BMFDBA | 1379772-47-0

• 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: BMFDBA
• 英文别名: 5-(butoxymethyl)furfural dibutyl acetal；5-(dibutoxymethyl)-2-furanbutanol
• CAS: 1379772-47-0
• 化学式: C₁₈H₃₂O₄
• 分子量: 312.45
• InChiKey: GCPPNOMCOPWLNB-UHFFFAOYSA-N

物化性质

• 沸点：
  341.9±37.0 °C(Predicted)
• 密度：
  0.968±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  22.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  40.83
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  5-羟甲基糠醛 、 正丁醇 在 Amberlyst 15 作用下， 生成 BMFDBA
  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

• Cascade Reductive Etherification of Bioderived Aldehydes over Zr-Based Catalysts
  作者：Suhas Shinde、Chandrashekhar Rode

  DOI：10.1002/cssc.201701275

  日期：2017.10.23

  value‐added ethers from bioderived aldehydes. Etherification of 5‐(hydroxymethyl)furfural with different aliphatic alcohols over acidic Zr–montmorillonite (Zr‐Mont) catalyst produced a mixture of 5‐(alkoxymethyl)furfural and 2‐(dialkoxymethyl)‐5‐(alkoxymethyl)furan. The latter was selectively converted back into 5‐(alkoxymethyl)furfural by treating it with water over the same catalyst. The synthesis of 2

  已开发出一种有效的单锅催化级联序列，用于从生物衍生的醛生产增值醚。在酸性Zr-蒙脱石（Zr-Mont）催化剂上用不同的脂肪醇将5-（羟甲基）糠醛醚化，生成了5-（烷氧基甲基）糠醛和2-（二烷氧基甲基）-5-（烷氧基甲基）呋喃的混合物。通过在同一催化剂上用水处理，将后者选择性地转化回5-（烷氧基甲基）糠醛。通过在酸性Zr-Mont和电荷转移加氢催化剂[ZrO（OH）2的组合）上进行的醚化，转移加氢和再醚化的级联序列，完成了2,5-双（烷氧基甲基）呋喃的合成。]。进一步探索了这种催化剂组合物，以将2-糠醛级联转化为2-（烷氧基甲基）呋喃。然后，该策略的范围扩大到了木质素衍生的芳醛的还原醚化反应，从而以> 80％的收率获得了各自的苄基醚。此外，Zr-Mont和ZrO（OH）2的混合物不会相互破坏，这通过再循环实验和XRD分析得到了证明。两种催化剂均使用BET，程序升温的NH 3和CO 2脱附，吡
• A Continuous Flow Strategy for the Coupled Transfer Hydrogenation and Etherification of 5-(Hydroxymethyl)furfural using Lewis Acid Zeolites
  作者：Jennifer D. Lewis、Stijn Van de Vyver、Anthony J. Crisci、William R. Gunther、Vladimir K. Michaelis、Robert G. Griffin、Yuriy Román-Leshkov

  DOI：10.1002/cssc.201402100

  日期：2014.8

  Hf‐, Zr‐ and Sn‐Beta zeolites effectively catalyze the coupled transfer hydrogenation and etherification of 5‐(hydroxymethyl)furfural with primary and secondary alcohols into 2,5‐bis(alkoxymethyl)furans, thus making it possible to generate renewable fuel additives without the use of external hydrogen sources or precious metals. Continuous flow experiments reveal nonuniform changes in the relative deactivation

  Hf-，Zr-和Sn-Beta沸石可有效催化5-（羟甲基）糠醛与伯醇和仲醇的偶合转移加氢和醚化反应成2,5-双（烷氧基甲基）呋喃，从而可产生可再生燃料添加剂无需使用外部氢源或贵金属。连续流动实验揭示了转移氢化和醚化反应的相对失活速率的不均匀变化，这会影响观察到的产物随时间的分布。我们发现，催化剂在醚化步骤中经历了急剧的失活，同时保持了转移氢化步骤的催化活性。119锡和29Si魔角旋转（MAS）NMR研究表明，这种失活可以归因于金属部位局部环境的变化。通过研究各种醇和水浓度对催化反应性的影响，获得了更多的见解。
• Etherification and reductive etherification of 5-(hydroxymethyl)furfural: 5-(alkoxymethyl)furfurals and 2,5-bis(alkoxymethyl)furans as potential bio-diesel candidates
  作者：Madhesan Balakrishnan、Eric R. Sacia、Alexis T. Bell

  DOI：10.1039/c2gc35102a

  日期：——

  A low energy intensive process for the production of diesel fuel has been delineated from both 5-(hydroxymethyl)furfural (HMF) and its sugar precursor D-(–)-fructose. Alcoholic solutions of the above produced a mixture of potential bio-diesel candidates namely, 5-(alkoxymethyl)furfural, 5-(alkoxymethyl)furfural dialkylacetal, and alkyl levulinate, in the presence of solid acid catalysts. Sulfonic acid

  一种低能耗的柴油生产工艺 燃料 两者都已被划定 5-（羟甲基）糠醛 （HMF）及其糖前体 D -（–）-果糖。上述的醇溶液在固体酸存在下产生了潜在的生物柴油候选物的混合物，即5-（烷氧基甲基）糠醛，5-（烷氧基甲基）糠醛二烷基缩醛和乙酰丙酸烷基酯。催化剂。磺酸官能化树脂Amberlyst-15和Dowex DR2030对这些反应显示出卓越的反应性和选择性。通过顺序还原/醚化和一锅还原醚化工艺，已经优化了另一种潜在的柴油候选2,5,2-双（烷氧基甲基）呋喃的生产。在金属催化期间氢化 对于HMF而言，铂显示出对降低H2O的唯一选择性。 羰HMF的功能。Al 2 O 3上同时支持Pt和Pt / Sn 催化剂已针对HMF生产2,5-双（烷氧基甲基）呋喃进行了优化。在这些过程中观察到的中间体的基础上，对醚化和还原性醚化的反应机理进行了详细讨论。
• Indium(III) triflate promoted synthesis of alkyl levulinates from furyl alcohols and furyl aldehydes
  作者：Jacqueline R. Kean、Andrew E. Graham

  DOI：10.1016/j.catcom.2014.10.013

  日期：2015.1

  A facile protocol for the alcoholysis of furfulyl alcohol into levulinate esters has been developed employing low catalyst loadings of indium(III) triflate. This method provides a rapid and efficient route for the synthesis of these useful materials. The alcoholysis reactions of 5-hydroxymethylfurfural (HMF), furfural and furfural dimethylacetal were also investigated under these reaction conditions. (C) 2014 Elsevier B.V. All rights reserved.