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Method for preparing cyclooctanol and cyclooctanone through cyclooctane oxidation

A technology of cyclooctanol and cyclooctane, which is applied in the field of fine chemical manufacturing, can solve the problems of expensive oxidants and serious pollution, and achieve the effects of low cost, high selectivity and high conversion rate

Inactive Publication Date: 2016-01-13
JIANGXI KEYUAN BIOPHARM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The common disadvantage of the above methods is that a strong chemical oxidant is used for the reaction, and the oxidant is expensive and pollutes seriously

Method used

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  • Method for preparing cyclooctanol and cyclooctanone through cyclooctane oxidation
  • Method for preparing cyclooctanol and cyclooctanone through cyclooctane oxidation
  • Method for preparing cyclooctanol and cyclooctanone through cyclooctane oxidation

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Experimental program
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Effect test

Embodiment 1

[0048] The catalyst dissolved in the fresh cyclooctane added to the system is Co(Ac) 2 .4H 2 O, metal phthalocyanine (R) with general formula (IV) structure 1 =CH 3 CH 2 , R 2 =H, M=Mn), the metalloporphyrin (R 1 =R 2 = H, R 3 =CH 3 , M=Cu) mixture with a total concentration of 225 ppm. When the device is in steady state operation, the flow rate of fresh cyclooctane added to the oxidation reactor is 22.5mL / h. At this time, the average residence time of the oxidation reactor in terms of liquid phase substances is 0.4h, and the pressurized air is continuously fed into the In the oxidation reactor, the reaction temperature of the system is maintained at 237° C., and the reaction pressure is 1.8 MPa. After sampling analysis, the conversion rate of cyclooctane in the system is 98.1%, and the total selectivity of cyclooctanol and cyclooctanone is 91.6%, wherein the selectivity of cyclooctanol is 71.9%, and the selectivity of cyclooctanone is 19.7%. %.

Embodiment 2

[0050] The catalyst that dissolves in the fresh cyclooctane that adds system is N-hydroxyl phthalimide, the metal phthalocyanine (R with general formula (IV) structure 1 =OH, R 2 =H, M=Ru) and metalloporphyrins (R 1 =R 3 = H, R 2 =OH,M 1 = M 2 =Mn), the total concentration is 10000ppm. When the device is in steady state operation, the flow rate of fresh cyclooctane added to the oxidation reactor is 2.1mL / h. At this time, the average residence time of the oxidation reactor in terms of liquid phase substances is 6.0h, and the pressurized pure oxygen is continuously passed through into the oxidation reactor, maintaining the reaction temperature of the system at 120°C and the reaction pressure at 0.1MPa. After sampling analysis, the conversion rate of cyclooctane in the system is 98.4%, and the total selectivity of cyclooctanol and cyclooctanone is 90.7%, wherein the selectivity of cyclooctanol is 64.7%, and the selectivity of cyclooctanone is 26.0%. %.

Embodiment 3

[0052] The catalyst dissolved in the fresh cyclooctane added to the system is Cr(NO 3 ) 4 , N-acetyl phthalimide, metal phthalocyanine (R 1 =OCH 3 , R 2 =H, M=Ni) and the metalloporphyrin (R 1 =R 3 =OCH 3 , R 2 =H, M=Fe) with a total concentration of 7800 ppm. During the steady state operation of the device, the flow rate of the fresh cyclooctane added in the oxidation reactor was 4.0mL / h. At this time, the average residence time of the oxidation reactor in terms of liquid phase material was 3.5h, and the oxygen concentration was 76%. The pressurized oxygen enrichment is continuously passed into the oxidation reactor, and the reaction temperature of the system is maintained at 151° C., and the reaction pressure is 0.3 MPa. After sampling analysis, the conversion rate of cyclooctane in the system is 98.6%, and the total selectivity of cyclooctanol and cyclooctanone is 90.3%, wherein the selectivity of cyclooctanol is 61.8%, and the selectivity of cyclooctanone is 28.6%....

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Abstract

The invention discloses a method for preparing cyclooctanol and cyclooctanone through cyclooctane oxidation. The method comprises the following steps: (1) cyclooctane, a catalyst and an oxygen-containing gas are continuously delivered into an oxidation reactor, such that a reaction is carried out, wherein tail oxygen concentration is controlled at within 5% through controlling the input amount of the oxygen-containing gas, the usage amount of the catalyst is 5-10000ppm of the total weight of cyclooctane, a reaction temperature is 120-250 DEG C, a reaction pressure is 0.1-2.0MPa, and an oxidation reactor average retention time calculated according to liquid-phase substances is 0.4-6h, such that oxidation reaction liquid containing cyclooctanol and cyclooctanone is obtained; (2) the oxidation reaction liquid obtained in the step (1) is continuously delivered into a rectification tower; a light component comprising cyclooctane is obtained at the tower top, and is recycled in the oxidation reactor; cyclooctanol and cyclooctanone crude products are obtained at the tower bottom; and the crude products are respectively purified, such that cyclooctanol and cyclooctanone products are obtained. The method provided by the invention is green and environment-friendly, and has the advantages of mild reaction conditions, high product yield, and good selectivity.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals manufacture, and in particular relates to a method for preparing cyclooctanol and cyclooctanone by oxidation of cyclooctane. Background technique [0002] Both cyclooctanone and cyclooctanol are important chemical intermediates, mainly used in organic synthesis and pharmaceutical synthesis, and are mainly produced by oxidation of cyclooctane. [0003] There are only some synthetic methods about cyclooctanone and cyclooctanol in published papers. Investigated the influence of the metalloporphyrins of different axial ligands on the cyclooctane oxidation process as Haber etc., the yield of cyclooctanone reaches 20.1% under the optimal condition, and the yield of cyclooctanol reaches 2.3% (J.Mol . Catal. A, 2000, 162, 105; 2003, 198, 215). Mohajer et al. studied the effect of metalloporphyrins with different structures on the oxidation products of cyclooctane, using Mn(TPP)OAc as catalyst, CH...

Claims

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Application Information

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IPC IPC(8): C07C29/50C07C29/80C07C35/20C07C45/33C07C45/82C07C49/413
CPCC07C29/50C07C29/80C07C45/33C07C45/82C07C35/20C07C49/413
Inventor 王勤波熊振华陈楚雄
Owner JIANGXI KEYUAN BIOPHARM
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