DK175287B1 - Sulfurerede jordalkalimetalhydrocarbylphenater, deres fremstilling og anvendelse - Google Patents
Sulfurerede jordalkalimetalhydrocarbylphenater, deres fremstilling og anvendelse Download PDFInfo
- Publication number
- DK175287B1 DK175287B1 DK198804198A DK419888A DK175287B1 DK 175287 B1 DK175287 B1 DK 175287B1 DK 198804198 A DK198804198 A DK 198804198A DK 419888 A DK419888 A DK 419888A DK 175287 B1 DK175287 B1 DK 175287B1
- Authority
- DK
- Denmark
- Prior art keywords
- weight
- concentrate
- tbn
- alkaline earth
- lubricating oil
- Prior art date
Links
- 229910052784 alkaline earth metal Inorganic materials 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title description 9
- 239000000203 mixture Substances 0.000 claims abstract description 90
- 239000012141 concentrate Substances 0.000 claims abstract description 72
- 239000010687 lubricating oil Substances 0.000 claims abstract description 55
- 239000002253 acid Substances 0.000 claims abstract description 23
- 239000000654 additive Substances 0.000 claims abstract description 22
- 230000000996 additive effect Effects 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- 238000010348 incorporation Methods 0.000 claims abstract description 11
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 76
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 70
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 56
- 239000011575 calcium Substances 0.000 claims description 55
- 229910052791 calcium Inorganic materials 0.000 claims description 54
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 48
- 230000008569 process Effects 0.000 claims description 43
- 239000011593 sulfur Substances 0.000 claims description 43
- 229910052717 sulfur Inorganic materials 0.000 claims description 42
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 41
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 34
- 235000021355 Stearic acid Nutrition 0.000 claims description 33
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 33
- 239000008117 stearic acid Substances 0.000 claims description 33
- 238000007792 addition Methods 0.000 claims description 30
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 29
- 239000001569 carbon dioxide Substances 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 20
- -1 alkylene glycol alkyl ether Chemical class 0.000 claims description 16
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 16
- 235000008733 Citrus aurantifolia Nutrition 0.000 claims description 15
- 235000011941 Tilia x europaea Nutrition 0.000 claims description 15
- 239000004571 lime Substances 0.000 claims description 15
- 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
- 239000002585 base Substances 0.000 claims description 13
- 150000007513 acids Chemical class 0.000 claims description 12
- 150000001735 carboxylic acids Chemical class 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
- 150000008065 acid anhydrides Chemical class 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 229910052749 magnesium Inorganic materials 0.000 claims description 6
- 239000011777 magnesium Substances 0.000 claims description 6
- 239000000376 reactant 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
- 150000005215 alkyl ethers Chemical class 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
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 5
- 230000001050 lubricating effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 229910001502 inorganic halide Inorganic materials 0.000 claims description 3
- 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
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 24
- 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 description 4
- 125000003342 alkenyl group Chemical group 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 77
- 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
- 239000012043 crude product Substances 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 6
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- 239000003784 tall oil Substances 0.000 description 4
- 235000021357 Behenic acid Nutrition 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
- 235000021314 Palmitic acid Nutrition 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
- 229940116226 behenic acid Drugs 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 3
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- ZVHAANQOQZVVFD-UHFFFAOYSA-N 5-methylhexan-1-ol Chemical compound CC(C)CCCCO ZVHAANQOQZVVFD-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000003513 alkali Substances 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
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 235000011116 calcium hydroxide Nutrition 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 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
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 229910052753 mercury Inorganic materials 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
- 229920005652 polyisobutylene succinic anhydride Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000010689 synthetic lubricating oil Substances 0.000 description 2
- 230000007306 turnover Effects 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
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 1
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
- 101150042514 B1 gene Proteins 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
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 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
- 229920000742 Cotton Polymers 0.000 description 1
- 241000196324 Embryophyta 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
- 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
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241001125046 Sardina pilchardus 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
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 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
- 238000013459 approach Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000004429 atom Chemical group 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
- 210000001217 buttock Anatomy 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- 229940087373 calcium oxide Drugs 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 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
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 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
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- FARYTWBWLZAXNK-WAYWQWQTSA-N ethyl (z)-3-(methylamino)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)NC FARYTWBWLZAXNK-WAYWQWQTSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 239000004519 grease Substances 0.000 description 1
- 235000019514 herring Nutrition 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 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 Chemical class 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 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
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 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
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product 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
- 125000001424 substituent group Chemical group 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
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009736 wetting Methods 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
- 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
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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8628609 | 1986-11-29 | ||
| GB868628609A GB8628609D0 (en) | 1986-11-29 | 1986-11-29 | Lubricating oil additives |
| PCT/GB1987/000848 WO1988003945A1 (en) | 1986-11-29 | 1987-11-26 | Sulphurised alkaline earth metal hydrocarbyl phenates, their production and use thereof |
| GB8700848 | 1987-11-26 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK419888A DK419888A (da) | 1988-07-27 |
| DK419888D0 DK419888D0 (da) | 1988-07-27 |
| DK175287B1 true DK175287B1 (da) | 2004-08-09 |
Family
ID=10608200
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK419788A DK419788D0 (da) | 1986-11-29 | 1988-07-27 | Jordalkalimetalhydrocarbylphenater, deres sulfurerede derivater, deres fremstilling og anvendelse |
| DK198804198A DK175287B1 (da) | 1986-11-29 | 1988-07-27 | Sulfurerede jordalkalimetalhydrocarbylphenater, deres fremstilling og anvendelse |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK419788A DK419788D0 (da) | 1986-11-29 | 1988-07-27 | Jordalkalimetalhydrocarbylphenater, deres sulfurerede derivater, deres fremstilling og anvendelse |
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 |
| 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 |
| GB8814009D0 (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 |
| ATE106442T1 (de) * | 1989-02-25 | 1994-06-15 | Bp Chemicals Additives | Verfahren zur herstellung eines zusatzkonzentrats für schmieröle. |
| 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 (enrdf_load_html_response) * | 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 |
| GB9400417D0 (en) * | 1994-01-11 | 1994-03-09 | Bp Chemicals Additives | Lubricating oil composition |
| GB9400415D0 (en) * | 1994-01-11 | 1994-03-09 | Bp Chemicals Additives | Detergent compositions |
| 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 |
| WO2011017148A1 (en) | 2009-08-06 | 2011-02-10 | The Lubrizol Corporation | Asphaltene dispersant containing lubricating compositions |
| CN102725385B (zh) | 2009-11-30 | 2015-05-27 | 路博润公司 | 含有摩擦改进剂的稳定混合物 |
| CA2782212A1 (en) | 2009-11-30 | 2011-06-03 | The Lubrizol Corporation | Methods of controlling sulfur trioxide levels in internal combustion engines |
| WO2011066145A1 (en) | 2009-11-30 | 2011-06-03 | The Lubrizol Corporation | Stabilized blends containing friction modifiers |
| SG191274A1 (en) | 2010-12-21 | 2013-07-31 | Lubrizol Corp | Lubricating composition containing a detergent |
| CN103384717B (zh) | 2011-02-09 | 2016-08-17 | 路博润公司 | 含有沥青质分散剂的润滑组合物 |
| SG192724A1 (en) | 2011-02-17 | 2013-09-30 | Lubrizol Corp | Lubricants with good tbn retention |
| EP2607462B1 (en) | 2011-12-20 | 2014-03-12 | Infineum International Limited | Marine engine lubrication |
| SG10201607435RA (en) * | 2012-02-08 | 2016-10-28 | Lubrizol Corp | Method for Preparing a Sulfurized Alkaline Earth Metal Dodecylphenate |
| 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 |
| 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 KR KR1019880700889A patent/KR960010991B1/ko not_active Expired - Fee Related
- 1987-11-26 DE DE3781126T patent/DE3781126T3/de not_active Expired - Fee Related
- 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 DE DE3781118T patent/DE3781118T3/de not_active Expired - Lifetime
- 1987-11-26 WO PCT/GB1987/000848 patent/WO1988003945A1/en active IP Right Grant
- 1987-11-26 WO PCT/GB1987/000847 patent/WO1988003944A1/en active IP Right Grant
- 1987-11-26 AT AT87310460T patent/ATE79395T1/de not_active IP Right Cessation
- 1987-11-26 AU AU82372/87A patent/AU609075B2/en not_active Ceased
- 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 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 BR BR8707550A patent/BR8707550A/pt not_active IP Right Cessation
- 1987-11-26 AU AU82380/87A patent/AU608792B2/en not_active Ceased
- 1987-11-26 JP JP62507103A patent/JPH0631384B2/ja not_active Expired - Fee Related
- 1987-11-26 EP EP87310460A patent/EP0271262B2/en not_active Expired - Lifetime
- 1987-11-26 BR BR8707551A patent/BR8707551A/pt not_active IP Right Cessation
- 1987-11-27 CA CA000552952A patent/CA1305696C/en not_active Expired - Lifetime
- 1987-11-27 ZA ZA878939A patent/ZA878939B/xx unknown
- 1987-11-27 ZA ZA878938A patent/ZA878938B/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 MX009636A patent/MX169105B/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 MX009654A patent/MX169106B/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/DK419788D0/da not_active Application Discontinuation
- 1988-07-27 DK DK198804198A patent/DK175287B1/da not_active IP Right Cessation
- 1988-07-28 NO NO883348A patent/NO302763B1/no unknown
- 1988-07-28 NO NO883349A patent/NO176147C/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
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