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Investigation of the Stability of Quaternary Ammonium Methyl Carbonates
Quaternary ammonium compounds are used commercially for a variety of applications and some are of interest as ionic liquids. For many years dimethyl carbonate has been touted as a green reagent, including its use for methylation (quaternization) of tertiary amines. In addition, substitution of the m...
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| Published in: | Journal of surfactants and detergents 2012-03, Vol.15 (2), p.199-205 |
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| Main Authors: | , , , , , , , , |
| Format: | Article |
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| cites | cdi_FETCH-LOGICAL-c3639-4ed49fe6fc94c3aec97af667588e29cfc6f48c8bd19745667e91eb535b48ef873 |
| container_end_page | 205 |
| container_issue | 2 |
| container_start_page | 199 |
| container_title | Journal of surfactants and detergents |
| container_volume | 15 |
| creator | Weisshaar, Duane E. Earl, Gary W. Amolins, Michael W. Mickalowski, Kyle L. Norberg, Justin G. Rekken, Brian D. Burgess, Angela M. Kaemingk, Bethany D. Behrens, Katherine C. |
| description | Quaternary ammonium compounds are used commercially for a variety of applications and some are of interest as ionic liquids. For many years dimethyl carbonate has been touted as a green reagent, including its use for methylation (quaternization) of tertiary amines. In addition, substitution of the methyl carbonate by other anions can be efficiently and cleanly accomplished by reaction with the corresponding acid. How stable are these methyl carbonate quaternary compounds? High field
13
C NMR shows that in the presence of water, the methyl carbonate is converted to bicarbonate. Headspace GCMS indicates that the alkylammonium methyl carbonate salts are stable below 170–180 °C while the bicarbonate salts are stable to only about 140 °C. Thermal decomposition occurs by decarboxylation and by dealkylation. |
| doi_str_mv | 10.1007/s11743-011-1292-1 |
| format | article |
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13
C NMR shows that in the presence of water, the methyl carbonate is converted to bicarbonate. Headspace GCMS indicates that the alkylammonium methyl carbonate salts are stable below 170–180 °C while the bicarbonate salts are stable to only about 140 °C. Thermal decomposition occurs by decarboxylation and by dealkylation.</description><identifier>ISSN: 1097-3958</identifier><identifier>EISSN: 1558-9293</identifier><identifier>DOI: 10.1007/s11743-011-1292-1</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer-Verlag</publisher><subject>Amines ; Ammonia ; Ammonium ; Anions ; Aquatic Pollution ; Aqueous stability ; Carbonates ; Chemistry ; Chemistry and Materials Science ; Dimethyl carbonate ; Green synthesis ; Industrial Chemistry/Chemical Engineering ; Ions ; Methyl carbonate ; NMR ; Nuclear magnetic resonance ; Original Article ; Physical Chemistry ; Polymer Sciences ; Quaternary ammonium ; Surfaces and Interfaces ; Surfactant ; Thermal decomposition ; Thermal stability ; Thin Films ; Waste Water Technology ; Water Management ; Water Pollution Control</subject><ispartof>Journal of surfactants and detergents, 2012-03, Vol.15 (2), p.199-205</ispartof><rights>AOCS 2011</rights><rights>2012 American Oil Chemists' Society (AOCS)</rights><rights>AOCS 2012</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3639-4ed49fe6fc94c3aec97af667588e29cfc6f48c8bd19745667e91eb535b48ef873</citedby><cites>FETCH-LOGICAL-c3639-4ed49fe6fc94c3aec97af667588e29cfc6f48c8bd19745667e91eb535b48ef873</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27922,27923</link.rule.ids></links><search><creatorcontrib>Weisshaar, Duane E.</creatorcontrib><creatorcontrib>Earl, Gary W.</creatorcontrib><creatorcontrib>Amolins, Michael W.</creatorcontrib><creatorcontrib>Mickalowski, Kyle L.</creatorcontrib><creatorcontrib>Norberg, Justin G.</creatorcontrib><creatorcontrib>Rekken, Brian D.</creatorcontrib><creatorcontrib>Burgess, Angela M.</creatorcontrib><creatorcontrib>Kaemingk, Bethany D.</creatorcontrib><creatorcontrib>Behrens, Katherine C.</creatorcontrib><title>Investigation of the Stability of Quaternary Ammonium Methyl Carbonates</title><title>Journal of surfactants and detergents</title><addtitle>J Surfact Deterg</addtitle><description>Quaternary ammonium compounds are used commercially for a variety of applications and some are of interest as ionic liquids. For many years dimethyl carbonate has been touted as a green reagent, including its use for methylation (quaternization) of tertiary amines. In addition, substitution of the methyl carbonate by other anions can be efficiently and cleanly accomplished by reaction with the corresponding acid. How stable are these methyl carbonate quaternary compounds? High field
13
C NMR shows that in the presence of water, the methyl carbonate is converted to bicarbonate. Headspace GCMS indicates that the alkylammonium methyl carbonate salts are stable below 170–180 °C while the bicarbonate salts are stable to only about 140 °C. Thermal decomposition occurs by decarboxylation and by dealkylation.</description><subject>Amines</subject><subject>Ammonia</subject><subject>Ammonium</subject><subject>Anions</subject><subject>Aquatic Pollution</subject><subject>Aqueous stability</subject><subject>Carbonates</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Dimethyl carbonate</subject><subject>Green synthesis</subject><subject>Industrial Chemistry/Chemical Engineering</subject><subject>Ions</subject><subject>Methyl carbonate</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Original Article</subject><subject>Physical Chemistry</subject><subject>Polymer Sciences</subject><subject>Quaternary ammonium</subject><subject>Surfaces and Interfaces</subject><subject>Surfactant</subject><subject>Thermal decomposition</subject><subject>Thermal stability</subject><subject>Thin Films</subject><subject>Waste Water Technology</subject><subject>Water Management</subject><subject>Water Pollution Control</subject><issn>1097-3958</issn><issn>1558-9293</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqFkE1PwzAMhiMEEmPwA7hV3ANxkzTJcRpjDA0hNDhHaZZsnfoxmg7Uf0-mInFCnGzZfuzXL0LXQG6BEHEXAASjmABgSFWK4QSNgHOJVaroacyJEpgqLs_RRQg7QlJgnI_QfFF_utAVG9MVTZ00Pum2Lll1Ji_KouuPhdeD6Vxbm7ZPJlXV1MWhSp5dt-3LZGravKljO1yiM2_K4K5-4hi9P8zepo94-TJfTCdLbGlGFWZuzZR3mbeKWWqcVcL4LBNcSpcq623mmbQyX4MSjMeGU-ByTnnOpPNS0DG6Gfbu2-bjEJXrXXOI4sqgVQpcSAYyDsEwZNsmhNZ5vW-LKj6ggeijXXqwS0e79NEuDZERA_NVlK7_H9BPq_sZAaUimQ5kiFC9ce2vpL_PfQMSnn2_</recordid><startdate>201203</startdate><enddate>201203</enddate><creator>Weisshaar, Duane E.</creator><creator>Earl, Gary W.</creator><creator>Amolins, Michael W.</creator><creator>Mickalowski, Kyle L.</creator><creator>Norberg, Justin G.</creator><creator>Rekken, Brian D.</creator><creator>Burgess, Angela M.</creator><creator>Kaemingk, Bethany D.</creator><creator>Behrens, Katherine C.</creator><general>Springer-Verlag</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>4T-</scope><scope>7QH</scope><scope>7UA</scope><scope>7XB</scope><scope>88I</scope><scope>8AO</scope><scope>8FE</scope><scope>8FG</scope><scope>8FK</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>BHPHI</scope><scope>BKSAR</scope><scope>C1K</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>F1W</scope><scope>GNUQQ</scope><scope>H97</scope><scope>HCIFZ</scope><scope>KB.</scope><scope>L.G</scope><scope>M2P</scope><scope>PCBAR</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope></search><sort><creationdate>201203</creationdate><title>Investigation of the Stability of Quaternary Ammonium Methyl Carbonates</title><author>Weisshaar, Duane E. ; Earl, Gary W. ; Amolins, Michael W. ; Mickalowski, Kyle L. ; Norberg, Justin G. ; Rekken, Brian D. ; Burgess, Angela M. ; Kaemingk, Bethany D. ; Behrens, Katherine C.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3639-4ed49fe6fc94c3aec97af667588e29cfc6f48c8bd19745667e91eb535b48ef873</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Amines</topic><topic>Ammonia</topic><topic>Ammonium</topic><topic>Anions</topic><topic>Aquatic Pollution</topic><topic>Aqueous stability</topic><topic>Carbonates</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Dimethyl carbonate</topic><topic>Green synthesis</topic><topic>Industrial Chemistry/Chemical Engineering</topic><topic>Ions</topic><topic>Methyl carbonate</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Original Article</topic><topic>Physical Chemistry</topic><topic>Polymer Sciences</topic><topic>Quaternary ammonium</topic><topic>Surfaces and Interfaces</topic><topic>Surfactant</topic><topic>Thermal decomposition</topic><topic>Thermal stability</topic><topic>Thin Films</topic><topic>Waste Water Technology</topic><topic>Water Management</topic><topic>Water Pollution Control</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Weisshaar, Duane E.</creatorcontrib><creatorcontrib>Earl, Gary W.</creatorcontrib><creatorcontrib>Amolins, Michael W.</creatorcontrib><creatorcontrib>Mickalowski, Kyle L.</creatorcontrib><creatorcontrib>Norberg, Justin G.</creatorcontrib><creatorcontrib>Rekken, Brian D.</creatorcontrib><creatorcontrib>Burgess, Angela M.</creatorcontrib><creatorcontrib>Kaemingk, Bethany D.</creatorcontrib><creatorcontrib>Behrens, Katherine C.</creatorcontrib><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Docstoc</collection><collection>Aqualine</collection><collection>Water Resources Abstracts</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Science Database (Alumni Edition)</collection><collection>ProQuest Pharma Collection</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest One Sustainability</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Earth, Atmospheric & Aquatic Science Collection</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>ProQuest Central Student</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 3: Aquatic Pollution & Environmental Quality</collection><collection>SciTech Premium Collection</collection><collection>https://resources.nclive.org/materials</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><collection>ProQuest Science Journals</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 surfactants and detergents</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Weisshaar, Duane E.</au><au>Earl, Gary W.</au><au>Amolins, Michael W.</au><au>Mickalowski, Kyle L.</au><au>Norberg, Justin G.</au><au>Rekken, Brian D.</au><au>Burgess, Angela M.</au><au>Kaemingk, Bethany D.</au><au>Behrens, Katherine C.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Investigation of the Stability of Quaternary Ammonium Methyl Carbonates</atitle><jtitle>Journal of surfactants and detergents</jtitle><stitle>J Surfact Deterg</stitle><date>2012-03</date><risdate>2012</risdate><volume>15</volume><issue>2</issue><spage>199</spage><epage>205</epage><pages>199-205</pages><issn>1097-3958</issn><eissn>1558-9293</eissn><abstract>Quaternary ammonium compounds are used commercially for a variety of applications and some are of interest as ionic liquids. For many years dimethyl carbonate has been touted as a green reagent, including its use for methylation (quaternization) of tertiary amines. In addition, substitution of the methyl carbonate by other anions can be efficiently and cleanly accomplished by reaction with the corresponding acid. How stable are these methyl carbonate quaternary compounds? High field
13
C NMR shows that in the presence of water, the methyl carbonate is converted to bicarbonate. Headspace GCMS indicates that the alkylammonium methyl carbonate salts are stable below 170–180 °C while the bicarbonate salts are stable to only about 140 °C. Thermal decomposition occurs by decarboxylation and by dealkylation.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer-Verlag</pub><doi>10.1007/s11743-011-1292-1</doi><tpages>7</tpages></addata></record> |
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| identifier | ISSN: 1097-3958 |
| ispartof | Journal of surfactants and detergents, 2012-03, Vol.15 (2), p.199-205 |
| issn | 1097-3958 1558-9293 |
| language | eng |
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| source | Wiley-Blackwell Read & Publish Collection |
| subjects | Amines Ammonia Ammonium Anions Aquatic Pollution Aqueous stability Carbonates Chemistry Chemistry and Materials Science Dimethyl carbonate Green synthesis Industrial Chemistry/Chemical Engineering Ions Methyl carbonate NMR Nuclear magnetic resonance Original Article Physical Chemistry Polymer Sciences Quaternary ammonium Surfaces and Interfaces Surfactant Thermal decomposition Thermal stability Thin Films Waste Water Technology Water Management Water Pollution Control |
| title | Investigation of the Stability of Quaternary Ammonium Methyl Carbonates |
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