Fe (6-Me-PyTACN)-catalyzed, one-pot oxidative cleavage of methyl oleate and oleic acid into carboxylic acids with H2O2 and NaIO 4
| Autor: | Spannring, Peter, Prat, Irene, Costas, Miquel, Lutz, Martin, Bruijnincx, Pieter C. A., Weckhuysen, Bert. M., Klein Gebbink, Bert, Organic Chemistry and Catalysis, Inorganic Chemistry and Catalysis, Sub Organic Chemistry and Catalysis, Sub Crystal and Structural Chemistry, Sub Inorganic Chemistry and Catalysis |
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| Přispěvatelé: | European Research Council, Ministerio de Economía y Competitividad (Espanya), Generalitat de Catalunya. Agència de Gestió d'Ajuts Universitaris i de Recerca, Ministerio de Ciencia e Innovación (Espanya), Organic Chemistry and Catalysis, Inorganic Chemistry and Catalysis, Sub Organic Chemistry and Catalysis, Sub Crystal and Structural Chemistry, Sub Inorganic Chemistry and Catalysis |
| Rok vydání: | 2014 |
| Předmět: |
CIS-DIHYDROXYLATION
DOUBLE-BOND Azelaic acid Catalitzadors 010402 general chemistry Oxidació 01 natural sciences Aldehyde Catalysis chemistry.chemical_compound Hydrolysis HYDROGEN-PEROXIDE CATALYTIC-OXIDATION Catàlisi Oxidation medicine Organic chemistry MANGANESE PORPHYRIN OLEFINS RENEWABLE RAW-MATERIALS chemistry.chemical_classification Ozonolysis Catalysts 010405 organic chemistry RUTHENIUM TETROXIDE Fatty acid 0104 chemical sciences CHEMICAL-INDUSTRY Oleic acid Sulfonate chemistry UNSATURATED FATTY-ACIDS medicine.drug |
| Zdroj: | © Catalysis Science and Technology, 2014, vol. 4, núm. 3, p. 708-716 Articles publicats (D-Q) DUGiDocs – Universitat de Girona instname Catalysis Science & Technology, 4(3), 708. Royal Society of Chemistry |
| ISSN: | 2044-4753 |
| Popis: | The first Fe-based catalytic system for the oxidative cleavage of unsaturated fatty acids and esters to carboxylic acids is reported. The system comprises [Fe(OTf)(2)(6-Me-PyTACN)] (2) (6-Me-PyTACN = 1-[(6-methyl-2-pyridyl) methyl]-4,7-dimethyl-1,4,7-triazacyclononane, OTf = trifluoromethane sulfonate anion) as the catalyst (3 mol%) either with a combination of hydrogen peroxide and NaIO4 or exclusively with NaIO4 as the oxidant, and operates at 0 degrees C or ambient temperature. Under these standard conditions (method A), methyl oleate is converted in a one-pot procedure into 50-55% of both nonanoic and azelaic acid, together with some epoxide and aldehyde intermediates as byproducts. These yields can be further improved by addition of sulfuric acid (method B) to hydrolyze the epoxide byproducts, by including a pH neutralization step and addition of more catalyst (1 mol%). Under the optimized conditions, both methyl oleate and oleic acid are converted into high yields of the corresponding carboxylic acids (80-85%). Overall, this catalytic system provides an alternative to the industrial ozonolysis of oleic acid and to catalytic Ru-and Os-based systems for the oxidative cleavage of unsaturated fatty acids and ester B.M.W. and R.J.M.K.G. acknowledge Utrecht University for financial support through its 'Focus and Massa' program. M.C. acknowledges financial support from the European Research Council (ERC-2009-StG-239910), MINECO of Spain (CTQ2012-37420-C02-01/BQU, Consolider-Ingenio CSD2010-00065) and the Catalan DIUE of the Generalitat de Catalunya (2009SGR637 and ICREA Academia Award). The X-ray diffractometer has been financed by the Netherlands Organization for Scientific Research (NWO) |
| Databáze: | OpenAIRE |
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