PL146387B2 - Method of obtaining duroquinone - Google Patents
Method of obtaining duroquinone Download PDFInfo
- Publication number
- PL146387B2 PL146387B2 PL26324786A PL26324786A PL146387B2 PL 146387 B2 PL146387 B2 PL 146387B2 PL 26324786 A PL26324786 A PL 26324786A PL 26324786 A PL26324786 A PL 26324786A PL 146387 B2 PL146387 B2 PL 146387B2
- Authority
- PL
- Poland
- Prior art keywords
- oxidation
- cerium
- duroquinone
- diaminodurene
- anolyte
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- WAMKWBHYPYBEJY-UHFFFAOYSA-N duroquinone Chemical compound CC1=C(C)C(=O)C(C)=C(C)C1=O WAMKWBHYPYBEJY-UHFFFAOYSA-N 0.000 title claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 14
- 230000003647 oxidation Effects 0.000 claims description 12
- WCZNKVPCIFMXEQ-UHFFFAOYSA-N 2,3,5,6-tetramethylbenzene-1,4-diamine Chemical compound CC1=C(C)C(N)=C(C)C(C)=C1N WCZNKVPCIFMXEQ-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- -1 cerium (IV) ions Chemical class 0.000 claims description 3
- LJBTWTBUIINKRU-UHFFFAOYSA-K cerium(3+);triperchlorate Chemical compound [Ce+3].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O LJBTWTBUIINKRU-UHFFFAOYSA-K 0.000 claims description 2
- OZECDDHOAMNMQI-UHFFFAOYSA-H cerium(3+);trisulfate Chemical compound [Ce+3].[Ce+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O OZECDDHOAMNMQI-UHFFFAOYSA-H 0.000 claims 1
- XQTIWNLDFPPCIU-UHFFFAOYSA-N cerium(3+) Chemical compound [Ce+3] XQTIWNLDFPPCIU-UHFFFAOYSA-N 0.000 description 3
- 238000006056 electrooxidation reaction Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 108091006149 Electron carriers Proteins 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001785 cerium compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Opis patentowy opublikowano: 89 09 302 146 387 niania 3,6-diaminodurenu i proces elektrochemicznego utleniania ceru (III) jako przenosnika elektronów zachodza jednoczesnie w przestrzeni anodowej elektrolizera przeponowego z anoda z folii platynowej. Proces utleniania ulega zakonczeniu po ujawnieniu sie jonów (IV) w anolicie.Zaleta sposobu wedlug wynalazku jest to, ze mozna go prowadzic oszczednie i bezpiecznie w procesie ciaglym z wydajnoscia wynoszaca 94-96%, bez organicznych zanieczyszczen i bez wystepu¬ jacych scieków, a takze bez strat zwiazku ceru poddawanego regeneracji.Przedmiot wynalazku jest przedstawiony w nastepujacych przykladach wykonania. Reakcje chemiczna utleniania 3,6-diaminodurenu i proces elektrochemicznego utleniania ceru (III) prowa¬ dzi sie w elektrolizerze przeponowym przy uzyciu anody korzystnie cylindrycznej z folii platyno¬ wej, stosujac prad anodowy korzystnie o gestosci 25 A.m.~2.Przyklad I. 0,03 mola, to jest 4,93 czesci wagowych 3,6-diaminodurenu, po dodaniu do niego przy ciaglym mieszaniu w elektrolizerze 300 czesci objetosciowych wodnego roztworu kwasu nadchlorowego o stezeniu 2,0 mol. I"1 i nadchloranu cerawego o stezeniu 0,2 mol. I"1, poddaje sie utlenianiu przy przepuszczaniu pradu anodowego. Pojawienie sie w anolicie jonów ceru (IV) swiadczy o zakonczeniu reakcji utleniania 3,6-diaminodurenu do durochinonu cerem (IV), który powstaje w procesie anodowego utleniania ceru (III). Anolit poddaje sie filtracji i otrzymany czysty durochinon w postaci jasnozóltych krysztalów przemywa sie woda i suszy, uzyskujac 4,73 czesci wagowych gotowego produktu z wydajnoscia wynoszaca 96%. Temperatura topnienia otrzyma¬ nego durochinonu wynosi 110,5-112°C. Filtrat zawraca sie do elektrolizera i po dodaniu do niego takiej samej porcji 3,6.-diaminodurenu, wytwarzanie durochinonu prowadzi sie w dalszym ciagu, kontrolujac kwasowosc anolitu.Przyklad II. 0,03 mola, to jest 4,93 czesci wagowych 3,6-diaminodurenu, po dodaniu do przy ciaglym mieszaniu w elektrolizerze 300 czesci objetosciowych kwasu siarkowego o stezeniu 2,0 mol. I"1 i siarczanu cerawego o stezeniu 0,2 mol. 1~1, poddaje sie utlenianiu poprzez dalsze operacje w przykladzie I. Otrzymane 4,63 czesci wagowe gotowego produktu stanowi 94% wydajnosci.Temperaturatopnienia otrzymanego durochinonu wynosi 109,5-111,5°C. PLPatent description was published: 89 09 302 146 387 nannyation of 3,6-diaminodurene and the process of electrochemical oxidation of cerium (III) as an electron carrier takes place simultaneously in the anode space of a diaphragm electrolyser with a platinum foil anode. The oxidation process is terminated when the (IV) ions are revealed in the anolyte. The advantage of the process according to the invention is that it can be carried out economically and safely in a continuous process with an efficiency of 94-96%, without organic impurities and no waste water, and also without loss of the cerium compound being regenerated. The subject matter of the invention is illustrated in the following embodiments. The chemical oxidation of 3,6-diaminodurene and the electrochemical oxidation of cerium (III) are carried out in a diaphragm electrolyser using a preferably cylindrical anode made of platinum foil, using an anode current preferably with a density of 25 Am ~ 2. 3 moles, i.e. 4.93 parts by weight of 3,6-diaminodurene, after adding 300 parts by volume of an aqueous solution of 2.0 mole perchloric acid to it with constant stirring in an electrolyser. I "1 and cerium perchlorate with a concentration of 0.2 mol. I" 1 are subjected to oxidation by passing an anode current. The appearance of cerium (IV) ions in the anolyte proves the completion of the oxidation of 3,6-diaminodurene to duroquinone cerem (IV), which is formed in the anodic oxidation of cerium (III). The anolyte is filtered and the obtained pure duroquinone in the form of pale yellow crystals is washed with water and dried to give 4.73 parts by weight of the finished product with a yield of 96%. The melting point of the resulting duroquinone is 110.5-112 ° C. The filtrate is recycled to the electrolyser and after adding the same amount of 3,6-diaminodurene to it, the production of duroquinone is continued, controlling the acidity of the anolyte. Example II. 0.03 moles, that is 4.93 parts by weight of 3,6-diaminodurene, after adding 300 parts by volume of sulfuric acid at a concentration of 2.0 moles in an electrolyser continuously. I "1 and ceris sulphate with a concentration of 0.2 mol. 1 ~ 1, are subjected to oxidation by further operations in example I. The obtained 4.63 parts by weight of the finished product is 94% of the yield. The melting point of the obtained duroquinone is 109.5-111, 5 ° C. PL
Claims (6)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL26324786A PL146387B2 (en) | 1986-12-24 | 1986-12-24 | Method of obtaining duroquinone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL26324786A PL146387B2 (en) | 1986-12-24 | 1986-12-24 | Method of obtaining duroquinone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL263247A2 PL263247A2 (en) | 1987-12-28 |
| PL146387B2 true PL146387B2 (en) | 1989-01-31 |
Family
ID=20034233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL26324786A PL146387B2 (en) | 1986-12-24 | 1986-12-24 | Method of obtaining duroquinone |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL146387B2 (en) |
-
1986
- 1986-12-24 PL PL26324786A patent/PL146387B2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL263247A2 (en) | 1987-12-28 |
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