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Preparation method for cyclopentanol and cyclopentanone by oxidation of cyclopentane

A technology for cyclopentanol and cyclopentane, which is applied in the field of preparing cyclopentanol and cyclopentanone, can solve the problems of large circulation of cyclopentene as a raw material, difficulties in the separation and purification process, and difficulties in the recovery of concentrated sulfuric acid, and achieve low cost and reduced The effect of reducing production cost and separation cost

Active Publication Date: 2016-01-13
山东友道化学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The conversion rate of indirect hydration is high and the selectivity is good, but a large amount of concentrated sulfuric acid is used in the synthesis process, which requires high corrosion resistance of equipment, and the recovery of concentrated sulfuric acid is difficult, and the environmental pollution is very serious. Amyl alcohol new technology " (Xu Zehui etc., chemical world, 2002,4,199-202) described
Direct hydration avoids the use of highly polluting concentrated sulfuric acid, but the disadvantages are that the reaction conversion rate is relatively low, the circulation of raw material cyclopentene is large, and the product refining energy consumption is high
The disadvantage is that the total selectivity of the cyclopentanol and cyclopentanone of the invention is only about 78%, which will lead to more impurities in the target product, and the subsequent separation and purification process is difficult

Method used

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  • Preparation method for cyclopentanol and cyclopentanone by oxidation of cyclopentane
  • Preparation method for cyclopentanol and cyclopentanone by oxidation of cyclopentane
  • Preparation method for cyclopentanol and cyclopentanone by oxidation of cyclopentane

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] The catalyst dissolved in fresh cyclopentane 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 cyclopentane added to the oxidation reactor is 15.5mL / 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 165° C., and the reaction pressure is 2.0 MPa. After sampling analysis, the conversion rate of cyclopentane in the system is 99.1%, and the total selectivity of cyclopentanol and cyclopentanone is 98.4%, wherein the selectivity of cyclopentanol is 62.6%, and the selectivity of cyclopentanone is 35.8%. %.

Embodiment 2

[0051] The catalyst that dissolves in the fresh cyclopentane 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 cyclopentane added to the oxidation reactor is 1.2mL / 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 to maintain the system reaction temperature at 120°C and the reaction pressure at 0.7MPa. After sampling analysis, the conversion rate of cyclopentane in the system is 99.4%, and the total selectivity of cyclopentanol and cyclopentanone is 98.0%, wherein the selectivity of cyclopentanol is 58.4%, and the selectivity of cyclopentanone is 39.6%. %.

Embodiment 3

[0053] The catalyst dissolved in the fresh cyclopentane 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 cyclopentane added in the oxidation reactor was 2.2mL / h, and the average residence time of the oxidation reactor in terms of liquid phase material was 3.5h at this moment, 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 132° C., and the reaction pressure is 0.9 MPa. After sampling analysis, the conversion rate of cyclopentane in the system is 99.6%, and the total selectivity of cyclopentanol and cyclopentanone is 97.8%, wherein the selectivity of cyclopentanol is 56.7%, and the selectivity of cyclopentanon...

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Abstract

The invention discloses a preparation method for cyclopentanol and cyclopentanone by oxidation of cyclopentane. The method comprises the following steps: (1) continuously introducing the cyclopentane, a catalyst and oxygen-contained gas into an oxidation reactor and carrying out reaction so as to obtain an oxidation reaction liquid containing the cyclopentanol and the cyclopentanone, wherein the concentration of tail oxygen is controlled within 3% by controlling the introduction amount of the oxygen-contained gas; the usage amount of the catalyst accounts for 1 to 10000 ppm of the weight of the cyclopentane; reaction temperature is 120 to 170 DEG C; reaction pressure is 0.7 to 3.0 MPa; and average retention time of the oxidation reactor in terms of a liquid-phase material is 0.4 to 6 hours; and (2) allowing the oxidation reaction liquid obtained in the step (1) to continuously enter a distillation tower, subjecting a cyclopentane-contained light component obtained from the top of the tower to recycling back to the oxidation reactor, and subjecting crude cyclopentanol and crude cyclopentanone obtained from the bottom of the tower to separation and purification so as to respectively obtain the cyclopentanol and the cyclopentanone. The preparation method provided by the invention has the advantages of mild reaction conditions, high product yield, good selectivity, greenness and environmental protection.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals manufacture, and in particular relates to a method for preparing cyclopentanol and cyclopentanone by oxidation of cyclopentane. Background technique [0002] Cyclopentanone, a colorless liquid with mint aroma, melting point -58.2°C, boiling point 130.6°C, miscible with alcohol and ether, insoluble in water. It is easy to polymerize, especially in the presence of trace amounts of acid, and is mainly used as an intermediate for medicine, spices, synthetic rubber, and pesticides. [0003] Cyclopentanol, colorless, aromatic, viscous, clear liquid with pleasant smell, melting point -19°C. The boiling point is 140.8°C. Soluble in ethanol, slightly soluble in water. It is mainly used as a solvent and dye intermediate for spices and medicines. [0004] At present, the main synthesis methods of cyclopentanone are pyrolysis of adipic acid, oxidation of cyclopentene and catalytic dehydrogenation o...

Claims

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Application Information

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IPC IPC(8): C07C35/06C07C29/50C07C49/395C07C45/33C07C27/12
CPCC07C29/50C07C45/33C07C35/06C07C49/395
Inventor 王勤波熊振华陈楚雄
Owner 山东友道化学有限公司
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