2-甲基四氢呋喃：修订间差异

2-甲基四氢呋喃
	IUPAC名; 2-Methyloxolane
别名	2-Methyltetrahydrofuran, 2-Methyl-THF
识别
CAS号	96-47-9（外消旋體）; 63798-13-0（R）; 63798-12-9（S）
PubChem	7301
ChemSpider	7028
SMILES	O1C(C)CCC1;
InChI	1/C5H10O/c1-5-3-2-4-6-5/h5H,2-4H2,1H3;
InChIKey	JWUJQDFVADABEY-UHFFFAOYAM
UN编号	2536
性质
化学式	C5H10O
摩尔质量	86.13 g·mol−1
密度	0.854 g/mL
熔点	-136 °C（137 K）
沸点	80.2 °C（353 K）
危险性
	GHS危险性符号;
GHS提示词	警告
H-术语	H225, H302, H315, H318, H319, H335, H336
P-术语	P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+312, P302+352, P303+361+353
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

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2022年2月7日 (一) 02:55的版本

2-甲基四氫呋喃 (簡稱：2-MeTHF)是一具分子式C₅H₁₀O的有機化合物。其在常溫常壓下為一高度可燃的流動液體。相較於四氫呋喃，其可用於更高溫的化學反應，且不與水互溶，故2-甲基四氫呋喃可作為四氫呋喃的替代物。 2-甲基四氫呋喃可由醣類生成糠醛中間產物後催化氫化製得。2-甲基四氫呋喃有時被售為生物燃料.^[1]

結構和性質

2-甲基四氫呋喃在水中溶解度會隨溫度的上升而減低，為較少見的性質。^[2] 與四氫呋喃相似，2-甲基四氫呋喃也可在有機金屬反應中作為路易斯鹼。^[3] 2-甲基四氫呋喃的合成通常會生成外消旋體。

製備方式

2-甲基四氫呋喃通常由糠醛的催化氫化製得。^[4]

${\ce {OC4H3CHO + 4 H2-> OC4H7CH3 + H2O}}$

糠醛可由生物質中酸催化分解五碳醣單體組成的多醣產生。因此, 2-甲基四氫呋喃的原料為可再生，富有纖維素、半纖維素和木質素的生物質, 如玉米穗軸或甘蔗渣，以及其他植物和農業廢棄物。^[5]

2-甲基四氫呋喃也可以乙醯丙酸作為起始原料. 經環化和還原反應後可製得 γ-戊內酯:

γ-戊內酯可被氫化成1,4-戊二醇, 並經脫水後生成 2-甲基四氫呋喃:

參考資料

^ Leal Silva, Jean Felipe; Mariano, Adriano Pinto; Maciel Filho, Rubens. Economic potential of 2-methyltetrahydrofuran (MTHF) and ethyl levulinate (EL) produced from hemicelluloses-derived furfural. Biomass and Bioenergy. 2018, 119 (December 2018): 492–502. doi:10.1016/j.biombioe.2018.10.008.
^ Sicaire, Anne-Gaëlle; Vian, Maryline Abert; Filly, Aurore; Li, Ying; Bily, Antoine; Chemat, Farid, Chemat, Farid; Vian, Maryline Abert , 编, 2-Methyltetrahydrofuran: Main Properties, Production Processes, and Application in Extraction of Natural Products, Alternative Solvents for Natural Products Extraction (Berlin, Heidelberg: Springer Berlin Heidelberg), 2014: 253–268, ISBN 978-3-662-43627-1, doi:10.1007/978-3-662-43628-8_12 （英语）
^ Aycock, David F. Solvent Applications of 2-Methyltetrahydrofuran in Organometallic and Biphasic Reactions. Org. Process Res. Dev. 2007, 11: 156–159. doi:10.1021/op060155c.
^ Huber, GW; Iborra, S; Corma, A. Synthesis of transportation fuels from biomass: chemistry, catalysts, and engineering. Chem. Rev. September 2006, 106 (9): 4044–98. PMID 16967928. doi:10.1021/cr068360d. ref 306
^ Hoydonckx, H. E.; Van Rhijn, W. M.; Van Rhijn, W.; De Vos, D. E.; Jacobs, P. A., Furfural and Derivatives, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a12_119.pub2

[1] Leal Silva, Jean Felipe; Mariano, Adriano Pinto; Maciel Filho, Rubens. Economic potential of 2-methyltetrahydrofuran (MTHF) and ethyl levulinate (EL) produced from hemicelluloses-derived furfural. Biomass and Bioenergy. 2018, 119 (December 2018): 492–502. doi:10.1016/j.biombioe.2018.10.008.

[2] Sicaire, Anne-Gaëlle; Vian, Maryline Abert; Filly, Aurore; Li, Ying; Bily, Antoine; Chemat, Farid, Chemat, Farid; Vian, Maryline Abert , 编, 2-Methyltetrahydrofuran: Main Properties, Production Processes, and Application in Extraction of Natural Products, Alternative Solvents for Natural Products Extraction (Berlin, Heidelberg: Springer Berlin Heidelberg), 2014: 253–268, ISBN 978-3-662-43627-1, doi:10.1007/978-3-662-43628-8_12 （英语）

[aycock-3] Aycock, David F. Solvent Applications of 2-Methyltetrahydrofuran in Organometallic and Biphasic Reactions. Org. Process Res. Dev. 2007, 11: 156–159. doi:10.1021/op060155c.

[4] Huber, GW; Iborra, S; Corma, A. Synthesis of transportation fuels from biomass: chemistry, catalysts, and engineering. Chem. Rev. September 2006, 106 (9): 4044–98. PMID 16967928. doi:10.1021/cr068360d. ref 306

[5] Hoydonckx, H. E.; Van Rhijn, W. M.; Van Rhijn, W.; De Vos, D. E.; Jacobs, P. A., Furfural and Derivatives, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a12_119.pub2

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