Title:
CYCLIC COMPOUND AND METHOD FOR PRODUCING CYCLIC COMPOUND
Document Type and Number:
WIPO Patent Application WO/2023/090298
Kind Code:
A1
Abstract:
One embodiment of the method for producing a cyclic compound of the present invention is characterized by having a step for obtaining a cyclic compound by applying, to a starting material containing a cyclic carboxylic acid compound, a heat treatment for heating in the presence of a catalyst, thereby causing a decarboxylation reaction in the cyclic carboxylic acid compound, the catalyst containing zeolite composed of an aluminum/silicon-containing composite oxide, and the SiO2/Al2O3 ratio of the zeolite being 7-500. Another embodiment of the method for producing a cyclic compound of the present invention is characterized by having a step for obtaining a cyclic compound by applying, to a starting material containing a cyclic carboxylic acid compound, a heat treatment for heating in the presence of a non-solid acid, thereby causing a decarboxylation reaction in the cyclic carboxylic acid compound.
Inventors:
INOUE YUSUKE (JP)
MURATA RYUICHI (JP)
HASHIZUME MASAYOSHI (JP)
FUJIWARA DAISUKE (JP)
TACHIBANA KENYA (JP)
MURATA RYUICHI (JP)
HASHIZUME MASAYOSHI (JP)
FUJIWARA DAISUKE (JP)
TACHIBANA KENYA (JP)
Application Number:
PCT/JP2022/042272
Publication Date:
May 25, 2023
Filing Date:
November 14, 2022
Export Citation:
Assignee:
SUMITOMO BAKELITE CO (JP)
International Classes:
C07B59/00; B01J27/053; B01J29/08; B01J29/18; B01J29/40; B01J29/60; B01J29/65; B01J29/70; B01J31/04; C07B61/00; C07C37/50; C07C39/04; C07C39/08; C07C209/68; C07C211/46
Domestic Patent References:
| WO2016194727A1 | 2016-12-08 |
Foreign References:
| JP2016023136A | 2016-02-08 | |||
| JP2016511283A | 2016-04-14 | |||
| JPH10510544A | 1998-10-13 | |||
| JP2009532506A | 2009-09-10 |
Other References:
ZAFAR FAISAL; PARK JAEYEONG; KIM CHEOL HYUN; BAE JONG WOOK: "Contributions of acidic-basic sites on hybridized FER@g-C3N4 for liquid-phase decarboxylation of naphthenic acids", FUEL, IPC SIENCE AND TECHNOLOGY PRESS , GUILDFORD, GB, vol. 296, 26 March 2021 (2021-03-26), GB , pages 120679, XP086540391, ISSN: 0016-2361, DOI: 10.1016/j.fuel.2021.120679
YASUHIRO TAKAMURAM AKIRA NAKAMURA, AND HAREHIKO TAGUCHI: "Catalytic decarboxalation of benzoic acid", INDUSTRIAL AND ENGINEERING CHEMISTRY PRODUCT RESEARCH AND DEVELOPMENT, AMERICAN CHEMICAL SOCIETY, EASTON, PA, US, vol. 24, 1 January 1985 (1985-01-01), EASTON, PA, US , pages 213 - 215, XP009122794, ISSN: 0536-1079, DOI: 10.1021/i300018a007
FU XIAOQIN, DAI ZHENYU, TIAN SONGBAI, LONG JUN, HOU SUANDI, WANG XIEQING: "Catalytic Decarboxylation of Petroleum Acids from High Acid Crude Oils over Solid Acid Catalysts", ENERGY & FUELS, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US., vol. 22, no. 3, 1 May 2008 (2008-05-01), WASHINGTON, DC, US. , pages 1923 - 1929, XP093067084, ISSN: 0887-0624, DOI: 10.1021/ef7006547
ASIKIN-MIJAN N.; LEE H.V.; TAUFIQ-YAP Y.H.; ABDULKREM-ALSULTAN G.; MASTULI M.S.; ONG HWAI CHYUAN: "Optimization study of SiO2-Al2O3supported bifunctional acid–base NiO-CaO for renewable fuel production using response surface methodology", ENERGY CONVERSION AND MANAGEMENT, ELSEVIER SCIENCE PUBLISHERS, OXFORD., GB, vol. 141, 17 September 2016 (2016-09-17), GB , pages 325 - 338, XP029977783, ISSN: 0196-8904, DOI: 10.1016/j.enconman.2016.09.041
ARROYO MARTA, BRIONES LAURA, HERNANDO HÉCTOR, ESCOLA JOSÉ M., SERRANO DAVID P.: "Selective Decarboxylation of Fatty Acids Catalyzed by Pd-Supported Hierarchical ZSM-5 Zeolite", ENERGY & FUELS, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US., vol. 35, no. 21, 4 November 2021 (2021-11-04), WASHINGTON, DC, US. , pages 17167 - 17181, XP093067092, ISSN: 0887-0624, DOI: 10.1021/acs.energyfuels.1c01373
TAKAHASH TAKESHIGE, LIU XING YUN: "Effect of Si/Al ratio on catalytic activity of ZSM-5 zeolite", KAGOSHIMA UNIVERSITY ENGINEERING DEPARTMENT TECHNICAL REPORT, vol. 26, 1 January 1984 (1984-01-01), pages 119 - 124, XP093067093
MEASUREMENT OF SOLID ACID PROPERTIES BY AMMONIA TEMPERATURE-PROGRAMMED DESORPTION METHOD, CATALYST, vol. 42, 2000, pages 218
MEASUREMENT OF SOLID ACID PROPERTIES BY AMMONIA TEMPERATURE-PROGRAMMED DESORPTION METHOD, SOLID ACID, vol. 42, 2000, pages 218
BIOTECHNOLOGY AND BIOENGINEERING, vol. 76, 2001
YASUHIRO TAKAMURAM AKIRA NAKAMURA, AND HAREHIKO TAGUCHI: "Catalytic decarboxalation of benzoic acid", INDUSTRIAL AND ENGINEERING CHEMISTRY PRODUCT RESEARCH AND DEVELOPMENT, AMERICAN CHEMICAL SOCIETY, EASTON, PA, US, vol. 24, 1 January 1985 (1985-01-01), EASTON, PA, US , pages 213 - 215, XP009122794, ISSN: 0536-1079, DOI: 10.1021/i300018a007
FU XIAOQIN, DAI ZHENYU, TIAN SONGBAI, LONG JUN, HOU SUANDI, WANG XIEQING: "Catalytic Decarboxylation of Petroleum Acids from High Acid Crude Oils over Solid Acid Catalysts", ENERGY & FUELS, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US., vol. 22, no. 3, 1 May 2008 (2008-05-01), WASHINGTON, DC, US. , pages 1923 - 1929, XP093067084, ISSN: 0887-0624, DOI: 10.1021/ef7006547
ASIKIN-MIJAN N.; LEE H.V.; TAUFIQ-YAP Y.H.; ABDULKREM-ALSULTAN G.; MASTULI M.S.; ONG HWAI CHYUAN: "Optimization study of SiO2-Al2O3supported bifunctional acid–base NiO-CaO for renewable fuel production using response surface methodology", ENERGY CONVERSION AND MANAGEMENT, ELSEVIER SCIENCE PUBLISHERS, OXFORD., GB, vol. 141, 17 September 2016 (2016-09-17), GB , pages 325 - 338, XP029977783, ISSN: 0196-8904, DOI: 10.1016/j.enconman.2016.09.041
ARROYO MARTA, BRIONES LAURA, HERNANDO HÉCTOR, ESCOLA JOSÉ M., SERRANO DAVID P.: "Selective Decarboxylation of Fatty Acids Catalyzed by Pd-Supported Hierarchical ZSM-5 Zeolite", ENERGY & FUELS, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US., vol. 35, no. 21, 4 November 2021 (2021-11-04), WASHINGTON, DC, US. , pages 17167 - 17181, XP093067092, ISSN: 0887-0624, DOI: 10.1021/acs.energyfuels.1c01373
TAKAHASH TAKESHIGE, LIU XING YUN: "Effect of Si/Al ratio on catalytic activity of ZSM-5 zeolite", KAGOSHIMA UNIVERSITY ENGINEERING DEPARTMENT TECHNICAL REPORT, vol. 26, 1 January 1984 (1984-01-01), pages 119 - 124, XP093067093
MEASUREMENT OF SOLID ACID PROPERTIES BY AMMONIA TEMPERATURE-PROGRAMMED DESORPTION METHOD, CATALYST, vol. 42, 2000, pages 218
MEASUREMENT OF SOLID ACID PROPERTIES BY AMMONIA TEMPERATURE-PROGRAMMED DESORPTION METHOD, SOLID ACID, vol. 42, 2000, pages 218
BIOTECHNOLOGY AND BIOENGINEERING, vol. 76, 2001
Attorney, Agent or Firm:
MASUDA, Tatsuya et al. (JP)
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