DE976478C - Process for the production of phenols by incomplete oxidation of benzene derivatives - Google Patents
Process for the production of phenols by incomplete oxidation of benzene derivativesInfo
- Publication number
- DE976478C DE976478C DE1949D0025248 DED0025248D DE976478C DE 976478 C DE976478 C DE 976478C DE 1949D0025248 DE1949D0025248 DE 1949D0025248 DE D0025248 D DED0025248 D DE D0025248D DE 976478 C DE976478 C DE 976478C
- Authority
- DE
- Germany
- Prior art keywords
- oxidation
- alkylbenzene
- peroxides
- phenols
- benzene derivatives
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/04—Phenol
-
- 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
- C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
Description
(WiGBl. S. 175)(WiGBl. P. 175)
AUSGEGEBEN AM 26. SEPTEMBER 1963ISSUED SEPTEMBER 26, 1963
D 25248 IVb/12 qD 25248 IVb / 12 q
von Benzolderivatenof benzene derivatives
Die Erfindung bezieht sich auf eine Abänderung des Verfahrens gemäß Patent 966 684 zur Herstellung von Phenolen durch unvollständige Oxydation von Benzolderivaten, die durch eine oder mehrere Alkylgruppen substituiert sind, von denen mindestens eine ein tertiäres Kohlenstoffatom in α-Stellung zum Benzolring hat, z. B. Isopropylbenzol, mit molekularem Sauerstoff in der flüssigen Phase, wobei die Oxydation nur so weit durchgeführt wird, daß die erhaltene Oxydationsmischung 25 bis 50% Alkylbenzolperoxyde enthält, und Zersetzung der so gewonnenen Alkylbenzolperoxyde bei 40 bisThe invention relates to a modification of the method according to patent 966,684 for manufacture of phenols by incomplete oxidation of benzene derivatives by one or more Alkyl groups are substituted, of which at least one has a tertiary carbon atom in the α-position has to the benzene ring, e.g. B. Isopropylbenzene, with molecular oxygen in the liquid phase, where the oxidation is only carried out so far that the oxidation mixture obtained is 25 to 50% Contains alkylbenzene peroxides, and decomposition of the alkylbenzene peroxides obtained in this way at 40 to
8o° C mit einer wäßrigen Schwefelsäure von 20 bis 70%.80 ° C with an aqueous sulfuric acid of 20 to 70%.
Vorliegende Erfindung beruht, wie die Erfindung des Hauptpatentes, auf der Regel, daß die Oxydation mit molekularem Sauerstoff nur so weit durchgeführt wird, daß die erhaltene flüssige Reaktionsmischung noch einen wesentlichen Anteil an unverändertem Alkylbenzol enthält.The present invention is based, like the invention of the main patent, on the rule that oxidation is carried out with molecular oxygen only so far that the liquid reaction mixture obtained still has a substantial proportion of unchanged Contains alkylbenzene.
Es wurde gefunden, daß man das Verfahren des Hauptpatentes in der oben angegebenen Ausführungsform auch mit Erfolg durchführen kann, wenn man vor der Zersetzung der Alkylbenzol-It has been found that the process of the main patent in the embodiment given above can also be carried out successfully if, before the decomposition of the alkylbenzene
309 692/8309 692/8
peroxyde bei 40 bis 8o° C mit einer wäßrigen Schwefelsäure von 20 bis 70% die Oxydation so weit durchführt, daß die erhaltene Oxydationsmischung weniger als 25 % oder mehr als 50% Alkylbenzolperoxyde enthält, jedoch noch eine Menge an Alkylbenzol, die ausreicht, um die entstandenen Peroxyde in Lösung zu halten.peroxyde at 40 to 80 ° C with an aqueous sulfuric acid of 20 to 70% the oxidation so carries out far that the oxidation mixture obtained is less than 25% or more than 50% Alkylbenzene peroxides, however, still contain an amount of alkylbenzene that is sufficient to produce the resultant Keep peroxides in solution.
Die Mindestkonzentration des Peroxyds in dem nicht umgesetzten Kohlenwasserstoff wird durch wirtschaftliche Überlegungen bestimmt, man wird jedoch zweckmäßig nicht unter 9,5 %> gehen.The minimum concentration of the peroxide in the unreacted hydrocarbon is determined by economic considerations determine, but it is expedient not to go below 9.5%> walk.
Die Höchstkonzentration hängt sowohl von wirtschaftlichen als auch von Sicherheitserwägungen ab, da zu hohe Konzentrationen an Peroxyd zu Explosionen Anlaß geben können. Man muß aber mindestens Mengen von Alkylbenzolen verwenden, die die entsprechenden Alkylbenzolhydroperoxyde und Alkylbenzolperoxyde lösen.The maximum concentration depends on both economic and safety considerations as concentrations of peroxide that are too high can lead to explosions. But you have to use at least amounts of alkylbenzenes that correspond to the corresponding alkylbenzene hydroperoxides and dissolve alkylbenzene peroxides.
Im übrigen gelten die Erläuterungen in der Be-Schreibung des Hauptpatentes sinngemäß.Otherwise, the explanations in the description of the main patent apply accordingly.
160 ecm einer Lösung von 16,7% Isopropylbenzolperoxyd in Isopropylbenzol (die aus der Oxydation von Isopropylbenzol stammte) wurde mit 160 ecm einer 55%igen wäßrigen Schwefelsäure vermischt und die Mischung unter kräftigem Rühren auf 6o° C erhitzt. Nach 20 Minuten waren 94,3 fl/o und nach 30 Minuten 98,2% des ursprünglieh vorhandenen Peroxyds zersetzt. Während der Reaktion und kurze Zeit danach wurde ein Strom von Stickstoff durch die Flüssigkeit geleitet, um das entstandene Aceton zu entfernen. Die Ausbeute an dem erhaltenen Phenol betrug 91,3%, an Aceton 86,5 »/0.160 ecm of a solution of 16.7% isopropylbenzene peroxide in isopropylbenzene (which originated from the oxidation of isopropylbenzene) was mixed with 160 ecm of 55% strength aqueous sulfuric acid and the mixture was heated to 60 ° C. with vigorous stirring. After 20 minutes 94.3 fl / o and after 30 minutes 98.2% of the originally present peroxide had decomposed. During the reaction and for a short time thereafter, a stream of nitrogen was passed through the liquid to remove the acetone formed. The yield of the phenol obtained was 91.3%, that of acetone 86.5%.
Claims (1)
Berichte der Deutschen Chemischen Gesellschaft, Bd. 77, 1944, S. 257 bis 264.Considered publications:
Reports of the German Chemical Society, Vol. 77, 1944, pp. 257 to 264.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB419347A GB626095A (en) | 1947-02-13 | 1947-02-13 | Manufacture of phenols |
Publications (1)
Publication Number | Publication Date |
---|---|
DE976478C true DE976478C (en) | 1963-09-26 |
Family
ID=9772465
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT976951D Expired DE976951C (en) | 1947-02-13 | Process for the production of phenols by incomplete oxidation of benzene derivatives | |
DEP32198A Expired DE966684C (en) | 1947-02-13 | 1949-01-22 | Process for the production of phenols by incomplete oxidation of benzene derivatives |
DE1949D0025248 Expired DE976478C (en) | 1947-02-13 | 1949-01-22 | Process for the production of phenols by incomplete oxidation of benzene derivatives |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT976951D Expired DE976951C (en) | 1947-02-13 | Process for the production of phenols by incomplete oxidation of benzene derivatives | |
DEP32198A Expired DE966684C (en) | 1947-02-13 | 1949-01-22 | Process for the production of phenols by incomplete oxidation of benzene derivatives |
Country Status (6)
Country | Link |
---|---|
BE (1) | BE480371A (en) |
DE (3) | DE966684C (en) |
FR (1) | FR961022A (en) |
GB (2) | GB626095A (en) |
IT (2) | IT458013A (en) |
NL (2) | NL77380C (en) |
Families Citing this family (39)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2734085A (en) * | 1956-02-07 | Removal of salts from acetone-phenol mixtures | ||
DE945451C (en) * | 1948-06-05 | 1956-07-12 | Distillers Co Yeast Ltd | Process for the production of phenols |
US2776322A (en) * | 1948-10-30 | 1957-01-01 | Hercules Powder Co Ltd | Manufacture of beta-naphthol |
BE495279A (en) * | 1949-04-29 | |||
US2750424A (en) * | 1949-06-08 | 1956-06-12 | Hercules Powder Co Ltd | Manufacture of cumylphenol |
US2626281A (en) * | 1949-08-23 | 1953-01-20 | Allied Chem & Dye Corp | Decomposition of aralkyl alphahydroperoxides |
IT486308A (en) * | 1949-12-30 | |||
US2661375A (en) * | 1950-02-07 | 1953-12-01 | Hercules Powder Co Ltd | Production of phenols and acyclic aldehydes |
US2668180A (en) * | 1950-07-01 | 1954-02-02 | Hercules Powder Co Ltd | Preparation of aryldialkyl peroxides |
DE923723C (en) * | 1950-10-09 | 1955-02-21 | Rhone Poulenc Sa | Process for the simultaneous production of phenol and acetaldehyde |
IT482379A (en) * | 1950-10-31 | |||
US2757209A (en) * | 1951-04-26 | 1956-07-31 | Allied Chem & Dye Corp | Recovery of phenol and alphamethylstyrene from cumene oxidation reaction mixtures |
NL80287C (en) * | 1951-04-28 | |||
DE1085536B (en) * | 1951-05-17 | 1960-07-21 | Bataafsche Petroleum | Process for the decomposition of aromatic hydroperoxides |
US2761877A (en) * | 1951-05-17 | 1956-09-04 | Rhone Poulenc Sa | Production of phenols and carbonyl compounds |
DE1016270B (en) * | 1951-05-17 | 1957-09-26 | Rhone Poulenc Sa | Process for the simultaneous production of phenols and ketones or aldehydes |
US2737527A (en) * | 1951-07-09 | 1956-03-06 | Rhone Poulenc Sa | Production of phenols and carbonyl compounds |
LU31582A1 (en) * | 1951-07-18 | |||
US2669588A (en) * | 1951-10-17 | 1954-02-16 | Shell Dev | Production of bis (hydroxyaryl) substituted compounds |
DE976125C (en) * | 1951-11-25 | 1963-03-14 | Ruetgerswerke Ag | Process for the distillative separation of cumene-phenol mixtures originating from the cumene hydroperoxide decomposition and freed from acetone |
US2671809A (en) * | 1952-03-04 | 1954-03-09 | Shell Dev | Controlled decomposition of aralkyl hydroperoxides |
US2802884A (en) * | 1952-05-31 | 1957-08-13 | Koppers Co Inc | Alkylation-dealkylation catalysts |
DE1110174B (en) * | 1952-06-26 | 1961-07-06 | California Research Corp | Process for the production of hydrocarbon-free phenol |
DE1159467B (en) * | 1952-07-01 | 1963-12-19 | Ruetgerswerke Ag | Process for the separation of mixtures of alkyl aromatic hydrocarbons and phenols by distillation |
DE1159468B (en) * | 1952-11-05 | 1963-12-19 | Ruetgerswerke Ag | Process for separating cumene and phenol by distillation from a mixture which is obtained in the cleavage of cumene hydroperoxide in the presence of acids and from which the acetone has been separated off by distillation |
DE944013C (en) * | 1953-05-09 | 1956-06-07 | Bergwerksgesellschaft Hibernia | Process for splitting organic hydroperoxides |
US2950320A (en) * | 1953-05-27 | 1960-08-23 | Hercules Powder Co Ltd | 5-benzoyl pentanol-1 |
DE1091121B (en) * | 1953-07-30 | 1960-10-20 | California Research Corp | Process for the production of phenol and acetone by splitting cumene hydroperoxide |
DE971921C (en) * | 1954-06-23 | 1959-04-16 | Rhone Poulenc Sa | Process for the separation of the cleavage products of cumene hydroperoxide by distillation |
US2911387A (en) * | 1954-07-06 | 1959-11-03 | Hercules Powder Co Ltd | Polymer phenol hydroperoxides |
US2957921A (en) * | 1958-03-31 | 1960-10-25 | California Research Corp | Processes for separating hydroperoxides into phenol and other products |
DE1112527B (en) * | 1959-03-28 | 1961-08-10 | Phenolchemie Ges Mit Beschraen | Process for cleaving hydroperoxides of alkyl aromatic hydrocarbons |
NL241648A (en) * | 1959-07-24 | |||
DE1219035B (en) * | 1961-04-26 | 1966-06-16 | Inst Gorjutschich Iskopajemych | Process for working up the distillation residues which have been obtained in the production of phenol by splitting cumene hydroperoxide |
CA1128549A (en) * | 1978-12-14 | 1982-07-27 | Lewis B. Young | Production of 3-methylphenol |
US5254751A (en) * | 1992-09-14 | 1993-10-19 | General Electric Company | Method for the decomposition of cumene hydroperoxide by acidic catalyst to phenol and acetone |
PL181496B1 (en) * | 1996-03-20 | 2001-07-31 | Politechnika Slaska Im Wincent | Method of obtaining beta-naphtole |
CN1938250A (en) | 2004-03-31 | 2007-03-28 | 通用电气公司 | Process for producing phenol |
CN108689807B (en) * | 2018-06-25 | 2021-04-02 | 宁夏金海新科化工有限公司 | Method for preparing cresol by using toluene and oleum |
-
0
- IT IT448512D patent/IT448512A/it unknown
- NL NL666603782A patent/NL138783B/en unknown
- DE DENDAT976951D patent/DE976951C/en not_active Expired
- BE BE480371D patent/BE480371A/xx unknown
- FR FR961022D patent/FR961022A/fr not_active Expired
- IT IT458013D patent/IT458013A/it unknown
- NL NL77380D patent/NL77380C/xx active
-
1947
- 1947-02-13 GB GB419347A patent/GB626095A/en not_active Expired
- 1947-08-21 GB GB2320947A patent/GB629429A/en not_active Expired
-
1949
- 1949-01-22 DE DEP32198A patent/DE966684C/en not_active Expired
- 1949-01-22 DE DE1949D0025248 patent/DE976478C/en not_active Expired
Non-Patent Citations (1)
Title |
---|
None * |
Also Published As
Publication number | Publication date |
---|---|
BE480371A (en) | |
GB629429A (en) | 1949-09-20 |
IT458013A (en) | |
GB626095A (en) | 1949-07-08 |
DE966684C (en) | 1957-09-05 |
NL138783B (en) | |
NL77380C (en) | |
IT448512A (en) | |
DE976951C (en) | 1964-08-06 |
FR961022A (en) | 1950-04-28 |
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