DE174238C - - Google Patents
Info
- Publication number
- DE174238C DE174238C DENDAT174238D DE174238DA DE174238C DE 174238 C DE174238 C DE 174238C DE NDAT174238 D DENDAT174238 D DE NDAT174238D DE 174238D A DE174238D A DE 174238DA DE 174238 C DE174238 C DE 174238C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- products
- anthracene
- reaction
- hydrocarbons
- 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.)
- Active
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- 150000002430 hydrocarbons Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 4
- 150000001785 cerium compounds Chemical class 0.000 claims description 3
- 239000003929 acidic solution Substances 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- 230000001590 oxidative Effects 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000875 corresponding Effects 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 description 2
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 2
- OFJATJUUUCAKMK-UHFFFAOYSA-N Cerium(IV) oxide Chemical compound [O-2]=[Ce+4]=[O-2] OFJATJUUUCAKMK-UHFFFAOYSA-N 0.000 description 2
- VNLFDHDLTYHIKF-UHFFFAOYSA-N anthracene-1,2-disulfonic acid Chemical compound C1=CC=CC2=CC3=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C3C=C21 VNLFDHDLTYHIKF-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-Chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-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
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 1
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-Nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N Anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- 210000004940 Nucleus Anatomy 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 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 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000005338 nitrobenzoic acids Chemical class 0.000 description 1
- SLAMLWHELXOEJZ-UHFFFAOYSA-N o-Nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Description
KAISERLICHES A IMPERIAL A
PATENTAMT..PATENT OFFICE ..
PATENTSCHRIFTPATENT LETTERING
- JVl 174238 KLASSE 12 o. GRUPPE- JVl 174238 CLASS 12 or GROUP
Zusatz zum Patente 158609 vom 18. Februar 1902.Addendum to patent 158609 of February 18, 1902.
Patentiert im Deutschen Reiche vom 4. Juni 1903 ab. Längste Dauer: 17. Februar 1917.Patented in the German Empire on June 4, 1903. Longest duration: February 17, 1917.
Durch das Patent 158609 ist ein Verfahren geschützt, nach, welchem sich aromatische Kohlenwasserstoffe mit Hilfe von Cerverbindungen vorteilhaft oxydieren lassen. Bei weiterer Ausarbeitung dieses Verfahrens hat sich nun gezeigt, daß danach auch Kohlenwasserstoffgruppen in substituierten Kohlen-A process is protected by patent 158609, according to which aromatic Let hydrocarbons oxidize advantageously with the help of cerium compounds. at Further elaboration of this process has now shown that then also hydrocarbon groups in substituted carbon
: Wasserstoffen oxydiert werden können. Man gelangt auf diese Weise zu den entsprechenden substituierten Oxydationsprodukten.: Hydrogen can be oxidized. Man This leads to the corresponding substituted oxidation products.
Daß sich auch Kohlenwasserstoffreste von im Kern substituierten Kohlenwasserstoffen mit Cerverbindungen erfolgreich- oxydieren lassen, war nicht vorauszusehen, da bekanntlieh durch Eintritt von Substituenten die Oxydation vielfach erschwert wird oder zur Bildung wertloser Produkte Veranlassung gibt.That there are also hydrocarbon residues of hydrocarbons substituted in the nucleus Can be successfully oxidized with cerium compounds could not be foreseen, as it is known the oxidation is often made more difficult by the entry of substituents or for Creation of worthless products.
Die Ausführung des Verfahrens ist imThe execution of the procedure is in
ao übrigen ähnlich wie im Hauptpatent beschrieben. . ao other similar to that described in the main patent. .
i. Um o-Chlortoluol zu o-Chlorbenzaldehyd zu oxydieren, bringt man beispielsweise in ein Gefäß mit Rührwerk Schwefelsäure von 60 bis 65 Prozent und pro Liter Schwefelsäure etwa 40 g o-Chlortoluol. Man erwärmt auf etwa 500UmI trägt fein gepulvertes technisches Cerdioxyd (erhalten durch Glühen der bei der Glühstrumpffabrikation abfallenden cerreichen Nebenprodukte) in kleinen Portionen derart ein, daß immer lebhafte Entfärbung des Cerdioxyds stattfindet. Dabei steigert man die Temperatur langsam bis etwa 900. Es bildet sich schließlich eine weiße breiige Masse aus Cerosulfat, aus weir eher neben unverändertem Ausgangsmaterial die Reaktionsprodukte ο - Chlorbenzaldehyd und geringe Mengen o-Chlorbenzoesäure in bekannter Weise gewonnen werden. Die Ausbeute beträgt etwa 66 Prozent der Theorie.i. In order to oxidize o-chlorotoluene to o-chlorobenzaldehyde, for example, a vessel with a stirrer is charged with sulfuric acid of 60 to 65 percent and about 40 g of o-chlorotoluene per liter of sulfuric acid. The mixture is heated to about 50 0 UmI carries finely powdered technical Cerdioxyd (obtained by annealing the falling in the Glühstrumpffabrikation cerreichen by-products) in small portions in such a that more vivid decolorization takes place of the Cerdioxyds. The temperature is slowly increased to about 90 ° . Finally, a white pulpy mass of cerosulphate forms, from which the reaction products ο-chlorobenzaldehyde and small amounts of o-chlorobenzoic acid are obtained in a known manner in addition to unchanged starting material. The yield is about 66 percent of theory.
Ähnlich wie o-Chlortoluol läßt sich auch o- und p-Nitrotoluol oxydieren, doch verläuft die Reaktion hierbei weniger glatt und führt leicht zu den entsprechenden Nitrobenzoesäuren. Man verwendet beispielsweise Schwefelsäure von 60 bis 70 Prozent und trägt das mehlfeine Cerdioxyd bei etwa 80 bis 85 ° unter kräftigem Rühren ein. Die Reaktionsprodukte Nitrobenzoesäure neben, den entsprechenden Aldehyden werden in üblicher Weise isoliert.Similar to o-chlorotoluene, o- and p-nitrotoluene can also be oxidized, but it takes place the reaction here is less smooth and easily leads to the corresponding nitrobenzoic acids. For example, 60 to 70 percent sulfuric acid is used and ceria, as fine as flour, is around 80 up to 85 ° with vigorous stirring. The reaction products nitrobenzoic acid in addition to, the corresponding aldehydes are isolated in the customary manner.
2. In eine schwefelsaure Lösung von Anthracendisulfosäure (Gemenge aus et- und ß-Anthracendisulfosäure, erhalten durch Sulfur ierung; von Anthracen) trägt man die für2. In a sulfuric acid solution of Anthracene disulphonic acid (mixture of et- and ß-anthracene disulphonic acid, obtained from Sulfur ation; of anthracene) one carries the for
die Anthrachinonsulfosäure berechnete Menge Cerisulfat ein. Es findet sofort und bei gewöhnlicher Temperatur Oxydation statt. Man erkennt das Ende der Reaktion daran, daß eine Probe beim* Verdünnen die den Anthracendisulfosäuren eigentümliche Reaktion nicht mehr zeigt. Die erhaltenen Anthrachinonsulfosäuren werden in bekannter Weise auf Alizarinfarbstoffe verarbeitet. the anthraquinone sulfonic acid calculated amount of cerium sulfate. Oxidation takes place immediately and at ordinary temperature. The end of the reaction can be recognized by the fact that a sample no longer shows the reaction peculiar to anthracene disulphonic acids when diluted. The anthraquinone sulfonic acids obtained are processed into alizarin dyes in a known manner.
Claims (1)
Abänderung des durch Patent 158609 geschützten Verfahrens, darin bestehend, daß man an Stelle der dort verwendeten Kohlenwasserstoffe hier deren Kernsubstitutionsprodukte mit Cerverbindungen in saurer Lösung behandelt, zum Zweck, nicht substituierte Kohlenwasserstoff feste zu oxydieren.Patent claim:
Modification of the process protected by patent 158609, which consists in treating the core substitution products with cerium compounds in acidic solution instead of the hydrocarbons used there, for the purpose of oxidizing unsubstituted hydrocarbons solids.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE174238C true DE174238C (en) |
Family
ID=438990
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT174238D Active DE174238C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE174238C (en) |
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0
- DE DENDAT174238D patent/DE174238C/de active Active
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