Methods for recovering and reusing selective homogeneous hydrogenation catalyst

A hydrogenation catalyst and selective technology, which is applied in the direction of carbon compound catalyst, physical/chemical process catalyst, organic compound/hydride/coordination complex catalyst, etc. period, the effect of reducing harmful effects

Pending Publication Date: 2021-07-30
HANWHA SOLUTIONS CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are disadvantages of the large amount of catalyst required and the need for solvents for phase separation

Method used

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  • Methods for recovering and reusing selective homogeneous hydrogenation catalyst
  • Methods for recovering and reusing selective homogeneous hydrogenation catalyst
  • Methods for recovering and reusing selective homogeneous hydrogenation catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] Cyclododecatriene (CDT), ruthenium chloride (RuCl 3 ), triphenylphosphine (TPP) and formaldehyde, the reaction solution was stirred under the condition of 6 bar hydrogen, and the selective hydrogenation was carried out at 160° C. and 20 bar for 2 hours. In this case, the reaction was carried out in a stirred tank reactor equipped with a gas induction hollow stirrer.

[0091] Selective hydrogenation was performed for 2 hours, the temperature was cooled to 30°C or lower under nitrogen to recover the reaction solution, and the reaction solution was distilled in a distillation apparatus at 0.1 bar or less and 110°C.

[0092] After the distillation is complete, the temperature is cooled to 30° C. or lower under nitrogen to recover the selective homogeneous hydrogenation catalyst.

Embodiment 2

[0094] Selective hydrogenation was performed by newly adding the recovered selective homogeneous hydrogenation catalyst to the reaction solution in the same manner as in Example 1.

[0095] More specifically, cyclododecatriene (CDT) and the recovered selective homogeneous hydrogenation catalyst were added in a molar ratio of 7500:1, the reaction solution was stirred under 6 bar hydrogen and kept at 160 °C and 20 bar Selective hydrogenation was carried out under the condition of 2 hours. In this case, the reaction was carried out in a stirred tank reactor equipped with a gas induction hollow stirrer.

[0096] Selective hydrogenation was performed for 2 hours, the temperature was cooled to 30°C or lower under nitrogen to recover the reaction solution, and the reaction solution was distilled in a distillation apparatus at 0.1 bar or less and 110°C.

[0097] After the distillation is complete, the temperature is cooled to 30° C. or lower under nitrogen to recover the selective ho...

experiment example 1

[0099]

[0100] The conversion and selectivity of the recovered selective homogeneous hydrogenation catalyst for each of Example 1 and Example 2 were calculated. The results are shown in Table 1.

[0101] [Table 1]

[0102] Conversion rate(%) Selectivity (%) Example 1 98.7 98.5 Example 2 98.7 97.1

[0103] As a result, as shown in Table 1, it could be confirmed that the conversion and selectivity in the initial selective hydrogenation were almost the same as those in the second selective hydrogenation using the recovered selective homogeneous hydrogenation catalyst. Specifically, it can be determined that C 2 / C 1 × 100 is 100, which indicates that the conversions in the two reactions are the same as each other, and S 2 / S 1 ×100 was 98.6, which indicated that the selectivities in the two reactions were almost the same as each other.

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PUM

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Abstract

The present invention pertains to a method for recovering a selective homogeneous hydrogenation catalyst and a method for reusing the recovered selective homogeneous hydrogenation catalyst. The method for recovering a selective homogeneous hydrogenation catalyst comprises: a step for synthesizing cyclododecene by selectively hydrogenating a first reaction solution containing cyclododecatriene, triphenylphosphine, formaldehyde, and ruthenium chloride, wherein a selective homogeneous hydrogenation catalyst is prepared during the selective hydrogenation reaction from the triphenylphosphine, formaldehyde, and ruthenium chloride to synthesize the cyclododecene; and a step for distilling and separating unreacted cyclododecatriene and cyclododecadiene, as well as the product cyclododecene, from a second reaction solution in which the cyclododecene synthesis has been completed, and recovering the selective homogeneous hydrogenation catalyst.

Description

technical field [0001] The present invention relates to a process for the recovery and reuse of selective homogeneous hydrogenation catalysts. Background technique [0002] The synthesis of cyclododecene (CDEN) by selective hydrogenation starting from cyclododecatriene (CDT) is frequently described in the literature and many studies have been carried out to increase the yield of cyclododecene. [0003] For selective hydrogenation, metal-ligand catalysts known as Wilkinson catalysts have been used, i.e., in which a ligand such as triphenylphosphine (TPP) or CO and a halogen atom are combined with a metal such as rubidium (Ru ), rhodium (Rh), cobalt (Co) or nickel (Ni) combined catalysts. [0004] Generally, a catalyst is a substance that accelerates the activation of the entire reaction in a certain reaction system without reacting itself, and is an indispensable substance in the chemical industry. Catalysts usually exist in a small amount in the reaction system and play th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C5/05C07C7/04C07C7/20C07C13/275
CPCC07C7/04C07C2527/13C07C5/05C07C2601/20Y02P10/20C07C13/275C07C7/20Y02P20/584Y02P20/52B01J31/2409B01J31/4053B01J2231/645B01J2531/821
Inventor 金荣镇张南镇宋圭镐
Owner HANWHA SOLUTIONS CORP
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