DE3781126T3 - Geschwefelt Erdalkalimetallalkylphenolate, ihre Herstellung und ihre Verwendung. - Google Patents
Geschwefelt Erdalkalimetallalkylphenolate, ihre Herstellung und ihre Verwendung.Info
- Publication number
- DE3781126T3 DE3781126T3 DE3781126T DE3781126T DE3781126T3 DE 3781126 T3 DE3781126 T3 DE 3781126T3 DE 3781126 T DE3781126 T DE 3781126T DE 3781126 T DE3781126 T DE 3781126T DE 3781126 T3 DE3781126 T3 DE 3781126T3
- Authority
- DE
- Germany
- Prior art keywords
- concentrate
- process according
- alkaline earth
- added
- earth metal
- 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 - Fee Related
Links
- 229910052784 alkaline earth metal Inorganic materials 0.000 title claims abstract description 53
- 238000002360 preparation method Methods 0.000 title description 8
- 239000000203 mixture Substances 0.000 claims abstract description 86
- 239000012141 concentrate Substances 0.000 claims abstract description 79
- 239000010687 lubricating oil Substances 0.000 claims abstract description 60
- 239000000654 additive Substances 0.000 claims abstract description 27
- 230000000996 additive effect Effects 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 21
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 238000010348 incorporation Methods 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 104
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 75
- 238000000034 method Methods 0.000 claims description 72
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 56
- 239000011575 calcium Substances 0.000 claims description 55
- 229910052791 calcium Inorganic materials 0.000 claims description 54
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 52
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 40
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 38
- 239000011593 sulfur Substances 0.000 claims description 35
- 235000021355 Stearic acid Nutrition 0.000 claims description 34
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 34
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 34
- 239000008117 stearic acid Substances 0.000 claims description 34
- 229910052717 sulfur Inorganic materials 0.000 claims description 34
- 239000001569 carbon dioxide Substances 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 235000008733 Citrus aurantifolia Nutrition 0.000 claims description 16
- 235000011941 Tilia x europaea Nutrition 0.000 claims description 16
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 16
- 239000004571 lime Substances 0.000 claims description 16
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical group [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 14
- 239000001110 calcium chloride Substances 0.000 claims description 14
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 14
- 150000007513 acids Chemical class 0.000 claims description 12
- -1 alkylene glycol alkyl ether Chemical class 0.000 claims description 12
- 239000000376 reactant Substances 0.000 claims description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
- 150000001735 carboxylic acids Chemical class 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 150000008065 acid anhydrides Chemical class 0.000 claims description 7
- 150000005215 alkyl ethers Chemical class 0.000 claims description 7
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 6
- 229910052749 magnesium Inorganic materials 0.000 claims description 6
- 239000011777 magnesium Substances 0.000 claims description 6
- 150000005846 sugar alcohols Polymers 0.000 claims description 6
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 claims description 5
- 229910052788 barium Inorganic materials 0.000 claims description 5
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 229910001502 inorganic halide Inorganic materials 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 230000001050 lubricating effect Effects 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 22
- 125000003342 alkenyl group Chemical group 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
- 239000000047 product Substances 0.000 description 98
- 238000001914 filtration Methods 0.000 description 39
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 12
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 10
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 239000005864 Sulphur Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 235000021357 Behenic acid Nutrition 0.000 description 5
- 229940116226 behenic acid Drugs 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- 235000021314 Palmitic acid Nutrition 0.000 description 4
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 238000002485 combustion reaction Methods 0.000 description 4
- 150000002431 hydrogen Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 4
- 239000003784 tall oil Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ZVHAANQOQZVVFD-UHFFFAOYSA-N 5-methylhexan-1-ol Chemical compound CC(C)CCCCO ZVHAANQOQZVVFD-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- 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
- 235000019484 Rapeseed oil Nutrition 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 239000010689 synthetic lubricating oil Substances 0.000 description 3
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 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
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 1
- KDUGNDDZXPJVCS-UHFFFAOYSA-N 6-oxo-6-tridecoxyhexanoic acid Chemical compound CCCCCCCCCCCCCOC(=O)CCCCC(O)=O KDUGNDDZXPJVCS-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 229910021532 Calcite Inorganic materials 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000252203 Clupea harengus Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241001125046 Sardina pilchardus Species 0.000 description 1
- 241001312238 Scindapsus Species 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 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
- 239000000292 calcium oxide Substances 0.000 description 1
- 229940087373 calcium oxide Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 150000005218 dimethyl ethers Chemical class 0.000 description 1
- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000002816 fuel additive 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
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 235000019514 herring Nutrition 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
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000006080 lead scavenger Substances 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000314 lubricant Substances 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
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-N methyl hydrogen carbonate Chemical compound COC(O)=O CXHHBNMLPJOKQD-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 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
- 239000002540 palm oil Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005652 polyisobutylene succinic anhydride Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
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)
- Liquid Carbonaceous Fuels (AREA)
- Catalysts (AREA)
- Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB868628609A GB8628609D0 (en) | 1986-11-29 | 1986-11-29 | Lubricating oil additives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE3781126D1 DE3781126D1 (de) | 1992-09-17 |
| DE3781126T2 DE3781126T2 (de) | 1993-03-04 |
| DE3781126T3 true DE3781126T3 (de) | 2001-08-02 |
Family
ID=10608200
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3781118T Expired - Lifetime DE3781118T3 (de) | 1986-11-29 | 1987-11-26 | Erdalkalimetallalkylphenolate, ihre geschwefelten Derivate, ihre Herstellung und ihre Verwendung. |
| DE3781126T Expired - Fee Related DE3781126T3 (de) | 1986-11-29 | 1987-11-26 | Geschwefelt Erdalkalimetallalkylphenolate, ihre Herstellung und ihre Verwendung. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3781118T Expired - Lifetime DE3781118T3 (de) | 1986-11-29 | 1987-11-26 | Erdalkalimetallalkylphenolate, ihre geschwefelten Derivate, ihre Herstellung und ihre Verwendung. |
Country Status (20)
Families Citing this family (44)
| 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 |
| 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 |
| GB8814008D0 (en) * | 1988-06-14 | 1988-07-20 | Bp Chemicals Additives | Lubricating oil additives |
| 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 |
| 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 |
| TW277057B (enrdf_load_stackoverflow) * | 1993-08-25 | 1996-06-01 | Cosmo Sogo Kenkyusho Kk | |
| 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 |
| 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 |
| WO1998050500A1 (fr) * | 1997-05-07 | 1998-11-12 | Cosmo Research Institute | Composition d'huile lubrifiante, concentre de phenate de sulfure de metal alcalino-terreux hyperbasique utilise dans la preparation de cette composition et procede de preparation du concentre |
| 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 |
| USD551819S1 (en) | 2006-05-30 | 2007-09-25 | Kohs Stephen C | Fluid reservoir pole with dispensing wash head and squeegee |
| US20080153723A1 (en) | 2006-12-20 | 2008-06-26 | Chevron Oronite Company Llc | Diesel cylinder lubricant oil composition |
| RU2398814C1 (ru) * | 2009-01-23 | 2010-09-10 | Ирина Ефимовна Селезнева | Способ получения присадки к смазочным маслам |
| CN102575185B (zh) | 2009-08-06 | 2014-03-05 | 卢布里佐尔公司 | 含沥青质分散剂的润滑组合物 |
| WO2011066141A2 (en) | 2009-11-30 | 2011-06-03 | The Lubrizol Corporation | Stabilized blends containing friction modifiers |
| EP2507350B1 (en) | 2009-11-30 | 2018-06-13 | The Lubrizol Corporation | Use of stabilized blends containing friction modifiers |
| US20130098322A1 (en) | 2009-11-30 | 2013-04-25 | The Lubrizol Corporation | Methods of Controlling Sulfur Trioxide Levels in Internal Combustion Engines |
| JP2014500387A (ja) | 2010-12-21 | 2014-01-09 | ザ ルブリゾル コーポレイション | 清浄剤を含む潤滑組成物 |
| CA2826918A1 (en) | 2011-02-09 | 2012-08-16 | The Lubrizol Corporation | Asphaltene dispersant containing lubricating compositions |
| CN103476910B (zh) | 2011-02-17 | 2017-08-08 | 路博润公司 | 具有良好tbn保持力的润滑剂 |
| ES2463417T3 (es) | 2011-12-20 | 2014-05-27 | Infineum International Limited | Lubricación de motores marinos |
| CN104540842B (zh) * | 2012-02-08 | 2017-09-22 | 路博润公司 | 制备硫化碱土金属十二烷基酚盐的方法 |
| EP2674474B1 (en) * | 2012-06-13 | 2015-09-09 | Infineum International Limited | Phenate detergent preparation |
| EP2986694B1 (en) | 2013-04-17 | 2020-03-18 | The Lubrizol Corporation | Method of lubricating a 2-stroke internal combustion engine cylinder liner and piston |
| KR102328525B1 (ko) * | 2014-04-02 | 2021-11-19 | 프랭크 나탈리 | 도핑된 희토류 니트라이드 물질 및 이를 포함하는 장치 |
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 |
| EP0094814B1 (en) * | 1982-05-14 | 1989-04-19 | Exxon Research And Engineering Company | Lubricating oil additives |
| 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 AU AU82372/87A patent/AU609075B2/en not_active Ceased
- 1987-11-26 AT AT87310460T patent/ATE79395T1/de not_active IP Right Cessation
- 1987-11-26 BR BR8707550A patent/BR8707550A/pt not_active IP Right Cessation
- 1987-11-26 JP JP62507102A patent/JPH0631383B2/ja not_active Expired - Fee Related
- 1987-11-26 JP JP62507103A patent/JPH0631384B2/ja not_active Expired - Fee Related
- 1987-11-26 AT AT87310461T patent/ATE79396T1/de not_active IP Right Cessation
- 1987-11-26 ES ES87310460T patent/ES2051751T3/es not_active Expired - Lifetime
- 1987-11-26 KR KR1019880700889A patent/KR960010991B1/ko not_active Expired - Fee Related
- 1987-11-26 DE DE3781118T patent/DE3781118T3/de not_active Expired - Lifetime
- 1987-11-26 AU AU82380/87A patent/AU608792B2/en not_active Ceased
- 1987-11-26 WO PCT/GB1987/000848 patent/WO1988003945A1/en active IP Right Grant
- 1987-11-26 EP EP87310460A patent/EP0271262B2/en not_active Expired - Lifetime
- 1987-11-26 DE DE3781126T patent/DE3781126T3/de not_active Expired - Fee Related
- 1987-11-26 BR BR8707551A patent/BR8707551A/pt not_active IP Right Cessation
- 1987-11-26 WO PCT/GB1987/000847 patent/WO1988003944A1/en active IP Right Grant
- 1987-11-26 KR KR1019880700896A patent/KR960010992B1/ko not_active Expired - Fee Related
- 1987-11-26 EP EP87310461A patent/EP0273588B2/en not_active Expired - Lifetime
- 1987-11-26 ES ES87310461T patent/ES2051752T3/es not_active Expired - Lifetime
- 1987-11-27 CA CA000552952A patent/CA1305696C/en not_active Expired - Lifetime
- 1987-11-27 ZA ZA878938A patent/ZA878938B/xx unknown
- 1987-11-27 ZA ZA878939A patent/ZA878939B/xx unknown
- 1987-11-27 CA CA000552953A patent/CA1305697C/en not_active Expired - Lifetime
- 1987-11-29 CN CN87108239A patent/CN1015642B/zh not_active Expired
- 1987-11-29 CN CN87108344A patent/CN1012074B/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 FI883502A patent/FI93653C/fi not_active IP Right Cessation
- 1988-07-25 FI FI883503A patent/FI93654C/fi 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 SG1010/92A patent/SG101092G/en unknown
- 1992-10-05 SG SG1011/92A patent/SG101192G/en unknown
- 1992-10-26 GR GR920402404T patent/GR3006075T3/el unknown
- 1992-10-29 GR GR920402433T patent/GR3006112T3/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3781126T3 (de) | Geschwefelt Erdalkalimetallalkylphenolate, ihre Herstellung und ihre Verwendung. | |
| DE68921024T3 (de) | Verfahren zur Herstellung eines Schmieröladditivkonzentrats. | |
| DE69009236T2 (de) | Verfahren zur Herstellung eines Zusatzkonzentrats für Schmieröle. | |
| DE69726277T2 (de) | Überbasische metallenthaltende detergens | |
| DE68908039T2 (de) | Verfahren zur Herstellung eines Schmieröladditivkonzentrats. | |
| DE68918647T2 (de) | Verfahren zur Herstellung eines Schmieröladditivkonzentrats. | |
| DE69427080T2 (de) | Überbasische, alkylierte alkylsalicylate | |
| DE3382599T2 (de) | Verfahren zur herstellung von einem ueberbasischen geschwefelten erdalkalimetallalkylphenat. | |
| DE69003761T2 (de) | Verfahren zur Herstellung eines Schmierölzusatzkonzentrats. | |
| DE2653717A1 (de) | Verfahren zur herstellung eines ueberbasischen additivs zu schmieroelen | |
| US6090759A (en) | Alkaline earth metal hydrocarbyl phenates, their sulphurized derivatives, their production and use thereof | |
| DE68928508T2 (de) | Verfahren zur Herstellung eines Schmieröl-Additivkonzentrats | |
| US6090760A (en) | Sulphurized alkaline earth metal hydrocarbyl phenates, their production and use thereof | |
| DE69605771T2 (de) | Sulfonate mit niedriger basizität | |
| DE69327821T2 (de) | Verfahren zur Herstellung eines geschwefeltes Erdalkalimetallalkylphenat enthaltenden Additivkonzentrats | |
| DE69714141T2 (de) | Verfahren zur Herstellung von normalen und überbasischen Phenolaten | |
| DE69513056T2 (de) | Detergentzusammensetzung enthaltend überbasisches Phenolat | |
| DE69605772T2 (de) | Magnesium niedrigbasische sulphonate | |
| DE69827625T2 (de) | Verfahren zur Herstellung von Erdalkalimetall-Salzen mit hoher Basizität, insbesondere von einem an einem Ring gebundenen Hydrocarbylsalicylat-carboxylat | |
| DE69609882T2 (de) | Verfahren zur Herstellung von normalen und überbasischen Phenolaten | |
| DE69611863T2 (de) | Überbasische Metallcalixarate, ihre Herstellung und diese enthaltende Schmierölzusammensetzungen | |
| DE68921107T2 (de) | Verfahren zur Herstellung eines Schmieröladditivkonzentrats. | |
| DE69534586T2 (de) | Überbasische Metallsalze, deren Herstellung und Verwendung | |
| DE69430358T2 (de) | Erdalkalimetall-Hydrocarbylsalicylat-Konzentrate, deren Herstellung und Verwendung | |
| DE2622839C2 (de) | Verfahren zur Herstellung von Detergent-Additiven und diese Detergent-Additive enthaltendes Schmieröl |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8363 | Opposition against the patent | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: LUBRIZOL ADIBIS HOLDINGS (UK) LTD., WIRRAL, MERSEY |
|
| 8366 | Restricted maintained after opposition proceedings | ||
| 8339 | Ceased/non-payment of the annual fee |