WO2015056270A1 - Procédé de préparation d'acide 2,5 furane dicarboxylique - Google Patents

Procédé de préparation d'acide 2,5 furane dicarboxylique Download PDF

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Publication number
WO2015056270A1
WO2015056270A1 PCT/IN2013/000629 IN2013000629W WO2015056270A1 WO 2015056270 A1 WO2015056270 A1 WO 2015056270A1 IN 2013000629 W IN2013000629 W IN 2013000629W WO 2015056270 A1 WO2015056270 A1 WO 2015056270A1
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WO
WIPO (PCT)
Prior art keywords
acid
formula
hydrogen peroxide
sodium
potassium
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PCT/IN2013/000629
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English (en)
Inventor
Srinivasa Krishna Murthy Konduri
Sandeep Kumar THOOTA
Pulla Reddy Muddasani
Kali Satya Bhujanga Rao Adibhatla
Venkaiah Chowdary Nannapaneni
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Natco Pharma Limited
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Priority to PCT/IN2013/000629 priority Critical patent/WO2015056270A1/fr
Publication of WO2015056270A1 publication Critical patent/WO2015056270A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Definitions

  • the present invention relates to a novel process for the preparation of FDCA of formula- (1 ) whose chemical name is 2,5-furandicarboxylic acid (also known as dehydromucic acid or pyromucic acid).
  • 2,5-Furandicarboxylic acid is found to be one of the top 12 bio- based products identified by the US Department of energy for green chemistry industry.
  • FDCA 2,5-Furandicarboxylic acid
  • 2,5-Furandicarboxylic acid is a replacement for terephthalic acid made on large scale from petroleum-based para-xylene for the manufacture of various polyesters, such as polyethylene terephthalate (PET) and polybutylene terethalate(PBT).
  • PET polyethylene terephthalate
  • PBT polybutylene terethalate
  • 2,5-furandicarboxylic acid (FDCA) received significant attention as a desirable substitute for terephthalic acid for the manufacture of various polymeric materials like polyethylene furanoate (PEF) a furan counterpart of PET and it showed comparable functional properties and thermal stability. Therefore, there is an urgent need in the chemical industry for an efficient process to produce furan based carboxylic acids, their derivatives and compositions.
  • FDCA 2,5-Furandicarboxylic acid
  • the present invention is related to the process for making 2,5-furandicarboxylic acid (FDCA) of formula (1 ), starting from 5-Hydroxymethyl furfural (HMF) obtained from non-fossil bio-sources.
  • FDCA 2,5-furandicarboxylic acid
  • FDCA 2,5-Furandicarboxylic acid
  • HMF 5-Hydroxymethyl furfural
  • FDCA 2,5-furandicarboxylic acid
  • Catalytic oxidation processes like Ru(OH)x/hydrotalcite (HT) catalyst/1-40 bar 0 2 pressure/38h/ 140° C/water Catal. Lett., 201 1 , vol 141 , pages 1752-1760); gold nano particle catalyst-HT-1.92 wt%/ 94.8° C/water/0 2 ⁇ Green Chem., 2,1 1, vol 13, pages 824- 827); 5% Pt/C/aq. NaHC0 3 /0 2 5bar/100° C (WO201217052); 5-13% supported platinum catalyst/aq.
  • 2,5-furandicarboxylic acid is prepared by oxidation of 2,5- diformyl furan with potassium permanganate in aq. NaOH (US2007/232815) or with silver oxide ⁇ Bull. Soc. Chim. Fr., 1987, vol 5, pages 855-860); oxidation of 5-formyl- furancarboxylic acid with hydrogen peroxide in aq. sodium hydroxide ⁇ Justus Liebigs Annalen der Chem.
  • Non-scalable purification methods like chromatographic separations.
  • the main objective of the present invention is to provide an improved process for the preparation of 2,5-furandicarboxylic acid (FDCA) of formula- (1), which is simple, economical and commercially applicable.
  • Another objective of the present invention is to provide an improved process for the preparation of 2,5-furandicarboxylic acid (FDCA) of formula- (1 ), which involves readily and cheaply available raw materials.
  • FDCA 2,5-furandicarboxylic acid
  • R hydrogen, C 1 -C6 alkyl, aryl
  • 5-Acyloxymethylfurancarboxylic acid of formula (5) is prepared starting from 5-Hydroxymethylfurfural (HMF), through acylation followed by oxidation of 5-acyloxymethylfurfural of formula (4).
  • the invention provides a novel process for the preparation of 2,5- furandicarboxylic acid (FDCA) of formula (1 )
  • R hydrogen, C 1 -C6 alkyl, aryl
  • R hydrogen, C1 -C6 alkyl, aryl
  • 5-hydroxymethyl furfural (HMF) of formula (3) is reacted with an acylating agent like acetic acid, acetyl chloride or acetic anhydride or acetic-formic anhydride or formic acid or formyl chloride or propionic acid or propionyl chloride or propionic anhydride or butyric acid or butyryl chloride or butyric anhydride or benzoic acid or benzoyl chloride or Boc anhydride or benzyloxy carbonyl chloride or any acylating agent preferably acetic anhydride to get 5-acyloxymethylfurfural of formula(4).
  • an acylating agent like acetic acid, acetyl chloride or acetic anhydride or acetic-formic anhydride or formic acid or formyl chloride or propionic acid or propionyl chloride or propionic anhydride or butyric acid or butyryl chloride or butyric anhydride or benzoic acid or benzoyl chlor
  • the reaction may be done without organic solvent or with a solvent selected from ethyl acetate, toluene, diisopropyl ether, chloroform, dichloromethane, tetrahydrofuran, dioxane, dimethylformamide and dimethyl acetamide.
  • the catalytic base used in the reaction is selected from inorganic base (sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate) or from organic base (trimethyl amine, triethyl amine, ⁇ , ⁇ -dimethylaminopyridine, N-methylmorpholine, ⁇ , ⁇ -diisopropylethyl amine) preferably N,N-dimethylaminopyridine (DMAP).
  • DMAP N,N-dimethylaminopyridine
  • the reaction can be done at 0-100° C preferably at 5-50° C and most preferably at 20-25° C.
  • organic solvent selected from ester solvent like ethyl acetate, ether solvent like diisopropyl ether, aromatic hydrocarbon solvent like toluene, chlorinated solvents like chloroform, dichloromethane preferably ethyl acetate or toluene and most preferably ethyl acetate.
  • the product solution is washed with aq. base preferably selected from aq. NaHC0 3 or aq. NaOH or aq. Na 2 C0 3 or aq.
  • the 5-acyloxymethylfurfural of formula (4) is oxidized to get 5- acyloxymethylfurancarboxylic acid of the formula (5).
  • the oxidizing agent is selected from nitric acid, bromine water, sodium hypochlorite, sodium chlorite, sodium bromite, potassium chlorite, potassium bromite, hydrogen peroxide, potassium permanganate or a combination of sodium chlorite-hydrogen peroxide or potassium chlorite-hydrogen peroxide preferably sodium chlorite-hydrogen peroxide combination.
  • the percentage of hydrogen peroxide used in the reaction is selected from 6-60% preferably 35-50% and most preferably 50%.
  • the reaction solvent is selected from acetonitrile, tetrahydrofuran, ethyl acetate, chloroform preferably acetonitrile or ethyl acetate and most preferably ethyl acetate.
  • the reaction can be carried out at 0-100° C preferably at 5-50° C and most preferably at 15-20° C.
  • 5 -acyloxymethylfurancarboxylic acid of formula (5) is extracted with organic solvent selected from an ester solvent like ethyl acetate, ether solvent like diisopropyl ether, aromatic hydrocarbon solvent like toluene, chlorinated solvents like chloroform, dichloromethane preferably ethyl acetate or toluene.
  • organic solvent selected from an ester solvent like ethyl acetate, ether solvent like diisopropyl ether, aromatic hydrocarbon solvent like toluene, chlorinated solvents like chloroform, dichloromethane preferably ethyl acetate or toluene.
  • 5-acyloxymethylfurancarboxylic acid of formula (5) is oxidized to 2,5- furandicarboxylic acid (FDCA) of formula (1 ).
  • the oxidizing agent is selected from nitric acid, dilute bromine water, sodium hypochlorite, sodium chlorite, sodium bromite, potassium chlorite, potassium bromite, hydrogen peroxide, potassium permanganate, sodium permanganate or a combination of sodium chlorite-hydfogen peroxide or potassium chlorite-hydrogen peroxide or sodium bromite-hydrogen peroxide or potassium bromite-hydrogen peroxide preferably nitric acid or hydrogen peroxide.
  • the percentage of nitric acid used in the reaction is selected from 10-70% preferably 25-65% and most preferably 55%.
  • the reaction is conducted with or without water as solvent.
  • the reaction can be carried out at 0-100° C preferably at 25-95° C and most preferably at 55-60° C.
  • 2,5-furandicarboxylic acid (FDCA) of formula (1) is filtered by suction as off- white solid having more than 98% HPLC purity.
  • the product may be further purified by simple acid-base treatment.
  • This process exemplifies a novel process of making 2,5-furandicarboxylic acid of formula- 1.
  • reaction sequence can be condensed to a one-pot procedure.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Furan Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

La présente invention concerne un procédé de préparation d'acide 2,5 furane dicarboxylique de formule (I) à partir de 5-hydroxyméthylfurfural. (FDCA) (1)
PCT/IN2013/000629 2013-10-17 2013-10-17 Procédé de préparation d'acide 2,5 furane dicarboxylique WO2015056270A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/IN2013/000629 WO2015056270A1 (fr) 2013-10-17 2013-10-17 Procédé de préparation d'acide 2,5 furane dicarboxylique

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IN2013/000629 WO2015056270A1 (fr) 2013-10-17 2013-10-17 Procédé de préparation d'acide 2,5 furane dicarboxylique

Publications (1)

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WO2015056270A1 true WO2015056270A1 (fr) 2015-04-23

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Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9321744B1 (en) * 2015-06-26 2016-04-26 Industrial Technology Research Institute Method for preparing 2,5-furan dicarboxylic acid
WO2017049211A1 (fr) * 2015-09-17 2017-03-23 Micromidas, Inc. Chimie d'oxydation sur furannes aldéhydes
WO2017076956A1 (fr) 2015-11-04 2017-05-11 Basf Se Procédé pour la préparation d'acide furan-2,5-dicarboxylique
CN108130554A (zh) * 2017-10-31 2018-06-08 天津工业大学 一种次氯酸钠电催化5-hmf制备fdca的方法
US10208006B2 (en) 2016-01-13 2019-02-19 Stora Enso Oyj Processes for the preparation of 2,5-furandicarboxylic acid and intermediates and derivatives thereof
WO2019072920A1 (fr) * 2017-10-12 2019-04-18 Synphabase Ag Procédé de préparation d'acide 2,5-furanedicarboxylique
CN109970691A (zh) * 2019-04-18 2019-07-05 南京工业大学 一种利用微通道反应装置连续制备2,5-呋喃二甲酸的方法
US20200263053A1 (en) * 2017-09-19 2020-08-20 Swimc Llc Coating compositions including a furan-containing polyester, articles, and methods of coating
CN111606875A (zh) * 2020-06-15 2020-09-01 莆田达凯新材料有限公司 一种竹生物质制备呋喃二甲酸单体的方法
CN112830916A (zh) * 2020-07-02 2021-05-25 中国科学院宁波材料技术与工程研究所 一种温和条件下2,5-呋喃二甲酸的制备方法
CN112898251A (zh) * 2019-11-19 2021-06-04 中国科学院宁波材料技术与工程研究所 一种制备2,5-呋喃二甲酸的方法
US11192872B2 (en) 2017-07-12 2021-12-07 Stora Enso Oyj Purified 2,5-furandicarboxylic acid pathway products
CN114621166A (zh) * 2020-12-10 2022-06-14 中国科学院大连化学物理研究所 一种2,5-呋喃二甲酸的制备方法
CN114634472A (zh) * 2022-04-07 2022-06-17 广西科技大学 一种氧化5-羟甲基糠醛合成2,5-呋喃二甲酸的方法
CN114981250A (zh) * 2019-12-20 2022-08-30 诺瓦蒙特股份公司 2,5-呋喃二甲酸的合成方法
CN115991686A (zh) * 2023-03-21 2023-04-21 吉林省中科聚合工程塑料有限公司 一种制备2，5-呋喃二甲酸的方法
WO2023226181A1 (fr) * 2022-05-27 2023-11-30 上海沃凯生物技术有限公司 Procédé de préparation d'acide 2,5-furandicarboxylique à l'aide de furfural
US11873286B2 (en) 2022-05-27 2024-01-16 Shanghai Wokai Biotechnology Co., Ltd. Method for preparing 2,5-furandicarboxylic acid (FDCA) from furfural

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US20120302771A1 (en) * 2011-05-24 2012-11-29 Eastman Chemical Company Oxidation process to produce a crude and/or purified carboxylic acid product
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WO2013033081A2 (fr) 2011-08-31 2013-03-07 The University Of Kansas Procédé pour la production à la fois d'acide succinique et d'acide 2,5-furandicarboxylique biosourcés

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Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9321744B1 (en) * 2015-06-26 2016-04-26 Industrial Technology Research Institute Method for preparing 2,5-furan dicarboxylic acid
WO2017049211A1 (fr) * 2015-09-17 2017-03-23 Micromidas, Inc. Chimie d'oxydation sur furannes aldéhydes
CN108349920A (zh) * 2015-09-17 2018-07-31 微麦德斯公司 呋喃醛上的氧化化学
US10392358B2 (en) * 2015-09-17 2019-08-27 Micromidas, Inc. Oxidation chemistry on furan aldehydes
WO2017076956A1 (fr) 2015-11-04 2017-05-11 Basf Se Procédé pour la préparation d'acide furan-2,5-dicarboxylique
US10428039B2 (en) 2015-11-04 2019-10-01 Basf Se Process for preparing furan-2,5-dicarboxylic acid
CN108473456A (zh) * 2015-11-04 2018-08-31 巴斯夫欧洲公司 制备呋喃-2,5-二甲酸的方法
US10208006B2 (en) 2016-01-13 2019-02-19 Stora Enso Oyj Processes for the preparation of 2,5-furandicarboxylic acid and intermediates and derivatives thereof
US11613523B2 (en) 2016-01-13 2023-03-28 Stora Enso Oyj Processes for the preparation of 2,5-furandicarboxylic acid and intermediates and derivatives thereof
US11891370B2 (en) 2016-01-13 2024-02-06 Stora Enso Ojy Processes for the preparation of 2,5-furandicarboxylic acid and intermediates and derivatives thereof
US10442780B2 (en) 2016-01-13 2019-10-15 Stora Enso Oyj Processes for the preparation of 2,5-furandicarboxylic acid and intermediates and derivatives thereof
US10654819B2 (en) 2016-01-13 2020-05-19 Stora Enso Oyj Processes for the preparation of 2,5-furandicarboxylic acid and intermediates and derivatives thereof
US10851074B2 (en) 2016-01-13 2020-12-01 Stora Enso Oyj Processes for the preparation of 2,5-furandicarboxylic acid and intermediates and derivatives thereof
US11192872B2 (en) 2017-07-12 2021-12-07 Stora Enso Oyj Purified 2,5-furandicarboxylic acid pathway products
US20200263053A1 (en) * 2017-09-19 2020-08-20 Swimc Llc Coating compositions including a furan-containing polyester, articles, and methods of coating
WO2019072920A1 (fr) * 2017-10-12 2019-04-18 Synphabase Ag Procédé de préparation d'acide 2,5-furanedicarboxylique
CN111194311A (zh) * 2017-10-12 2020-05-22 辛法贝斯股份公司 用于制备呋喃-2,5-二甲酸的方法
DE102017123797A1 (de) * 2017-10-12 2019-04-18 Synphabase Ag Furandicarbonsäure
CN108130554A (zh) * 2017-10-31 2018-06-08 天津工业大学 一种次氯酸钠电催化5-hmf制备fdca的方法
CN109970691B (zh) * 2019-04-18 2020-08-07 南京工业大学 一种利用微通道反应装置连续制备2,5-呋喃二甲酸的方法
CN109970691A (zh) * 2019-04-18 2019-07-05 南京工业大学 一种利用微通道反应装置连续制备2,5-呋喃二甲酸的方法
CN112898251A (zh) * 2019-11-19 2021-06-04 中国科学院宁波材料技术与工程研究所 一种制备2,5-呋喃二甲酸的方法
CN114981250A (zh) * 2019-12-20 2022-08-30 诺瓦蒙特股份公司 2,5-呋喃二甲酸的合成方法
CN111606875B (zh) * 2020-06-15 2022-12-30 莆田达凯新材料有限公司 一种竹生物质制备呋喃二甲酸单体的方法
CN111606875A (zh) * 2020-06-15 2020-09-01 莆田达凯新材料有限公司 一种竹生物质制备呋喃二甲酸单体的方法
CN112830916A (zh) * 2020-07-02 2021-05-25 中国科学院宁波材料技术与工程研究所 一种温和条件下2,5-呋喃二甲酸的制备方法
CN114621166A (zh) * 2020-12-10 2022-06-14 中国科学院大连化学物理研究所 一种2,5-呋喃二甲酸的制备方法
CN114634472A (zh) * 2022-04-07 2022-06-17 广西科技大学 一种氧化5-羟甲基糠醛合成2,5-呋喃二甲酸的方法
WO2023226181A1 (fr) * 2022-05-27 2023-11-30 上海沃凯生物技术有限公司 Procédé de préparation d'acide 2,5-furandicarboxylique à l'aide de furfural
US11873286B2 (en) 2022-05-27 2024-01-16 Shanghai Wokai Biotechnology Co., Ltd. Method for preparing 2,5-furandicarboxylic acid (FDCA) from furfural
CN115991686A (zh) * 2023-03-21 2023-04-21 吉林省中科聚合工程塑料有限公司 一种制备2，5-呋喃二甲酸的方法

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