Title:
METHOD FOR PRODUCING ESTER
Document Type and Number:
WIPO Patent Application WO/2012/060185
Kind Code:
A1
Abstract:
The present invention is a method for producing ester from ketone or aldehyde that is a reactant, using hydrogen peroxide by Baeyer-Villiger oxidation reaction, wherein as a catalyst, M(BAr4)n (M is an alkali metal or an alkali-earth metal, Ar is aryl, n is the same number as the valence of M) that is a metal borate, is used. For example, when cyclohexanone is used as a reactant, and Sr[B(3,5-CF3C6H3)4]2 is used as a catalyst, ε-caprolactone is obtained in an isolated yield of 82%.
Inventors:
ISHIHARA KAZUAKI (JP)
UYANIK MUHAMMET (JP)
UYANIK MUHAMMET (JP)
Application Number:
PCT/JP2011/073340
Publication Date:
May 10, 2012
Filing Date:
October 11, 2011
Export Citation:
Assignee:
UNIV NAGOYA NAT UNIV CORP (JP)
ISHIHARA KAZUAKI (JP)
UYANIK MUHAMMET (JP)
ISHIHARA KAZUAKI (JP)
UYANIK MUHAMMET (JP)
International Classes:
C07C67/42; C07C69/24; C07D307/33; C07D307/77; C07D307/79; C07D309/30; C07D313/04; C07B61/00
Foreign References:
| JP2004352636A | 2004-12-16 | |||
| JPH09104681A | 1997-04-22 | |||
| JP2003190804A | 2003-07-08 | |||
| JP2010245944A | 2010-10-28 |
Other References:
NEIMANN K. ET AL.: "Electrophilic Activation of Hydrogen Peroxide: Selective Oxidation Reactions in Perfluorinated Alcohol Solvents", ORGANIC LETTERS, vol. 2, no. 18, 2000, pages 2861 - 2863, XP008116670
FUJIKI K. ET AL.: "Evaluation of Lewis Acidity of "Naked" Lithium Ion through Diels-Alder Reaction Catalyzed by Lithium TFPB in Nonpolar Organic Solvents", CHEMISTRY LETTERS, vol. 29, 2000, pages 62 - 63, XP009097713
LIAO B.-S. ET AL.: "An Efficient Preparation of Bis(indole)methanes Catalyzed by Tetrakis [3,5-bis(trifluoromethyl)phenyl]borate Salts in Aqueous Medium", SYNTHESIS, no. 20, 2007, pages 3125 - 3128, XP055085511
DAISUKE NAKAJIMA ET AL.: "Alcali-Alcali Dorui Kinzoku no Kasadakai Borate-en Shokubai to Kasanka Suiso ni yoru Baeyer-Villiger Sanka Hanno", 91ST ANNUAL MEETING OF THE CHEMICAL SOCIETY OF JAPAN, 11 March 2011 (2011-03-11), KOEN YOKOSHU, pages 1221, XP008168374
DAISUKE NAKAJIMA ET AL.: "Kasanka Suisosui o Sankazai ni Mochiiru Kankyo Chowagata Shokubaiteki Baeyer-Villiger Sanka Hanno", DAI 41 KAI ANNUAL MEETING OF UNION OF CHEMISTRY- RELATED SOCIETIES IN CHUBU AREA, 6 November 2010 (2010-11-06), JAPAN KOEN, pages 199, XP008169387
ORGANIC LETTERS, vol. 2, 2000, pages 2861
TETRAHEDRON LETTERS, vol. 42, 2001, pages 2293
ANGEW. CHEM. INT. ED., vol. 41, 2002, pages 4481
J. ORG. CHEM., vol. 66, 2001, pages 2429
TETRAHEDRON LETTERS, vol. 46, 2005, pages 8665
GREEN CHEM., vol. 5, 2003, pages 524
J. MOL. CATAL. A:CHEM., vol. 191, 2003, pages 93
TETRAHEDRON, vol. 63, 2007, pages 1435
APP. CATAL.B: ENVIRON., vol. 72, 2007, pages 18
CATAL. LETT., vol. 131, 2009, pages 618
ORGANOMET., vol. 11, 1992, pages 3920
HUDRLIK ET AL., J. AM. CHEM. SOC., vol. 102, 1980, pages 6894
KOTSUKI ET AL., ORG. LETT., vol. 12, 2010, pages 1616
See also references of EP 2636665A4
FUJIKI K. ET AL.: "Evaluation of Lewis Acidity of "Naked" Lithium Ion through Diels-Alder Reaction Catalyzed by Lithium TFPB in Nonpolar Organic Solvents", CHEMISTRY LETTERS, vol. 29, 2000, pages 62 - 63, XP009097713
LIAO B.-S. ET AL.: "An Efficient Preparation of Bis(indole)methanes Catalyzed by Tetrakis [3,5-bis(trifluoromethyl)phenyl]borate Salts in Aqueous Medium", SYNTHESIS, no. 20, 2007, pages 3125 - 3128, XP055085511
DAISUKE NAKAJIMA ET AL.: "Alcali-Alcali Dorui Kinzoku no Kasadakai Borate-en Shokubai to Kasanka Suiso ni yoru Baeyer-Villiger Sanka Hanno", 91ST ANNUAL MEETING OF THE CHEMICAL SOCIETY OF JAPAN, 11 March 2011 (2011-03-11), KOEN YOKOSHU, pages 1221, XP008168374
DAISUKE NAKAJIMA ET AL.: "Kasanka Suisosui o Sankazai ni Mochiiru Kankyo Chowagata Shokubaiteki Baeyer-Villiger Sanka Hanno", DAI 41 KAI ANNUAL MEETING OF UNION OF CHEMISTRY- RELATED SOCIETIES IN CHUBU AREA, 6 November 2010 (2010-11-06), JAPAN KOEN, pages 199, XP008169387
ORGANIC LETTERS, vol. 2, 2000, pages 2861
TETRAHEDRON LETTERS, vol. 42, 2001, pages 2293
ANGEW. CHEM. INT. ED., vol. 41, 2002, pages 4481
J. ORG. CHEM., vol. 66, 2001, pages 2429
TETRAHEDRON LETTERS, vol. 46, 2005, pages 8665
GREEN CHEM., vol. 5, 2003, pages 524
J. MOL. CATAL. A:CHEM., vol. 191, 2003, pages 93
TETRAHEDRON, vol. 63, 2007, pages 1435
APP. CATAL.B: ENVIRON., vol. 72, 2007, pages 18
CATAL. LETT., vol. 131, 2009, pages 618
ORGANOMET., vol. 11, 1992, pages 3920
HUDRLIK ET AL., J. AM. CHEM. SOC., vol. 102, 1980, pages 6894
KOTSUKI ET AL., ORG. LETT., vol. 12, 2010, pages 1616
See also references of EP 2636665A4
Attorney, Agent or Firm:
ITEC INTERNATIONAL PATENT FIRM (JP)
Patent business corporation Itec international patent firm (JP)
Patent business corporation Itec international patent firm (JP)
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