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Green Synthesis of Natural Benzaldehyde from Cinnamon Oil Catalyzed by Hydroxypropyl-β-Cyclodextrin
The efficient synthesis of natural benzaldehyde from natural cinnamon oil catalyzed by 2-hydroxypropyl-β-cyclodextrin (2-HPβ-CD) in water under rather mild conditions has been developed. Various analysis methods e.g. DSC, UV-vis, 1H NMR, ROESY and fluorescence measurements had been utilized to demon...
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| Published in: | Tetrahedron 2010-12, Vol.66 (52), p.9888-9893 |
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| container_end_page | 9893 |
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| creator | Chen, Hongyan Ji, Hongbing Zhou, Xiantai Wang, Lefu |
| description | The efficient synthesis of natural benzaldehyde from natural cinnamon oil catalyzed by 2-hydroxypropyl-β-cyclodextrin (2-HPβ-CD) in water under rather mild conditions has been developed. Various analysis methods e.g. DSC, UV-vis,
1H NMR, ROESY and fluorescence measurements had been utilized to demonstrate formation of the 1:1 (molar ratio) complexes between 2-HPβ-CD and cinnamaldehyde. The inclusion equilibrium constant K
a was 928 M
−1 at 298K. The inclusion complex activated the substrate and promoted the reaction selectivity. The yield for benzaldehyde could reach 70% under the optimized conditions (323 K, 5h, 2% NaOH (w/v), cinnamaldehyde: 2-HPβ-CD = 1: 1 (molar ratio)). Further investigation on kinetics and solubilization revealed that the binding ability between 2-HPβ-CD and cinnamaldehyde is primarily responsible for the catalytic effects.
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| doi_str_mv | 10.1016/j.tet.2010.10.063 |
| format | article |
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1H NMR, ROESY and fluorescence measurements had been utilized to demonstrate formation of the 1:1 (molar ratio) complexes between 2-HPβ-CD and cinnamaldehyde. The inclusion equilibrium constant K
a was 928 M
−1 at 298K. The inclusion complex activated the substrate and promoted the reaction selectivity. The yield for benzaldehyde could reach 70% under the optimized conditions (323 K, 5h, 2% NaOH (w/v), cinnamaldehyde: 2-HPβ-CD = 1: 1 (molar ratio)). Further investigation on kinetics and solubilization revealed that the binding ability between 2-HPβ-CD and cinnamaldehyde is primarily responsible for the catalytic effects.
[Display omitted]</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2010.10.063</identifier><identifier>CODEN: TETRAB</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>2-hydroxypropyl-β-cyclodextrin ; Benzaldehyde ; Binding ; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides ; Carbohydrates. Nucleosides and nucleotides ; Chemistry ; Cinnamaldehyde ; Exact sciences and technology ; Fluorescence ; Formations ; inclusion complex ; Kinetics and mechanisms ; natural benzaldehyde ; Noncondensed benzenic compounds ; Organic chemistry ; Preparations and properties ; Reactivity and mechanisms ; Solubilization ; Synthesis (chemistry) ; Tetrahedrons</subject><ispartof>Tetrahedron, 2010-12, Vol.66 (52), p.9888-9893</ispartof><rights>2010</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c360t-b3c1c34600a66e2bf2dbc39a01eeb485f3d169324db05edf098864f011d1f4d83</citedby><cites>FETCH-LOGICAL-c360t-b3c1c34600a66e2bf2dbc39a01eeb485f3d169324db05edf098864f011d1f4d83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,778,782,27911,27912</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23659955$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Chen, Hongyan</creatorcontrib><creatorcontrib>Ji, Hongbing</creatorcontrib><creatorcontrib>Zhou, Xiantai</creatorcontrib><creatorcontrib>Wang, Lefu</creatorcontrib><title>Green Synthesis of Natural Benzaldehyde from Cinnamon Oil Catalyzed by Hydroxypropyl-β-Cyclodextrin</title><title>Tetrahedron</title><description>The efficient synthesis of natural benzaldehyde from natural cinnamon oil catalyzed by 2-hydroxypropyl-β-cyclodextrin (2-HPβ-CD) in water under rather mild conditions has been developed. Various analysis methods e.g. DSC, UV-vis,
1H NMR, ROESY and fluorescence measurements had been utilized to demonstrate formation of the 1:1 (molar ratio) complexes between 2-HPβ-CD and cinnamaldehyde. The inclusion equilibrium constant K
a was 928 M
−1 at 298K. The inclusion complex activated the substrate and promoted the reaction selectivity. The yield for benzaldehyde could reach 70% under the optimized conditions (323 K, 5h, 2% NaOH (w/v), cinnamaldehyde: 2-HPβ-CD = 1: 1 (molar ratio)). Further investigation on kinetics and solubilization revealed that the binding ability between 2-HPβ-CD and cinnamaldehyde is primarily responsible for the catalytic effects.
[Display omitted]</description><subject>2-hydroxypropyl-β-cyclodextrin</subject><subject>Benzaldehyde</subject><subject>Binding</subject><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>Cinnamaldehyde</subject><subject>Exact sciences and technology</subject><subject>Fluorescence</subject><subject>Formations</subject><subject>inclusion complex</subject><subject>Kinetics and mechanisms</subject><subject>natural benzaldehyde</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Reactivity and mechanisms</subject><subject>Solubilization</subject><subject>Synthesis (chemistry)</subject><subject>Tetrahedrons</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNp9kMFuEzEQhi0EEqHwANx8QeKyYbz2OllxglVpkSp6AM6W1x6rjhw72A6q-1g8CM_EhlQcOY1m9P8z83-EvGawZsDku926Yl338Ldfg-RPyIoJKbpBMPmUrAAEdAJ6eE5elLIDAMZ6viL2KiNG-rXFeofFF5oc_aLrMetAP2J80MHiXbNIXU57OvkY9T5FeusDnXTVoT2gpXOj183mdN8OOR1a6H7_6qZmQrJ4X7OPL8kzp0PBV4_1gnz_dPltuu5ubq8-Tx9uOsMl1G7mhhkuJICWEvvZ9XY2fNTAEGexHRy3TI68F3aGAa2DcbuVwi1JLHPCbvkFeXveu7zx44ilqr0vBkPQEdOxKLYRQm6k2MAiZWepyamUjE4dst_r3BQDdSKqdmohqk5ET6OF6OJ587heF6ODyzoaX_4Zey6HcRyGRff-rMMl60-PWRXjMRq0PqOpyib_nyt_ABmRjT4</recordid><startdate>20101224</startdate><enddate>20101224</enddate><creator>Chen, Hongyan</creator><creator>Ji, Hongbing</creator><creator>Zhou, Xiantai</creator><creator>Wang, Lefu</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20101224</creationdate><title>Green Synthesis of Natural Benzaldehyde from Cinnamon Oil Catalyzed by Hydroxypropyl-β-Cyclodextrin</title><author>Chen, Hongyan ; Ji, Hongbing ; Zhou, Xiantai ; Wang, Lefu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c360t-b3c1c34600a66e2bf2dbc39a01eeb485f3d169324db05edf098864f011d1f4d83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>2-hydroxypropyl-β-cyclodextrin</topic><topic>Benzaldehyde</topic><topic>Binding</topic><topic>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Chemistry</topic><topic>Cinnamaldehyde</topic><topic>Exact sciences and technology</topic><topic>Fluorescence</topic><topic>Formations</topic><topic>inclusion complex</topic><topic>Kinetics and mechanisms</topic><topic>natural benzaldehyde</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Reactivity and mechanisms</topic><topic>Solubilization</topic><topic>Synthesis (chemistry)</topic><topic>Tetrahedrons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Hongyan</creatorcontrib><creatorcontrib>Ji, Hongbing</creatorcontrib><creatorcontrib>Zhou, Xiantai</creatorcontrib><creatorcontrib>Wang, Lefu</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Hongyan</au><au>Ji, Hongbing</au><au>Zhou, Xiantai</au><au>Wang, Lefu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Green Synthesis of Natural Benzaldehyde from Cinnamon Oil Catalyzed by Hydroxypropyl-β-Cyclodextrin</atitle><jtitle>Tetrahedron</jtitle><date>2010-12-24</date><risdate>2010</risdate><volume>66</volume><issue>52</issue><spage>9888</spage><epage>9893</epage><pages>9888-9893</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><coden>TETRAB</coden><abstract>The efficient synthesis of natural benzaldehyde from natural cinnamon oil catalyzed by 2-hydroxypropyl-β-cyclodextrin (2-HPβ-CD) in water under rather mild conditions has been developed. Various analysis methods e.g. DSC, UV-vis,
1H NMR, ROESY and fluorescence measurements had been utilized to demonstrate formation of the 1:1 (molar ratio) complexes between 2-HPβ-CD and cinnamaldehyde. The inclusion equilibrium constant K
a was 928 M
−1 at 298K. The inclusion complex activated the substrate and promoted the reaction selectivity. The yield for benzaldehyde could reach 70% under the optimized conditions (323 K, 5h, 2% NaOH (w/v), cinnamaldehyde: 2-HPβ-CD = 1: 1 (molar ratio)). Further investigation on kinetics and solubilization revealed that the binding ability between 2-HPβ-CD and cinnamaldehyde is primarily responsible for the catalytic effects.
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| fulltext | fulltext |
| identifier | ISSN: 0040-4020 |
| ispartof | Tetrahedron, 2010-12, Vol.66 (52), p.9888-9893 |
| issn | 0040-4020 1464-5416 |
| language | eng |
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| source | ScienceDirect Journals |
| subjects | 2-hydroxypropyl-β-cyclodextrin Benzaldehyde Binding Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Cinnamaldehyde Exact sciences and technology Fluorescence Formations inclusion complex Kinetics and mechanisms natural benzaldehyde Noncondensed benzenic compounds Organic chemistry Preparations and properties Reactivity and mechanisms Solubilization Synthesis (chemistry) Tetrahedrons |
| title | Green Synthesis of Natural Benzaldehyde from Cinnamon Oil Catalyzed by Hydroxypropyl-β-Cyclodextrin |
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