Green synthesis of enantiomerically pure l-lactide and d-lactide using biogenic creatinine catalyst
Enantiomerically pure lactides of l-lactide (LLA) and d-lactide (DLA) were synthesized with high yield (68.5–69.5%) via depolymerization of oligo-poly-l-lactic acid (O-PLLA) and oligo-poly-d-lactic acid (O-PDLA) catalyzed by biogenic creatinine (CR). The structures of synthesized LLA and DLA were ch...
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| Veröffentlicht in: | Polymer degradation and stability 2014-03, Vol.101, p.18-23 |
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| creator | Huang, Wei Qi, Yunbiao Cheng, Na Zong, Xupeng Zhang, Tianrong Jiang, Wei Li, Hong Zhang, Quanxing |
| description | Enantiomerically pure lactides of l-lactide (LLA) and d-lactide (DLA) were synthesized with high yield (68.5–69.5%) via depolymerization of oligo-poly-l-lactic acid (O-PLLA) and oligo-poly-d-lactic acid (O-PDLA) catalyzed by biogenic creatinine (CR). The structures of synthesized LLA and DLA were characterized with XRD analysis of the prepared single crystals. Gas chromatograph (with a chiral stationary phase capillary column) analysis demonstrated that the synthesized LLA and DLA possessed enantiomeric excess of 100%. The catalytic efficiency of the catalyst creatinine reached to a high level as observed by the turnover frequency in the range of 338.0–347.7 h−1. The residues of the depolymerization were utilized for resynthesizing of the enantiomerically pure lactides for 3 circles without the decrease in the yields of enantiomerically pure LLA/DLA. The catalyst we used in this research was biogenic and the process for lactide synthesis featured a closed-cycle without any waste release. A possible mechanism of CR-catalyzed LLA/DLA synthesis was proposed and discussed. |
| doi_str_mv | 10.1016/j.polymdegradstab.2014.01.022 |
| format | Article |
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The structures of synthesized LLA and DLA were characterized with XRD analysis of the prepared single crystals. Gas chromatograph (with a chiral stationary phase capillary column) analysis demonstrated that the synthesized LLA and DLA possessed enantiomeric excess of 100%. The catalytic efficiency of the catalyst creatinine reached to a high level as observed by the turnover frequency in the range of 338.0–347.7 h−1. The residues of the depolymerization were utilized for resynthesizing of the enantiomerically pure lactides for 3 circles without the decrease in the yields of enantiomerically pure LLA/DLA. The catalyst we used in this research was biogenic and the process for lactide synthesis featured a closed-cycle without any waste release. A possible mechanism of CR-catalyzed LLA/DLA synthesis was proposed and discussed.</description><identifier>ISSN: 0141-3910</identifier><identifier>EISSN: 1873-2321</identifier><identifier>DOI: 10.1016/j.polymdegradstab.2014.01.022</identifier><identifier>CODEN: PDSTDW</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>Applied sciences ; Catalysts ; Chromium ; Creatinine ; Depolymerization ; Enantiomerically pure ; Exact sciences and technology ; Lactides ; Polymer industry, paints, wood ; Residues ; Residues recycling ; Stability ; Synthesis ; Technology of polymers ; Waste treatment ; Wastes ; X-ray diffraction</subject><ispartof>Polymer degradation and stability, 2014-03, Vol.101, p.18-23</ispartof><rights>2014 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c499t-7096fb27e76b4a8cddf0970a7293d5da7dc079cf2b69ae668ac408ad49d45423</citedby><cites>FETCH-LOGICAL-c499t-7096fb27e76b4a8cddf0970a7293d5da7dc079cf2b69ae668ac408ad49d45423</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.polymdegradstab.2014.01.022$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=28361474$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Huang, Wei</creatorcontrib><creatorcontrib>Qi, Yunbiao</creatorcontrib><creatorcontrib>Cheng, Na</creatorcontrib><creatorcontrib>Zong, Xupeng</creatorcontrib><creatorcontrib>Zhang, Tianrong</creatorcontrib><creatorcontrib>Jiang, Wei</creatorcontrib><creatorcontrib>Li, Hong</creatorcontrib><creatorcontrib>Zhang, Quanxing</creatorcontrib><title>Green synthesis of enantiomerically pure l-lactide and d-lactide using biogenic creatinine catalyst</title><title>Polymer degradation and stability</title><description>Enantiomerically pure lactides of l-lactide (LLA) and d-lactide (DLA) were synthesized with high yield (68.5–69.5%) via depolymerization of oligo-poly-l-lactic acid (O-PLLA) and oligo-poly-d-lactic acid (O-PDLA) catalyzed by biogenic creatinine (CR). The structures of synthesized LLA and DLA were characterized with XRD analysis of the prepared single crystals. Gas chromatograph (with a chiral stationary phase capillary column) analysis demonstrated that the synthesized LLA and DLA possessed enantiomeric excess of 100%. The catalytic efficiency of the catalyst creatinine reached to a high level as observed by the turnover frequency in the range of 338.0–347.7 h−1. The residues of the depolymerization were utilized for resynthesizing of the enantiomerically pure lactides for 3 circles without the decrease in the yields of enantiomerically pure LLA/DLA. The catalyst we used in this research was biogenic and the process for lactide synthesis featured a closed-cycle without any waste release. A possible mechanism of CR-catalyzed LLA/DLA synthesis was proposed and discussed.</description><subject>Applied sciences</subject><subject>Catalysts</subject><subject>Chromium</subject><subject>Creatinine</subject><subject>Depolymerization</subject><subject>Enantiomerically pure</subject><subject>Exact sciences and technology</subject><subject>Lactides</subject><subject>Polymer industry, paints, wood</subject><subject>Residues</subject><subject>Residues recycling</subject><subject>Stability</subject><subject>Synthesis</subject><subject>Technology of polymers</subject><subject>Waste treatment</subject><subject>Wastes</subject><subject>X-ray diffraction</subject><issn>0141-3910</issn><issn>1873-2321</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqNkUGLFDEQhYMoOK7-h1wWvHSbSqeTzsGDLDoKC172HqqT6jFDT3pMMkL_e3uZZQ9e3LoURX1VD95j7BZECwL0p2N7Xub1FOiQMZSKYysFqFZAK6R8xXYwmK6RnYTXbLctoOksiLfsXSlHsZXqYcf8PhMlXtZUf1GJhS8Tp4SpxuVEOXqc55WfL5n43MzoawzEMQUenqdLienAx7gcKEXPfSasMcVE3GPFeS31PXsz4Vzow1O_YQ_fvj7cfW_uf-5_3H25b7yytjZGWD2N0pDRo8LBhzAJawQaabvQBzTBC2P9JEdtkbQe0CsxYFA2qF7J7oZ9vL495-X3hUp1p1g8zTMmWi7FgTbGWg0WXoJCP3RG6f-jfW-1sgrshn6-oj4vpWSa3DnHE-bVgXCPibmj-ycx95iYE-C2xLb72ycpLJvxU8bkY3l-IodOgzJq4_ZXjjYz_0TKrvhIyVOImXx1YYkvVPwL25a21g</recordid><startdate>20140301</startdate><enddate>20140301</enddate><creator>Huang, Wei</creator><creator>Qi, Yunbiao</creator><creator>Cheng, Na</creator><creator>Zong, Xupeng</creator><creator>Zhang, Tianrong</creator><creator>Jiang, Wei</creator><creator>Li, Hong</creator><creator>Zhang, Quanxing</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20140301</creationdate><title>Green synthesis of enantiomerically pure l-lactide and d-lactide using biogenic creatinine catalyst</title><author>Huang, Wei ; Qi, Yunbiao ; Cheng, Na ; Zong, Xupeng ; Zhang, Tianrong ; Jiang, Wei ; Li, Hong ; Zhang, Quanxing</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c499t-7096fb27e76b4a8cddf0970a7293d5da7dc079cf2b69ae668ac408ad49d45423</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Applied sciences</topic><topic>Catalysts</topic><topic>Chromium</topic><topic>Creatinine</topic><topic>Depolymerization</topic><topic>Enantiomerically pure</topic><topic>Exact sciences and technology</topic><topic>Lactides</topic><topic>Polymer industry, paints, wood</topic><topic>Residues</topic><topic>Residues recycling</topic><topic>Stability</topic><topic>Synthesis</topic><topic>Technology of polymers</topic><topic>Waste treatment</topic><topic>Wastes</topic><topic>X-ray diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Huang, Wei</creatorcontrib><creatorcontrib>Qi, Yunbiao</creatorcontrib><creatorcontrib>Cheng, Na</creatorcontrib><creatorcontrib>Zong, Xupeng</creatorcontrib><creatorcontrib>Zhang, Tianrong</creatorcontrib><creatorcontrib>Jiang, Wei</creatorcontrib><creatorcontrib>Li, Hong</creatorcontrib><creatorcontrib>Zhang, Quanxing</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Polymer degradation and stability</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Huang, Wei</au><au>Qi, Yunbiao</au><au>Cheng, Na</au><au>Zong, Xupeng</au><au>Zhang, Tianrong</au><au>Jiang, Wei</au><au>Li, Hong</au><au>Zhang, Quanxing</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Green synthesis of enantiomerically pure l-lactide and d-lactide using biogenic creatinine catalyst</atitle><jtitle>Polymer degradation and stability</jtitle><date>2014-03-01</date><risdate>2014</risdate><volume>101</volume><spage>18</spage><epage>23</epage><pages>18-23</pages><issn>0141-3910</issn><eissn>1873-2321</eissn><coden>PDSTDW</coden><abstract>Enantiomerically pure lactides of l-lactide (LLA) and d-lactide (DLA) were synthesized with high yield (68.5–69.5%) via depolymerization of oligo-poly-l-lactic acid (O-PLLA) and oligo-poly-d-lactic acid (O-PDLA) catalyzed by biogenic creatinine (CR). The structures of synthesized LLA and DLA were characterized with XRD analysis of the prepared single crystals. Gas chromatograph (with a chiral stationary phase capillary column) analysis demonstrated that the synthesized LLA and DLA possessed enantiomeric excess of 100%. The catalytic efficiency of the catalyst creatinine reached to a high level as observed by the turnover frequency in the range of 338.0–347.7 h−1. The residues of the depolymerization were utilized for resynthesizing of the enantiomerically pure lactides for 3 circles without the decrease in the yields of enantiomerically pure LLA/DLA. The catalyst we used in this research was biogenic and the process for lactide synthesis featured a closed-cycle without any waste release. A possible mechanism of CR-catalyzed LLA/DLA synthesis was proposed and discussed.</abstract><cop>Kidlington</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.polymdegradstab.2014.01.022</doi><tpages>6</tpages></addata></record> |
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| subjects | Applied sciences Catalysts Chromium Creatinine Depolymerization Enantiomerically pure Exact sciences and technology Lactides Polymer industry, paints, wood Residues Residues recycling Stability Synthesis Technology of polymers Waste treatment Wastes X-ray diffraction |
| title | Green synthesis of enantiomerically pure l-lactide and d-lactide using biogenic creatinine catalyst |
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