5-propoxymethylfurfural | 1917-66-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-propoxymethylfurfural
• 英文别名: 5-(Propoxymethyl)furan-2-carbaldehyde
• CAS: 1917-66-4
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: GIOIMYYFBZQLCS-UHFFFAOYSA-N

物化性质

• 沸点：
  129-130 °C(Press: 15 Torr)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-propoxymethylfurfural 、 丙醇 生成 甲酸丙酯
  参考文献：
  名称：

  GARVES, KLAUS, BIOMASS ENERGY AND IND., LONDON; NEW YORK,(1987) C. 958-962

  摘要：

  DOI：
• 作为产物：
  描述：

  丙醇 、 5-羟甲基糠醛 在 sulfonic acid functionalized organic porous polymer 作用下， 反应 0.5h， 以75%的产率得到5-propoxymethylfurfural
  参考文献：
  名称：

  在磺化有机聚合物催化剂上从生物质衍生的 5-羟甲基糠醛高效合成 5-乙氧基甲基糠醛

  摘要：

  在此，我们研究了带有磺酸基团的功能化多孔有机聚合物 (PDVTA-SO 3 H) 在无溶剂条件下对 5-羟甲基糠醛 (HMF) 醚化为 5-乙氧基甲基糠醛 (EMF) 的催化潜力。PDVTA-SO 3 H 材料通过氯磺酸对多孔共聚物聚二乙烯基苯-共三烯丙基胺的后合成磺化合成。通过FT-IR、SEM、TG-DTG和N 2吸附等温线技术对PDVTA-SO 3 H的理化性质进行了表征。PDVTA-SO 3 H 具有高比表面积（591 m 2 g -1）和高密度的–SO3 H 基团(2.1 mmol g -1 )。通过Box-Behnken 响应面法优化反应条件在优化的条件下，PDVTA-SO 3 H催化剂表现出高效的催化活性，在110 ℃下30 min内HMF转化率为99.8%，EMF产率为87.5%。用过的PDVTA-SO 3 H催化剂很容易通过过滤回收并在循环运行中保持活性。

  DOI：

  10.1039/d0ra10307a

文献信息

• Preparation of potential biofuel 5-ethoxymethylfurfural and other 5-alkoxymethylfurfurals in the presence of oil shale ash
  作者：Indrek Viil、Aleksei Bredihhin、Uno Mäeorg、Lauri Vares

  DOI：10.1039/c3ra46570e

  日期：——

  5-Ethoxymethylfurfural (EMF) can be prepared from the corresponding halomethylfurfural and absolute ethanol in good yield. The use of significantly more affordable 96% ethanol results in formation of levulinic acid or its ester in considerable amount (up to 16%), which is difficult to separate from the desired EMF. In the present study we report that the addition of oil shale ash prevents the hydrolysis of the furan ring and enables the use of 96% ethanol with great success. The developed procedure is applicable to a wide range of aqueous alcohols, is operationally simple and utilizes an inexpensive basic ash, which is deposited in millions of tons per year. Notably, the basicity of the ash is decreased during the process, making its deposits less hazardous to the environment.

  5-乙氧甲基呋喃醛（EMF）可以通过将相应的卤甲基呋喃醛与无水乙醇反应制备，并获得良好的产率。使用成本显著更低的96%乙醇会导致产生相当数量的戊酸或其酯（高达16%），这使得从所需的EMF中分离戊酸变得困难。在本研究中，我们报告了添加油页岩灰可以防止呋喃环的水解，并成功使用96%乙醇。开发的程序适用于多种水相醇类，操作简单，并利用了一种廉价的基础灰分，该灰分每年沉积数百万吨。值得注意的是，灰分的碱性在过程中降低，因此其沉积物对环境的危害性减小。
• Conversion of fructose into 5-hydroxymethylfurfural and alkyl levulinates catalyzed by sulfonic acid-functionalized carbon materials
  作者：Ruliang Liu、Jinzhu Chen、Xing Huang、Limin Chen、Longlong Ma、Xinjun Li

  DOI：10.1039/c3gc41139g

  日期：——

  respectively, are obtained. The catalytic activities of C–SO3H for the conversions of fructose into both HMF and ethyl levulinate follow the order of their acid strength. The relationship between the catalytic activity and acid density of C–SO3H shows a linear correspondence in the fructose dehydration to HMF. The facile separation, ease of recovery, and high thermal stability make the developed C–SO3H efficient

  一系列磺酸官能化的碳材料（C–SO 3 H），包括聚对苯乙烯磺酸接枝的碳纳米管（CNT-PSSA），聚对苯乙烯磺酸接枝的碳纳米纤维（CNF-PSSA），苯磺酸接枝的CMK-5（CMK-5-BSA），以及 苯磺酸嫁接 碳纳米管 （CNT-BSA），已经研究了 果糖 脱水成 5-羟甲基糠醛 （HMF）和 果糖 酒精中毒到乙酰丙酸烷基酯。优化反应条件的研究，例如催化剂加载，反应时间和温度均已完成。在最佳条件下，高HMF和乙酰丙酸乙酯获得的产率分别高达89％和86％。C–SO 3 H催化转化为果糖 进入HMF和 乙酰丙酸乙酯遵循其酸强度的顺序。C–SO 3 H的催化活性与酸密度之间的关系在反应过程中呈线性对应关系。果糖脱水成HMF。简便的分离，易于回收和高热稳定性使已开发的C–SO 3 H高效，环保的催化材料可将生物质碳水化合物转化为精细化学品。
• Heterogeneous acidic TiO2 nanoparticles for efficient conversion of biomass derived carbohydrates
  作者：Chung-Hao Kuo、Altug S. Poyraz、Lei Jin、Yongtao Meng、Lakshitha Pahalagedara、Sheng-Yu Chen、David A. Kriz、Curtis Guild、Anton Gudz、Steven L. Suib

  DOI：10.1039/c3gc40909k

  日期：——

  Selective conversion of biomass derived carbohydrates into fine chemicals is of great significance for the replacement of petroleum feedstocks and the reduction of environmental impacts. Levulinic acid, 5-hydroxymethyl furfural (HMF) and their derivatives are recognized as important precursor candidates in a variety of different areas. In this study, the synthesis, characterization, and catalytic activity of acidic TiO2 nanoparticles in the conversion of biomass derived carbohydrates were explored. This catalyst was found to be highly effective for selective conversion to value-added products. The nanoparticles exhibited superior activity and selectivity towards methyl levulinate from fructose in comparison to current commercial catalysts. The conversion of fructose to methyl levulinate was achieved with 80% yield and high selectivity (up to 80%). Additionally, conversions of disaccharides and polysaccharides were studied. Further, the production of versatile valuable products such as levulinic esters, HMF, and HMF-derived ethers was demonstrated using the TiO2 nano-sized catalysts in different solvent systems.

  生物质衍生碳水化合物的选择性转化为精细化学品对替代石油原料和减少环境影响具有重要意义。戊酸、5-羟甲基糠醛（HMF）及其衍生物被认为是多种不同领域的重要前驱体候选物。本研究探讨了酸性TiO2纳米颗粒在生物质衍生碳水化合物转化中的合成、表征和催化活性。研究发现该催化剂在选择性转化为增值产品方面非常有效。与当前商业催化剂相比，这些纳米颗粒在果糖转化为甲基戊酸酯的活性和选择性方面表现出优越性。果糖转化为甲基戊酸酯的产率达到80%，且高选择性（高达80%）。此外，还研究了二糖和多糖的转化情况。进一步展示了在不同溶剂体系中使用TiO2纳米催化剂生产多种有价值产品，如戊酸酯、HMF和HMF衍生醚的可能性。
• Cascade of Liquid-Phase Catalytic Transfer Hydrogenation and Etherification of 5-Hydroxymethylfurfural to Potential Biodiesel Components over Lewis Acid Zeolites
  作者：Jungho Jae、Eyas Mahmoud、Raul F. Lobo、Dionisios G. Vlachos

  DOI：10.1002/cctc.201300978

  日期：2014.2

  reaction proceeds through the sequential transfer hydrogenation and etherification of HMF to 2,5‐bis(alkoxymethyl)furan, a potential biodiesel additive, catalyzed by a Lewis acid zeolite, such as Sn‐Beta or Zr‐Beta. An alcohol is used as a hydrogen donor and as a reactant in etherification. This cascade reaction can selectively produce high yields of the biodiesel additive (>80 % yield) from HMF with the

  我们报告了从生物质衍生的5-羟甲基糠醛（HMF）生产柴油的一步法过程。该反应通过将HMF依次转移加氢和醚化为2,5-双（烷氧基甲基）呋喃（一种潜在的生物柴油添加剂）进行，路易斯酸沸石如Sn-Beta或Zr-Beta催化该反应。醇用作氢供体和醚化中的反应物。这种级联反应可以选择性地从HMF，Sn-Beta催化剂和仲醇（例如2-丙醇和2-丁醇）中产生高产率的生物柴油添加剂（产率> 80％）。
• CONVERSION OF CARBOHYDRATES TO HYDROXYMETHYLFURFURAL (HMF) AND DERIVATIVES
  申请人：SANBORN Alexandra J.

  公开号：US20090156841A1

  公开（公告）日：2009-06-18

  A method of producing substantially pure HMF, HMF esters and other derivatives from a carbohydrate source by contacting the carbohydrate source with a solid phase catalyst. A carbohydrate starting material is heated in a solvent in a column and continuously flowed through a solid phase catalyst in the presence of an organic acid, or heated with the organic acid and a solid catalyst in solution to form a HMF ester. Heating without organic acid forms HMF. The resulting product is purified by filtration to remove the unreacted starting materials and catalyst. The HMF ester or a mixture of HMF and HMF ester may then be oxidized to 2,5-furandicarboxylic acid (FDCA) by combining the HMF ester with an organic acid, cobalt acetate, manganese acetate and sodium bromide under pressure. Alternatively, the HMF ester may be reduced to form a furan or tetrahydrofuran diol.

  一种从碳水化合物源直接生产几乎纯的HMF、HMF酯和其他衍生物的方法是将碳水化合物源与固相催化剂接触。碳水化合物起始物质在溶剂中加热于柱中，并在有机酸存在下通过固相催化剂连续流动，或者与有机酸和溶液中的固体催化剂一起加热以形成HMF酯。在无有机酸的情况下加热会形成HMF。通过过滤将产物纯化，去除未反应的起始物质和催化剂。然后，HMF酯或HMF和HMF酯的混合物可以氧化为2,5-呋喃二甲酸（FDCA），方法是将HMF酯与有机酸、醋酸钴、醋酸锰和溴化钠在压力下结合。另外，HMF酯可以还原形成呋喃或四氢呋喃二醇。