Oxidation of 1-propanol to propionic acid with hydrogen peroxide catalysed by heteropolyoxometalates
Background Propionic acid as a very valuable chemical is in high demand, and it is industrially produced via the oxo-synthesis of ethylene or ethyl alcohol and via the oxidation of propionaldehyde with oxygen. It is urgent to discover a new preparation method for propionic acid via a green route. Re...
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| creator | Liu, Minxue Yu, Fengli Yuan, Bing Xie, Congxia Yu, Shitao |
| description | Background
Propionic acid as a very valuable chemical is in high demand, and it is industrially produced via the oxo-synthesis of ethylene or ethyl alcohol and via the oxidation of propionaldehyde with oxygen. It is urgent to discover a new preparation method for propionic acid via a green route. Recyclable amino-acid-based organic–inorganic heteropolyoxometalates were first used to high-efficiently catalyse the selective oxidation of 1-propanol to propionic acid with H
2
O
2
as an oxidant.
Result
A series of amino-acid-based heteropoly catalysts using different types of amino acids and heteropoly acids were synthesized, and the experimental results showed proline-based heteropolyphosphatotungstate (ProH)
3
[PW
12
O
40
] exhibited excellent catalytic activity for the selective catalytic oxidation of 1-propanol to propionic acid owing to its high capacity as an oxygen transfer agent and suitable acidity. Under optimized reaction conditions, the conversion of 1-propanol and the selectivity of propionic acid reached 88% and 75%, respectively. Over four cycles, the conversion remained at >80%, and the selectivity was >60%. (ProH)
3
[PW
12
O
40
] was also used to catalyse the oxidations of 1-butanol, 1-pentanol, 1-hexanol, and benzyl alcohol. All the reactions had high conversions, with the corresponding acids being the primary oxidation product.
Conclusions
Proline-based heteropolyoxometalate (ProH)
3
[PW
12
O
40
] has been successfully used to catalyse the selective oxidation of primary alcohols to the corresponding carboxylic acids with H
2
O
2
as the oxidant. The new developed catalytic oxidation system is mild, high-efficient, and reliable. This study provides a potential green route for the preparation propionic acid. |
| doi_str_mv | 10.1186/s13065-021-00750-5 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_doaj_</sourceid><recordid>TN_cdi_proquest_journals_2507805531</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><doaj_id>oai_doaj_org_article_42a6e61b697d49c4a91dcb1fd5aa3e1a</doaj_id><sourcerecordid>2508570043</sourcerecordid><originalsourceid>FETCH-LOGICAL-c540t-8cbf33d7fe519f8beb805ff7b61cc3f723a7ea7a6eb4af40eda8e36a23fc95bd3</originalsourceid><addsrcrecordid>eNp9kk9v1DAQxSMEolXpF-CALHHhErDjOE4uSKjiT6VKvYDEzRrb412vsnGwvdB8e7xNKS0HTh75vfnZHr-qesnoW8b67l1inHaipg2rKZWC1uJJddp0Hat7yr4_fVCfVOcp7SgtVkElb59XJ5zLoR1kc1rZ6xtvIfswkeAIq-cYZpjCSHIgx7oI3hAw3pJfPm_JdrExbHAiM8ZQWpEYyDAuCS3RC9liLvtzGJdwE_ZYFMiYXlTPHIwJz-_Ws-rbp49fL77UV9efLy8-XNVGtDTXvdGOcysdCja4XqPuqXBO6o4Zw51sOEgECR3qFlxL0UKPvIOGOzMIbflZdblybYCdmqPfQ1xUAK9uN0LcKIjZmxFV2xRMx3Q3SNsOpoWBWaOZswKAI4PCer-y5oPeozU45QjjI-hjZfJbtQk_VRm5lIwXwJs7QAw_Dpiy2vtkcBxhwnBIqhG0F5LS9mh9_Y91Fw5xKqM6umSZguCsuJrVZWJIKaK7vwyj6pgJtWZClY9Wt5lQojS9eviM-5Y_CSgGvhpSkaYNxr9n_wf7G6epxcg</addsrcrecordid><sourcetype>Open Website</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2507805531</pqid></control><display><type>article</type><title>Oxidation of 1-propanol to propionic acid with hydrogen peroxide catalysed by heteropolyoxometalates</title><source>BioMed Central Journals Complete</source><source>Springer Nature - Complete Springer Journals</source><source>DOAJ Directory of Open Access Journals</source><source>PubMed Central</source><source>Free Full-Text Journals in Chemistry</source><source>PubMed Central Open Access</source><source>Springer Nature OA Free Journals</source><creator>Liu, Minxue ; Yu, Fengli ; Yuan, Bing ; Xie, Congxia ; Yu, Shitao</creator><creatorcontrib>Liu, Minxue ; Yu, Fengli ; Yuan, Bing ; Xie, Congxia ; Yu, Shitao</creatorcontrib><description>Background
Propionic acid as a very valuable chemical is in high demand, and it is industrially produced via the oxo-synthesis of ethylene or ethyl alcohol and via the oxidation of propionaldehyde with oxygen. It is urgent to discover a new preparation method for propionic acid via a green route. Recyclable amino-acid-based organic–inorganic heteropolyoxometalates were first used to high-efficiently catalyse the selective oxidation of 1-propanol to propionic acid with H
2
O
2
as an oxidant.
Result
A series of amino-acid-based heteropoly catalysts using different types of amino acids and heteropoly acids were synthesized, and the experimental results showed proline-based heteropolyphosphatotungstate (ProH)
3
[PW
12
O
40
] exhibited excellent catalytic activity for the selective catalytic oxidation of 1-propanol to propionic acid owing to its high capacity as an oxygen transfer agent and suitable acidity. Under optimized reaction conditions, the conversion of 1-propanol and the selectivity of propionic acid reached 88% and 75%, respectively. Over four cycles, the conversion remained at >80%, and the selectivity was >60%. (ProH)
3
[PW
12
O
40
] was also used to catalyse the oxidations of 1-butanol, 1-pentanol, 1-hexanol, and benzyl alcohol. All the reactions had high conversions, with the corresponding acids being the primary oxidation product.
Conclusions
Proline-based heteropolyoxometalate (ProH)
3
[PW
12
O
40
] has been successfully used to catalyse the selective oxidation of primary alcohols to the corresponding carboxylic acids with H
2
O
2
as the oxidant. The new developed catalytic oxidation system is mild, high-efficient, and reliable. This study provides a potential green route for the preparation propionic acid.</description><identifier>ISSN: 2661-801X</identifier><identifier>EISSN: 2661-801X</identifier><identifier>DOI: 10.1186/s13065-021-00750-5</identifier><identifier>PMID: 33794972</identifier><language>eng</language><publisher>Cham: Springer International Publishing</publisher><subject>1-Propanol ; Amino acid ; Amino acids ; Benzyl alcohol ; Butanol ; Carboxylic acids ; Catalytic activity ; Catalytic oxidation ; Chemical products ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Conversion ; Ethanol ; Heteropolyoxometalate ; Hydrogen peroxide ; Oxidation ; Oxidizing agents ; Oxygen transfer ; Proline ; Propionic acid ; Research Article ; Selective oxidation ; Selectivity</subject><ispartof>BMC chemistry, 2021-04, Vol.15 (1), p.23-23, Article 23</ispartof><rights>The Author(s) 2021</rights><rights>The Author(s) 2021. This work is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c540t-8cbf33d7fe519f8beb805ff7b61cc3f723a7ea7a6eb4af40eda8e36a23fc95bd3</citedby><cites>FETCH-LOGICAL-c540t-8cbf33d7fe519f8beb805ff7b61cc3f723a7ea7a6eb4af40eda8e36a23fc95bd3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8017713/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8017713/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,2096,27901,27902,41096,41464,42165,42533,51294,51551,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33794972$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Minxue</creatorcontrib><creatorcontrib>Yu, Fengli</creatorcontrib><creatorcontrib>Yuan, Bing</creatorcontrib><creatorcontrib>Xie, Congxia</creatorcontrib><creatorcontrib>Yu, Shitao</creatorcontrib><title>Oxidation of 1-propanol to propionic acid with hydrogen peroxide catalysed by heteropolyoxometalates</title><title>BMC chemistry</title><addtitle>BMC Chemistry</addtitle><addtitle>BMC Chem</addtitle><description>Background
Propionic acid as a very valuable chemical is in high demand, and it is industrially produced via the oxo-synthesis of ethylene or ethyl alcohol and via the oxidation of propionaldehyde with oxygen. It is urgent to discover a new preparation method for propionic acid via a green route. Recyclable amino-acid-based organic–inorganic heteropolyoxometalates were first used to high-efficiently catalyse the selective oxidation of 1-propanol to propionic acid with H
2
O
2
as an oxidant.
Result
A series of amino-acid-based heteropoly catalysts using different types of amino acids and heteropoly acids were synthesized, and the experimental results showed proline-based heteropolyphosphatotungstate (ProH)
3
[PW
12
O
40
] exhibited excellent catalytic activity for the selective catalytic oxidation of 1-propanol to propionic acid owing to its high capacity as an oxygen transfer agent and suitable acidity. Under optimized reaction conditions, the conversion of 1-propanol and the selectivity of propionic acid reached 88% and 75%, respectively. Over four cycles, the conversion remained at >80%, and the selectivity was >60%. (ProH)
3
[PW
12
O
40
] was also used to catalyse the oxidations of 1-butanol, 1-pentanol, 1-hexanol, and benzyl alcohol. All the reactions had high conversions, with the corresponding acids being the primary oxidation product.
Conclusions
Proline-based heteropolyoxometalate (ProH)
3
[PW
12
O
40
] has been successfully used to catalyse the selective oxidation of primary alcohols to the corresponding carboxylic acids with H
2
O
2
as the oxidant. The new developed catalytic oxidation system is mild, high-efficient, and reliable. This study provides a potential green route for the preparation propionic acid.</description><subject>1-Propanol</subject><subject>Amino acid</subject><subject>Amino acids</subject><subject>Benzyl alcohol</subject><subject>Butanol</subject><subject>Carboxylic acids</subject><subject>Catalytic activity</subject><subject>Catalytic oxidation</subject><subject>Chemical products</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Conversion</subject><subject>Ethanol</subject><subject>Heteropolyoxometalate</subject><subject>Hydrogen peroxide</subject><subject>Oxidation</subject><subject>Oxidizing agents</subject><subject>Oxygen transfer</subject><subject>Proline</subject><subject>Propionic acid</subject><subject>Research Article</subject><subject>Selective oxidation</subject><subject>Selectivity</subject><issn>2661-801X</issn><issn>2661-801X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>C6C</sourceid><sourceid>8G5</sourceid><sourceid>BENPR</sourceid><sourceid>GUQSH</sourceid><sourceid>M2O</sourceid><sourceid>DOA</sourceid><recordid>eNp9kk9v1DAQxSMEolXpF-CALHHhErDjOE4uSKjiT6VKvYDEzRrb412vsnGwvdB8e7xNKS0HTh75vfnZHr-qesnoW8b67l1inHaipg2rKZWC1uJJddp0Hat7yr4_fVCfVOcp7SgtVkElb59XJ5zLoR1kc1rZ6xtvIfswkeAIq-cYZpjCSHIgx7oI3hAw3pJfPm_JdrExbHAiM8ZQWpEYyDAuCS3RC9liLvtzGJdwE_ZYFMiYXlTPHIwJz-_Ws-rbp49fL77UV9efLy8-XNVGtDTXvdGOcysdCja4XqPuqXBO6o4Zw51sOEgECR3qFlxL0UKPvIOGOzMIbflZdblybYCdmqPfQ1xUAK9uN0LcKIjZmxFV2xRMx3Q3SNsOpoWBWaOZswKAI4PCer-y5oPeozU45QjjI-hjZfJbtQk_VRm5lIwXwJs7QAw_Dpiy2vtkcBxhwnBIqhG0F5LS9mh9_Y91Fw5xKqM6umSZguCsuJrVZWJIKaK7vwyj6pgJtWZClY9Wt5lQojS9eviM-5Y_CSgGvhpSkaYNxr9n_wf7G6epxcg</recordid><startdate>20210401</startdate><enddate>20210401</enddate><creator>Liu, Minxue</creator><creator>Yu, Fengli</creator><creator>Yuan, Bing</creator><creator>Xie, Congxia</creator><creator>Yu, Shitao</creator><general>Springer International Publishing</general><general>Springer Nature B.V</general><general>BMC</general><scope>C6C</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7SR</scope><scope>7X7</scope><scope>7XB</scope><scope>8AO</scope><scope>8BQ</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>8G5</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>GUQSH</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>K9.</scope><scope>KB.</scope><scope>M0S</scope><scope>M2O</scope><scope>MBDVC</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>Q9U</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope></search><sort><creationdate>20210401</creationdate><title>Oxidation of 1-propanol to propionic acid with hydrogen peroxide catalysed by heteropolyoxometalates</title><author>Liu, Minxue ; Yu, Fengli ; Yuan, Bing ; Xie, Congxia ; Yu, Shitao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c540t-8cbf33d7fe519f8beb805ff7b61cc3f723a7ea7a6eb4af40eda8e36a23fc95bd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>1-Propanol</topic><topic>Amino acid</topic><topic>Amino acids</topic><topic>Benzyl alcohol</topic><topic>Butanol</topic><topic>Carboxylic acids</topic><topic>Catalytic activity</topic><topic>Catalytic oxidation</topic><topic>Chemical products</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Conversion</topic><topic>Ethanol</topic><topic>Heteropolyoxometalate</topic><topic>Hydrogen peroxide</topic><topic>Oxidation</topic><topic>Oxidizing agents</topic><topic>Oxygen transfer</topic><topic>Proline</topic><topic>Propionic acid</topic><topic>Research Article</topic><topic>Selective oxidation</topic><topic>Selectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Minxue</creatorcontrib><creatorcontrib>Yu, Fengli</creatorcontrib><creatorcontrib>Yuan, Bing</creatorcontrib><creatorcontrib>Xie, Congxia</creatorcontrib><creatorcontrib>Yu, Shitao</creatorcontrib><collection>Springer Nature OA Free Journals</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Engineered Materials Abstracts</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>ProQuest Pharma Collection</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Research Library (Alumni Edition)</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>Research Library Prep</collection><collection>SciTech Premium Collection</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Materials Science Database</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Research Library</collection><collection>Research Library (Corporate)</collection><collection>Materials Science Collection</collection><collection>Publicly Available Content Database</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 China</collection><collection>ProQuest Central Basic</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>BMC chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Minxue</au><au>Yu, Fengli</au><au>Yuan, Bing</au><au>Xie, Congxia</au><au>Yu, Shitao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Oxidation of 1-propanol to propionic acid with hydrogen peroxide catalysed by heteropolyoxometalates</atitle><jtitle>BMC chemistry</jtitle><stitle>BMC Chemistry</stitle><addtitle>BMC Chem</addtitle><date>2021-04-01</date><risdate>2021</risdate><volume>15</volume><issue>1</issue><spage>23</spage><epage>23</epage><pages>23-23</pages><artnum>23</artnum><issn>2661-801X</issn><eissn>2661-801X</eissn><abstract>Background
Propionic acid as a very valuable chemical is in high demand, and it is industrially produced via the oxo-synthesis of ethylene or ethyl alcohol and via the oxidation of propionaldehyde with oxygen. It is urgent to discover a new preparation method for propionic acid via a green route. Recyclable amino-acid-based organic–inorganic heteropolyoxometalates were first used to high-efficiently catalyse the selective oxidation of 1-propanol to propionic acid with H
2
O
2
as an oxidant.
Result
A series of amino-acid-based heteropoly catalysts using different types of amino acids and heteropoly acids were synthesized, and the experimental results showed proline-based heteropolyphosphatotungstate (ProH)
3
[PW
12
O
40
] exhibited excellent catalytic activity for the selective catalytic oxidation of 1-propanol to propionic acid owing to its high capacity as an oxygen transfer agent and suitable acidity. Under optimized reaction conditions, the conversion of 1-propanol and the selectivity of propionic acid reached 88% and 75%, respectively. Over four cycles, the conversion remained at >80%, and the selectivity was >60%. (ProH)
3
[PW
12
O
40
] was also used to catalyse the oxidations of 1-butanol, 1-pentanol, 1-hexanol, and benzyl alcohol. All the reactions had high conversions, with the corresponding acids being the primary oxidation product.
Conclusions
Proline-based heteropolyoxometalate (ProH)
3
[PW
12
O
40
] has been successfully used to catalyse the selective oxidation of primary alcohols to the corresponding carboxylic acids with H
2
O
2
as the oxidant. The new developed catalytic oxidation system is mild, high-efficient, and reliable. This study provides a potential green route for the preparation propionic acid.</abstract><cop>Cham</cop><pub>Springer International Publishing</pub><pmid>33794972</pmid><doi>10.1186/s13065-021-00750-5</doi><tpages>1</tpages><oa>free_for_read</oa></addata></record> |
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| source | BioMed Central Journals Complete; Springer Nature - Complete Springer Journals; DOAJ Directory of Open Access Journals; PubMed Central; Free Full-Text Journals in Chemistry; PubMed Central Open Access; Springer Nature OA Free Journals |
| subjects | 1-Propanol Amino acid Amino acids Benzyl alcohol Butanol Carboxylic acids Catalytic activity Catalytic oxidation Chemical products Chemistry Chemistry and Materials Science Chemistry/Food Science Conversion Ethanol Heteropolyoxometalate Hydrogen peroxide Oxidation Oxidizing agents Oxygen transfer Proline Propionic acid Research Article Selective oxidation Selectivity |
| title | Oxidation of 1-propanol to propionic acid with hydrogen peroxide catalysed by heteropolyoxometalates |
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