Chemistry:5-Methylfurfural
5-Methylfurfural is an organic compound with the formula C
6H
6O
2. An aldehyde that is derived through various extractions and reductions from cellulose products,[1][2] it has applications as a synthetic intermediate[3] relevant to the fields of medicine, agriculture and cosmetics.[4] It is a food additive, and has FEMA number 270s and JECFA number 745.[5] Reduction of 5-methylfurfural gives the product 5-methylfurfuryl alcohol.[6]
Synthesis
The synthesis of 5-methylfurfural has been documented from as early as 1891. It was originally synthesized from rhamnose, but can be produced from the dehydration of sucrose and other cellulose products.[1] Several synthetic pathways have been proposed from 5-hydroxymethylfurfural.[3][7] The compound has been produced in the 21st century using the historical precursor of rhamnose with the aim to use it as a precursor to biogasoline.[8][4]
References
- ↑ 1.0 1.1 "5-METHYLFURFURAL". Organic Syntheses 14: 62. 1934. doi:10.15227/orgsyn.014.0062. http://orgsyn.org/demo.aspx?prep=CV2P0393.
- ↑ Moe, Størker T.; Marcotullio, Gianluca; Opedal, Mihaela Tanase; Brusletto, Rune (December 2022). "Formation of 5-methylfurfural and 2-acetylfuran from lignocellulosic biomass and by Cr3+-catalyzed dehydration of 6-deoxyhexoses" (in en). Carbohydrate Research 522. doi:10.1016/j.carres.2022.108672. PMID 36183617. https://linkinghub.elsevier.com/retrieve/pii/S0008621522001732.
- ↑ 3.0 3.1 Li, Shaopeng; Dong, Minghua; Yang, Junjuan; Cheng, Xiaomeng; Shen, Xiaojun; Liu, Shulin; Wang, Zhi-Qiang; Gong, Xue-Qing et al. (January 26, 2021). "Selective hydrogenation of 5-(hydroxymethyl)furfural to 5-methylfurfural over single atomic metals anchored on Nb2O5" (in en). Nature Communications 12 (1): 584. doi:10.1038/s41467-020-20878-7. ISSN 2041-1723. PMID 33500400.
- ↑ 4.0 4.1 Peng, Yang; Li, Xianghua; Gao, Tian; Li, Teng; Yang, Weiran (2019). "Preparation of 5-methylfurfural from starch in one step by iodide mediated metal-free hydrogenolysis" (in en). Green Chemistry 21 (15): 4169–4177. doi:10.1039/C9GC01645G. ISSN 1463-9262. https://xlink.rsc.org/?DOI=C9GC01645G.
- ↑ "Online Edition: "Specifications for Flavourings"". 2002. https://www.fao.org/food/food-safety-quality/scientific-advice/jecfa/jecfa-flav/details/en/c/1124/.
- ↑ Spillman, Philip J.; Pollnitz, Alan P.; Liacopoulos, Dimitra; Pardon, Kevin H.; Sefton, Mark A. (1998-02-01). "Formation and Degradation of Furfuryl Alcohol, 5-Methylfurfuryl Alcohol, Vanillyl Alcohol, and Their Ethyl Ethers in Barrel-Aged Wines" (in en). Journal of Agricultural and Food Chemistry 46 (2): 657–663. doi:10.1021/jf970559r. ISSN 0021-8561. PMID 10554294. https://pubs.acs.org/doi/10.1021/jf970559r.
- ↑
- Sun, Guohan; An, Jiahuan; Hu, Hong; Li, Changzhi; Zuo, Songlin; Xia, Haian (2019). "Green catalytic synthesis of 5-methylfurfural by selective hydrogenolysis of 5-hydroxymethylfurfural over size-controlled Pd nanoparticle catalysts" (in en). Catalysis Science & Technology 9 (5): 1238–1244. doi:10.1039/C9CY00039A. ISSN 2044-4753. https://xlink.rsc.org/?DOI=C9CY00039A.
- Dong, Lin; Morales-Vidal, Jordi; Mu, Lili; Li, Licheng; López, Núria; Pérez-Ramírez, Javier; Chen, Zupeng (October 2023). "Selective hydrogenolysis of 5-hydroxymethylfurfural to 5-methylfurfural over Au/TiO2" (in en). Applied Catalysis B: Environmental 335. doi:10.1016/j.apcatb.2023.122893. https://linkinghub.elsevier.com/retrieve/pii/S0926337323005362.
- ↑ Feng, Yunchao; Li, Zheng; Long, Sishi; Sun, Yong; Tang, Xing; Zeng, Xianhai; Lin, Lu (2020). "Direct conversion of biomass derived l -rhamnose to 5-methylfurfural in water in high yield" (in en). Green Chemistry 22 (18): 5984–5988. doi:10.1039/D0GC02105A. ISSN 1463-9262. https://xlink.rsc.org/?DOI=D0GC02105A.
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