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Complex catalyst system and application thereof to decomposition of naphthene hydrogen peroxide

A cycloalkyl hydroperoxide, catalyst technology, applied in the direction of organic compound/hydride/coordination complex catalyst, physical/chemical process catalyst, chemical/physical process, etc., can solve the problem of expensive, reactor wall fouling , catalyst deactivation and other problems to avoid precipitation and scaling

Active Publication Date: 2012-04-04
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these homogeneous complex catalysts still have many deficiencies
For example, some ligands with complex structures, such as porphyrin, phthalocyanine and 1,3-bis(2-pyridylimine) isoindoline are expensive, and some complex catalysts use metal hydrochloride, so as to contribute to the reaction The system brings corrosive Cl - ion
Moreover, these metal complexes are affected by high temperature, moisture and organic acids during use, which will form metal precipitates, which will lead to catalyst deactivation and cause fouling problems on the reactor wall

Method used

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  • Complex catalyst system and application thereof to decomposition of naphthene hydrogen peroxide
  • Complex catalyst system and application thereof to decomposition of naphthene hydrogen peroxide

Examples

Experimental program
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Effect test

reference example 1

[0021] Reference Example 1: Preparation of Cyclohexane Oxidation Solution Containing Cyclohexyl Hydroperoxide

[0022] Cyclohexane oxidation was carried out in a 10-liter stainless steel reactor equipped with heating, mechanical stirring, ventilation and reflux. First add 7 liters of cyclohexane into the kettle, raise the temperature of the reaction kettle to 160°C under nitrogen, keep the pressure at 1.2MPa, change the nitrogen to air, the air flow rate is 8 liters / min, and stir the reaction at constant temperature for 1 hour. Analyze the cyclohexane oxidation solution prepared, this oxidation solution contains cyclohexyl hydroperoxide 0.44mmol / g, cyclohexanone 0.06mmol / g, cyclohexanol 0.12mmol / g, and oxidation by-products such as a small amount of organic acid and ester .

Embodiment 1

[0024] (1) Preparation of complex catalyst: N-butylimidazole complex copper dodecylbenzenesulfonate

[0025] Weigh 4.24g of dodecylbenzenesulfonic acid and 0.628g of copper hydroxide, add them to 20g of deionized water, heat and stir at 80°C for 20 minutes, then evaporate to dryness to obtain 4.62g of light white solid dodecylbenzene Copper sulfonate (C 12 h 25 C 6 h 4 SO 3 ) 2 Cu. Weigh 2.36g prepared copper dodecylbenzenesulfonate and 0.821g N-butylimidazole, add to reflux in 10ml ethanol for 30 minutes, evaporate to dryness, obtain 3.18g blue solid, this solid is through elemental analysis, Determine the composition as (C 12 h 25 C 6 h 4 SO 3 ) 2 Cu(C 7 h 12 N 2 ) 2 , Weigh 1.5g of this blue solid and dissolve it in 10ml of ethanol to make blue catalyst solution A.

[0026] (2) Catalytic decomposition of cyclohexyl hydroperoxide

[0027] The decomposition reaction is carried out in a 500ml stainless steel reaction kettle with a reflux water separation cond...

Embodiment 2

[0029] (1) Preparation of complex catalyst: N-methylimidazole complex copper dodecylsulfonate

[0030] Weigh 2.43g of sodium dodecylsulfonate and dissolve it in 49.8g of deionized water to obtain solution 1; then weigh 0.76g of copper chloride and dissolve it in 14.9g of deionized water to obtain solution 2. At room temperature under stirring conditions, solution 2 was slowly added dropwise to solution 1, and stirring was continued for 1 hour after the drop was completed, and a light blue solid precipitate was obtained. This precipitate is dried after centrifugation, deionized water washing 5 times, obtains 2.1g light blue powdery solid copper dodecylsulfonate (C 12 h 25 SO 3 ) 2 Cu.

[0031] Weigh 1.00g of the prepared copper dodecylsulfonate and 0.292g of N-methylimidazole, add it to 10ml of ethanol, heat and reflux at 80°C for 20 minutes, evaporate the solvent to obtain 1.28g of blue solid powder , this solid is determined to be composed of (C 12 h 25 SO 3 ) 2 Cu(C...

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Abstract

The invention discloses a complex catalyst system and application thereof to decomposition of naphthene hydrogen peroxide. The catalyst system is AxMFn, wherein A is a strong acid anion, M is an active center transition metal cation, and F is an organic ligand of a nitrogen-containing heteroatom; the strong acid anion A is a strong acid radical anion containing lipophilic C4-C30 long-chain alkyl;x represents an anion mole number corresponding to every mole of transition metal cation M; and n represents the mole number of the ligand F contained in every mole of transition metal M anion. Due to the adoption of the complex catalyst system, naphthene hydrogen peroxide can be decomposed stably into naphthene alcohol and naphthene ketone under the liquid phase condition of 80-150 DEG C, and catalyst metal is prevented from precipitating and scaling.

Description

technical field [0001] The present invention relates to the decomposition of cycloalkyl hydroperoxide; Specifically, relate to homogeneous phase complexation catalytic decomposition cycloalkyl hydroperoxide, prepare the production method of corresponding cycloalkyl ketone and cycloalkyl alcohol, such as cyclohexyl Catalyzed decomposition of hydrogen peroxide to produce cyclohexanol and cyclohexanone. technical background [0002] Cycloalkyl hydroperoxide is an intermediate product of cycloalkane free radical oxidation, and this intermediate can be decomposed to obtain final products cycloalkyl alcohol and cycloalkyl ketone. [0003] Take the industrial production process of cyclohexane oxidation to produce cyclohexanol and cyclohexanone as an example. Cyclohexane is first oxidized by air to obtain an oxidized solution containing cyclohexyl hydroperoxide. This oxidized solution must be further decomposed to make it The cyclohexyl hydroperoxide decomposes to the final cyclohe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22C07C27/04C07C29/132C07C45/53C07C35/06C07C35/08C07C35/205C07C35/20C07C35/28C07C49/395C07C49/403C07C49/413C07C49/433
Inventor 孙志强徐杰郑玺
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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