BR112014014054B1 - Método para produzir 5-hidroximetilfurfural - Google Patents
Método para produzir 5-hidroximetilfurfural Download PDFInfo
- Publication number
- BR112014014054B1 BR112014014054B1 BR112014014054-5A BR112014014054A BR112014014054B1 BR 112014014054 B1 BR112014014054 B1 BR 112014014054B1 BR 112014014054 A BR112014014054 A BR 112014014054A BR 112014014054 B1 BR112014014054 B1 BR 112014014054B1
- Authority
- BR
- Brazil
- Prior art keywords
- hmf
- starting solution
- steam
- solution
- distillate
- Prior art date
Links
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 title abstract description 63
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 title abstract description 63
- 238000004519 manufacturing process Methods 0.000 title abstract description 12
- 239000000243 solution Substances 0.000 claims abstract description 83
- 238000006243 chemical reaction Methods 0.000 claims abstract description 47
- 150000002402 hexoses Chemical class 0.000 claims abstract description 41
- 238000009835 boiling Methods 0.000 claims abstract description 38
- 239000007864 aqueous solution Substances 0.000 claims abstract description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- 238000004821 distillation Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 53
- 239000002253 acid Substances 0.000 claims description 20
- 239000005715 Fructose Substances 0.000 claims description 19
- 229930091371 Fructose Natural products 0.000 claims description 19
- 229920000570 polyether Polymers 0.000 claims description 18
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 17
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 10
- 239000010409 thin film Substances 0.000 claims description 9
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 8
- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 claims description 8
- 239000008103 glucose Substances 0.000 claims description 8
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 7
- DSLRVRBSNLHVBH-UHFFFAOYSA-N 2,5-furandimethanol Chemical compound OCC1=CC=C(CO)O1 DSLRVRBSNLHVBH-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- BJHIKXHVCXFQLS-UYFOZJQFSA-N fructose group Chemical group OCC(=O)[C@@H](O)[C@H](O)[C@H](O)CO BJHIKXHVCXFQLS-UYFOZJQFSA-N 0.000 claims description 2
- 239000000306 component Substances 0.000 description 28
- 239000006227 byproduct Substances 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 13
- 239000007858 starting material Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 125000001033 ether group Chemical group 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 238000001256 steam distillation Methods 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- -1 ethylene, propylene Chemical group 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- QGGBLTNZCCNDGV-UHFFFAOYSA-N 3-(chloromethyl)furan-2-carbaldehyde Chemical compound ClCC=1C=COC=1C=O QGGBLTNZCCNDGV-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- MEAKVFFLYQLKPB-UHFFFAOYSA-N methanesulfonic acid;oxalic acid Chemical compound CS(O)(=O)=O.OC(=O)C(O)=O MEAKVFFLYQLKPB-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- C07D307/38—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11193157 | 2011-12-13 | ||
| EP11193157.2 | 2011-12-13 | ||
| PCT/EP2012/075055 WO2013087613A1 (de) | 2011-12-13 | 2012-12-11 | Herstellung von 5-hydroxymethylfurfural (hmf) aus hexoselösungen in gegenwart von wasserdampf |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR112014014054A2 BR112014014054A2 (pt) | 2017-06-13 |
| BR112014014054B1 true BR112014014054B1 (pt) | 2019-03-19 |
Family
ID=47458896
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112014014054-5A BR112014014054B1 (pt) | 2011-12-13 | 2012-12-11 | Método para produzir 5-hidroximetilfurfural |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP2791126B1 (enExample) |
| JP (1) | JP6073363B2 (enExample) |
| KR (1) | KR101970853B1 (enExample) |
| CN (1) | CN104169263B (enExample) |
| BR (1) | BR112014014054B1 (enExample) |
| CA (1) | CA2856864C (enExample) |
| ES (1) | ES2626835T3 (enExample) |
| HU (1) | HUE033363T2 (enExample) |
| RU (1) | RU2014128460A (enExample) |
| WO (1) | WO2013087613A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9156802B2 (en) | 2011-12-13 | 2015-10-13 | Basf Se | Separating off 5-hydroxymethylfurfural (HMF) from reaction solutions by steam distillation |
| DE102016224073A1 (de) * | 2016-12-02 | 2018-06-07 | Südzucker AG | Verbessertes HMF-Herstellungsverfahren |
| EP3956319A1 (en) * | 2019-04-15 | 2022-02-23 | Stora Enso Oyj | Process for the recovery of solvent and isolation of humin materials and compositions thereof |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2929823A (en) * | 1956-11-26 | 1960-03-22 | Merck & Co Inc | Production of 5-hydroxymethylfurfural |
| US3201331A (en) * | 1962-10-17 | 1965-08-17 | Atlas Chem Ind | Purification of hydroxymethyl furfural |
| DE3601281A1 (de) | 1986-01-17 | 1987-07-23 | Sueddeutsche Zucker Ag | Verfahren zur herstellung von 5-hydroxymethylfurfural einschliesslich eines kristallinen produktes unter ausschliesslicher verwendung von wasser als loesungsmittel |
| FR2663933B1 (fr) * | 1990-06-27 | 1994-06-17 | Beghin Say Sa | Nouveau procede de preparation du 5-hydroxymethylfurfural a partir de saccharides. |
| EP1834950A1 (en) | 2006-03-10 | 2007-09-19 | Avantium International B.V. | Method for the synthesis of 5-alkoxymethylfurfural ethers and their use |
| ATE473218T1 (de) | 2006-03-10 | 2010-07-15 | Furanix Technologies Bv | Verwendung organischer säureester von 5- hydroxymethylfurfural |
| EP2033958A1 (en) * | 2007-09-07 | 2009-03-11 | Furanix Technologies B.V | Hydroxymethylfurfural ethers from sugars and di- and triols |
| CN101456850A (zh) * | 2007-12-12 | 2009-06-17 | 中国科学院大连化学物理研究所 | 一种制备5-羟甲基糠醛的方法 |
| CN101812039B (zh) * | 2010-05-14 | 2012-09-26 | 天津大学 | 一种利用离子液体催化生成5－羟甲基糠醛的方法 |
| CN102399203B (zh) * | 2011-12-19 | 2014-05-07 | 浙江大学 | 一种离子液体降解碳水化合物制备5-羟甲基糠醛的方法 |
-
2012
- 2012-12-11 KR KR1020147019046A patent/KR101970853B1/ko not_active Expired - Fee Related
- 2012-12-11 JP JP2014546456A patent/JP6073363B2/ja not_active Expired - Fee Related
- 2012-12-11 CA CA2856864A patent/CA2856864C/en not_active Expired - Fee Related
- 2012-12-11 BR BR112014014054-5A patent/BR112014014054B1/pt not_active IP Right Cessation
- 2012-12-11 EP EP12808306.0A patent/EP2791126B1/de not_active Not-in-force
- 2012-12-11 CN CN201280059056.3A patent/CN104169263B/zh not_active Expired - Fee Related
- 2012-12-11 HU HUE12808306A patent/HUE033363T2/en unknown
- 2012-12-11 RU RU2014128460A patent/RU2014128460A/ru not_active Application Discontinuation
- 2012-12-11 ES ES12808306.0T patent/ES2626835T3/es active Active
- 2012-12-11 WO PCT/EP2012/075055 patent/WO2013087613A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| ES2626835T3 (es) | 2017-07-26 |
| HUE033363T2 (en) | 2017-11-28 |
| JP2015500313A (ja) | 2015-01-05 |
| CN104169263A (zh) | 2014-11-26 |
| EP2791126B1 (de) | 2017-03-01 |
| KR20140101849A (ko) | 2014-08-20 |
| CA2856864C (en) | 2021-05-25 |
| BR112014014054A2 (pt) | 2017-06-13 |
| RU2014128460A (ru) | 2016-02-10 |
| CN104169263B (zh) | 2016-06-15 |
| WO2013087613A1 (de) | 2013-06-20 |
| JP6073363B2 (ja) | 2017-02-01 |
| KR101970853B1 (ko) | 2019-04-19 |
| CA2856864A1 (en) | 2013-06-20 |
| EP2791126A1 (de) | 2014-10-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B07A | Application suspended after technical examination (opinion) [chapter 7.1 patent gazette] | ||
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |
Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 11/12/2012, OBSERVADAS AS CONDICOES LEGAIS. |
|
| B21F | Lapse acc. art. 78, item iv - on non-payment of the annual fees in time |
Free format text: REFERENTE A 11A ANUIDADE. |
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| B24J | Lapse because of non-payment of annual fees (definitively: art 78 iv lpi, resolution 113/2013 art. 12) |
Free format text: EM VIRTUDE DA EXTINCAO PUBLICADA NA RPI 2752 DE 03-10-2023 E CONSIDERANDO AUSENCIA DE MANIFESTACAO DENTRO DOS PRAZOS LEGAIS, INFORMO QUE CABE SER MANTIDA A EXTINCAO DA PATENTE E SEUS CERTIFICADOS, CONFORME O DISPOSTO NO ARTIGO 12, DA RESOLUCAO 113/2013. |