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DE1088485B - Process for the preparation of the peroxides of methylcyclohexanones - Google Patents

Process for the preparation of the peroxides of methylcyclohexanones

Info

Publication number
DE1088485B
DE1088485B DEM38901A DEM0038901A DE1088485B DE 1088485 B DE1088485 B DE 1088485B DE M38901 A DEM38901 A DE M38901A DE M0038901 A DEM0038901 A DE M0038901A DE 1088485 B DE1088485 B DE 1088485B
Authority
DE
Germany
Prior art keywords
peroxides
peroxide
methylcyclohexanones
hydrogen peroxide
preparation
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.)
Pending
Application number
DEM38901A
Other languages
German (de)
Inventor
Giampaolo Chiusoli
Francesco Minisci
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.)
Montedison SpA
Original Assignee
Montedison SpA
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 Montedison SpA filed Critical Montedison SpA
Publication of DE1088485B publication Critical patent/DE1088485B/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C409/00—Peroxy compounds
    • C07C409/20—Peroxy compounds the —O—O— group being bound to a carbon atom further substituted by singly—bound oxygen atoms
    • C07C409/22—Peroxy compounds the —O—O— group being bound to a carbon atom further substituted by singly—bound oxygen atoms having two —O—O— groups bound to the carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C407/00—Preparation of peroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung der Peroxyde der Methylcyclohexanone Die vorliegende Erfindung betrifft ein neuartiges Verfahren zur Herstellung der Peroxyde der Methylcyclohexanone. Process for the preparation of the peroxides of the methylcyclohexanones Die The present invention relates to a novel process for the preparation of the peroxides the methylcyclohexanones.

Organische Peroxyde haben unter anderem insofern Bedeutung, als sie geeignete Ausgangsstoffe für orga nische Synthesen darstellen. So kann man z. B. nach bekannten Verfahren Dekandicarbonsäure darstellen, wenn man von dem Peroxyd des Cyclohexanons ausgeht. Man erhält dieses Peroxyd, wenn man Cyclohexanon z. B. mit Wasserstoffperoxyd oxydiert. Organic peroxides are important, among other things, as they represent suitable starting materials for organic syntheses. So you can z. B. represent decanedicarboxylic acid according to known processes, if one of the peroxide of cyclohexanone runs out. This peroxide is obtained if you add cyclohexanone z. B. oxidized with hydrogen peroxide.

Dabei entstehen Peroxyde verschiedener Zusammensetzung, die leicht in Radikale zerlegt werden können, die sich ihrerseits zu der genannten Dicarbonsäure dimerisieren.This creates peroxides of various compositions, which are easy can be broken down into radicals, which in turn form the dicarboxylic acid mentioned dimerize.

Nach einer bekannten Arbeitsweise erhält man das Peroxyd von 2-Methylcyclohexanon, wenn man 2-Methylcyclohexanon mit 90'/obigem Wasserstoffperoxyd oxydiert. Diese Art der Herstellung besitzt aber den Nachteil, daß der Umgang mit so hochprozentigem Wasserstoffperoxyd besondere Vorsicht und Sorgfalt verlangt, ganz abgesehen von den Kosten bei Verwendung dieser teuren Substanz. Es bedeutet also einen beträchtlichen Vorteil, wenn es gelingt, das Peroxyd des 2-Methylcyclohexanons unter einfacheren Voraussetzungen, bei denen so hochprozentiges Wasserstoffperoxyd nicht mehr benötigt wird, herzustellen. According to a known procedure, the peroxide of 2-methylcyclohexanone is obtained, if 2-methylcyclohexanone is oxidized with 90 '/ above hydrogen peroxide. These However, the type of production has the disadvantage that dealing with such a high percentage Hydrogen peroxide requires special caution and care, not to mention the cost of using this expensive substance. So it means a considerable one Advantage, if it succeeds, the peroxide of 2-Methylcyclohexanons under simpler Conditions in which such a high percentage of hydrogen peroxide is no longer required will produce.

Es ist bekannt, zur Herstellung von Cyclohexanonperoxyd ätherische Wasserstoffperoxydlösungen zu verwenden, d. h. ein Reaktionsmittel, das wegen seiner Gefährlichkeit nur für Laboratoriums synthesen geeignet ist. Obendrein muß noch bedacht werden, daß der Äther durch Trocknen des Peroxyds zu beseitigen ist. Bei der neuen Arbeitsweise hingegen wird ein Wasser-Dioxan-Gemisch verwendet, das leicht und unmittelbar hergestellt werden kann. In dem Maße, wie sich das Peroxyd bildet, scheidet es sich als schwere Schicht ab, so daß das Reaktionsprodukt durch einfaches Waschen mit Wasser von Dioxan und einem etwaigen Was serstoffperoxydüberschuß leicht befreit werden kann. It is known essential for the production of cyclohexanone peroxide To use hydrogen peroxide solutions, d. H. a reactant that because of its Hazardousness is only suitable for laboratory syntheses. On top of that I still have to It must be remembered that the ether is to be removed by drying the peroxide. at the new procedure, however, a water-dioxane mixture is used, which easily and can be produced immediately. As the peroxide forms, it separates out as a heavy layer, so that the reaction product by simple Wash with water from dioxane and any excess hydrogen peroxide easily can be released.

Auch hat man schon Alkylcyclohexylperoxyde durch Verwendung von schwefelsauren, essigsäureanhydridhaltigen Wasserstoffperoxydgemischen hergestellt. Dieses Verfahren ist umständlich vor allem durch die Schwierigkeit der Abscheidung des Peroxyds aus dem Reaktionsgemisch. Alkylcyclohexyl peroxides have also been found by using sulfuric acids, hydrogen peroxide mixtures containing acetic anhydride. This method is cumbersome mainly due to the difficulty of separating the peroxide the reaction mixture.

Gemäß der Erfindung kann die Oxydation nun bereits mit 300/oigem Wasserstoffperoxyd ausgeführt werden, wenn man gleichzeitig in Dioxanlösung arbetet Beispiel 20 g 2-Methylcyclohexanon, 20 acm Dioxan und 17 ccm Wasserstoffperoxyd (30P/oig) werden bei 20° C gemischt. Die Temperatur erhöht sich auf 320 C. Nach t/2stündigem Stehen werden 0,5 ccm 1 n-H Cl zugefügt. According to the invention, the oxidation can now already with 300 / oigem Hydrogen peroxide can be carried out when working in a dioxane solution at the same time Example 20 g of 2-methylcyclohexanone, 20 acm of dioxane and 17 cc of hydrogen peroxide (30P / oig) are mixed at 20 ° C. The temperature rises to 320 C. After t / 2 hours standing, 0.5 ccm 1 n-H Cl are added.

Kurz darauf scheidet sich ein Öl ab, das dekantiert wird. Das Öl enthält 70O/ Peroxyd. Die Ausbeute beträgt 97,5 °/o.Shortly afterwards, an oil separates out, which is decanted. The oil contains 70O / peroxide. The yield is 97.5%.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung der Peroxyde der Methylcyclohexanone, dadurch gekennzeichnet, daß man Methylcyclohexanone mit 30°/oigem wäßrigem Wasserstoffperoxyd in Gegenwart von Dioxan behandet. PATENT CLAIM Process for the production of the peroxides of methylcyclohexanones, characterized in that one methylcyclohexanone with 30% aqueous hydrogen peroxide treated in the presence of dioxane. In Betracht gezogene Druckschriften: USA.-Patentschrift Nr. 2 750 421; britische Patentschrift Nr. 740747; Liebigs Ann. d. Chem., Bd. 565, 1949, S. 7 bis 21; Chim. & Ind., Bd. 74, 1955, S. 929 bis 939; J. Am. Chem. Soc., Bd. 61, 1939, S. 2430 bis 2432; J. prakt. Chem., Bd. 1S4, 1939/1940, S. 219 bis 237. References Considered: U.S. Patent No. 2,750 421; British Patent No. 740747; Liebigs Ann. d. Chem., Vol. 565, 1949, pp. 7 to 21; Chim. & Ind., Vol. 74, 1955, pp. 929-939; J. Am. Chem. Soc., Vol. 61, 1939, pp. 2430 to 2432; J. Prakt. Chem., Vol. 1S4, 1939/1940, pp. 219 to 237.
DEM38901A 1956-06-15 1957-06-14 Process for the preparation of the peroxides of methylcyclohexanones Pending DE1088485B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT1088485X 1956-06-15

Publications (1)

Publication Number Publication Date
DE1088485B true DE1088485B (en) 1960-09-08

Family

ID=11430655

Family Applications (1)

Application Number Title Priority Date Filing Date
DEM38901A Pending DE1088485B (en) 1956-06-15 1957-06-14 Process for the preparation of the peroxides of methylcyclohexanones

Country Status (1)

Country Link
DE (1) DE1088485B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3365501A (en) * 1962-10-26 1968-01-23 Konink Ind Mij Vorheen Noury & Preparation of mixtures of methylcyclohexanone peroxides having improved stability

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB740747A (en) * 1951-08-18 1955-11-16 Distillers Co Yeast Ltd Preparation of alpha-omega-dicarboxylic acids
US2750421A (en) * 1953-02-06 1956-06-12 Lonza Electric & Chem Works Process for the production of crystalline cyclohexyl peroxides

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB740747A (en) * 1951-08-18 1955-11-16 Distillers Co Yeast Ltd Preparation of alpha-omega-dicarboxylic acids
US2750421A (en) * 1953-02-06 1956-06-12 Lonza Electric & Chem Works Process for the production of crystalline cyclohexyl peroxides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3365501A (en) * 1962-10-26 1968-01-23 Konink Ind Mij Vorheen Noury & Preparation of mixtures of methylcyclohexanone peroxides having improved stability

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