查看“︁2-甲基四氢呋喃”︁的源代码

{{Chembox
| Watchedfields = changed
| verifiedrevid = 477214694
| ImageFile = Methyltetrahydrofuran.svg
| ImageSize = 150px
| ImageAlt =
| PIN = 2-Methyloxolane
| OtherNames = 2-Methyltetrahydrofuran, 2-Methyl-THF
|Section1={{Chembox Identifiers
| index_label    = 
| index1_label   = 
| index2_label   = 
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7028
| InChI = 1/C5H10O/c1-5-3-2-4-6-5/h5H,2-4H2,1H3
| InChIKey = JWUJQDFVADABEY-UHFFFAOYAM
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C5H10O/c1-5-3-2-4-6-5/h5H,2-4H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JWUJQDFVADABEY-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo1 = 96-47-9 
|CASNo1_comment=[[外消旋體]]
| CASNo2 = 63798-13-0
|CASNo2_comment= ''R''
|CASNo3_comment=''S''
| CASNo3 = 63798-12-9 
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = FCD0VD8ALF
| PubChem = 7301
| EC_number = 202-507-4
| UNNumber = 2536
| ChEMBL = 1580503
| DTXSID = DTXSID9030258
| SMILES = O1C(C)CCC1
}}
|Section2={{Chembox Properties
| C=5 | H=10 | O=1
| MolarMass =
| Appearance =
| Density = 0.854 g/mL
| MeltingPtC = -136
| Melting_notes = 來源：<ref name = aycock/>
| BoilingPtC = 80.2
| Boiling_notes = 來源：<ref name = aycock/>
| Solubility = }}
|Section3={{Chembox Hazards
| ExternalMSDS = [http://msds.chem.ox.ac.uk/ME/2-methyltetrahydrofuran.html External MSDS]
| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS07}}
| GHSSignalWord =警告
| HPhrases = {{H-phrases|225|302|315|318|319|335|336}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|270|271|280|301+312|302+352|303+361+353|304+340|305+351+338|310|312|321|330|332+313|337+313|362|370+378|403+233|403+235|405|501}}
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}

'''2-甲基四氫呋喃''' (簡稱：2-MeTHF)是具有[[分子式]][[C5H10O|C<sub>5</sub>H<sub>10</sub>O]]的[[有機化合物]]。其在常溫常壓下為高度易燃的流動液體，相較於[[四氫呋喃]]，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在特定應用中的替代物。 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]]。<ref>{{cite journal |last1=Leal Silva |first1=Jean Felipe |last2=Mariano |first2=Adriano Pinto |last3=Maciel Filho |first3=Rubens |title=Economic potential of 2-methyltetrahydrofuran (MTHF) and ethyl levulinate (EL) produced from hemicelluloses-derived furfural |journal=Biomass and Bioenergy |volume=119 |issue=December 2018 |pages=492–502 |doi=10.1016/j.biombioe.2018.10.008 |year=2018}}</ref>

==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。<ref>{{Citation|last1=Sicaire|first1=Anne-Gaëlle|title=2-Methyltetrahydrofuran: Main Properties, Production Processes, and Application in Extraction of Natural Products|date=2014|work=Alternative Solvents for Natural Products Extraction|pages=253–268|editor-last=Chemat|editor-first=Farid|place=Berlin, Heidelberg|publisher=Springer Berlin Heidelberg|language=en|doi=10.1007/978-3-662-43628-8_12|isbn=978-3-662-43627-1|last2=Vian|first2=Maryline Abert|last3=Filly|first3=Aurore|last4=Li|first4=Ying|last5=Bily|first5=Antoine|last6=Chemat|first6=Farid|editor2-last=Vian|editor2-first=Maryline Abert}}</ref> 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]]。<ref name = aycock>{{cite journal | author = Aycock, David F. | title = Solvent Applications of 2-Methyltetrahydrofuran in Organometallic and Biphasic Reactions | journal = [[Org. Process Res. Dev.]] | year = 2007 | volume = 11 | pages = 156–159 | doi = 10.1021/op060155c}}</ref> 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。<ref>{{cite journal | doi=10.1021/cr068360d | pmid=16967928 | volume=106 | title=Synthesis of transportation fuels from biomass: chemistry, catalysts, and engineering | date=September 2006 | journal=Chem. Rev. | pages=4044–98 | last1=Huber | first1=GW | last2=Iborra | first2=S | last3=Corma | first3=A | issue=9 | url=https://works.bepress.com/cgi/viewcontent.cgi?article=1058&context=george_huber | access-date=2022-02-07 | archive-date=2023-03-26 | archive-url=https://web.archive.org/web/20230326024927/https://works.bepress.com/cgi/viewcontent.cgi?article=1058&context=george_huber | dead-url=no }} ref 306</ref>

<chem>OC4H3CHO  + 4 H2-> OC4H7CH3   + H2O </chem>

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。<ref>{{Ullmann | author = Hoydonckx, H. E. | author2 = Van Rhijn, W. M. | author3 = Van Rhijn, W. | author4 = De Vos, D. E. | author5 = Jacobs, P. A. | title = Furfural and Derivatives | doi = 10.1002/14356007.a12_119.pub2}}</ref>

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]]:<!-- {{doi|10.1021/cr068360d}} p4084 and ref 294, and also refs in image-page -->

:[[File:Cyclization of levulinic acid.svg]]

[[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:

:[[File:Reaction of Valerolactone to 2Me-THF.svg]]

==應用==
2-甲基四氫呋喃主要作為四氫呋喃的高沸點替代溶劑，也作為二次鋰電池中的電解質和替代燃料的成分。它是用於低溫反應的重要[[溶劑]]。2-甲基四氫呋喃在低溫下形成一種玻璃狀固體而不會結晶，因此經常用作在-196°C下進行光譜研究的溶劑。<ref name = aycock/>

2-甲基四氫呋喃的其他常見用途是作為有機金屬和兩相化學過程中使用的[[格氏試劑]]的溶劑，因為2-甲基四氫呋喃中的[[氧]]原子能夠與格氏試劑的[[鎂]]離子組分或共沸乾燥產物[[配位]]。使用2-甲基四氫呋喃可明確分離有機相和水相，故它是一種常用但更昂貴的四氫呋喃替代品。

2-甲基四氫呋喃被[[美國能源部]]批准為汽油添加劑。糠醛和其他呋喃基化合物（[[糠醇]]、[[2-甲基呋喃]]、[[四氫糠醇]]）具有聚合傾向，並且相當易揮發。然而，2-甲基四氫呋喃本身更穩定且揮發性更低，因此適合用作發動機燃料。

2-甲基四氫呋喃已被推廣為四氫呋喃的生態低危害替代品。<ref>{{cite web |url=https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/115/677/greener_solvent_alternatives.pdf |title=Greener Solvent Alternatives – Brochure |website=Sigmaaldrich.com |date= |accessdate=2010-02-15 |archive-date=2022-02-11 |archive-url=https://web.archive.org/web/20220211150905/https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/115/677/greener_solvent_alternatives.pdf }}</ref>雖然2-甲基四氫呋喃更昂貴，但它可以在整體合成過程中帶來更大的經濟性。2-甲基四氫呋喃具有介於[[二乙醚]]和四氫呋喃之間的溶劑性能，具有有限的水溶性，並且在蒸餾時與水形成[[共沸物]]。其較低的熔點使其可用於較低溫度的反應，其相對於四氫呋喃較高的沸點允許在較高溫度下進行[[迴流]]。

==參考資料==
{{reflist}}
==擴展閱讀==
* {{cite journal | author = Zheng, Hong-Yan | title = Towards understanding the reaction pathway in vapour phase hydrogenation of furfural to 2-methylfuran | journal =  Journal of Molecular Catalysis A: Chemical| doi = 10.1016/j.molcata.2005.10.003 | year = 2006 | last2 = Zhu | first2 = Yu-Lei | last3 = Teng | first3 = Bo-Tao | last4 = Bai | first4 = Zong-Qing | last5 = Zhang | first5 = Cheng-Hua | last6 = Xiang | first6 = Hong-Wei | last7 = Li | first7 = Yong-Wang | volume = 246 | issue = 1–2 | pages = 18–23}}

[[Category:醚類溶劑]]
[[Category:四氫呋喃]]