Bidirectional Conversion Between 3-Monochloro-1,2-propanediol and Glycidol in Course of the Procedure of DGF Standard Methods
NMR observation revealed that bidirectional conversion occurred between 3-monochloropropane-1,2-diol (3-MCPD) and glycidol in the course of the analytical procedure of DFG standard method C-III 18 (09), option A; 3-MCPD was partly converted to glycidol at the transesterification step, and glycidol w...
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| Veröffentlicht in: | Journal of the American Oil Chemists' Society 2011-08, Vol.88 (8), p.1143-1151 |
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| creator | Kaze, Naoki Sato, Hirofumi Yamamoto, Hiroshi Watanabe, Yomi |
| description | NMR observation revealed that bidirectional conversion occurred between 3-monochloropropane-1,2-diol (3-MCPD) and glycidol in the course of the analytical procedure of DFG standard method C-III 18 (09), option A; 3-MCPD was partly converted to glycidol at the transesterification step, and glycidol was converted partly to 3-MCPD at the derivatization step conducted at 80 °C under acidic condition in the presence of NaCl. Based on the proton numbers observed by
1
H NMR, the degrees of the conversion were estimated to be 37 and >70%, respectively. In addition, epoxide ring-opening of glycidol and its esters was found to be ca. 90% by the acid treatment described in the method, option B. Thus, it was concluded that the standard method, option A, did not correctly give the combined amount of 3-MCPD esters and glycidyl esters in oils containing glycidyl esters, and the difference of the values obtained by options A and B did not correspond to the amount of glycidyl esters, either. In addition, derivatives of 3-MCPD with phenylboronic acid were not observed by NMR at the derivatization step, although they were detected by GC-MS in the organic phase at the following extraction step. |
| doi_str_mv | 10.1007/s11746-011-1802-3 |
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1
H NMR, the degrees of the conversion were estimated to be 37 and >70%, respectively. In addition, epoxide ring-opening of glycidol and its esters was found to be ca. 90% by the acid treatment described in the method, option B. Thus, it was concluded that the standard method, option A, did not correctly give the combined amount of 3-MCPD esters and glycidyl esters in oils containing glycidyl esters, and the difference of the values obtained by options A and B did not correspond to the amount of glycidyl esters, either. In addition, derivatives of 3-MCPD with phenylboronic acid were not observed by NMR at the derivatization step, although they were detected by GC-MS in the organic phase at the following extraction step.</description><identifier>ISSN: 0003-021X</identifier><identifier>EISSN: 1558-9331</identifier><identifier>DOI: 10.1007/s11746-011-1802-3</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer-Verlag</publisher><subject>3‐Monochloropropane‐1,2‐diol (3‐MCPD) ; Agriculture ; Biological and medical sciences ; Biomaterials ; Biotechnology ; Chemistry ; Chemistry and Materials Science ; DFG standard method ; Esters ; Fat industries ; Food industries ; Food Science ; Fundamental and applied biological sciences. Psychology ; General aspects ; Glycidol ; Glycidyl ester ; Industrial Chemistry/Chemical Engineering ; Methods of analysis, processing and quality control, regulation, standards ; NaCl ; Original Paper ; Sodium chloride</subject><ispartof>Journal of the American Oil Chemists' Society, 2011-08, Vol.88 (8), p.1143-1151</ispartof><rights>AOCS 2011</rights><rights>2011 American Oil Chemists' Society (AOCS)</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4593-4557a6327e4b5d8f0a5c475f159890645601cef5efc6f7a6358b968408a89e373</citedby><cites>FETCH-LOGICAL-c4593-4557a6327e4b5d8f0a5c475f159890645601cef5efc6f7a6358b968408a89e373</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11746-011-1802-3$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11746-011-1802-3$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,41488,42557,45574,45575,51319</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24350060$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Kaze, Naoki</creatorcontrib><creatorcontrib>Sato, Hirofumi</creatorcontrib><creatorcontrib>Yamamoto, Hiroshi</creatorcontrib><creatorcontrib>Watanabe, Yomi</creatorcontrib><title>Bidirectional Conversion Between 3-Monochloro-1,2-propanediol and Glycidol in Course of the Procedure of DGF Standard Methods</title><title>Journal of the American Oil Chemists' Society</title><addtitle>J Am Oil Chem Soc</addtitle><description>NMR observation revealed that bidirectional conversion occurred between 3-monochloropropane-1,2-diol (3-MCPD) and glycidol in the course of the analytical procedure of DFG standard method C-III 18 (09), option A; 3-MCPD was partly converted to glycidol at the transesterification step, and glycidol was converted partly to 3-MCPD at the derivatization step conducted at 80 °C under acidic condition in the presence of NaCl. Based on the proton numbers observed by
1
H NMR, the degrees of the conversion were estimated to be 37 and >70%, respectively. In addition, epoxide ring-opening of glycidol and its esters was found to be ca. 90% by the acid treatment described in the method, option B. Thus, it was concluded that the standard method, option A, did not correctly give the combined amount of 3-MCPD esters and glycidyl esters in oils containing glycidyl esters, and the difference of the values obtained by options A and B did not correspond to the amount of glycidyl esters, either. In addition, derivatives of 3-MCPD with phenylboronic acid were not observed by NMR at the derivatization step, although they were detected by GC-MS in the organic phase at the following extraction step.</description><subject>3‐Monochloropropane‐1,2‐diol (3‐MCPD)</subject><subject>Agriculture</subject><subject>Biological and medical sciences</subject><subject>Biomaterials</subject><subject>Biotechnology</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>DFG standard method</subject><subject>Esters</subject><subject>Fat industries</subject><subject>Food industries</subject><subject>Food Science</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General aspects</subject><subject>Glycidol</subject><subject>Glycidyl ester</subject><subject>Industrial Chemistry/Chemical Engineering</subject><subject>Methods of analysis, processing and quality control, regulation, standards</subject><subject>NaCl</subject><subject>Original Paper</subject><subject>Sodium chloride</subject><issn>0003-021X</issn><issn>1558-9331</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>8G5</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><sourceid>GUQSH</sourceid><sourceid>M2O</sourceid><recordid>eNqFkMFrFDEYxYMouFb_AG9B8Gb0-ybJTObYrnYVWipUwVtIM1_clHGyJrOWPfi_m3WKnsRTeOH9Xl4eY88RXiNA96YgdqoVgCjQQCPkA7ZCrY3opcSHbAUAUkCDXx6zJ6XcVmlko1fs51kcYiY_xzS5ka_T9INyqYKf0XxHNHEpLtOU_HZMOQl81YhdTjs30RDTyN008M148HGoIk6V3-dCPAU-b4l_zMnTsM-_L95uzvn1XAGXB35J8zYN5Sl7FNxY6Nn9ecI-n7_7tH4vLq42H9anF8Ir3UuhtO5cK5uO1I0eTACnvep0QN2bHlqlW0BPQVPwbTg6tbnpW6PAONOT7OQJe7Hk1u7f91Rme1uL1g8Xa7peAxrdVhMuJp9TKZmC3eX4zeWDRbDHke0ysq0j2-PIVlbm5X2wK96NIbvJx_IHbJTUAC1UX7f47uJIh_8H29Or9TWiOr7QLGSp0PSV8t_q_671C2FLm1Y</recordid><startdate>201108</startdate><enddate>201108</enddate><creator>Kaze, Naoki</creator><creator>Sato, Hirofumi</creator><creator>Yamamoto, Hiroshi</creator><creator>Watanabe, Yomi</creator><general>Springer-Verlag</general><general>Springe-Verlag</general><general>Springer</general><general>Springer Nature B.V</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>4T-</scope><scope>7X2</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>88I</scope><scope>8AO</scope><scope>8FE</scope><scope>8FG</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>8G5</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>ATCPS</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>BHPHI</scope><scope>BKSAR</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>GUQSH</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>KB.</scope><scope>M0K</scope><scope>M0S</scope><scope>M1P</scope><scope>M2O</scope><scope>M2P</scope><scope>MBDVC</scope><scope>PCBAR</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope></search><sort><creationdate>201108</creationdate><title>Bidirectional Conversion Between 3-Monochloro-1,2-propanediol and Glycidol in Course of the Procedure of DGF Standard Methods</title><author>Kaze, Naoki ; Sato, Hirofumi ; Yamamoto, Hiroshi ; Watanabe, Yomi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4593-4557a6327e4b5d8f0a5c475f159890645601cef5efc6f7a6358b968408a89e373</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>3‐Monochloropropane‐1,2‐diol (3‐MCPD)</topic><topic>Agriculture</topic><topic>Biological and medical sciences</topic><topic>Biomaterials</topic><topic>Biotechnology</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>DFG standard method</topic><topic>Esters</topic><topic>Fat industries</topic><topic>Food industries</topic><topic>Food Science</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General aspects</topic><topic>Glycidol</topic><topic>Glycidyl ester</topic><topic>Industrial Chemistry/Chemical Engineering</topic><topic>Methods of analysis, processing and quality control, regulation, standards</topic><topic>NaCl</topic><topic>Original Paper</topic><topic>Sodium chloride</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kaze, Naoki</creatorcontrib><creatorcontrib>Sato, Hirofumi</creatorcontrib><creatorcontrib>Yamamoto, Hiroshi</creatorcontrib><creatorcontrib>Watanabe, Yomi</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Docstoc</collection><collection>Agricultural Science Collection</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Science Database (Alumni Edition)</collection><collection>ProQuest Pharma Collection</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Research Library (Alumni Edition)</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>Agricultural & Environmental Science Collection</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>Natural Science Collection</collection><collection>Earth, Atmospheric & Aquatic Science Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>Research Library Prep</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Materials Science Database</collection><collection>Agricultural Science Database</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Research Library</collection><collection>Science Database</collection><collection>Research Library (Corporate)</collection><collection>Earth, Atmospheric & Aquatic Science Database</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central Basic</collection><jtitle>Journal of the American Oil Chemists' Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kaze, Naoki</au><au>Sato, Hirofumi</au><au>Yamamoto, Hiroshi</au><au>Watanabe, Yomi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Bidirectional Conversion Between 3-Monochloro-1,2-propanediol and Glycidol in Course of the Procedure of DGF Standard Methods</atitle><jtitle>Journal of the American Oil Chemists' Society</jtitle><stitle>J Am Oil Chem Soc</stitle><date>2011-08</date><risdate>2011</risdate><volume>88</volume><issue>8</issue><spage>1143</spage><epage>1151</epage><pages>1143-1151</pages><issn>0003-021X</issn><eissn>1558-9331</eissn><abstract>NMR observation revealed that bidirectional conversion occurred between 3-monochloropropane-1,2-diol (3-MCPD) and glycidol in the course of the analytical procedure of DFG standard method C-III 18 (09), option A; 3-MCPD was partly converted to glycidol at the transesterification step, and glycidol was converted partly to 3-MCPD at the derivatization step conducted at 80 °C under acidic condition in the presence of NaCl. Based on the proton numbers observed by
1
H NMR, the degrees of the conversion were estimated to be 37 and >70%, respectively. In addition, epoxide ring-opening of glycidol and its esters was found to be ca. 90% by the acid treatment described in the method, option B. Thus, it was concluded that the standard method, option A, did not correctly give the combined amount of 3-MCPD esters and glycidyl esters in oils containing glycidyl esters, and the difference of the values obtained by options A and B did not correspond to the amount of glycidyl esters, either. In addition, derivatives of 3-MCPD with phenylboronic acid were not observed by NMR at the derivatization step, although they were detected by GC-MS in the organic phase at the following extraction step.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer-Verlag</pub><doi>10.1007/s11746-011-1802-3</doi><tpages>9</tpages></addata></record> |
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| subjects | 3‐Monochloropropane‐1,2‐diol (3‐MCPD) Agriculture Biological and medical sciences Biomaterials Biotechnology Chemistry Chemistry and Materials Science DFG standard method Esters Fat industries Food industries Food Science Fundamental and applied biological sciences. Psychology General aspects Glycidol Glycidyl ester Industrial Chemistry/Chemical Engineering Methods of analysis, processing and quality control, regulation, standards NaCl Original Paper Sodium chloride |
| title | Bidirectional Conversion Between 3-Monochloro-1,2-propanediol and Glycidol in Course of the Procedure of DGF Standard Methods |
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