DE1282828B - Esterschmieroel - Google Patents

Esterschmieroel

Info

Publication number
DE1282828B
DE1282828B DES90657A DES0090657A DE1282828B DE 1282828 B DE1282828 B DE 1282828B DE S90657 A DES90657 A DE S90657A DE S0090657 A DES0090657 A DE S0090657A DE 1282828 B DE1282828 B DE 1282828B
Authority
DE
Germany
Prior art keywords
ester lubricating
acid
ppm
lubricating oil
ester
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
DES90657A
Other languages
English (en)
Inventor
Derek Southern Heswall
Alexander Colquhoun B Macphail
Francis Henry Waight
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of DE1282828B publication Critical patent/DE1282828B/de
Pending legal-status Critical Current

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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
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    • C07—ORGANIC CHEMISTRY
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
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    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
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    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
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    • C10M137/105—Thio derivatives not containing metal
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    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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Description

BUNDESREPUBLIK DEUTSCHLAND
DEUTSCHES
PATENTAMT
AUSLEGESCHRIFT
Int. CL:
ClOm
Deutsche Kl.: 23 c-1/01
Nummer: 1 282 828
Aktenzeichen: P 12 82 828.3-43 (S 90657)
Anmeldetag: 21. April 1964
Auslegetag: 14. November 1968
CO CO CO
Es sind schon verschiedene organische Stoffe als Zusatz zu Esterschmierölen empfohlen worden, um ihnen Hochdruck- oder Extrerndruckeigenschaften zu verleihen, z. B. chlorierte Di- und Polyphenylverbindungen. Solche Zusätze müssen aber auch »sauber« sein, womit gemeint ist, daß sie unter abbauenden Arbeitsbedingungen des Motors keinen Anlaß zur Niederschlagsbildung geben. Außerdem müssen sie auch thermisch stabil sein, da Esterschmieröle bei hohen Temperaturen eingesetzt werden.
Es ist nun gefunden worden, daß gewisse neue Diarylhalogenalkylphosphate als Extremdruckzusätze besonders geeignet sind, insbesondere wenn sie in relativ geringen Mengen zu Esterschmierölen zugesetzt werden, und daß sie auch die erforderlichen Eigenschaften der Sauberkeit und thermischen Stabilität aufweisen. Sie wirken weit besser als die bekannten Zusatzstoffe.
Das erfindungsgemäße, 0.1 bis K) Gewichtsprozent eines Diarylhalogenalkylphosphats enthaltende Esterschmieröl isl dadurch gekennzeichnet, daß es ein Diarylhalogenalkylphosphat der allgemeinen Formel
RO
Esterschmieröl
CH,C(Y),
RO
worin R Arylreste sind, die gegebenenfalls durch eine oder mehrere Ci m-Alkylreste substituiert sein können. X Sauerstoff oder Schwefel bedeutet und Y gleiche oder verschiedene Reste von CH>C1, CFlCIi. CCIn. CHi und C2Hr1 sind, wobei jedoch nur ein CHa- oder C2H.-,-Rest vorhanden ist. enthält.
Die neuen Diarylhalogenalkylphosphate. die in den Esterschmierölen gemäß der Erfindung verwendet werden, können am besten hergestellt werden durch Umsetzen eines 3-Halogenalkyloxetans mit Salzsäure und darauffolgende Behandlung des bei dieser Reaktion gebildeten Alkohols mit einem Phosphorsäurechlorid von der allgemeinen Formel
RO
RO
P-Cl
in welcher R und X die vorstehend angegebene Bedeutung haben.
Beispiele für diese neuen Diarylhalogenalkylphosphate sind Diphenyl-2.2 -bis-(chlormethyl)-3 - chlorpropylphosphat. Diphenyl - 2.2 - bis - (chlor-Anmelder:
Shell Internationale Research Maatschappij N. V.. Den Haag
Vertreter:
Dr. E. Jung, Patentanwalt,
8000 München 23, Siegesstr. 26
Als Erfinder benannt:
Derek Southern Heswall, Wirral, Cheshire;
Francis Henry Waight,
Eastham, Wirral, Cheshire;
Alexander Colquhoun Barr Macphail,
Little Sutton, Wirral, Cheshire (Großbritannien)
Beanspruchte Priorität:
Großbritannien vom 23. April 1963 (15 953)
methyl) - 3 - chlorpropylphosphorthionat, Dioctylphenyl-2,2-bis-(chlormethyl)-3-chlorpropylphosphat, Dioctylphenyl - 2,2 - bis -(chlormethyl) - 3 -chlorpropylphosphorthionat.
Die nachstehenden Angaben dienen zur Erläuterung der Herstellungsmethode der neuen Extremdruckzusatzstoffe.
Herstellungsverfahren I
Diphenyl-2,2-bis-(chlormethyl)-3-chlorpropylphosphat
3.3-Bis-(chlormethyl)-oxetan (989 g) (6,38 Mol) werden in eine 2-1-Flasche eingebracht, die mit einem bis zum Boden der Flasche reichenden Einführungsrohr, einem Thermometer und einem Kondensator mit einem Gaszuführungsrohr versehen isl. Das Oxetan wird bis zum Schmelzen erhitzt, und dann wird während 2 Stunden Chlorwasserstoff durch die Flasche hindurchgeblasen. In dieser Zeit erhöht sich die Reaktionstemperatur langsam bis zu einem Maximum von 110 C. Das Reaktions-
809 637/882
3 4
produkt wird erst mit verdünnter Natriumcarbonat- durch Waschen mit NaOH-Lösung aktiviert worden lösung, dann mit Wasser bis zur neutralen Reaktion ist. Nach dem Filtrieren wird das Lösungsmittel abgewaschen und schließlich destilliert. Das so erhaltene destilliert, wobei ein bernsteinfarbiges flüssiges Pro-2,2-Bis-(chlormethyl)-3-chlorpropanol hat folgende dukt zurückbleibt, welches Di-p-octylphenyl-2,2-di-Analysendaten: 5 (chlormethylJ-S-chlorpropylphosphat ist und die fol
genden Analysenwerte ergibt:
Chlor (Gewichtsprozent) 53,9
Hydroxylwert 5,12 Säurewert 0,7 mg/KOH/g
Freies Chlorid 0
100 g (0,52 Mol) des 2,2-Bis-(chlormethyl)-3-chlor- io Chlor (Gewichtsprozent) 16,45
propanols, 134 g (0,5MoI) Phosphorsäurediphenyl-
esterchlorid und Pyridin (50 g) (0,63 Mol) werden Die Esterschmieröle gemäß vorliegender Erfindung
in einer Flasche geschüttelt, wobei das Reaktions- enthalten die Diarylhalogenalkylphosphate in kleigefäß mit Wasser gekühlt wird, bis die Reaktion neren Mengen von vorzugsweise 2 bis 6 Gewichtsaufhört. Nach Zugabe von Toluol (50 ecm) wird 15 prozent, berechnet auf die fertige Mischung.
4 Stunden unter Rückfluß erhitzt. Das abgekühlte Als Basisschmieröle werden vorzugsweise alipha-
Reaktionsgemisch wird mit 50 ecm leichtem Petro- tische Diester aus zweibasischen Carbonsäuren mit leumspirit (Siedepunkt 100 bis 12O0C, Benzol 6 bis 20 Kohlenstoffatomen und einwertigen Alko-(50 ecm) und Wasser (50 ecm) verdünnt. Die ge- holen mit 1 bis 5 Kohlenstoffatomen eingesetzt, z. B. bildete organische Schicht wird nacheinander mit 20 Ester von Adipinsäure, Pimelinsäure, Suberinsäure, Wasser, verdünnter Natriumbicarbonatlösung und Azelainsäure und Sebazinsäure mit Laurylalkohol, Wasser bis zur neutralen Reaktion gewaschen. Heptylalkohol, Octylalkohol und Nonylalkohol.
Wasser und organisches Lösungsmittel werden durch Die Esterschmieröle gemäß der Erfindung können
Destillation entfernt, und das Endprodukt wird unter auch weitere bekannte Zusatzstoffe enthalten, wie vermindertem Druck destilliert. Beim Abkühlen 25 z. B. Verdickungsmittel, Antioxydationsmittel, die kristallisiert Diphenyl^^-bis-ichlormethyty-S-chlor- Lackbildung verhindernde Mittel, schaumhindernde propylphosphat als weißer Festkörper aus, der Mittel, Farbstoffe, korrosionshindernde Mittel, Mefolgende Analysenwerte ergibt: tallentaktivatoren und gewünschtenfalls zusätzliche
JixtremdruckzusatzstofTe.
Säurewert 0 30 Geeignete Verdickungsmittel sind Polyalkylen-
Freies Chlorid 0 sulfone und ihre Mono- oder Diäther und Ester
Chlor (Gewichtsprozent) 24,8 sowie die Polymeren der Ester von Acrylsäure oder
1 -Alkylacrylsäure, wie in der britischen Patentschrift 703 445 beschrieben.
Herstellungsverfahren II 35 Eine besonders bevorzugte Klasse von Antioxy-
Dioctylphenyl-2,2-bis-(chlormethyl)- dationsmitteln bilden die Thiodiarylamine z. B.
3-chlorpropylphosphat Phenothmzm und 3,7-Dioctylphenothiazm. Es können
auch Gemische von Antioxydationsmitteln ver-
Destilliertes p-Octylphenol (116 g) (0,56 Mol) und wendet werden, insbesondere Gemische, die ein Thiodestilliertes Phosphorylchlorid (43,2 g) (0,28 Mol) 4c diarylamin enthalten, z. B. ein Gemisch von Phenowerden in einen Kolben eingebracht, der mit Thermo- thiazin und Phenyl-alpha-naphthylamin.
meter und Rührvorrichtung ausgerüstet ist. Die Geeignete schaumhindernde Mittel sind die PolyTemperatur des Reaktionsgemisches wird im Verlauf dimethylsiloxane mit einer Viskosität von 100 bis von 2 Stunden langsam auf 228 0C gesteigert und 100 000 sC bei 251C.
weitere 2 Stunden auf diesem Wert gehalten. Das 45 Beispiele von Antikorrosionsmitteln und Metallerhaltene Produkt wird destilliert, und die bis 2400C entaktivatoren sind Benzotriazol, 5-Methylbenzobei 15 mm Hg siedende Fraktion wird analysiert triazol und Dicarbonsäuren mit niedrigem MoI- und ergibt die Werte für Phosphorsäure-di-p-octyl- gewicht, wie Azelainsäure und Pimelinsäure,
phenylester-chlorid: Andere geeignete Extremdruckzusatzstoffe sind
50 z. B. die chlorierten Di- oder Polyphenyle und die
Chlor (Gewichtsprozent) 7,20 Triarylester von Phosphor- oder Phosphorothion-
säure.
27,6 g (0,06 Mol) Phosphorsäure-di-p-octylphenyl- Um die verbesserten Schmieröle gemäß der vor-
ester-chlorid, 13,8 g (0,07 Mol) 2,2-Bis-(chlormethyl)- liegenden Erfindung weiter zu erläutern, wurden 3-chlorpropanol, hergestellt nach dem Herstellungs- 55 Gemische der in Tabelle I angegebenen Zusammenverfahren I, und Pyridin (6 g) (0,01 Mol) werden in Setzung (Beispiele 4 bis 7) hergestellt, geprüft und mit einer Flasche unter Kühlung geschüttelt. Nach Zu- dem Basisöl (Beispiel 1) sowie Mischungen versatz von Toluol (50 ecm) wird das Gemisch unter glichen, welche die gleichen Mengen eines bekannten Rückfluß 4 Stunden erhitzt, wobei sich zwei getrennte Extremdruckzusatzstoffes enthielten (Beispiele 2 Phasen bilden. Das Produkt wird verdünnt mit 60 und 3).
100 ecm einer Mischung aus leichtem Petroleum- Diese Mischungen wurden auf ihr Belastungsverspirit (Siedepunkt 100 bis 12O0C) und Benzol, und mögen geprüft in einem I. A. E.-Getriebekasten, wie es wird dann mit Wasser, verdünnter Natriumbi- beschrieben in der Vorschrift 166/60 T des Institute carbonatlösung und Wasser bis zur neutralen Re- of Petroleum, welcher bei einer öltemperatur von aktion gewaschen, worauf man das Lösungsmittel 65 entweder 60 oder 1100C arbeitete. Die mittleren abdestilliert. Der Rückstand, der freies Chlorid ent- Grenzbelastungen bei 2000 und 6000 U/min bei den hält, wird mit Toluol verdünnt und diese Lösung mit beiden vorgenannten Temperaturen wurden beeinem Ionenaustauscherharz aufgeschlämmt, das stimmt und in Tabelle II zusammengestellt.
Tabelle I
Zusammensetzung nach Beispiel
3 I 4 I 5
Gewichtsprozent
6 j 7
Di-(isooctylazelat)
Chloriertes Diphenyl
Diphenyl-^-bis-chlormethyl-3-chlorpropylphosphat
Di-octylphenyl-^-bischlormethyl-3-chlorpropylphosphat
3,7-Dioctylphenothiazin ...
Phenyl-alpha-naphthylamin
5-Methylbenzotriazol
Azelainsäure
Silicon/Antischaummittel ..
100,0
93,98 3,0
1,5 1,5
25 ppm 0,02 5 ppm
91,98 5,0
25 ppm 0,02 5 ppm 93,98
3,0
1,5
1,5
25 ppm
0,02
5 ppm
91,98
5,0
1,5
1,5
25 ppm 0,02
5 ppm
93,98
3,0 1,5 1,5
25 ppm 0,02 5 ppm
Tabelle II
91,98
5,0 1,5 1,5
25 ppm 0,02 5 ppm
1 2 3 Beispiel
4		 5 6 7
I. A. E.-Freßbelastung (kg)
2000 U/min
60 C 		25,4
25,4
15,42
10,43
76,65		 37,65
33,57
18,14
14,51
103,87		 43,09
36,29
20,41
16,33
116,12		 47,63
38,56
22,68
20,41
129,28		 58,97
43,09
24,95
22,68
149,69		 43,09
38,56
20,41
18,14
120,20		 49,90
40,82
24,93
20,41
136,06
110 C
6000 U/min
60 C
110"C
Summe
der Freßbelastung (kg) ..
Aus den Resultaten in Tabelle II ist deutlich zu ersehen, daß die Esterschmieröle gemäß der Erfindung, welche die neuen Diarylhalogenalkylphosphate enthalten, überlegene Belastungseigenschaften haben im Vergleich zu ähnlichen Mischungen, welche dieselben Mengen eines in der Praxis laufend verwendeten Höchstdruckzusatzstoffes enthalten.
ROn

Claims (1)

  1. Patentanspruch:
    Esterschmieröl, enthaltend 0,1 bis 10 Gewichtsprozent eines Diarylhalogenalkylphosphates, dadurch gekennzeichnet, daß es ein Diarylhalogenalkylphosphat der allgemeinen Formel
    RO
    P-O- CH2C(Y)3 X
    worin R Arylreste sind, die gegebenenfalls durch eine oder mehrere Ci lo-Alkylreste substituiert sein können, X Sauerstoff oder Schwefel "bedeutet und Y gleiche oder verschiedene Reste von CH2Cl, CHCl2, CCk, CH3 und C2H5 sind, wobei jedoch nur ein CH3- oder C2Hs-ReSt vorhanden ist, enthält.
    In Betracht gezogene Druckschriften: Britische Patentschrift Nr. 763 967.
    809 617/882 11.68 O Bundesdruckerei Berlin
DES90657A 1963-04-23 1964-04-21 Esterschmieroel Pending DE1282828B (de)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB15953/63A GB1035984A (en) 1963-04-23 1963-04-23 Chlorine-containing phosphorus esters and lubricating oil compositions containing them

Publications (1)

Publication Number Publication Date
DE1282828B true DE1282828B (de) 1968-11-14

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US (1) US3287266A (de)
BE (1) BE646836A (de)
DE (1) DE1282828B (de)
GB (1) GB1035984A (de)
NL (1) NL6404323A (de)

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US4159960A (en) * 1977-05-02 1979-07-03 Mobil Oil Corporation Lubricant compositions
US5279752A (en) * 1989-02-22 1994-01-18 Nippon Oil Co., Ltd. Composition for lubricating oil

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GB763967A (en) * 1952-04-21 1956-12-19 Monsanto Chemicals Lubricating compositions

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US2289509A (en) * 1933-11-01 1942-07-14 Atlantic Refining Co Lubricant
US2758091A (en) * 1947-10-28 1956-08-07 Shell Dev Lubricating compositions
US2656373A (en) * 1950-04-14 1953-10-20 Monsanto Chemicals Process for producing mixed diaryl esters of ortho-phosphoric acid
US2760937A (en) * 1951-10-31 1956-08-28 Exxon Research Engineering Co Phosphorus-containing lubricant additives
NL247300A (de) * 1959-01-14

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Publication number Priority date Publication date Assignee Title
GB763967A (en) * 1952-04-21 1956-12-19 Monsanto Chemicals Lubricating compositions

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GB1035984A (en) 1966-07-13
BE646836A (de) 1964-10-21
US3287266A (en) 1966-11-22
NL6404323A (de) 1964-10-26

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