PL365B1 - Method for obtaining anthraquinone and its derivatives. - Google Patents
Method for obtaining anthraquinone and its derivatives. Download PDFInfo
- Publication number
- PL365B1 PL365B1 PL365A PL36520A PL365B1 PL 365 B1 PL365 B1 PL 365B1 PL 365 A PL365 A PL 365A PL 36520 A PL36520 A PL 36520A PL 365 B1 PL365 B1 PL 365B1
- Authority
- PL
- Poland
- Prior art keywords
- anthraquinone
- derivatives
- anthracene
- obtaining
- mixture
- Prior art date
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- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title claims description 7
- 150000004056 anthraquinones Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 4
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 3
- 150000002730 mercury Chemical class 0.000 claims description 2
- 239000000375 suspending agent Substances 0.000 claims description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 241000193738 Bacillus anthracis Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PIKZHTNNKKFXSW-UHFFFAOYSA-N [N].[Hg] Chemical compound [N].[Hg] PIKZHTNNKKFXSW-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- VRJVVIKEWDDYOG-UHFFFAOYSA-N mercury;nitric acid Chemical compound [Hg].O[N+]([O-])=O VRJVVIKEWDDYOG-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Description
W niemieckim patencie Nr 268 049 zo¬ stal opisany sposób otrzymywania antra¬ chinonu, polegajacy na tern, ze dziala sie przy ogrzaniu dwutlenkiem azotu na antra¬ cen w obecnosci srodka rozpuszczajacego lub dajacego zawiesiny. Sposób ten daje przy uzyciu czystego antracenu prawie ilo¬ sciowa wydajnosc czystego antrachinonu.Jezeli jednak wezmiemy do tej reakcji techniczny antracen (czysty antracen moz¬ na, jak wiadomo, otrzymac tylko z an¬ trachinonu), to otrzymuje sie rezultaty niezgodne z teorja, a mianowicie antra- chinon zanieczyszczony ptfzez nitro- zwiazki. Wykazano jednak, ze mozna otrzymac ilosc czystego antracenu o wie¬ le wieksza, prawie wydajnosc ilosciowa, nawet przy technicznych gatunkach an¬ tracenu, gdy do mieszaniny reakcyjnej doda sie soli rteciowych.Przyklad. Do 400 g nitrobenzolu do¬ daje sie sproszkowana mieszanine 109.5 g antracenu o 91,3% zawartosci i 10 g azotowej soli rteciowej. Potem dodaje sie kolo 170 g dwutlenku azotu w prze¬ ciagu 1% godziny, mieszajac i ochladza¬ jac mieszanine reakcyjna, i pozostawia sie na noc. Nastepnie doprowadza sie temperature mieszaniny w przeciagu 75 minut do 100°, a wreszcie ogrzewa sie na lazni olejnej do 100°^1!10° przez 8 godz przy ciagiem mieszaniu. Po wystygnieciunalezy mieszanine wycisnac, przemyc ni¬ trobenzenem i eterem naftowym i wysu¬ szyc. Otrzymane krysztaly antrachinonu nalezy wygotowac z rozcienczonym kwa¬ sem azotowym. Mozna jednak uniknac gotowania z kwasem azotowym, jezeli po skonczonej reakcji, wedlug wskazówek patentu niemieckiego Nr 283213, bedziemy przepuszczac krótki czas chlor przy na¬ grzewaniu. W ten sposób otrzymuje sie ze 100 czesci antracenu 109 do 115 czesci an¬ trachinonu, podczas gdy bez uzycia soli rteciowej kwasu azotowego otrzymuje sie tylko 88 do 95 czesci antrachinonu. PLThe German patent No. 268,049 describes a method for the preparation of anthraquinone, which is based on the fact that it operates on heating with nitrogen dioxide on the anthrax in the presence of a dissolving or suspending agent. This method gives an almost quantitative yield of pure anthracene with pure anthracene. However, if we use technical anthracene in this reaction (pure anthracene can be obtained only from anthracene), the results are inconsistent with the theory and namely, anthraquinone contaminated with a nitro compound. However, it has been shown that it is possible to obtain a quantity of pure anthracene with a much greater, almost quantitative yield, even with technical anthracene grades, when mercury salts are added to the reaction mixture. To 400 g of nitrobenzole is added a powdered mixture of 109.5 g of 91.3% anthracene and 10 g of mercury nitrogen salt. Thereafter, approximately 170 g of nitrogen dioxide are added over a 1% hour, while stirring, and the reaction mixture is cooled, and left to stand overnight. The temperature of the mixture is then brought to 100 ° for 75 minutes and finally heated in an oil bath to 100 ° -1.10 ° for 8 hours with continuous agitation. After the mixture has cooled down, squeeze the mixture, wash with nitrobenzene and petroleum ether and dry. The obtained anthraquinone crystals should be boiled with diluted nitric acid. However, cooking with nitric acid can be avoided if, after the reaction is finished, we let chlorine pass through the heating for a short time according to the instructions of German Patent No. 283213. Thus, 100 parts of anthracene 109 to 115 parts of anthraquinone are obtained, while without the use of nitric acid mercury, only 88 to 95 parts of anthraquinone are obtained. PL
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL365B1 true PL365B1 (en) | 1924-07-30 |
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