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Preparation of 3, 5, 5-trimethyl-cyclohex-2-ene-1, 4-dione

A technology of trimethyl and cyclohexane is applied in the field of preparation of 3,5,5-trimethyl-cyclohex-2-ene-1,4-dione, and can solve problems such as adverse effects of preparation cost and the like

Inactive Publication Date: 2005-05-11
DEGUSSA AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0028] In addition, the use of ether as a solvent for the oxidation reaction involves the danger of the formation of highly explosive peroxides already described
Furthermore, diglyme is a very expensive solvent, which has an adverse effect on the preparation costs of the method, so the use of diglyme as a solvent for the reactions studied is economically less desirable

Method used

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  • Preparation of 3, 5, 5-trimethyl-cyclohex-2-ene-1, 4-dione
  • Preparation of 3, 5, 5-trimethyl-cyclohex-2-ene-1, 4-dione
  • Preparation of 3, 5, 5-trimethyl-cyclohex-2-ene-1, 4-dione

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-12

[0072] First, 58.0 g of solvent specified in Table 1, 1.2 g of water, 0.16 g of acetylacetone, 2.53 g of triethylamine and the amount of Saren manganese that can be seen from Table 1 were put into a glass beaker and stirred for 15 minutes (variation variant A) or 16 hours (variant B). Then 15.4 g of β-IP were added and the reaction mixture was briefly stirred and transferred into a bubble column. Under normal pressure and 35°C, it was blown with oxygen (12 l / h) for 2.5 hours, and then the yield of KIP was determined by gas chromatography with internal standard method. The results are listed in Table 1.

Embodiment 13-15

[0077] First 72.5 grams of DMF, 1.56 grams of water, 0.21 grams of acetylacetone, 3.18 grams of triethylamine, the amount of acid specified in Table 2, and 75 mg of Saren manganese were placed in a glass beaker and stirred for 15 minutes. Then 19.25 g of β-IP were added and the reaction mixture was briefly stirred and transferred into a bubble column. Under normal pressure and 35°C, it was blown with oxygen (16 l / h) for 2.5 hours, and then the yield of KIP was determined by gas chromatography with internal standard method. The results are listed in Table 2.

Embodiment 16-22

[0083] In a solution of approximately 100 g of β-IP, triethylamine, water, acetylacetone and saran manganese in DMF at atmospheric pressure and 35 °C, the concentration can be read from Table 3. Oxygen aeration (16 l / h) for 2.5 hours, and then the yield of KIP was determined by gas chromatography using an internal standard method. The results are listed in Table 3.

[0084] Example

β-IP

[mol / l]

Triethylamine

[mol / l]

water

[mol / l]

Acetylacetone

[mol / l]

Salem MN

[mol / l]

KIP yield

[%]

16

0.54

0.30

0.80

115

3.81

92.6

17

1.08

0.30

0.81

113

3.79

91.7

18

1.59

0.30

0.81

167

5.57

89.4

19

2.11

0.29

0.79

222

7.38

87.7

20

2.62

0.29

0.78

273

9.14

85.7

21

3.85

0.29

0.78

37...

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Abstract

The present invention relates to an improved process for the preparation of 3,5,5-trimethylcyclohex-2-ene-1,4-dione by oxidation of 3,5,5-trimethylcyclohex-3-en-1-one in the presence of an oxidizing agent and a catalyst system comprising a transition metal complex, catalyst, an auxiliary base, possibly water, and a catalytically active co-additive, characterized in that carboxylic acid amides are employed as the solvent.

Description

technical field [0001] The present invention relates to the preparation of 3,5,5-trimethyl-cyclohex-2- Improved process for ene-1,4-dione (ketone isophorone). Background technique [0002] Ketoisophorone (KIP) is an important intermediate product in the synthesis of trimethylhydroquinone or trimethylhydroquinone ester, which in turn is an intermediate product in the synthesis of vitamin E . In addition, KIP is an intermediate in the production of many carotenoids such as astaxanthin, zeaxanthin and canthaxanthin, for example. [0003] KIP is known to be produced by oxidation of α-isophorone or β-isophorone (β-IP). [0004] According to Hosokawa et al. (Chem. Lett., 1983, 1081-1082), the oxidation of α-isophorone to KIP was achieved by tert-butyl hydroperoxide in the presence of 10 mol% palladium acetate and an auxiliary base with maximum yield The rate is 55%. In addition to the high amount of catalyst and the low yields that can be achieved, especially the use of the e...

Claims

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Application Information

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IPC IPC(8): B01J31/22C07B61/00C07C45/34C07C49/603
CPCC07C45/34C07C2601/16C07C49/603
Inventor 拉尔夫·马森福尔克尔·黑夫纳斯特芬·克里尔于尔根·比尔茨格奥尔格·马尔科夫兹克劳斯·胡特马赫尔
Owner DEGUSSA AG
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