EP0007257B1 - Procédé de préparation de détergents-dispersants de haute alcalinité pour huiles lubrifiantes et produit obtenu - Google Patents
Procédé de préparation de détergents-dispersants de haute alcalinité pour huiles lubrifiantes et produit obtenu Download PDFInfo
- Publication number
- EP0007257B1 EP0007257B1 EP79400376A EP79400376A EP0007257B1 EP 0007257 B1 EP0007257 B1 EP 0007257B1 EP 79400376 A EP79400376 A EP 79400376A EP 79400376 A EP79400376 A EP 79400376A EP 0007257 B1 EP0007257 B1 EP 0007257B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- weight
- parts
- alkylbenzenesulphonate
- magnesium
- alkylphenol
- 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
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims abstract description 22
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000003513 alkali Substances 0.000 title 1
- 239000003795 chemical substances by application Substances 0.000 title 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 73
- 239000011575 calcium Substances 0.000 claims abstract description 71
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 68
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 67
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 67
- 239000000203 mixture Substances 0.000 claims abstract description 62
- 239000011777 magnesium Substances 0.000 claims abstract description 58
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 52
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 43
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000000395 magnesium oxide Substances 0.000 claims abstract description 30
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims abstract description 28
- -1 alkylene glycol Chemical compound 0.000 claims abstract description 23
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 19
- 235000008733 Citrus aurantifolia Nutrition 0.000 claims abstract description 9
- 235000011941 Tilia x europaea Nutrition 0.000 claims abstract description 9
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 9
- 239000004571 lime Substances 0.000 claims abstract description 8
- 239000011419 magnesium lime Substances 0.000 claims abstract description 3
- 239000002585 base Substances 0.000 claims description 57
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 27
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 27
- 239000003921 oil Substances 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000000654 additive Substances 0.000 claims description 7
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 6
- 239000000920 calcium hydroxide Substances 0.000 claims description 6
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 6
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 235000001055 magnesium Nutrition 0.000 claims 19
- 229940091250 magnesium supplement Drugs 0.000 claims 19
- 229960000869 magnesium oxide Drugs 0.000 claims 14
- 235000012245 magnesium oxide Nutrition 0.000 claims 14
- 239000005864 Sulphur Substances 0.000 claims 7
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 1
- 238000007865 diluting Methods 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 1
- 238000005987 sulfurization reaction Methods 0.000 abstract description 10
- 239000011593 sulfur Substances 0.000 abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 abstract description 8
- 229910001854 alkali hydroxide Inorganic materials 0.000 abstract description 3
- 239000011369 resultant mixture Substances 0.000 abstract 2
- 239000000243 solution Substances 0.000 description 26
- 239000000047 product Substances 0.000 description 23
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 13
- 150000004996 alkyl benzenes Chemical class 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000010790 dilution Methods 0.000 description 8
- 239000012895 dilution Substances 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 6
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 239000013049 sediment Substances 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960002317 succinimide Drugs 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 229940077388 benzenesulfonate Drugs 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000010705 motor oil Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- JOONSONEBWTBLT-UHFFFAOYSA-N 2-tetradecylphenol Chemical class CCCCCCCCCCCCCCC1=CC=CC=C1O JOONSONEBWTBLT-UHFFFAOYSA-N 0.000 description 1
- JTZKEVHEBCTHLN-UHFFFAOYSA-N 3-(2-methylprop-1-enyl)pyrrolidine-2,5-dione Chemical compound CC(C)=CC1CC(=O)NC1=O JTZKEVHEBCTHLN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004435 Oxo alcohol Substances 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- 241001080024 Telles Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000010710 diesel engine oil Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000007788 liquid Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010690 paraffinic oil Substances 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 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
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
- C10M159/24—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing sulfonic radicals
Definitions
- the present invention relates to new detergent-dispersants of high alkalinity for lubricating oils.
- D 2896 can only be obtained by using an alcohol of the methanol type and this preferably with an organic solvent of the toluene type.
- Such a process has the drawback of using toxic methanol or a toxic mixture containing methanol which, in addition, forms with water an azeotrope which is difficult to remove.
- the Applicant has found how to adapt this type of process using an alkylene glycol, to the preparation of TBN products greater than 200 containing at least 2% magnesium and possibly at least 0.5% calcium, said products also having good properties anti-wear.
- the quantity of CO 2 used to carry out the step of over-alkalinization-carbonation can vary between the quantity which can be completely absorbed and an excess of 40% by weight of this quantity; preferably, the amount of CO 2 will correspond substantially to that which can be completely absorbed.
- calcium and / or magnesium alkylbenzene sulfonate denotes any solution containing from 40 to 95% by weight, preferably from 55 to 85% by weight of a calcium and / or magnesium alkylbenzene sulfonate in an oil of dilution which may or may not be the same as that used to carry out the process which is the subject of the invention.
- calcium and / or magnesium alkylbenzenesulfonates which can be used, mention may be made of the calcium and / or magnesium salts of sulfonic acids obtained by sulfonation of alkylbenzenes derived from olefins or polymers of C 15 ⁇ C 30 olefins.
- alkylphenols which can be used to carry out the process which is the subject of the invention, mention may preferably be made of those carrying one or more C 9 ⁇ C 15 alkyl substituents, and very particularly nonyl, decyl, dodecyl or tetradecylphenols.
- active magnesium oxide denotes magnesium oxide MgO with a specific surface greater than or equal to 80 m2 / g, for example between 100 and 170 m2 / g.
- MgO magnesium oxide MgO with a specific surface greater than or equal to 80 m2 / g, for example between 100 and 170 m2 / g.
- Maglite DE with a specific surface area close to 140 m2 / g and marketed by Merck, as well as “Ferumag”, with a specific surface area close to 160 m2 / g and marketed by RHONE-POULENC INDUSTRIES.
- alkali metal hydroxides mention may be made of sodium hydroxide, lithium hydroxide, potassium hydroxide.
- paraffinic oils such as 100 Neutral oil ...; naphthenic or mixed oils may also be suitable.
- the amount of dilution oil that can be used is such that the amount of oil contained in the final product (including that from the starting alkylbenzenesulfonate) represents from 20 to 60% by weight of said product and preferably 25 to 55% of said product.
- alkylene glycols which can be used, mention may very particularly be made of glycol; these can optionally be present in mixture with up to 200% of their weight of a monoalcohol such as ethylhexanol, tridecyl alcohol, oxo alcohols in C $ -C, 4 and in general the alcohols having a boiling point higher than 120 ° C and preferably higher than 150 ° C.
- a monoalcohol such as ethylhexanol, tridecyl alcohol, oxo alcohols in C $ -C, 4 and in general the alcohols having a boiling point higher than 120 ° C and preferably higher than 150 ° C.
- a variant of the process which is the subject of the invention consists in carrying out a precarbonation operation after the suifurization step and before the over-alkalinization-carbonation step.
- This operation can be carried out at a temperature between 100 and 250 ° C and preferably between 100 and 185 ° C, using carbon dioxide.
- the quantity of CO 2 that can be used corresponds, to more or less 30%, by weight, to that which can be completely absorbed by the sulfurized medium; preferably this quantity of CO 2 will correspond substantially to that which can be completely absorbed.
- a treatment with water may be carried out in addition to or in place of that provided for in the step of over-alkalinization-carbonation; this treatment can be carried out under the same conditions as those indicated above.
- the present invention also relates to detergents-dispersants of high alkalinity obtained by the process described above.
- the lubricating oils which can thus be improved can be chosen from a wide variety of lubricating oils, such as naphthenic, paraffinic and mixed base lubricating oils, other hydrocarbon lubricants, for example lubricating oils derived from products.
- coal, and synthetic oils for example, alkylene polymers, alkylene oxide type polymers and their derivatives, including alkylene oxide type polymers prepared by polymerizing alkylene oxide in the presence of water or alcohols, for example ethyl alcohol, esters of dicarboxylic acids, liquid esters of phosphorus acids, alkylbenzenes and dialkylbenzenes, polyphenyls, alkylbiphenyl ethers, polymers of silicon.
- lubricating oils such as naphthenic, paraffinic and mixed base lubricating oils, other hydrocarbon lubricants, for example lubricating oils derived from products.
- coal, and synthetic oils for example, alkylene polymers, alkylene oxide type poly
- Additional additives may also be present in said lubricating oils alongside the detergent-dispersants obtained according to the process of the invention; include, for example, anti-oxidant, anti-corrosion additives, ashless dispersant additives, etc.
- the medium is brought to 145 ° C. under 260 mm of mercury, then glycol is added over 1 hour; it is heated to 165 ° C. and this temperature is maintained for 1 hour under 260 mm of mercury.
- the superalkalinized and carbonated medium is brought to a temperature of 184 ° C. under 30 mm of mercury; glycol distills; it is filtered to remove the sediment and a solution in 100 N oil of overbased detergent-dispersant is recovered, the characteristics of which appear in Tables 1 to III '.
- Example 3 The operation described in Example 3 is carried out by carrying out the precarbonation step at 140 ° C. at atmospheric pressure.
- Example 3 The operation described in Example 3 is carried out from an 80% solution in 100 N oil of a magnesium alkylbenzenesulfonate of molecular weight approximately 470, solution containing 2.25% of magnesium and having a TBN of 32.
- Example 3 The operation described in Example 3 is carried out, carried out from a 60% solution in 100 N oil of a magnesium aikylbenzene sulfonate, with a molecular mass of approximately 470, solution containing 2.2% magnesium and having a TBN of 45.
- Example 3 The operation described in Example 3 is carried out from a 60% solution in 100 N oil of a calcium alkylbenzene sulfonate of molecular weight approximately 470, solution containing 2.7% of calcium and having a TBN of 25, and without adding water during the precarbonation and carbonation operations.
- Example 3 The operation described in Example 3 is carried out without adding water during the precarbonation and carbonation operations.
- the product obtained has characteristics equivalent to those of Example 3.
- Example 17 The operation described in Example 17 is carried out from a 60% solution in 100 N oil of a calcium alkylbenzenesulfonate of molecular weight approximately 470, solution containing 2.7% of calcium and having a TBN of 25 and performing a carbonation step.
- Example 17 The operation described in Example 17 is carried out using the same quantities of reagents, but. by carrying out the sulfurization operation first at 165 ° C for 1 hour under 260 mm of mercury and then for 2 hours at 185 ° C under 700 mm of mercury.
- the product obtained has characteristics equivalent to those of Example 17.
- Example 7 The product of Example 7 is added to an SAE 50 oil with a paraffinic tendency so as to obtain a solution containing 125 millimoles of calcium + magnesium. The solution is stored for 15 days at 20 ° C; we see that the solution remains clear.
- mixture (A) is brought for 25 days to 80 ° C. and is then added to an SAE 30 oil so as to have a concentration of 6.6% by weight of mixture (A).
- the solution is stored for 5 days at 80 ° C.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Detergent Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT79400376T ATE1342T1 (de) | 1978-06-26 | 1979-06-11 | Verfahren zur herstellung von reinigungsmittelloesungen hoher alkalitaet fuer schmieroele und daraus hergestelltes produkt. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7818945A FR2429831A2 (fr) | 1978-06-26 | 1978-06-26 | Nouveau procede de preparation de detergents-dispersants de haute alcalinite pour huiles lubrifiantes |
| FR7818945 | 1978-06-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0007257A1 EP0007257A1 (fr) | 1980-01-23 |
| EP0007257B1 true EP0007257B1 (fr) | 1982-07-14 |
Family
ID=9209958
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP79400376A Expired EP0007257B1 (fr) | 1978-06-26 | 1979-06-11 | Procédé de préparation de détergents-dispersants de haute alcalinité pour huiles lubrifiantes et produit obtenu |
Country Status (11)
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4710308A (en) * | 1982-04-08 | 1987-12-01 | Amoco Corporation | Process for preparing overbased sulfurized phenates |
| FR2529225B1 (fr) * | 1982-06-24 | 1986-04-25 | Orogil | Nouvel additif detergent-dispersant metallique de haute alcalinite pour huiles lubrifiantes |
| FR2529226B1 (fr) * | 1982-06-24 | 1987-01-16 | Orogil | Procede de preparation d'alkylphenates sulfurises de metaux alcalino-terreux utilisables comme additifs pour huiles lubrifiantes |
| FR2529224B1 (fr) * | 1982-06-24 | 1986-02-07 | Orogil | Nouvel additif detergent-dispersant suralcalinise pour huiles lubrifiantes |
| JPS5931724A (ja) * | 1982-08-16 | 1984-02-20 | Cosmo Co Ltd | 塩基性アルカリ土類金属フェネートもしくはその二酸化炭素処理物の製造法 |
| JPS59232190A (ja) * | 1983-06-15 | 1984-12-26 | Taiyo Kako Kk | 高塩基度の硫化アルキルフエノ−ルアルカリ土類金属塩を含有する油溶液の製法 |
| FR2584414B1 (fr) * | 1985-07-08 | 1987-10-30 | Orogil | Nouveaux additifs detergents-dispersants sulfones et sulfurises pour huiles lubrifiantes |
| FR2588269B1 (fr) * | 1985-10-03 | 1988-02-05 | Elf France | Procede de preparation d'additifs surbases tres fluides et a basicite elevee et composition contenant lesdits additifs |
| DK0385616T3 (da) * | 1989-02-25 | 1994-10-10 | Bp Chemicals Additives | Fremgangsmåde til fremstilling af et smøreolieadditivkoncentrat |
| US4973411A (en) * | 1989-09-15 | 1990-11-27 | Texaco Inc. | Process for the preparation of sulfurized overbased phenate detergents |
| US5332514A (en) * | 1990-08-06 | 1994-07-26 | Texaco Inc. | Continuous process for preparing overbased salts |
| US5330664A (en) * | 1992-09-02 | 1994-07-19 | Chevron Research And Technology Company | Neutral and low overbased alkylphenoxy sulfonate additive compositions derived from alkylphenols prepared by reacting an olefin or an alcohol with phenol in the presence of an acidic alkylation catalyst |
| US5330663A (en) * | 1992-09-02 | 1994-07-19 | Chevron Research And Technology Company | Neutral and low overbased alkylphenoxy sulfonate additive compositions |
| TW278098B (enrdf_load_stackoverflow) * | 1992-09-18 | 1996-06-11 | Cosmo Sogo Kenkyusho Kk | |
| US5320763A (en) * | 1993-03-12 | 1994-06-14 | Chevron Research And Technology Company | Low viscosity group II metal overbased sulfurized C10 to C16 alkylphenate compositions |
| US5318710A (en) * | 1993-03-12 | 1994-06-07 | Chevron Research And Technology Company | Low viscosity Group II metal overbased sulfurized C16 to C22 alkylphenate compositions |
| US5320762A (en) * | 1993-03-12 | 1994-06-14 | Chevron Research And Technology Company | Low viscosity Group II metal overbased sulfurized C12 to C22 alkylphenate compositions |
| US6235688B1 (en) | 1996-05-14 | 2001-05-22 | Chevron Chemical Company Llc | Detergent containing lithium metal having improved dispersancy and deposit control |
| US7405185B2 (en) * | 2003-09-26 | 2008-07-29 | Chevron Oronite Company Llc | Process for making Group II metal overbased sulfurized alkylphenols |
| CN110088206B (zh) | 2016-09-01 | 2021-08-20 | 陶氏东丽株式会社 | 固化性有机聚硅氧烷组合物以及电气电子零部件的保护剂或粘合剂组合物 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1080531A (fr) * | 1952-02-01 | 1954-12-09 | Standard Oil Dev Co | Préparation de produits composés contenant des sulfonates métalliques et des selsmétalliques de sulfures aromatiques |
| USB194963I5 (enrdf_load_stackoverflow) * | 1962-05-15 | |||
| US3178368A (en) * | 1962-05-15 | 1965-04-13 | California Research Corp | Process for basic sulfurized metal phenates |
| US3878116A (en) * | 1970-09-09 | 1975-04-15 | Bray Oil Co | Overbased sulfonates |
| GB1429243A (en) * | 1973-02-22 | 1976-03-24 | Orobis Ltd | Overbased phenates |
| GB1469289A (en) * | 1974-07-05 | 1977-04-06 | Exxon Research Engineering Co | Detergent additives |
| JPS5272707A (en) * | 1975-12-15 | 1977-06-17 | Karonaito Kagaku Kk | Preparation of additive for perbasic lubricating oil |
| FR2416942A1 (fr) * | 1978-02-08 | 1979-09-07 | Orogil | Procede de preparation de detergents-dispersants de haute alcalinite pour huiles lubrifiantes |
| US4148740A (en) * | 1978-05-01 | 1979-04-10 | Witco Chemical Corporation | Preparation of overbased magnesium sulfonates |
-
1978
- 1978-06-26 FR FR7818945A patent/FR2429831A2/fr active Granted
-
1979
- 1979-06-11 AT AT79400376T patent/ATE1342T1/de not_active IP Right Cessation
- 1979-06-11 EP EP79400376A patent/EP0007257B1/fr not_active Expired
- 1979-06-11 DE DE7979400376T patent/DE2963335D1/de not_active Expired
- 1979-06-19 US US06/050,089 patent/US4302342A/en not_active Expired - Lifetime
- 1979-06-21 MX MX798105U patent/MX5733E/es unknown
- 1979-06-22 CA CA330,658A patent/CA1122963A/fr not_active Expired
- 1979-06-25 ES ES481863A patent/ES481863A1/es not_active Expired
- 1979-06-25 BR BR7904003A patent/BR7904003A/pt not_active IP Right Cessation
- 1979-06-26 JP JP7979479A patent/JPS555991A/ja active Granted
- 1979-06-26 ZA ZA793194A patent/ZA793194B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2963335D1 (en) | 1982-09-02 |
| FR2429831A2 (fr) | 1980-01-25 |
| ES481863A1 (es) | 1980-02-16 |
| CA1122963A (fr) | 1982-05-04 |
| JPS555991A (en) | 1980-01-17 |
| MX5733E (es) | 1984-01-25 |
| US4302342A (en) | 1981-11-24 |
| ZA793194B (en) | 1980-06-25 |
| BR7904003A (pt) | 1980-03-25 |
| ATE1342T1 (de) | 1982-07-15 |
| EP0007257A1 (fr) | 1980-01-23 |
| JPH0142998B2 (enrdf_load_stackoverflow) | 1989-09-18 |
| FR2429831B2 (enrdf_load_stackoverflow) | 1982-06-11 |
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