Catalytic Transformation of Triglycerides to Biodiesel with SiO 2 -SO 3 H and Quaternary Ammonium Salts in Toluene or DMSO
SiO -SO H, with a surface area of 115 m ·g , pore volumes of 0.38 cm ·g and 1.32 mmol H /g, was used as a transesterification catalyst. Triglycerides of waste cooking oil reacted with methanol in refluxing toluene to yield mixtures of diglycerides, monoglycerides and fatty acid methyl esters (FAMEs)...
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Veröffentlicht in: | Molecules (Basel, Switzerland) Switzerland), 2022-01, Vol.27 (3) |
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creator | Barbosa, Sandro L Rocha, Adeline C Pereira Nelson, David Lee de Freitas, Milton S Mestre, Antônio A P Fulgêncio Klein, Stanlei I Clososki, Giuliano C Caires, Franco J Flumignan, Danilo L Dos Santos, Letícia Karen Wentz, Alexandre P Pasa, Vânya M Duarte Rios, Regiane D Fernandes |
description | SiO
-SO
H, with a surface area of 115 m
·g
, pore volumes of 0.38 cm
·g
and 1.32 mmol H
/g, was used as a transesterification catalyst. Triglycerides of waste cooking oil reacted with methanol in refluxing toluene to yield mixtures of diglycerides, monoglycerides and fatty acid methyl esters (FAMEs) in the presence of 20% (
/
) catalyst/oil using the hydrophilic sulfonated silica (SiO
-SO
H) catalyst alone or with the addition of 10% (
/
) co-catalyst/oil [(Bu
N)(BF
) or Aliquat 336]. The addition of the ammonium salts to the catalyst lead to a decrease in the amounts of diglycerides in the products, but the concentrations of monoglycerides increased. Mixtures of (Bu
N)(BF
)/catalyst were superior to catalyst alone or Aliquat 336/catalyst for promoting the production of mixtures with high concentrations of FAMEs. The same experiments were repeated using DMSO as the solvent. The use of the more polar solvent resulted in excellent conversion of the triglycerides to FAME esters with all three-catalyst media. A simplified mechanism is presented to account for the experimental results. |
doi_str_mv | 10.3390/molecules27030953 |
format | Article |
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-SO
H, with a surface area of 115 m
·g
, pore volumes of 0.38 cm
·g
and 1.32 mmol H
/g, was used as a transesterification catalyst. Triglycerides of waste cooking oil reacted with methanol in refluxing toluene to yield mixtures of diglycerides, monoglycerides and fatty acid methyl esters (FAMEs) in the presence of 20% (
/
) catalyst/oil using the hydrophilic sulfonated silica (SiO
-SO
H) catalyst alone or with the addition of 10% (
/
) co-catalyst/oil [(Bu
N)(BF
) or Aliquat 336]. The addition of the ammonium salts to the catalyst lead to a decrease in the amounts of diglycerides in the products, but the concentrations of monoglycerides increased. Mixtures of (Bu
N)(BF
)/catalyst were superior to catalyst alone or Aliquat 336/catalyst for promoting the production of mixtures with high concentrations of FAMEs. The same experiments were repeated using DMSO as the solvent. The use of the more polar solvent resulted in excellent conversion of the triglycerides to FAME esters with all three-catalyst media. A simplified mechanism is presented to account for the experimental results.</description><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules27030953</identifier><identifier>PMID: 35164218</identifier><language>eng</language><publisher>Switzerland</publisher><subject>Biofuels - analysis ; Catalysis ; Dimethyl Sulfoxide - chemistry ; Esterification ; Quaternary Ammonium Compounds - chemistry ; Silicon Dioxide - chemistry ; Sulfates - chemistry ; Toluene - chemistry ; Triglycerides - chemistry</subject><ispartof>Molecules (Basel, Switzerland), 2022-01, Vol.27 (3)</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0002-0294-5345 ; 0000-0001-7435-3675 ; 0000-0002-7329-5298 ; 0000-0002-5060-6479 ; 0000-0003-3207-4891</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,861,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35164218$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Barbosa, Sandro L</creatorcontrib><creatorcontrib>Rocha, Adeline C Pereira</creatorcontrib><creatorcontrib>Nelson, David Lee</creatorcontrib><creatorcontrib>de Freitas, Milton S</creatorcontrib><creatorcontrib>Mestre, Antônio A P Fulgêncio</creatorcontrib><creatorcontrib>Klein, Stanlei I</creatorcontrib><creatorcontrib>Clososki, Giuliano C</creatorcontrib><creatorcontrib>Caires, Franco J</creatorcontrib><creatorcontrib>Flumignan, Danilo L</creatorcontrib><creatorcontrib>Dos Santos, Letícia Karen</creatorcontrib><creatorcontrib>Wentz, Alexandre P</creatorcontrib><creatorcontrib>Pasa, Vânya M Duarte</creatorcontrib><creatorcontrib>Rios, Regiane D Fernandes</creatorcontrib><title>Catalytic Transformation of Triglycerides to Biodiesel with SiO 2 -SO 3 H and Quaternary Ammonium Salts in Toluene or DMSO</title><title>Molecules (Basel, Switzerland)</title><addtitle>Molecules</addtitle><description>SiO
-SO
H, with a surface area of 115 m
·g
, pore volumes of 0.38 cm
·g
and 1.32 mmol H
/g, was used as a transesterification catalyst. Triglycerides of waste cooking oil reacted with methanol in refluxing toluene to yield mixtures of diglycerides, monoglycerides and fatty acid methyl esters (FAMEs) in the presence of 20% (
/
) catalyst/oil using the hydrophilic sulfonated silica (SiO
-SO
H) catalyst alone or with the addition of 10% (
/
) co-catalyst/oil [(Bu
N)(BF
) or Aliquat 336]. The addition of the ammonium salts to the catalyst lead to a decrease in the amounts of diglycerides in the products, but the concentrations of monoglycerides increased. Mixtures of (Bu
N)(BF
)/catalyst were superior to catalyst alone or Aliquat 336/catalyst for promoting the production of mixtures with high concentrations of FAMEs. The same experiments were repeated using DMSO as the solvent. The use of the more polar solvent resulted in excellent conversion of the triglycerides to FAME esters with all three-catalyst media. A simplified mechanism is presented to account for the experimental results.</description><subject>Biofuels - analysis</subject><subject>Catalysis</subject><subject>Dimethyl Sulfoxide - chemistry</subject><subject>Esterification</subject><subject>Quaternary Ammonium Compounds - chemistry</subject><subject>Silicon Dioxide - chemistry</subject><subject>Sulfates - chemistry</subject><subject>Toluene - chemistry</subject><subject>Triglycerides - chemistry</subject><issn>1420-3049</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFjstKw1AURS8FsdX6AZ3I-YHofSTWDLVaOpFQknm5Jid6yn2U-0Di19uBjh1tWCwWm7GV4HdK1fzeeoN9NhjlmiteV2rGFqKUvFC8rOfsKsYj51KUorpkc1WJh1KKxwX73uikzZSohy5oF0cfrE7kHfjxTOjDTD0GGjBC8vBMfiCMaOCL0ie01ICEom1AwQ60G2CfdcLgdJjgyVrvKFtotUkRyEHnTUaH4AO8vLXNkl2M2kS8-d1rdrt97Ta74pTfLQ6HUyB7Dh3-zqp_hR8osFDO</recordid><startdate>20220130</startdate><enddate>20220130</enddate><creator>Barbosa, Sandro L</creator><creator>Rocha, Adeline C Pereira</creator><creator>Nelson, David Lee</creator><creator>de Freitas, Milton S</creator><creator>Mestre, Antônio A P Fulgêncio</creator><creator>Klein, Stanlei I</creator><creator>Clososki, Giuliano C</creator><creator>Caires, Franco J</creator><creator>Flumignan, Danilo L</creator><creator>Dos Santos, Letícia Karen</creator><creator>Wentz, Alexandre P</creator><creator>Pasa, Vânya M Duarte</creator><creator>Rios, Regiane D Fernandes</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><orcidid>https://orcid.org/0000-0002-0294-5345</orcidid><orcidid>https://orcid.org/0000-0001-7435-3675</orcidid><orcidid>https://orcid.org/0000-0002-7329-5298</orcidid><orcidid>https://orcid.org/0000-0002-5060-6479</orcidid><orcidid>https://orcid.org/0000-0003-3207-4891</orcidid></search><sort><creationdate>20220130</creationdate><title>Catalytic Transformation of Triglycerides to Biodiesel with SiO 2 -SO 3 H and Quaternary Ammonium Salts in Toluene or DMSO</title><author>Barbosa, Sandro L ; Rocha, Adeline C Pereira ; Nelson, David Lee ; de Freitas, Milton S ; Mestre, Antônio A P Fulgêncio ; Klein, Stanlei I ; Clososki, Giuliano C ; Caires, Franco J ; Flumignan, Danilo L ; Dos Santos, Letícia Karen ; Wentz, Alexandre P ; Pasa, Vânya M Duarte ; Rios, Regiane D Fernandes</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-pubmed_primary_351642183</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Biofuels - analysis</topic><topic>Catalysis</topic><topic>Dimethyl Sulfoxide - chemistry</topic><topic>Esterification</topic><topic>Quaternary Ammonium Compounds - chemistry</topic><topic>Silicon Dioxide - chemistry</topic><topic>Sulfates - chemistry</topic><topic>Toluene - chemistry</topic><topic>Triglycerides - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Barbosa, Sandro L</creatorcontrib><creatorcontrib>Rocha, Adeline C Pereira</creatorcontrib><creatorcontrib>Nelson, David Lee</creatorcontrib><creatorcontrib>de Freitas, Milton S</creatorcontrib><creatorcontrib>Mestre, Antônio A P Fulgêncio</creatorcontrib><creatorcontrib>Klein, Stanlei I</creatorcontrib><creatorcontrib>Clososki, Giuliano C</creatorcontrib><creatorcontrib>Caires, Franco J</creatorcontrib><creatorcontrib>Flumignan, Danilo L</creatorcontrib><creatorcontrib>Dos Santos, Letícia Karen</creatorcontrib><creatorcontrib>Wentz, Alexandre P</creatorcontrib><creatorcontrib>Pasa, Vânya M Duarte</creatorcontrib><creatorcontrib>Rios, Regiane D Fernandes</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><jtitle>Molecules (Basel, Switzerland)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Barbosa, Sandro L</au><au>Rocha, Adeline C Pereira</au><au>Nelson, David Lee</au><au>de Freitas, Milton S</au><au>Mestre, Antônio A P Fulgêncio</au><au>Klein, Stanlei I</au><au>Clososki, Giuliano C</au><au>Caires, Franco J</au><au>Flumignan, Danilo L</au><au>Dos Santos, Letícia Karen</au><au>Wentz, Alexandre P</au><au>Pasa, Vânya M Duarte</au><au>Rios, Regiane D Fernandes</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Catalytic Transformation of Triglycerides to Biodiesel with SiO 2 -SO 3 H and Quaternary Ammonium Salts in Toluene or DMSO</atitle><jtitle>Molecules (Basel, Switzerland)</jtitle><addtitle>Molecules</addtitle><date>2022-01-30</date><risdate>2022</risdate><volume>27</volume><issue>3</issue><eissn>1420-3049</eissn><abstract>SiO
-SO
H, with a surface area of 115 m
·g
, pore volumes of 0.38 cm
·g
and 1.32 mmol H
/g, was used as a transesterification catalyst. Triglycerides of waste cooking oil reacted with methanol in refluxing toluene to yield mixtures of diglycerides, monoglycerides and fatty acid methyl esters (FAMEs) in the presence of 20% (
/
) catalyst/oil using the hydrophilic sulfonated silica (SiO
-SO
H) catalyst alone or with the addition of 10% (
/
) co-catalyst/oil [(Bu
N)(BF
) or Aliquat 336]. The addition of the ammonium salts to the catalyst lead to a decrease in the amounts of diglycerides in the products, but the concentrations of monoglycerides increased. Mixtures of (Bu
N)(BF
)/catalyst were superior to catalyst alone or Aliquat 336/catalyst for promoting the production of mixtures with high concentrations of FAMEs. The same experiments were repeated using DMSO as the solvent. The use of the more polar solvent resulted in excellent conversion of the triglycerides to FAME esters with all three-catalyst media. A simplified mechanism is presented to account for the experimental results.</abstract><cop>Switzerland</cop><pmid>35164218</pmid><doi>10.3390/molecules27030953</doi><orcidid>https://orcid.org/0000-0002-0294-5345</orcidid><orcidid>https://orcid.org/0000-0001-7435-3675</orcidid><orcidid>https://orcid.org/0000-0002-7329-5298</orcidid><orcidid>https://orcid.org/0000-0002-5060-6479</orcidid><orcidid>https://orcid.org/0000-0003-3207-4891</orcidid></addata></record> |
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identifier | EISSN: 1420-3049 |
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language | eng |
recordid | cdi_pubmed_primary_35164218 |
source | MDPI - Multidisciplinary Digital Publishing Institute; MEDLINE; Full-Text Journals in Chemistry (Open access); DOAJ Directory of Open Access Journals; PubMed Central; EZB Electronic Journals Library |
subjects | Biofuels - analysis Catalysis Dimethyl Sulfoxide - chemistry Esterification Quaternary Ammonium Compounds - chemistry Silicon Dioxide - chemistry Sulfates - chemistry Toluene - chemistry Triglycerides - chemistry |
title | Catalytic Transformation of Triglycerides to Biodiesel with SiO 2 -SO 3 H and Quaternary Ammonium Salts in Toluene or DMSO |
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