Method for preparing 3,3,5-trimethyl-cyclohexanone by selectively hydrogenating isophorone

A technology of trimethylcyclohexanone and isophorone, which is applied in the field of preparation of 3,3,5-trimethylcyclohexanone, can solve problems such as unsatisfactory effect, high cost, and difficulty in product separation

Inactive Publication Date: 2012-10-10
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the boiling points of the product and by-products are similar (the boiling point of 3,3,5-trimethylcyclohexanone is 189°C, and the boiling point of 3,3,5-trimethylcyclohexanol is 191°C), it is difficult for subsequent product separation work. come with great difficulty
[0003] In response to this problem, some new catalysts and solvents for the selective hydrogenation of isophorone have been continuously proposed in recent years (for example, M. Pisarek, M. ?ukaszewski, P. Winiarek, P. K?dzierzawski, M. Janik -Czachor, “Selective catalytic hydrogenation of isophorone on Ni-Al alloy modified with Cr”, Materials Chemistry and Physics , 2009,114,774-779; T. Sato, C. V. Rode, O. Sato, M. Shirai, “Hydrogenation of isophorone with noble metal catalysts in supercritical carbon dioxide”, Applied Catalysis B: Environmental, 2004, 49, 181-185), but they all have the disadvantages of unsatisfactory effect and high cost

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] This example shows that using isophorone as a raw material, the reaction temperature is 100°C, no solvent is added, the reaction time is 4 hours, and a supported 5% Pd / activated carbon catalyst is used (5%Pd / AC catalyst, the mass fraction is 5 % of metal Pd supported on activated carbon), compared the method of hydrogenation of isophorone to 3,3,5-trimethylcyclohydrogenation without adding co-catalyst and adding co-catalyst (mass ratio of 1:1 to Pd) The effect of hexanone.

[0025] Experiment without adding co-catalyst: Take 0.67 g of isophorone and 60 mg of palladium-carbon catalyst (5%Pd / AC) in a 25 mL high-temperature and high-pressure reactor, without adding co-catalyst, and replace the reactor with hydrogen The air in it is finally filled with hydrogen with an initial pressure of 2.0 MPa. Put the reaction kettle into the heating furnace, turn on the stirring, when the temperature rises to 100°C, the stopwatch starts timing, stop stirring after 4 hours, immediately...

Embodiment 2

[0032] This example illustrates the process of using isophorone as the raw material, the mass ratio of co-catalyst and supported Pd catalyst in the reaction material is 1.33:1, the reaction temperature is 100°C, no solvent is added, and the reaction time is 4 hours.

[0033] Take 0.67 g of isophorone, 60 mg of palladium carbon catalyst (5% Pd / AC catalyst, 5% metal Pd supported on activated carbon), and 80 mg of zinc chloride in a 25 mL high-temperature and high-pressure reactor, Charge hydrogen to replace the air in the reactor, and finally charge hydrogen with an initial pressure of 2.0 MPa. Put the reaction kettle into the heating furnace, turn on the stirring, when the temperature rises to 100°C, the stopwatch starts timing, stop stirring after 4 hours, immediately take out the reaction kettle and put it in a cold water bath to terminate the reaction. After the reaction kettle was cooled, it was diluted with dichloromethane and taken out.

[0034] After the reaction product ...

Embodiment 3

[0037] This embodiment illustrates that with isophorone as a raw material, the reaction temperature is 90 ° C, and dichloromethane is used as a solvent, and the reaction time is 4 hours. The mass ratio of the co-catalyst and the loaded Pd catalyst is not added in the co-catalyst or reaction mass. 1:1.1 process method.

[0038] Experiment without adding co-catalyst: 0.67 g of isophorone, 66 mg of palladium carbon catalyst (5% Pd / AC catalyst, 5% metal Pd supported on activated carbon by mass fraction) and about 5 ml of solvent dichloromethane in In the 25 mL high-temperature and high-pressure reactor, hydrogen was filled to replace the air in the reactor, and finally hydrogen with an initial pressure of 2.0 MPa was filled. Put the reaction kettle into the heating furnace, turn on the stirring, when the temperature rises to 90°C, the stopwatch starts timing, stop stirring after 4 hours, immediately take out the reaction kettle and put it in a cold water bath to terminate the reac...

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PUM

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Abstract

The invention provides a method for preparing 3,3,5-trimethyl-cyclohexanone by selectively hydrogenating isophorone (namely 3,3,5-trimethyl-2- cyclohexenone). The method comprises the step of selectively hydrogenating to reduce isophorone into 3,3,5-trimethyl-cyclohexanone through combined use of supported Pd or Pt catalyst and co-catalyst under the condition that the reaction temperature is 20-100 DEG C. The method is remarkably characterized in that the byproduct 3,3,5-trimethyl-cyclohexanol is inhibited by adding the preferred cocatalyst, so that the product 3,3,5-trimethyl-cyclohexanone has relatively high selectivity and yield on the premise of realizing the high conversion rate of the isophorone under a relatively mild condition.

Description

technical field [0001] The present invention relates to a method for preparing 3,3,5-trimethylcyclohexanone, in particular to a method for preparing 3,3,5-trimethylcyclohexanone by selectively hydrogenating and reducing isophorone by adding a cocatalyst to suppress by-product formation. 5-trimethylcyclohexanone method. Background technique [0002] 3,3,5-Trimethylcyclohexanone is an important high-boiling point organic solvent and pharmaceutical synthesis intermediate. The industrial synthesis method is mainly prepared by hydrogenation of isophorone. The molecular structure of isophorone contains a C=C double bond and a C=O double bond. The hydrogenation of isophorone to prepare 3,3,5-trimethylcyclohexanone is to carry out the C=C double bond Hydrogenation. Under the action of a general hydrogenation catalyst, not only the C=C double bond but also the C=O double bond may be hydrogenated to form the by-product 3,3,5-trimethylcyclohexanol. Especially when pursuing a high co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/403C07C45/62B01J23/44B01J23/42
CPCY02P20/54
Inventor 吴卫泽吴桐
Owner BEIJING UNIV OF CHEM TECH
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