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 derivatives

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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
Application number
DE1949D0025248
Other languages
German (de)
Inventor
Basil Vivian Aller
Karl Heinrich Walter Turck
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Distillers Co Ltd
Original Assignee
Distillers Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Distillers Co Ltd filed Critical Distillers Co Ltd
Application granted granted Critical
Publication of DE976478C publication Critical patent/DE976478C/en
Expired legal-status Critical Current

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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.

Beispielexample

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)

PATENTANSPRUCH:PATENT CLAIM: Abänderung des Verfahrens 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 500/» Alkylbenzolperoxyde enthält, und Zersetzung der so gewonnenen Alkylbenzolperoxyde bei 40 bis 8o° C mit einer wäßrigen Schwefelsäure von 20 bis 70% nach Ansprüchen 3 bis 5 und 7 bis 12 des Patentes 966 684, dadurch gekennzeichnet, daß die Oxydation so weit durchgeführt wird, 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.Modification of the process for the preparation of phenols by incomplete oxidation of benzene derivatives which are substituted by one or more alkyl groups, at least one of which has a tertiary carbon atom in the α-position to the benzene ring, e.g. B. Isopropylbenzene, with molecular oxygen in the liquid phase, the oxidation is only carried out so far that the oxidation mixture obtained contains 25 to 50 0 / »alkylbenzene peroxides, and decomposition of the alkylbenzene peroxides obtained in this way at 40 to 80 ° C with an aqueous sulfuric acid from 20 to 70% according to claims 3 to 5 and 7 to 12 of patent 966 684, characterized in that the oxidation is carried out so far that the oxidation mixture obtained contains less than 25% or more than 50% alkylbenzene peroxides, but still a lot of alkylbenzene, which is sufficient to keep the resulting peroxides in solution. In Betracht gezogene Druckschriften:
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. © 309 692/8 9.63© 309 692/8 9.63
DE1949D0025248 1947-02-13 1949-01-22 Process for the production of phenols by incomplete oxidation of benzene derivatives Expired DE976478C (en)

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)

* Cited by examiner, † Cited by third party
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

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
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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