GB600871A - Improvements relating to the manufacture of 5-hydroxymethyl 2-furfural - Google Patents
Improvements relating to the manufacture of 5-hydroxymethyl 2-furfuralInfo
- Publication number
- GB600871A GB600871A GB2721045A GB2721045A GB600871A GB 600871 A GB600871 A GB 600871A GB 2721045 A GB2721045 A GB 2721045A GB 2721045 A GB2721045 A GB 2721045A GB 600871 A GB600871 A GB 600871A
- Authority
- GB
- United Kingdom
- Prior art keywords
- heated
- water containing
- sucrose
- furfural
- hydroxymethyl
- 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 6
- QVYAWBLDJPTXHS-UHFFFAOYSA-N 5-Hydroxymethyl-2-furfural Natural products OC1=CC=C(C=O)O1 QVYAWBLDJPTXHS-UHFFFAOYSA-N 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- 229930006000 Sucrose Natural products 0.000 abstract 3
- 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 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000005720 sucrose Substances 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 235000006408 oxalic acid Nutrition 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 2
- GZCGUPFRVQAUEE-UHFFFAOYSA-N 2,3,4,5,6-pentahydroxyhexanal Chemical compound OCC(O)C(O)C(O)C(O)C=O GZCGUPFRVQAUEE-UHFFFAOYSA-N 0.000 abstract 1
- AEMOLEFTQBMNLQ-UHFFFAOYSA-N 3,4,5,6-tetrahydroxyoxane-2-carboxylic acid Chemical compound OC1OC(C(O)=O)C(O)C(O)C1O AEMOLEFTQBMNLQ-UHFFFAOYSA-N 0.000 abstract 1
- 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 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003570 air Substances 0.000 abstract 1
- 229910000019 calcium carbonate Inorganic materials 0.000 abstract 1
- 150000001720 carbohydrates Chemical class 0.000 abstract 1
- 150000002016 disaccharides Chemical class 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 abstract 1
- 239000001530 fumaric acid Substances 0.000 abstract 1
- 239000008103 glucose Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000002402 hexoses Chemical class 0.000 abstract 1
- 239000002663 humin Substances 0.000 abstract 1
- 229940046892 lead acetate Drugs 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 239000011976 maleic acid Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 238000000638 solvent extraction Methods 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)
- Furan Compounds (AREA)
Abstract
5-Hydroxymethyl-2-furfural is obtained by heating a solution, having a pH value between 7 and 2, of a carbohydrate consisting of an aldohexose or ketohexose, or a disaccharide yielding either of the said hexoses, under pressure at a temperature between 130 DEG and 230 DEG C., the 5-hydroxymethyl-2-furfurfal being obtained from the mixture by solvent extraction. The reaction may be effected in an atmosphere of hydrogen, air or nitrogen. In examples: (1) sucrose and water are heated under pressure in hydrogen, the humin material formed is filtered off and the filtrate treated with calcium carbonate and basic lead acetate. After filtering, the solution is extracted by a solvent, e.g. ethyl acetate, the extract being finally dried and the solvent evaporated; (2) sorbose and water are heated under pressure in hydrogen and the product obtained as in (1) ; (3) sucrose and water containing phosphoric acid are heated in an autoclave and the reaction mixture treated as in (1) ; (4) to (9) crude cane juice is heated as in (3) with water containing oxalic acid and phosphoric acid respectively, sucrose is heated as in (3) with water containing maleic acid, fumaric acid and hydrochloric acid respectively and glucose is heated as in (3) with water containing oxalic acid. In each case the 5-hydroxy-methyl 2-furfural is obtained from the reactionmixture as in (1). Specification 591,858 is referred to.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB600871A true GB600871A (en) | 1948-04-21 |
Family
ID=1740460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2721045A Expired GB600871A (en) | 1945-10-17 | Improvements relating to the manufacture of 5-hydroxymethyl 2-furfural |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB600871A (en) |
Cited By (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2750394A (en) * | 1952-05-22 | 1956-06-12 | Food Chemical And Res Lab Inc | Manufacture of 5-hydroxymethyl 2-furfural |
| US2851468A (en) * | 1953-06-10 | 1958-09-09 | Dendrol Inc | Preparation of hydroxymethylfurfural from cellulosic materials |
| US2929823A (en) * | 1956-11-26 | 1960-03-22 | Merck & Co Inc | Production of 5-hydroxymethylfurfural |
| US3066150A (en) * | 1958-01-02 | 1962-11-27 | Merck & Co Inc | Conversion of invert molasses |
| DE1146891B (en) * | 1956-11-26 | 1963-04-11 | Merck & Co Inc | Process for the preparation of 5-oxymethylfurfural |
| WO2007146636A1 (en) | 2006-06-06 | 2007-12-21 | Wisconsin Alumni Research Foundation | Catalytic process for producing furan derivatives from carbohydrates in a biphasic reactor |
| 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 |
| US7897794B2 (en) | 2007-06-18 | 2011-03-01 | Archer Daniels Midland Company | Method for purifying hydroxymethylfurfural using non-functional polymeric resins |
| WO2012156479A1 (en) * | 2011-05-16 | 2012-11-22 | Centre National De La Recherche Scientifique (C.N.R.S) | Method for producing 5-hydroxymethylfurfural |
| 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 |
| US8669393B2 (en) | 2010-03-05 | 2014-03-11 | Rennovia, Inc. | Adipic acid compositions |
| US8669397B2 (en) | 2009-06-13 | 2014-03-11 | Rennovia, Inc. | Production of adipic acid and derivatives from carbohydrate-containing materials |
| 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 |
| US20140315262A1 (en) * | 2012-01-10 | 2014-10-23 | Archer Daniels Midland Company | Process for making hmf and hmf derivatives from sugars, with recovery of unreacted sugars suitable for direct fermentation to ethanol |
| US9073841B2 (en) | 2012-11-05 | 2015-07-07 | Segetis, Inc. | Process to prepare levulinic acid |
| CN105175367A (en) * | 2015-09-09 | 2015-12-23 | 江苏大学 | Method for converting sugar into 5-HMF (hydroxymethylfurfural) through acid catalysis |
| 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 |
| CN106117039B (en) * | 2016-06-17 | 2018-07-31 | 东莞理工学院 | A method of preparing sodium acetate using humin |
| 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 |
| US10618864B2 (en) | 2011-11-23 | 2020-04-14 | Gfbiochemicals Ip Assets B.V. | Process to prepare levulinic acid |
| US11192872B2 (en) | 2017-07-12 | 2021-12-07 | Stora Enso Oyj | Purified 2,5-furandicarboxylic acid pathway products |
-
1945
- 1945-10-17 GB GB2721045A patent/GB600871A/en not_active Expired
Cited By (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2750394A (en) * | 1952-05-22 | 1956-06-12 | Food Chemical And Res Lab Inc | Manufacture of 5-hydroxymethyl 2-furfural |
| US2851468A (en) * | 1953-06-10 | 1958-09-09 | Dendrol Inc | Preparation of hydroxymethylfurfural from cellulosic materials |
| US2929823A (en) * | 1956-11-26 | 1960-03-22 | Merck & Co Inc | Production of 5-hydroxymethylfurfural |
| DE1146891B (en) * | 1956-11-26 | 1963-04-11 | Merck & Co Inc | Process for the preparation of 5-oxymethylfurfural |
| US3066150A (en) * | 1958-01-02 | 1962-11-27 | Merck & Co Inc | Conversion of invert molasses |
| 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 |
| US7897794B2 (en) | 2007-06-18 | 2011-03-01 | Archer Daniels Midland Company | Method for purifying hydroxymethylfurfural using non-functional polymeric resins |
| 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 |
| US9174911B2 (en) | 2009-06-13 | 2015-11-03 | Rennovia Inc. | Production of glutaric 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 |
| US9434709B2 (en) | 2009-06-13 | 2016-09-06 | Rennovia Inc. | Production of adipic acid and derivatives from carbohydrate-containing materials |
| US8501989B2 (en) | 2009-06-13 | 2013-08-06 | 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 |
| 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 |
| US9156766B2 (en) | 2009-06-13 | 2015-10-13 | Rennovia Inc. | Production of adipic acid and derivatives from carbohydrate-containing materials |
| 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 |
| US9770705B2 (en) | 2010-06-11 | 2017-09-26 | Rennovia Inc. | Oxidation catalysts |
| US9808790B2 (en) | 2010-06-11 | 2017-11-07 | Rennovia Inc. | Processes for the manufacturing of oxidation catalysts |
| US10807074B2 (en) | 2010-06-11 | 2020-10-20 | Archer-Daniels-Midland Company | Oxidation catalysts |
| US9238635B2 (en) | 2011-05-16 | 2016-01-19 | Centre National De La Recherche Scientifique (C.N.R.S.) | Method for producing 5-hydroxymethylfurfural |
| FR2975396A1 (en) * | 2011-05-16 | 2012-11-23 | Centre Nat Rech Scient | PROCESS FOR THE PREPARATION OF 5-HYDROXYMETHYLFURFURAL |
| WO2012156479A1 (en) * | 2011-05-16 | 2012-11-22 | Centre National De La Recherche Scientifique (C.N.R.S) | Method for producing 5-hydroxymethylfurfural |
| US10618864B2 (en) | 2011-11-23 | 2020-04-14 | Gfbiochemicals Ip Assets B.V. | Process to prepare levulinic acid |
| US20140315262A1 (en) * | 2012-01-10 | 2014-10-23 | Archer Daniels Midland Company | Process for making hmf and hmf derivatives from sugars, with recovery of unreacted sugars suitable for direct fermentation to ethanol |
| WO2013109477A1 (en) | 2012-01-18 | 2013-07-25 | Rennovia, Inc. | Process for production of hexamethylenediamine from 5 - hydroxymethylfurfural |
| US9518005B2 (en) | 2012-01-18 | 2016-12-13 | 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 |
| US9035109B2 (en) | 2012-01-18 | 2015-05-19 | 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 |
| US9598341B2 (en) | 2012-11-05 | 2017-03-21 | Gfbiochemicals Limited | Process to prepare levulinic acid |
| US9073841B2 (en) | 2012-11-05 | 2015-07-07 | Segetis, Inc. | Process to prepare levulinic acid |
| 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 |
| US9586920B2 (en) | 2014-12-02 | 2017-03-07 | Rennovia Inc. | Process for production of hexanetriol from 5-hydroxymethylfurfural |
| US10081612B2 (en) | 2014-12-02 | 2018-09-25 | Archer-Daniels-Midland Company | Process for production of hexanetriol from 5-hydroxymethylfurfural |
| CN105175367A (en) * | 2015-09-09 | 2015-12-23 | 江苏大学 | Method for converting sugar into 5-HMF (hydroxymethylfurfural) through acid catalysis |
| 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 |
| 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 |
| 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 |
| 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 |
| CN106117039B (en) * | 2016-06-17 | 2018-07-31 | 东莞理工学院 | A method of preparing sodium acetate using humin |
| 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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