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WO2015155784A1 - Procédé pour la préparation d'acide 2,5-furanedicarboxylique et de son dérivé ester - Google Patents

Procédé pour la préparation d'acide 2,5-furanedicarboxylique et de son dérivé ester Download PDF

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Publication number
WO2015155784A1
WO2015155784A1 PCT/IN2014/000479 IN2014000479W WO2015155784A1 WO 2015155784 A1 WO2015155784 A1 WO 2015155784A1 IN 2014000479 W IN2014000479 W IN 2014000479W WO 2015155784 A1 WO2015155784 A1 WO 2015155784A1
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WO
WIPO (PCT)
Prior art keywords
formula
acid
furandicarboxylic acid
preparation
furandicarboxylic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/IN2014/000479
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English (en)
Inventor
Srinivasa Krishna Murthy Konduri
Sandeep Kumar THOOTA
Chandrasekhar JAVVADI
Pulla Reddy Muddasani
Kali Satya Bhujanga Rao Adibhatla
Venkaiah Chowdary Nannapaneni
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Natco Pharma Ltd
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Natco Pharma Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Natco Pharma Ltd filed Critical Natco Pharma Ltd
Publication of WO2015155784A1 publication Critical patent/WO2015155784A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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 an improved process for the preparation of 2,5-furan dicarboxylic acid (FDCA) of formula (1) and its ester derivative chemically denoted as dimethyl 2,5-furandicarboxylate of formula-(2).
  • FDCA 2,5-furan dicarboxylic acid
  • PEF poly(ethylene furanoate)
  • Aromatic dicarboxylic acids like terephthalic acid are used to produce a variety of polyester derivatives such as poly(ethylene terephthalate) also known as PET. These aromatic dicarboxylic acids are prepared by the catalytic oxidation of the corresponding dialkyl derivatives which are obtained from fossil fuels.
  • 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 and its corresponding ester derivative of formula (2).
  • FDCA 2,5-furandicarboxylic acid
  • FDCA 2,5-Furandicarboxylic acid
  • 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, safe, 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
  • HMF 5- hydroxymethylfurfural
  • the basic raw material selected for the synthesis of 2,5-furandicarboxylic acid (FDCA) of formula (1 ) is 5-hydroxymethyl furfural (HMF) of formula (4).
  • the process is as outlined in scheme (3).
  • the invention provides a novel process for the preparation furandicarboxylic acid (FDCA) of formula (1) and its methyl ester of formula (2)
  • 5-hydroxymethyl furfural (HMF) of formula (4) is oxidized with an oxidizing agent selected oxygen or air preferably air to get 2,5-furandicarboxylic acid of formula (1) using catalysts like oxides of lanthanum, zirconium, tantalum, niobium, molybdenum, manganese, iron, cobalt, iridium, nickel and copper or their mixtures.
  • the reaction may be done in acetic acid or in water.
  • the reaction may be done at 10-40 bar oxygen or air pressure.
  • the reaction may be done at 25-150° C preferably at 100- 130° C.
  • the excess solvent is removed by distillation. Trituration of the resulting solid in aq.
  • 2,5-furandicarboxylic acid is esterified using methanol and catalysts like thionyl chloride, sulfuric acid or hydrochloric acid.
  • the temperature of the reaction for methylation is 25-65° C, preferably at 60-65° C.
  • the reaction solution is cooled to 5-25° C and most preferably 20-25° C to get crystalline white solid having HPLC purity of more than 99.5%.
  • the product is further purified by crystallization from methanol to get crystalline white solid having more than 99.9% HPLC purity.
  • Oxidation reaction can be done at low pressure when compared to reported data.
  • This process exemplifies a process of making 2,5-furandicarboxylic acid of formula- 1 employing commercially available metal oxides.
  • the procedure can be easily scaled up to multi-kilogram level.
  • the catalysts used in the reaction can be easily recovered and regenerated for recycling without loss in activity.
  • the present process successfully reduces the formation of impurities.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Furan Compounds (AREA)

Abstract

La présente invention concerne un nouveau procédé de préparation d'acide 2,5 furanedicarboxylique de formule (I) et de son dérivé ester, chimiquement désigné en tant que diméthyl-2,5-furanedicarboxylate de formule (2). L'acide 2,5 furanedicarboxylique s'avère être un intermédiaire clé pour préparer du poly(éthylènefuranoate), également connu sous le nom de PEF.
PCT/IN2014/000479 2014-04-09 2014-07-21 Procédé pour la préparation d'acide 2,5-furanedicarboxylique et de son dérivé ester Ceased WO2015155784A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1874CH2014 2014-04-09
IN1874/CHE/2014 2014-04-09

Publications (1)

Publication Number Publication Date
WO2015155784A1 true WO2015155784A1 (fr) 2015-10-15

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2014/000479 Ceased WO2015155784A1 (fr) 2014-04-09 2014-07-21 Procédé pour la préparation d'acide 2,5-furanedicarboxylique et de son dérivé ester

Country Status (1)

Country Link
WO (1) WO2015155784A1 (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI641483B (zh) * 2017-11-08 2018-11-21 財團法人工業技術研究院 可撓導電結構與可撓電子裝置
KR20190003398A (ko) * 2017-06-30 2019-01-09 한국생산기술연구원 하이드록시메틸푸르푸랄로부터 2,5-퓨란디메틸카르복실레이트의 제조방법
CN109705069A (zh) * 2019-01-23 2019-05-03 厦门大学 一种2,5-呋喃二甲酸的制备方法
CN110590721A (zh) * 2019-09-29 2019-12-20 厦门大学 一种由5-羟甲基糠醛制备2,5-呋喃二甲酸二酯类化合物的方法
CN110586114A (zh) * 2019-09-19 2019-12-20 天津大学 一种铜铬铝水滑石催化剂的制备方法及催化氧化5-羟甲基糠醛的应用
WO2022230769A1 (fr) 2021-04-30 2022-11-03 三菱ケミカル株式会社 Procédé de fabrication de dérivé de furane contenant un ５－hydroxyméthylfurfural （５－ｈｍｆ）, dérivé de furane, solution contenant ce dérivé de furane, et procédé de fabrication d'acide furanedicarboxylique ou d'ester d'acide furanedicarboxylique
CN116217528A (zh) * 2023-03-08 2023-06-06 中科国生(杭州)科技有限公司 一种2,5呋喃二甲酸二甲酯的制备方法
CN116348457A (zh) * 2020-08-12 2023-06-27 阿彻丹尼尔斯米德兰德公司 2,5-呋喃二甲酸二甲酯和其他酯化产物的纯化
CN117229241A (zh) * 2023-08-14 2023-12-15 中科国生(杭州)科技有限公司 一种2,5-呋喃二甲酸的纯化方法
CN117362252A (zh) * 2023-10-08 2024-01-09 华东师范大学 一种从呋喃制备2,5-呋喃二甲酸二甲酯的方法
CN117683007A (zh) * 2023-11-02 2024-03-12 中科国生(杭州)科技有限公司 一种Amberlyst系列催化剂制备2,5-呋喃二甲酸二甲酯的方法

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WO2011043660A2 (fr) * 2009-10-07 2011-04-14 Furanix Technologies B.V. Procédé de préparation d'acide 2,5-furandicarboxylique et de ses esters
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WO2013191942A1 (fr) * 2012-06-22 2013-12-27 Eastman Chemical Company Procédé de production de dialkyl-furan-2,5-dicarboxylate purifié par séparation physique et par séparation solide/liquide

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JP2009023916A (ja) * 2007-07-17 2009-02-05 Canon Inc ２，５−フランジカルボン酸の製造方法
JP2009242312A (ja) * 2008-03-31 2009-10-22 Air Water Inc ２，５−フランジカルボン酸の製造方法
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WO2011043660A2 (fr) * 2009-10-07 2011-04-14 Furanix Technologies B.V. Procédé de préparation d'acide 2,5-furandicarboxylique et de ses esters
WO2011043661A1 (fr) 2009-10-07 2011-04-14 Furanix Technologies B.V. Procédé de préparation d'acide 2,5-furane dicarboxylique et de préparation de l'ester dialkylique d'acide 2,5-furane dicarboxylique
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WO2012017052A1 (fr) 2010-08-06 2012-02-09 Novamont S.P.A. Procédé de synthèse d'acide 2,5-furandicarboxylique
US20120302770A1 (en) 2011-05-24 2012-11-29 Eastman Chemical Company oxidation process to produce a crude and/or purified carboxylic acid product
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
WO2013191942A1 (fr) * 2012-06-22 2013-12-27 Eastman Chemical Company Procédé de production de dialkyl-furan-2,5-dicarboxylate purifié par séparation physique et par séparation solide/liquide

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20190003398A (ko) * 2017-06-30 2019-01-09 한국생산기술연구원 하이드록시메틸푸르푸랄로부터 2,5-퓨란디메틸카르복실레이트의 제조방법
KR102016647B1 (ko) 2017-06-30 2019-08-30 한국생산기술연구원 하이드록시메틸푸르푸랄로부터 2,5-퓨란디메틸카르복실레이트의 제조방법
TWI641483B (zh) * 2017-11-08 2018-11-21 財團法人工業技術研究院 可撓導電結構與可撓電子裝置
CN109705069A (zh) * 2019-01-23 2019-05-03 厦门大学 一种2,5-呋喃二甲酸的制备方法
CN110586114A (zh) * 2019-09-19 2019-12-20 天津大学 一种铜铬铝水滑石催化剂的制备方法及催化氧化5-羟甲基糠醛的应用
CN110590721B (zh) * 2019-09-29 2021-08-31 厦门大学 一种由5-羟甲基糠醛制备2,5-呋喃二甲酸二酯类化合物的方法
CN110590721A (zh) * 2019-09-29 2019-12-20 厦门大学 一种由5-羟甲基糠醛制备2,5-呋喃二甲酸二酯类化合物的方法
CN116348457A (zh) * 2020-08-12 2023-06-27 阿彻丹尼尔斯米德兰德公司 2,5-呋喃二甲酸二甲酯和其他酯化产物的纯化
WO2022230769A1 (fr) 2021-04-30 2022-11-03 三菱ケミカル株式会社 Procédé de fabrication de dérivé de furane contenant un ５－hydroxyméthylfurfural （５－ｈｍｆ）, dérivé de furane, solution contenant ce dérivé de furane, et procédé de fabrication d'acide furanedicarboxylique ou d'ester d'acide furanedicarboxylique
CN116217528A (zh) * 2023-03-08 2023-06-06 中科国生(杭州)科技有限公司 一种2,5呋喃二甲酸二甲酯的制备方法
CN117229241A (zh) * 2023-08-14 2023-12-15 中科国生(杭州)科技有限公司 一种2,5-呋喃二甲酸的纯化方法
CN117362252A (zh) * 2023-10-08 2024-01-09 华东师范大学 一种从呋喃制备2,5-呋喃二甲酸二甲酯的方法
CN117683007A (zh) * 2023-11-02 2024-03-12 中科国生(杭州)科技有限公司 一种Amberlyst系列催化剂制备2,5-呋喃二甲酸二甲酯的方法

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