SI3157910T1 - Postopek selektivne oksidacije 5-hidroksimetilfurfurala - Google Patents

Postopek selektivne oksidacije 5-hidroksimetilfurfurala Download PDF

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Publication number
SI3157910T1
SI3157910T1 SI201530287T SI201530287T SI3157910T1 SI 3157910 T1 SI3157910 T1 SI 3157910T1 SI 201530287 T SI201530287 T SI 201530287T SI 201530287 T SI201530287 T SI 201530287T SI 3157910 T1 SI3157910 T1 SI 3157910T1
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Slovenia
Prior art keywords
process according
carboxylic acid
catalyst
solvent
bar
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SI201530287T
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English (en)
Inventor
Marko Mihovilovic
Michael Schon
Stefan Dochev
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Annikki Gmbh
Microinnova Engineering Gmbh
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Application filed by Annikki Gmbh, Microinnova Engineering Gmbh filed Critical Annikki Gmbh
Publication of SI3157910T1 publication Critical patent/SI3157910T1/sl

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34Heterocyclic 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
    • C07D307/38Heterocyclic 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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40Radicals substituted by oxygen atoms
    • C07D307/42Singly bound oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34Heterocyclic 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
    • C07D307/38Heterocyclic 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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40Radicals substituted by oxygen atoms
    • C07D307/46Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34Heterocyclic 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
    • C07D307/38Heterocyclic 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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40Radicals substituted by oxygen atoms
    • C07D307/46Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C07D307/48Furfural

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)
  • Catalysts (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Claims (16)

  1. POSTOPEK SELEKTIVNE OKSIDACIJE 5-HIDROKSIMETILFURFURALA Patentni zahtevki
    1. Postopek za selektivno izdelavo oksidiranih derivatov furana, izhajajoč iz 5-hidroksimetil-2-furfurala s formulo
    v prisotnosti topila, oksidacijskega sredstva, katalizatorja in izbiroma baze in/ali sotopila, značilen po tem, da se oksidacijski postopek izvaja neprekinjeno v toku, se postopek izveja v reaktorju, ki je nastavljen za različne reakcijske parametre, je topilo za oksidacijski postopek voda in je dipolarno aprotično topilo prisotno kot sotopilo.
  2. 2. Postopek po zahtevku 1, značilen po tem, da je kot sotopilo prisoten N-metilpirolidon.
  3. 3. Postopek po zahtevku 1 ali 2, pri čemer so reakcijski parametri temperatura, tlak, oksidacijsko sredstvo in/ali katalizator.
  4. 4. Postopek po enem od zahtevkov 1 do 3, pri čemer omenjeni oksidirani derivat furana obsega vsaj eno aldehidno skupino in/ali vsaj eno skupino karboksilne kisline.
  5. 5. Postopek po zahtevku 4, pri čemer je omenjeni oksidiran derivat furana izbran med 5-hidroksimetilfuran-2-karboksilno kislino s formulo
    2,5-diformilfuranom s formulo
    5-formilfuran-2-karboksilno kislino s formulo
    in 2,5-furandikarboksilno kislino s formulo
  6. 6. Postopek po katerem koli od zahtevkov 1 do 5, značilen po tem, da je reakcijska temperatura med 50 °C in 180 °C, zlasti med 60 °C in 160 °C.
  7. 7. Postopek po zahtevku 6, pri čemer reakcijska temperatura za izdelavo 5-hidroksimetilfuran-2-karboksilne kisline znaša od 60 °C do 120 °C, zlasti od 80 °C do 120 °C, zlasti od 100 °C do 120 °C; 2.5- diformilfurana od 100 °C do 160 °C, zlasti od 120 °C do 160 °C, zlasti od 140 °C do 160 °C; 5-formilfuran-2-karboksilne kisline od 60 °C do 160 °C, zlasti od 80 °C do 140 °C, zlasti od 100 °C do 120 °C; 2.5- furandikarboksilne kisline od 60 °C do 160 °C, zlasti od 60 °C do 120 °C, zlasti od 80 °C do 120 °C.
  8. 8. Postopek po katerem koli od zahtevkov 1 do 7, značilen po tem, da je oksidacijsko sredstvo stisnjen kisik ali stisnjen zrak.
  9. 9. Postopek po katerem koli od zahtevkov 1 do 8, značilen po tem, da delovni tlak leži med 5 bar in 100 bar, zlasti med 10 bar in 80 bar.
  10. 10. Postopek po katerem koli od zahtevkov 1 do 9, značilen po tem, da je katalizator, ki se ga uporabi, da se pridobi 2.5- diformilfuran K-OMS-2; 5-hidroksimetilfuran-2-karoboksilno kislino, 5-formilfuran-2-karboksilno kislino in 2.5- furandikarboksilno kislino platina na aktivnem oglju.
  11. 11. Postopek po katerem koli od zahtevkov 1 do 10, pri čemer je za izdelavo 5-hidroksimetilfuran-2-karboksilne kisline, 5-formilfuran-2-karboksilne kisline in 2,5-furandikarboksilne kisline kot sokatalizator uporabljena baza.
  12. 12. Postopek po enem od zahtevkov 1 do 11, značilen po tem, da je baza hidroksid, karbonat ali bikarbonat, zlasti alkalni hidroksid, alkalni karbonat ali alkalni bikarbonat, zlasti natrijev hidroksid, natrijev karbonat ali natrijev bikarbonat.
  13. 13. Postopek po katerem koli od predhodnih zahtevkov, značilen po tem, da je kot začetni material uporabljen tok, obogaten s 5-hidroksimetil-2-furfuralom iz prejšnjih dehidracijskih reakcij, zlasti dehidracij sladkorjev.
  14. 14. Postopek po katerem koli od predhodnih zahtevkov za selektivno izdelavo 2,5-furandikarboksilne kisline, ki se začne s 5-hidroksimetil-2-furfuralom, značilen po kombinaciji naslednjih značilnosti: kot sokatalizator je uporabljena baza, izbrana iz skupine karbonatov in bikarbonatov, zlasti natrijevega karbonata in/ali natrijevega bikarbonata delovni tlak leži med 80 in 100 bar.
  15. 15. Postopek po zahtevku 14, značilen po tem, da temperatura leži med 120 °C in 160 °C, prednostno med 140 °C in 160 °C.
  16. 16. Postopek po zahtevku 14 in 15, značilen po tem, da je kot katalizator uporabljena platina na aktivnem oglju.
SI201530287T 2014-06-17 2015-06-17 Postopek selektivne oksidacije 5-hidroksimetilfurfurala SI3157910T1 (sl)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP14172678 2014-06-17
PCT/EP2015/063578 WO2015193364A1 (en) 2014-06-17 2015-06-17 Process for the selective oxidation of 5-hydroxymethylfurfural
EP15730477.5A EP3157910B1 (en) 2014-06-17 2015-06-17 Process for the selective oxidation of 5-hydroxymethylfurfural

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SI3157910T1 true SI3157910T1 (sl) 2018-07-31

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US (1) US20170137396A1 (sl)
EP (1) EP3157910B1 (sl)
JP (1) JP6626100B2 (sl)
KR (1) KR102498728B1 (sl)
CN (1) CN106458950B (sl)
AR (1) AR100893A1 (sl)
AU (1) AU2015276185B2 (sl)
BR (1) BR112016029597B1 (sl)
CA (1) CA2949436C (sl)
DK (1) DK3157910T3 (sl)
ES (1) ES2672932T3 (sl)
HR (1) HRP20180840T1 (sl)
HU (1) HUE037981T2 (sl)
LT (1) LT3157910T (sl)
MA (1) MA40011A (sl)
MX (1) MX365828B (sl)
NO (1) NO3157910T3 (sl)
PL (1) PL3157910T3 (sl)
PT (1) PT3157910T (sl)
RS (1) RS57293B1 (sl)
RU (1) RU2703511C2 (sl)
SI (1) SI3157910T1 (sl)
TR (1) TR201807834T4 (sl)
WO (1) WO2015193364A1 (sl)

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US9944615B2 (en) 2014-05-08 2018-04-17 Eastman Chemical Company Purifying crude furan 2,5-dicarboxylic acid by hydrogenation and a purge zone
US9604202B2 (en) * 2014-05-08 2017-03-28 Eastman Chemical Company Furan-2,5-dicarboxylic acid purge process
US9943834B2 (en) 2014-05-08 2018-04-17 Eastman Chemical Company Furan-2,5-dicarboxylic acid purge process
US10010812B2 (en) 2014-05-08 2018-07-03 Eastman Chemical Company Furan-2,5-dicarboxylic acid purge process
CO2018005804A2 (es) * 2015-12-10 2018-09-20 Annikki Gmbh Proceso para producción de ácido 2,5-furandicarboxílico (fdca)
WO2017202686A1 (de) 2016-05-23 2017-11-30 Annikki Gmbh Verfahren zur enzymatischen umwandlung von d-glucose in d-fructose via d-sorbitol
CN106008416B (zh) * 2016-07-04 2019-02-19 浙江大学 一种2,5-呋喃二甲醛的制备方法
US20190023838A1 (en) 2017-07-20 2019-01-24 Eastman Chemical Company Production of polyethylene furanoate in a retrofitted pet plant
CN109912549A (zh) * 2017-12-12 2019-06-21 南京林业大学 一种5-羟甲基糠醛选择氧化制备5-羟甲基糠酸的新方法
US10344011B1 (en) 2018-05-04 2019-07-09 Eastman Chemical Company Furan-2,5-dicarboxylic acid purge process
EP3626711A1 (en) * 2018-09-24 2020-03-25 Arbaflame Technology AS Process for the production of furfural
US10526301B1 (en) 2018-10-18 2020-01-07 Eastman Chemical Company Production of purified dialkyl-furan-2,5-dicarboxylate (DAFD) in a retrofitted DMT plant
CN115536622A (zh) * 2021-06-29 2022-12-30 中国石油化工股份有限公司 合成2,5-呋喃二甲酸的方法和装置
CN113559930B (zh) * 2021-07-26 2023-05-23 南京林业大学 一种木质素磺酸钠作载体的固体催化剂的制备方法及应用
CN115028609B (zh) * 2022-07-14 2024-04-30 中科国生(杭州)科技有限公司 一种连续化生产5-羟甲基糠醛的生产工艺及装置
CN115583875B (zh) * 2022-09-28 2023-12-01 联化科技(台州)有限公司 在连续流反应器中将烯丙型醇氧化为α,β-不饱和醛酮的方法
CN116396249B (zh) * 2023-04-11 2023-11-21 中国科学院山西煤炭化学研究所 一种Co/NC-DA-x中空结构催化剂的应用及2,5-二羟甲基呋喃的制备方法

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SU448177A2 (sl) * 1972-10-30 1974-10-30
DE3826073A1 (de) * 1988-07-30 1990-02-01 Hoechst Ag Verfahren zur oxidation von 5-hydroxymethylfurfural
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HUE037981T2 (hu) 2018-09-28
DK3157910T3 (en) 2018-06-18
EP3157910A1 (en) 2017-04-26
AR100893A1 (es) 2016-11-09
CN106458950B (zh) 2019-08-27
JP2017518386A (ja) 2017-07-06
MX2016015690A (es) 2017-07-28
RU2703511C2 (ru) 2019-10-18
US20170137396A1 (en) 2017-05-18
CN106458950A (zh) 2017-02-22
AU2015276185A1 (en) 2016-12-01
ES2672932T3 (es) 2018-06-18
PL3157910T3 (pl) 2018-08-31
BR112016029597B1 (pt) 2021-08-10
RU2017101164A (ru) 2018-07-17
MA40011A (fr) 2018-03-14
RS57293B1 (sr) 2018-08-31
TR201807834T4 (tr) 2018-06-21
WO2015193364A1 (en) 2015-12-23
AU2015276185B2 (en) 2019-04-18
JP6626100B2 (ja) 2019-12-25
RU2017101164A3 (sl) 2019-01-23
CA2949436A1 (en) 2015-12-23
LT3157910T (lt) 2018-06-25
KR20170029419A (ko) 2017-03-15
NO3157910T3 (sl) 2018-08-11
HRP20180840T1 (hr) 2018-06-29
CA2949436C (en) 2022-05-17
MX365828B (es) 2019-06-17
KR102498728B1 (ko) 2023-02-10
BR112016029597A2 (pt) 2017-08-22
PT3157910T (pt) 2018-06-20
EP3157910B1 (en) 2018-03-14

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