An efficient reaction protocol for the ruthenium-catalysed epoxidation of methyl oleate
The transition metal catalysed epoxidation of methyl oleate 1 by hydrogen peroxide was investigated using Ru(acac)3/dipicolinic acid as catalyst. Under optimised reaction conditions, the epoxidised methyl oleate 2 was obtained with a quantitative yield in short reaction time and under mild reaction...
Gespeichert in:
| Veröffentlicht in: | European journal of lipid science and technology 2012-08, Vol.114 (8), p.905-910 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 910 |
|---|---|
| container_issue | 8 |
| container_start_page | 905 |
| container_title | European journal of lipid science and technology |
| container_volume | 114 |
| creator | Behr, Arno Tenhumberg, Nils Wintzer, Andreas |
| description | The transition metal catalysed epoxidation of methyl oleate 1 by hydrogen peroxide was investigated using Ru(acac)3/dipicolinic acid as catalyst. Under optimised reaction conditions, the epoxidised methyl oleate 2 was obtained with a quantitative yield in short reaction time and under mild reaction conditions.
Practical applications: Epoxidised fatty acids and their derivatives are produced by the Prilezhaev reaction and used in various applications in the chemical industry. Due to the known drawbacks of epoxidation with peroxy acids, such as hazardous handling of peracids in large quantities or the decrease of epoxide selectivity due to the formation of undesired by‐products in the acidic medium, the epoxidation of fatty acid derivatives using more convenient oxidants is still a subject of research interest. Herein, we present a simple procedure for the transition metal catalysed epoxidation of methyl oleate 1 by hydrogen peroxide in quantitative yields, and under mild reaction conditions, as a potential alternative for the production of epoxidised fatty acid derivatives.
Epoxidation of methyl oleate. |
| doi_str_mv | 10.1002/ejlt.201200036 |
| format | Article |
| fullrecord | <record><control><sourceid>istex_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1002_ejlt_201200036</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>ark_67375_WNG_XWJ7G8NK_G</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3576-1498b1c168ab15e51c4b4bfe60fc7b28fd0055de63368f32a87392fb6110043b3</originalsourceid><addsrcrecordid>eNqFkDFPwzAQhSMEEqWwMnthTLHjxEnGqiqBUpWlqGyW45xVlzSObCOaf09KqoqN5e6G973Te0FwT_CEYBw9wq72kwiTCGNM2UUwIjHNwpyS6PJ0pyxPr4Mb53a9JGcMj4LNtEGglJYaGo8sCOm1aVBrjTfS1EgZi_wWkP3qZ6O_9qEUXtSdgwpBaw66Er-AUWgPftvVyNQgPNwGV0rUDu5Oexy8P83Xs-dw-Va8zKbLUNIkZSGJ86wkkrBMlCSBhMi4jEsFDCuZllGmKoyTpAJGKcsUjUSW0jxSJSN95JiWdBxMBl9pjXMWFG-t3gvbcYL5sRZ-rIWfa-mBhwFohZOiVlY0UrszFTEaE5oddfmg-9Y1dP-48vliuf77IxxY7Twczqywn5ylNE34ZlXwj80iLbLVKy_oDyerhAw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>An efficient reaction protocol for the ruthenium-catalysed epoxidation of methyl oleate</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Behr, Arno ; Tenhumberg, Nils ; Wintzer, Andreas</creator><creatorcontrib>Behr, Arno ; Tenhumberg, Nils ; Wintzer, Andreas</creatorcontrib><description>The transition metal catalysed epoxidation of methyl oleate 1 by hydrogen peroxide was investigated using Ru(acac)3/dipicolinic acid as catalyst. Under optimised reaction conditions, the epoxidised methyl oleate 2 was obtained with a quantitative yield in short reaction time and under mild reaction conditions.
Practical applications: Epoxidised fatty acids and their derivatives are produced by the Prilezhaev reaction and used in various applications in the chemical industry. Due to the known drawbacks of epoxidation with peroxy acids, such as hazardous handling of peracids in large quantities or the decrease of epoxide selectivity due to the formation of undesired by‐products in the acidic medium, the epoxidation of fatty acid derivatives using more convenient oxidants is still a subject of research interest. Herein, we present a simple procedure for the transition metal catalysed epoxidation of methyl oleate 1 by hydrogen peroxide in quantitative yields, and under mild reaction conditions, as a potential alternative for the production of epoxidised fatty acid derivatives.
Epoxidation of methyl oleate.</description><identifier>ISSN: 1438-7697</identifier><identifier>EISSN: 1438-9312</identifier><identifier>DOI: 10.1002/ejlt.201200036</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Biological and medical sciences ; Epoxidation ; Fat industries ; Food industries ; Fundamental and applied biological sciences. Psychology ; Homogeneous catalysis ; Hydrogen Peroxide ; Methyl oleate ; Renewable resources</subject><ispartof>European journal of lipid science and technology, 2012-08, Vol.114 (8), p.905-910</ispartof><rights>Copyright © 2012 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3576-1498b1c168ab15e51c4b4bfe60fc7b28fd0055de63368f32a87392fb6110043b3</citedby><cites>FETCH-LOGICAL-c3576-1498b1c168ab15e51c4b4bfe60fc7b28fd0055de63368f32a87392fb6110043b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejlt.201200036$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejlt.201200036$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26341386$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Behr, Arno</creatorcontrib><creatorcontrib>Tenhumberg, Nils</creatorcontrib><creatorcontrib>Wintzer, Andreas</creatorcontrib><title>An efficient reaction protocol for the ruthenium-catalysed epoxidation of methyl oleate</title><title>European journal of lipid science and technology</title><addtitle>Eur. J. Lipid Sci. Technol</addtitle><description>The transition metal catalysed epoxidation of methyl oleate 1 by hydrogen peroxide was investigated using Ru(acac)3/dipicolinic acid as catalyst. Under optimised reaction conditions, the epoxidised methyl oleate 2 was obtained with a quantitative yield in short reaction time and under mild reaction conditions.
Practical applications: Epoxidised fatty acids and their derivatives are produced by the Prilezhaev reaction and used in various applications in the chemical industry. Due to the known drawbacks of epoxidation with peroxy acids, such as hazardous handling of peracids in large quantities or the decrease of epoxide selectivity due to the formation of undesired by‐products in the acidic medium, the epoxidation of fatty acid derivatives using more convenient oxidants is still a subject of research interest. Herein, we present a simple procedure for the transition metal catalysed epoxidation of methyl oleate 1 by hydrogen peroxide in quantitative yields, and under mild reaction conditions, as a potential alternative for the production of epoxidised fatty acid derivatives.
Epoxidation of methyl oleate.</description><subject>Biological and medical sciences</subject><subject>Epoxidation</subject><subject>Fat industries</subject><subject>Food industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Homogeneous catalysis</subject><subject>Hydrogen Peroxide</subject><subject>Methyl oleate</subject><subject>Renewable resources</subject><issn>1438-7697</issn><issn>1438-9312</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqFkDFPwzAQhSMEEqWwMnthTLHjxEnGqiqBUpWlqGyW45xVlzSObCOaf09KqoqN5e6G973Te0FwT_CEYBw9wq72kwiTCGNM2UUwIjHNwpyS6PJ0pyxPr4Mb53a9JGcMj4LNtEGglJYaGo8sCOm1aVBrjTfS1EgZi_wWkP3qZ6O_9qEUXtSdgwpBaw66Er-AUWgPftvVyNQgPNwGV0rUDu5Oexy8P83Xs-dw-Va8zKbLUNIkZSGJ86wkkrBMlCSBhMi4jEsFDCuZllGmKoyTpAJGKcsUjUSW0jxSJSN95JiWdBxMBl9pjXMWFG-t3gvbcYL5sRZ-rIWfa-mBhwFohZOiVlY0UrszFTEaE5oddfmg-9Y1dP-48vliuf77IxxY7Twczqywn5ylNE34ZlXwj80iLbLVKy_oDyerhAw</recordid><startdate>201208</startdate><enddate>201208</enddate><creator>Behr, Arno</creator><creator>Tenhumberg, Nils</creator><creator>Wintzer, Andreas</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201208</creationdate><title>An efficient reaction protocol for the ruthenium-catalysed epoxidation of methyl oleate</title><author>Behr, Arno ; Tenhumberg, Nils ; Wintzer, Andreas</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3576-1498b1c168ab15e51c4b4bfe60fc7b28fd0055de63368f32a87392fb6110043b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Biological and medical sciences</topic><topic>Epoxidation</topic><topic>Fat industries</topic><topic>Food industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Homogeneous catalysis</topic><topic>Hydrogen Peroxide</topic><topic>Methyl oleate</topic><topic>Renewable resources</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Behr, Arno</creatorcontrib><creatorcontrib>Tenhumberg, Nils</creatorcontrib><creatorcontrib>Wintzer, Andreas</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>European journal of lipid science and technology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Behr, Arno</au><au>Tenhumberg, Nils</au><au>Wintzer, Andreas</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An efficient reaction protocol for the ruthenium-catalysed epoxidation of methyl oleate</atitle><jtitle>European journal of lipid science and technology</jtitle><addtitle>Eur. J. Lipid Sci. Technol</addtitle><date>2012-08</date><risdate>2012</risdate><volume>114</volume><issue>8</issue><spage>905</spage><epage>910</epage><pages>905-910</pages><issn>1438-7697</issn><eissn>1438-9312</eissn><abstract>The transition metal catalysed epoxidation of methyl oleate 1 by hydrogen peroxide was investigated using Ru(acac)3/dipicolinic acid as catalyst. Under optimised reaction conditions, the epoxidised methyl oleate 2 was obtained with a quantitative yield in short reaction time and under mild reaction conditions.
Practical applications: Epoxidised fatty acids and their derivatives are produced by the Prilezhaev reaction and used in various applications in the chemical industry. Due to the known drawbacks of epoxidation with peroxy acids, such as hazardous handling of peracids in large quantities or the decrease of epoxide selectivity due to the formation of undesired by‐products in the acidic medium, the epoxidation of fatty acid derivatives using more convenient oxidants is still a subject of research interest. Herein, we present a simple procedure for the transition metal catalysed epoxidation of methyl oleate 1 by hydrogen peroxide in quantitative yields, and under mild reaction conditions, as a potential alternative for the production of epoxidised fatty acid derivatives.
Epoxidation of methyl oleate.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejlt.201200036</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1438-7697 |
| ispartof | European journal of lipid science and technology, 2012-08, Vol.114 (8), p.905-910 |
| issn | 1438-7697 1438-9312 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_ejlt_201200036 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Biological and medical sciences Epoxidation Fat industries Food industries Fundamental and applied biological sciences. Psychology Homogeneous catalysis Hydrogen Peroxide Methyl oleate Renewable resources |
| title | An efficient reaction protocol for the ruthenium-catalysed epoxidation of methyl oleate |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-21T15%3A04%3A07IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-istex_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=An%20efficient%20reaction%20protocol%20for%20the%20ruthenium-catalysed%20epoxidation%20of%20methyl%20oleate&rft.jtitle=European%20journal%20of%20lipid%20science%20and%20technology&rft.au=Behr,%20Arno&rft.date=2012-08&rft.volume=114&rft.issue=8&rft.spage=905&rft.epage=910&rft.pages=905-910&rft.issn=1438-7697&rft.eissn=1438-9312&rft_id=info:doi/10.1002/ejlt.201200036&rft_dat=%3Cistex_cross%3Eark_67375_WNG_XWJ7G8NK_G%3C/istex_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |