DE2345911A1 - PROCESS FOR ISOMERIZATION OF PHENETOL - Google Patents
PROCESS FOR ISOMERIZATION OF PHENETOLInfo
- Publication number
- DE2345911A1 DE2345911A1 DE19732345911 DE2345911A DE2345911A1 DE 2345911 A1 DE2345911 A1 DE 2345911A1 DE 19732345911 DE19732345911 DE 19732345911 DE 2345911 A DE2345911 A DE 2345911A DE 2345911 A1 DE2345911 A1 DE 2345911A1
- Authority
- DE
- Germany
- Prior art keywords
- phenetol
- ethylphenol
- isomerization
- weight
- phenol
- 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.)
- Granted
Links
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
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
Description
RÜTGEREWEKKERÜTGEREWEKKE
Prankfurt am MainPrankfurt am Main
Pat-575-RPat-575-R
PatentanmeldungPatent application
Die im folgenden beschriebene Erfindung betrifft ein Verfahren zur Isomerisierung von Phenetol (Phenyläthyläther) in der Gasphase an Aluminiumoxidkatalysatoren·The invention described below relates to a process for the isomerization of phenetol (phenylethyl ether) in the gas phase on aluminum oxide catalysts
Es ist bekannt, daß Phenylalkyläther bei höheren Temperaturen in der Gasphase an Aluminiumoxidkatalysatoren zu C-Alkylphenolen umgesetzt werden können·It is known that phenylalkyl ethers can be converted to C-alkylphenols at higher temperatures in the gas phase over aluminum oxide catalysts.
In der DOS 1 793 l86 vom 13.8.68/28.10.71 wird z.B. die Isomerisierung eines Phenol-Phenetol-Gemisches zu o-Äthylphenol beschrieben,welche an einem Aluminiumoxidkatalysator bei 340 bis 44O°C, vorzugsweise bei 370 bis 38O0C, durchgeführt wird. Hierbei kann jedoch nur weniger als die Hälfte des eingesetzten Phenetols zu o-Äthylphenol umgesetzt werden. Mehr als die Hälfte des eingesetzten Phenetols geht durch Entalkylierung zu Phenol verloren. Darüber hinaus entstehen Nebenprodukte, die die Ausbeute an o-Äthylphenol weiter vermindern.In DOS 1793 l86 from 13.08.68 / 10.28.71 example is the isomerization of a phenol-phenetole mixture described to o-ethyl phenol, which is performed on an alumina catalyst at 340 to 44O ° C, preferably at 370 to 38O 0 C will. In this case, however, only less than half of the phenetol used can be converted to o-ethylphenol. More than half of the phenetol used is lost through dealkylation to phenol. In addition, by-products are formed which further reduce the yield of o-ethylphenol.
Überraschenderweise wurde nun gefunden, daß das Phenetol an einem Aluminiumoxidkatalysator bei Temperaturen von 270 bis 32O°C, vorzugsweise von 290 bis 3l0°C, rasch und ohne Entalkylierung oder wesentliche andere Nebenreaktionen fast vollständig zu o-Äthylphenol isomerisiert wird. Wie in der erwähnten Offenlegungsschrift kann das Phenetol hierbei auch im Gemisch mit Phenol, o-Äthylphenol und/oder anderen Alkylphenolen zur Reaktion gebracht wer den. Der Phenetolgehalt dieser Gemische ist hierbei in weiten Grenzen variierbar· Surprisingly, it has now been found that the phenetol is almost completely isomerized to o-ethylphenol over an aluminum oxide catalyst at temperatures from 270 to 320 ° C., preferably from 290 to 30 ° C., rapidly and without dealkylation or significant other side reactions. As in the aforementioned laid -open specification, the phenetol can also be reacted in a mixture with phenol, o-ethylphenol and / or other alkylphenols . The phenetol content of these mixtures can be varied within wide limits
509813/1131509813/1131
.2-.2-
Der Vorteil des Verfahrens besteht z.b. darin, daß das bei der C-Äthylierung von Phenol häufig als Nebenprodukt anfallende Phenetol nicht mehr umständlich von unumgesetzten Phenol abgetrennt werden muß, sondern zusammen mit dem Phenol dem erfindungsgemäßen Vorgehen unterworfen werden kann, und wobei dann in hoher Ausbeute das gewünschte o-Äthylphenol gebildet wird.The advantage of the process is, for example , that the phenetol, which is often obtained as a by-product in the C-ethylation of phenol, no longer has to be laboriously separated from unreacted phenol, but can be subjected to the procedure according to the invention together with the phenol, and then in high yield the desired o-ethylphenol is formed.
Ein weitererVorteil besteht in der direkten Gewinnung von o-Äthyl· phenolfraktionen» die neben Phenol und o-Äthylphenol nut geringe Mengen anderer Nebenprodukte enthalten·Another advantage is the direct production of o-ethyl phenol fractions »which in addition to phenol and o-ethylphenol only contain small amounts of other by-products ·
Das folgende Beispiel erläutert die, Erfindung:
Ein Gemisch, enthaltend The following example explains the invention:
A mixture containing
Phenol 64,8 Gew.-%Phenol 64.8% by weight
Phenetol 17*2 Gew.-%Phenetol 17 * 2% by weight
o-Äthylphenol 15,5 Gew.-%o-ethylphenol 15.5% by weight
m+p-Äthylphenol 1,0 Gew,-%m + p-ethylphenol 1.0% by weight
2.6-Diäthylphenol 1,5 Gew,-%2.6-diethylphenol 1.5% by weight
übrige Phenole 2,0 Gew,-%other phenols 2.0% by weight
wird bei Atmosphärendruck durch ein Reaktionsrohr geführt, welches den jf -Aluminiumoxid-Katalysator, der mit 'einer geringen Menge aktiviert ist, enthält· Bei einer Heaktionsteraperatur von 300 C (hot spot bei 3060C) wird ein Reaktionsprodukt folgender Zusammensetzung erhalten:is conducted at atmospheric pressure through a reaction tube which the jf-alumina catalyst which is activated with 'a small amount, · contains In a Heaktionsteraperatur 300 C (hot spot at 306 0 C) is obtained a reaction product having the following composition:
Phenol . 64,7 Gew.-%Phenol. 64.7% by weight
Phenetol 0,1 Gew.-%Phenetol 0.1% by weight
o-Xthylphenol 27,7. Gew.-%o-ethylphenol 27.7. Wt%
m+p-Äthylphenol 1,9 Gew.«-%m + p-ethylphenol 1.9% by weight
2.6-Diäthylphenol 3»4 Gew.-%2.6-diethylphenol 3 »4% by weight
übrige Phenole 2,2 Gew.-%other phenols 2.2% by weight
Hieraus ist zu ersehen, daß das im Auegangsgemisch vorhandene Phenetol fast quantitativ umgesetzt wird und mit hoher Selektivität O-Äthylphenol ergibt·From this it can be seen that the phenetol present in the initial mixture is converted almost quantitatively and results in O-ethylphenol with high selectivity
509813/1131 · 3 ·509813/1131 · 3 ·
Claims (1)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732345911 DE2345911C3 (en) | 1973-09-12 | Process for the isomerization of phenetol to o-ethylphenol | |
| GB3651574A GB1410586A (en) | 1973-09-12 | 1974-08-20 | Preparation of o-ethylphenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732345911 DE2345911C3 (en) | 1973-09-12 | Process for the isomerization of phenetol to o-ethylphenol |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2345911A1 true DE2345911A1 (en) | 1975-03-27 |
| DE2345911B2 DE2345911B2 (en) | 1976-05-20 |
| DE2345911C3 DE2345911C3 (en) | 1976-12-30 |
Family
ID=
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4447657A (en) * | 1982-11-10 | 1984-05-08 | Uop Inc. | Preparation of ortho-alkylated phenols |
| US4465871A (en) * | 1982-11-10 | 1984-08-14 | Uop Inc. | Preparation of 2-t-butyl-4-alkoxy- and 4-hydroxyphenols |
| US4538008A (en) * | 1982-11-10 | 1985-08-27 | Uop Inc. | Preparation of ortho-alkylated phenols |
| US4709102A (en) * | 1986-10-07 | 1987-11-24 | Celanese Corporation | Process for producing 2-lower alkyl phenols |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4447657A (en) * | 1982-11-10 | 1984-05-08 | Uop Inc. | Preparation of ortho-alkylated phenols |
| US4465871A (en) * | 1982-11-10 | 1984-08-14 | Uop Inc. | Preparation of 2-t-butyl-4-alkoxy- and 4-hydroxyphenols |
| US4538008A (en) * | 1982-11-10 | 1985-08-27 | Uop Inc. | Preparation of ortho-alkylated phenols |
| US4709102A (en) * | 1986-10-07 | 1987-11-24 | Celanese Corporation | Process for producing 2-lower alkyl phenols |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2345911B2 (en) | 1976-05-20 |
| GB1410586A (en) | 1975-10-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |