Preparation of carvone

A kind of technology of carvone and carvone oxime, which is applied in the field of preparation of carvone, and can solve the problems of not being able to select reagents and the like

Inactive Publication Date: 2002-03-27
快思特国际公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The problem with the use of hydrogenation in the reductive deoximation of carvone oxime is that the choice of reagents is not possible

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Acetic acid (15 ml) was added to a Parr mini-autoclave containing a mixture of L-carvone oxime (10.07 g), 5% palladium catalyst on barium sulfate (0.5672 g) and trilead tetroxide (0.1325 g), water (10ml). The mixture was first flushed with nitrogen, then with hydrogen, and heated to 100°C under a hydrogen pressure of 4.5 MPa, and kept at this temperature and pressure for 23 hours. The progress of the reaction was followed by sampling the mixture and analyzing the extracted samples using gas chromatography. After 23 hours the reaction mixture was found to contain the following composition: Compound Relative Peak Area % Dihydrocarvone 2.27 L-carvone 95.375-Isopropenyl-2-methylphenol 0.54 Hydroxycarvone 0.57 Chromatographic conditions were as follows: System: HP Company HP 6890 gas column: model HP 19091J-412; HP-55% phenylmethylsiloxane capillary: 30m×320μm×0.25μm (nominal) carrier gas: nitrogen, pressure 0.11Mpa, flow rate 0.8ml / min, average Speed ​​29cm / sec steps: 50°...

Embodiment 2

[0033] The outlet port of the high pressure liquid chromatography (HPLC) pump was connected to the Parr microreactor with stainless steel tubing (1.6 mm internal diameter).

[0034] An acetic acid solution containing 22.23% by weight of pure L-carvone oxime was prepared by dissolving 35 grams of pure L-carvone oxime in 122.4 grams of acetic acid. The reagent bottle containing the solution is placed on the balance, and the inlet tube of the high-pressure liquid chromatography pump equipped with the filter is held in place by the clamp and inserted into the solution.

[0035] With 20ml acetic acid, 1ml water, 0.0507g catalyst (BaSO 45% palladium on the carrier) and 0.0109 g of trilead tetroxide were added to a 100 ml Parr reactor. The reactor was then purged with hydrogen, pressurized (with hydrogen) to 4.59 MPa, and the temperature was raised to 127°C. Set the flow rate of the pump to 0.03ml / min, then switch on and start adding the acetic acid solution containing L-carvone ox...

Embodiment 3

[0041] At 112-117°C, add 40ml aqueous solution of anhydrous sodium acetate (20g), acetic acid (250ml), BaSO 4 In the reflux suspension of 5% palladium catalyst (20.1g) and trilead tetraoxide (1.94g) on ​​the carrier, a formic acid solution of L-carvone oxime (534.27g, containing 36% carvone oxime, according to the above Method prepared from D-limonene). The reaction was then refluxed for an additional 8 hours. It was analyzed by GC and when the reaction was complete it was cooled to room temperature. Deionized water (400ml) was then added and the reaction mixture was stirred. The organic and aqueous phases were separated and the organic layer solvent was removed in vacuo to yield 434.44 g of crude product. It was found by internal standard GC that the crude product contained 39.1% carvone (method and chromatographic conditions are as shown in Example 2), so the yield of the reaction was 81.35%.

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PUM

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Abstract

A process for the preparation of carvone comprises hydrogenating carvoxime in the presence of a selecively poisoned catalyst. Preferred catalysts include noble metals supported on inorganic materials poisoned with a catalyst modifier. In a preferred embodiment of the process defined herein, the crude carvone reaction product produced in accordance with the process of the invention, is purified by treating the crude carvone product with an organometallic compound M(X)n wherein M is a polyvalent metal, n is the valence of M and X denotes an inorganic or organic atom or group.

Description

field of invention [0001] The present invention relates to the preparation of carvone (5-isopropenyl-2-methyl-2-cyclohexen-1-one), in particular to the preparation of carvone oxime (5-isopropenyl-2-methyl- 2-cyclohexen-1-one oxime) into carvone. Background of the invention [0002] L-carvone (5(R)-isopropenyl-2-methyl-2-cyclohexen-1-one) is widely used as a flavoring agent or flavoring agent for toothpaste or tooth powder, chewing gum, mouthwash agent etc. In these dental applications, high purity carvone is very important and it is especially important that the content of hydroxyl compounds such as terpineol which is usually a by-product in carvone synthesis is low. These substances generally cannot be separated from carvone by distillation and require laborious, expensive, adequate flow acid sulfite extraction and washing to remove the contaminants. US 5,302,759 discloses another suitable method for isolating by-products such as alpha-terpineol. The method described in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J27/053C07B53/00C07B61/00C07C45/00C07C45/44C07C45/85C07C49/403C07C49/647
CPCC07C45/00C07C45/85C07C49/647
Inventor P·N·戴维C·P·纽曼W·A·添希-拉姆·采
Owner 快思特国际公司
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