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

Foreign code F110003721
File No. BE06006WO
Posted date Jul 4, 2011
Country EPO
Application number 07828841
Gazette No. 2067761
Gazette No. 2067761
Date of filing Sep 28, 2007
Gazette Date Jun 10, 2009
Gazette Date Jul 8, 2015
International application number JP2007069100
International publication number WO2008038801
Date of international filing Sep 28, 2007
Date of international publication Apr 3, 2008
Priority data
  • 2007JP069100 (Sep 28, 2007) WO
  • P2006-268796 (Sep 29, 2006) JP
  • P2007-056820 (Mar 7, 2007) JP
Title Method of producing diol, polydiol, secondary alcohol or diketone compound
Abstract 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.
Scope of claims [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).
  • Applicant
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
  • Inventor
  • HOSONO HIDEO
  • BUCHAMMAGARI HARITHA
  • TODA YOSHITAKE
  • HIRANO MASAHIRO
  • OSAKADA KOHTARO
  • TAKEUCHI DAISUKE
IPC(International Patent Classification)
Reference ( R and D project ) ERATO/SORST Exploring and developing applications for active functions utilizing nanostructure embedded in transparent oxides AREA
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