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Understanding green-hydrocarbon production through the strategy of biomass ketalization reaction
The use of oil refineries to convert second generation biomass (BM) into fuels is a powerful approach to reduce the carbon footprint. However, BM undergoes parallel reactions, yielding undesirable products during its transformation chain. We overcame this limitation by converting BM under mild condi...
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| Published in: | Sustainable energy & fuels 2023-05, Vol.7 (9), p.2244-2258 |
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| cites | cdi_FETCH-LOGICAL-c281t-b94a6753c9dcd4967148a668a75e162959e8d2312648576595ee691d8e8150243 |
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| creator | dos Santos, Débora Henrique, Fábio Lam, Yiu Lau Pereira, Marcelo M |
| description | The use of oil refineries to convert second generation biomass (BM) into fuels is a powerful approach to reduce the carbon footprint. However, BM undergoes parallel reactions, yielding undesirable products during its transformation chain. We overcame this limitation by converting BM under mild conditions using acetone, obtaining a new bio-petroleum (BP) composed of sugar acetals, without carbon loss. We studied the conversion of DX, 1,2:3,5-di-
O
-isopropylidene-α-
d
-xylofuranose, a major component in BP, into hydrocarbons to obtain insights into the DX transformation pathway and how DX and its derivatives interact with hydrocarbons present in the reaction medium. DX mixed with hydrocarbons (10 to 20 wt%) was cracked by beta zeolite at 500 °C in a fixed bed reactor. The hydrocarbons competed with DX for the active sites of the zeolite, slightly decreasing the transformation of DX and its intermediates in increasing order:
n
-hexane < cyclohexane < methylcyclohexane < toluene (pattern further supported by DFT calculations). The hydrocarbons with increasing hydrogen transfer capacity increased the yields of aromatics and naphthenics and the level of green carbon incorporated as useful products (85-90%). We observed that water was the first product of deoxygenation. Then acetone and furans were important intermediates for subsequent decarbonylation and decarboxylation, yielding hydrocarbons. DX reduced the hydrocarbon protolysis of both σC-C and σC-H bonds, decreasing the formation of H
2
and light hydrocarbons while the co-feed (intermediates) contributed to the formation of aromatics (enabling a bimolecular reaction with oxygenates). These insights may be used to improve the catalysts and the process of BP conversion into target products.
The use of oil refineries to convert second generation biomass (BM) into fuels is a powerful approach to reduce the carbon footprint. |
| doi_str_mv | 10.1039/d2se01731h |
| format | article |
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O
-isopropylidene-α-
d
-xylofuranose, a major component in BP, into hydrocarbons to obtain insights into the DX transformation pathway and how DX and its derivatives interact with hydrocarbons present in the reaction medium. DX mixed with hydrocarbons (10 to 20 wt%) was cracked by beta zeolite at 500 °C in a fixed bed reactor. The hydrocarbons competed with DX for the active sites of the zeolite, slightly decreasing the transformation of DX and its intermediates in increasing order:
n
-hexane < cyclohexane < methylcyclohexane < toluene (pattern further supported by DFT calculations). The hydrocarbons with increasing hydrogen transfer capacity increased the yields of aromatics and naphthenics and the level of green carbon incorporated as useful products (85-90%). We observed that water was the first product of deoxygenation. Then acetone and furans were important intermediates for subsequent decarbonylation and decarboxylation, yielding hydrocarbons. DX reduced the hydrocarbon protolysis of both σC-C and σC-H bonds, decreasing the formation of H
2
and light hydrocarbons while the co-feed (intermediates) contributed to the formation of aromatics (enabling a bimolecular reaction with oxygenates). These insights may be used to improve the catalysts and the process of BP conversion into target products.
The use of oil refineries to convert second generation biomass (BM) into fuels is a powerful approach to reduce the carbon footprint.</description><identifier>ISSN: 2398-4902</identifier><identifier>EISSN: 2398-4902</identifier><identifier>DOI: 10.1039/d2se01731h</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Acetals ; Acetone ; Aromatic compounds ; Biomass ; Carbon ; Carbon footprint ; Catalysts ; Conversion ; Cyclohexane ; Decarboxylation ; Deoxygenation ; Fixed bed reactors ; Fixed beds ; Furans ; Hexanes ; Hydrocarbons ; Intermediates ; Methylcyclohexane ; n-Hexane ; Oil refineries ; Pesticides ; Refineries ; Toluene ; Transformations ; Zeolites</subject><ispartof>Sustainable energy & fuels, 2023-05, Vol.7 (9), p.2244-2258</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-b94a6753c9dcd4967148a668a75e162959e8d2312648576595ee691d8e8150243</citedby><cites>FETCH-LOGICAL-c281t-b94a6753c9dcd4967148a668a75e162959e8d2312648576595ee691d8e8150243</cites><orcidid>0000-0003-1175-9699 ; 0000-0001-5958-3552</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,786,790,27957,27958</link.rule.ids></links><search><creatorcontrib>dos Santos, Débora</creatorcontrib><creatorcontrib>Henrique, Fábio</creatorcontrib><creatorcontrib>Lam, Yiu Lau</creatorcontrib><creatorcontrib>Pereira, Marcelo M</creatorcontrib><title>Understanding green-hydrocarbon production through the strategy of biomass ketalization reaction</title><title>Sustainable energy & fuels</title><description>The use of oil refineries to convert second generation biomass (BM) into fuels is a powerful approach to reduce the carbon footprint. However, BM undergoes parallel reactions, yielding undesirable products during its transformation chain. We overcame this limitation by converting BM under mild conditions using acetone, obtaining a new bio-petroleum (BP) composed of sugar acetals, without carbon loss. We studied the conversion of DX, 1,2:3,5-di-
O
-isopropylidene-α-
d
-xylofuranose, a major component in BP, into hydrocarbons to obtain insights into the DX transformation pathway and how DX and its derivatives interact with hydrocarbons present in the reaction medium. DX mixed with hydrocarbons (10 to 20 wt%) was cracked by beta zeolite at 500 °C in a fixed bed reactor. The hydrocarbons competed with DX for the active sites of the zeolite, slightly decreasing the transformation of DX and its intermediates in increasing order:
n
-hexane < cyclohexane < methylcyclohexane < toluene (pattern further supported by DFT calculations). The hydrocarbons with increasing hydrogen transfer capacity increased the yields of aromatics and naphthenics and the level of green carbon incorporated as useful products (85-90%). We observed that water was the first product of deoxygenation. Then acetone and furans were important intermediates for subsequent decarbonylation and decarboxylation, yielding hydrocarbons. DX reduced the hydrocarbon protolysis of both σC-C and σC-H bonds, decreasing the formation of H
2
and light hydrocarbons while the co-feed (intermediates) contributed to the formation of aromatics (enabling a bimolecular reaction with oxygenates). These insights may be used to improve the catalysts and the process of BP conversion into target products.
The use of oil refineries to convert second generation biomass (BM) into fuels is a powerful approach to reduce the carbon footprint.</description><subject>Acetals</subject><subject>Acetone</subject><subject>Aromatic compounds</subject><subject>Biomass</subject><subject>Carbon</subject><subject>Carbon footprint</subject><subject>Catalysts</subject><subject>Conversion</subject><subject>Cyclohexane</subject><subject>Decarboxylation</subject><subject>Deoxygenation</subject><subject>Fixed bed reactors</subject><subject>Fixed beds</subject><subject>Furans</subject><subject>Hexanes</subject><subject>Hydrocarbons</subject><subject>Intermediates</subject><subject>Methylcyclohexane</subject><subject>n-Hexane</subject><subject>Oil refineries</subject><subject>Pesticides</subject><subject>Refineries</subject><subject>Toluene</subject><subject>Transformations</subject><subject>Zeolites</subject><issn>2398-4902</issn><issn>2398-4902</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpNkDtPwzAURi0EElXpwo4UiQ0p4HfsEZWWIlVigM7BtW-TlDYutjOUX09oETB933DuQwehS4JvCWb6ztEImBSM1CdoQJlWOdeYnv7r52gU4xpjTAnlVBQD9LZoHYSYTOuatsqqANDm9d4Fb01Y-jbbBe86m5q-pjr4rqr7hCymYBJU-8yvsmXjtybG7B2S2TSf5gAHMIepC3S2MpsIo58cosV08jqe5fPnx6fx_Ty3VJGULzU3shDMamcd17IgXBkplSkEEEm10KAcZYRKrkQhhRYAUhOnQBGBKWdDdH3c2z_80UFM5dp3oe1PllRhRTVXWPfUzZGywccYYFXuQrM1YV8SXH5LLB_oy-QgcdbDV0c4RPvL_UlmX33MboM</recordid><startdate>20230502</startdate><enddate>20230502</enddate><creator>dos Santos, Débora</creator><creator>Henrique, Fábio</creator><creator>Lam, Yiu Lau</creator><creator>Pereira, Marcelo M</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7SP</scope><scope>7ST</scope><scope>7U6</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>L7M</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0003-1175-9699</orcidid><orcidid>https://orcid.org/0000-0001-5958-3552</orcidid></search><sort><creationdate>20230502</creationdate><title>Understanding green-hydrocarbon production through the strategy of biomass ketalization reaction</title><author>dos Santos, Débora ; Henrique, Fábio ; Lam, Yiu Lau ; Pereira, Marcelo M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-b94a6753c9dcd4967148a668a75e162959e8d2312648576595ee691d8e8150243</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Acetals</topic><topic>Acetone</topic><topic>Aromatic compounds</topic><topic>Biomass</topic><topic>Carbon</topic><topic>Carbon footprint</topic><topic>Catalysts</topic><topic>Conversion</topic><topic>Cyclohexane</topic><topic>Decarboxylation</topic><topic>Deoxygenation</topic><topic>Fixed bed reactors</topic><topic>Fixed beds</topic><topic>Furans</topic><topic>Hexanes</topic><topic>Hydrocarbons</topic><topic>Intermediates</topic><topic>Methylcyclohexane</topic><topic>n-Hexane</topic><topic>Oil refineries</topic><topic>Pesticides</topic><topic>Refineries</topic><topic>Toluene</topic><topic>Transformations</topic><topic>Zeolites</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>dos Santos, Débora</creatorcontrib><creatorcontrib>Henrique, Fábio</creatorcontrib><creatorcontrib>Lam, Yiu Lau</creatorcontrib><creatorcontrib>Pereira, Marcelo M</creatorcontrib><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Electronics & Communications Abstracts</collection><collection>Environment Abstracts</collection><collection>Sustainability Science Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Sustainable energy & fuels</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>dos Santos, Débora</au><au>Henrique, Fábio</au><au>Lam, Yiu Lau</au><au>Pereira, Marcelo M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Understanding green-hydrocarbon production through the strategy of biomass ketalization reaction</atitle><jtitle>Sustainable energy & fuels</jtitle><date>2023-05-02</date><risdate>2023</risdate><volume>7</volume><issue>9</issue><spage>2244</spage><epage>2258</epage><pages>2244-2258</pages><issn>2398-4902</issn><eissn>2398-4902</eissn><notes>https://doi.org/10.1039/d2se01731h</notes><notes>Electronic supplementary information (ESI) available. See DOI</notes><abstract>The use of oil refineries to convert second generation biomass (BM) into fuels is a powerful approach to reduce the carbon footprint. However, BM undergoes parallel reactions, yielding undesirable products during its transformation chain. We overcame this limitation by converting BM under mild conditions using acetone, obtaining a new bio-petroleum (BP) composed of sugar acetals, without carbon loss. We studied the conversion of DX, 1,2:3,5-di-
O
-isopropylidene-α-
d
-xylofuranose, a major component in BP, into hydrocarbons to obtain insights into the DX transformation pathway and how DX and its derivatives interact with hydrocarbons present in the reaction medium. DX mixed with hydrocarbons (10 to 20 wt%) was cracked by beta zeolite at 500 °C in a fixed bed reactor. The hydrocarbons competed with DX for the active sites of the zeolite, slightly decreasing the transformation of DX and its intermediates in increasing order:
n
-hexane < cyclohexane < methylcyclohexane < toluene (pattern further supported by DFT calculations). The hydrocarbons with increasing hydrogen transfer capacity increased the yields of aromatics and naphthenics and the level of green carbon incorporated as useful products (85-90%). We observed that water was the first product of deoxygenation. Then acetone and furans were important intermediates for subsequent decarbonylation and decarboxylation, yielding hydrocarbons. DX reduced the hydrocarbon protolysis of both σC-C and σC-H bonds, decreasing the formation of H
2
and light hydrocarbons while the co-feed (intermediates) contributed to the formation of aromatics (enabling a bimolecular reaction with oxygenates). These insights may be used to improve the catalysts and the process of BP conversion into target products.
The use of oil refineries to convert second generation biomass (BM) into fuels is a powerful approach to reduce the carbon footprint.</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d2se01731h</doi><tpages>15</tpages><orcidid>https://orcid.org/0000-0003-1175-9699</orcidid><orcidid>https://orcid.org/0000-0001-5958-3552</orcidid></addata></record> |
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| source | Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list) |
| subjects | Acetals Acetone Aromatic compounds Biomass Carbon Carbon footprint Catalysts Conversion Cyclohexane Decarboxylation Deoxygenation Fixed bed reactors Fixed beds Furans Hexanes Hydrocarbons Intermediates Methylcyclohexane n-Hexane Oil refineries Pesticides Refineries Toluene Transformations Zeolites |
| title | Understanding green-hydrocarbon production through the strategy of biomass ketalization reaction |
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