PTFE-Carbon Nanotubes and Lipase B from <em>Candida antarctica</em>—Long-Lasting Marriage for Ultra-Fast and Fully Selective Synthesis of Levulinate Esters
An effective method for levulinic acid esters synthesis by the enzymatic Fischer esterification of levulinic acid using a lipase B from <i>Candida antarctica</i> (CALB) immobilized on the advanced material consisting of multi-wall carbon nanotubes (MWCNTs) and a hydrophobic polymer—polyt...
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2021-03-01
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| author | Anna Szelwicka Agnieszka Siewniak Anna Kolanowska Sławomir Boncel Anna Chrobok |
| author_facet | Anna Szelwicka Agnieszka Siewniak Anna Kolanowska Sławomir Boncel Anna Chrobok |
| author_sort | Anna Szelwicka |
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| description | An effective method for levulinic acid esters synthesis by the enzymatic Fischer esterification of levulinic acid using a lipase B from <i>Candida antarctica</i> (CALB) immobilized on the advanced material consisting of multi-wall carbon nanotubes (MWCNTs) and a hydrophobic polymer—polytetrafluoroethylene (Teflon, PTFE)—as a heterogeneous biocatalyst, was developed. An active phase of the biocatalyst was obtained by immobilization via interfacial activation on the surface of the hybrid material MWCNTs/PTFE (immobilization yield: 6%, activity of CALB: 5000 U∙L∙kg<sup>−1</sup>, enzyme loading: 22.5 wt.%). The catalytic activity of the obtained biocatalyst and the effects of the selected reaction parameters, including the agitation speed, the amount of PTFE in the CALB/MWCNT-PTFE biocatalyst, the amount of CALB/MWCNT-PTFE, the type of organic solvent, <i>n</i>-butanol excess, were tested in the esterification of levulinic acid by <i>n</i>-butanol. The results showed that the use of a two-fold excess of levulinic acid to <i>n</i>-butanol, 22.5 wt.% of CALB on MWCNT-PTFE (0.10 wt.%) and cyclohexane as a solvent at 20 °C allowed one to obtain <i>n</i>-butyl levulinate with a high yield (99%) and selectivity (>99%) after 45 min. The catalyst retained its activity and stability after three cycles, and then started to lose activity until dropping to a 69% yield of ester in the sixth reaction run. The presented method has opened the new possibilities for environmentally friendly synthesis of levulinate esters. |
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| spelling | doaj.art-e1e9b765468e4dd1becd1ef2b21c71422023-11-21T11:16:10ZengMDPI AGMaterials1996-19442021-03-01146151810.3390/ma14061518PTFE-Carbon Nanotubes and Lipase B from <em>Candida antarctica</em>—Long-Lasting Marriage for Ultra-Fast and Fully Selective Synthesis of Levulinate EstersAnna Szelwicka0Agnieszka Siewniak1Anna Kolanowska2Sławomir Boncel3Anna Chrobok4Department of Chemical Organic Technology and Petrochemistry, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, PolandDepartment of Chemical Organic Technology and Petrochemistry, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, PolandDepartment of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Krzywoustego 4, 44-100 Gliwice, PolandDepartment of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Krzywoustego 4, 44-100 Gliwice, PolandDepartment of Chemical Organic Technology and Petrochemistry, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, PolandAn effective method for levulinic acid esters synthesis by the enzymatic Fischer esterification of levulinic acid using a lipase B from <i>Candida antarctica</i> (CALB) immobilized on the advanced material consisting of multi-wall carbon nanotubes (MWCNTs) and a hydrophobic polymer—polytetrafluoroethylene (Teflon, PTFE)—as a heterogeneous biocatalyst, was developed. An active phase of the biocatalyst was obtained by immobilization via interfacial activation on the surface of the hybrid material MWCNTs/PTFE (immobilization yield: 6%, activity of CALB: 5000 U∙L∙kg<sup>−1</sup>, enzyme loading: 22.5 wt.%). The catalytic activity of the obtained biocatalyst and the effects of the selected reaction parameters, including the agitation speed, the amount of PTFE in the CALB/MWCNT-PTFE biocatalyst, the amount of CALB/MWCNT-PTFE, the type of organic solvent, <i>n</i>-butanol excess, were tested in the esterification of levulinic acid by <i>n</i>-butanol. The results showed that the use of a two-fold excess of levulinic acid to <i>n</i>-butanol, 22.5 wt.% of CALB on MWCNT-PTFE (0.10 wt.%) and cyclohexane as a solvent at 20 °C allowed one to obtain <i>n</i>-butyl levulinate with a high yield (99%) and selectivity (>99%) after 45 min. The catalyst retained its activity and stability after three cycles, and then started to lose activity until dropping to a 69% yield of ester in the sixth reaction run. The presented method has opened the new possibilities for environmentally friendly synthesis of levulinate esters.https://www.mdpi.com/1996-1944/14/6/1518levulinate esterslevulinic acidlipasecarbon nanotubes |
| spellingShingle | Anna Szelwicka Agnieszka Siewniak Anna Kolanowska Sławomir Boncel Anna Chrobok PTFE-Carbon Nanotubes and Lipase B from <em>Candida antarctica</em>—Long-Lasting Marriage for Ultra-Fast and Fully Selective Synthesis of Levulinate Esters Materials levulinate esters levulinic acid lipase carbon nanotubes |
| title | PTFE-Carbon Nanotubes and Lipase B from <em>Candida antarctica</em>—Long-Lasting Marriage for Ultra-Fast and Fully Selective Synthesis of Levulinate Esters |
| title_full | PTFE-Carbon Nanotubes and Lipase B from <em>Candida antarctica</em>—Long-Lasting Marriage for Ultra-Fast and Fully Selective Synthesis of Levulinate Esters |
| title_fullStr | PTFE-Carbon Nanotubes and Lipase B from <em>Candida antarctica</em>—Long-Lasting Marriage for Ultra-Fast and Fully Selective Synthesis of Levulinate Esters |
| title_full_unstemmed | PTFE-Carbon Nanotubes and Lipase B from <em>Candida antarctica</em>—Long-Lasting Marriage for Ultra-Fast and Fully Selective Synthesis of Levulinate Esters |
| title_short | PTFE-Carbon Nanotubes and Lipase B from <em>Candida antarctica</em>—Long-Lasting Marriage for Ultra-Fast and Fully Selective Synthesis of Levulinate Esters |
| title_sort | ptfe carbon nanotubes and lipase b from em candida antarctica em long lasting marriage for ultra fast and fully selective synthesis of levulinate esters |
| topic | levulinate esters levulinic acid lipase carbon nanotubes |
| url | https://www.mdpi.com/1996-1944/14/6/1518 |
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