DE896349C - Process for the preparation of lubricating oil improvers - Google Patents
Process for the preparation of lubricating oil improversInfo
- Publication number
- DE896349C DE896349C DEB18357A DEB0018357A DE896349C DE 896349 C DE896349 C DE 896349C DE B18357 A DEB18357 A DE B18357A DE B0018357 A DEB0018357 A DE B0018357A DE 896349 C DE896349 C DE 896349C
- Authority
- DE
- Germany
- Prior art keywords
- lubricating oil
- parts
- alkylphenol
- phosphorus pentasulfide
- preparation
- 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
Links
- 239000010687 lubricating oil Substances 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 4
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 150000002739 metals Chemical class 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 239000012084 conversion product Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 239000012188 paraffin wax Substances 0.000 description 4
- -1 B. oxides Chemical class 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 3
- 229940007718 zinc hydroxide Drugs 0.000 description 3
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 3
- YKMGCSOHXDDGAI-UHFFFAOYSA-N C(C(C)C)C12C(C=CC=C1)(O)S2 Chemical compound C(C(C)C)C12C(C=CC=C1)(O)S2 YKMGCSOHXDDGAI-UHFFFAOYSA-N 0.000 description 2
- AFPATFWRITWTFR-UHFFFAOYSA-N C(CCCC(C)C)C12C(C=CC=C1)(O)S2 Chemical compound C(CCCC(C)C)C12C(C=CC=C1)(O)S2 AFPATFWRITWTFR-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JNCGNNPCABQFGF-UHFFFAOYSA-N 2-(5-methylhexyl)phenol Chemical compound CC(C)CCCCC1=CC=CC=C1O JNCGNNPCABQFGF-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
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
- 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
- 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
- C07F9/04—Reaction products of phosphorus sulfur compounds with hydrocarbons
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
- C10M2223/121—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy of alcohols or phenols
-
- 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
-
- 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
- C10N2010/14—Group 7
-
- 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
- C10N2010/16—Groups 8, 9, or 10
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Lubricants (AREA)
Description
Verfahren zur Herstelluna von Schmierölve@rbesserungsmitteln Es ist bekannt, daß mehrwertige Metalle enthaltende Alkylphenole oder Alkylphenolsulfide gute Detergentwirkung haben, d. h. imstande sind, die Alterungsprodukte von Schmierölen im Motor in feiner Verteilung zu halten. Es ist ferner bekannt, daß man durch Einwirkung von Phosphorpentasulfid auf Hydroxydverbindungen gute Schmierölinhibitoren gewinnen kann.Process for the manufacture of lubricating oil improvers It is known that polyvalent metals containing alkylphenols or alkylphenol sulfides have good detergency d. H. are able to remove the aging products of lubricating oils to be kept in fine distribution in the engine. It is also known that by action obtain good lubricating oil inhibitors from phosphorus pentasulphide on hydroxide compounds can.
Es wurde nun gefunden, daß man Schmierölverbesserungsmittel erhält, die gleichzeitig Detergent-und Inhibitoreigenschaften besitzen, wenn man Alkylphenole, in denen mehrere Alkylphenolreste durch Brückenglieder miteinander verbunden sind, mit Phosphorpentasulfid in der Weise umsetzt, daß auf mindestens 8 Mol, vorteilhaft io bis 2o Mol, Alkylphenolrest nur etwa i Mol Phosphorpentasulfid kommt und in die Umsetzungsprodukte mehrwertige Metalle einführt. Als Alkylphenolverbindungenkommen solche in Frage, bei denen mehrere Alkylphenolreste durch Brückenglieder, wie -S-, -S2 oder -C H,-, miteinander verbunden sind. Auch Gemische verschiedener solcher Alkylphenolverbindungen können als Ausgangsstoffe dienen.It has now been found that lubricating oil improvers are obtained which have detergent and inhibitor properties at the same time, if one uses alkylphenols, in which several alkylphenol residues are linked by bridges, with phosphorus pentasulfide in such a way that at least 8 moles, advantageously 10 to 20 mol, alkylphenol radical only comes to about 1 mol of phosphorus pentasulfide and in the Implementation products of polyvalent metals. As alkylphenol compounds come those in question in which several alkylphenol radicals are bridged by bridges such as -S-, -S2 or -C H, -, are connected to one another. Also mixtures of different ones Alkylphenol compounds can serve as starting materials.
Auf mindestens 8 Mol Alkylphenolrest läßt man bei Temperaturen von etwa ioo bis 2oo°, vorteilhaft bei etwa i2o bis 15o°, etwa i Mol Phosphorpentasulfid einwirken. Durch die Verwendung von nur kleinen Mengen Phosphorpentasulfid wird die Bildung lästiger harzartiger Nebenprodukte vermieden. Die Einführung mehrwertiger Metalle in die Umsetzungsprodukte kann in der üblichen Weise geschehen. Man stellt z. B. Alkaliverbindungen her und gewinnt daraus durch doppelte Umsetzung mit alkoholischen Lösungen von Salzen der mehrwertigen Metalle die gewünschten Verbindungen. Besonders vorteilhaft ist es, die Umsetzungsprodukte durch Erhitzen mit basischen Verbindungen der mehrwertigen Metalle, z. B. Oxyden, Hydroxyden, Carbonaten oder Alkoholaten, direkt in die gewünschten Metallverbindungen überzuführen. Als Metalle kommen in erster Linie in Frage, Barium, Strontium, Calcium, Magnesium, Aluminium, Zink, Kobalt, Nickel und Zinn. Man kann auch mehrere Metalle gleichzeitig oder nacheinander in die erwähnten Umsetzungsprodukte einführen. Besonders gute Produkte erhält man, wenn man Erdalkalimetalle und Zink gleichzeitig einführt.At least 8 moles of alkylphenol residue is allowed to take place at temperatures of about 100 to 200 degrees, advantageously about 120 to 150 degrees, about 1 mole of phosphorus pentasulfide act. By using only small amounts of phosphorus pentasulphide avoid the formation of troublesome resinous by-products. Introducing more valued Metals in the reaction products can be done in the usual way. One poses z. B. alkali compounds and wins from them by double reaction with alcoholic Solutions of salts of polyvalent metals create the desired compounds. Particularly it is advantageous to use the reaction products by heating with basic Compounds of polyvalent metals, e.g. B. oxides, hydroxides, carbonates or Convert alcoholates directly into the desired metal compounds. As metals are primarily possible, barium, strontium, calcium, magnesium, aluminum, Zinc, cobalt, nickel and tin. You can also use several metals at the same time or one after the other introduce into the mentioned conversion products. Particularly good products are obtained if you introduce alkaline earth metals and zinc at the same time.
Die Schmierölverbesserungsmittel werden den Schmierölen in Mengen von etwa o,i bis etwa io °/o, vorteilhaft i bis 5 °/o, zugesetzt. Häufig ist es vorteilhaft, gleichzeitig noch schaumverhindernde Stoffe zuzugeben.The lubricating oil improvers are added to the lubricating oils in quantities from about 0.1 to about 10%, advantageously from 1 to 5%, added. Often it is It is advantageous to add foam-preventing substances at the same time.
Die im folgenden genannten Teile sind Gewichtsteile. Beispiel i Zu ioo Teilen Isobutylphenolsulfid gibt man bei i2o bis 15o° unter Rühren 12 Teile Phosphorpentasulfid. Nach Beendigung der Reaktion vermischt man mit Zoo Teilen Motorenschmieröl und filtriert heiß, wobei nur ganz wenig Unlösliches auf dem Filter bleibt. Zu dem Filtrat gibt man bei 13o° 3o Teile Zinkhydroxyd und erwärmt im Lauf i Stunde auf i5o°. Nach dem Filtrieren erhält man ein Produkt mit guten Detergent- und Inhibitoreigenschaften. Beispiel 2 Ein nach Beispiel i durch Umsetzung von Isobutylphenolsulfid mit Phosphorpentasulfid erhaltenes, mit Schmieröl verdünntes und filtriertes Produkt wird mit 6 Teilen Zinkhydroxyd und dann mit einer durch Erhitzen von io Teilen Calcium mit 3o Teilen Methanol erhaltenen Aufschlämmung von Calciummethylat in der Wärme behandelt. Nach dem Filtrieren und Abdestillieren des Methanols wird ein Schmierölzusatzstoff erhalten, durch den man Motorenschmieröle zu Hochleistungsschmierölen verbessern kann. ' Beispiel 3 Zu ioo Teilen Isoheptylphenolsulfid gibt man unter Rühren bei i2o° io Teile Phosphorpentasulfid und steigert die Temperatur langsam auf l40°. Nach Zugabe von Zoo Teilen Motorenschmieröl filtriert man heiß und behandelt das Filtrat bei 13o bis 14o° mit 8o Teilen Ba (0 H)?, - 8 HZ 0. Durch Filtrieren oder Zentrifugieren erhält man ein Schmierölzusatzmittel mit Detergent-und Inhibitoreigenschaften. Verwendet man statt Isoheptylphenolsulfid 93 Teile Isoheptylphenol, so erhält man ein ähnlich wirkendes Produkt. Beispiel q. ioo Teile Paraffinalkylphenoldisulfid, das durch Einwirkung von S,Ch auf das Umsetzungsprodukt von chloriertem Paraffin mit Phenol gewonnen wurde, werden in der in Beispiel i beschriebenen Weise mit 5 Teilen Phosphorpentasulfid und dann mit 12 Teilen Zinkhydroxyd behandelt. Man erhält ein Schmierölverbesserungsmittel mit ausgezeichneten Detergenteigenschaften, das auch Inhibitoreigenschaften hat. Ein ähnlich wirkendes Produkt erhält man, wenn man statt Paraffinalkylphenoldisulfid 95 Teile Paraffinalkylphenol verwendet.The following parts are parts by weight. EXAMPLE i To 100 parts of isobutylphenol sulfide are added 12 parts of phosphorus pentasulfide at from 120 to 150 ° with stirring. After the reaction has ended, it is mixed with Zoo parts of engine lubricating oil and filtered hot, with very little insolubles remaining on the filter. To the filtrate are added 30 parts of zinc hydroxide at 130 ° and heated to 150 ° in the course of one hour. After filtration, a product with good detergent and inhibitor properties is obtained. EXAMPLE 2 A product obtained according to Example i by reacting isobutylphenol sulfide with phosphorus pentasulfide, diluted with lubricating oil and filtered, is treated with 6 parts of zinc hydroxide and then with a slurry of calcium methylate obtained by heating 10 parts of calcium with 3o parts of methanol. After filtering and distilling off the methanol, a lubricating oil additive is obtained which can be used to improve engine lubricating oils to high-performance lubricating oils. EXAMPLE 3 To 100 parts of isoheptylphenol sulfide are added, with stirring, at 120 °, 10 parts of phosphorus pentasulfide, and the temperature is slowly increased to 140 °. After adding zoo parts of engine lubricating oil, the mixture is filtered hot and the filtrate is treated at 130 to 14 ° with 80 parts of Ba (0 H)?, - 8 HZ 0. A lubricating oil additive with detergent and inhibitor properties is obtained by filtering or centrifuging. If 93 parts of isoheptylphenol are used instead of isoheptylphenol sulfide, a product with a similar effect is obtained. Example q. 100 parts of paraffin alkylphenol disulfide, which was obtained by the action of S, Ch on the reaction product of chlorinated paraffin with phenol, are treated in the manner described in Example i with 5 parts of phosphorus pentasulfide and then with 12 parts of zinc hydroxide. A lubricating oil improver is obtained which has excellent detergent properties and which also has inhibitory properties. A similarly acting product is obtained if 95 parts of paraffin alkyl phenol are used instead of paraffin alkyl phenol disulfide.
Claims (2)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB18357A DE896349C (en) | 1951-12-25 | 1951-12-25 | Process for the preparation of lubricating oil improvers |
| DEB28220A DE941125C (en) | 1951-12-25 | 1953-11-04 | Process for the preparation of lubricating oil improvers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB18357A DE896349C (en) | 1951-12-25 | 1951-12-25 | Process for the preparation of lubricating oil improvers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE896349C true DE896349C (en) | 1953-11-12 |
Family
ID=6959719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB18357A Expired DE896349C (en) | 1951-12-25 | 1951-12-25 | Process for the preparation of lubricating oil improvers |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE896349C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE941125C (en) * | 1951-12-25 | 1956-04-05 | Basf Ag | Process for the preparation of lubricating oil improvers |
-
1951
- 1951-12-25 DE DEB18357A patent/DE896349C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE941125C (en) * | 1951-12-25 | 1956-04-05 | Basf Ag | Process for the preparation of lubricating oil improvers |
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