DE497808C - Process for the preparation of C-alkylated phenols - Google Patents
Process for the preparation of C-alkylated phenolsInfo
- Publication number
- DE497808C DE497808C DESCH86145D DESC086145D DE497808C DE 497808 C DE497808 C DE 497808C DE SCH86145 D DESCH86145 D DE SCH86145D DE SC086145 D DESC086145 D DE SC086145D DE 497808 C DE497808 C DE 497808C
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- preparation
- alkylated phenols
- hydrogenation
- reaction
- 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
- 238000000034 method Methods 0.000 title claims description 6
- 150000002989 phenols Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 238000005984 hydrogenation reaction Methods 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 4
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 2
- 239000005844 Thymol Substances 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229960000790 thymol Drugs 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
- C07C37/52—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms by splitting polyaromatic compounds, e.g. polyphenolalkanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung C-alkylierter Phenole In den Patenten 467 640 und 479 352 ist ein Verfahren zur Darstellung C-alkylierter Phenole beschrieben, das in der Behandlung von Diphenyhnethanderivaten mit Wasserstoff bei Gegenwart von Katalysatoren besteht.Method for Preparing C-Alkylated Phenols In Patents 467 640 and 479 352 describes a process for the preparation of C-alkylated phenols, that in the treatment of diphenyhnethane derivatives with hydrogen in the presence consists of catalysts.
Dieses Verfahren der spaltenden Hydrierung kann wesentlich verbessert und jede Kernhydrierung vermieden werden, wenn man den Wasserstoff verdünnt, sei es mit Wasserdampf, sei es mit einem indifferenten Gas, wie beispielsweise Stickstoff. Zwecks Erreichung größerer Reaktionsgeschwindigkeiten kann man dabei auf höhere Temperaturen gehen, ohne daß Kernhydrierung eintritt. Als Katalysator kann beispielsweise ein nicht vorreduzierter Katalysator verwendet werden, der als Carbonat oder als Hydroxyd gefällt wurde. Solche Katalysatoren werden im Autoklaven unter Wasserstoffdruck unter Bildung von Wasser in ihre katalytisch wirksame Form übergeführt. Bei einer Reaktionstemperatur von xgo ° bis Zoo ° und einem Arbeitsdruck von 25 Atm. ist der im Gasraum des Autoklaven befindliche Wasserstoff etwa zur Hälfte mit Wasserdampf verdünnt. Die Hydrierung verläuft quantitativ und ohne jede Kernhydrierung. Beispiel x Di-(4-oxyphenyl )dimethylmethan wird mit 50/, seines Gewichts eines aus Carbonaten oder Hydroxyden katalytisch wirksamer Metalle bestehenden Hydrierungskatalysators bei etwa Zoo ° mit Wasserstoff unter Druck behandelt. Nach Aufnahme der zur spaltenden Hydrierung notwendigen Wasserstoffmenge bleibt die Reaktion stehen. Durch Fraktionierung erhält man in theoretischer Ausbeute p-Isopropylphenol neben Phenol. Beispiel 2 Di-(4-methyl-6-oxyphenyl-)dimethylmethan (vgl. Patent 494 5o8) wird wie in Beispiel = behandelt. Der Reaktionsverlauf ist derselbe. Durch Fraktionierung lassen sich die in theoretischer Ausbeute entstandenen Spaltstücke m-Kresol und Thymol gewinnen. Beispiel 3 Di- (q.- methyl-6-oxyplienyl-) dimethylmethan wird mit etwa 304 seines Gewichts eines vorreduzierten Hydrierungskatalysators in einem Autoklaven bei etwa Zoo ° mit Wasserstoff unter Druck behandelt, nachdem vorher das Reaktionsgefäß zu etwa i/s bis 1/2 seines Arbeitsdruckes mit Stickstoff aufgefüllt wurde. Die Reaktion verläuft wie in Beispiel x und 2. Die Ausbeuten an Thymol und m-Kresol sind theoretisch.This splitting hydrogenation process can be significantly improved and any nuclear hydrogenation can be avoided by diluting the hydrogen it with water vapor, be it with an inert gas such as nitrogen. In order to achieve greater reaction rates, one can use higher Temperatures go without nuclear hydrogenation occurring. As a catalyst, for example a non-prereduced catalyst can be used as a carbonate or as Hydroxyd was precipitated. Such catalysts are in the autoclave under hydrogen pressure converted into their catalytically active form with the formation of water. At a Reaction temperature from xgo ° to Zoo ° and a working pressure of 25 atm. is the About half of the hydrogen in the gas space of the autoclave is with water vapor diluted. The hydrogenation proceeds quantitatively and without any nuclear hydrogenation. example x Di- (4-oxyphenyl) dimethylmethane is 50 /, its weight one from carbonates or hydroxides of catalytically active metals existing hydrogenation catalyst treated with hydrogen under pressure at about Zoo °. After the inclusion of the divisive The amount of hydrogen required for hydrogenation stops the reaction. By fractionation p-Isopropylphenol is obtained in addition to phenol in theoretical yield. Example 2 Di- (4-methyl-6-oxyphenyl-) dimethylmethane (cf. Patent 494 508) is as in Example = treated. The course of the reaction is the same. Fractionation can be used win the split pieces m-cresol and thymol formed in theoretical yield. example 3 Di- (q.-methyl-6-oxyplienyl-) dimethylmethane is about 304% of its weight of a pre-reduced hydrogenation catalyst in an autoclave at about Zoo ° treated with hydrogen under pressure after previously opening the reaction vessel to about i / s to 1/2 of its working pressure was filled with nitrogen. The reaction proceeds as in example x and 2. The yields of thymol and m-cresol are theoretical.
In ähnlicher Weise verfährt man, wenn man von den in dem Patent 479 352 erwähnten Diphenyhuethanderivaten ausgeht.A similar procedure is followed when one proceeds from those described in the '479 patent 352 mentioned diphenyhuethane derivatives goes out.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH86145D DE497808C (en) | 1928-04-17 | 1928-04-17 | Process for the preparation of C-alkylated phenols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH86145D DE497808C (en) | 1928-04-17 | 1928-04-17 | Process for the preparation of C-alkylated phenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE497808C true DE497808C (en) | 1931-01-22 |
Family
ID=7443399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DESCH86145D Expired DE497808C (en) | 1928-04-17 | 1928-04-17 | Process for the preparation of C-alkylated phenols |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE497808C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1115264B (en) * | 1957-05-08 | 1961-10-19 | Bataafsche Petroleum | Process for the nucleus alkylation of phenols |
| DE1119293B (en) * | 1957-05-08 | 1961-12-14 | Bataafsche Petroleum | Process for the preparation of 2,4,6-trialkylphenols |
-
1928
- 1928-04-17 DE DESCH86145D patent/DE497808C/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1115264B (en) * | 1957-05-08 | 1961-10-19 | Bataafsche Petroleum | Process for the nucleus alkylation of phenols |
| DE1119293B (en) * | 1957-05-08 | 1961-12-14 | Bataafsche Petroleum | Process for the preparation of 2,4,6-trialkylphenols |
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