5-(Hydroxymethyl)-5-methylfuran-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 5-(Hydroxymethyl)-5-methylfuran-2-one
• 化学式: C₆H₈O₃
• 分子量: 128.13
• InChiKey: YWBPYSCGWZUZTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

文献信息

• [EN] CATALYTIC SYNTHESIS OF REDUCED FURAN DERIVATIVES<br/>[FR] SYNTHÈSE CATALYTIQUE DE DÉRIVÉS DE FURANE RÉDUITS
  申请人：ARCHER DANIELS MIDLAND CO

  公开号：WO2014175989A1

  公开（公告）日：2014-10-30

  The present invention relates to catalytic synthesis of furan derivatives from alkoxymethylfurfural ethers or acyloxymethylfurfural esters. More particularly, the invention pertains to furan derivatives obtained by use of a multifunctional catalyst system to carry out both hydrogenation of furan starting material and hydrolysis of the reduced furan derivative in a single reaction. The process allows recovering and recycling of alcohol or acid from the reaction product.

  本发明涉及利用多功能催化剂系统从烷氧甲基糠醛醚或酰氧甲基糠醛酯合成呋喃衍生物。更具体地，该发明涉及通过使用多功能催化剂系统，在单一反应中既进行糠醛起始原料的加氢，又进行还原后的呋喃衍生物的水解，从而获得呋喃衍生物。该过程允许从反应产物中回收和循环利用醇或酸。
• [EN] SYNTHESIS OF DICARBAMATES FROM REDUCTION PRODUCTS OF 2-HYDROXYMETHYL-5-FURUFURAL (HMF) AND DERIVATIVES THEREOF<br/>[FR] SYNTHÈSE DE DICARBAMATES À PARTIR DE PRODUITS DE RÉDUCTION DE 2-HYDROXYMÉTHYL-5-FURFURAL (HMF) ET DE LEURS DÉRIVÉS
  申请人：ARCHER DANIELS MIDLAND CO

  公开号：WO2014200636A1

  公开（公告）日：2014-12-18

  Dicarbamates of the reduction products of 2-hydroxymethyl-5-furfural (HMF) and a method of preparing the same are described. The method involves reacting a mixture of an isohexide and a cynate salt in a non-aqueous solvent, with a miscible acid having a pKa of about 3.7 or less. The dicarbamates of HMF-reduction products can serve as precursor materials from which various derivative compounds can be synthesized.

  描述了2-羟甲基-5-呋喃甲醛（HMF）还原产物的二氨基甲酸酯及其制备方法。该方法涉及在非水溶剂中，将异己糖和氰酸盐的混合物与一个pKa约为3.7或更低的可混酸反应。HMF还原产物的二氨基甲酸酯可以作为前体材料，用于合成各种衍生化合物。
• 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。
• SPRAY OXIDATION PROCESS FOR PRODUCING 2,5-FURANDICARBOXYLIC ACID FROM HYDROXYMETHYLFURFURAL
  申请人：Subramaniam Bala

  公开号：US20150183755A1

  公开（公告）日：2015-07-02

  A process is provided for carrying out an oxidation on a sprayable feed including a furanic substrate to be oxidized and a catalytically effective combination of cobalt, manganese, and bromide components for catalyzing the oxidation of the furanic substrate, which process comprises spraying the feed into a reactor vessel as a mist, supplying an oxidant, reacting the furanic substrate and the oxidant, and managing the exothermic temperature rise due to the reaction through a selection and control of the operating pressure within the reactor vessel. A crude dehydration product from the dehydration of fructose, glucose or both, including 5-hydroxymethylfurfural, can be directly oxidized by the process to produce 2,5-furandicarboxylic acid in surprisingly increased yields.

  提供一种在可喷雾的香豆素基质和催化剂组合（包括钴、锰和溴化物组分）中进行氧化反应的方法，该方法包括将香豆素基质作为雾状物喷入反应器中，提供氧化剂，使香豆素基质和氧化剂反应，并通过选择和控制反应器内的操作压力来管理由反应引起的放热温度升高。通过该方法，可以直接将果糖、葡萄糖或两者的脱水产物（包括5-羟甲基糠醛）氧化成2,5-呋喃二甲酸，其收率惊人地提高。
• Conversion of carbohydrates to hydroxymethylfurfural (HMF) and derivatives
  申请人：Archer-Daniels-Midland Company

  公开号：EP2423205A1

  公开（公告）日：2012-02-29

  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.

  一种通过使碳水化合物源与固相催化剂接触，从碳水化合物源生产基本纯净的 HMF、HMF 酯和其他衍生物的方法。碳水化合物起始原料在柱中的溶剂中加热，并在有机酸存在下连续流过固相催化剂，或在溶液中与有机酸和固相催化剂一起加热以形成 HMF 酯。在不使用有机酸的情况下加热则会形成 HMF。所得产物通过过滤进行提纯，以除去未反应的起始原料和催化剂。然后，将 HMF 酯与有机酸、醋酸钴、醋酸锰和溴化钠加压混合，可将 HMF 酯或 HMF 和 HMF 酯的混合物氧化成 2,5-呋喃二甲酸（FDCA）。另一种方法是将 HMF 酯还原成呋喃或四氢呋喃二醇。