Title:
GREEN AND EFFICIENT METHOD FOR CATALYZING BUTENE TO PREPARE EPOXYBUTANE WITH ORGANIC SMALL MOLECULES
Document Type and Number:
WIPO Patent Application WO/2022/267081
Kind Code:
A1
Abstract:
Disclosed is a green and efficient method for catalyzing butene to prepare epoxybutane with organic small molecules. The method uses butene as a raw material, an organic solvent and a catalyst are added, isobutyraldehyde is used as a co-reducing agent, oxygen is used as an oxidant, and epoxybutane is prepared at room temperature under the conditions of a reaction pressure of 0.1-4.5 MPa; the catalyst is at least one selected from among a cyclic organic nitroxide radical precursor or a compound having a structure as described in the following formula (I), (II), (III), or (IV); in the formulas, R1, R2, and R3 are independently selected from among a hydrogen atom, alkyl, cycloalkyl, aryl, heterocyclic, hydroxyl, nitro and halogen, or at least two among R2, R3, and R4 form a ring. The described process is simple, the conditions are mild, and the yield and selectivity of epoxybutane are high. Moreover, the present invention has good prospects in industrial application.
Inventors:
JI HONGBING (CN)
XUE CAN (CN)
XU DEJING (CN)
ZHOU XIANTAI (CN)
HE YAORONG (CN)
XIONG CHAO (CN)
LIANG YICHAO (CN)
XUE CAN (CN)
XU DEJING (CN)
ZHOU XIANTAI (CN)
HE YAORONG (CN)
XIONG CHAO (CN)
LIANG YICHAO (CN)
Application Number:
PCT/CN2021/103226
Publication Date:
December 29, 2022
Filing Date:
June 29, 2021
Export Citation:
Assignee:
UNIV SUN YAT SEN (CN)
International Classes:
C07D301/06; C07D303/04
Foreign References:
| CN107903164A | 2018-04-13 | |||
| CN111978274A | 2020-11-24 | |||
| CN104098532A | 2014-10-15 | |||
| CN104098531A | 2014-10-15 | |||
| CN106279069A | 2017-01-04 | |||
| CN109232510A | 2019-01-18 |
Other References:
DAI PENG-FEI, QU JIAN-PING, KANG YAN-BIAO: "Organocatalyzed Aerobic Oxidation of Aldehydes to Acids", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 21, no. 5, 1 March 2019 (2019-03-01), US , pages 1393 - 1396, XP093017235, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.9b00101
MINISCI FRANCESCO, FRANCESCO RECUPERO, ANDREA CECCHETTO, CARLO PUNTA, CRISTIAN GAMBAROTTI, FRANCESCA FONTANA, GIAN FRANCO PEDULLI: "Polar Effects in Free-Radical Reactions. A Novel Homolytic Acylation of Heteroaromatic Bases by Aerobic Oxidation of Aldehydes, Catalysed by N-Hydroxyphthalimide and Co Salts", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 40, no. 2, 11 March 2009 (2009-03-11), pages 325 - 328, XP093017233, DOI: 10.1002/jhet.5570400220
ZHOU, X. ; JI, H.: "Biomimetic kinetics and mechanism of cyclohexene epoxidation catalyzed by metalloporphyrins", CHEMICAL ENGENEERING JOURNAL, ELSEVIER, AMSTERDAM, NL, vol. 156, no. 2, 15 January 2010 (2010-01-15), AMSTERDAM, NL , pages 411 - 417, XP026827912, ISSN: 1385-8947
ZHOU XIAN-TAI, SUN MU-ZHAO, JI HONG-BING: "Highly Efficient Aerobic Oxidation of Cyclohexene Catalyzed by Iron(III) Porphyrins in Supercritical Carbon Dioxide ", ECS JOURNAL OF SOLID STATE SCIENCE AND TECHNOLOGY, vol. 9, 11 May 2020 (2020-05-11), XP093017227, DOI: 10.1149/2162-8777/ab8f38
MINISCI FRANCESCO, FRANCESCO RECUPERO, ANDREA CECCHETTO, CARLO PUNTA, CRISTIAN GAMBAROTTI, FRANCESCA FONTANA, GIAN FRANCO PEDULLI: "Polar Effects in Free-Radical Reactions. A Novel Homolytic Acylation of Heteroaromatic Bases by Aerobic Oxidation of Aldehydes, Catalysed by N-Hydroxyphthalimide and Co Salts", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 40, no. 2, 11 March 2009 (2009-03-11), pages 325 - 328, XP093017233, DOI: 10.1002/jhet.5570400220
ZHOU, X. ; JI, H.: "Biomimetic kinetics and mechanism of cyclohexene epoxidation catalyzed by metalloporphyrins", CHEMICAL ENGENEERING JOURNAL, ELSEVIER, AMSTERDAM, NL, vol. 156, no. 2, 15 January 2010 (2010-01-15), AMSTERDAM, NL , pages 411 - 417, XP026827912, ISSN: 1385-8947
ZHOU XIAN-TAI, SUN MU-ZHAO, JI HONG-BING: "Highly Efficient Aerobic Oxidation of Cyclohexene Catalyzed by Iron(III) Porphyrins in Supercritical Carbon Dioxide ", ECS JOURNAL OF SOLID STATE SCIENCE AND TECHNOLOGY, vol. 9, 11 May 2020 (2020-05-11), XP093017227, DOI: 10.1149/2162-8777/ab8f38
Attorney, Agent or Firm:
YOGO PATENT AND TRADEMARK AGENCY LIMITED COMPANY (CN)
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