FI126387B - Menetelmä furaanikarboksylaattien valmistamiseksi aldaarihapoista käyttämällä kiinteää heterogeenista katalyyttiä - Google Patents

Menetelmä furaanikarboksylaattien valmistamiseksi aldaarihapoista käyttämällä kiinteää heterogeenista katalyyttiä Download PDF

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FI126387B
FI126387B FI20155285A FI20155285A FI126387B FI 126387 B FI126387 B FI 126387B FI 20155285 A FI20155285 A FI 20155285A FI 20155285 A FI20155285 A FI 20155285A FI 126387 B FI126387 B FI 126387B
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acid
solvent
furan
process according
catalyst
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FI20155285A
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Swedish (sv)
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FI20155285A (fi
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Martta Asikainen
David Thomas
Ali Harlin
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Teknologian Tutkimuskeskus Vtt Oy
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Priority to FI20155285A priority Critical patent/FI126387B/fi
Priority to EP16779667.1A priority patent/EP3283471B1/en
Priority to PCT/FI2016/050254 priority patent/WO2016166421A1/en
Priority to US15/566,759 priority patent/US10301276B2/en
Publication of FI20155285A publication Critical patent/FI20155285A/fi
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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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
    • B01J21/04—Alumina
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • B01J21/066—Zirconium or hafnium; Oxides or hydroxides thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • B01J21/08—Silica
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/03—Catalysts comprising molecular sieves not having base-exchange properties
    • B01J29/0308—Mesoporous materials not having base exchange properties, e.g. Si-MCM-41
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0215—Sulfur-containing compounds
    • B01J31/0225—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0201—Impregnation
    • B01J37/0203—Impregnation the impregnation liquid containing organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/02—Monosaccharides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/181—Acids containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/66—Polyesters containing oxygen in the form of ether groups
    • C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/672—Dicarboxylic acids and dihydroxy compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
    • B01J2229/30—After treatment, characterised by the means used
    • B01J2229/32—Reaction with silicon compounds, e.g. TEOS, siliconfluoride

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Dispersion Chemistry (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Biotechnology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Furan Compounds (AREA)

Claims (10)

1. Menetelmä furaanikarboksylaattien ja furaanidikarboksylaattien valmistamiseksi aldaa-rihapoista, tunnettu siitä, että aldaarihappo, kiinteä heterogeeninen katalyytti, joka on valittu ryhmästä, jonka muodostavat perfluorisulfonihappopolymeeri, fenyylisulfonihappoetyylisulfidipiidi oksidi, sulfonoitu alumiinioksidikatalyytti ja sulfonoitu zirkoniumoksidikatalyytti, ja liuotin sekoitetaan yhteen 200-250 °C:n lämpötilassa ja käytetään 0,25-4 tunnin reaktioaikaa, jolloin muodostuu liuos, joka käsittää fu-raaniestereitä.
2. Patenttivaatimuksen 1 mukainen menetelmä, tunnettu siitä, että menetelmä käsittää seuraavat vaiheet: - panostetaan aldaarihappo, ei-toksinen heterogeeninen kiinteä happokatalyytti ja orgaaninen liuotin painereaktioastiaan, jolloin muodostuu reaktioseos - kuumennetaan reaktioseos 200-250 °C:n lämpötilaan mainitussa reaktioastiassa - pidetään lämpötila reaktioastiassa etukäteen määrätty reaktioaika ja - otetaan talteen haluttu furaaniesteri(t) j a/tai happo (hapot) reaktioseoksesta.
3. Patenttivaatimuksen 1 tai 2 mukainen menetelmä, tunnettu siitä, että käytetään reaktioaikaa, joka on 0,5-2 tuntia, sopivimmin noin 1 tunti.
4. Jonkin edellä olevan patenttivaatimuksen mukainen menetelmä, tunnettu siitä, että aldaarihappo on joko galaktaarihappo tai glukaarihappo joko vapaan hapon tai esterin muodossa.
5. Jonkin edellä olevan patenttivaatimuksen mukainen menetelmä, tunnettu siitä, että liuotin on vesi tai tetrahydroiuraani (THF) tai niiden seokset.
6. Jonkin edellä olevan patenttivaatimuksen mukainen menetelmä, tunnettu siitä, että liuotin on alkoholiliuotin, joka on valittu ryhmästä, jonka muodostavat yksiarvoiset ja moniarvoiset Ci-6-alkoholit, tai niiden mikä tahansa yhdistelmä.
7. Jonkin edellä olevan patenttivaatimuksen mukainen menetelmä, tunnettu siitä, että liuotin on valittu ryhmästä, jonka muodostavat etanoli, 1-butanoli ja 1-pentanoli, tai niiden mikä tahansa yhdistelmä.
8. Jonkin edellä olevan patenttivaatimuksen mukainen menetelmä, tunnettu siitä, että menetelmässä muodostuu 2,5-furaanidikarboksyylihapon (FDCA) esteriä.
9. Jonkin edellä olevan patenttivaatimuksen mukainen menetelmä, jolloin liuottimen höy-rynpaine on 5-50 baaria, edullisesti 15-30 baaria.
10. Jonkin edellä olevan patenttivaatimuksen mukainen menetelmä, tunnettu siitä, että katalyytti ja/tai liuotin otetaan talteen reaktioliuoksesta.
FI20155285A 2015-04-17 2015-04-17 Menetelmä furaanikarboksylaattien valmistamiseksi aldaarihapoista käyttämällä kiinteää heterogeenista katalyyttiä FI126387B (fi)

Priority Applications (4)

Application Number Priority Date Filing Date Title
FI20155285A FI126387B (fi) 2015-04-17 2015-04-17 Menetelmä furaanikarboksylaattien valmistamiseksi aldaarihapoista käyttämällä kiinteää heterogeenista katalyyttiä
EP16779667.1A EP3283471B1 (en) 2015-04-17 2016-04-18 Method of producing furan carboxylates from aldaric acids by using solid heterogeneous catalysts
PCT/FI2016/050254 WO2016166421A1 (en) 2015-04-17 2016-04-18 Method of producing furan carboxylates from aldaric acids by using solid heterogeneous catalysts
US15/566,759 US10301276B2 (en) 2015-04-17 2016-04-18 Method of producing furan carboxylates from aldaric acids by using solid heterogeneous catalyst

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FI20155285A FI126387B (fi) 2015-04-17 2015-04-17 Menetelmä furaanikarboksylaattien valmistamiseksi aldaarihapoista käyttämällä kiinteää heterogeenista katalyyttiä

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FI20155285A FI20155285A (fi) 2016-10-18
FI126387B true FI126387B (fi) 2016-11-15

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US (1) US10301276B2 (fi)
EP (1) EP3283471B1 (fi)
FI (1) FI126387B (fi)
WO (1) WO2016166421A1 (fi)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019155127A1 (en) 2018-02-09 2019-08-15 Teknologian Tutkimuskeskus Vtt Oy Separation and purification of furan carboxylates

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Publication number Priority date Publication date Assignee Title
WO2017083297A1 (en) * 2015-11-11 2017-05-18 Bp Corporation North America Inc. Acids-catalyzed dehydration of glucaric acid to 2,5-furandicarboxylic acid (fdca)
EP3402787A4 (en) 2016-01-13 2019-11-27 Stora Enso Oyj PROCESSES FOR PREPARING 2,5-FURANDICARBOXYLIC ACID AND INTERMEDIATES AND DERIVATIVES THEREOF
JP6970909B2 (ja) * 2017-05-26 2021-11-24 大日本印刷株式会社 多層容器およびその製造方法
EP4071142B1 (en) * 2017-06-22 2023-10-04 Archer Daniels Midland Company Process for making esters of 2,5-furandicarboxylic acid
SG11201913469PA (en) 2017-07-12 2020-01-30 Stora Enso Oyj Purified 2,5-furandicarboxylic acid pathway products
FI127644B (fi) * 2017-09-01 2018-11-15 Teknologian Tutkimuskeskus Vtt Oy Furaanihapon synteesi ksylonihaposta
KR102041210B1 (ko) * 2018-03-22 2019-11-27 한국생산기술연구원 갈락타릭산을 이용한 퓨란 디알킬카르복실레이트의 제조방법
CN109365004B (zh) * 2018-11-28 2022-03-18 武汉工程大学 一种磁性固体酸催化剂及其提取皂素的应用
FI128987B (fi) 2018-12-10 2021-04-30 Teknologian Tutkimuskeskus Vtt Oy Furaanidikarboksyylihapon ja sen esterin synteesi
KR102278268B1 (ko) * 2019-11-22 2021-07-16 한국화학연구원 5-알콕시메틸퍼퓨랄로부터 2,5-퓨란디카르복실산 제조방법
JP2023527820A (ja) * 2020-05-29 2023-06-30 ブラスケン・エス．エー． フランジカルボキシル酸ジエステルの２，４－異性体に基づく可塑剤の生産及び使用
FI130511B (fi) 2021-01-15 2023-10-18 Teknologian Tutkimuskeskus Vtt Oy Furaanidikarboksyylihapon synteesi aldaarihaposta
CN116768832A (zh) * 2022-03-10 2023-09-19 江苏赛瑞克新材料科技有限公司 2,5-呋喃二甲酸类化合物的制备方法

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FR2723946B1 (fr) 1994-08-24 1996-10-18 Ard Sa Procede de fabrication d'un diester de l'acide 2,5-furane dicarboxylique
FR2723945B1 (fr) 1994-08-24 1996-10-18 Ard Sa Procede de fabrication de l'acide 2,5-furane dicarboxylique
JP5051509B2 (ja) 2006-11-16 2012-10-17 独立行政法人産業技術総合研究所 ２，５−フランジカルボン酸ジエステルの製造方法
WO2011063500A1 (en) 2009-11-24 2011-06-03 National Research Council Of Canada Process for preparing furfural from xylose
WO2013049711A1 (en) 2011-09-29 2013-04-04 Bio Architecture Lab, Inc. Methods for preparing 2,5-furandicarboxylic acid
JP2014019827A (ja) 2012-07-20 2014-02-03 Hitachi Ltd ポリエステル製造方法及び装置

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019155127A1 (en) 2018-02-09 2019-08-15 Teknologian Tutkimuskeskus Vtt Oy Separation and purification of furan carboxylates
US11446586B2 (en) 2018-02-09 2022-09-20 Teknologian Tutkimuskeskus Vtt Oy Separation and purification of furan carboxylates

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Publication number Publication date
EP3283471A4 (en) 2018-10-10
EP3283471B1 (en) 2021-06-09
WO2016166421A1 (en) 2016-10-20
EP3283471A1 (en) 2018-02-21
US10301276B2 (en) 2019-05-28
FI20155285A (fi) 2016-10-18
US20180086728A1 (en) 2018-03-29

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