NMR Spectroscopic Study of the Aldoxane Formation in Aqueous Acetaldehyde Solutions
Crotonaldehyde is an interesting intermediate in the chemical industry. It is usually produced from aqueous acetaldehyde in a two step process in which the first step is carried out under basic and the second step under acidic conditions. It is commonly assumed that acetaldehyde is converted in the...
Gespeichert in:
| Veröffentlicht in: | Industrial & engineering chemistry research 2014-05, Vol.53 (20), p.8395-8403 |
|---|---|
| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 8403 |
|---|---|
| container_issue | 20 |
| container_start_page | 8395 |
| container_title | Industrial & engineering chemistry research |
| container_volume | 53 |
| creator | Scheithauer, Andreas Grützner, Thomas Rijksen, Christiaan Zollinger, Daniel von Harbou, Erik Thiel, Werner R Hasse, Hans |
| description | Crotonaldehyde is an interesting intermediate in the chemical industry. It is usually produced from aqueous acetaldehyde in a two step process in which the first step is carried out under basic and the second step under acidic conditions. It is commonly assumed that acetaldehyde is converted in the first step to acetaldol and that acetaldol is subsequently dehydrated in the second step to crotonaldehyde. We demonstrate by 1H and 13C NMR spectroscopic studies that acetaldol is hardly present in the reacting solutions at lower temperatures and that the key intermediate is aldoxane (2,6-dimethyl-1,3-dioxane-4-ol). For the first time, data on the chemical equilibrium of the aldoxane formation in aqueous acetaldehyde solutions is provided. Furthermore, preliminary information on the kinetics of that reaction is presented. |
| doi_str_mv | 10.1021/ie5004043 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1701121936</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1701121936</sourcerecordid><originalsourceid>FETCH-LOGICAL-a292t-be3f3fd77dbb61656d38bdba769950d5de3dfaca473bc1c343e8a008416f47e53</originalsourceid><addsrcrecordid>eNpt0MFLwzAUBvAgCs7pwf8gF0EP1ZcmadNjGU6FqWD1XNLklXV0TU1a2P57OyaePL3Lj8f3fYRcM7hnELOHBiWAAMFPyIzJGCIJQp6SGSilIqmUPCcXIWwAQEohZqR4e_2gRY9m8C4Y1zeGFsNo99TVdFgjzVvrdrpDunR-q4fGdbTpaP49ohsDzQ0OurW43lukhWvHAwiX5KzWbcCr3zsnX8vHz8VztHp_elnkq0jHWTxEFfKa1zZNbVUlLJGJ5aqylU6TLJNgpUVua220SHllmOGCo9IASrCkFilKPie3x7-9d1OgMJTbJhhs2ynvlK5kKTAWs4wnE707UjPVDB7rsvfNVvt9yaA8DFf-DTfZm6PVJpQbN_puKvGP-wHO1WxE</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1701121936</pqid></control><display><type>article</type><title>NMR Spectroscopic Study of the Aldoxane Formation in Aqueous Acetaldehyde Solutions</title><source>ACS Publications</source><creator>Scheithauer, Andreas ; Grützner, Thomas ; Rijksen, Christiaan ; Zollinger, Daniel ; von Harbou, Erik ; Thiel, Werner R ; Hasse, Hans</creator><creatorcontrib>Scheithauer, Andreas ; Grützner, Thomas ; Rijksen, Christiaan ; Zollinger, Daniel ; von Harbou, Erik ; Thiel, Werner R ; Hasse, Hans</creatorcontrib><description>Crotonaldehyde is an interesting intermediate in the chemical industry. It is usually produced from aqueous acetaldehyde in a two step process in which the first step is carried out under basic and the second step under acidic conditions. It is commonly assumed that acetaldehyde is converted in the first step to acetaldol and that acetaldol is subsequently dehydrated in the second step to crotonaldehyde. We demonstrate by 1H and 13C NMR spectroscopic studies that acetaldol is hardly present in the reacting solutions at lower temperatures and that the key intermediate is aldoxane (2,6-dimethyl-1,3-dioxane-4-ol). For the first time, data on the chemical equilibrium of the aldoxane formation in aqueous acetaldehyde solutions is provided. Furthermore, preliminary information on the kinetics of that reaction is presented.</description><identifier>ISSN: 0888-5885</identifier><identifier>EISSN: 1520-5045</identifier><identifier>DOI: 10.1021/ie5004043</identifier><language>eng</language><publisher>American Chemical Society</publisher><subject>Acetaldehyde ; Chemical industries ; Formations ; Industrial engineering ; Nuclear magnetic resonance ; Reaction kinetics ; Spectroscopic analysis ; Spectroscopy</subject><ispartof>Industrial & engineering chemistry research, 2014-05, Vol.53 (20), p.8395-8403</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a292t-be3f3fd77dbb61656d38bdba769950d5de3dfaca473bc1c343e8a008416f47e53</citedby><cites>FETCH-LOGICAL-a292t-be3f3fd77dbb61656d38bdba769950d5de3dfaca473bc1c343e8a008416f47e53</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ie5004043$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ie5004043$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27075,27923,27924,56737,56787</link.rule.ids></links><search><creatorcontrib>Scheithauer, Andreas</creatorcontrib><creatorcontrib>Grützner, Thomas</creatorcontrib><creatorcontrib>Rijksen, Christiaan</creatorcontrib><creatorcontrib>Zollinger, Daniel</creatorcontrib><creatorcontrib>von Harbou, Erik</creatorcontrib><creatorcontrib>Thiel, Werner R</creatorcontrib><creatorcontrib>Hasse, Hans</creatorcontrib><title>NMR Spectroscopic Study of the Aldoxane Formation in Aqueous Acetaldehyde Solutions</title><title>Industrial & engineering chemistry research</title><addtitle>Ind. Eng. Chem. Res</addtitle><description>Crotonaldehyde is an interesting intermediate in the chemical industry. It is usually produced from aqueous acetaldehyde in a two step process in which the first step is carried out under basic and the second step under acidic conditions. It is commonly assumed that acetaldehyde is converted in the first step to acetaldol and that acetaldol is subsequently dehydrated in the second step to crotonaldehyde. We demonstrate by 1H and 13C NMR spectroscopic studies that acetaldol is hardly present in the reacting solutions at lower temperatures and that the key intermediate is aldoxane (2,6-dimethyl-1,3-dioxane-4-ol). For the first time, data on the chemical equilibrium of the aldoxane formation in aqueous acetaldehyde solutions is provided. Furthermore, preliminary information on the kinetics of that reaction is presented.</description><subject>Acetaldehyde</subject><subject>Chemical industries</subject><subject>Formations</subject><subject>Industrial engineering</subject><subject>Nuclear magnetic resonance</subject><subject>Reaction kinetics</subject><subject>Spectroscopic analysis</subject><subject>Spectroscopy</subject><issn>0888-5885</issn><issn>1520-5045</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNpt0MFLwzAUBvAgCs7pwf8gF0EP1ZcmadNjGU6FqWD1XNLklXV0TU1a2P57OyaePL3Lj8f3fYRcM7hnELOHBiWAAMFPyIzJGCIJQp6SGSilIqmUPCcXIWwAQEohZqR4e_2gRY9m8C4Y1zeGFsNo99TVdFgjzVvrdrpDunR-q4fGdbTpaP49ohsDzQ0OurW43lukhWvHAwiX5KzWbcCr3zsnX8vHz8VztHp_elnkq0jHWTxEFfKa1zZNbVUlLJGJ5aqylU6TLJNgpUVua220SHllmOGCo9IASrCkFilKPie3x7-9d1OgMJTbJhhs2ynvlK5kKTAWs4wnE707UjPVDB7rsvfNVvt9yaA8DFf-DTfZm6PVJpQbN_puKvGP-wHO1WxE</recordid><startdate>20140521</startdate><enddate>20140521</enddate><creator>Scheithauer, Andreas</creator><creator>Grützner, Thomas</creator><creator>Rijksen, Christiaan</creator><creator>Zollinger, Daniel</creator><creator>von Harbou, Erik</creator><creator>Thiel, Werner R</creator><creator>Hasse, Hans</creator><general>American Chemical Society</general><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>20140521</creationdate><title>NMR Spectroscopic Study of the Aldoxane Formation in Aqueous Acetaldehyde Solutions</title><author>Scheithauer, Andreas ; Grützner, Thomas ; Rijksen, Christiaan ; Zollinger, Daniel ; von Harbou, Erik ; Thiel, Werner R ; Hasse, Hans</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a292t-be3f3fd77dbb61656d38bdba769950d5de3dfaca473bc1c343e8a008416f47e53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Acetaldehyde</topic><topic>Chemical industries</topic><topic>Formations</topic><topic>Industrial engineering</topic><topic>Nuclear magnetic resonance</topic><topic>Reaction kinetics</topic><topic>Spectroscopic analysis</topic><topic>Spectroscopy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Scheithauer, Andreas</creatorcontrib><creatorcontrib>Grützner, Thomas</creatorcontrib><creatorcontrib>Rijksen, Christiaan</creatorcontrib><creatorcontrib>Zollinger, Daniel</creatorcontrib><creatorcontrib>von Harbou, Erik</creatorcontrib><creatorcontrib>Thiel, Werner R</creatorcontrib><creatorcontrib>Hasse, Hans</creatorcontrib><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>Industrial & engineering chemistry research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Scheithauer, Andreas</au><au>Grützner, Thomas</au><au>Rijksen, Christiaan</au><au>Zollinger, Daniel</au><au>von Harbou, Erik</au><au>Thiel, Werner R</au><au>Hasse, Hans</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>NMR Spectroscopic Study of the Aldoxane Formation in Aqueous Acetaldehyde Solutions</atitle><jtitle>Industrial & engineering chemistry research</jtitle><addtitle>Ind. Eng. Chem. Res</addtitle><date>2014-05-21</date><risdate>2014</risdate><volume>53</volume><issue>20</issue><spage>8395</spage><epage>8403</epage><pages>8395-8403</pages><issn>0888-5885</issn><eissn>1520-5045</eissn><abstract>Crotonaldehyde is an interesting intermediate in the chemical industry. It is usually produced from aqueous acetaldehyde in a two step process in which the first step is carried out under basic and the second step under acidic conditions. It is commonly assumed that acetaldehyde is converted in the first step to acetaldol and that acetaldol is subsequently dehydrated in the second step to crotonaldehyde. We demonstrate by 1H and 13C NMR spectroscopic studies that acetaldol is hardly present in the reacting solutions at lower temperatures and that the key intermediate is aldoxane (2,6-dimethyl-1,3-dioxane-4-ol). For the first time, data on the chemical equilibrium of the aldoxane formation in aqueous acetaldehyde solutions is provided. Furthermore, preliminary information on the kinetics of that reaction is presented.</abstract><pub>American Chemical Society</pub><doi>10.1021/ie5004043</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0888-5885 |
| ispartof | Industrial & engineering chemistry research, 2014-05, Vol.53 (20), p.8395-8403 |
| issn | 0888-5885 1520-5045 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1701121936 |
| source | ACS Publications |
| subjects | Acetaldehyde Chemical industries Formations Industrial engineering Nuclear magnetic resonance Reaction kinetics Spectroscopic analysis Spectroscopy |
| title | NMR Spectroscopic Study of the Aldoxane Formation in Aqueous Acetaldehyde Solutions |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-12T12%3A37%3A59IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=NMR%20Spectroscopic%20Study%20of%20the%20Aldoxane%20Formation%20in%20Aqueous%20Acetaldehyde%20Solutions&rft.jtitle=Industrial%20&%20engineering%20chemistry%20research&rft.au=Scheithauer,%20Andreas&rft.date=2014-05-21&rft.volume=53&rft.issue=20&rft.spage=8395&rft.epage=8403&rft.pages=8395-8403&rft.issn=0888-5885&rft.eissn=1520-5045&rft_id=info:doi/10.1021/ie5004043&rft_dat=%3Cproquest_cross%3E1701121936%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1701121936&rft_id=info:pmid/&rfr_iscdi=true |