GB817139A - Preparation of 5-hydroxymethyl 2-furfural - Google Patents
Preparation of 5-hydroxymethyl 2-furfuralInfo
- Publication number
- GB817139A GB817139A GB1322356A GB1322356A GB817139A GB 817139 A GB817139 A GB 817139A GB 1322356 A GB1322356 A GB 1322356A GB 1322356 A GB1322356 A GB 1322356A GB 817139 A GB817139 A GB 817139A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- furfural
- sulphuric acid
- sucrose
- heated
- 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 8
- QVYAWBLDJPTXHS-UHFFFAOYSA-N 5-Hydroxymethyl-2-furfural Natural products OC1=CC=C(C=O)O1 QVYAWBLDJPTXHS-UHFFFAOYSA-N 0.000 title abstract 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 4
- 239000001117 sulphuric acid Substances 0.000 abstract 4
- 235000011149 sulphuric acid Nutrition 0.000 abstract 4
- 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
- 229930006000 Sucrose Natural products 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- 239000005720 sucrose Substances 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 150000007522 mineralic acids Chemical class 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- FLDFNEBHEXLZRX-RUAPLKMPSA-N (2S,5S)-2-[(2S,5R)-2-[[(2R,5R)-2-[[(2R,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound OC[C@H]1O[C@@](CO)(OC[C@@]2(OC[C@@]3(O[C@@H]4OC(CO)[C@@H](O)C(O)C4O)O[C@H](CO)C(O)C3O)O[C@H](CO)C(O)C2O)C(O)C1O FLDFNEBHEXLZRX-RUAPLKMPSA-N 0.000 abstract 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-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
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 1
- 244000298479 Cichorium intybus Species 0.000 abstract 1
- 235000007542 Cichorium intybus Nutrition 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
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003729 cation exchange resin Substances 0.000 abstract 1
- 229960002737 fructose Drugs 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 229960004903 invert sugar Drugs 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 235000010755 mineral Nutrition 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 235000013379 molasses Nutrition 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 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 produced by heating an aqueous solution of a keto-hexose sugar at a temperature between 125 DEG and 225 DEG C. in the presence of an unsubstituted saturated aliphatic monohydric alcohol, preferably having from 1 to 5 carbon atoms in the molecule, the molar ratio of the alcohol to water in the solution being between 0.1 and 0.4. Preferably a catalyst is used. An acidic catalyst, i.e. an inorganic or organic acid or a substance which generates an inorganic or organic acid radical is used, e.g. hydrochloric acid, hydrobromic acid, phosphoric acid, zinc chloride and aluminium chloride. The preferred catalysts are strong mineral acids, especially sulphuric acid. In some cases it may be desirable to stop the reaction before the maximum yield of 5-hydroxy methyl-2-furfural is obtained. In the examples: (a) levulose, dilute sulphuric acid and n-butyl alcohol are heated together at 170 DEG C.; (b) sucrose, dilute sulphuric acid and n-butyl alcohol are heated together at 150 DEG C. in two stages; (c) crude black-strap molasses is diluted with water and de-ashed by passage over a column of cation exchange resin; this solution is mixed with butanol and heated at 150 DEG C.; and (d) various mixtures of sucrose, sulphuric acid, n-butyl alcohol and water are heated at 150 DEG C. In all cases 5-hydroxymethyl-2-furfural is obtained. Another material which may be used as starting material is inulin from Jerusalem artichoke tubers or chicory. When sucrose is used as starting material it is rapidly hydrolysed to invert sugar. Specifications 591,858, [Group IV], 600,871 and U.S.A. Specification 2,498,918 are referred to.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB817139A true GB817139A (en) | 1959-07-22 |
Family
ID=1725727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1322356A Expired GB817139A (en) | 1956-04-30 | Preparation of 5-hydroxymethyl 2-furfural |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB817139A (en) |
Cited By (2)
| 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 |
-
1956
- 1956-04-30 GB GB1322356A patent/GB817139A/en not_active Expired
Cited By (3)
| 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 |
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