2-(ethoxymethyl)-5-methylfuran | 35901-19-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(ethoxymethyl)-5-methylfuran
• CAS: 35901-19-0
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: GXICAIPZEZBXCA-UHFFFAOYSA-N

物化性质

• 沸点：
  158.5±25.0 °C(Predicted)
• 密度：
  0.972±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(ethoxymethyl)-5-methylfuran 、 聚合甲醛 在 溶剂黄146 作用下， 反应 1.0h， 以9%的产率得到2-[5-(Ethoxymethyl)furan-2-yl]ethanol
  参考文献：
  名称：

  Pevzner, L. M.; Ignat'ev, V. M.; Golubkov, I. M., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 4.2, p. 757 - 759

  摘要：

  DOI：
• 作为产物：
  描述：

  5-甲基呋喃醛 在 sodium tetrahydroborate 作用下， 生成 2-(ethoxymethyl)-5-methylfuran
  参考文献：
  名称：

  Biomass conversion to diesel via the etherification of furanyl alcohols catalyzed by Amberlyst-15

  摘要：

  The etherification of furanyl alcohols produced from biomass-derived glucose and fructose has been a growing area of research for production of alternative diesel additives. We have determined that the Bronsted acidic resin catalyst, Amberlyst-15, is highly active and selective for the etherification of furanyl alcohols by both ethanol and butanol. The mechanism and kinetics of this reaction were investigated using 5-methylfurfuryl alcohol (MFA) as a probe molecule. Etherification of MFA was found to be first order in both the concentrations of furanyl alcohol and the acid sites. The mechanism of MFA etherification also holds for the etherification of 2,5-bis(hydroxymethyl)furan (BHMF) and 5-(hydroxymethyl)furfural (HMF). In the case of HMF, we find that acetalization of HMF precedes etherification in alcohol solutions. The apparent activation energy of furanyl alcohol etherification in ethanol and butanol solutions ranged from 17.0 to 26.3 kcal/mol. Electron donation/withdrawal at the 2 or 5 position of the furan ring in addition to solvent polarity was found to have significant effects on the rate of furanyl alcohol etherification. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jcat.2014.02.012

文献信息

• Copper-Zinc Alloy Nanopowder: A Robust Precious-Metal-Free Catalyst for the Conversion of 5-Hydroxymethylfurfural
  作者：Giovanni Bottari、Angela J. Kumalaputri、Krzysztof K. Krawczyk、Ben L. Feringa、Hero J. Heeres、Katalin Barta

  DOI：10.1002/cssc.201403453

  日期：2015.4.24

  CPME, with an excellent DMF yield of 90 %. Milder temperatures favor selective (95 %) formation of 2,5‐furandimethanol (FDM). The one‐pot conversion of fructose to valuable furan‐ethers was also explored. Recycling experiments for DMF production show remarkable catalyst stability. Transmission electron microscopy (TEM) characterization provides more insight into morphological changes of this intriguing

  发现不含贵金属的铜锌纳米合金（<150 nm）特别适合将5-羟甲基糠醛（HMF）高度选择性催化转化为潜在的生物燃料或化学构件。在20–30 bar H 2下于200–220°C的温度下，获得清洁合成的2,5-二甲基呋喃（DMF）和2,5-二甲基四氢呋喃（DMTHF）的混合产品，收率高达97％。也可以在CPME中转化10 wt％的HMF溶液，DMF产率高达90％。较温和的温度有利于选择性（95％）形成2,5-呋喃二甲醇（FDM）。还研究了将果糖从一锅转化为有价值的呋喃醚的方法。用于DMF生产的再循环实验显示出显着的催化剂稳定性。透射电子显微镜（TEM）表征提供了对这类有趣的材料在催化过程中形态变化的更多见解。
• [EN] METAL CATALYST AND HYDROGEN GAS FREE APPROACHES FOR SELECTIVE REDUCTION OF ALDEHYDE TO METHYL GROUP OF DIFFERENT SUBSTITUTED FURANS<br/>[FR] PROCÉDÉS SANS CATALYSEUR MÉTALLIQUE NI HYDROGÈNE GAZEUX POUR LA RÉDUCTION SÉLECTIVE D'ALDÉHYDE EN GROUPE MÉTHYLE DE DIFFÉRENTS FURANES SUBSTITUÉS
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2021165991A1

  公开（公告）日：2021-08-26

  The present invention relates to 5-methyl substituted furan compounds of general formula (I) and process for the preparation thereof: OR1R2 R3CH3(I) Particularly, the present invention relates to a metal catalyst and hydrogen gas free, atom-economy, highly selective and low-cost process for the preparation of methyl substituted furan compounds from different aldehyde substituted furan compounds.

  本发明涉及一般式(I)的5-甲基取代呋喃化合物及其制备方法：OR1R2 R3CH3(I)。特别地，本发明涉及一种金属催化剂和无氢气，原子经济，高选择性和低成本的方法，用于从不同醛基呋喃化合物制备甲基取代呋喃化合物。
• Selective Hydrogenation of 5-Ethoxymethylfurfural over Alumina-Supported Heterogeneous Catalysts
  作者：Erik-Jan Ras、Sergio Maisuls、Paul Haesakkers、Gert-Jan Gruter、Gadi Rothenberg

  DOI：10.1002/adsc.200900526

  日期：2009.12

  We report here the synthesis and testing of a set of 48 alumina-supported catalysts for hydrogenation of 5-ethoxymethylfurfural. This catalytic reaction is very important in the context of converting biomass to biofuels. The catalysts are composed of one main metal (gold, copper, iridium, nickel, palladium, platinum, rhodium, ruthenium) and one promoter metal (bismuth, chromium, iron, sodium, tin,

  我们在此报告了一组用于48种氧化铝负载的5-乙氧基甲基糠醛加氢催化剂的合成和测试。在将生物质转化为生物燃料的背景下，该催化反应非常重要。催化剂由一种主要金属（金，铜，铱，镍，钯，铂，铑，钌）和一种助催化剂金属（铋，铬，铁，钠，锡，钨）组成。使用16平行滴流式反应器，我们在各种条件下测试了所有48种催化剂组合。结果表明，底物转化率和产物选择性均对温度变化和溶剂效应敏感。使用铱/铬（Ir / Cr）催化剂可获得所需产物> 5-乙氧基甲基糠醇> 99％收率的最佳结果。
• Concurrent Anodic Cyanation and Methoxylation of Methylated Furans. Oxidation Potential and Reactivity, and Stereochemical Control of Addition
  作者：Kunihisa Yoshida、Takayuki Fueno

  DOI：10.1246/bcsj.60.229

  日期：1987.1

  The potentiostatic electrooxidation of a series of methyl-substituted furans was performed in MeOH that contains NaCN at a Pt anode in a divided cell. In all instances, the 1,4-additions of cyano and/or methoxyl group(s) across the furan ring were achieved. Replacement of an aromatic hydrogen by a cyano group occurred concurrently in some cases. The relative rates of cation radicals toward two different

  一系列甲基取代的呋喃的恒电位电氧化在含有 NaCN 的 MeOH 中进行，位于 Pt 阳极的分隔电池中。在所有情况下，都实现了氰基和/或甲氧基在呋喃环上的 1,4-加成。在某些情况下，芳族氢被氰基取代是同时发生的。在电极表面，阳离子自由基对两种不同亲核试剂（CN- 离子和溶剂 MeOH（或 MeO- 离子作为 CN- 离子和溶剂 MeOH 之间的平衡））的相对速率由以下的产率确定产品通过使用竞争反应的速率表达式。呋喃的相对反应性（以对数为单位）与其氧化电位之间存在线性相关性。电氧化形成的立体异构体的比例为 2，
• HYDROGENATION OF OXYGENATED MOLECULES FROM BIOMASS REFINING
  申请人：VIRDIA, INC.

  公开号：US20170088498A1

  公开（公告）日：2017-03-30

  The present disclosure relates to methods, processes, and systems for utilizing the dehydrogenation of 2-butanol for hydrogen consuming reactions of biomass or biomass-derived molecules. The present invention relates to methods, processes, and systems for utilizing the dehydrogenation of 2-butanol for hydrogen consuming hydrogenation, hydrogenolysis, or hydrodeoxygenation reactions of biomass or biomass-derived molecules.

  本公开涉及利用2-丁醇的脱氢作用用于生物质或生物质衍生分子的氢消耗反应的方法、过程和系统。本发明涉及利用2-丁醇的脱氢作用用于生物质或生物质衍生分子的氢消耗氢化、氢解或脱氧反应的方法、过程和系统。