Production of Hydroxymethylfurfural Derivatives From Furfural Derivatives via Hydroxymethylation
Hydroxymethylfurfural (HMF) derivatives such as 2,5-bis(hydroxymethyl)furan (BHMF) and furandicarboxylic acid (FDCA) are promising alternative of fossil-based diols and dicarboxylic acids for synthesis of polyesters such as polyethylene terephthalate (PET). However, high cost for preparing HMF from...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Frontiers Media S.A.
2022-02-01
|
| Series: | Frontiers in Bioengineering and Biotechnology |
| Subjects: | |
| Online Access: | https://www.frontiersin.org/articles/10.3389/fbioe.2022.851668/full |
| _version_ | 1819278355285934080 |
|---|---|
| author | Xianqing Lv Xiaolin Luo Xin Cheng Jing Liu Changzhi Li Li Shuai |
| author_facet | Xianqing Lv Xiaolin Luo Xin Cheng Jing Liu Changzhi Li Li Shuai |
| author_sort | Xianqing Lv |
| collection | DOAJ |
| description | Hydroxymethylfurfural (HMF) derivatives such as 2,5-bis(hydroxymethyl)furan (BHMF) and furandicarboxylic acid (FDCA) are promising alternative of fossil-based diols and dicarboxylic acids for synthesis of polyesters such as polyethylene terephthalate (PET). However, high cost for preparing HMF from biomass discourages the commercialization of HMF-derived polyesters. Since producing furfural (FUR) from five-carbon sugars (e.g., xylose) via dehydration is an inexpensive and commercialized process, we herein reported a method to synthesize BHMF derivatives (5-(ethoxymethyl)furan-2-methanol (EMFM), 2,5-bis(hydroxymethyl)furan monoacetate (BHMFM) and 2,5-bis(hydroxymethyl)furan diacetate (BHMFD) from furfural derivatives, i.e., (2-(ethoxymethyl)furan (EMF) and furfuryl acetate (FA)). To avoid strong acid-induced side reactions (e.g., furan ring opening, condensation and carbonization), two reaction systems, i.e., a low-concentration HCl aqueous solution combined with formaldehyde and anhydrous acetic acid combined with paraformaldehyde, were found to be suitable for such a hydroxymethylation reaction and could lead to decent product yields. In order to improve the carbon utilization, condensed furanic byproducts were further converted into hydrocarbon fuels via a reported two-step hydrodeoxygenation (HDO) process. This study not only validates the possibility of synthesizing functional HMF derivatives (EMFM, BHMFM, and BHMFD) from commercially-available FUR derivatives (EMF and FA), but also provide a new way to transform condensed furanics to value-added hydrocarbon fuels. |
| first_indexed | 2024-12-24T00:10:41Z |
| format | Article |
| id | doaj.art-d613956bb99c448a81cbd66e6e36a636 |
| institution | Directory Open Access Journal |
| issn | 2296-4185 |
| language | English |
| last_indexed | 2024-12-24T00:10:41Z |
| publishDate | 2022-02-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Bioengineering and Biotechnology |
| spelling | doaj.art-d613956bb99c448a81cbd66e6e36a6362022-12-21T17:24:53ZengFrontiers Media S.A.Frontiers in Bioengineering and Biotechnology2296-41852022-02-011010.3389/fbioe.2022.851668851668Production of Hydroxymethylfurfural Derivatives From Furfural Derivatives via HydroxymethylationXianqing Lv0Xiaolin Luo1Xin Cheng2Jing Liu3Changzhi Li4Li Shuai5College of Materials Engineering, Fujian Agriculture and Forestry University, Fuzhou, ChinaCollege of Materials Engineering, Fujian Agriculture and Forestry University, Fuzhou, ChinaCollege of Materials Engineering, Fujian Agriculture and Forestry University, Fuzhou, ChinaCollege of Materials Engineering, Fujian Agriculture and Forestry University, Fuzhou, ChinaCAS Key Laboratory of Science and Technology on Applied Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, ChinaCollege of Materials Engineering, Fujian Agriculture and Forestry University, Fuzhou, ChinaHydroxymethylfurfural (HMF) derivatives such as 2,5-bis(hydroxymethyl)furan (BHMF) and furandicarboxylic acid (FDCA) are promising alternative of fossil-based diols and dicarboxylic acids for synthesis of polyesters such as polyethylene terephthalate (PET). However, high cost for preparing HMF from biomass discourages the commercialization of HMF-derived polyesters. Since producing furfural (FUR) from five-carbon sugars (e.g., xylose) via dehydration is an inexpensive and commercialized process, we herein reported a method to synthesize BHMF derivatives (5-(ethoxymethyl)furan-2-methanol (EMFM), 2,5-bis(hydroxymethyl)furan monoacetate (BHMFM) and 2,5-bis(hydroxymethyl)furan diacetate (BHMFD) from furfural derivatives, i.e., (2-(ethoxymethyl)furan (EMF) and furfuryl acetate (FA)). To avoid strong acid-induced side reactions (e.g., furan ring opening, condensation and carbonization), two reaction systems, i.e., a low-concentration HCl aqueous solution combined with formaldehyde and anhydrous acetic acid combined with paraformaldehyde, were found to be suitable for such a hydroxymethylation reaction and could lead to decent product yields. In order to improve the carbon utilization, condensed furanic byproducts were further converted into hydrocarbon fuels via a reported two-step hydrodeoxygenation (HDO) process. This study not only validates the possibility of synthesizing functional HMF derivatives (EMFM, BHMFM, and BHMFD) from commercially-available FUR derivatives (EMF and FA), but also provide a new way to transform condensed furanics to value-added hydrocarbon fuels.https://www.frontiersin.org/articles/10.3389/fbioe.2022.851668/fullfurfural derivativeshydroxymethylfurfual derivativeshydroxymethylationhydrocarbon fuelhydrodeoxygenation |
| spellingShingle | Xianqing Lv Xiaolin Luo Xin Cheng Jing Liu Changzhi Li Li Shuai Production of Hydroxymethylfurfural Derivatives From Furfural Derivatives via Hydroxymethylation Frontiers in Bioengineering and Biotechnology furfural derivatives hydroxymethylfurfual derivatives hydroxymethylation hydrocarbon fuel hydrodeoxygenation |
| title | Production of Hydroxymethylfurfural Derivatives From Furfural Derivatives via Hydroxymethylation |
| title_full | Production of Hydroxymethylfurfural Derivatives From Furfural Derivatives via Hydroxymethylation |
| title_fullStr | Production of Hydroxymethylfurfural Derivatives From Furfural Derivatives via Hydroxymethylation |
| title_full_unstemmed | Production of Hydroxymethylfurfural Derivatives From Furfural Derivatives via Hydroxymethylation |
| title_short | Production of Hydroxymethylfurfural Derivatives From Furfural Derivatives via Hydroxymethylation |
| title_sort | production of hydroxymethylfurfural derivatives from furfural derivatives via hydroxymethylation |
| topic | furfural derivatives hydroxymethylfurfual derivatives hydroxymethylation hydrocarbon fuel hydrodeoxygenation |
| url | https://www.frontiersin.org/articles/10.3389/fbioe.2022.851668/full |
| work_keys_str_mv | AT xianqinglv productionofhydroxymethylfurfuralderivativesfromfurfuralderivativesviahydroxymethylation AT xiaolinluo productionofhydroxymethylfurfuralderivativesfromfurfuralderivativesviahydroxymethylation AT xincheng productionofhydroxymethylfurfuralderivativesfromfurfuralderivativesviahydroxymethylation AT jingliu productionofhydroxymethylfurfuralderivativesfromfurfuralderivativesviahydroxymethylation AT changzhili productionofhydroxymethylfurfuralderivativesfromfurfuralderivativesviahydroxymethylation AT lishuai productionofhydroxymethylfurfuralderivativesfromfurfuralderivativesviahydroxymethylation |