as solvent, TMS as internal standard): 7.98(m, 3H, -CH), 7.52(m, 9H, -CH), 7.5(m, 3H, NCH-), 4.17(t, 6H, HOCH 2 -),3.65(s,3H,-HO),3.6(s,6H,N-CH 2 -N),1.68(t,6H,N-CH 2 -).

[0031] The structural formula of L1 is:

[0032]

[0033] Add 1.02g rhodium dicarbonyl acetylacetonate to the 100g aqueous solution containing L1 ligand prepared above, and stir for 30min under nitrogen protection to obtain catalyst mother liquor Q 1 .

[0034] 100gL of the above prepared 1 Add 0.6g rhodium dicarbo...

Embodiment 1

[0047] Catalyst mother liquor Q 1 ,Such as figure 1 As shown, the air in reactor A was replaced with nitrogen for 3 times before feeding, and the catalyst mother liquor 3 and olefin 1 were respectively added to reactor A by using an advection pump. The volume ratio of catalyst mother liquor 3 and olefin 3 was 0.5, stirred and mixed evenly, and then Replace with synthesis gas 2 for 3 times, then increase the pressure to 2.0-15MPa, raise the temperature to 80-150°C, and react at constant pressure for 3-5 hours. Cool down to room temperature, release the pressure, take out the reaction solution, and analyze the composition of the reaction solution by gas chromatography. The results show that the conversion rate of olefins is 50-65%, and the selectivity of aldehydes is >99.0%. The specific results are shown in Table 1. Reactor discharge 4 enters in phase separator B, is separated into oil phase 5 and water phase 6, and water phase 6 is circulated back to reactor A, and oil phase ...

Embodiment 2

[0051] Catalyst mother liquor Q 2 , The volume ratio of the catalyst mother liquid to the olefin is 1.0, pressurize to 1.8-14MPa, heat up to 85-165°C, and react at constant pressure for 3-5 hours, and the rest are the same as in Example 1. Cool down to room temperature, release the pressure, take out the reaction solution, and analyze the composition of the reaction solution by gas chromatography. The results show that the conversion rate of olefins is 53-69%, and the selectivity of aldehydes is >99.0%. The specific results are shown in Table 2.

[0052] Table 2:

[0053] Olefin

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Abstract

The present invention discloses a method for preparing an aldehyde compound by olefin hydroformylation. Under the action of a catalyst mother solution, the olefins and synthesis gas react to generate the aldehyde compound through gas-liquid contact. The catalyst mother solution is a rhodium carbonyl aqueous solution generated by a rhodium compound and a phosphorus ligand. Oil-water two-phase separation is performed after the reaction, the catalyst mother solution is recycled along with a water phase, the oil phase is separated into the aldehyde product and unreacted olefins, and the unreacted olefins are reused in reactions. According to the method disclosed by the present invention, water is used as a reaction solvent, and the catalyst is high in activity and can be recycled in a plurality of times. The method is simple in operation and good in economic benefit.

Description

technical field [0001] The invention relates to a method for preparing aldehyde compounds by hydroformylation of olefins, belonging to the technical field of chemical industry. technical background [0002] Aldehyde compounds are an important chemical raw material. Aldehydes have strong chemical properties and can react with various compounds to produce corresponding alcohols, acids, esters, acetals and other derivative products. Hydroformyl Carbonylation (carbonylation) is one of the main methods for preparing aldehydes from olefins in industry. According to the difference of carbonylation reaction pressure and catalyst, the carbonylation method can be divided into high-pressure cobalt method and medium-pressure method (improved cobalt method, improved rhodium method), low pressure method (low pressure rhodium method, improved rhodium method) and other processes. [0003] The low-pressure method mainly used in production at present, such as propylene hydroformylation uses ...

Claims

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Application Information

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IPC IPC(8): C07C45/50C07C47/02C07C47/21C07C67/293C07C69/14B01J31/24
CPCY02P20/584C07C45/50B01J31/189B01J31/20B01J2231/321B01J2531/822B01J2540/50C07C67/293C07C47/02C07C47/21C07C69/14
Inventor 王中华何岩刘振峰吴华杰袁帅宋伟锋黄少峰吕艳红陈志刚王灿昌黎源
Owner WANHUA CHEM GRP CO LTD
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