CA1341002C - Alkyphenols d'un metal du groupe ii, sulfures, surbasique, de faible viscosite et de tbn eleve - Google Patents

Alkyphenols d'un metal du groupe ii, sulfures, surbasique, de faible viscosite et de tbn eleve

Info

Publication number: CA1341002C
Authority: CA; Canada
Prior art keywords: oil; group; weight percent; soluble; alkylphenol
Prior art date: 1986-08-08
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

Application number

CA000543119A

Other languages

English (en)

Inventor

Thomas V. Liston

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Chevron USA Inc

Original Assignee

Chevron Research and Technology Co

Priority date (The priority date 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 date listed.)

1986-08-08

Filing date

1987-07-28

Publication date

2000-05-30

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=25403296&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA1341002(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1987-07-28 Application filed by Chevron Research and Technology Co filed Critical Chevron Research and Technology Co

2000-05-30 Application granted granted Critical

2000-05-30 Publication of CA1341002C publication Critical patent/CA1341002C/fr

2017-05-30 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

229910052784 alkaline earth metal Inorganic materials 0.000 title claims abstract description 139
239000000203 mixture Substances 0.000 claims description 84
239000011575 calcium Substances 0.000 claims description 67
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 66
229910052791 calcium Inorganic materials 0.000 claims description 66
239000003921 oil Substances 0.000 claims description 66
239000010687 lubricating oil Substances 0.000 claims description 49
125000000217 alkyl group Chemical group 0.000 claims description 45
-1 hydrocarbyl sulfonate Chemical compound 0.000 claims description 44
125000004432 carbon atom Chemical group C* 0.000 claims description 36
239000002585 base Substances 0.000 claims description 31
230000001050 lubricating effect Effects 0.000 claims description 29
239000003054 catalyst Substances 0.000 claims description 27
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical group C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 claims description 22
238000000034 method Methods 0.000 claims description 20
238000005987 sulfurization reaction Methods 0.000 claims description 17
239000000654 additive Substances 0.000 claims description 15
239000012141 concentrate Substances 0.000 claims description 11
230000000996 additive effect Effects 0.000 claims description 10
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 7
229910052749 magnesium Inorganic materials 0.000 claims description 7
239000011777 magnesium Substances 0.000 claims description 7
229910052788 barium Inorganic materials 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 5
239000005077 polysulfide Substances 0.000 claims description 4
229920001021 polysulfide Polymers 0.000 claims description 4
150000008117 polysulfides Polymers 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
239000000376 reactant Substances 0.000 claims description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 113
238000006243 chemical reaction Methods 0.000 description 107
239000000047 product Substances 0.000 description 70
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 51
150000001336 alkenes Chemical class 0.000 description 47
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 45
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 38
239000011593 sulfur Substances 0.000 description 35
229910052717 sulfur Inorganic materials 0.000 description 35
230000001965 increasing effect Effects 0.000 description 32
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 30
239000005909 Kieselgur Substances 0.000 description 29
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 28
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 26
239000000920 calcium hydroxide Substances 0.000 description 26
235000011116 calcium hydroxide Nutrition 0.000 description 26
229910001861 calcium hydroxide Inorganic materials 0.000 description 26
229910002092 carbon dioxide Inorganic materials 0.000 description 23
239000001569 carbon dioxide Substances 0.000 description 19
238000001914 filtration Methods 0.000 description 17
229910052757 nitrogen Inorganic materials 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
229910052500 inorganic mineral Inorganic materials 0.000 description 15
235000010755 mineral Nutrition 0.000 description 15
239000011707 mineral Substances 0.000 description 15
238000013019 agitation Methods 0.000 description 14
230000000052 comparative effect Effects 0.000 description 14
239000013049 sediment Substances 0.000 description 14
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 14
238000002360 preparation method Methods 0.000 description 13
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
239000000243 solution Substances 0.000 description 11
KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 10
125000001183 hydrocarbyl group Chemical group 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
239000003085 diluting agent Substances 0.000 description 9
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 9
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 7
229940054266 2-mercaptobenzothiazole Drugs 0.000 description 7
159000000007 calcium salts Chemical class 0.000 description 7
230000003301 hydrolyzing effect Effects 0.000 description 7
229910052751 metal Inorganic materials 0.000 description 7
239000002184 metal Substances 0.000 description 7
150000004706 metal oxides Chemical class 0.000 description 7
229940014800 succinic anhydride Drugs 0.000 description 7
229960002317 succinimide Drugs 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
150000004703 alkoxides Chemical class 0.000 description 6
150000008064 anhydrides Chemical class 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
238000009472 formulation Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000000126 substance Substances 0.000 description 6
229920002554 vinyl polymer Polymers 0.000 description 6
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
239000005977 Ethylene Substances 0.000 description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000012267 brine Substances 0.000 description 5
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 5
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
239000000314 lubricant Substances 0.000 description 5
229910000000 metal hydroxide Inorganic materials 0.000 description 5
229920000768 polyamine Polymers 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 5
238000012360 testing method Methods 0.000 description 5
239000004711 α-olefin Substances 0.000 description 5
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 4
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
229920002367 Polyisobutene Polymers 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
125000002947 alkylene group Chemical group 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
239000001110 calcium chloride Substances 0.000 description 4
229910001628 calcium chloride Inorganic materials 0.000 description 4
235000011148 calcium chloride Nutrition 0.000 description 4
238000000502 dialysis Methods 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
238000010348 incorporation Methods 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 4
GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 3
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 3
239000004793 Polystyrene Substances 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229920004890 Triton X-100 Polymers 0.000 description 3
239000013504 Triton X-100 Substances 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000003729 cation exchange resin Substances 0.000 description 3
230000007423 decrease Effects 0.000 description 3
238000007865 diluting Methods 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
235000010446 mineral oil Nutrition 0.000 description 3
229920001281 polyalkylene Polymers 0.000 description 3
230000000379 polymerizing effect Effects 0.000 description 3
229920000098 polyolefin Polymers 0.000 description 3
229920002223 polystyrene Polymers 0.000 description 3
239000010802 sludge Substances 0.000 description 3
239000002966 varnish Substances 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
229920004897 Triton X-45 Polymers 0.000 description 2
JNVCSEDACVAATK-UHFFFAOYSA-L [Ca+2].[S-]SSS[S-] Chemical compound [Ca+2].[S-]SSS[S-] JNVCSEDACVAATK-UHFFFAOYSA-L 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
230000002152 alkylating effect Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
239000002199 base oil Substances 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
238000011161 development Methods 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
229910044991 metal oxide Inorganic materials 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
YOEWQQVKRJEPAE-UHFFFAOYSA-L succinylcholine chloride (anhydrous) Chemical class [Cl-].[Cl-].C[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C YOEWQQVKRJEPAE-UHFFFAOYSA-L 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
238000010998 test method Methods 0.000 description 2
239000013638 trimer Substances 0.000 description 2
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
JAEZSIYNWDWMMN-UHFFFAOYSA-N 1,1,3-trimethylthiourea Chemical compound CNC(=S)N(C)C JAEZSIYNWDWMMN-UHFFFAOYSA-N 0.000 description 1
WJECKFZULSWXPN-UHFFFAOYSA-N 1,2-didodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1CCCCCCCCCCCC WJECKFZULSWXPN-UHFFFAOYSA-N 0.000 description 1
BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 1
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
ZAXCZCOUDLENMH-UHFFFAOYSA-N 3,3,3-tetramine Chemical compound NCCCNCCCNCCCN ZAXCZCOUDLENMH-UHFFFAOYSA-N 0.000 description 1
QRYFCNPYGUORTK-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-yldisulfanyl)morpholine Chemical compound C1COCCN1SSC1=NC2=CC=CC=C2S1 QRYFCNPYGUORTK-UHFFFAOYSA-N 0.000 description 1
NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical class CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
VNMOWKHAHQJUJI-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-(2-iodo-5-methoxyphenyl)sulfanylpurin-6-amine Chemical compound COC1=CC=C(I)C(SC=2N(C3=NC=NC(N)=C3N=2)CCCNC(C)(C)C)=C1 VNMOWKHAHQJUJI-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
241000908596 Centistes Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 1
AIKKULXCBHRFOS-UHFFFAOYSA-N Formothion Chemical compound COP(=S)(OC)SCC(=O)N(C)C=O AIKKULXCBHRFOS-UHFFFAOYSA-N 0.000 description 1
241000283986 Lepus Species 0.000 description 1
KFFQABQEJATQAT-UHFFFAOYSA-N N,N'-dibutylthiourea Chemical compound CCCCNC(=S)NCCCC KFFQABQEJATQAT-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
241000282320 Panthera leo Species 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
244000171726 Scotch broom Species 0.000 description 1
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
241000534944 Thia Species 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
AOZDHFFNBZAHJF-UHFFFAOYSA-N [3-hexanoyloxy-2,2-bis(hexanoyloxymethyl)propyl] hexanoate Chemical compound CCCCCC(=O)OCC(COC(=O)CCCCC)(COC(=O)CCCCC)COC(=O)CCCCC AOZDHFFNBZAHJF-UHFFFAOYSA-N 0.000 description 1
JZVCWNCNWKURQG-UHFFFAOYSA-M [Zn+].CCCCOP([O-])(=S)SCCCC Chemical compound [Zn+].CCCCOP([O-])(=S)SCCCC JZVCWNCNWKURQG-UHFFFAOYSA-M 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000003973 alkyl amines Chemical group 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
230000003254 anti-foaming effect Effects 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
SAOKZLXYCUGLFA-UHFFFAOYSA-N bis(2-ethylhexyl) adipate Chemical compound CCCCC(CC)COC(=O)CCCCC(=O)OCC(CC)CCCC SAOKZLXYCUGLFA-UHFFFAOYSA-N 0.000 description 1
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
ZFXVRMSLJDYJCH-UHFFFAOYSA-N calcium magnesium Chemical compound [Mg].[Ca] ZFXVRMSLJDYJCH-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical class [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
JGIATAMCQXIDNZ-UHFFFAOYSA-N calcium sulfide Chemical compound [Ca]=S JGIATAMCQXIDNZ-UHFFFAOYSA-N 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000003599 detergent Substances 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
GHKVUVOPHDYRJC-UHFFFAOYSA-N didodecyl hexanedioate Chemical compound CCCCCCCCCCCCOC(=O)CCCCC(=O)OCCCCCCCCCCCC GHKVUVOPHDYRJC-UHFFFAOYSA-N 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
229940096818 dipentamethylenethiuram disulfide Drugs 0.000 description 1
PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
239000006260 foam Substances 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000010354 integration Effects 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
239000006078 metal deactivator Substances 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
238000005649 metathesis reaction Methods 0.000 description 1
XXEWNXXUIQCBKR-UHFFFAOYSA-N methylidenethiourea Chemical compound NC(=S)N=C XXEWNXXUIQCBKR-UHFFFAOYSA-N 0.000 description 1
150000005673 monoalkenes Chemical class 0.000 description 1
150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
239000010705 motor oil Substances 0.000 description 1
LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
KNBRWWCHBRQLNY-UHFFFAOYSA-N piperidine-1-carbothioylsulfanyl piperidine-1-carbodithioate Chemical compound C1CCCCN1C(=S)SSC(=S)N1CCCCC1 KNBRWWCHBRQLNY-UHFFFAOYSA-N 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
238000010926 purge Methods 0.000 description 1
102220015453 rs397517473 Human genes 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000007858 starting material 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
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
229960001124 trientine Drugs 0.000 description 1
WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 description 1
238000013022 venting Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc 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
- C10M159/24—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing sulfonic radicals
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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)

CA000543119A 1986-08-08 1987-07-28 Alkyphenols d'un metal du groupe ii, sulfures, surbasique, de faible viscosite et de tbn eleve Expired - Fee Related CA1341002C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US89459986A	1986-08-08	1986-08-08
US894,599		1986-08-08

Publications (1)

Publication Number	Publication Date
CA1341002C true CA1341002C (fr)	2000-05-30

Family

ID=25403296

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000543119A Expired - Fee Related CA1341002C (fr)	1986-08-08	1987-07-28	Alkyphenols d'un metal du groupe ii, sulfures, surbasique, de faible viscosite et de tbn eleve

Country Status (15)

Country	Link
EP (1)	EP0259974B2 (fr)
JP (1)	JPS6346297A (fr)
KR (1)	KR880002818A (fr)
CN (1)	CN1021345C (fr)
AU (1)	AU602343B2 (fr)
BR (1)	BR8704053A (fr)
CA (1)	CA1341002C (fr)
DE (1)	DE3785807T3 (fr)
DK (1)	DK410087A (fr)
ES (1)	ES2054677T3 (fr)
IN (1)	IN170575B (fr)
MX (1)	MX168483B (fr)
NO (1)	NO167659C (fr)
NZ (1)	NZ221128A (fr)
ZA (1)	ZA875686B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5391310A (en) *	1993-11-23	1995-02-21	Cincinnati Milacron Inc.	Sulfurized aqueous machining fluid composition
JP3454593B2 (ja) *	1994-12-27	2003-10-06	旭電化工業株式会社	潤滑油組成物
US7405185B2 (en)	2003-09-26	2008-07-29	Chevron Oronite Company Llc	Process for making Group II metal overbased sulfurized alkylphenols
ES2655116T3 (es) *	2006-09-19	2018-02-16	Infineum International Limited	Una composición de aceite lubricante
US8933002B2 (en) *	2011-11-10	2015-01-13	Chevron Oronite Company Llc	Lubricating oil compositions

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3178368A (en) *	1962-05-15	1965-04-13	California Research Corp	Process for basic sulfurized metal phenates
NL134001C (fr) *	1965-10-29
US3367867A (en) *	1966-01-04	1968-02-06	Chevron Res	Low-foaming overbased phenates
US3424679A (en) *	1966-08-15	1969-01-28	Chevron Res	Nonvicinal glycols in overbased phenate preparation
GB1144084A (en) *	1966-08-24	1969-03-05	Orobis Ltd	Improvements in or relating to lubricant additives
US3464970A (en) *	1967-03-13	1969-09-02	Maruzen Oil Co Ltd	Process for preparing over-based sulfurized calcium phenates
GB1280749A (en) *	1970-06-18	1972-07-05	Maruzen Oil Company Ltd	Process for preparation of over-based sulphurized phenates
US3801507A (en) *	1972-08-18	1974-04-02	Chevron Res	Sulfurized metal phenates
GB1429243A (en) *	1973-02-22	1976-03-24	Orobis Ltd	Overbased phenates
GB1551819A (en) *	1975-05-23	1979-09-05	Exxon Research Engineering Co	Production of basic magnesium detergent additives
US4104180A (en) *	1975-05-23	1978-08-01	Exxon Research & Engineering Co.	Production of overbased metal phenates
BE871932R (fr) *	1977-11-11	1979-05-10	Orobis Ltd	Additif pour huiles lubrifiantes forme par neutralisation d'un alkylphenol sulfure et d'une base de mannich
EP0094814B1 (fr) *	1982-05-14	1989-04-19	Exxon Research And Engineering Company	Additifs pour huile lubrifiante
FR2529226B1 (fr) *	1982-06-24	1987-01-16	Orogil	Procede de preparation d'alkylphenates sulfurises de metaux alcalino-terreux utilisables comme additifs pour huiles lubrifiantes
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
FR2587353B1 (fr) *	1985-09-17	1987-11-20	Orogil	Nouveaux additifs detergents-dispersants suralcalinises stables a l'hydrolyse pour huiles lubrifiantes et leur procede de preparation

1987
- 1987-07-20 NZ NZ221128A patent/NZ221128A/xx unknown
- 1987-07-28 CA CA000543119A patent/CA1341002C/fr not_active Expired - Fee Related
- 1987-07-31 AU AU76334/87A patent/AU602343B2/en not_active Ceased
- 1987-07-31 ZA ZA875686A patent/ZA875686B/xx unknown
- 1987-08-06 DK DK410087A patent/DK410087A/da not_active Application Discontinuation
- 1987-08-07 BR BR8704053A patent/BR8704053A/pt not_active Application Discontinuation
- 1987-08-07 MX MX026955A patent/MX168483B/es unknown
- 1987-08-07 EP EP87307025A patent/EP0259974B2/fr not_active Expired - Lifetime
- 1987-08-07 KR KR1019870008668A patent/KR880002818A/ko not_active Ceased
- 1987-08-07 ES ES87307025T patent/ES2054677T3/es not_active Expired - Lifetime
- 1987-08-07 JP JP62197989A patent/JPS6346297A/ja active Pending
- 1987-08-07 NO NO873316A patent/NO167659C/no unknown
- 1987-08-07 DE DE3785807T patent/DE3785807T3/de not_active Expired - Fee Related
- 1987-08-08 CN CN87105448A patent/CN1021345C/zh not_active Expired - Fee Related
1988
- 1988-01-05 IN IN05/MAS/88A patent/IN170575B/en unknown

Also Published As

Publication number	Publication date
DE3785807T2 (de)	1993-10-07
EP0259974B1 (fr)	1993-05-12
ES2054677T3 (es)	1994-08-16
NO167659B (no)	1991-08-19
NO873316L (no)	1988-02-09
KR880002818A (ko)	1988-05-11
DK410087D0 (da)	1987-08-06
DE3785807T3 (de)	1997-06-12
AU602343B2 (en)	1990-10-11
CN87105448A (zh)	1988-04-13
EP0259974A3 (en)	1988-08-10
IN170575B (fr)	1992-04-11
ZA875686B (en)	1988-04-27
DK410087A (da)	1988-02-09
MX168483B (es)	1993-05-26
EP0259974B2 (fr)	1997-03-26
NZ221128A (en)	1989-09-27
NO873316D0 (no)	1987-08-07
NO167659C (no)	1991-11-27
EP0259974A2 (fr)	1988-03-16
AU7633487A (en)	1988-02-11
JPS6346297A (ja)	1988-02-27
DE3785807D1 (de)	1993-06-17
CN1021345C (zh)	1993-06-23
BR8704053A (pt)	1988-04-05

Legal Events

Date	Code	Title	Description
2005-05-30	MKLA	Lapsed

Publication	Publication Date	Title
US4744921A (en)	1988-05-17	Methods for preparing, group II metal overbased sulfurized alkylphenols
US5024773A (en)	1991-06-18	Methods for preparing, group II metal overbased sulfurized alkylphenols
JP4763102B2 (ja)	2011-08-31	金属含有過塩基性清浄剤
CA1238345A (fr)	1988-06-21	Alcoyl(c in18 xx a c in24 xx)-catechols normalement liquides
US4965004A (en)	1990-10-23	Process for a borated detergent additive
EP0614963A1 (fr)	1994-09-14	Compositions de faible viscosité à base de sel surbasique de métal du groupe II d'alkylphenol sulfuré, le groupe alkyl contenant 16 à 22 carbones
EP0614962B1 (fr)	1999-01-13	Compositions de faible viscosité à base de sel surbasique de métal du groupe II d'alkylphenol sulfuré, le groupe alkyl contenant 12 à 22 carbones
US4435301A (en)	1984-03-06	Preparation of overbased magnesium phenates
JPH03166294A (ja)	1991-07-18	過塩基性化された硫化フェネート洗浄剤を合成する改良された方法
US4016093A (en)	1977-04-05	Metal alkylphenate sulfides of reduced corrosiveness and method of preparing same
CA1341002C (fr)	2000-05-30	Alkyphenols d'un metal du groupe ii, sulfures, surbasique, de faible viscosite et de tbn eleve
US4971710A (en)	1990-11-20	Methods for preparing, Group II metal overbased sulfurized alkylphenols
AU674573B2 (en)	1997-01-02	Lubricating oil compositions for railroad diesel engines
US3755170A (en)	1973-08-28	Preparation of highly basic alkylphenates and sulfurized alkyphenates
AU598769B2 (en)	1990-07-05	Succinimide complexes of borated alkyl catechols and lubricating oil compositions containing same
EP0031990B1 (fr)	1984-05-09	Composition d'huile lubrifiante, concentrat d'additif pour huile lubrifiante et procédé pour conférer des propriétés anti-corrosives à une huile lubrifiante
EP0011497B1 (fr)	1983-02-16	Composition d'huile lubrifiante et concentrat d'additif pour l'addition à de l'huile lubrifiante
US5160652A (en)	1992-11-03	Dialkylamine complexes of borated higher carbon number alkyl catechols and lubricating oil compositions containing the same
US4550197A (en)	1985-10-29	Overbased ortho-carboxy phenylphenone lubricating oil additives
EP0537840B1 (fr)	1996-07-17	Compositions lubrifiantes contenant des sels de métaux alcalino-terreux surbasiques d'acides hydroxyalkylsulphoniques
EP0574088B1 (fr)	1996-09-11	Sels des dérivés des acides mercaptocarboxyliques et leur utilisation comme additifs pour huiles lubrifiantes
CA1341005C (fr)	2000-05-30	Compositions combustibles et compositions d'huile lubrifiante contenant de tres longues chaines d'aminocurbamate d'alkylphenyl poly(oxyalkyline)
AU633481B2 (en)	1993-02-04	Lubricating oil compositions and fuel compositions containing substantially straight chain pinwheel alkylphenyl poly(oxypropylene) aminocarbamates
CA2096896A1 (fr)	1993-12-10	Sels de derives de l'acide mercaptocarboxylique et leur utilisation comme additifs dispersants
JPS6163632A (ja)	1986-04-01	モノアルキルカテコールを含む潤滑油組成物