US3746698A - Preparation of highly basic,sulfurized alkylphenols - Google Patents
Preparation of highly basic,sulfurized alkylphenols Download PDFInfo
- Publication number
- US3746698A US3746698A US00197519A US3746698DA US3746698A US 3746698 A US3746698 A US 3746698A US 00197519 A US00197519 A US 00197519A US 3746698D A US3746698D A US 3746698DA US 3746698 A US3746698 A US 3746698A
- Authority
- US
- United States
- Prior art keywords
- magnesium
- calcium
- alkylphenol
- admixture
- product
- 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 - Lifetime
Links
- 238000002360 preparation method Methods 0.000 title description 10
- 238000000034 method Methods 0.000 abstract description 99
- 230000008569 process Effects 0.000 abstract description 89
- 239000011777 magnesium Substances 0.000 abstract description 81
- 229910052749 magnesium Inorganic materials 0.000 abstract description 78
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract description 67
- 239000011575 calcium Substances 0.000 abstract description 66
- 229910052791 calcium Inorganic materials 0.000 abstract description 66
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract description 55
- 239000000463 material Substances 0.000 abstract description 49
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 34
- 239000011593 sulfur Substances 0.000 abstract description 34
- 229910052717 sulfur Inorganic materials 0.000 abstract description 34
- 238000010438 heat treatment Methods 0.000 abstract description 25
- 239000010687 lubricating oil Substances 0.000 abstract description 18
- 239000000654 additive Substances 0.000 abstract description 4
- 238000006386 neutralization reaction Methods 0.000 abstract description 4
- 238000005987 sulfurization reaction Methods 0.000 abstract description 3
- 230000000996 additive effect Effects 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- XLYOFNOQVPJJNP-PWCQTSIFSA-N Tritiated water Chemical compound [3H]O[3H] XLYOFNOQVPJJNP-PWCQTSIFSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 50
- 239000000543 intermediate Substances 0.000 description 47
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 31
- 239000003921 oil Substances 0.000 description 25
- 235000019198 oils Nutrition 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 229910052751 metal Inorganic materials 0.000 description 23
- 239000002184 metal Substances 0.000 description 23
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 20
- 239000003085 diluting agent Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- -1 alkaline earth metal salts Chemical class 0.000 description 18
- 125000003545 alkoxy group Chemical group 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 14
- 238000010992 reflux Methods 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 239000012467 final product Substances 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
- 239000010688 mineral lubricating oil Substances 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 4
- 239000001095 magnesium carbonate Substances 0.000 description 4
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 4
- 150000002736 metal compounds Chemical class 0.000 description 4
- 230000003472 neutralizing effect Effects 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 239000013049 sediment Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 238000007664 blowing Methods 0.000 description 3
- 159000000007 calcium salts Chemical class 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- HGAZMNJKRQFZKS-UHFFFAOYSA-N chloroethene;ethenyl acetate Chemical compound ClC=C.CC(=O)OC=C HGAZMNJKRQFZKS-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- JKTAIYGNOFSMCE-UHFFFAOYSA-N 2,3-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1CCCCCCCCC JKTAIYGNOFSMCE-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- DWKXSNPRMXPRKO-UHFFFAOYSA-M C([O-])(O)=O.COC([O-])C.[Mg+2] Chemical compound C([O-])(O)=O.COC([O-])C.[Mg+2] DWKXSNPRMXPRKO-UHFFFAOYSA-M 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 241001647090 Ponca Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052728 basic metal Inorganic materials 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 159000000003 magnesium salts Chemical group 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000010689 synthetic lubricating oil Substances 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- 241001556567 Acanthamoeba polyphaga mimivirus Species 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000005997 Calcium carbide 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
- 239000005909 Kieselgur Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 125000001204 arachidyl 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])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])[H] 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940043430 calcium compound Drugs 0.000 description 1
- 150000001674 calcium compounds Chemical class 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 125000003901 ceryl 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])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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 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
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 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
- 150000002148 esters Chemical class 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000010699 lard oil Substances 0.000 description 1
- YXOSSQSXCRVLJY-UHFFFAOYSA-N magnesium;2-methoxyethanolate Chemical compound COCCO[Mg]OCCOC YXOSSQSXCRVLJY-UHFFFAOYSA-N 0.000 description 1
- 125000001802 myricyl 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])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])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])[H] 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
- 125000002347 octyl 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])[H] 0.000 description 1
- 238000010915 one-step procedure Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000913 palmityl 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])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
- 239000002245 particle Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 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
- CLZWAWBPWVRRGI-UHFFFAOYSA-N tert-butyl 2-[2-[2-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-5-bromophenoxy]ethoxy]-4-methyl-n-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]anilino]acetate Chemical compound CC1=CC=C(N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)C(OCCOC=2C(=CC=C(Br)C=2)N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)=C1 CLZWAWBPWVRRGI-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000004711 α-olefin Substances 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
- C10M159/22—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing phenol radicals
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic compounds
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/024—Propene
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
-
- 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
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- 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
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
-
- 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
- C10M2207/40—Fatty vegetable or animal oils
-
- 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
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
-
- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
-
- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
-
- 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
- C10M2219/046—Overbased sulfonic acid 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
- C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
-
- 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
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
-
- 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
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
Definitions
- step (b) adding to the admixture of step (a) the amount of magnesium and/ or calcium alkoxy alkoxide-carbonate complex required for overbasing,
- step (c) adding to the admixture of step (b) the amount of magnesium and/ or calcium alkoxy alkoxide-carbonate complex required for neutralization, and
- step (d) said process being characterized further in that the amount of sulfur required for sulfurization of the alkylphenol is added at any time prior to step (d).
- the products are particularly useful as additive agents for lubricating oils.
- highly basic alkaline earth metal salts of alkylphenates or sulfurized alkylphenates as additives in lubricating oils has been known for several years.
- highly basic refers to materials containing an excess of alkaline earth metal basic compounds over the amount of alkaline earth metal required to neutralize the alkylphenol or sulfurized alkylphenol.
- the presence of these basic alkaline earth metal compounds serves to neutralize acidic materials formed during combustion of the fuel used.
- highly basic alkaline earth metal sulfurized alkylphenates have been prepared using one of the following methods.
- One method uses a commercially available sulfurized alkylphenate.
- the second method uses a two-step procedure wherein the neutral sulfurized "ice alkylphenate is prepared in the first step and the highly basic sulfurized alkylphenate is prepared in the second step.
- the present invention is directed to a combined or onestep process for overbasing and sulfurizing alkylphenols.
- the process is referred to as one-step in that both overbasing and sulfurizing are effected prior to removing volatile solvents.
- the process has the advantage of being more eflicient While also preparing an outstanding product.
- U.S. Pat. No. 2,788,325 teaches the use of magnesium alkoxy alkoxides to prepare neutral magnesium phenates.
- the patent teaches the use of temperatures between 100 C. and 250 C. and substantially anhydrous conditions.
- U.S. Pat. No. 3,528,917 teaches the preparation of normal (or neutral) calcium sulfurized alkylphenate by the sequential or simultaneous reaction of alkylphenol with a calcium alkoxy alkoxide and sulfur in the presence of a hydrocarbon lubricating oil.
- the patent teaches that preferably the alkylphenol is sequentially contacted with calcium alkoxy alkoxide to form normal calcium alkylphenate followed by a sulfur contact to form the sulfurized normal calcium alkylphenate.
- U.S. Pat. No. 3,474,035 (035) teaches the preparation of an overbased calcium sulfurized alkylphenate from the normal calcium sulfurized alkylphenate of U.S. 3,528,917. According to the process of 035, the normal calcium sulfurized alkylphenate is contacted with a calcium alkoxy alkoxide to form an overbased product having a calcium metal ratio of from 1.1 to about 3.5 and then contacting the product with water in a manner to afiect between about 20 and percent of the overbased product followed by a substantial removal of any unreacted Water.
- the dispersed material is predominantly magnesium carbonate, calcium carbonate, or mixtures thereof.
- the present invention is a process for preparing highly basic magnesium and calcium salts of sulfurized alkylphenols, wherein the process comprises the steps of:
- step (b) adding to the admixture of step (a) the amount required for overbasing of an alkoxy alkanol solution of a calcium or magnesium alkoxy alkoxide-carbonate complex, or mixtures thereof,
- step (b) adding to the admixture of step (b) the amount required for neutralization of an alkoxy alkanol solution of a calcium or magnesium alkoxy alkoxide-carbonate complex, or mixtures thereof, preferably while maintaining the temperature higher than that of step (b), and (d) heating to remove the volatile materials,
- said process being characterized further in that the amount of sulfur required for sulfurization of the alkylphenol is added prior to removing volatile materials.
- a nonvolatile diluent oil is usually added. This can be added at any step during the process or to the product. It should be emphasized that the nonvolatile diluent oil is not absolutely essential.
- Suitable alkylphenols for use in our process are represented by the formula wherein R is a straight chain or branched chain, saturated or unsaturated, aliphatic hydrocarbon radical having from 4 to 30 carbon atoms, preferably from 9 to 15 carbon atoms, and n is an integer having a value of l or 2.
- the total number of carbon atoms for the alkyl groups has a minimum value of 8 and a maximum value of 40. Thus, when n is 1 the minimum number of carbon atoms in R is 8.
- hydrocarbon radicals examples include alkyl radicals such as butyl, hexyl, octyl, nonyl, decyl, dodecyl, hexadecyl, eicosyl, hexacosyl and triacontyl; radicals derived from petroleum hydrocarbons such as white oil, wax and olefin polymers (e.g. polypropylene and polybutylene).
- Products prepared without adding any non-volatile diluent oil are usually solid at ambient temperature since only a smal amount of oil is normally present in the alkylphenol. Accordingly, it is usual practice to add some nonvolatile diluent oil in order to reduce the viscosity of the final product mixture. Since reduction of viscosity is the principal requisite, a wide variety of nonvolatile diluent oils are suitable.
- the nonvolatile diluent oils have a boiling point in excess of about 200 C.
- nonvolatile diluent oils examples include mineral lubricating oils obtained by conventional refining procedures; synthetic lubricating oils such as polymers of propylene, polyoxyalkylenes, polyoxypropylene; dicarboxylic acid esters, and esters of acids or phosphorus; synthetic hydrocarbon lubricating oils, such as di-n-alkylbenzenes and oligomers of C -C alpha-olefins; vegetable oils, such as corn oil, cottonseed oil, and castor oil; animal oils, such as lard oil and sperm oil. Mixtures of these materials can also be employed as the nonvolatile diluent.
- nonvolatile diluent oils the mineral lubricating oils and the synthetic lubricating oils are considered more suitable, with the mineral lubricating oils being preferred.
- Suitable process solvents for use in our process have a boiling point below about 190 0., preferably below about 150 C.
- suitable volatile process solvents include aromatic hydrocarbons, such as benzene, toluene, xylene, aliphatic hydrocarbons, such as hexane, heptane, petroleum naphtha, alkoxy alkanols, as defined hereinafter, and primary aliphatic C -C alcohols.
- Suitable alkaline earth metals for forming the salts of the sulfurized alkylphenols and for forming the dispersed metal compound are calcium and magnesium. It is to be understod that mixtures of calcium and magnesium are suitable. This includes processes where both are used for forming the phenate and dispersed metal and where one is used for forming the phenate and the other is used for forming the dispersed metal compound.
- alkoxy alkanol as used herein refers to materials represented by the formula ROCH CH O H where R is a C to C alkyl group. Methoxyethanol is the most suitable alkoxy alkanol.
- the alkoxy alkanols are available commercially under the trademark Cellosolve, methyl Cellosolve, and butyl Cellosolve.
- the calcium and magnesium alkoxy alkoxide-complexes are represented by the formula:
- M is magnesium or calcium
- R is a C to C alkyl group
- X is a number of from 0.5 to 1.5, preferably from 0.85
- the magnesium intermediate is prepared by reacting the magnesium with the alkoxy alkanol followed by carbonation.
- the calcium intermediate is prepared by reacting an alkoxy alkanol with calcium metal, calcium hydride or calcium carbide, followed by carbonation.
- Any commercial grade of sulfur can be used in our process provided it is in the form of small particles. Powdered sulfur is particularly suitable.
- the water requirements of the process of our invention can 'be met using water -per se, alkoxy alkanol-water mixtures, or aliphatic alcohol-water mixtures.
- an oil-soluble sufonic acid in the process of our invention.
- the amount of oil-soluble sulfonic acid is from about 0.1 to about 50 parts per parts of alkylphenol or sulfurized alkylphenol.
- oil-soluble sulfonic acid When using the oil-soluble sulfonic acid preferably a volatile hydrocarbon solvent (e.g. hexane) containing the oil-soluble sulfonic acid is used.
- a volatile hydrocarbon solvent e.g. hexane
- oil-soluble sulfonic acid is well known in the art. In general, it refers to materials wherein the hydrocarbon portion of the molecule has a molecular weight in the range of about 300 to about 1,000, preferably in the range of about 370 to about 700.
- Particularly suitable oil-soluble sulfonic acids are those prepared from various synthetic hydrocarbon sulfonation feedstocks. These materials are usually alkylbenzenes being either monoor di-alkyl substituted. The alkyl groups have sufficient carbon atoms to attain the requisite molecular weight range described in the foregoing.
- the nonvolatile diluent oil is not essential.
- the amount of water is also from about 0.75 to about 3.0 moles, preferably from about 1.05 to about 2.0 moles per mole of dispersed magnesium and/or calcium (total amount) present in the final product.
- an overbasing amount (from about 0.10 to about 5 equivalents of metal per equivalent of alkylphenol) of calcium or magnesium intermediate.
- the overbasing amount of the calcium or magnesium intermediate, or mixtures thereof, is added while maintaining the temperature of the admixture in the range of about 15 to about 100 0., preferably in the range of about 20 to about 75 C., and more preferably in the range of about 25 to about 55 C. While the time of adding the overbasing amount of the calcium of magnesium metal is not particularly critical, it is desirable that this addition occurs in a time period of from about 5 to about 180 minutes, preferably from about 30 to about 120 minutes.
- a neutralizing amount (from about 0.95 to about 1.25 equivalent of metal per equivalent of alkylphenol) of calcium or magnesium intermediate, or mixtures thereof, is then added to the admixture.
- the admixture is maintained at a temperature of between 50 and about 100 C., preferably from about 55 to 80 C. Most preferably, the temperature in this step is higher than that of the overbasing step.
- the required amount of sulfur can be added to the admixture at any time up through this step.
- the sulfur can be added to the initial admixture in any step up through the neutralizing step.
- it is desirable to agitate the admixture after adding the sulfur We have found that adding the sulfur after heating has begun to remove the volatile materials results in a substantial increase of the sediment, as measured by the B.S. & W. test.
- the admixture is heated to a suitable temperature to remove the volatile materials present. It is apparent that the temperature required at this point is controlled by the boiling points of the volatile materials present. Temperatures in the range of to 190 C. are employed with the temperature range usually being about 140 to about C. Following removal of the volatile materials the admixture is heated and contacted with carbon dioxide at a temperature in the range of about 140 to about 200 C. Blowing with carbon dioxide at this point serves to substantially complete the carbonation of the magnesium or calcium compound and to remove traces of volatile materials. Knowing that this is the purpose of blowing with CO at this point anyone skilled in the art can readily determine the amount of time required. We have found time periods in the range of 15 minutes to 24 hours to be satisfactory, usually a time period in the range of about 30 minutes to 12 hours is satisfactory.
- a nonvolatile diluent oil is added.
- the nonvolatile diluent oil can be added at any step during the process or to the product. -It is convenient to add the nonvolatile diluent oil to the initial admixture or to the product after removing volatile materials. Also, it is convenient to add a major portion of the nonvolatile diluent oil to the initial admixture followed by adding an amount to the final product to produce the desired viscosity.
- the nonvolatile diluent oil can serve to adjust the product activity (i.e., the concentration of alkylphenate and dispersoid materials).
- the dispersed metal compound As the base number which refers to milligrams of potassium hydroxide per gram of sample.
- the base number is an acetic base number referring to an acetic acid titration method which utilizes glacial acetic acid and a solution of perchloric acid in glacial acetic acid as the titrant.
- a second method uses the term metal ratio which is defined as the ratio of excess equivalents of metal in the composition to the equivalents of metal theoretically combinable as a normal salt with the alkylphenol or sulfurized alkylphenol.
- the products of our invention suitably have a metal ratio in the range of about 0.05 to about 5.0, preferably in the range of about 0.4 to about 2.0.
- EXAMPLE 1 This example illustrates the preparation of a dispersion of magnesium carbonate in a magnesium sulfurized alkylphenate.
- the preparation was duplicated.
- the combined products were filtered while hot (about 100 C.) through a diatomaceous earth filter aid to remove traces of sediment.
- EXAMPLE 2 This example illustrates adding the sulfur to the initial admixture.
- the naphthenic lubricating oil was added to adjust the product viscosity. While heating the product at 160-180 C., it was blown with CO gas for one hour in order to remove the last traces of volatile components. The yield of product was 408.4 grams.
- EXAMPLE 3 This example illustrates adding the sulfur after the overbasing step and prior to distillation to remove volatile materials. Materials used were the same as in Example 2, except that the amount of naphthenic lubricating oil was 150 grams.
- Process EXAMPLE 4 This example illustrates adding the sulfur after the addition of the first part of the magnesium intermediate followed by heating to reflux temperature and prior to adding the second part of the magnesium intermediate. Materials used were the same as in Example 3.
- EXAMPLE 5 This example illustrates adding the sulfur during the distillation step to remove the volatile materials. Materials used were the same as in Example 3.
- EXAMPLE 6 This example also illustrates adding the sulfur during the distillation step to remove the volatile materials. Materials. Materials used were the same as in Example 2.
- EXAMPLE 7 The example illustrates the preparation of a dispersion of calcium carbonate in a calcium sulfun'zed alkylphenol.
- This alkylphenol had an average molecular weight of 262 and the following composition:
- N peas-weer ODNWCDNEDOQ Process
- alkylphenol alkylphenol, n-hexane, methoxyethanol, sulfonic acid, and water.
- one-half of the magnesium intermediate was added over a 60-minute time period while gradually heating the admixture from 25 to 55 C.
- the admixture was then heated to reflux temperature (about 707 3 C.) and the remaining one-half of the magnesium intermediate was added over a 60-minute time period.
- the sulfur was then added at this point.
- the solvents were removed by heating to a temperature of C.
- the product was then blown with CO gas for one hour while remaining at a temperature in the range of -l80 C. During the early part of this CO blowing, when the temperature was about 160 C., the naphthenic lubricating oil was added to the product. Also, a small sample was removed by the B. S. & W. test. While hot the product was filtered through a diatornaceous earth filter aid. The product had the following analyses and properties:
- the product yield was 395.6 grams.
- EXAMPLE 9 This example also illustrates the preparation of a dispersion of magnesium carbonate in a magnesium sulfurized alkylphenol.
- the alkylphenol used was a mixture of monononylphenol and dinonylphenol.
- Example 8 Materials used Same as in Example 8 with the exception that a slightly different alkylphenol was used. The amounts of materials were exactly the same.
- the alkylphenol used had an aver- 1 1 age molecular weight of 246 and the following composi tion:
- the product had the following analyses and properties:
- EXAMPLE This example is comparative and shows that the use of a magnesium alkoxy alkoxide instead of a magnesium alkoxy alkoxide-carbonate complex in the process of our 1 Same as footnote 1 in Example 1.
- the admixture became very viscous and gelatinous. About 50 grams of benzene were added in an attempt to fluidize the mixture. Mixing was very poor due to the viscous nature of the product.
- the admixture was heated to 160 C. to remove solvents. It was necessary during this heating to add another 40 grams of naphthenic lubricating oil in order to keep the product of manageable consistency. Finally, the product was blown with nitrogen gas at 160-180 C. for one hour. The product yield was 340.4 grams. The product was an extremely viscous material, which was hard and rubbery at room temperature, and incompatible in SAE 50 lubricating oil.
- step (b) while the temperature is in the range of about 15 to about C., adding to the admixture of step (a) an overbasing amount, in the range of about 0.10 to about 5 equivalent of metal per equivalent of alkylphenol, of a metal intermediate selected from the group consisting essentially of:
- step (d) removing the volatile materials by heating, said process being characterized further in that (i) from about 0.5 to about 20 parts by weight of sulfur are added prior to removing the volatile materials by heating in step (d),
- said magnesium intermediate and said calcium intermediate being an alkoxy alkanol solution of a magnesium alkoxy alkoxide-carbonate complex or a calcium alkoxy alkoxide-carbonate complex, wherein the alkoxy alkanol is represented by the formula ROCH3CH2OH with R being a C to C alkyl group and the magnesium and calcium alkoxy alkoxide complexes are'represented by the formula 0 I] M(ooH2oH2oR), x(o-o-0ornomom wherein 13 M is magnesium or calcium R is a C to C alkyl group, and X is a number from 0.5 to 1.5, and (iii) the amount of water in step (a) (iii) is sufficient to provide about 0.75 to about 3.0 moles per mole of dispersed magnesium or calcium.
- the alkoxy alkanol is represented by the formula ROCH3CH2OH with R being a C to C alkyl group and the magnesium and calcium alkoxy alkoxide complexe
- process solvent is selected from the group consisting of aromatic hydrocarbons, aliphatic hydrocarbons, primary aliphatic C -C alcohols, and alkoxy alkanols containing from 3 to 8 carbon atoms.
- step (b) The process of claim 2 wherein the temperature of the admixture in step (b) is in the range of about 20 to about 75 C.
- step (c) is in the range of about 55 to about 80 C.
- step (b) is in the range of about 25 to about 55 C., and (b) the temperature in step (c) is higher than that of step (b).
- step (a) (iii) is sufiicient to provide about 1.05 to about 2.0 moles per mole of dispersed magnesium or calcium.
- process solvent is a mixture of an aliphatic hydrocarbon and a C -C alkoxy alkanol.
- nonvolatile diluent oil is a mineral lubricating oil.
- step (b) while the temperature is in the range of about 20 to about 75 C., adding to the admixture of step (a) an overbasing amount, in the range of about 0.10 to about 5 equivalent of metal per equivalent of alkylphenol, of a metal intermediate selected from the group consisting essentially of:
- step (d) removing the volatile materials by heating, said process being characterized further in that (i) from about 1.0 to about 15 parts by weight of sulfur are added prior to removing the volatile materials by heating in step (d), and
- said magnesium intermediate and said calcium intermediate being an alkoxy alkanol solution of a magnesium alkoxy alkoxide-carbonate complex or a calcium alkoxy alkoxide-carbonate complex, wherein the alkoxy alkanol is represented by the formula ROCH CHgOH with R being a C to C alkyl group and the magnesium and calcium alkoxy alkoxide complexes are represented by the formula wherein M is magnesium or calcium R is a C to C alkyl group, and X is a number from 0.5 to 1.5, and (iii) the amount of water in step (a) (iii) is sufficient to provide about 0.75 to about 3.0 moles per mole of dispersed magnesium or calcium.
- the alkoxy alkanol is represented by the formula ROCH CHgOH with R being a C to C alkyl group
- the magnesium and calcium alkoxy alkoxide complexes are represented by the formula wherein M is magnesium or calcium R is a C to C alkyl group, and X is a
- process solvent is selected from the group consisting of aromatic hydrocarbons, aliphatic hydrocarbons, primary aliphatic C -C alcohols, and alkoxy alkanol containing from 3 to 8 carbon atoms.
- step (b) is in the range of about 25 to about 55 C. and the temperature in step (c) is higher than that of step (b).
- step (a) (iii) is sufficient to provide about 1.05 to about 2.0 moles per mole of dispersed magnesium or calcium.
- process solvent is a mixture of an aliphatic hydrocarbon and a C -C alkoxy alkanol.
- nonvolatile diluent oil is a mineral lubricating oil.
- step (d) the product is blown with CO at a temperature in the range of about to about 200 C.
- step (a) contains additionally from about 0.1 to about 50 parts of oil-soluble sulfonic acid per 100 parts of alkylphenol.
- step (a) contains additionally from about 0.1 to about 50 'parts of oil-soluble sulfonic acid per 100' parts of alkylphenol.
- step (a) contains additionally from about 0.1 to about 50 parts of oil-soluble sulfonic acid per 100 parts of alkylphenol.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19751971A | 1971-11-10 | 1971-11-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3746698A true US3746698A (en) | 1973-07-17 |
Family
ID=22729738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00197519A Expired - Lifetime US3746698A (en) | 1971-11-10 | 1971-11-10 | Preparation of highly basic,sulfurized alkylphenols |
Country Status (8)
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4016093A (en) * | 1976-03-19 | 1977-04-05 | Mobil Oil Corporation | Metal alkylphenate sulfides of reduced corrosiveness and method of preparing same |
| US4104180A (en) * | 1975-05-23 | 1978-08-01 | Exxon Research & Engineering Co. | Production of overbased metal phenates |
| FR2429203A1 (fr) * | 1978-06-20 | 1980-01-18 | Witco Chemical Corp | Procede de preparation de phenates sulfures de magnesium surbasiques |
| US4228022A (en) * | 1979-06-28 | 1980-10-14 | Chevron Research Company | Sulfurized alkylphenol-olefin reaction product lubricating oil additive |
| US4295981A (en) * | 1979-07-27 | 1981-10-20 | Burnop Victor C | Production of overbased magnesium detergent additives |
| US4873007A (en) * | 1988-09-26 | 1989-10-10 | Amoco Corporation | Method for producing sulfurized alkylphenols |
| US5589445A (en) * | 1994-08-19 | 1996-12-31 | Bp Chemicals (Additives) Limited | Overbased metal salts, their preparation and use |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
1971
- 1971-11-10 US US00197519A patent/US3746698A/en not_active Expired - Lifetime
-
1972
- 1972-09-28 CA CA152,815A patent/CA1000691A/en not_active Expired
- 1972-10-17 DE DE2250882A patent/DE2250882A1/de not_active Ceased
- 1972-10-31 IT IT53727/72A patent/IT966859B/it active
- 1972-11-03 GB GB5075172A patent/GB1392248A/en not_active Expired
- 1972-11-09 FR FR7239803A patent/FR2160151A1/fr not_active Withdrawn
- 1972-11-10 JP JP47112174A patent/JPS5919932B2/ja not_active Expired
-
1973
- 1973-06-27 BE BE132797A patent/BE801534Q/xx not_active IP Right Cessation
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4104180A (en) * | 1975-05-23 | 1978-08-01 | Exxon Research & Engineering Co. | Production of overbased metal phenates |
| US4016093A (en) * | 1976-03-19 | 1977-04-05 | Mobil Oil Corporation | Metal alkylphenate sulfides of reduced corrosiveness and method of preparing same |
| FR2429203A1 (fr) * | 1978-06-20 | 1980-01-18 | Witco Chemical Corp | Procede de preparation de phenates sulfures de magnesium surbasiques |
| US4228022A (en) * | 1979-06-28 | 1980-10-14 | Chevron Research Company | Sulfurized alkylphenol-olefin reaction product lubricating oil additive |
| US4295981A (en) * | 1979-07-27 | 1981-10-20 | Burnop Victor C | Production of overbased magnesium detergent additives |
| US4873007A (en) * | 1988-09-26 | 1989-10-10 | Amoco Corporation | Method for producing sulfurized alkylphenols |
| US5589445A (en) * | 1994-08-19 | 1996-12-31 | Bp Chemicals (Additives) Limited | Overbased metal salts, their preparation and use |
Also Published As
| Publication number | Publication date |
|---|---|
| IT966859B (it) | 1974-02-20 |
| GB1392248A (en) | 1975-04-30 |
| DE2250882A1 (de) | 1973-05-17 |
| BE801534Q (fr) | 1973-10-15 |
| JPS5919932B2 (ja) | 1984-05-09 |
| JPS4854046A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-07-30 |
| CA1000691A (en) | 1976-11-30 |
| FR2160151A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-06-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3493516A (en) | Carboxylate modified phenates | |
| US3178368A (en) | Process for basic sulfurized metal phenates | |
| CA1049486A (en) | Overbased magnesium phenate detergents | |
| US5534168A (en) | Preparation of overbased magnesium sulphonates | |
| US4057504A (en) | Method of preparing overbased lubricating oil additives | |
| US4302342A (en) | Process for the preparation of detergent dispersants of high alkalinity for lubricating oils and the product obtained therefrom | |
| US3372114A (en) | Process for preparing thickened mineral oil compositions | |
| US4251379A (en) | Detergent-dispersants of high alkalinity for lubricating oils and process for their preparation | |
| EP0092415B1 (en) | Preparation of overbased magnesium phenates | |
| US3853774A (en) | Process for preparing oil-soluble basic magnesium salts | |
| US3746698A (en) | Preparation of highly basic,sulfurized alkylphenols | |
| US3182019A (en) | Process for preparing petroleum oil additives | |
| US4464289A (en) | Super-alkalinized detergent-dispersant additives for lubricating oils and method of making same | |
| US3755170A (en) | Preparation of highly basic alkylphenates and sulfurized alkyphenates | |
| US4293431A (en) | Process of preparing metallic detergent-dispersant additives of high alkalinity in particular for lubricating oils, and product obtained thereby | |
| US3830739A (en) | Preparation of hyperbasic dispersions | |
| US3336224A (en) | High alkalinity overbased phenate | |
| US3446736A (en) | Mixed carboxylate derivatives of basic alkaline earth metal sulfonates | |
| US4470916A (en) | High alkalinity metallic detergent-dispersant additives for lubricating oils and method of making same | |
| JP2598489B2 (ja) | 過塩基マグネシウムスルホン酸塩組成物 | |
| JPH0580517B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| US4867891A (en) | Overbased alkali metal sulfonates | |
| US2856361A (en) | Superbasic alkaline earth metal sulfonates | |
| US3806454A (en) | Process for preparing barium-containing dispersion | |
| US3718589A (en) | Preparation of neutral and highly basic alkylphenates and sulfurized alkylphenates |