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
  • [41] Epoxidation of soybean oil using a homogeneous catalytic system based on a molybdenum (VI) complex
    Farias, Maritana
    Martinelli, Marcia
    Bottega, Diana Pagliocchi
    [J]. APPLIED CATALYSIS A-GENERAL, 2010, 384 (1-2) : 213 - 219
  • [42] METHYL-ESTERS IN THE FATTY-ACID INDUSTRY
    FARRIS, RD
    [J]. JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1979, 56 : A770 - A773
  • [43] Synthetic Transformations for the Valorization of Fatty Acid Derivatives
    Fraile, Jose M.
    Garcia, Jose I.
    Herrerias, Clara I.
    Pires, Elisabet
    [J]. SYNTHESIS-STUTTGART, 2017, 49 (07): : 1444 - 1460
  • [44] Epoxy Methyl Soyate as Bio-Plasticizer: Two Different Preparation Strategies
    Galli, Federico
    Nucci, Stefano
    Pirola, Carlo
    Bianchi, Claudia L.
    [J]. ICONBM: INTERNATIONAL CONFERENCE ON BIOMASS, PTS 1 AND 2, 2014, 37 : 601 - 606
  • [45] DRS UV-VIS AND EPR SPECTROSCOPY OF HYDROPEROXO AND SUPEROXO COMPLEXES IN TITANIUM SILICALITE
    GEOBALDO, F
    BORDIGA, S
    ZECCHINA, A
    GIAMELLO, E
    LEOFANTI, G
    PETRINI, G
    [J]. CATALYSIS LETTERS, 1992, 16 (1-2) : 109 - 115
  • [46] Epoxidation of soybean oil by the methyltrioxorhenium-CH2Cl2/H2O2 catalytic biphasic system
    Gerbase, AE
    Gregório, JR
    Martinelli, M
    Brasil, MC
    Mendes, ANF
    [J]. JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 2002, 79 (02) : 179 - 181
  • [47] Epoxidation of karanja (Pongamia glabra) oil by H2O2
    Goud, Vaibhav V.
    Pradhan, Narayan C.
    Patwardhan, Anand V.
    [J]. JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 2006, 83 (07) : 635 - 640
  • [48] Studies on the epoxidation of mahua oil (Madhumica indica) by hydrogen peroxide
    Goud, Vaibhav V.
    Patwardhan, Anand V.
    Pradhan, Narayan C.
    [J]. BIORESOURCE TECHNOLOGY, 2006, 97 (12) : 1365 - 1371
  • [49] The crystal structures of [NMe(4)][(Me(2)AsO(2)){MoO(O-2)(2)}(2)], [NMe4][(Ph(2)PO(2)){MoO(O-2)(2)}(2)], [NBu(4)(n)][(Ph(2)PO(2)){WO(O-2)(2)}(2)] and [NH4][(Ph(2)PO(2)){MoO(O-2)(2)(H2O)}] and their use as catalytic oxidants
    Gresley, NM
    Griffith, WP
    Parkin, BC
    White, AJP
    Williams, DJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1996, (10): : 2039 - 2045
  • [50] Epoxidation of unsaturated FAMEs obtained from vegetable source over Ti(IV)-grafted silica catalysts: A comparison between ordered and non-ordered mesoporous materials
    Guidotti, M
    Ravasio, N
    Psaro, R
    Gianotti, E
    Coluccia, S
    Marchese, L
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 250 (1-2) : 218 - 225