DE1269118B - Process for improving the properties of high-performance lubricants used diester lubricating oils - Google Patents
Process for improving the properties of high-performance lubricants used diester lubricating oilsInfo
- Publication number
- DE1269118B DE1269118B DEP1269A DE1269118A DE1269118B DE 1269118 B DE1269118 B DE 1269118B DE P1269 A DEP1269 A DE P1269A DE 1269118 A DE1269118 A DE 1269118A DE 1269118 B DE1269118 B DE 1269118B
- Authority
- DE
- Germany
- Prior art keywords
- properties
- improving
- lubricating oils
- carbon
- performance lubricants
- 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
Links
Classifications
-
- 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/36—Esters of polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- 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
- C10N2020/02—Viscosity; Viscosity index
-
- 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
- C10N2020/071—Branched chain compounds
-
- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/02—Pour-point; Viscosity index
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
- C10N2040/13—Aircraft turbines
-
- 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
- C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
-
- 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
- C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
- C10N2060/09—Treatment with nitrogen containing compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
Description
Wenn man vergleichsweise niedermolekulare Di- Verfahren zur Verbesserung der EigenschaftenIf one compares comparatively low molecular weight Di- Method to improve the properties
carbonsäuren mit — vorzugsweise verzweigten — pri- von Hochleistungsschmierstoffe dienendencarboxylic acids with - preferably branched - pri- of high-performance lubricants
mären Alkoholen verestert, erhält man, insbesondere Diester-Schmierölen
für Turbinentriebwerke, geeignete Schmiermittel. Sie
zeichnen sich durch Beständigkeit in der Kälte und 5Esterified alcohols are obtained, especially diester lubricating oils
for turbine engines, suitable lubricants. she
are characterized by resistance to the cold and 5
bei hohen Temperaturen, vorzügliche Schmierwirkung at high temperatures, excellent lubricating effect
und gutes Viskositäts-Temperatur-Verhalten aus. Alle Anmelderderartigen Ester besitzen jedoch den Nachteil, daß sie and good viscosity-temperature behavior. However, all applicant-type esters have the disadvantage that they
Dichtungsmaterialien stark anquellen und sogar auf- Technochemie G. m. b. H. Verfahrenstechnik,Sealing materials swell strongly and even up- Technochemie G. m. B. H. Process engineering,
lösen. Trotz der erwähnten Vorzüge sind sie daher io 6900 Heidelberg, Heiligenbergstr. 1 bto solve. Despite the advantages mentioned, they are therefore io 6900 Heidelberg, Heiligenbergstr. 1 b
schwer verwendbar. difficult to use.
Mit steigender Länge der Kohlenstoffkette der Di- ^ Erfmder With increasing length of the carbon chain of the Di- ^ Erfmder
carbonsauren nimmt dieses nachteilige Verhalten ab, . .carboxylic acids reduce this disadvantageous behavior,. .
so daß schließlich bei einer Kohlenstoffzahl von 19 in Dr·Herbert Petrovicki, 6900 Heidelberg;so that finally with a carbon number of 19 in Dr. Herbert Petrovicki, 6900 Heidelberg;
den Dicarbonsäuren die Ester sich ähnlich wie Mineral- 15 Dr. Othmar Pauer, 5302 Beuel;to the dicarboxylic acids, the esters are similar to mineral 15 Dr. Othmar Pauer, 5302 Beuel;
ölprodukte verwenden lassen. Solche Dicarbonsäuren Dr. Kurt Kirsch, 6901 Dossenheimlet use oil products. Such dicarboxylic acids Dr. Kurt Kirsch, 6901 Dossenheim
sind z. B. erhältlich, wenn man in Gegenwart saurer are z. B. available when acidic in the presence
Katalysatoren, wie Schwefelsäure, unter Druck anCatalysts, such as sulfuric acid, under pressure
Ölsäure Kohlenoxid anlagert (vgl. »Brennstoffchemie«, 2
Bd. 36, S. 321 bis 328 [1955]; »Annalen der Chemie«, 20Oleic acid accumulates carbon oxide (cf. »Fuel Chemistry«, 2
Vol. 36, pp. 321 to 328 [1955]; »Annals of Chemistry«, 20
Bd. 618, S. 251 bis 266 [1958], und »Fette, Seifen, beiden Mitteln unterwirft. Unter »basischem Alumi-Vol. 618, pp. 251 to 266 [1958], and “Fette, Seifen, both means subject. Under »basic aluminum
Anstrichmittel«, Bd. 59, S. 493 bis 498 [1957]. Ein niumoxid« ist ein Produkt zu verstehen, dessen wäßrigePaints ", Vol. 59, pp. 493 to 498 [1957]. A "niumoxid" is to be understood as a product, its aqueous
solcherart erhaltenes technisches Gemisch aus Di- Suspension einen pH-Wert von etwa 10 aufweist. EsTechnical mixture of di-suspension obtained in this way has a pH of about 10. It
carbonsäuren mit durchschnittlich 19 Kohlenstoff- wird gewonnen durch Erhitzen von technischem, mitcarboxylic acids with an average of 19 carbon- is obtained by heating technical, with
atomen zeigt nach der Destillation die folgenden 25 Alkalilauge gefälltem Aluminiumhydroxid auf 250 bisatoms shows the following 25 alkali metal precipitated aluminum hydroxide to 250 to after the distillation
Eigenschaften bzw. Kennzahlen 4000C (Ullmanns Enzyklopädie der technischen Che-Properties or key figures 400 0 C (Ullmann's encyclopedia of technical
Viskosität 1^' 4· Auflage, Bd. II, 1, S. 107, 1961).Viscosity 1 ^ ' 4 · Edition, Vol. II, 1, p. 107, 1961).
bei 50° C 842 8 cSt -^as erfindungsgemäße Verfahren zur Verbesserungat 50 ° C 842 8 cSt - ^ as inventive method for improvement
bei 98°C 6l'l cSt ^er Eigenschaften von als Hochleistungsschmierstoffeat 98 ° C 6l'l cSt ^ er properties of as high-performance lubricants
Viskositätsindex 76 3° dienenden Diester-Schmierölen, die durch VeresternViscosity index 76 3 ° serving diester lubricating oils, which by esterification
Stockpunkt -15 50C von durchschnittlich 19 Kohlenstoffatome enthal-Contained pour point -15 5 0 C by an average of 19 carbon atoms
Säurezahl .................... 335' tenden, durch Anlagerung von Kohlenoxid an ÖlsäureAcid number .................... 335 'tendency, due to the addition of carbon oxide to oleic acid
erhältlichen Dicarbonsäuregemischen mit mindestensavailable dicarboxylic acid mixtures with at least
Durch Veresterung dieses Dicarbonsäuregemisches 6 Kohlenstoffatomen enthaltenden einwertigen ver-By esterifying this dicarboxylic acid mixture containing 6 carbon atoms, monovalent
mit Isononylalkohol aus der Oxosynthese in Gegen- 35 zweigten Alkoholen hergestellt werden, ist dadurchare produced with isononyl alcohol from the oxo synthesis in counter-branched alcohols, is thereby
wart von Schwefelsäure als Katalysator erhält man gekennzeichnet, daß man sie einer Behandlung mitwart of sulfuric acid as a catalyst is obtained characterized in that it is treated with
nach der Destillation bei 250° C/0,55 mm einen Misch- Harnstoff und bzw. oder mit Aktivkohle und »ba-after the distillation at 250 ° C / 0.55 mm a mixed urea and / or with activated carbon and »ba
ester mit folgenden Kennzahlen sischem Aluminiumoxid« unterwirft.ester with the following key figures sic aluminum oxide «.
Viskositätviscosity
bei 5O0C 28,6 cSt 4° B e i s ρ i e 1 1at 50 0 C 28.6 cSt 4 ° B eis ρ ie 1 1
bei 980C 6,67cSt ^-1 _ __ J ,. ,at 98 0 C 6.67cSt ^ -1 _ __ J,. ,
Viskositätsindex . 108 2000 Gewichtsteile Heptadecandicarbonsaure-dnso-Viscosity index. 108 2000 parts by weight of heptadecanedicarboxylic acid-dnso-
Stockpunkt —61 5° C nonylester werden in 1400 Raumteilen MethylenchloridPour point -61 5 ° C nonyl esters become methylene chloride in 1400 parts by volume
Säurezahl . . . '. 6Ί gelöst und unter Rückfluß erhitzt. Dann läßt manAcid number . . . '. 6Ί dissolved and heated under reflux. Then one lets
45 unter Rühren eine heiße Lösung von 1000 Teilen45 a hot solution of 1000 parts with stirring
Dieser Ester zeigt im Vergleich zu anderen, z. B. Harnstoff in 1400 Raumteilen Methylenchlorid so zuaus Sebacinsäure gewonnenen, ein unbefriedigendes fließen, daß das Gemisch immer unter Rückfluß siedet. Viskositäts-Temperatur-Verhalten. Danach wird langsam während mehrerer Stunden Es wurde nun gefunden, daß man solche Ester auf Raumtemperatur abgekühlt, das Gemisch von wesentlich verbessern kann, wenn man sie einer Be- 50 festen Anteilen durch Schleudern oder Filtrieren behandlung mit Harnstoff oder mit einem Gemisch aus freit und der Rückstand zweimal mit je 200 Raum-Aktivkohle und »basischem Aluminiumoxid« oder teilen Methylenchlorid gewaschen. Das Filtrat wirdThis ester shows in comparison to others, e.g. B. urea in 1400 parts by volume of methylene chloride so zuaus Sebacic acid obtained, an unsatisfactory flow that the mixture always refluxes. Viscosity-temperature behavior. It is then slowly carried out for several hours. It has now been found that such esters can be cooled to room temperature, the mixture of It can be improved significantly if it is treated with 50 solid parts by centrifuging or filtering with urea or with a mixture of freit and the residue twice with 200 space activated carbon each time and "basic alumina" or partially washed methylene chloride. The filtrate will
11
bis zu einer Sumpftemperatur von 8O0C eingedampft, mit 3000 Raumteilen Wasser versetzt und angesäuert (pH = 3 bis 5). Nach dem Abtrennen der wäßrigen Phase und Neutralwaschen mit Wasser wird die organische Phase durch azeotrope Destillation mit Benzol 5 als Schleppmittel vom Rest des Wassers befreit und bis zu einer Sumpftemperatur von 1300C bei 1mm destilliert. Nach dieser Behandlung zeigt der Ester folgende Kennzahlenup to a bottom temperature of 8O 0 C evaporated, mixed with 3000 parts by volume of water and acidified (pH = 3 to 5). After separation of the aqueous phase and neutral washing with water, the organic phase is removed by azeotropic distillation with benzene as an entrainer 5 from the rest of the water and distilled to a pot temperature of 130 0 C at 1mm. After this treatment, the ester shows the following key figures
Viskositätviscosity
bei 500C 28,8 cStat 50 ° C 28.8 cSt
bei98°C 7,64 cStat 98 ° C 7.64 cSt
Viskositäfsindex 132Viscosity Index 132
Stockpunkt -580CPour point -58 0 C
Säurezahl 6Acid number 6
Das Viskositäts-Temperatur-Verhalten ist also wesentlich verbessert.The viscosity-temperature behavior is therefore essential improved.
Wenn man statt Harnstoff Aktivkohle und »basisches Aluminiumoxid« verwendet, erzielt man eine Verbesserung sowohl hinsichtlich des Viskositätsindex als auch des Säuregehaltes und der Farbe, wie das folgende Beispiel zeigt.If you use activated carbon and "basic aluminum oxide" instead of urea, you get one Improvement in both viscosity index and acidity and color, like that the following example shows.
Zu 1000 Teilen Heptadecandicarbonsäure-diisononylester gibt man 20 Teile Aktivkohle und 20 Teile »basisches Aluminiumoxid« und erwärmt das Gemisch unter Rühren etwa 2 Stunden auf 6O0C. Nach demTo 1000 parts heptadecanedicarboxylic-diisononyl esters are added 20 parts of carbon and 20 parts "basic alumina" and the mixture heated with stirring for about 2 hours at 6O 0 C. After
118118
Abfiltrieren der festen Anteile zeigt der Ester die folgenden KennzahlenFiltering off the solid fractions, the ester shows the following Key figures
Viskositätviscosity
bei50°C 27,5 cStat 50 ° C 27.5 cSt
bei98°C 7,34 cStat 98 ° C 7.34 cSt
Viskositätsindex 131Viscosity Index 131
Stockpunkt -610CPour point -61 0 C
Säurezahl 2,6Acid number 2.6
Man kann die Behandlung auch durch Perkolieren einer mit den genannten Mitteln gefüllte Säule ausführen. Ebenso kann man die beiden Behandlungsweisen, also die mit Harnstoff und die mit dem Gemisch aus Aktivkohle und »basischem Aluminiumoxid«, kombinieren.The treatment can also be carried out by percolating a column filled with the agents mentioned. You can also use the two methods of treatment, i.e. the one with urea and the one with the mixture of activated carbon and "basic aluminum oxide".
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP1269A DE1269118B (en) | 1964-07-30 | 1964-07-30 | Process for improving the properties of high-performance lubricants used diester lubricating oils |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP1269A DE1269118B (en) | 1964-07-30 | 1964-07-30 | Process for improving the properties of high-performance lubricants used diester lubricating oils |
| DET0026698 | 1964-07-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1269118B true DE1269118B (en) | 1968-05-30 |
Family
ID=25751125
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP1269A Pending DE1269118B (en) | 1964-07-30 | 1964-07-30 | Process for improving the properties of high-performance lubricants used diester lubricating oils |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1269118B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007082639A1 (en) * | 2006-01-12 | 2007-07-26 | Cognis Ip Management Gmbh | Use of esters comprising branched alkyl groups as lubricants |
-
1964
- 1964-07-30 DE DEP1269A patent/DE1269118B/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007082639A1 (en) * | 2006-01-12 | 2007-07-26 | Cognis Ip Management Gmbh | Use of esters comprising branched alkyl groups as lubricants |
| US8921289B2 (en) | 2006-01-12 | 2014-12-30 | Cognis Ip Management Gmbh | Esters comprising branched alkyl groups as lubricants |
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