Disproportionation of Rosin Driven by 4,4′-Thio-bis(3-Methyl-6-Tert-Butylphenol): Kinetic Model Discrimination
Herein, a phenomenological kinetic modeling of the disproportionation of rosin with a well-known antioxidant and bleaching agent, antioxidant 300, also known as 4,4′-thio-bis(3-methyl-6-tert-butylphenol) under thermal conditions adequate for rosin esterification with polyols such as glycerol or pent...
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description | Herein, a phenomenological kinetic modeling of the disproportionation of rosin with a well-known antioxidant and bleaching agent, antioxidant 300, also known as 4,4′-thio-bis(3-methyl-6-tert-butylphenol) under thermal conditions adequate for rosin esterification with polyols such as glycerol or pentaerythritol, is studied. The temperature was varied in the 260–280 °C range, while the catalyst was either absent or added till a 2% w/w amount relative to rosin. The composition of the reaction liquid was followed by GC-MS to identify the rosin acids present in each sample and GC-FID to quantify them. Gas chromatography analyses indicated that abietic acids were involved in dehydrogenation, isomerization and disproportionation reactions, while pimaric acid underwent a number of isomerization reactions, dehydroabietic acid being the main product of the disproportionation process, while abietic acid almost disappeared in the more reactive conditions. Several kinetic models featuring direct hydrogenation, disproportionation, isomerization, and dehydrogenation reactions were proposed and fitted, step by step, to all relevant data. Physicochemical and statistical discrimination allowed for the selection of the most adequate model, which includes abietic, neoabietic and palustric acid dehydrogenation to dehydroabietic acid, abietic acid disproportionation to di- and dehydroabietic acid, and pimaric acid isomerization. In any case, a model with isomerization of all abietic-type acids towards abietic acid before its further transformation via dehydrogenation and disproportionation reactions seems statistically valid as well. |
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The temperature was varied in the 260–280 °C range, while the catalyst was either absent or added till a 2% w/w amount relative to rosin. The composition of the reaction liquid was followed by GC-MS to identify the rosin acids present in each sample and GC-FID to quantify them. Gas chromatography analyses indicated that abietic acids were involved in dehydrogenation, isomerization and disproportionation reactions, while pimaric acid underwent a number of isomerization reactions, dehydroabietic acid being the main product of the disproportionation process, while abietic acid almost disappeared in the more reactive conditions. Several kinetic models featuring direct hydrogenation, disproportionation, isomerization, and dehydrogenation reactions were proposed and fitted, step by step, to all relevant data. Physicochemical and statistical discrimination allowed for the selection of the most adequate model, which includes abietic, neoabietic and palustric acid dehydrogenation to dehydroabietic acid, abietic acid disproportionation to di- and dehydroabietic acid, and pimaric acid isomerization. In any case, a model with isomerization of all abietic-type acids towards abietic acid before its further transformation via dehydrogenation and disproportionation reactions seems statistically valid as well.</description><identifier>ISSN: 2073-4344</identifier><identifier>EISSN: 2073-4344</identifier><identifier>DOI: 10.3390/catal14040235</identifier><language>eng</language><publisher>Basel: MDPI AG</publisher><subject>Antioxidants ; Bleaching ; Chromatography ; Dehydrogenation ; Disproportionation ; Esterification ; Gas chromatography ; Heat ; Hydrogen ; Hydrogenation ; Identification and classification ; Iodine ; Isomerization ; Kinetics ; Mass spectrometry ; Methyl groups ; NMR ; Nuclear magnetic resonance ; Oxidation ; Polymers ; Polyols ; Resins ; Rosin ; Spectrum analysis ; Sulfur ; Surfactants</subject><ispartof>Catalysts, 2024-04, Vol.14 (4), p.235</ispartof><rights>COPYRIGHT 2024 MDPI AG</rights><rights>2024 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). 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The temperature was varied in the 260–280 °C range, while the catalyst was either absent or added till a 2% w/w amount relative to rosin. The composition of the reaction liquid was followed by GC-MS to identify the rosin acids present in each sample and GC-FID to quantify them. Gas chromatography analyses indicated that abietic acids were involved in dehydrogenation, isomerization and disproportionation reactions, while pimaric acid underwent a number of isomerization reactions, dehydroabietic acid being the main product of the disproportionation process, while abietic acid almost disappeared in the more reactive conditions. Several kinetic models featuring direct hydrogenation, disproportionation, isomerization, and dehydrogenation reactions were proposed and fitted, step by step, to all relevant data. Physicochemical and statistical discrimination allowed for the selection of the most adequate model, which includes abietic, neoabietic and palustric acid dehydrogenation to dehydroabietic acid, abietic acid disproportionation to di- and dehydroabietic acid, and pimaric acid isomerization. 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Yustos, Pedro ; Garcia-Ochoa, Felix ; Ladero, Miguel</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c327t-b0a2b7e3f5a1ddb2a3705f375b997525eeb3c7138bd7d4c3a4e8e15ec9e97f643</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Antioxidants</topic><topic>Bleaching</topic><topic>Chromatography</topic><topic>Dehydrogenation</topic><topic>Disproportionation</topic><topic>Esterification</topic><topic>Gas chromatography</topic><topic>Heat</topic><topic>Hydrogen</topic><topic>Hydrogenation</topic><topic>Identification and classification</topic><topic>Iodine</topic><topic>Isomerization</topic><topic>Kinetics</topic><topic>Mass spectrometry</topic><topic>Methyl groups</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Oxidation</topic><topic>Polymers</topic><topic>Polyols</topic><topic>Resins</topic><topic>Rosin</topic><topic>Spectrum analysis</topic><topic>Sulfur</topic><topic>Surfactants</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Souto, Juan C</creatorcontrib><creatorcontrib>Yustos, Pedro</creatorcontrib><creatorcontrib>Garcia-Ochoa, Felix</creatorcontrib><creatorcontrib>Ladero, Miguel</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</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 (ProQuest)</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>SciTech Premium Collection</collection><collection>Materials Research Database</collection><collection>Materials Science Database</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><jtitle>Catalysts</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Souto, Juan C</au><au>Yustos, Pedro</au><au>Garcia-Ochoa, Felix</au><au>Ladero, Miguel</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Disproportionation of Rosin Driven by 4,4′-Thio-bis(3-Methyl-6-Tert-Butylphenol): Kinetic Model Discrimination</atitle><jtitle>Catalysts</jtitle><date>2024-04-01</date><risdate>2024</risdate><volume>14</volume><issue>4</issue><spage>235</spage><pages>235-</pages><issn>2073-4344</issn><eissn>2073-4344</eissn><abstract>Herein, a phenomenological kinetic modeling of the disproportionation of rosin with a well-known antioxidant and bleaching agent, antioxidant 300, also known as 4,4′-thio-bis(3-methyl-6-tert-butylphenol) under thermal conditions adequate for rosin esterification with polyols such as glycerol or pentaerythritol, is studied. The temperature was varied in the 260–280 °C range, while the catalyst was either absent or added till a 2% w/w amount relative to rosin. The composition of the reaction liquid was followed by GC-MS to identify the rosin acids present in each sample and GC-FID to quantify them. Gas chromatography analyses indicated that abietic acids were involved in dehydrogenation, isomerization and disproportionation reactions, while pimaric acid underwent a number of isomerization reactions, dehydroabietic acid being the main product of the disproportionation process, while abietic acid almost disappeared in the more reactive conditions. Several kinetic models featuring direct hydrogenation, disproportionation, isomerization, and dehydrogenation reactions were proposed and fitted, step by step, to all relevant data. Physicochemical and statistical discrimination allowed for the selection of the most adequate model, which includes abietic, neoabietic and palustric acid dehydrogenation to dehydroabietic acid, abietic acid disproportionation to di- and dehydroabietic acid, and pimaric acid isomerization. In any case, a model with isomerization of all abietic-type acids towards abietic acid before its further transformation via dehydrogenation and disproportionation reactions seems statistically valid as well.</abstract><cop>Basel</cop><pub>MDPI AG</pub><doi>10.3390/catal14040235</doi><oa>free_for_read</oa></addata></record> |
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subjects | Antioxidants Bleaching Chromatography Dehydrogenation Disproportionation Esterification Gas chromatography Heat Hydrogen Hydrogenation Identification and classification Iodine Isomerization Kinetics Mass spectrometry Methyl groups NMR Nuclear magnetic resonance Oxidation Polymers Polyols Resins Rosin Spectrum analysis Sulfur Surfactants |
title | Disproportionation of Rosin Driven by 4,4′-Thio-bis(3-Methyl-6-Tert-Butylphenol): Kinetic Model Discrimination |
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