Epoxidation of microalgal biomass-derived squalene with hydrogen peroxide using solid heterogeneous tungsten-based catalyst

被引：3
作者：
Kawashima, Hidehisa [1 ,2 ,3 ]
Okuda, Yuki [2 ]
Kijima, Masashi [1 ,2 ,3 ]
Fujitani, Tadahiro [1 ,2 ,3 ]
Choi, Jun-Chul [1 ,2 ,3 ]
机构：
[1] Natl Inst Adv Ind Sci & Technol, Tsukuba Cent 5,1-1-1 Higashi, Tsukuba, Ibaraki 3058565, Japan
[2] Univ Tsukuba, Fac Pure & Appl Sci, Dept Mat Sci, 1-1-1 Tennodai, Tsukuba, Ibaraki 3058573, Japan
[3] Univ Tsukuba, Algae Biomass & Energy Syst R&D Ctr, 1-1-1 Tennodai, Tsukuba, Ibaraki 3058572, Japan
来源：
TETRAHEDRON | 2020年 / 76卷 / 16期
关键词：
Biomass; Epoxidation; Heterogeneous catalysis; Hydrogen peroxide; Peroxotungstate; SELECTIVE SYNTHESIS; OXIDATIVE CLEAVAGE; BOTRYOCOCCENE; OLEFINS; RELEASE; ALKENES;
D O I：
10.1016/j.tet.2020.131109
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Squalene structurally resembles petroleum resources, and is efficiently produced by Aurantiochytrium mangrovei, a microalga, and could be used effectively as an alternative oil resource. An efficient heterogeneous catalyst system for the epoxidation of squalene was developed, comprising the heterogeneous catalyst [N(C6H13)(4)](3)[PW4O8(O-2)(8)] for the successful epoxidation of squalene with H2O2 in t-BuOH. The addition of the tetraalkylammonium salt [N(C6H13)4]Cl, and H2O2 as the oxidant allowed quantitative epoxidation of squalene. (C) 2020 Elsevier Ltd. All rights reserved.
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页数：7
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共 35 条
  • [1] The use of 1H NMR for yield determination in the regioselective epoxidation of squalene
    Aerts, HAJ
    Sels, BFE
    Jacobs, PA
    [J]. JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 2005, 82 (06) : 409 - 413
  • [2] Enantioselective oxidation of olefins catalyzed by a chiral bishydroxamic acid complex of molybdenum
    Barlan, Allan U.
    Basak, Arindrajit
    Yamamoto, Hisashi
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (35) : 5849 - 5852
  • [3] Heterogenization of alkene epoxidation catalysts
    Buffon, R
    Schuchardt, U
    [J]. JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2003, 14 (03) : 347 - 353
  • [4] STUDIES ON POLYOXO-METALATES AND POLYPEROXO-METALATES .1. TETRAMERIC HETEROPOLYPEROXOTUNGSTATES AND HETEROPOLYPEROXOMOLYBDATES
    DENGEL, AC
    GRIFFITH, WP
    PARKIN, BC
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1993, (18): : 2683 - 2688
  • [5] Recent developments on the epoxidation of alkenes using hydrogen peroxide as an oxidant
    Grigoropoulou, G
    Clark, JH
    Elings, JA
    [J]. GREEN CHEMISTRY, 2003, 5 (01) : 1 - 7
  • [6] Unique Salt Effect on Highly Selective Synthesis of Acid-Labile Terpene and Styrene Oxides with a Tungsten/H2O2 Catalytic System under Acidic Aqueous Conditions
    Hachiya, Houjin
    Kon, Yoshihiro
    Ono, Yutaka
    Takumi, Kiyoshi
    Sasagawa, Naoki
    Ezaki, Yoichiro
    Sato, Kazuhiko
    [J]. SYNTHESIS-STUTTGART, 2012, 44 (11): : 1672 - 1678
  • [7] Squalene-hopene cyclase:: final deprotonation reaction, conformational analysis for the cyclization of (3R,S)-2,3-oxidosqualene and further evidence for the requirement of an isopropylidene moiety both for initiation of the polycyclization cascade and for the formation of the 5-membered E-ring
    Hoshino, T
    Nakano, S
    Kondo, T
    Sato, T
    Miyoshi, A
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (10) : 1456 - 1470
  • [8] Lanosterol Biosynthesis: The Critical Role of the Methyl-29 Group of 2,3-Oxidosqualene for the Correct Folding of this Substrate and for the Construction of the Five-Membered D Ring
    Hoshino, Tsutomu
    Chiba, Akifumi
    Abe, Naomi
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (41) : 13108 - 13116
  • [9] Squalene-derived flexible linkers for bioactive peptides
    Jagadish, Bhumasamudram
    Sankaranarayanan, Rajesh
    Xu, Liping
    Richards, Reyniak
    Vagner, Josef
    Hruby, Victor J.
    Gillies, Robert J.
    Mash, Eugene A.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (12) : 3310 - 3313
  • [10] JORGENSEN KA, 1989, CHEM REV, V89, P431
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