Recent advances in the field of selective epoxidation of vegetable oils and their derivatives: a review and perspective

被引:150
作者
Danov, S. M. [1 ]
Kazantsev, O. A. [1 ]
Esipovich, A. L. [1 ]
Belousov, A. S. [1 ]
Rogozhin, A. E. [1 ]
Kanakov, E. A. [1 ]
机构
[1] Nizhnii Novgorod State Tech Univ, Dept Chem Technol, 49 Gaidar St, Dzerzhinsk 606026, Russia
关键词
ACID METHYL-ESTERS; UNSATURATED FATTY ESTERS; PHASE-TRANSFER CATALYSIS; HYDROGEN-PEROXIDE; SOYBEAN OIL; CHEMOENZYMATIC EPOXIDATION; OXIDATIVE CLEAVAGE; TECHNOLOGICAL ASPECTS; BIODIESEL PRODUCTION; MOLECULAR-OXYGEN;
D O I
10.1039/c7cy00988g
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The present critical review reports the recent progress of the last 15 years in the selective epoxidation of vegetable oils and their derivatives, in particular unsaturated fatty acids (UFAs) and fatty acid methyl esters (FAMEs). Epoxidized vegetable oils (EVOs) have drawn much attention in recent years in the chemical industry since they are environmentally friendly, biodegradable, renewable, highly available and non- toxic. Four major types of catalysts are used to produce epoxidized fatty acid compounds: homogeneous, heterogeneous, polyoxometalates and lipases. EVOs are currently produced in industry by a homogeneous catalytic conventional epoxidation process, in which the unsaturated oils are converted with percarboxylic acids, such as peracetic or performic acid. However, this method suffers from several drawbacks such as (1) relatively low selectivity for epoxides due to oxirane ring opening, (2) corrosion problems caused by the strong acids in an oxidizing environment, etc. Thus, in view of the principles of green chemistry, the development of new catalytic systems for the selective epoxidation of vegetable oils and their derivatives is an actual task. Furthermore, in our opinion, epoxidized fatty acids and epoxidized fatty acid methyl esters can be a promising substitute for EVOs because the starting materials for their production have a lower viscosity and higher reactivity, which will significantly increase the productivity of the epoxidation process. In this work, we tried to determine the prospects of using the main catalytic methods in industry to obtain epoxidized fatty acid compounds.
引用
收藏
页码:3659 / 3675
页数:17
相关论文
共 149 条
  • [51] Heterogeneous catalytic epoxidation of fatty acid methyl esters on titanium-grafted silicas
    Guidotti, M
    Ravasio, N
    Psaro, R
    Gianotti, E
    Marchese, L
    Coluccia, S
    [J]. GREEN CHEMISTRY, 2003, 5 (04) : 421 - 424
  • [52] Guidotti M., 2007, CATALYSIS RENEWABLES, P257
  • [53] The effect of silylation on titanium-containing silica catalysts for the epoxidation of functionalised molecules
    Guidotti, Matteo
    Batonneau-Gener, Isabelle
    Gianotti, Enrica
    Marchese, Leonardo
    Mignard, Samuel
    Psaro, Rinaldo
    Sgobba, Maila
    Ravasio, Nicoletta
    [J]. MICROPOROUS AND MESOPOROUS MATERIALS, 2008, 111 (1-3) : 39 - 47
  • [54] Epoxidation of methyl oleate with hydrogen peroxide. The use of Ti-containing silica solids as efficient heterogeneous catalysts
    Guidotti, Matteo
    Gavrilova, Elena
    Galarneau, Anne
    Coq, Bernard
    Psaroa, Rinaldo
    Ravasio, Nicoletta
    [J]. GREEN CHEMISTRY, 2011, 13 (07) : 1806 - 1811
  • [55] Heterogeneous epoxidation of alkenes with H2O2 catalyzed by a recyclable organic-inorganic polyoxometalate-based framework catalyst
    Haddadi, Hedayat
    Hafshejani, Shahrbanou Moradpour
    Farsani, Mostafa Riahi
    Babahydari, Ali Kazemi
    [J]. NEW JOURNAL OF CHEMISTRY, 2015, 39 (12) : 9879 - 9885
  • [56] ENZYMATIC HYDRATION OF [EPOXIDES[3-18] - ROLE OF NUCLEOPHILIC MECHANISMS
    HANZLIK, RP
    EDELMAN, M
    MICHAELY, WJ
    SCOTT, G
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (07) : 1952 - 1955
  • [57] Epoxidation of Soybean Oil by Continuous Micro-Flow System with Continuous Separation
    He, Wei
    Fang, Zheng
    Ji, Dong
    Chen, Ketao
    Wan, Zhidong
    Li, Xin
    Gan, Haifeng
    Tang, Shigui
    Zhang, Kai
    Guo, Kai
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2013, 17 (09) : 1137 - 1141
  • [58] Chemo-enzymatic epoxidation of unsaturated plant oils
    Hilker, I
    Bothe, D
    Prüss, J
    Warnecke, HJ
    [J]. CHEMICAL ENGINEERING SCIENCE, 2001, 56 (02) : 427 - 432
  • [59] FACTORS INFLUENCING THE CATALYTIC ACTIVITY OF TITANIUM SILICALITES IN SELECTIVE OXIDATIONS
    HUYBRECHTS, DRC
    VAESEN, I
    LI, HX
    JACOBS, PA
    [J]. CATALYSIS LETTERS, 1991, 8 (2-4) : 237 - 244
  • [60] HYDROGEN-PEROXIDE OXIDATION CATALYZED BY HETEROPOLY ACIDS COMBINED WITH CETYLPYRIDINIUM CHLORIDE - EPOXIDATION OF OLEFINS AND ALLYLIC ALCOHOLS, KETONIZATION OF ALCOHOLS AND DIOLS, AND OXIDATIVE CLEAVAGE OF 1,2-DIOLS AND OLEFINS
    ISHII, Y
    YAMAWAKI, K
    URA, T
    YAMADA, H
    YOSHIDA, T
    OGAWA, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) : 3587 - 3593