Catalytic Cleavage of the C-O Bond in 2,6-dimethoxyphenol Without External Hydrogen or Organic Solvent Using Catalytic Vanadium Metal
Hydrogenolysis of the C-O bonds in lignin, which promises to be able to generate fuels and chemical feedstocks from biomass, is a particularly challenging and important area of investigation. Herein, we demonstrate a vanadium-catalyzed cleavage of a lignin model compound (2,6-dimethoxyphenol). The i...
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| Format: | Article |
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Frontiers Media S.A.
2020-07-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/article/10.3389/fchem.2020.00636/full |
| _version_ | 1818500404515700736 |
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| author | Peng Yu Xue Xie Pengfei Tan Wei Zhang Zhiguo Wang Chun Zhang Hui Liu |
| author_facet | Peng Yu Xue Xie Pengfei Tan Wei Zhang Zhiguo Wang Chun Zhang Hui Liu |
| author_sort | Peng Yu |
| collection | DOAJ |
| description | Hydrogenolysis of the C-O bonds in lignin, which promises to be able to generate fuels and chemical feedstocks from biomass, is a particularly challenging and important area of investigation. Herein, we demonstrate a vanadium-catalyzed cleavage of a lignin model compound (2,6-dimethoxyphenol). The impact of the catalyst in the context of the temperature, reaction time, and the solvent, was examined for the cleavage of the methyl ethers in 2,6-dimethoxyphenol. In contrast to traditional catalytic transfer hydrogenolysis, which requires high pressure hydrogen gas or reductive organic molecules, such as an alcohol and formic acid, the vanadium catalyst demonstrates superior catalytic activity on the cleavage of the C-O bonds using water as a solvent. For example, the conversion of 2,6-dimethoxyphenol is 89.5% at 280°C after 48 h using distilled water. Notably, the vanadium-catalyzed cleavage of the C-O bond linkage in 2,6-dimethoxyphenol affords 3-methoxycatechol, which undergoes further cleavage to afford pyrogallol. This work is expected to provide an alternative method for the hydrogenolysis of lignin and related compounds into valuable chemicals in the absence of external hydrogen and organic solvents. |
| first_indexed | 2024-12-10T20:42:19Z |
| format | Article |
| id | doaj.art-9a1b1e8ae6494b0b9db1b75eb13bbfd7 |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-12-10T20:42:19Z |
| publishDate | 2020-07-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-9a1b1e8ae6494b0b9db1b75eb13bbfd72022-12-22T01:34:20ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462020-07-01810.3389/fchem.2020.00636565350Catalytic Cleavage of the C-O Bond in 2,6-dimethoxyphenol Without External Hydrogen or Organic Solvent Using Catalytic Vanadium MetalPeng Yu0Xue Xie1Pengfei Tan2Wei Zhang3Zhiguo Wang4Chun Zhang5Hui Liu6College of Chemistry and Material Science, Hunan Agricultural University, Changsha, ChinaCollege of Chemistry and Material Science, Hunan Agricultural University, Changsha, ChinaState Key Laboratory for Powder Metallurgy, Central South University, Changsha, ChinaCollege of Chemistry and Material Science, Hunan Agricultural University, Changsha, ChinaCollege of Chemistry and Material Science, Hunan Agricultural University, Changsha, ChinaCollege of Chemistry and Material Science, Hunan Agricultural University, Changsha, ChinaCollege of Chemistry and Material Science, Hunan Agricultural University, Changsha, ChinaHydrogenolysis of the C-O bonds in lignin, which promises to be able to generate fuels and chemical feedstocks from biomass, is a particularly challenging and important area of investigation. Herein, we demonstrate a vanadium-catalyzed cleavage of a lignin model compound (2,6-dimethoxyphenol). The impact of the catalyst in the context of the temperature, reaction time, and the solvent, was examined for the cleavage of the methyl ethers in 2,6-dimethoxyphenol. In contrast to traditional catalytic transfer hydrogenolysis, which requires high pressure hydrogen gas or reductive organic molecules, such as an alcohol and formic acid, the vanadium catalyst demonstrates superior catalytic activity on the cleavage of the C-O bonds using water as a solvent. For example, the conversion of 2,6-dimethoxyphenol is 89.5% at 280°C after 48 h using distilled water. Notably, the vanadium-catalyzed cleavage of the C-O bond linkage in 2,6-dimethoxyphenol affords 3-methoxycatechol, which undergoes further cleavage to afford pyrogallol. This work is expected to provide an alternative method for the hydrogenolysis of lignin and related compounds into valuable chemicals in the absence of external hydrogen and organic solvents.https://www.frontiersin.org/article/10.3389/fchem.2020.00636/full2,6-dimethoxyphenolvanadium metalligninC-O cleavagehydrogenolysis |
| spellingShingle | Peng Yu Xue Xie Pengfei Tan Wei Zhang Zhiguo Wang Chun Zhang Hui Liu Catalytic Cleavage of the C-O Bond in 2,6-dimethoxyphenol Without External Hydrogen or Organic Solvent Using Catalytic Vanadium Metal Frontiers in Chemistry 2,6-dimethoxyphenol vanadium metal lignin C-O cleavage hydrogenolysis |
| title | Catalytic Cleavage of the C-O Bond in 2,6-dimethoxyphenol Without External Hydrogen or Organic Solvent Using Catalytic Vanadium Metal |
| title_full | Catalytic Cleavage of the C-O Bond in 2,6-dimethoxyphenol Without External Hydrogen or Organic Solvent Using Catalytic Vanadium Metal |
| title_fullStr | Catalytic Cleavage of the C-O Bond in 2,6-dimethoxyphenol Without External Hydrogen or Organic Solvent Using Catalytic Vanadium Metal |
| title_full_unstemmed | Catalytic Cleavage of the C-O Bond in 2,6-dimethoxyphenol Without External Hydrogen or Organic Solvent Using Catalytic Vanadium Metal |
| title_short | Catalytic Cleavage of the C-O Bond in 2,6-dimethoxyphenol Without External Hydrogen or Organic Solvent Using Catalytic Vanadium Metal |
| title_sort | catalytic cleavage of the c o bond in 2 6 dimethoxyphenol without external hydrogen or organic solvent using catalytic vanadium metal |
| topic | 2,6-dimethoxyphenol vanadium metal lignin C-O cleavage hydrogenolysis |
| url | https://www.frontiersin.org/article/10.3389/fchem.2020.00636/full |
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