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Method for producing 2-adamantanone

A technology of adamantanone and adamantane is applied in the field of preparation of 2-adamantanone and can solve the problems of slow reaction speed and the like

Inactive Publication Date: 2007-06-13
IDEMITSU KOSAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] But, there is following problem in these methods, that is, although the yield of 2-adamantanone can be improved to 90%, but the reaction rate is slow, in order to obtain such yield, must carry out very long reaction (30 hours or above)

Method used

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Examples

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preparation example Construction

[0016] In the preparation method of 2-adamantanone of the present invention, at least one selected from adamantane and 1-adamantanol is oxidized to prepare 2-adamantanone, and in the preparation method, as an oxidizing agent, a carboxylic acid Oxidants that coexist with sulfuric acid and / or sulfonic acids.

[0017] As the sulfuric acid used in the present invention, sulfuric acid having a concentration of 99-95% by mass generally used in oxidation reactions is preferably used. By setting the concentration of sulfuric acid within the above range, it is possible to suppress the reduction of the reaction rate due to by-produced water and to suppress the generation of tar components.

[0018] In the reaction of the present invention, there is no special limitation on the amount of sulfuric acid relative to adamantane or 1-adamantanol, usually, relative to 1 mass part of adamantane, it is preferably 0.1-150 parts by mass, more preferably 1-100 parts by mass share. When the amount...

Embodiment 1

[0036] Add 1 g of adamantane, 11 g of 98% sulfuric acid and 3 g of trifluoroacetic acid into a 100 mL three-necked flask. The temperature was raised to 60°C while stirring. After reaching 60°C, the reaction was carried out for 4 hours. After the reaction was completed, the reaction solution was poured onto 50 g of ice, and NaOH aqueous solution was added while cooling until pH=9. It was then extracted with 50 mL of toluene. The extract was analyzed by gas chromatography. The results are shown in Table 1.

Embodiment 2

[0038] Reaction, post-processing, and analysis were performed in the same manner as in Example 1 except that monochloroacetic acid was used instead of trifluoroacetic acid. The results are shown in Table 1.

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Abstract

Disclosed is a method for producing 2-adamantanone by oxidizing at least one selected from adamantane and 1-adamantanol wherein sulfuric acid in combination with a carboxylic acid and / or a sulfonic acid is used as an oxidizing agent. By this method, 2-adamantanone can be selectively and efficiently produced in shorter time with higher yield than the conventional methods by oxidizing adamantane or 1-adamantanol.

Description

technical field [0001] The present invention relates to a method for oxidizing adamantane or 1-adamantanol in a short time to prepare 2-adamantanone with high yield, wherein, 2-adamantanone is used as a raw material for various medicines and pesticides in adamantane derivatives And important intermediates of industrial raw materials. Background technique [0002] It is known that adamantane has the same structure as the structural unit of diamond and is a highly symmetrical cage compound. As a chemical substance, it has the following characteristics: (1) Low molecular strain energy and good thermal stability; (2) High fat solubility due to high carbon density; (3) Although sublimable, it has low odor, etc. Since then, in the field of pharmaceuticals, it has attracted attention as a raw material for Parkinson's disease treatment medicine and influenza treatment medicine. In recent years, adamantane derivatives have features such as heat resistance and transparency, and have...

Claims

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Application Information

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IPC IPC(8): C07C45/28C07C45/29C07C49/453C07B61/00
CPCC07C49/453
Inventor 小岛明雄山根秀树冈本贤治
Owner IDEMITSU KOSAN CO LTD
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