CN1015642B - 碱土金属烃基酚盐及其磁化衍生物，它们的制备和应用 - Google Patents
碱土金属烃基酚盐及其磁化衍生物，它们的制备和应用Info
- Publication number
- CN1015642B CN1015642B CN87108239A CN87108239A CN1015642B CN 1015642 B CN1015642 B CN 1015642B CN 87108239 A CN87108239 A CN 87108239A CN 87108239 A CN87108239 A CN 87108239A CN 1015642 B CN1015642 B CN 1015642B
- Authority
- CN
- China
- Prior art keywords
- acid
- lubricating oils
- multifunctional additive
- alkyl
- component
- 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
- 229910052784 alkaline earth metal Inorganic materials 0.000 title abstract description 35
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000010687 lubricating oil Substances 0.000 claims abstract description 96
- 239000000203 mixture Substances 0.000 claims abstract description 70
- 239000000654 additive Substances 0.000 claims abstract description 57
- 230000000996 additive effect Effects 0.000 claims abstract description 57
- 239000002253 acid Substances 0.000 claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
- 150000002148 esters Chemical class 0.000 claims abstract description 17
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000000463 material Substances 0.000 claims description 56
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 37
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 31
- 239000005864 Sulphur Substances 0.000 claims description 31
- 235000021355 Stearic acid Nutrition 0.000 claims description 26
- 229910052791 calcium Inorganic materials 0.000 claims description 26
- 239000011575 calcium Substances 0.000 claims description 26
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 26
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 26
- 239000008117 stearic acid Substances 0.000 claims description 26
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 25
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 25
- 235000011089 carbon dioxide Nutrition 0.000 claims description 23
- 235000008733 Citrus aurantifolia Nutrition 0.000 claims description 22
- 235000011941 Tilia x europaea Nutrition 0.000 claims description 22
- 150000008065 acid anhydrides Chemical class 0.000 claims description 22
- 239000004571 lime Substances 0.000 claims description 22
- -1 alkyl phenol Chemical compound 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 19
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 15
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical group [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 11
- 239000001110 calcium chloride Substances 0.000 claims description 11
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 238000002156 mixing Methods 0.000 claims description 11
- 239000003513 alkali Substances 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 8
- 229910052749 magnesium Inorganic materials 0.000 claims description 8
- 239000011777 magnesium Substances 0.000 claims description 8
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
- 229910052788 barium Inorganic materials 0.000 claims description 7
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 7
- 150000001735 carboxylic acids Chemical class 0.000 claims description 7
- 229920002367 Polyisobutene Polymers 0.000 claims description 6
- 238000005987 sulfurization reaction Methods 0.000 claims description 5
- 229910001502 inorganic halide Inorganic materials 0.000 claims description 4
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000005466 alkylenyl group Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 239000001384 succinic acid Substances 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- 229920005652 polyisobutylene succinic anhydride Polymers 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 30
- 239000012141 concentrate Substances 0.000 abstract description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- 238000010348 incorporation Methods 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 239000000047 product Substances 0.000 description 66
- 238000005516 engineering process Methods 0.000 description 19
- 150000001342 alkaline earth metals Chemical class 0.000 description 14
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 150000001263 acyl chlorides Chemical class 0.000 description 9
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 7
- 238000006473 carboxylation reaction Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 235000019270 ammonium chloride Nutrition 0.000 description 5
- 230000021523 carboxylation Effects 0.000 description 5
- 239000013067 intermediate product Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910052712 strontium Inorganic materials 0.000 description 3
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229910052728 basic metal Inorganic materials 0.000 description 2
- 150000003818 basic metals Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229940031826 phenolate Drugs 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- YGYGASJNJTYNOL-CQSZACIVSA-N 3-[(4r)-2,2-dimethyl-1,1-dioxothian-4-yl]-5-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound C1CS(=O)(=O)C(C)(C)C[C@@H]1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(F)=CC=3)C=C12 YGYGASJNJTYNOL-CQSZACIVSA-N 0.000 description 1
- ZVHAANQOQZVVFD-UHFFFAOYSA-N 5-methylhexan-1-ol Chemical compound CC(C)CCCCO ZVHAANQOQZVVFD-UHFFFAOYSA-N 0.000 description 1
- IHLDEDLAZNFOJB-UHFFFAOYSA-N 6-octoxy-6-oxohexanoic acid Chemical compound CCCCCCCCOC(=O)CCCCC(O)=O IHLDEDLAZNFOJB-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- FKLSONDBCYHMOQ-UHFFFAOYSA-N 9E-dodecenoic acid Natural products CCC=CCCCCCCCC(O)=O FKLSONDBCYHMOQ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- 241000273930 Brevoortia tyrannus Species 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 235000021353 Lignoceric acid Nutrition 0.000 description 1
- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical class [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 1
- 241001125046 Sardina pilchardus Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- XZJZNZATFHOMSJ-KTKRTIGZSA-N cis-3-dodecenoic acid Chemical compound CCCCCCCC\C=C/CC(O)=O XZJZNZATFHOMSJ-KTKRTIGZSA-N 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
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- 238000010276 construction Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
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- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 1
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910021518 metal oxyhydroxide Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- YWWVWXASSLXJHU-WAYWQWQTSA-N myristoleic acid Chemical compound CCCC\C=C/CCCCCCCC(O)=O YWWVWXASSLXJHU-WAYWQWQTSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000004028 organic sulfates Chemical class 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-N ricinoleic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- QZZGJDVWLFXDLK-UHFFFAOYSA-N tetracosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(O)=O QZZGJDVWLFXDLK-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8628609 | 1986-11-29 | ||
| GB868628609A GB8628609D0 (en) | 1986-11-29 | 1986-11-29 | Lubricating oil additives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN87108239A CN87108239A (zh) | 1988-06-15 |
| CN1015642B true CN1015642B (zh) | 1992-02-26 |
Family
ID=10608200
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN87108344A Expired CN1012074B (zh) | 1986-11-29 | 1987-11-29 | 硫化烃基酚碱土金属盐添加剂浓缩物的生产方法 |
| CN87108239A Expired CN1015642B (zh) | 1986-11-29 | 1987-11-29 | 碱土金属烃基酚盐及其磁化衍生物，它们的制备和应用 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN87108344A Expired CN1012074B (zh) | 1986-11-29 | 1987-11-29 | 硫化烃基酚碱土金属盐添加剂浓缩物的生产方法 |
Country Status (20)
| Country | Link |
|---|---|
| EP (2) | EP0271262B2 (sv) |
| JP (2) | JPH0631383B2 (sv) |
| KR (2) | KR960010992B1 (sv) |
| CN (2) | CN1012074B (sv) |
| AT (2) | ATE79395T1 (sv) |
| AU (2) | AU608792B2 (sv) |
| BR (2) | BR8707550A (sv) |
| CA (2) | CA1305696C (sv) |
| DE (2) | DE3781118T3 (sv) |
| DK (2) | DK419788A (sv) |
| ES (2) | ES2051752T3 (sv) |
| FI (2) | FI93654C (sv) |
| GB (1) | GB8628609D0 (sv) |
| GR (2) | GR3006075T3 (sv) |
| IN (2) | IN172581B (sv) |
| MX (2) | MX169106B (sv) |
| NO (2) | NO176147C (sv) |
| SG (2) | SG101192G (sv) |
| WO (2) | WO1988003944A1 (sv) |
| ZA (2) | ZA878939B (sv) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8628609D0 (en) * | 1986-11-29 | 1987-01-07 | Bp Chemicals Additives | Lubricating oil additives |
| GB8814012D0 (en) * | 1988-06-14 | 1988-07-20 | Bp Chemicals Additives | Chemical process |
| GB8814008D0 (en) * | 1988-06-14 | 1988-07-20 | Bp Chemicals Additives | Lubricating oil additives |
| GB8814010D0 (en) * | 1988-06-14 | 1988-07-20 | Bp Chemicals Addivites Ltd | Lubricating oil additives |
| GB8814009D0 (en) * | 1988-06-14 | 1988-07-20 | Bp Chemicals Additives | Lubricating oil additives |
| GB8814013D0 (en) * | 1988-06-14 | 1988-07-20 | Bp Chemicals Additives | Chemical process |
| DK0385616T3 (da) * | 1989-02-25 | 1994-10-10 | Bp Chemicals Additives | Fremgangsmåde til fremstilling af et smøreolieadditivkoncentrat |
| GB8917094D0 (en) * | 1989-07-26 | 1989-09-13 | Bp Chemicals Additives | Chemical process |
| US5366648A (en) * | 1990-02-23 | 1994-11-22 | The Lubrizol Corporation | Functional fluids useful at high temperatures |
| GB9213723D0 (en) * | 1992-06-27 | 1992-08-12 | Bp Chemicals Additives | Process for the production of lubricating oil additives |
| TW277057B (sv) * | 1993-08-25 | 1996-06-01 | Cosmo Sogo Kenkyusho Kk | |
| JP2737096B2 (ja) * | 1993-08-25 | 1998-04-08 | 株式会社コスモ総合研究所 | 過塩基性硫化アルカリ土類金属フェネートの製造法 |
| GB9318810D0 (en) * | 1993-09-10 | 1993-10-27 | Bp Chem Int Ltd | Lubricating oil additives |
| GB9325132D0 (en) * | 1993-12-08 | 1994-02-09 | Bp Chemicals Additives | Lubricating oil additives |
| US6008166A (en) * | 1994-01-11 | 1999-12-28 | Lubrizol Adibis Holdings Limited | Detergent compositions |
| GB9400415D0 (en) * | 1994-01-11 | 1994-03-09 | Bp Chemicals Additives | Detergent compositions |
| GB9400417D0 (en) * | 1994-01-11 | 1994-03-09 | Bp Chemicals Additives | Lubricating oil composition |
| GB9411093D0 (en) | 1994-06-03 | 1994-07-27 | Bp Chemicals Additives | Detergent additives for lubricating oils, their preparation and use |
| US5529705A (en) * | 1995-03-17 | 1996-06-25 | Chevron Chemical Company | Methods for preparing normal and overbased phenates |
| CA2183906A1 (en) * | 1995-08-23 | 1997-02-24 | Christopher S. Fridia | Production of low fine sediment high tbn phenate stearate |
| EP0778336A1 (en) * | 1995-12-08 | 1997-06-11 | Cosmo Research Institute | Petroleum additive having excellent storage stability and heat stability comprising an alkaline earth metal salt of aromatic hydroxycarboxylic acid or a sulfurized mixture thereof. |
| GB9611317D0 (en) | 1996-05-31 | 1996-08-07 | Exxon Chemical Patents Inc | Overbased metal-containing detergents |
| GB9611316D0 (en) * | 1996-05-31 | 1996-08-07 | Exxon Chemical Patents Inc | Overbased metal-containing detergents |
| GB9611424D0 (en) * | 1996-05-31 | 1996-08-07 | Exxon Chemical Patents Inc | Overbased metal-containing detergents |
| US5728657A (en) * | 1996-08-20 | 1998-03-17 | Chevron Chemical Company | Production of low fine sediment high TBN phenate stearate |
| EP0989178A4 (en) * | 1997-05-07 | 2000-09-13 | Cosmo Sogo Kenkyusho Kk | LUBRICATING OIL COMPOSITION, HYPERBASIC ALKALINE EARTH METAL SULFIDE PHENATE CONCENTRATE FOR USE IN THE PREPARATION OF THIS COMPOSITION AND PROCESS FOR PREPARING THE CONCENTRATE |
| US5942476A (en) * | 1998-06-03 | 1999-08-24 | Chevron Chemical Company | Low-viscosity highly overbased phenate-carboxylate |
| US6348438B1 (en) | 1999-06-03 | 2002-02-19 | Chevron Oronite S.A. | Production of high BN alkaline earth metal single-aromatic ring hydrocarbyl salicylate-carboxylate |
| EP1710294B1 (en) | 2005-04-06 | 2013-03-06 | Infineum International Limited | A method of improving the stability or compatibility of a detergent |
| EP1743933B1 (en) | 2005-07-14 | 2019-10-09 | Infineum International Limited | A use to improve the compatibility of an overbased detergent with friction modifiers in a lubricating oil composition |
| US20080153723A1 (en) | 2006-12-20 | 2008-06-26 | Chevron Oronite Company Llc | Diesel cylinder lubricant oil composition |
| SG178205A1 (en) | 2009-08-06 | 2012-03-29 | Lubrizol Corp | Asphaltene dispersant containing lubricating compositions |
| EP2507347A1 (en) | 2009-11-30 | 2012-10-10 | The Lubrizol Corporation | Methods of controlling sulfur trioxide levels in internal combustion engines |
| EP2507349B1 (en) | 2009-11-30 | 2020-06-10 | The Lubrizol Corporation | Stabilized blends containing friction modifiers |
| CA2782216A1 (en) | 2009-11-30 | 2011-06-03 | The Lubrizol Corporation | Stabilized blends containing friction modifiers |
| BR112013015860A2 (pt) | 2010-12-21 | 2016-09-13 | Lubrizol Corp | composição lubrificante contendo um detergente |
| EP2673347B1 (en) | 2011-02-09 | 2018-09-12 | The Lubrizol Corporation | Asphaltene dispersant containing lubricating compositions |
| JP5840233B2 (ja) | 2011-02-17 | 2016-01-06 | ザ ルブリゾル コーポレイションＴｈｅ Ｌｕｂｒｉｚｏｌ Ｃｏｒｐｏｒａｔｉｏｎ | 良好なｔｂｎ保持率を有する潤滑剤 |
| DK2607462T3 (da) | 2011-12-20 | 2014-03-31 | Infineum Int Ltd | Smøring af skibsmotor |
| CA2863950C (en) * | 2012-02-08 | 2022-06-07 | The Lubrizol Corporation | Method for preparing a sulfurized alkaline earth metal dodecylphenate |
| EP2674474B1 (en) * | 2012-06-13 | 2015-09-09 | Infineum International Limited | Phenate detergent preparation |
| CA2909704C (en) | 2013-04-17 | 2021-11-16 | The Lubrizol Corporation | 2-stroke internal combustion engine cylinder liner lubricating composition |
| NZ725495A (en) * | 2014-04-02 | 2020-05-29 | Franck Natali | Doped rare earth nitride materials and devices comprising same |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4328111A (en) * | 1978-11-20 | 1982-05-04 | Standard Oil Company (Indiana) | Modified overbased sulfonates and phenates |
| BR8302526A (pt) * | 1982-05-14 | 1984-01-17 | Exxon Research Engineering Co | Processo para preparar um concentrado de aditivo para incoroporacao a uma composicao de oleo lubrificante e composicao de oleo lubrificante |
| CA1246615A (en) * | 1982-05-22 | 1988-12-13 | Charles Cane | Process for the production of alkaline earth metal alkyl phenates |
| ZA833532B (en) * | 1982-05-22 | 1984-12-24 | Orobis Ltd | Process for the production of either an alkaline earth metal alkyl phenate or a sulphurised alkaline earth metal alkyl phenate |
| FR2549080B1 (fr) * | 1983-07-11 | 1986-04-04 | Orogil | Procede de preparation d'additifs detergents-dispersants de tres haute alcalinite a base de calcium et additifs detergents-dispersants pour huiles lubrifiantes ainsi obtenus |
| GB8628609D0 (en) * | 1986-11-29 | 1987-01-07 | Bp Chemicals Additives | Lubricating oil additives |
-
1986
- 1986-11-29 GB GB868628609A patent/GB8628609D0/en active Pending
-
1987
- 1987-11-26 JP JP62507102A patent/JPH0631383B2/ja not_active Expired - Fee Related
- 1987-11-26 ES ES87310461T patent/ES2051752T3/es not_active Expired - Lifetime
- 1987-11-26 KR KR1019880700896A patent/KR960010992B1/ko not_active IP Right Cessation
- 1987-11-26 BR BR8707550A patent/BR8707550A/pt not_active IP Right Cessation
- 1987-11-26 BR BR8707551A patent/BR8707551A/pt not_active IP Right Cessation
- 1987-11-26 KR KR1019880700889A patent/KR960010991B1/ko not_active IP Right Cessation
- 1987-11-26 AT AT87310460T patent/ATE79395T1/de not_active IP Right Cessation
- 1987-11-26 AT AT87310461T patent/ATE79396T1/de not_active IP Right Cessation
- 1987-11-26 WO PCT/GB1987/000847 patent/WO1988003944A1/en active IP Right Grant
- 1987-11-26 AU AU82380/87A patent/AU608792B2/en not_active Ceased
- 1987-11-26 ES ES87310460T patent/ES2051751T3/es not_active Expired - Lifetime
- 1987-11-26 EP EP87310460A patent/EP0271262B2/en not_active Expired - Lifetime
- 1987-11-26 EP EP87310461A patent/EP0273588B2/en not_active Expired - Lifetime
- 1987-11-26 DE DE3781118T patent/DE3781118T3/de not_active Expired - Lifetime
- 1987-11-26 JP JP62507103A patent/JPH0631384B2/ja not_active Expired - Fee Related
- 1987-11-26 WO PCT/GB1987/000848 patent/WO1988003945A1/en active IP Right Grant
- 1987-11-26 DE DE3781126T patent/DE3781126T3/de not_active Expired - Fee Related
- 1987-11-26 AU AU82372/87A patent/AU609075B2/en not_active Ceased
- 1987-11-27 ZA ZA878939A patent/ZA878939B/xx unknown
- 1987-11-27 CA CA000552952A patent/CA1305696C/en not_active Expired - Lifetime
- 1987-11-27 CA CA000552953A patent/CA1305697C/en not_active Expired - Lifetime
- 1987-11-27 ZA ZA878938A patent/ZA878938B/xx unknown
- 1987-11-29 CN CN87108344A patent/CN1012074B/zh not_active Expired
- 1987-11-29 CN CN87108239A patent/CN1015642B/zh not_active Expired
- 1987-11-30 MX MX009654A patent/MX169106B/es unknown
- 1987-11-30 IN IN1019DE1987 patent/IN172581B/en unknown
- 1987-11-30 IN IN1018/DEL/87A patent/IN169547B/en unknown
- 1987-11-30 MX MX009636A patent/MX169105B/es unknown
-
1988
- 1988-07-25 FI FI883503A patent/FI93654C/sv not_active IP Right Cessation
- 1988-07-25 FI FI883502A patent/FI93653C/sv not_active IP Right Cessation
- 1988-07-27 DK DK419788A patent/DK419788A/da not_active Application Discontinuation
- 1988-07-27 DK DK198804198A patent/DK175287B1/da not_active IP Right Cessation
- 1988-07-28 NO NO883349A patent/NO176147C/no unknown
- 1988-07-28 NO NO883348A patent/NO302763B1/no unknown
-
1992
- 1992-10-05 SG SG1011/92A patent/SG101192G/en unknown
- 1992-10-05 SG SG1010/92A patent/SG101092G/en unknown
- 1992-10-26 GR GR920402404T patent/GR3006075T3/el unknown
- 1992-10-29 GR GR920402433T patent/GR3006112T3/el unknown
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Free format text: CORRECT: PATENTEE; FROM: BPCHEMICAL CO., LTD. TO: LOUBOURIZZO· RODEBIS HOLDINGS (UK) LIMITED |
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