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DE828842C - Process to prevent or delay the autoxidation of cyclic ethers - Google Patents

Process to prevent or delay the autoxidation of cyclic ethers

Info

Publication number
DE828842C
DE828842C DEJ261A DEJ0000261A DE828842C DE 828842 C DE828842 C DE 828842C DE J261 A DEJ261 A DE J261A DE J0000261 A DEJ0000261 A DE J0000261A DE 828842 C DE828842 C DE 828842C
Authority
DE
Germany
Prior art keywords
autoxidation
tetrahydrofuran
prevent
cyclic ethers
delay
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
DEJ261A
Other languages
German (de)
Inventor
Arthur William Charles Taylor
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries 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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Application granted granted Critical
Publication of DE828842C publication Critical patent/DE828842C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C07D307/08—Preparation of tetrahydrofuran
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Description

Verfahren zur Verhinderung bzw. Verzögerung der Autoxydation cyclischer Äther Die Erfindung bezieht sich auf ein Verfahren zum Verhindern der Autoxydation cyclischer Äther und besonders des Tetrahydrofurans.Process for preventing or delaying the autoxidation of cyclic Ether The invention relates to a method of preventing autoxidation cyclic ether and especially of tetrahydrofuran.

Es wurde bereits vorgeschlagen, dem Tetrahydrofuran Stabilisatoren, wie Hydrochinon oder p-Kresol, zuzusetzen, um die Bildung unerwünschter Autoxydationsprodukte des Tetrahydrofurans zu verzögern oder zu verhindern, wenn dieses längere Zeit sauerstoffhaltigen Gasen, beispielsweise der umgebenden Luft, ausgesetzt wird.It has already been suggested that the tetrahydrofuran stabilizers, such as hydroquinone or p-cresol, to be added to prevent the formation of undesirable auto-oxidation products to delay or prevent tetrahydrofuran if it contains oxygen for a longer period of time Gases, for example the surrounding air, is exposed.

Obwohl derartige Verzögerer die Autoxydation von Tetrahydrofuran unterdrücken, haben sie den Nachteil, daß Tetrahydrofuran, welches diese Stoffe enthält, sich leicht verfärbt, was vielfach unerwünscht ist. Es wurde nun gefunden, daß die Autoxydation cyclischer Äther und besonders von Tetrahydrofuran verhindert bzw. verzögert wird, indem man ihnen geringe Mengen eines trialkylierten Phenols, wie 2, 4, 6-Trimethylphenol, 2, 4-Dimethyl-ö-tert.-butylphenol oder 4-Methyl-2, 6-tert.-butylphenol zusetzt, wobei keine unerwünschte Entfärbung eintritt.Although such retarders suppress the auto-oxidation of tetrahydrofuran, they have the disadvantage that tetrahydrofuran, which contains these substances, is slightly discolored, which is often undesirable. It has now been found that the auto-oxidation cyclic ether and especially tetrahydrofuran is prevented or delayed, by giving them small amounts of a trialkylated phenol, such as 2, 4, 6-trimethylphenol, 2,4-Dimethyl-ö-tert-butylphenol or 4-methyl-2,6-tert-butylphenol added, with no undesired discoloration occurring.

Die folgenden Versuchsergebnisse zeigen die Vorteile, die bei Anwendung des erfindungsgemäßen Verfahrens erzielt werden.The following test results show the benefits of using of the method according to the invention can be achieved.

Beispiel Es wurde Tetrahydrofuran verwendet, das von allen nachweisbaren Spuren sowohl an Peroxyd als auch an Autoxydationsverzögerern durch Destillation befreit worden war. Je 4o ccm dieses Tetrahydrofurans wurden in konische Flaschen gefüllt und jeweils 5 - i0-5 Mol eines der unten näher gekennzeichneten Phenole zugegeben; eine Probe wurde für Vergleichszwecke ohne Zusatz gelassen. Diese Proben wurden in Berührung mit Luft bei Zimmertemperatur 8o Tage stehengelassen und folgende Ergebnisse erzielt: Peroxydgehält nach Zusatzmittel 8otagigem Stehen als Tetrahydrofuranperoxyd (g/Mol) i. Ohne Zusatz . . . . . . . . . . . . 0,034 2. Phenol................. 0,031 3. Hydrochinon ........... 0,004 4. 2, 4, 6-Trimethylphenol ... 0,002 5. 2, 4-Dimethyl-6-tert.- butylphenol . . . . . . . . . . . . 0,003 Das Hydrochinon als Verzögerer enthaltende Probe war verfärbt, während bei Verwendung von Trialkylphenolen als Verzögerer ein ansehnlicheres und nicht verfärbtes Produkt erhalten wurde.EXAMPLE Tetrahydrofuran was used which had been freed from all detectable traces of both peroxide and autoxidation retarders by distillation. 40 cc each of this tetrahydrofuran were filled into conical bottles and 5-10-5 mol of one of the phenols identified below were added in each case; one sample was left without additive for comparison purposes. These samples were left in contact with air at room temperature for 80 days and the following results were obtained: Peroxide content according to Additive for 8 days of standing as Tetrahydrofuran peroxide (g / mole) i. Without addition . . . . . . . . . . . . 0.034 2. Phenol ................. 0.031 3. Hydroquinone ........... 0.004 4.2, 4, 6-trimethylphenol ... 0.002 5. 2, 4-dimethyl-6-tert.- butylphenol. . . . . . . . . . . . 0.003 The sample containing hydroquinone as a retarder was discolored, while using trialkylphenols as a retarder a more attractive and non-discolored product was obtained.

Es ist festzustellen, daß bei diesen Versuchen etwa 0,02 bis 0,025 Gewichtsprozent an Trialkylphenol dem Tetrahydrofuran zugegeben worden waren. Im allgemeinen können befriedigende Ergebnisse erzielt werden, wenn bis zu i,o Gewichtsprozent Phenol indem cyclischen Äther vorhanden sind, jedoch ergeben auch für gewöhnlich Mengen von weniger als o,i Gewichtsprozent eine befriedigende Stabilisierung.It is found that about 0.02 to 0.025 percent by weight trialkylphenol was added to the tetrahydrofuran in these experiments. In general, satisfactory results can be obtained when up to 1.0 percent by weight of phenol is present in the cyclic ether, but amounts of less than 0.1 percent by weight usually give satisfactory stabilization.

Gesättigte cyclische Äther, bei denen das den Gegenstand der Erfindung bildende Verfahren angewandt werden kann, sind z. B. Tetrahydrofuran, Tetrahydropyran, Dioxan und ihre alkylsubstituierten Derivate.Saturated cyclic ethers, which are the subject of the invention Formative processes that can be applied are e.g. B. tetrahydrofuran, tetrahydropyran, Dioxane and their alkyl-substituted derivatives.

Claims (2)

PATENTANSPRÜCHE: i. Verfahren zur Verhinderung bzw. Verzögerung der Autoxydation cyclischer Äther oder ihrer alkylsubstituiertenDerivate, dadurch gekennzeichnet, daB dem Äther, z. B. Tetrahydrofuran oder dessen alkylsubstituiertem Derivat, eine geringe Menge eines Trialkylphenols zugesetzt wird. PATENT CLAIMS: i. Process for preventing or delaying the autoxidation of cyclic ethers or their alkyl-substituted derivatives, characterized in that the ether, e.g. B. tetrahydrofuran or its alkyl-substituted derivative, a small amount of a trialkylphenol is added. 2. Verfahren nach Anspruch i, dadurch gekennzeichnet, daB Trialkylphenol in einer Menge bis zu i,o Gewichtsprozent, vorzugsweise o,oi bis o,i Gewichtsprozent dem Äther oder dessen alkylsubstituiertem Derivat zugesetzt wird.2. Procedure according to Claim i, characterized in that trialkylphenol in an amount of up to i, o Percent by weight, preferably o, oi to o, i percent by weight of the ether or its alkyl substituted derivative is added.
DEJ261A 1948-12-13 1949-12-10 Process to prevent or delay the autoxidation of cyclic ethers Expired DE828842C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB828842X 1948-12-13

Publications (1)

Publication Number Publication Date
DE828842C true DE828842C (en) 1952-01-21

Family

ID=10535735

Family Applications (1)

Application Number Title Priority Date Filing Date
DEJ261A Expired DE828842C (en) 1948-12-13 1949-12-10 Process to prevent or delay the autoxidation of cyclic ethers

Country Status (1)

Country Link
DE (1) DE828842C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE948506C (en) * 1954-01-13 1956-09-06 Hoechst Ag Stabilizer for tetrahydrofuran
JPS492945A (en) * 1972-04-28 1974-01-11

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE948506C (en) * 1954-01-13 1956-09-06 Hoechst Ag Stabilizer for tetrahydrofuran
JPS492945A (en) * 1972-04-28 1974-01-11

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