PL161831B2 - Method of obtaining 2,5-furanedicarboxylic acid - Google Patents
Method of obtaining 2,5-furanedicarboxylic acidInfo
- Publication number
- PL161831B2 PL161831B2 PL28368090A PL28368090A PL161831B2 PL 161831 B2 PL161831 B2 PL 161831B2 PL 28368090 A PL28368090 A PL 28368090A PL 28368090 A PL28368090 A PL 28368090A PL 161831 B2 PL161831 B2 PL 161831B2
- Authority
- PL
- Poland
- Prior art keywords
- anode
- acid
- cathode
- hydroxymethylfurfural
- obtaining
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 16
- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 title claims description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 15
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 claims abstract description 9
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 8
- 230000003647 oxidation Effects 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 5
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical class Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 claims abstract description 4
- 229910000480 nickel oxide Inorganic materials 0.000 claims abstract description 4
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 claims abstract description 4
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 5
- PCSKKIUURRTAEM-UHFFFAOYSA-N 5-hydroxymethyl-2-furoic acid Chemical compound OCC1=CC=C(C(O)=O)O1 PCSKKIUURRTAEM-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 4
- 238000005868 electrolysis reaction Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- QAVITTVTXPZTSE-UHFFFAOYSA-N (5-formylfuran-2-yl)methyl acetate Chemical compound CC(=O)OCC1=CC=C(C=O)O1 QAVITTVTXPZTSE-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical class C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002473 artificial blood Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229960003328 benzoyl peroxide Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000108 silver(I,III) oxide Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
Landscapes
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Abstract
Description
Przedmiotem wynalazku jest sposób otrzymywania kwasu 2,5- furanodikarboksylowego. Związek ten jest stosowany jako kopolimer poprawiający wytrzymałość włókien politereftalowych oraz włókien poliamidowych używanych m.in. do wytwarzania sztucznych naczyń krwionośnych, a także - jako znany półprodukt do wytwarzania wysokoodpomych włókien syntetycznych i jako półprodukt do syntezy poliestrów.The subject of the invention is a process for the preparation of 2,5-furanedicarboxylic acid. This compound is used as a copolymer improving the strength of poly-terephthalic fibers and polyamide fibers used, among others, in for the manufacture of artificial blood vessels, as well as - as a known intermediate for the production of highly resistant synthetic fibers and as an intermediate for the synthesis of polyesters.
Jeden ze znanych sposobów otrzymywania kwasu 2,5- furanodikarboksylowego polega na przeprowadzeniu 5- hydroksymetylofurfuralu w 5-acetoksymetylofurfural i następnym utlenieniu uzyskanej pochodnej acetoksylowej nadmanganianem potasu w środowisku wodorotlenku sodowego w temperaturze 5°C (Karashima, Hoppe-Seyelers, Zeitschrift fur Physiologische Chemie 180, 243).One of the known methods of obtaining 2,5-furanedicarboxylic acid consists in converting 5-hydroxymethylfurfural into 5-acetoxymethylfurfural and subsequent oxidation of the obtained acetoxyl derivative with potassium permanganate in sodium hydroxide medium at 5 ° C (Karashima, Hoppe-Seyelers, Zeitschrift fur Physiologische Chemie Chemie 180 , 243).
Inny znany sposób otrzymywania omawianego związku polega na utlenieniu 5-hydroksymetylofurfuralu przy użyciu Ag2O - CuO jako katalizatorów, do kwasu 5-hydroksymetylo2-furanokarboksylowego, a następnie - na utlenianiu wytworzonego kwasu5-hydroksymetylo-2furanokarboksylowego, przy użyciu palladu lub platyny jako katalizatora, do produktu końcowego. Reakcje utleniania prowadzi się w wodnym roztworze wodorotlenku sodowego, nasyconym tlenem, w temperaturze 25°C, w ciągu 4,75 godziny opis patentowy USA nr 3 326 944.Another known method of obtaining the said compound consists in the oxidation of 5-hydroxymethylfurfural using Ag2O - CuO as catalysts, to 5-hydroxymethyl-2-furancarboxylic acid, and then - oxidation of the produced 5-hydroxymethyl-2-furancarboxylic acid, using palladium or platinum as a catalyst, to the product final. The oxidation reactions were carried out in an aqueous solution of sodium hydroxide saturated with oxygen at a temperature of 25 ° C for 4.75 hours in US Patent No. 3,326,944.
Znane są również sposoby bezpośredniego utleniania 5- hydroksymetylofurfuralu do kwasu 2,5-furanodikarboksylowego. Jednym z tych sposobów nasycania jest roztwór 5hydroksymetylofurfuralu w dimetylosulfotlenku czterotlenkiem dwuazotu i otrzymuje następnie mieszaninę reakcyjną w temperaturze 120°C. Drugim z tych sposobów uzyskuje się omawiany związek na drodze reakcji 5-hydroksymetylofurfuralu z kwasem azotowym w postaci 60% roztworu w dimetylosulfotlenku (Morikawa, Shunicki-Noguchi, Kenkyusho Jiho 1979 /22/, 20 - 27).Methods of direct oxidation of 5-hydroxymethylfurfural to 2,5-furanedicarboxylic acid are also known. One of these impregnation methods is a solution of 5-hydroxymethylfurfural in dimethylsulfoxide with dinitrogen tetroxide, and a reaction mixture is then obtained at 120 ° C. The second of these methods is the method of obtaining the compound by reacting 5-hydroxymethylfurfural with nitric acid in the form of a 60% solution in dimethylsulfoxide (Morikawa, Shunicki-Noguchi, Kenkyusho Jiho 1979/22 /, 20-27).
Omawiane sposoby są pracochłonne, w przypadku użycia drogich katalizatorów - kosztowne, a w przypadku stosowania czterotlenku dwuazotu bądź kwasu azotowego - niekorzystne z punktu widzenia bezpieczeństwa i higieny pracy.The discussed methods are labor-intensive, in the case of using expensive catalysts - expensive, and in the case of using dinitrogen tetroxide or nitric acid - unfavorable from the point of view of occupational health and safety.
Sposobem według wynalazku otrzymuje się kwas 2,5- furanodikarboksylowy na drodze elektrolitycznego utleniania 5- hydroksymetylofurfuralu. Proces prowadzi się w zasadowym środowisku wodnym, stosując jako anodę blaszkę niklową pokrytą tlenkiem niklowym, a jako katodę - blaszkę niklową, przy potencjale anody 0,600 V, mierzonym względem nasyconej elektrody kalomelowej, z przestrzenią anodową oddzieloną od przestrzeni katodowej za pomocą difragmy, a uzyskaną na drodze sól dwusodową kwasu 2,5-furanodikarboksylowego przeprowadza się w wolny kwas działaniem kwasu solnego, przy pH 2 - 3. Uzyskuje się z wydajnością powyżej 70% wagowych kwas 2,5-furanodikarboksylowy o wysokim stopniu czystości.The method of the invention produces 2,5-furanedicarboxylic acid by electrolytic oxidation of 5-hydroxymethylfurfural. The process is carried out in an alkaline aqueous environment, using a nickel plate coated with nickel oxide as an anode, and a nickel plate as a cathode, with an anode potential of 0.600 V, measured against a saturated calomel electrode, with the anode space separated from the cathode space by means of a diplex and obtained on thus, the disodium salt of 2,5-furanedicarboxylic acid is converted into the free acid by treatment with hydrochloric acid at a pH of 2 to 3. A yield of more than 70% by weight of 2,5-furanedicarboxylic acid is obtained in a high degree of purity.
Sposób według wynalazku ilustruje następujący przykład, w którym procenty oznaczają procenty wagowe, a stopnie temperatury podano w stopniach Celsjusza:The process of the invention is illustrated by the following example, in which the percentages are percentages by weight and the degrees of temperatures are in degrees Celsius:
161 831161 831
Przykład. Elektrolizę prowadzono w naczyniu szklanym typu H z celami rozdzielonymi spiekiem szklanym. W celi anodowej umieszczono roztwór 0,005 mola/0,63g/ 5-hydroksymetylofurfuralu win wodnym roztworze wodorotlenku sodowego. W celi katodowej umieszczono 1 n wodny roztwór wodorotlenku sodowego. Układ poddano anodowemu utlenianiu na anodzie niklowej pokrytej tlenkiem niklowym. Jako katody użyto blaszki niklowej. Elektrolizę prowadzono przy stałym potencjale anody 0,600 V względem nasyconej elektrody kalomelowej. Czas trwania elektrolizy wyniósł 4 godziny, a całkowity przeniesiony ładunek 3400 C, co stanowiło 118% ładunku teoretycznego. Przy zakończeniu elektrolizy zakwaszono anolit stężonym kwasem solnym do pH 2. Roztwór odstawiono do lodówki na 1 godzinę, a następnie odsączono żółty osad. Uzyskano 0.58 g kwasu 2,5-furanodikarboksylowego (71% wydajności). Uzyskany produkt nie topił się do 330°, lecz ulegał w określonej wyżej temperaturze częściowej sublimacji.Example. The electrolysis was carried out in a H-type glass vessel with cells separated by a sintered glass. A solution of 0.005 mol (0.63 g) of 5-hydroxymethylfurfural wine in aqueous sodium hydroxide was placed in the anode cell. A 1 N aqueous sodium hydroxide solution was placed in the cathode cell. The system was subjected to anodic oxidation on a nickel anode coated with nickel oxide. A nickel plate was used as the cathode. The electrolysis was run at a constant anode potential of 0.600 V relative to a saturated calomel electrode. The duration of the electrolysis was 4 hours, and the total transferred charge was 3400 C, which was 118% of the theoretical charge. Upon completion of the electrolysis, the anolyte was acidified with concentrated hydrochloric acid to pH 2. The solution was allowed to stand in the refrigerator for 1 hour and then the yellow precipitate was filtered off. 0.58 g of 2,5-furanedicarboxylic acid was obtained (71% yield). The product obtained did not melt up to 330 °, but was partially sublimated at the above-mentioned temperature.
161 831161 831
Zakład Wydawnictw UP RP. Nakład 90 egz.Department of Publishing of the UP RP. Circulation of 90 copies
Cena 10 000 złPrice: PLN 10,000
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL28368090A PL161831B2 (en) | 1990-02-06 | 1990-02-06 | Method of obtaining 2,5-furanedicarboxylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL28368090A PL161831B2 (en) | 1990-02-06 | 1990-02-06 | Method of obtaining 2,5-furanedicarboxylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL161831B2 true PL161831B2 (en) | 1993-08-31 |
Family
ID=20050174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL28368090A PL161831B2 (en) | 1990-02-06 | 1990-02-06 | Method of obtaining 2,5-furanedicarboxylic acid |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL161831B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2527316A1 (en) | 2007-11-14 | 2012-11-28 | BP Corporation North America Inc. | Terephthalic acid composition and use thereof for producing a polyester |
| WO2016186504A1 (en) | 2015-05-21 | 2016-11-24 | Avantium Knowledge Centre B.V. | Process for the preparation of an aromatic dicarboxylic acid |
| US20170145572A1 (en) * | 2015-01-08 | 2017-05-25 | Wisconsin Alumni Research Foundation | Electrochemical and photoelectrochemical oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid and 2,5-diformylfuran |
| US10435799B2 (en) | 2015-05-21 | 2019-10-08 | Avantium Knowledge Centre B.V. | Process for the purification of a carboxylic acid-containing composition |
-
1990
- 1990-02-06 PL PL28368090A patent/PL161831B2/en unknown
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2527316A1 (en) | 2007-11-14 | 2012-11-28 | BP Corporation North America Inc. | Terephthalic acid composition and use thereof for producing a polyester |
| US20170145572A1 (en) * | 2015-01-08 | 2017-05-25 | Wisconsin Alumni Research Foundation | Electrochemical and photoelectrochemical oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid and 2,5-diformylfuran |
| US10655233B2 (en) * | 2015-01-08 | 2020-05-19 | Wisconsin Alumni Research Foundation | Electrochemical and photoelectrochemical oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid and 2,5-diformylfuran |
| WO2016186504A1 (en) | 2015-05-21 | 2016-11-24 | Avantium Knowledge Centre B.V. | Process for the preparation of an aromatic dicarboxylic acid |
| US20180142362A1 (en) * | 2015-05-21 | 2018-05-24 | Avantium Knowledge Centre B.V. | Process for the Preparation of an Aromatic Dicarboxylic Acid |
| US10435799B2 (en) | 2015-05-21 | 2019-10-08 | Avantium Knowledge Centre B.V. | Process for the purification of a carboxylic acid-containing composition |
| US10787748B2 (en) * | 2015-05-21 | 2020-09-29 | Avantium Knowledge Centre B.V. | Process for the preparation of an aromatic dicarboxylic acid |
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