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Method of producing diol, polydiol, secondary alcohol or diketone compound

外国特許コード F110003721
整理番号 BE06006WO
掲載日 2011年7月4日
出願国 欧州特許庁(EPO)
出願番号 07828841
公報番号 2067761
公報番号 2067761
出願日 平成19年9月28日(2007.9.28)
公報発行日 平成21年6月10日(2009.6.10)
公報発行日 平成27年7月8日(2015.7.8)
国際出願番号 JP2007069100
国際公開番号 WO2008038801
国際出願日 平成19年9月28日(2007.9.28)
国際公開日 平成20年4月3日(2008.4.3)
優先権データ
  • 2007JP069100 (2007.9.28) WO
  • 特願2006-268796 (2006.9.29) JP
  • 特願2007-056820 (2007.3.7) JP
発明の名称 (英語) Method of producing diol, polydiol, secondary alcohol or diketone compound
発明の概要(英語) The invention is a process of using, as a reducing agent, a 12CaO·7Al 2 O 3 electride containing electrons in a number of 10 19 cm -3 or more and 2.3 × 10 21 cm -3 or less in its cages to subject a carbonyl compound to reductive coupling in a solvent, thereby synthesizing a diol or polydiol.
The invention is also a process of reducing a ketone compound in a solvent, thereby synthesizing a secondary alcohol or diketone compound.
According to the process of the invention, it is possible to synthesize a diol or polydiol, or a secondary alcohol or diketone compound through simple operations in a short period without using an expensive and harmful metal hydride or metal salt nor limiting the atmosphere for the synthesis to an inert gas atmosphere as in conventional processes.
特許請求の範囲(英語) [claim1]
1. A process for producing a diol or polydiol by reductive coupling reaction of a carbonyl compound in a reaction solution, comprising: forming the reaction solution by mixing the carbonyl compound and a 12CaO.7Al 2O 3 electride containing electrons in a number of 10 **19 cm **-3 or more and 2.3 X 10 **21 cm **-3 or less in its cages in water, an organic solvent, or a mixed solvent of water and an organic solvent, wherein about the use amount of the 12CaO.7Al 2O 3 electride relative to the carbonyl compound (12CaO.7Al 2O 3/the carbonyl compound), the ratio by weight of the former to the latter is from 2 to 20, and extracting a product from the reaction solution.
[claim2]
2. The process for producing a diol or polydiol according to claim 1, wherein the carbonyl compound is a compound wherein at least one out of two substituents bonded to a carbonyl group is an aryl group.
[claim3]
3. The process for producing a diol or polydiol according to claim 1, wherein the carbonyl compound is represented by the following general formula: (see diagramm) wherein R **1 is a functional group selected from a hydrogen atom, an alkyl group and an aryl group, R **2, R **3, R **4, R **5 and R **6 are each a functional group, bonded to the aryl group, selected from a hydrogen atom, a chloro radical, a bromo radical, a iodo radical, an alkyl group, an aryl group, a carbonyl group, an allyl group, a vinyl group, an amino group, a hydroxy group, an alkoxy group, a nitro group, a cyano group, and an imino group, and R **1 and the aryl group may be bonded to each other to form a ring structure.
[claim4]
4. The process for producing a diol or polydiol according to claim 1, wherein a reaction atmosphere for the reductive coupling is the inside of air.
[claim5]
5. A process for producing a secondary alcohol by reductive reaction of a ketone compound in a reaction solution, comprising: forming the reaction solution by mixing the ketone compound represented by compound 1 in the following reaction equation 1 and a 12CaO.7Al 2O 3 electride containing electrons in a number of 10 **19 cm **-3 or more and 2.3 X 10 **21 cm **-3 or less in its cages in water, an organic solvent, or a mixed solvent of water and an organic solvent, wherein about the use amount of the 12CaO.7Al 2O 3 electride relative to the ketone compound (12CaO.7Al 2O 3/the ketone compound), the ratio by weight of the former to the latter is from 2 to 20, and extracting a product from the reaction solution, thereby synthesizing the secondary alcohol which is a secondary alcohol represented by compound 2 in the reaction equation 1: (see diagramm) wherein R and R **1 are each a functional group selected from an aryl group and an alkyl group, and at least one of R and R **1 contains an aryl group.
[claim6]
6. The process for producing a secondary alcohol according to claim 5, wherein R and R **1 are each at least one selected from a methyl group, a phenyl group, a phenylcyano group, or a phenylmethoxy group, except that R and R **1 are simultaneously methyl groups.
[claim7]
7. The process for producing a secondary alcohol according to claim 5, wherein the organic solvent, or the organic solvent of the mixed solvent is dioxane.
[claim8]
8. The process for producing a secondary alcohol according to claim 5, wherein an atmosphere for the reaction is the inside of the air.
[claim9]
9. A process for producing a dianthrone by dimerization of an arylketone compound in a reaction solution, comprising;
forming the reaction solution by mixing the arylketone compound (anthrone) represented by compound 3 in the following reaction equation 2 and a 12CaO.7Al 2O 3 electride containing electrons in a number of 10 **19 cm **-3 or more and 2.3 X 10 **21 cm **-3 or less in its cages in a mixed solvent of water and an organic solvent,
wherein about the use amount of the 12CaO.7Al 2O 3 electride relative to the ketone compound (12CaO.7Al 2O 3/the ketone compound), the ratio by weight of the former to the latter is from 2 to 20, and
extracting a product from the reaction solution,
thereby synthesizing the dianthrone which is a dianthrone represented by compound 4 in the reaction equation 2: (see diagramm)
[claim10]
10. The process for producing a dianthrone according to claim 9, wherein the organic solvent is selected from CH 3CN, Et-OH, t-Bu-OH, or dioxane.
[claim11]
11. The process for producing a dianthrone according to claim 9, wherein an atmosphere for the reaction is the inside of an inert gas.
[claim12]
12. A process for producing a dichalcone mixture by dimerizing a ketone compound in a reaction solution, comprising;
forming the reaction solution by mixing the ketone compound (chalcone) represented by compound 5 in the following reaction equation 3 , which contains a carbon double bond, and a 12CaO.7Al 2O 3 electride containing electrons in a number of 10 **19 cm **-3 or more and 2.3 X 10 **21 cm **-3 or less in its cages in a mixed solvent of water and an organic solvent, wherein about the use amount of the 12CaO.7Al 2O 3 electride relative to the ketone compound (12CaO.7Al 2O 3/the ketone compound), the ratio by weight of the former to the latter is from 2 to 20, and
extracting a product from the reaction solution,
thereby synthesizing dichalcones represented by compound 6 and compound 7 in the reaction equation 3: (see diagramm)
[claim13]
13. The process for producing a dichalcone according to claim 12, wherein the organic solvent is tetrahydrofuran (THF).
  • 出願人(英語)
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
  • 発明者(英語)
  • HOSONO HIDEO
  • BUCHAMMAGARI HARITHA
  • TODA YOSHITAKE
  • HIRANO MASAHIRO
  • OSAKADA KOHTARO
  • TAKEUCHI DAISUKE
国際特許分類(IPC)
欧州特許分類/主・副
  • C07B041/02
  • C07C029/143
  • C07C029/38
  • C07C041/26
  • C07C041/30
  • C07C045/72
  • C07C045/73
  • C07C046/00
  • C07C253/30
指定国 Contracting States: DE FR GB
参考情報 (研究プロジェクト等) ERATO/SORST Exploring and developing applications for active functions utilizing nanostructure embedded in transparent oxides AREA
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