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Method for production of adamantanol

A technology of adamantanol and adamantane, which is applied in the field of preparing adamantanols, can solve problems such as increased raw material costs and expensive catalysts, and achieve high yields

Active Publication Date: 2010-11-24
OSAKA ORGANIC CHEM INDS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In this bromination method, since the raw material is brominated first, the cost of the raw material is high, and the catalyst for hydrolyzing the produced bromine derivative is also expensive.

Method used

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  • Method for production of adamantanol

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Experimental program
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Effect test

Embodiment 1

[0050] 30 mL (582 mmol) of 25% by mass fuming sulfuric acid was added to a 100 mL four-necked flask, 2.4 g (58.5 mmol) of acetonitrile and 6.0 g (44.1 mmol) of adamantane were added, and the mixture was reacted at a reaction temperature of 25° C. for 3 hours. It should be noted that the molar ratio of oleum to the raw material adamantane was 13.2 (=582 / 44.1).

[0051] Next, the reaction liquid was added dropwise to 90 g of water at 70° C. charged in a 4 L four-necked flask. When the dropwise addition was completed, the temperature of the mixed liquid of water and the reaction liquid was 75°C. After the dropwise addition was completed, the hydrolysis was completed by stirring at 80° C. for 30 minutes. After cooling to room temperature, the precipitated crystals were filtered and dried to obtain 6.6 g of crystals.

[0052] According to gas chromatography analysis, the crystals were 1-adamantanol with a GC purity of 99.6%, and the yield was 98%.

Embodiment 2

[0054] Except having adjusted the addition amount of acetonitrile to 3.6 g (87.7 mmol), the same operation as Example 1 was performed. As a result, 6.5 g of 1-adamantanol with a GC purity of 99.7% was obtained, and the yield was 97%.

Embodiment 3

[0056] Except having made reaction temperature into 40 degreeC, the same operation as Example 1 was performed. As a result, 6.2 g of 1-adamantanol with a GC purity of 97.6% was obtained, and the yield was 92%.

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Abstract

The invention provides a method for production of adamantanol. The adamantane reacts in a mixing solution containing a fuming sulfuric acid and an organic nitrile compound and the obtained reaction solution is hydrolyzed. The adamantanol is industrially beneficially produced by the adamantane at high yield in short time without using a large amount of fuming sulfuric acid and dear carbonium ion generation compound. The adamantanol is used as the raw material of a medicine intermediate and a monomer for a photoresist, the raw material of a photochromic compound and the raw material of a coating, a cement, a binder, a film and an adsorbing material.

Description

technical field [0001] The present invention relates to an industrially advantageous method for producing adamantanols from adamantanes in a short time with high yield. Background technique [0002] The adamantanols (1-adamantanol, etc.) obtained by bonding hydroxyl groups to the adamantane skeleton have pharmaceutical intermediates, raw materials for photoresist monomers, raw materials for photochromic compounds, coatings, binders ( Adhesives), adhesives (adhesives), films, raw materials for adsorbents, etc., are used in a wide range of applications, and are industrially important compounds. [0003] As a method for producing adamantanols, a method of air-oxidizing adamantanes in the presence of a metal salt oxidation catalyst is disclosed (Patent Document 1), or a method of oxidizing adamantanes using chromium trioxide in acetic acid (Patent Document 1). Document 2). [0004] In the method using air oxidation (Patent Document 1), the selectivity of adamantanols (monohydr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/02C07C35/37C07C29/12
CPCC07C29/09C07C29/50C07C35/37
Inventor 小岛明雄高桥几子藤川伸夫
Owner OSAKA ORGANIC CHEM INDS
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