4-Hydroxy-4-[5-(hydroxymethyl)furan-2-yl]butan-2-one | 1208070-49-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Hydroxy-4-[5-(hydroxymethyl)furan-2-yl]butan-2-one
• CAS: 1208070-49-8
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: IUEPIXDBMFTMNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-羟甲基糠醛 、 丙酮 在 zirconium carbonate 作用下， 以 水 为溶剂， 反应 24.0h， 生成 4-Hydroxy-4-[5-(hydroxymethyl)furan-2-yl]butan-2-one
  参考文献：
  名称：

  固体碱和双功能金属酸催化剂催化将5-羟基甲基糠醛催化降解为生物燃料

  摘要：

  设计和合成有效的非均相催化剂，以将生物质中间体转化为长链烃前体，然后将其脱氧为烃，是将木质纤维素升级为馏分馏分型生物燃料的可行策略。本文中，我们报告了将5-羟甲基糠醛（HMF）升级为高产率和高选择性的C 9和C 11燃料的两步过程。第一步涉及将HMF和丙酮与耐水的固体碱催化剂碳酸锆（Zr（CO 3）x）进行羟醛缩合反应，在几乎100％的HMF转化率下，得到高选择性的92％C 9-羟醛产物。合成后的Zr（CO 3）x通过阐明其结构性质的几种分析方法进行了分析。Zr（CO 3）x的可回收性研究表明，在运行120小时后的五个连续循环中，Zr（CO 3）的活性损失可忽略不计。第一步中分离出的醛醇产物用双功能Pd /Zeolite-β催化剂在乙醇中加氢脱氧，表明醛醇产物分别以40％和56％的选择性定量转化为正壬烷和1-乙氧基壬烷。我们首次在本文中首次报道了低氧含量柴油范围的1-乙氧基壬烷，它是通过乙

  DOI：

  10.1002/cssc.201501136

文献信息

• [EN] BIOREFINING COMPOUNDS AND ORGANOCATALYTIC UPGRADING METHODS<br/>[FR] BIORAFFINAGE DE COMPOSÉS ET PROCÉDÉS DE VALORISATION PAR ORGANOCATALYSE
  申请人：CHEN EUGENE

  公开号：WO2014008301A1

  公开（公告）日：2014-01-09

  The invention provides new methods for the direct umpolung self-condensation of 5-hydroxymethylfurfural (HMF) by organocatalysis, thereby upgrading the readily available substrate into 5,5'-di(hydroxymethyl) furoin (DHMF). While many efficient catalyst systems have been developed for conversion of plant biomass resources into HMF, the invention now provides methods to convert such nonfood biomass directly into DHMF by a simple process as described herein. The invention also provides highly effective new methods for upgrading other biomass furaldehydes and related compound to liquid fuels. The methods include the organocatalytic self-condensation (umpolung) of biomass furaldehydes into (C8-C12)furoin intermediates, followed by hydrogenation, etherification or esterification into oxygenated biodiesel, or hydrodeoxygenation by metal-acid tandem catalysis into premium hydrocarbon fuels.

  该发明提供了一种新的方法，通过有机催化实现5-羟甲基糠醛（HMF）的直接反极化自缩合，从而将易得的底物升级为5,5'-二(羟甲基)呋喃（DHMF）。尽管已经开发了许多高效的催化剂系统将植物生物质资源转化为HMF，但该发明现在提供了将这种非食用生物质直接转化为DHMF的方法，通过如下所述的简单过程。该发明还提供了一种高效的新方法，用于将其他生物质呋喃醛和相关化合物升级为液体燃料。这些方法包括有机催化的生物质呋喃醛自缩合（反极化）成为（C8-C12）呋喃中间体，随后通过加氢、醚化或酯化制备含氧生物柴油，或通过金属酸串联催化的脱氧制备高级烃燃料。
• PRODUCTION OF LIQUID FUELS (SYLVAN-LIQUID-FUELS) FROM 2-METHYLFURAN
  申请人：CORMA CANÓS Avelino

  公开号：US20120316372A1

  公开（公告）日：2012-12-13

  The present invention describes a procedure for the production of liquid fuel having a content high in alkanes and low in oxygenated compounds, comprising as a minimum: —a first step of alkylation of 2-methylfuran (commonly denominated Sylvan) with a furan alcohol 2 having the formula: (2), wherein R 1 is H or an aliphatic or aromatic or heteroaromatic moiety, R 2 is H or an aliphatic or aromatic or heteroaromatic moiety, and R 3 is H, hydroxymethyl or an aliphatic or aromatic or heteroaromatic moiety, in the presence of a catalyst, —a second step of hydrogenation and dehydration of the compound obtained in step 1 in the presence of hydrogen, utilising suitable hydrogenation and dehydration catalysts.

  本发明描述了一种生产液体燃料的程序，其含有高烷烃含量和低含氧化合物，包括至少以下步骤：—使用催化剂对2-甲基呋喃（通常称为Sylvan）与具有以下式的呋喃醇2进行烷基化的第一步骤：(2)，其中R1为H或脂肪族或芳香族或杂环芳基，R2为H或脂肪族或芳香族或杂环芳基，R3为H、羟甲基或脂肪族或芳香族或杂环芳基，在氢气存在下，—在适当的氢化和脱水催化剂存在下，对步骤1中得到的化合物进行氢化和脱水的第二步骤。
• METHOD FOR CONVERTING BIOMASS INTO LIQUID FUEL
  申请人：Consejo Superior De Investigaciones Cientificas (CSIC)

  公开号：US20130158315A1

  公开（公告）日：2013-06-20

  The invention relates to a method for producing liquid fuel having a high alkane content and a low oxygenized compound content, said method comprising at least: a first step of treating 2-methylfurane with a catalyst and water in reaction conditions in order to form a mixture of products with at least ten carbon atoms; and a second step of catalytic hydrogenation and dehydration of the product or the mixture obtained in step 1, using suitable hydrogenation and dehydration catalysts.

  本发明涉及一种制备高烷烃含量和低含氧化合物的液体燃料的方法，该方法至少包括以下步骤：第一步，在反应条件下使用催化剂和水处理2-甲基呋喃，以形成至少十个碳原子的产品混合物；第二步，使用适当的加氢和脱水催化剂对步骤1中获得的产物或混合物进行催化加氢和脱水。
• BIOREFINING COMPOUNDS AND ORGANOCATALYTIC UPGRADING METHODS
  申请人：Colorado State University Research Foundation

  公开号：US20140007497A1

  公开（公告）日：2014-01-09

  The invention provides new methods for the direct umpolung self-condensation of 5-hydroxymethylfurfural (HMF) by organocatalysis, thereby upgrading the readily available substrate into 5,5′-di(hydroxymethyl)furoin (DHMF). While many efficient catalyst systems have been developed for conversion of plant biomass resources into HMF, the invention now provides methods to convert such nonfood biomass directly into DHMF by a simple process as described herein. The invention also provides highly effective new methods for upgrading other biomass furaldehydes and related compound to liquid fuels. The methods include the organocatalytic self-condensation (umpolung) of biomass furaldehydes into (C 8 -C 12 )furoin intermediates, followed by hydrogenation, etherification or esterification into oxygenated biodiesel, or hydrodeoxygenation by metal-acid tandem catalysis into premium hydrocarbon fuels.

  本发明提供了一种新的方法，通过有机催化直接进行5-羟甲基糠醛（HMF）的自反极化自缩合，将易得到的底物升级为5,5'-二（羟甲基）呋喃（DHMF）。虽然已经开发出许多有效的催化剂体系将植物生物质资源转化为HMF，但本发明现在提供了将这种非食用生物质直接转化为DHMF的方法，这是通过本文所描述的简单过程实现的。本发明还提供了将其他生物质呋醛和相关化合物升级为液体燃料的高效新方法。这些方法包括有机催化的生物质呋醛自缩合（反极化）成（C8-C12）呋喃中间体，然后通过氢化、醚化或酯化转化为含氧生物柴油，或通过金属-酸串联催化剂的脱氧反应转化为高品质烃类燃料。
• Catalytic properties of dendron–OMS hybrids
  作者：Qingqing Wang、Victor Varela Guerrero、Anirban Ghosh、Seunguk Yeu、Jonathan D. Lunn、Daniel F. Shantz

  DOI：10.1016/j.jcat.2009.10.009

  日期：2010.1

  The synthesis and catalytic testing of several dendron-ordered mesoporous silica hybrids are reported. These materials are active in both the nitroaldol (Henry) reaction and the transesterification of glyceryl tributyrate to afford methyl esters. In both reactions it is observed that dendrons terminated with primary amines are more catalytically active than samples containing dendrons terminated with secondary amines. On a mmol nitrogen per gram of silica basis, the first generation dendrons are the most active for both chemistries, and the SBA-15 samples display a higher activity than the MCM-41 samples. The pore-size effect observed is consistent with significant diffusion resistance in the MCM-41 samples. The activity trend observed in the SBA-15 materials is consistent with decreased cooperative effects between the amines and surface silanols as the dendrons become larger. Clear trends are observed indicating that higher generation dendrons are more selective to alcohol formation in the Henry reaction. The dendron catalysts are much more active and stable than simple amines attached to silica in the transesterification of triglycerides. Preliminary results shown indicate that these materials can also catalyze more demanding chemistries, an example of which is the Aldol condensation of 5-(hydroxymethyl)furfural and acetone. The results shown indicate that dendron-OMS hybrids can serve as effective solid base catalysts for a diverse range of chemistries. (c) 2009 Elsevier Inc. All rights reserved.