DE1018428B - Process for the preparation of lubricating oil improvers - Google Patents
Process for the preparation of lubricating oil improversInfo
- Publication number
- DE1018428B DE1018428B DEB29851A DEB0029851A DE1018428B DE 1018428 B DE1018428 B DE 1018428B DE B29851 A DEB29851 A DE B29851A DE B0029851 A DEB0029851 A DE B0029851A DE 1018428 B DE1018428 B DE 1018428B
- Authority
- DE
- Germany
- Prior art keywords
- lubricating oil
- alkaline earth
- parts
- water
- phosphorus pentasulfide
- 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
- 238000000034 method Methods 0.000 title claims description 3
- 239000010687 lubricating oil Substances 0.000 title description 12
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 150000004679 hydroxides Chemical class 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims 1
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 239000000314 lubricant Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- FIWYWGLEPWBBQU-UHFFFAOYSA-N 2-heptylphenol Chemical compound CCCCCCCC1=CC=CC=C1O FIWYWGLEPWBBQU-UHFFFAOYSA-N 0.000 description 4
- -1 alkaline earth metal salts Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000010705 motor oil Substances 0.000 description 4
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- WCRKLZYTQVZTMM-UHFFFAOYSA-N 2-octadecylphenol Chemical compound CCCCCCCCCCCCCCCCCCC1=CC=CC=C1O WCRKLZYTQVZTMM-UHFFFAOYSA-N 0.000 description 1
- MEEKGULDSDXFCN-UHFFFAOYSA-N 2-pentylphenol Chemical compound CCCCCC1=CC=CC=C1O MEEKGULDSDXFCN-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 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
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 230000001236 detergent effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 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
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent 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
- 150000004763 sulfides Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
Classifications
-
- 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
- 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
- C10M137/10—Thio derivatives
- C10M137/105—Thio derivatives not containing metal
-
- 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
- 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
- C10M2207/028—Overbased salts thereof
-
- 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
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. 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
-
- 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
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
Description
Verfahren zur Herstellung von Schmierölverbesser ungsmitteln Es ist bekannt, Schmierölverbesserungsmittel mit Detergent- und Inhibitorwirkung herzustellen, indem man Alkylphenole mit Phosphorpentasülfid im Molverhältnis von mindestens 8: 1 umsetzt und in die Umsetzungsprodukte ein oder mehrere Erdalkalimetalle und Zink einführt.Process for making lubricating oil improvers It is known to produce lubricating oil improvers with detergent and inhibitory effects, by using alkylphenols with phosphorus pentasulfide in a molar ratio of at least 8: 1 converts and in the reaction products one or more alkaline earth metals and zinc introduces.
Es wurde nun gefunden, daß man auch ohne Mitverwendung von verhältnismäßig teueren Zinkverbindungen ebenso wirksame und sogar noch wirksamere Schmierölverbesserungsmittel erhält, wenn man Alkylphenole mit Phosphorpentasulfid im Verhältnis von mindestens 8, vorteilhaft 1.0 oder 12 Mol Alkylphenol zu 1 Mol Phosphorpentasulfid umsetzt und die sauren Reaktionsprodukte durch Behandlung mit überschüssigen Erdalkalioxyden oder -hydroxyden in alkalisch reagierende Erdalkalisalze, vorteilhaft in solche, die mehrere Erdalkalimetalle enthalten, überführt, wobei man mindestens gegen Ende der Behandlung unter Zu-2n von Wasser und/oder Alkohol arbeitet.It has now been found that, even without using relatively expensive zinc compounds, equally effective and even more effective lubricating oil improvers are obtained if alkylphenols are reacted with phosphorus pentasulfide in a ratio of at least 8, advantageously 1.0 or 12 moles of alkylphenol to 1 mole of phosphorus pentasulfide and the acidic reaction products through Treatment with excess alkaline earth oxides or hydroxides is converted into alkaline alkaline earth metal salts, advantageously into those containing several alkaline earth metals, with the addition of water and / or alcohol at least towards the end of the treatment.
Als Alkylphenole verwendet man mit Vorteil solche, die mindestens eine gerade oder verzweigte Kette mit mindestens 4 Kohlenstoffatomen enthalten, z. B. Butylphenol, Dibutylkresol, 'Amylphenol, Heptylphenol, Dodecylphenol, Octadecylphenol oder Gemische dieser Stoffe. Geeignete Alkylphenole sind auch solche, die man durch Alkylierung von Phenolen mit chlorierten Fraktionen von Erdöl oder synthetisch, z. B. aus Kohlenoxyd und Wasserstoff, hergestellten Kohlenwasserstoffgemischen oder mit chlorierten Paraffinen oder mit Olefinen erhält.The alkylphenols used with advantage are those which have at least contain a straight or branched chain with at least 4 carbon atoms, z. B. butylphenol, dibutyl cresol, amylphenol, heptylphenol, dodecylphenol, octadecylphenol or mixtures of these substances. Suitable alkylphenols are also those that can be through Alkylation of phenols with chlorinated fractions of petroleum or synthetic, z. B. from carbon oxide and hydrogen, produced hydrocarbon mixtures or obtained with chlorinated paraffins or with olefins.
Man läßt das Phosphorpentasulfid auf die Alkylphenole bei erhöhter Temperatur einwirken, die nicht über 100° zu liegen braucht, in der Regel jedoch bei Temperaturen über 100°, insbesondere bei 130 bis 180° oder höher, z. B. bei 200 bis 250°. Es ist vorteilhaft, Mischungen verschiedener Phosphorpentasulfid-Umsetzungsprodukte, die unter sonst gleichen Bedingungen bei verschiedener Temperatur hergestellt wurden, zu verwenden, wodurch in weitem Temperaturbereich günstige Korrosionsschutzwirkung erzielt wird.The phosphorus pentasulphide is left on the alkylphenols at elevated levels Acting at a temperature that does not need to be above 100 °, as a rule, however at temperatures above 100 °, in particular at 130 to 180 ° or higher, e.g. B. at 200 to 250 °. It is advantageous to use mixtures of different phosphorus pentasulphide reaction products, which were produced under otherwise identical conditions at different temperatures, to be used, whereby a favorable corrosion protection effect in a wide temperature range is achieved.
Auf die bekannten Phosphorpentasulfid-Umsetzungspredukte der Alkylphenole und die mit ihnen vermischten, nicht umgesetzten Alkylphenole läßt man Oxyde oder Hydroxyde von Calcium, Strontium, Barium oder Magnesium in solchem Überschuß einwirken, daß alkalisch reagierende Salze erhalten werden. Die hierfür notwendige Menge läßt sich durch Vorversuche leicht ermitteln oder berechnen. Um alkalisch reagierende Salze zu erhalten, ist es notwendig, mindestens gegen Ende der Einwirkung der Oxyde oder I1ydroxyde für die Gegenwart von Wasser und/oder Alkoholen zu sorgen. Es genügt zu diesem Zweck, einen Bruchteil bis zu einem Mehrfachen der angewandten Menge Metalloxyd an Wasser oder Alkohol, z. B. die gleiche Gewichtsmenge: Wasser oder die doppelte Gewichtsmenge Methylalkohol, zuzusetzen.On the well-known phosphorus pentasulphide conversion products of the alkylphenols and the unreacted alkylphenols mixed with them are left oxides or Hydroxides of calcium, strontium, barium or magnesium act in such excess, that alkaline salts are obtained. The amount necessary for this leaves can be easily determined or calculated through preliminary tests. To be alkaline To obtain salts it is necessary at least towards the end of the action of the oxides or hydroxides to ensure the presence of water and / or alcohols. It is sufficient for this purpose, a fraction to a multiple of the amount of metal oxide used of water or alcohol, e.g. B. the same amount by weight: water or twice that amount Amount by weight of methyl alcohol to be added.
Die so erhaltenen Stoffe sind öllöslich und bewirken, schon in Mengen von weniger als 1% einem Motorenschmieröl zugesetzt, eine wesentliche Verbesserung hinsichtlich der Oxydationsbeständigkeit. Verwendet man etwa 1% oder mehr davon, so erhalten die Motorenöle die Eigenschaften von Hochleistungsölen. Sie verhindern Oxydation und Korrosion und wirken als Detergents.The substances obtained in this way are oil-soluble and have an effect, even in large quantities less than 1% added to an engine lubricating oil, a significant improvement in terms of resistance to oxidation. If you use about 1% or more of it, this gives the engine oils the properties of high-performance oils. You prevent Oxidation and corrosion and act as detergents.
Ein besonderer Vorteil der Schmierölverbesserungsmittel nach der Erfindung besteht darin, daß sie sich mit anderen Schmierölverbesserungsmitteln ohne weiteres mischen lassen und mit diesen zusammen eine besondere Wirkung hervorrufen. So kann man sie z. B. mit den nach dem Patent 843 281 erhältlichen Stoffen sowie mit entsprechenden Metallverbindungen nicht veresterter Alkylphenolsulfide oder mit Mischungen, die diese Stoffe enthalten, zusammen verwenden. Sie vertragen sich auch gut mit Metallsulfona,ten und deren Mischungen mit metallhaltigen öllöslichen Phosphorsulfid-Umsetzungsprodukten von Alkoholen, Alkylphenolen, Olefinen oder Aminen. Auch zusammen mit Umsetzungsprodukten von Phosphorsulfiden mit Sulfonsäuren und mit deren von mehrwertigen Metallen abgeleiteten Salzen können sie verwendet werden.A particular advantage of the lubricating oil improvers of the invention is that they easily interact with other lubricating oil improvers let mix and together with these produce a special effect. So can you z. B. with the substances available according to the patent 843 281 and with the corresponding Metal compounds of non-esterified alkylphenol sulfides or with mixtures that contain contain these substances, use together. They also get along well with metal sulfonates and their mixtures with metal-containing oil-soluble phosphorus sulfide reaction products of alcohols, alkylphenols, olefins or amines. Also together with implementation products of phosphorus sulphides with sulphonic acids and those derived from polyvalent metals Salts they can be used.
Die in den folgenden Beispielen angegebenen Teile sind Gewichtsteile.The parts given in the following examples are parts by weight.
Beispiel 1 100 Teile Heptylphenol werden 1 Stunde am Rückflußkühler mit 12 Teilen Phosphorpentasulfid auf 240° erhitzt. Wenn kein Schwefelwasserstoff mehr entweicht, wird das Unlösliche abfiltriert und das Umsetzungsprodukt mit 200 Teilen Motorenöl vermischt. Hierauf gibt man bei 130° allmählich 65 Teile Ba (0H)2 - 8H20 zu und hält die Temperatur auf dieser Höhe, bis kein Wasser mehr entweicht. Nach kurzem Erhitzen auf 180° wird filtriert und auf 70° gekühlt. Hierauf setzt man 15 Teile Calciumoxy d zu, die mit 15 Teilen Wasser und mit 30 Teilen Methanol vermischt sind. Nach 1stündigem Erhitzen am Rückflußkühler destilliert man unter Steigerung der Temperatur auf 150° Methanol und Wasser ab und filtriert das Produkt. Dieses ist, wie die Einwirkung von Phenolphthalein auf einen Methanolauszug zeigt, alkalisch.Example 1 100 parts of heptylphenol are refluxed for 1 hour heated to 240 ° with 12 parts of phosphorus pentasulfide. If no hydrogen sulfide more escapes, the insoluble is filtered off and the reaction product with 200 parts of motor oil mixed. 65 parts of Ba are then gradually added at 130 ° (0H) 2 - 8H20 and maintains the temperature at this level until no more water escapes. After brief heating to 180 °, it is filtered and cooled to 70 °. Relies on this 15 parts of calcium oxide are added to 15 parts of water and 30 parts of methanol are mixed. After 1 hour of heating on the reflux condenser, the mixture is distilled under Increase the temperature to 150 ° methanol and water and filter the product. This is, as the action of phenolphthalein on a methanol extract shows, alkaline.
2 bis 4% des so gewonnenen Stoffes geben einem Motorenöl die Eigenschaften eines Hochleistungsschmieröles. Ein solches Öl erhöht die Reinheit eines Dieselmotors noch etwas stärker als das gleiche t51 mit der entsprechenden Menge eines nach Beispiel 1 des Patents 914 007 (Anmeldung B 22104 IV c/ 12 q) hergestellten Schmierölzusa,tzstoffes.2 to 4% of the material obtained in this way gives an engine oil the properties of a high-performance lubricating oil. Such an oil increases the purity of a diesel engine somewhat more than the same t51 with the corresponding amount of a lubricating oil additive produced according to example 1 of patent 914 007 (application B 22104 IV c / 12 q).
Verwendet man bei der Behandlung mit Calciumoxyd statt Methanol die entsprechende Menge Wasser, so erhält man ein Produkt von ähnlicher Beschaffenheit. Beispiel 2 Die im Beispiel 1 beschriebene bekannte Behandlung von Heptylphenol mit Phosphorpentasulfid wird unter Beibehaltung der übrigen Arbeitsbedingungen bei 180° durchgeführt. Man erhält einen Stoff, der, in Mengen von 2 bis 4% einem Schmieröl zugesetzt, auf den Kupfer-Bronze-Lagern von Verbrennungsmotoren eine dunkelgefärbte korrosionsverhindernde Schutzschicht verursacht. Eine gute schmierölverbessernde Wirkung wird auch erreicht, wenn man die Produkte nach Beispiel 1 und 2 im Gemisch miteinander, z. B. im Verhältnis von 2:1 bis 1:2, zur Verbesserung von Schmierölen verwendet.If the treatment with calcium oxide is used instead of methanol a corresponding amount of water gives a product of a similar nature. Example 2 The known treatment of heptylphenol described in Example 1 with Phosphorus pentasulphide is used while maintaining the remaining working conditions at 180 ° carried out. A substance is obtained which, in amounts of 2 to 4%, is a lubricating oil added, a dark-colored on the copper-bronze bearings of internal combustion engines corrosion-preventing protective layer caused. A good lubricating oil improver Effect is also achieved if the products according to Example 1 and 2 are mixed together with each other, e.g. B. in the ratio of 2: 1 to 1: 2, to improve lubricating oils used.
Beispiel 3 Das nach Beispiel 1 hergestellte Umsetzungsprodukt von Heptylphenol mit Phosphorpentasulfid wird filtriert, mit Motorenöl gemischt und bei 130° mit 75 Teilen Ba (O H) 2 - 8 H2 O versetzt. Nach kurzen Erhitzen auf 180° läßt man abkühlen und erwärmt dann 1 Stunde mit 30 Teilen Methanol am Rückflußkühler. Das vom Lösungsmittel befreite Produkt wird heiß filtriert und hat dann ähnliche Eigenschaften wie der nach Beispiel 1 gewonnene Stoff. Ähnlich wirkende Verbindungen erhält man, wenn man Methanol durch entsprechende Mengen Äthanol oder Propanol ersetzt, Beispiel 4 11 Teile Dodecylphenol werden bei 200' mit einem Teil Phosphorpentasulfid behandelt. Nach dem Filtrieren in der Hitze mischt man 15 Teile Mineralöl zu und erhitzt allmählich auf 130° unter Zugabe von 6 Teilen Ba (O H)2 - 8 H., O. Nach Beendigung des Schäumens wird kurz auf 180° erhitzt, filtriert und 1 Stunde mit 1 Teil Magnesiumo_xyd und 1 Teil Wasser am Rückflußkühler erhitzt. Nach dem Entfernen des Wassers wird bei 150° filtriert. Das Pro-Bukt ist ein ausgezeichnetes Schtnierölverbesserungsmittel.Example 3 The reaction product of Heptylphenol with phosphorus pentasulfide is filtered, mixed with engine oil and 75 parts of Ba (O H) 2-8 H2 O were added at 130 °. After brief heating to 180 ° allowed to cool and then heated for 1 hour with 30 parts of methanol in a reflux condenser. The product freed from the solvent is filtered hot and then has similar Properties like the substance obtained according to Example 1. Similar acting connections is obtained by replacing methanol with appropriate amounts of ethanol or propanol, Example 4 11 parts of dodecylphenol are mixed at 200 'with one part of phosphorus pentasulfide treated. After filtering in the heat, 15 parts of mineral oil are mixed in and gradually heated to 130 ° with the addition of 6 parts of Ba (O H) 2-8 H., O. Nach End of foaming is briefly heated to 180 °, filtered and 1 hour with 1 part magnesium oxide and 1 part water heated on the reflux condenser. After removing the water is filtered at 150 °. The Pro-Bukt is an excellent stamping oil improver.
Verwendet man statt Dodecy lphenol 18 Teile Paraffinalkylphenol, das aus chloriertem Paraffin und Phenol in Gegenwart von Aluminiumchlorid gewonnen wurde, so erhält man ähnliche Produkte.If you use 18 parts of paraffin alkyl phenol instead of dodecyl phenol, the obtained from chlorinated paraffin and phenol in the presence of aluminum chloride, so you get similar products.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB29851A DE1018428B (en) | 1954-02-23 | 1954-02-23 | Process for the preparation of lubricating oil improvers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB29851A DE1018428B (en) | 1954-02-23 | 1954-02-23 | Process for the preparation of lubricating oil improvers |
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| Publication Number | Publication Date |
|---|---|
| DE1018428B true DE1018428B (en) | 1957-10-31 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB29851A Pending DE1018428B (en) | 1954-02-23 | 1954-02-23 | Process for the preparation of lubricating oil improvers |
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| Country | Link |
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| DE (1) | DE1018428B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1986005492A1 (en) * | 1985-03-12 | 1986-09-25 | The Lubrizol Corporation | Metal salts of hydrocarbyl substituted aromatic phosphorodithioic acids |
-
1954
- 1954-02-23 DE DEB29851A patent/DE1018428B/en active Pending
Non-Patent Citations (1)
| Title |
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| None * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1986005492A1 (en) * | 1985-03-12 | 1986-09-25 | The Lubrizol Corporation | Metal salts of hydrocarbyl substituted aromatic phosphorodithioic acids |
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