GB876463A - Process for preparing hydroxymethyl furfural - Google Patents
Process for preparing hydroxymethyl furfuralInfo
- Publication number
- GB876463A GB876463A GB6201/60A GB620160A GB876463A GB 876463 A GB876463 A GB 876463A GB 6201/60 A GB6201/60 A GB 6201/60A GB 620160 A GB620160 A GB 620160A GB 876463 A GB876463 A GB 876463A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- mixture
- dioxane
- hexose
- hydroxymethyl furfural
- 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.)
- Expired
Links
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 title abstract 2
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 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 abstract 3
- 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 abstract 3
- 150000002402 hexoses Chemical class 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 239000003377 acid catalyst Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000008121 dextrose Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- SXQXMKMHOFIAHT-UHFFFAOYSA-N 1,1-dichloro-2-(2,2-dichloroethoxy)ethane Chemical compound ClC(Cl)COCC(Cl)Cl SXQXMKMHOFIAHT-UHFFFAOYSA-N 0.000 abstract 1
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 abstract 1
- AWBIJARKDOFDAN-UHFFFAOYSA-N 2,5-dimethyl-1,4-dioxane Chemical compound CC1COC(C)CO1 AWBIJARKDOFDAN-UHFFFAOYSA-N 0.000 abstract 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 abstract 1
- YBDQLHBVNXARAU-UHFFFAOYSA-N 2-methyloxane Chemical compound CC1CCCCO1 YBDQLHBVNXARAU-UHFFFAOYSA-N 0.000 abstract 1
- 229910021555 Chromium Chloride Inorganic materials 0.000 abstract 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 abstract 1
- 229930091371 Fructose Natural products 0.000 abstract 1
- 239000005715 Fructose Substances 0.000 abstract 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 abstract 1
- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 abstract 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 abstract 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 abstract 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 1
- 229920002472 Starch Polymers 0.000 abstract 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 abstract 1
- 229930006000 Sucrose Natural products 0.000 abstract 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Inorganic materials [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- -1 aliphatic ketones Chemical class 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 239000008103 glucose Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 235000013379 molasses Nutrition 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000008107 starch Substances 0.000 abstract 1
- 235000019698 starch Nutrition 0.000 abstract 1
- 239000005720 sucrose Substances 0.000 abstract 1
- 235000000346 sugar Nutrition 0.000 abstract 1
- 150000008163 sugars Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 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)
- Saccharide Compounds (AREA)
Abstract
Hydroxymethyl furfural is made by dehydrating a hexose, or a hexose polymer which yields simple hexoses on acid hydrolysis, at an elevated temperature in the presence of an acid catalyst and in a reaction medium comprising a mixture which contains from 5% to 70% by weight of water and correspondingly from 95% to 30% of an organic liquid having a normal boiling point no greater than about 280 DEG C. selected from acid-stable aliphatic ketones and acid-stable aliphatic and cycloaliphatic ethers. Specified examples are methyl isobutyl ketone, mesityl oxide, dichlorethyl ether, dioxane, glycol monoethyl ether, symmetrical dimethyl dioxane, tetrahydropyran and tetrahydro-2-methyl pyran. Suitable sugars for conversion are glucose, fructose, sorbose, mannose, sucrose and maltose. Molasses and starch conversion liquors containing dextrose and dextrose polymers are also suitable. The acid catalyst may be, for example, a mineral acid, toluene sulphonic acid, acetic acid, aluminium, zinc or chromium chloride, or a mixture of an acid and an acidic metal salt. Specification 817,139 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US876463XA | 1959-02-25 | 1959-02-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB876463A true GB876463A (en) | 1961-09-06 |
Family
ID=22206405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6201/60A Expired GB876463A (en) | 1959-02-25 | 1960-02-22 | Process for preparing hydroxymethyl furfural |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB876463A (en) |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2464260A1 (en) * | 1979-09-05 | 1981-03-06 | Roquette Freres | PROCESS FOR PRODUCING 5-HYDROXYMETHYLFURFURAL |
| WO1996017837A1 (en) * | 1994-12-07 | 1996-06-13 | Agrichimie | Method for making hydroxymethylfurfural from aldohexose |
| WO2007146636A1 (en) | 2006-06-06 | 2007-12-21 | Wisconsin Alumni Research Foundation | Catalytic process for producing furan derivatives from carbohydrates in a biphasic reactor |
| DE102008009933A1 (en) | 2008-02-18 | 2009-08-20 | Friedrich-Schiller-Universität Jena | Preparing 5-hydroxymethylfurfural, useful e.g. to manufacture pharmaceutical products such as fungicides, comprises thermally reacting carbohydrates in ionic liquid and discharging formed 5-hydroxymethylfurfural using extracting agent |
| WO2010144873A1 (en) | 2009-06-13 | 2010-12-16 | Rennovia, Inc. | Production of adipic acid and derivatives from carbohydrate-containing materials |
| US7880049B2 (en) | 2006-06-06 | 2011-02-01 | Wisconsin Alumni Research Foundation | Production of liquid alkanes in the jet fuel range (C8-C15) from biomass-derived carbohydrates |
| WO2011161141A1 (en) * | 2010-06-22 | 2011-12-29 | Shell Internationale Research Maatschappij B.V. | Process for separating furfural from a liquid aqueous phase comprising furfural and one or more organic acids |
| US8314267B2 (en) | 2009-06-26 | 2012-11-20 | Uop Llc | Carbohydrate route to para-xylene and terephthalic acid |
| US8324376B2 (en) | 2008-06-17 | 2012-12-04 | Wisconsin Alumni Research Foundation | Chemical transformation of lignocellulosic biomass into fuels and chemicals |
| WO2013109477A1 (en) | 2012-01-18 | 2013-07-25 | Rennovia, Inc. | Process for production of hexamethylenediamine from 5 - hydroxymethylfurfural |
| US8669397B2 (en) | 2009-06-13 | 2014-03-11 | Rennovia, Inc. | Production of adipic acid and derivatives from carbohydrate-containing materials |
| US8669393B2 (en) | 2010-03-05 | 2014-03-11 | Rennovia, Inc. | Adipic acid compositions |
| US8722878B2 (en) | 2009-07-01 | 2014-05-13 | Wisconsin Alumni Research Foundation | Biomass hydrolysis |
| US8785683B2 (en) | 2009-06-13 | 2014-07-22 | Rennovia, Inc. | Production of glutaric acid and derivatives from carbohydrate-containing materials |
| CN105658632A (en) * | 2013-08-29 | 2016-06-08 | 韩国生产技术研究院 | Process for the preparation of 5-hydroxymethyl-2-furfural using an acid catalyst in the presence of a biomass-derived ethylene glycol-based compound solvent |
| US9586920B2 (en) | 2014-12-02 | 2017-03-07 | Rennovia Inc. | Process for production of hexanetriol from 5-hydroxymethylfurfural |
| US9611241B2 (en) | 2014-01-27 | 2017-04-04 | Rennovia Inc. | Conversion of fructose-containing feedstocks to HMF-containing product |
| US9770705B2 (en) | 2010-06-11 | 2017-09-26 | Rennovia Inc. | Oxidation catalysts |
| 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 |
| US11192872B2 (en) | 2017-07-12 | 2021-12-07 | Stora Enso Oyj | Purified 2,5-furandicarboxylic acid pathway products |
-
1960
- 1960-02-22 GB GB6201/60A patent/GB876463A/en not_active Expired
Cited By (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2464260A1 (en) * | 1979-09-05 | 1981-03-06 | Roquette Freres | PROCESS FOR PRODUCING 5-HYDROXYMETHYLFURFURAL |
| WO1996017837A1 (en) * | 1994-12-07 | 1996-06-13 | Agrichimie | Method for making hydroxymethylfurfural from aldohexose |
| FR2727967A1 (en) * | 1994-12-07 | 1996-06-14 | Agrichimie Sa | PROCESS FOR THE MANUFACTURE OF HYDROXYMETHYLFURFURAL FROM ALDOHEXOSE |
| WO2007146636A1 (en) | 2006-06-06 | 2007-12-21 | Wisconsin Alumni Research Foundation | Catalytic process for producing furan derivatives from carbohydrates in a biphasic reactor |
| US7572925B2 (en) | 2006-06-06 | 2009-08-11 | Wisconsin Alumni Research Foundation | Catalytic process for producing furan derivatives in a biphasic reactor |
| US7880049B2 (en) | 2006-06-06 | 2011-02-01 | Wisconsin Alumni Research Foundation | Production of liquid alkanes in the jet fuel range (C8-C15) from biomass-derived carbohydrates |
| DE102008009933A1 (en) | 2008-02-18 | 2009-08-20 | Friedrich-Schiller-Universität Jena | Preparing 5-hydroxymethylfurfural, useful e.g. to manufacture pharmaceutical products such as fungicides, comprises thermally reacting carbohydrates in ionic liquid and discharging formed 5-hydroxymethylfurfural using extracting agent |
| US8324376B2 (en) | 2008-06-17 | 2012-12-04 | Wisconsin Alumni Research Foundation | Chemical transformation of lignocellulosic biomass into fuels and chemicals |
| US8680264B2 (en) | 2008-06-17 | 2014-03-25 | Wisconsin Alumni Research Foundation | Chemical transformation of lignocellulosic biomass into fuels and chemicals |
| US8501989B2 (en) | 2009-06-13 | 2013-08-06 | Rennovia, Inc. | Production of adipic acid and derivatives from carbohydrate-containing materials |
| US8927768B2 (en) | 2009-06-13 | 2015-01-06 | Rennovia, Inc. | Production of adipic acid and derivatives from carbohydrate-containing materials |
| US9174911B2 (en) | 2009-06-13 | 2015-11-03 | Rennovia Inc. | Production of glutaric acid and derivatives from carbohydrate-containing materials |
| US9434709B2 (en) | 2009-06-13 | 2016-09-06 | Rennovia Inc. | Production of adipic acid and derivatives from carbohydrate-containing materials |
| US8669397B2 (en) | 2009-06-13 | 2014-03-11 | Rennovia, Inc. | Production of adipic acid and derivatives from carbohydrate-containing materials |
| US9156766B2 (en) | 2009-06-13 | 2015-10-13 | Rennovia Inc. | Production of adipic acid and derivatives from carbohydrate-containing materials |
| WO2010144873A1 (en) | 2009-06-13 | 2010-12-16 | Rennovia, Inc. | Production of adipic acid and derivatives from carbohydrate-containing materials |
| US8785683B2 (en) | 2009-06-13 | 2014-07-22 | Rennovia, Inc. | Production of glutaric acid and derivatives from carbohydrate-containing materials |
| US8314267B2 (en) | 2009-06-26 | 2012-11-20 | Uop Llc | Carbohydrate route to para-xylene and terephthalic acid |
| US8722878B2 (en) | 2009-07-01 | 2014-05-13 | Wisconsin Alumni Research Foundation | Biomass hydrolysis |
| US8669393B2 (en) | 2010-03-05 | 2014-03-11 | Rennovia, Inc. | Adipic acid compositions |
| US11596927B2 (en) | 2010-06-11 | 2023-03-07 | Archer-Daniels-Midland Company | Oxidation catalysts |
| US10807074B2 (en) | 2010-06-11 | 2020-10-20 | Archer-Daniels-Midland Company | Oxidation catalysts |
| US9808790B2 (en) | 2010-06-11 | 2017-11-07 | Rennovia Inc. | Processes for the manufacturing of oxidation catalysts |
| US9770705B2 (en) | 2010-06-11 | 2017-09-26 | Rennovia Inc. | Oxidation catalysts |
| WO2011161141A1 (en) * | 2010-06-22 | 2011-12-29 | Shell Internationale Research Maatschappij B.V. | Process for separating furfural from a liquid aqueous phase comprising furfural and one or more organic acids |
| WO2013109477A1 (en) | 2012-01-18 | 2013-07-25 | Rennovia, Inc. | Process for production of hexamethylenediamine from 5 - hydroxymethylfurfural |
| US9035109B2 (en) | 2012-01-18 | 2015-05-19 | Rennovia, Inc. | Process for production of hexamethylenediamine from carbohydrate-containing materials and intermediates therefor |
| US8853458B2 (en) | 2012-01-18 | 2014-10-07 | Rennovia, Inc. | Process for production of hexamethylenediamine from carbohydrate-containing materials and intermediates therefor |
| EP3466919A1 (en) | 2012-01-18 | 2019-04-10 | Archer-Daniels-Midland Company | Process for production of 1,6-hexanediol from 1,2-6-hexanetriol |
| US9518005B2 (en) | 2012-01-18 | 2016-12-13 | Rennovia Inc. | Process for production of hexamethylenediamine from carbohydrate-containing materials and intermediates therefor |
| US9783473B2 (en) | 2012-01-18 | 2017-10-10 | Rennovia Inc. | Process for production of hexamethylenediamine from carbohydrate-containing materials and intermediates therefor |
| CN105658632A (en) * | 2013-08-29 | 2016-06-08 | 韩国生产技术研究院 | Process for the preparation of 5-hydroxymethyl-2-furfural using an acid catalyst in the presence of a biomass-derived ethylene glycol-based compound solvent |
| US9802910B2 (en) * | 2013-08-29 | 2017-10-31 | Korea Institute Of Industrial Technology | Method for preparing 5-hydroxymethyl-2-furfural using acid catalyst in presence of ethylene glycol-based compound solvent derived from biomass |
| CN105658632B (en) * | 2013-08-29 | 2018-07-06 | 韩国生产技术研究院 | Process for the preparation of 5-hydroxymethyl-2-furfural using an acid catalyst in the presence of a biomass-derived ethylene glycol-based compound solvent |
| US20160207896A1 (en) * | 2013-08-29 | 2016-07-21 | Korea Institute Of Industrial Technology | Method for preparing 5-hydroxymethyl-2-furfural using acid catalyst in presence of ethylene glycol-based compound solvent derived from biomass |
| US10017486B2 (en) | 2014-01-27 | 2018-07-10 | Archer-Daniels-Midland Company | Conversion of fructose-containing feedstocks to HMF-containing product |
| US9611241B2 (en) | 2014-01-27 | 2017-04-04 | Rennovia Inc. | Conversion of fructose-containing feedstocks to HMF-containing product |
| US10081612B2 (en) | 2014-12-02 | 2018-09-25 | Archer-Daniels-Midland Company | Process for production of hexanetriol from 5-hydroxymethylfurfural |
| US9586920B2 (en) | 2014-12-02 | 2017-03-07 | Rennovia Inc. | Process for production of hexanetriol from 5-hydroxymethylfurfural |
| 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 |
| 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 |
| 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 |
| 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 |
| US11192872B2 (en) | 2017-07-12 | 2021-12-07 | Stora Enso Oyj | Purified 2,5-furandicarboxylic acid pathway products |
| US12049456B2 (en) | 2017-07-12 | 2024-07-30 | Stora Enso Oyj | Purified 2,5-furandicarboxylic acid pathway products |
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