DE1273105B - Esterschmieroel - Google Patents

Esterschmieroel

Info

Publication number
DE1273105B
DE1273105B DES96776A DES0096776A DE1273105B DE 1273105 B DE1273105 B DE 1273105B DE S96776 A DES96776 A DE S96776A DE S0096776 A DES0096776 A DE S0096776A DE 1273105 B DE1273105 B DE 1273105B
Authority
DE
Germany
Prior art keywords
lubricating oil
hal
acid
chloropropyl
chloromethyl
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
DES96776A
Other languages
English (en)
Inventor
Alexander Colquhoun Ba Mcphail
Derek Southern
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 DE1273105B publication Critical patent/DE1273105B/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
    • C10M131/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen
    • C10M131/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen containing carbon, hydrogen, halogen and oxygen
    • C10M131/12—Acids; Salts or esters thereof
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/22—Acids obtained from polymerised unsaturated acids
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    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

BUNDESREPUBLIK DEUTSCHLAND
DEUTSCHES
PATENTAMT
AUSLEGESCHRIFT
Int. Cl.:
Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:
ClOm
Deutsche KL: 23 c-1/01
P 12 73 105.4-43 (S 96776)
26. April 1965
18. Juli 1968
Die vorliegende Erfindung bezieht sich auf ein Esterschmieröl, welches dadurch gekennzeichnet ist, daß es zusätzlich einen Ester der allgemeinen Formel
(Y)3C — CH2OOC — (CH2)„ — X
in welcher X ein primärer, sekundärer oder tertiärer Alkylrest oder — COOCH2 · C(Y)3, Y = - CH2HaI, -CH(HaI)2, -C(HaI)3, -CH3 oder -C2H5 und Hai = Halogen, vorzugsweise Chlor, ist, wobei aber nicht mehr als ein Y ein Methyl- oder Äthylrest sein soll, und η 2 bis 12 ist oder, falls X ein Alkylrest ist, den Wert 0 hat, enthält.
Diese zusätzlichen Ester können nach irgendeinem geeigneten Verfahren hergestellt werden. Eine sehr günstige Methode besteht darin, daß man ein Halogenalkyl-Oxetan mit Chlorwasserstoff umsetzt und den so gebildeten Alkohol anschließend mit einer Carbonsäure behandelt.
Für diesen Zweck geeignete Carbonsäuren sind aliphatische Mono- oder Dicarbonsäuren, beispielsweise n-Hexansäure, n-Heptansäure, n-Nonansäure, Azelainsäure und Sebacinsäure. Falls es sich um Monocarbonsäuren handelt, können diese Säuren vom primären, sekundären oder tertiären Typ sein, wie Pivalinsäure.
Beispiele für die zusätzlichen Ester sind Di-(2,2-bischlormethyl-3-chlorpropyl)-azetat, 2,2-Bis-(chlormethyl)-3-chlorpropyl-n-octoat, 2,2-Bis-(chlormethyl)-3-chlorpropyl-pivalat, 2,2-Bis-(chlormethyl)-3-chlorpropyl-hexoat und Di-[2,2-bis-(chlormethyl)-chlorpropyl]-sebacat.
Die neuen Esterschmieröle weisen ein ausgezeichnetes Verhalten auch bei sehr hohen Belastungen auf, und sie zeigen eine hohe Stabilität sowie geringe Verschmutzung.
Nachstehend wird eine bevorzugte Methode zur Herstellung der zusätzlichen Ester erläutert, für diese Herstellung wird jedoch im Rahmen der Erfindung kein Schutz beansprucht.
Herstellung von
Di-[2,2-bis-(chlormethyl)-3-chlorpropyl]-azelat
989 g (6,38 Mol) 3,3-Bis-(chlormethyl)-oxetan werden in einen Dreihalskolben von 21 Fassungsvermögen eingefüllt, welcher ein bis zum Kolbenboden reichendes Gaseinlaßrohr, ein Thermometer und einen Kondensator mit Blasenrohr aufweist. Das Oxetan wird aufgeschmolzen, und dann läßt man 2 Stunden lang gasförmigen Chlorwasserstoff durch den Kolbeninhalt hindurchperlen. Die Reaktionstemperatur wird dabei langsam bis zu einem Maximum von 1000C erhöht.
Esterschmieröl
Anmelder:
Shell Internationale Research
Maatschappij, N. V., Den Haag
Vertreter:
Dr. E. Jung, Patentanwalt,
8000 München 23, Siegesstr. 26
Als Erfinder benannt:
Alexander Colquhoun Barr McPhail,
Little Sutton;
Francis Henry Waight, Eastham;
Derek Southern, Heswall, Wirral,
Chesh. (Großbritannien)
Beanspruchte Priorität:
Großbritannien vom 27. April 1964 (17 305)
Das Reaktionsprodukt wird dann mit verdünnter Natriumcarbonatlösung und anschließend mit Wasser bis zur neutralen Reaktion gewaschen. Das Rohprodukt wird unter Wasserstrahl-Vakuum fraktioniert destilliert, und man erhält so 485 g (2,53 Mol) der Verbindung 2,2-Bis-(Chlormethyl)-3-chlorpropanol, welche die folgenden Eigenschaften hat: Kp. 130 bis 133°C/12mmHg; F. 620C.
g (0,87 Mol) dieses Alkohols werden zusammen mit 75 g (0,40 Mol) Azelainsäure, 4 g p-Toluolsulfonsäuremonohydrat und 50 ml Xylol in einen Dreihalskolben von 500 ml Fassungsvermögen eingefüllt, der einen Rührer, ein Thermometer und eine Wasserfalle aufweist. Das Gemisch läßt man I1J1 Stunden lang bei einer Bodentemperatur von 2000C am Rückfluß sieden, während welches Zeitraumes sich 15 ml Wasser in der Falle ansammeln. Das dunkelbraune Reaktionsgemisch wird anschließend nacheinander mit Wasser, verdünnter Natriumcarbonatlösung und wiederum Wasser bis zur neutralen Reaktion gewaschen und dann zwecks Entfernung des Lösungsmittels destilliert. Anschließend setzt man 200 ml Chloroform zu und schlämmt diese Lösung mit einem bei 12O0C aktivierten Kieselsäuregel zwecks Entfernung der Hydroxyverbindung und der farbgebenden Stoffe auf. Das Gel wird dann abfiltriert und das Filtrat mit einem durch Waschen mit wäßrigem
809 570/494
Natriumhydroxyd aktivierten Ionenaustauschharz aufgeschlämmt. Nach dem Abfiltrieren des Harzes und einer Destillationsbehandlung zwecks Entfernung des Lösungsmittels erhält man 130 g des flüssigen Di-[2,2-bis-(chlormethyl)-3-chlorpropyl]-azeIats.
Die neuen halogenhaltigen Ester liegen in den erfindungsgemäßen Schmierölgemischen vorzugsweise in Mengen von 0,1 bis 10 Gewichtsprozent und insbesondere von 2 bis 6 Gewichtsprozent, bezogen auf das fertige Gemisch, vor.
Als synthetisches Basisschmieröl werden vorzugsweise ah'phatische Carbonsäureester verwendet, beispielsweise aliphatische Diester, die sich von zweibasischen Carbonsäuren mit 6 bis 20 Kohlenstoffatomen und einwertigen Alkohol mit 1 bis 12 Kohlenstoffatomen ableiten. Geeignete Ester dieser Art leiten sich von Adipinsäure, Pimelinsäure, Suberinsäure, Azelainsäure und Sebacinsäure in Kombination mit Laurylalkohol, Heptylalkohol, Octylalkohol und Nonylalkohol ab.
Die erfindungsgemäßen Schmierölgemische können zusätzlich andere bekannte Zusatzstoffe enthalten, beispielsweise Verdickungsmittel, Antioxydationsmittel, die die Lackbildung verhindernde Mittel, Antischaummittel, Farbstoffe, Antikorrosionsmittel, Metalldesaktivatoren und weitere Hochdruckzusatzstoffe.
Um die Vorzüge der erfindungsgemäßen Schmiermittelgemische näher zu erläutern, wurden die in der Tabelle I angegebenen Mischungen IV bis VII hergestellt, geprüft und mit dem Basisschmieröl der Gemische (Beispiel I) sowie entsprechenden Zusammensetzungen verglichen, welche den gleichen Prozentsatz
ίο an einem bekannten Höchstdruckzusatzstoff enthielten (Gemische II und III).
Die Schmiermittelgemische wurden hinsichtlich ihrer Belastbarkeit in einem Getriebeprüfstand gemäß den Vorschriften des Institute of Automobile Engineers
(I. A. E.) untersucht, wie es in der Veröffentlichung vom Institute of Petroleum Method 166/60 T beschrieben ist. Es wurden dabei Stahlgetriebe (BSS-EN 34) verwendet, und die Messungen wurden bei einer Öltemperatur von 60 und 110° C durchgeführt.
Es wurde diejenige durchschnittliche Belastung bei 2000 bzw. 6000 Umdr./Min. bei den beiden angegebenen Temperaturen bestimmt, bei der ein Versagen des Getriebes auftrat. Die dabei erzielten Ergebnisse sind in Tabelle II zusammengestellt.
Tabelle I
Zusammensetzung der untersuchten Gemische in Gewichtsprozent
I Π III IV V VI
100,0 93,98 91,98 93,98 91,98 93,98
3,0 5,0
3,0 5,0
3,0
1,5 1,5 1,5 1,5 1,5
1,5 1,5 1,5 1,5 1,5
25 25 25 25 25
0,02 0,02 0,02 0,02 0,02
5 5 5 5 5
νπ
Diisooctylsebacat
Chloriertes Diphenyl
2,2-Bis-(chlormethyl)-3-chlorpropyl-
chlorpropyl-pivalat
Di-[2,2-bis-(chlormethyl)-3-chlorpropyl]-
azelat
3,7-Dioctylphenothazin
Phenyl-a-naphthylamin
S-Amino-S-anilido-l^^-triazol, ppm ...
Azelainsäure
Antischaummittel, ppm
91,98
5,0 1,5 1,5
25
0,02 5
Tabelle II
I Π m IV V VI VII
IAE-Belastung beim Festfressen, kg
2000 UpM
6O0C 		25,4
25,4
15,42
10,43		 37,65
33,57
18,14
14,52		 43,09
36,29
20,41
16,33		 40,82
35,38
20,87
17,24		 45,36
38,56
24,95
20,41		 39,46
34,02
19,50
15,88		 40,82
36,29
22,68
18,14
110°C 76,65 103,88 116,12 114,31 129,28 108,86 117,93
6000 UpM
6O0C
110°C
Summe der Belastungen, kg
Aus einem Vergleich der in Tabelle II zusammengesetzten Ergebnisse ist ersichtlich, daß diejenigen Schmierölgemische, welche die neuen halogenhaltigen Ester gemäß der Erfindung enthalten, wesentlich bessere Eigenschaften hinsichtlich der Belastbarkeit aufweisen als entsprechende Zusammensetzungen, welche die gleiche Menge an üblichen Hochdruckzusatzstoffen aufweisen.

Claims (1)

  1. Patentanspruch:
    Esterschmieröl, dadurch gekennzeichnet, daß es zusätzlich einen Ester der allgemeinen Formel
    (Y)3C — CH2OOC — (CH2),, — X
    in welcher X ein primärer, sekundärer oder tertiärer Alkylrest oder—COOCH2 · C(Y)3, Y = - CH2HaI, -CH(HaI)2, -C(HaI)3, -CH3 oder -C2H5 und Hai = Halogen, vorzugsweise Chlor, ist, wobei aber nicht mehr als ein Y ein Methyl- oder Äthylrest sein soll, und η 2 bis 12 ist oder, falls X ein Alkylrest ist, den Wert 0 hat, enthält.
    809 570/494 7.68 © Bundesdruckerei Berlin
DES96776A 1964-04-27 1965-04-26 Esterschmieroel Pending DE1273105B (de)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB17305/64A GB1040992A (en) 1964-04-27 1964-04-27 Polychlorinated esters and their use in lubricating oil compositions

Publications (1)

Publication Number Publication Date
DE1273105B true DE1273105B (de) 1968-07-18

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Family Applications (1)

Application Number Title Priority Date Filing Date
DES96776A Pending DE1273105B (de) 1964-04-27 1965-04-26 Esterschmieroel

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Country Link
US (1) US3260672A (de)
DE (1) DE1273105B (de)
GB (1) GB1040992A (de)
NL (1) NL6505286A (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3767576A (en) * 1967-09-11 1973-10-23 Gen Electric Lubricating compositions containing halogen and alkoxy, acyloxy, or hydroxy groups
GB1241467A (en) * 1967-09-11 1971-08-04 Gen Electric Lubricating compositions containing halogen and alkoxy, acyloxy, or hydroxy groups
US4194886A (en) * 1974-04-09 1980-03-25 The Lubrizol Corporation Haloalkyl hydroxy-aromatic condensation products as fuel additives
US4179449A (en) * 1974-04-09 1979-12-18 The Lubrizol Corporation Haloalkyl hydroxy-aromatic condensation products as fuel and lubricant additives
US4108783A (en) * 1974-04-09 1978-08-22 The Lubrizol Corporation Haloalkyl hydroxy-aromatic condensation products as fuel and lubricant additives
IL77701A (en) * 1986-01-24 1988-11-30 Bromine Compounds Ltd Liquid flame retardants for hydraulic fluids

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2667505A (en) * 1951-11-09 1954-01-26 Us Rubber Co Alkyl esters of polyhalogenoalkenyl malonic acids
US2710877A (en) * 1952-06-05 1955-06-14 Exxon Research Engineering Co Synthetic lubricating composition
NL93256C (de) * 1954-04-13
US3081342A (en) * 1960-09-29 1963-03-12 Du Pont Fluoroalkyl esters

Also Published As

Publication number Publication date
NL6505286A (de) 1965-10-28
GB1040992A (en) 1966-09-01
US3260672A (en) 1966-07-12

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