DE753626C - Process for improving the antioxidant effect of alkylphenol sulfides - Google Patents

Process for improving the antioxidant effect of alkylphenol sulfides

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Publication number
DE753626C
DE753626C DEI63403D DEI0063403D DE753626C DE 753626 C DE753626 C DE 753626C DE I63403 D DEI63403 D DE I63403D DE I0063403 D DEI0063403 D DE I0063403D DE 753626 C DE753626 C DE 753626C
Authority
DE
Germany
Prior art keywords
improving
antioxidant effect
alkylphenol sulfides
treated
parts
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
DEI63403D
Other languages
German (de)
Inventor
Wolfgang Dr Haag
Hermann Dr Metzger
Hermann Dr Zorn
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEI63403D priority Critical patent/DE753626C/en
Application granted granted Critical
Publication of DE753626C publication Critical patent/DE753626C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/088—Neutral salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/089—Overbased salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/06—Groups 3 or 13
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/08—Groups 4 or 14

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Lubricants (AREA)

Description

In der französischen Patentschrift 824 600 ist gezeigt, daß man die Oxydationsbeständigkeit von Schmierölen in sehr bekannter Weise verbessern kann, wenn man ihnen Umsetzungsprodukte von alkylierten Phenolen mit Schwefelhalogeniden zusetzt. Diese Umsetzungsprodukte können aus ein- oder mehrkernigen Phenolen mit beliebiger Alkylgruppe im Kern hergestellt werden. Vorzugsweise verwendet man Phenole, deren ■ Alkylgruppen 4 bis 8Kohlenstoffatome enthalten, also z.B. Butyl-, Isobutyl-, Amyl- oder Diisobutylphenol. Die Umsetzung dieser alkylierten Phenole kann mit beliebigen Schwefelhalogeniden vorgenommen werden. Je nach deren Art und jeIn French patent 824 600 it is shown that the oxidation resistance of lubricating oils can be improved in a very known manner if reaction products of alkylated phenols with sulfur halides are added to them. These reaction products can be prepared from mono- or polynuclear phenols with any alkyl group in the core. Phenols whose alkyl groups contain 4 to 8 carbon atoms are preferably used, for example butyl, isobutyl, amyl or diisobutyl phenol. The reaction of these alkylated phenols can be carried out with any desired sulfur halides. Depending on their type and depending

nach den Reaktionsbedingungen erhält man entwederDialkylphenolmono-oder -polysulfide oder auch Verbindungen, in denen eine größere Anzahl von Alkylphenolresten durch Schwefelatome miteinander verbunden sind. Es wurde nun gefunden, daß man die Eigenschaften von Oxydationsverhinderern der genannten Art noch erheblich verbessern kann, wenn man sie mit Metallen der zweiten bis vierten Gruppe des Periodischen Systems oder deren Oxyden oder Hydroxyderii bzw. Oxydhydraten längere Zeit erhitzt. Geeignete Metalle sind beispielsweise die Erdalkalimetalle und Blei und insbesondere Aluminium und Zinn.Depending on the reaction conditions, either dialkylphenol mono- or polysulfides are obtained or compounds in which a larger number of alkylphenol residues occur Sulfur atoms are linked together. It has now been found that the properties of oxidation inhibitors of the type mentioned can still be improved considerably if they are used with metals of the second to fourth group of the periodic table or their oxides or hydroxyderii or Oxide hydrates heated for a long time. Suitable metals are, for example, the alkaline earth metals and lead and especially aluminum and tin.

Zweckmäßig führt man die Behandlung in Gegenwart von inerten Lösungsmitteln, vorzugsweise von Kohlenwasserstoffen, wie Toluol, Xylol, Schwerbenzin oder Schmierölen, aus. Es empfiehlt sich, die Metalle oder ihre Verbindungen in möglichst feinverteilter Form anzuwenden und die Masse während der Behandlung zu rühren. Zweckmäßig arbeitet man unter Ausschluß von Luft oder anderenThe treatment is expediently carried out in the presence of inert solvents, preferably of hydrocarbons such as toluene, xylene, heavy gasoline or lubricating oils, the end. It is advisable to distribute the metals or their compounds as finely as possible Apply the form and stir the mass during the treatment. Appropriate works one in the absence of air or others

ίο oxydierenden Gasen. Für die Erhitzung ■ kommen Temperaturen zwischen etwa ioo und 200°, vorzugsweise solche zwischen 120 und 1500, in Frage. Die Erhitzung muß längere Zeit dauern, beispielsweise 4 bis 8 Stunden.ίο oxidizing gases. For the heating temperatures ■ come between about ioo and 200 °, such preferably between 120 and 150 0, in question. The heating must take a long time, for example 4 to 8 hours.

Unter Umständen, insbesondere bei der Verwendung von Metallhydroxyden oder -oxydhydraten, wird bei der Behandlung Wasser gebildet, und man erhitzt dann so lange, bis diese Wasserbildung aufgehört hat. Nach Beendigung der Behandlung wird die flüssige Masse durch Filtrieren von dem überschüssigen Metall oder der Metallverbindung getrennt und erforderlichenfalls durch Destillation von dem Lösungsmittel befreit. Die abfiltrierten Metalle oder Metallverbindungen können erneut für die Behandlung verwendetUnder certain circumstances, especially when using metal hydroxides or oxide hydrates, water is formed during the treatment, and heating is then carried out until this water formation has ceased. After completion the treatment is the liquid mass by filtering off the excess Metal or the metal compound separately and, if necessary, by distillation freed from the solvent. The filtered metals or metal compounds can be used again for treatment

werden. π .will. π .

Beispiel 1example 1

Man löst 100 Teile Diisobutylphenolsulfid in 50 Teilen Xylol und erhitzt die Masse mit 5 Teilen feingepulvertem Zinn 5 Stunden zum Sieden. Nach dem Erkalten wird die Flüssigkeit vom überschüssigen Zinn abfiltriert und das Xylol abdestilliert.100 parts of diisobutylphenol sulfide are dissolved in 50 parts of xylene and the mass is heated 5 parts of finely powdered tin to boil for 5 hours. After cooling, the liquid becomes the excess tin is filtered off and the xylene is distilled off.

Setzt man 0,2% des so erhaltenen Produktes einem Schmieröl mit einer Viskosität von 30 E bei ioo° zu, so liefert die Mischung folgende Werte im British Air Ministry Test:Substituting 0.2% of the product thus obtained a lubricating oil having a viscosity of 3 0 E at ioo ° to, the mixture yields the following values in the British Ministry test Air:

4040 Säurezal 1 Acidzal 1 Mit Stickstoff
behandeltWith nitrogen
treated Mit Luft
behandeltWith air
treated Verseifungszahl
Viskosität bei 380C..
Verdickung Saponification number
Viscosity at 38 0 C ..
thickening 0,03
0,55
74,0° E0.03
0.55
74.0 ° E 2,42
8,8
122,2° E2.42
8.8
122.2 ° E 4545

Setzt man dagegen dem gleichen Öl nichtbehandeltes Diisobutylphenolsulfid in einer Menge von 0,2% zu, so erhält man folgende Werte:If, on the other hand, untreated diisobutylphenol sulfide is used in the same oil Amount of 0.2%, the following values are obtained:

Säurezahl Acid number

Verseifungszahl Saponification number

Viskosität bei 38 ° C ..
Verdickung Viscosity at 38 ° C ..
thickening

Mit Stickstoff behandeltTreated with nitrogen

0,02 0,50 0.02 0.50

74>9°74> 9 °

Mit Luft behandeltTreated with air

4.694.69

10,9010.90

140,I0E140, I 0 E

Beispiel 2 Example 2

Säurezahl Acid number

Verseifungszahl Saponification number

Viskosität bei 38 ° C
Verdickung Viscosity at 38 ° C
thickening

Mit Stickstoff behandeltTreated with nitrogen

0,02 0,380.02 0.38

Mit Luft behandeltTreated with air

Beispiel 3Example 3

Eine Lösung von 300 Teilen Diisooctylphenolsulfid in 300 Teilen Xylol wird mit 25 Teilen frisch gefälltem, noch etwas Chlor enthaltendem Aluminiumhydroxyd so lange gekocht, bis kein Wasser mehr gebildet wird. Nach dem Erkalten nitriert man vom überschüssigen Aiuminiumhydroxyd ab und entfernt das Xylol durch Destillation. Setzt man ο, ι % des so erhaltenen Produktes dem im Beispiel 1 genannten Schmieröl zu, so ergeben sich nach dem British Air Ministry Test folgende Werte:A solution of 300 parts of diisooctylphenol sulfide in 300 parts of xylene is with 25 parts of freshly precipitated aluminum hydroxide, which still contains a little chlorine, is so long cooked until no more water is formed. After cooling, the excess is nitrated Aiuminiumhydroxyd and removed the xylene by distillation. If you set ο, ι% of the product thus obtained to the lubricating oil mentioned in Example 1, so result According to the British Air Ministry test, the following values were found:

Säurezahl Acid number

Verseifungszahl Saponification number

Viskosität bei 38 ° C
Verdickung Viscosity at 38 ° C
thickening

Mit Stickstoff behandeltTreated with nitrogen

0,08 0,080.08 0.08

Mit Luft behandeltTreated with air

Eine Lösung von 500 Teilen Diisobutylphenolsulfid in 500 Teilen Xylol wird mit 115 g frisch gefälltem, zweckmäßig etwas Stannooxychlorid enthaltendem Stannohydroxyd so lange gekocht, bis kein Wasser mehr gebildet wird. Nach dem Erkalten filtriert man die Lösung und entfernt, das Xylol durch Destillation.A solution of 500 parts of diisobutylphenol sulfide in 500 parts of xylene is with 115 g of freshly precipitated stannous hydroxide, suitably containing some stannous oxychloride cooked until no more water is formed. After cooling, the solution is filtered and the Xylene by distillation.

Setzt man 0,2% des so erhaltenen Produktes dem im Beispiel 1 genannten Schmieröl zu, so ergeben sich beim British Air Ministry Test folgende Werte:If 0.2% of the product thus obtained is added to the lubricating oil mentioned in Example 1 to, the British Air Ministry test gives the following values:

4.094.09

5 5o%5 5o%

Claims (1)

Patentanspruch:Claim: 2,352.35 7,707.70 106,80E106.8 0 E. + 37%+ 37% Verfahren zur Verbesserung der oxydationsverhindernden Wirkung von Alkylphenolsulfiden, dadurch gekennzeichnet, daß man die in bekannter Weise her- »o gestellten Umsetzungsprodukte von alkylierten Phenolen und Schwefelhalogeniden zusammen mit Metallen der zweiten bis vierten Gruppe des Periodischen Systems oder deren Oxyden oder Hydroxyden bzw. "5 Oxydhydraten längere Zeit erhitzt.Process for improving the anti-oxidation Effect of alkylphenol sulfides, characterized by that one produces the reaction products of alkylated in a known manner Phenols and sulfur halides together with metals of the second to fourth groups of the periodic table or their oxides or hydroxides or oxydhydrates are heated for a long time. © 5820 3.53© 5820 3.53
DEI63403D 1939-01-04 1939-01-05 Process for improving the antioxidant effect of alkylphenol sulfides Expired DE753626C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI63403D DE753626C (en) 1939-01-04 1939-01-05 Process for improving the antioxidant effect of alkylphenol sulfides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE894405X 1939-01-04
DEI63403D DE753626C (en) 1939-01-04 1939-01-05 Process for improving the antioxidant effect of alkylphenol sulfides

Publications (1)

Publication Number Publication Date
DE753626C true DE753626C (en) 1953-04-09

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1145630B (en) * 1958-03-12 1963-03-21 Ethyl Corp Process for the preparation of antioxidant, alkyl-substituted bis (4-hydroxyphenyl) sulfides
DE1275067B (en) * 1959-01-29 1968-08-14 Ferro Corp Process for the preparation of crystalline bis [3- (1 ', 1', 3 ', 3'-tetramethylbutyl) -6-hydroxyphenyl] monosulfide

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1145630B (en) * 1958-03-12 1963-03-21 Ethyl Corp Process for the preparation of antioxidant, alkyl-substituted bis (4-hydroxyphenyl) sulfides
DE1275067B (en) * 1959-01-29 1968-08-14 Ferro Corp Process for the preparation of crystalline bis [3- (1 ', 1', 3 ', 3'-tetramethylbutyl) -6-hydroxyphenyl] monosulfide

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