Oxidation of unsaturated fatty acid derivatives and vegetable oils

The present review reports the current literature of the last 10 years on selective oxidation reactions of fatty acid derivatives and vegetable oils. The work is structured in divisions including epoxidation, radical oxidations, Wacker-type oxidation, dihydroxylation and C=C double bond cleavage.

[1]  W. Ming,et al.  Oxidative drying of alkyd paints catalysed by a dinuclear manganese complex (MnMeTACN) , 2005 .

[2]  Kazuhiko Sato,et al.  Catalytic dihydroxylation of olefins with hydrogen peroxide: an organic-solvent- and metal-free system. , 2003, Angewandte Chemie.

[3]  W. Friedt,et al.  New Syntheses with Oils and Fats as Renewable Raw Materials for the Chemical Industry. , 2000, Angewandte Chemie.

[4]  J. Espenson,et al.  Kinetic study of epoxidations by urea–hydrogen peroxide catalyzed by methyltrioxorhenium(VII) on niobia , 2004 .

[5]  B. Borhan,et al.  Osmium tetroxide-promoted catalytic oxidative cleavage of olefins: an organometallic ozonolysis. , 2002, Journal of the American Chemical Society.

[6]  W. Ming,et al.  Oxidation of model compound emulsions for alkyd paints under the influence of cobalt drier , 2003 .

[7]  U. Schuchardt,et al.  Alumina-catalyzed epoxidation of unsaturated fatty esters with hydrogen peroxide , 2007 .

[8]  A. Poulos,et al.  Oxidation of oxa and thia fatty acids and related compounds catalysed by 5- and 15-lipoxygenase. , 2001, Bioorganic & medicinal chemistry.

[9]  V. Goud,et al.  Epoxidation of karanja (Pongamia glabra) oil catalysed by acidic ion exchange resin , 2007 .

[10]  G. Du,et al.  Catalytic epoxidation of methyl linoleate , 2004 .

[11]  H. Noureddini,et al.  Liquid-phase catalytic oxidation of unsaturated fatty acids , 1999 .

[12]  R. Grau,et al.  Kinetic of liquid-phase reactions catalyzed by acidic resins: the formation of peracetic acid for vegetable oil epoxidation , 2000 .

[13]  T. Foglia,et al.  Selective oxidations of methyl ricinoleate: Diastereoselective epoxidation with titaniumIV catalysts , 1998 .

[14]  W. Ming,et al.  Oxidation and oligomerization of ethyl linoleate under the influence of the combination of ascorbic acid 6-palmitate/iron-2-ethylhexanoate , 2006 .

[15]  B. Mattiasson,et al.  Chemo-enzymatic epoxidation of oleic acid and methyl oleate in solvent-free medium , 2005 .

[16]  J. Hubert,et al.  Mechanistic study of drying of alkyd resins using (Z,Z)- and (E,E)-3,6-nonadiene as model substances , 1997 .

[17]  M. Nielen,et al.  Crosslink mechanisms of high-solids alkyd resins in the presence of reactive diluents , 2000 .

[18]  M. Novak,et al.  Soybean lipoxygenase-mediated oxygenation of monounsaturated fatty acids to enones. , 2001, Journal of the American Chemical Society.

[19]  J. Mieloszynski,et al.  Ruthenium catalysed oxidation without CCl4 of oleic acid, other monoenic fatty acids and alkenes , 2005 .

[20]  陈倩,et al.  Lipase catalyzed synthesis of epoxy-fatty acids , 2010 .

[21]  G. D. Yadav,et al.  A kinetic model for the enzyme-catalyzed self-epoxidation of oleic acid , 2001 .

[22]  A. Behr,et al.  Katalytische Prozesse bei der Wertstoffgewinnung aus natürlichen Ölen und Fetten , 2006 .

[23]  T. Foglia,et al.  Epoxidation of fatty acids, fatty methyl esters, and alkenes by immobilized oat seed peroxygenase , 2003 .

[24]  T. Kuo,et al.  Biocatalytic production of 10-hydroxystearic acid, 10-ketostearic acid, and their primary fatty amides , 2006 .

[25]  L. J. Wright,et al.  Oleic Acid Oxidation Using Hydrogen Peroxide in Conjunction with Transition Metal Catalysis , 1998 .

[26]  N. Porter,et al.  Peroxidation of polyunsaturated fatty acid methyl esters catalyzed by N-methyl benzohydroxamic acid: a new and convenient method for selective synthesis of hydroperoxides and alcohols. , 2005, Chemical research in toxicology.

[27]  Z. P. Pai,et al.  Catalytic oxidation of olefins and alcohols with hydrogen peroxide in a two-phase system giving mono- and dicarboxylic acids , 2005 .

[28]  S. Moya,et al.  Ruthenium carbonyl complexes in catalytic epoxidation of olefins co-catalyzed by isobutyl-aldehyde , 2006 .

[29]  N. Berberova,et al.  The promoting effect of organotin compounds upon peroxidation of oleic acid , 2002 .

[30]  W. Ming,et al.  Catalytic activity of a dinuclear manganese complex (MnMeTACN) on the oxidation of ethyl linoleate , 2007 .

[31]  T. Foglia,et al.  Epoxidation of fatty acids with membrane-supported peroxygenase , 2000, Biotechnology Letters.

[32]  F. Rainone,et al.  Oxidative Cleavage of the Double Bond of Monoenic Fatty Chains in Two Steps: A New Promising Route to Azelaic Acid and Other Industrial Products , 2000 .

[33]  Avelino Corma,et al.  Synergies between bio- and oil refineries for the production of fuels from biomass. , 2007, Angewandte Chemie.

[34]  Z. Petrović,et al.  Optimization of the chemoenzymatic epoxidation of soybean oil , 2006 .

[35]  R. Hatti-Kaul,et al.  Stability of immobilized Candida antarctica lipase B during chemo-enzymatic epoxidation of fatty acids , 2007 .

[36]  Dan Yang,et al.  Design of Efficient Ketone Catalysts for Epoxidation by Using the Field Effect , 1998 .

[37]  Andreas Martin,et al.  Epoxidation of methyl oleate with molecular oxygen in the presence of aldehydes , 2008 .

[38]  Zoran S. Petrović,et al.  Epoxidation of soybean oil in toluene with peroxoacetic and peroxoformic acids — kinetics and side reactions , 2002 .

[39]  R. Höfer,et al.  Oleochemical polyols — A new raw material source for polyurethane coatings and floorings , 1997 .

[40]  Y. Jang,et al.  Effect of metal ions on the production of isomeric 9,10,13 (9,12,13)-trihydroxy-11E (10E)-octadecenoic acid from linoleic acid by Pseudomonas aeruginosa PR3 , 2002 .

[41]  W. Herrmann,et al.  Methyltrioxorhenium as Catalyst for Olefin Oxidation , 1991 .

[42]  W. Ming,et al.  The combination of ascorbic acid 6-palmitate and [Fe III 3(µ3-O)]7+ as a catalyst for the oxidation of unsaturated lipids , 2007 .

[43]  P. Knochel,et al.  Transition Metal Catalyzed Oxidations in Perfluorinated Solvents , 1997 .

[44]  T. Foglia,et al.  Hydrolysis of mono- and diepoxyoctadecanoates by alumina , 2003 .

[45]  A. Corma,et al.  Epoxidation of unsaturated fatty esters over large-poreTi-containing molecular sieves as catalysts: important role of thehydrophobic–hydrophilic properties of the molecular sieve , 1997 .

[46]  Ermanno Antonelli,et al.  Efficient Oxidative Cleavage of Olefins to Carboxylic Acids with Hydrogen Peroxide Catalyzed by Methyltrioctylammonium Tetrakis(oxodiperoxotungsto)phosphate(3-) under Two-Phase Conditions. Synthetic Aspects and Investigation of the Reaction Course. , 1998, The Journal of organic chemistry.

[47]  L. Plass,et al.  Status und Zukunft der Biotreibstoffe , 2007 .

[48]  C. R. Wilson,et al.  Transformation of Fatty Acids Catalyzed by Cytochrome P450 Monooxygenase Enzymes of Candida tropicalis , 2003, Applied and Environmental Microbiology.

[49]  W. Hoelderich,et al.  Mesoporous and amorphous Ti–silicas on the epoxidation of vegetable oils , 2005 .

[50]  T. Foglia,et al.  One-pot synthesis of fatty acid epoxides from triacylglycerols using enzymes present in oat seeds , 2006 .

[51]  J.T.P. Derksen,et al.  Seed oils rich in linolenic acid as renewable feedstock for environment-friendly crosslinkers in powder coatings , 1999 .

[52]  H. Schäfer,et al.  Cleavage of olefinic double bonds by mediated anodic oxidation , 2003 .

[53]  H. Gardner,et al.  Production of isomeric 9,10,13 (9,12,13)-trihydroxy-11E (10E)-octadecenoic acid from linoleic acid by Pseudomonas aeruginosa PR3 , 2000, Journal of Industrial Microbiology and Biotechnology.

[54]  V. Goud,et al.  Studies on the epoxidation of mahua oil (Madhumica indica) by hydrogen peroxide. , 2006, Bioresource technology.

[55]  Biokraftstoffe – Eine Übersicht , 2007 .

[56]  R. Neumann,et al.  Alkylated polyethyleneimine/polyoxometalate synzymes as catalysts for the oxidation of hydrophobic substrates in water with hydrogen peroxide. , 2004, Journal of the American Chemical Society.

[57]  M. Nielen,et al.  Oxidative crosslinking of alkyd resins studied with mass spectrometry and NMR using model compounds , 1998 .

[58]  Samik Ghosh,et al.  Synthesis and characterization of triglyceride-based polyols and tack-free coatings via the air oxidation of soy oil , 2006 .

[59]  C. Che,et al.  Ruthenium nanoparticles supported on hydroxyapatite as an efficient and recyclable catalyst for cis-dihydroxylation and oxidative cleavage of alkenes. , 2004, Angewandte Chemie.

[60]  Bo Mattiasson,et al.  Lipase mediated simultaneous esterification and epoxidation of oleic acid for the production of alkylepoxystearates , 2007 .

[61]  Matteo Guidotti,et al.  Epoxidation of unsaturated FAMEs obtained from vegetable source over Ti(IV)-grafted silica catalysts: A comparison between ordered and non-ordered mesoporous materials , 2006 .

[62]  W. Ming,et al.  Oxidation of drying oils containing non-conjugated and conjugated double bonds catalyzed by a cobalt catalyst , 2005 .

[63]  S. Nordhoff,et al.  Nachwachsende Rohstoffe in der chemischen Industrie – Weg vom Öl? , 2007 .

[64]  Á. Guerrero,et al.  Oxydation of oleic acid to (E)-10-hydroperoxy-8-octadecenoic and (E)-10-hydroxy-8-octadecenoic acids by Pseudomonas sp. 42A2. , 1997, Biochimica et biophysica acta.

[65]  L. A. Goldblatt,et al.  Chromatographie analysis of seed oils. Fatty acid composition of castor oil , 1962 .

[66]  J. Ziółkowski,et al.  Molybdenum complex-catalysed epoxidation of unsaturated fatty acids by organic hydroperoxides , 2003 .

[67]  I. Kozhevnikov,et al.  Epoxidation of oleic acid catalyzed by peroxo phosphotungstate in a two-phase system , 1998 .

[68]  A. Corma,et al.  Chemical routes for the transformation of biomass into chemicals. , 2007, Chemical reviews.

[69]  L. Schreiber,et al.  CYP94A5, a new cytochrome P450 from Nicotiana tabacum is able to catalyze the oxidation of fatty acids to the omega-alcohol and to the corresponding diacid. , 2001, European journal of biochemistry.

[70]  S. Woodward,et al.  Practical dihydroxylation and CC cleavage of unsaturated fatty acids , 1999 .

[71]  M. Tedetti,et al.  Hydroxyl radical-induced photochemical formation of dicarboxylic acids from unsaturated fatty acid (oleic acid) in aqueous solution , 2007 .

[72]  P. Knochel,et al.  A Selenium Catalyzed Epoxidation in Perfluorinated Solvents with Hydrogen Peroxide , 1999 .

[73]  A. Corma,et al.  Direct Synthesis and Characterization of Hydrophobic Aluminum-Free Ti−Beta Zeolite , 1998 .

[74]  J. Espenson,et al.  Epoxidation reactions with urea–hydrogen peroxide catalyzed by methyltrioxorhenium(VII) on niobia , 2003 .

[75]  Shiro Kobayashi,et al.  Enzymatic synthesis and curing of biodegradable epoxide-containing polyesters from renewable resources. , 2003, Biomacromolecules.

[76]  M. C. Feiters,et al.  Mechanistic studies on the Mukaiyama epoxidation. , 2004, The Journal of organic chemistry.

[77]  W. Cheung,et al.  A silica gel-supported ruthenium complex of 1,4,7-trimethyl-1,4,7-triazacyclononane as recyclable catalyst for chemoselective oxidation of alcohols and alkenes by tert-butyl hydroperoxide. , 2002, The Journal of organic chemistry.

[78]  D. Bothe,et al.  Chemo-enzymatic epoxidation of unsaturated plant oils , 2001 .

[79]  P. Gallezot.  Metal Catalysis in the Conversion of Biosustainable Resources , 1997 .

[80]  T. Foglia,et al.  Optimizing reaction parameters for the enzymatic synthesis of epoxidized oleic acid with oat seed peroxygenase , 2001 .

[81]  C. Pavithran,et al.  Epoxidation and hydroxlation of rubber seed oil: one-pot multi-step reactions , 2005 .

[82]  J. Scala,et al.  Effect of FA composition on epoxidation kinetics of TAG , 2002 .

[83]  J. Hubert,et al.  Mechanistic study of drying of alkyd resins using ethyl linoleate as a model substance , 1994 .

[84]  M. Serio,et al.  Double bond oxidative cleavage of monoenic fatty chains , 2003 .

[85]  J. Fierro,et al.  Soybean oil epoxidation with hydrogen peroxide using an amorphous Ti/SiO2 catalyst , 2004 .

[86]  B. Mattiasson,et al.  Chemo-enzymatic epoxidation of linoleic acid : Parameters influencing the reaction , 2005 .

[87]  H. Moynihan,et al.  Asymmetric Sharpless epoxidation of 13S-hydroxy- 9Z, 11E-octadecadienoic acid (13S-HODE) , 2003 .

[88]  A. Corma,et al.  Synthesis of transportation fuels from biomass: chemistry, catalysts, and engineering. , 2006, Chemical reviews.

[89]  Dan Yang,et al.  Novel Cyclic Ketones for Catalytic Oxidation Reactions , 1998 .

[90]  T. Foglia,et al.  Preparation of fatty amide polyols via epoxidation of vegetable oil amides by oat seed peroxygenase , 2005 .

[91]  I. Hermans,et al.  Solvent‐ and Metal‐Free Ketonization of Fatty Acid Methyl Esters and Triacylglycerols with Nitrous Oxide , 2007 .

[92]  D. Murzin,et al.  Recent Progress in Synthesis of Fine and Specialty Chemicals from Wood and Other Biomass by Heterogeneous Catalytic Processes , 2007 .

[93]  T. Kuo,et al.  Conversion of Fatty Acids by Bacillus sphaericus-Like Organisms , 2002, Current Microbiology.

[94]  N. Ravasio,et al.  Heterogeneous catalytic epoxidation of fatty acid methyl esters on titanium-grafted silicas , 2003 .

[95]  G. Knothe.  Synthesis and characterization of long-chain 1,2-dioxo compounds. , 2002, Chemistry and physics of lipids.