DE576176C - Process for the production of oxidation products of the benzanthrone series - Google Patents
Process for the production of oxidation products of the benzanthrone seriesInfo
- Publication number
- DE576176C DE576176C DE1930576176D DE576176DD DE576176C DE 576176 C DE576176 C DE 576176C DE 1930576176 D DE1930576176 D DE 1930576176D DE 576176D D DE576176D D DE 576176DD DE 576176 C DE576176 C DE 576176C
- Authority
- DE
- Germany
- Prior art keywords
- production
- oxidation products
- benzanthrone
- benzanthrone series
- series
- 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
- 230000003647 oxidation Effects 0.000 title claims description 5
- 238000007254 oxidation reaction Methods 0.000 title claims description 5
- HUKPVYBUJRAUAG-UHFFFAOYSA-N 7-benzo[a]phenalenone Chemical class C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000003518 caustics Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- VKKAQEPQMRFGIQ-UHFFFAOYSA-N 1-methylbenzo[b]phenalen-7-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3C3=C2C1=CC=C3C VKKAQEPQMRFGIQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 150000005181 nitrobenzenes Chemical class 0.000 claims description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 1
- PUYNGXBFZSNLCX-UHFFFAOYSA-N 7-oxobenzo[a]phenalene-2-carbaldehyde Chemical compound C1=C(C=C2C=CC=C3C(=O)C4=CC=CC=C4C1=C23)C=O PUYNGXBFZSNLCX-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical class [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- ZJRXSAYFZMGQFP-UHFFFAOYSA-N barium peroxide Chemical compound [Ba+2].[O-][O-] ZJRXSAYFZMGQFP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 235000012255 calcium oxide Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/02—Benzathrones
- C09B3/06—Preparation from starting materials already containing the benzanthrone nucleus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Oxydationsprodukten der Benzanthronreihe In dem Patent 479917 ist ein Verfahren zur Herstellung von BenzanthToncarbonsäuren beschrieben, welches darin besteht, daß man auf Alkylbenzanthrone in Gegenhart alkalischer Mittel Nitrobenzol einwirken läßt. Verwendet man als alkalische Mittel die in den Beispielen angegebenen Ätzalkalien, so verläuft die Reaktion ziemlich heftig und ist in größerem Maßstabe schwer zu regulieren.Process for the production of oxidation products of the benzanthrone series In the patent 479917 there is a process for the production of benzanthonecarboxylic acids described, which consists in the fact that one is alkaline on alkylbenzanthrones in Gegenhart Agent Nitrobenzene lets act. Is used as an alkaline agent in the Examples given caustic alkalis, the reaction proceeds quite violently and is difficult to regulate on a large scale.
Es wurde nun gefunden, däß. man ebenfalls wertvolle Oxydationsprodukte der Methylbenzanthrone erhalten kann, wenn man diese letzteren in Gegenwart von Nitrobenzolen mit milder als Ätzalkalien wirkenden alkalischen Mitteln bei höheren Temperaturen behandelt und die Reaktion unterbricht, ehe wesentliche Mengen Carbonsäuren gebildet sind. Die erhaltenen Körper sind ihrem Verhalten nach vermutlich Aldehyde der Benzanthronreihe. Man kann milder als Ätzalkalien wirkende alkalische Mittel, z. B. Oxyde; Hydroxyde oder SuperoXyde der Erdalkalimetalle oder Salze der Alkali- oder Erdalkalimetalle mit schwachen Säuren, verwenden. Die Oxydation verläuft unter diesen Bedingungen nicht heftig und ist namentlich in größerem Maßstabe leicht zu regulieren.It has now been found that. there are also valuable oxidation products the methylbenzanthrones can be obtained when these latter in the presence of Nitrobenzenes with milder alkaline agents than caustic alkalis at higher levels Treated temperatures and interrupted the reaction before substantial amounts of carboxylic acids are formed. According to their behavior, the bodies obtained are presumably aldehydes the benzanthrone series. You can use alkaline agents that are milder than caustic alkalis, z. B. Oxides; Hydroxides or super oxides of the alkaline earth metals or salts of the alkali or alkaline earth metals with weak acids. The oxidation runs under under these conditions it is not violent, and especially on a larger scale it is easy regulate.
Beispiel 12,2 Teile a-Methylenb enzanthron, r 5o Teile Nitrobenzol und 17 Teile gepuh#erter gebrannter Kalk werden 5 bis io Stunden lang gekocht. Die Reaktionsmasse wird durch Wasserdampfdestillation-vomüberschüssigen Nitrobenzol befreit, der Rückstand mit «Wasser gewaschen und getrocknet. Er besteht zum größten Teil aus Benzanthron-2-aldehyd, das sich z. B. durch Uml,-xistallisieren aus organischen Lösungsmitteln reinigen und gewünschtenfalls in die entsprechende Carbonsäure überführen läßt.Example 12.2 T rush a-Methylenb enzanthron, r 5o parts of nitrobenzene and 1 7 parts gepuh # erter burnt lime are boiled for 5 to io hours. The reaction mass is freed from excess nitrobenzene by steam distillation, the residue is washed with water and dried. It consists for the most part of benzanthrone-2-aldehyde, which z. B. can be cleaned by Uml, -xistallisiert from organic solvents and, if desired, converted into the corresponding carboxylic acid.
Verwendet man statt Kalk Magnesia, Soda, entwässertes Natriumacetat oder Bariumsuperoxyd, so gelangt man zum gleichen Produkt. An Stelle von Nitrobenzol kann man auch o-Nitrotoluol oder o-Nitrochlorbenzol verwenden.If you use magnesia, soda or dehydrated sodium acetate instead of lime or barium peroxide, one arrives at the same product. Instead of nitrobenzene you can also use o-nitrotoluene or o-nitrochlorobenzene.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE576176T | 1930-10-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE576176C true DE576176C (en) | 1933-05-08 |
Family
ID=6569897
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1930576176D Expired DE576176C (en) | 1930-10-29 | 1930-10-29 | Process for the production of oxidation products of the benzanthrone series |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE576176C (en) |
-
1930
- 1930-10-29 DE DE1930576176D patent/DE576176C/en not_active Expired
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