CA1047506A - Sulphur containing lubricating oil additives - Google Patents
Sulphur containing lubricating oil additivesInfo
- Publication number
- CA1047506A CA1047506A CA220,916A CA220916A CA1047506A CA 1047506 A CA1047506 A CA 1047506A CA 220916 A CA220916 A CA 220916A CA 1047506 A CA1047506 A CA 1047506A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- lubricating composition
- thiabicyclo
- bis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims description 10
- 239000005864 Sulphur Substances 0.000 title abstract description 9
- 239000000654 additive Substances 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 239000000203 mixture Substances 0.000 claims abstract description 41
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 229920000642 polymer Polymers 0.000 claims abstract description 9
- -1 aralkyl xanthate Chemical compound 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- 230000001050 lubricating effect Effects 0.000 claims description 16
- 239000011593 sulfur Substances 0.000 claims description 10
- 150000002430 hydrocarbons Chemical group 0.000 claims description 8
- 239000003921 oil Substances 0.000 claims description 8
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 claims description 7
- 239000004912 1,5-cyclooctadiene Substances 0.000 claims description 7
- ZOLLIQAKMYWTBR-RYMQXAEESA-N cyclododecatriene Chemical compound C/1C\C=C\CC\C=C/CC\C=C\1 ZOLLIQAKMYWTBR-RYMQXAEESA-N 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- CHVJITGCYZJHLR-UHFFFAOYSA-N cyclohepta-1,3,5-triene Chemical compound C1C=CC=CC=C1 CHVJITGCYZJHLR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- KDUIUFJBNGTBMD-UHFFFAOYSA-N cyclooctatetraene Chemical compound C1=CC=CC=CC=C1 KDUIUFJBNGTBMD-UHFFFAOYSA-N 0.000 claims description 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 claims 2
- UHTPANGELWHLKJ-UHFFFAOYSA-N O-butyl (9-butoxycarbothioylsulfanyl-13-thiabicyclo[8.2.1]tridec-5-en-2-yl)sulfanylmethanethioate Chemical compound C(CCC)OC(=S)SC1C2CCC(C(CCC=CCC1)SC(=S)OCCCC)S2 UHTPANGELWHLKJ-UHFFFAOYSA-N 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 238000006116 polymerization reaction Methods 0.000 claims 2
- VETCNMQIFQTVFU-UHFFFAOYSA-N O-(2-ethylhexyl) [9-(2-ethylhexoxycarbothioylsulfanyl)-13-thiabicyclo[8.2.1]tridec-5-en-2-yl]sulfanylmethanethioate Chemical compound C(C)C(COC(=S)SC1C2CCC(C(CCC=CCC1)SC(=S)OCC(CCCC)CC)S2)CCCC VETCNMQIFQTVFU-UHFFFAOYSA-N 0.000 claims 1
- RBZZIABAQSKQKP-UHFFFAOYSA-N O-benzyl (9-phenylmethoxycarbothioylsulfanyl-13-thiabicyclo[8.2.1]tridec-5-en-2-yl)sulfanylmethanethioate Chemical compound C(C1=CC=CC=C1)OC(=S)SC1C2CCC(C(CCC=CCC1)SC(=S)OCC1=CC=CC=C1)S2 RBZZIABAQSKQKP-UHFFFAOYSA-N 0.000 claims 1
- VWKCZOBXGFAYQR-UHFFFAOYSA-N O-pentan-2-yl (9-pentan-2-yloxycarbothioylsulfanyl-13-thiabicyclo[8.2.1]tridec-5-en-2-yl)sulfanylmethanethioate Chemical compound CC(CCC)OC(=S)SC1C2CCC(C(CCC=CCC1)SC(=S)OC(CCC)C)S2 VWKCZOBXGFAYQR-UHFFFAOYSA-N 0.000 claims 1
- VLLDASMGPOHACW-UHFFFAOYSA-N O-propan-2-yl (9-propan-2-yloxycarbothioylsulfanyl-13-thiabicyclo[8.2.1]tridec-5-en-2-yl)sulfanylmethanethioate Chemical compound C(C)(C)OC(=S)SC1C2CCC(C(CCC=CCC1)SC(=S)OC(C)C)S2 VLLDASMGPOHACW-UHFFFAOYSA-N 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- UMFLQAGMYNBKTR-UHFFFAOYSA-N o-(2-ethylhexyl) [6-(2-ethylhexoxycarbothioylsulfanyl)-9-thiabicyclo[3.3.1]nonan-2-yl]sulfanylmethanethioate Chemical compound S1C2C(SC(=S)OCC(CC)CCCC)CCC1C(SC(=S)OCC(CC)CCCC)CC2 UMFLQAGMYNBKTR-UHFFFAOYSA-N 0.000 claims 1
- CJGVSCGBQLAEEV-UHFFFAOYSA-N o-benzyl (2-phenylmethoxycarbothioylsulfanyl-9-thiabicyclo[3.3.1]nonan-6-yl)sulfanylmethanethioate Chemical compound C1CC(C(CC2)SC(=S)OCC=3C=CC=CC=3)SC2C1SC(=S)OCC1=CC=CC=C1 CJGVSCGBQLAEEV-UHFFFAOYSA-N 0.000 claims 1
- LGVVCCSAKDMLMO-UHFFFAOYSA-N o-butyl (6-butoxycarbothioylsulfanyl-9-thiabicyclo[3.3.1]nonan-2-yl)sulfanylmethanethioate Chemical compound S1C2C(SC(=S)OCCCC)CCC1C(SC(=S)OCCCC)CC2 LGVVCCSAKDMLMO-UHFFFAOYSA-N 0.000 claims 1
- SJCOOXAUOGRANS-UHFFFAOYSA-N o-ethyl (6-ethoxycarbothioylsulfanyl-9-thiabicyclo[3.3.1]nonan-2-yl)sulfanylmethanethioate Chemical compound S1C2C(SC(=S)OCC)CCC1C(SC(=S)OCC)CC2 SJCOOXAUOGRANS-UHFFFAOYSA-N 0.000 claims 1
- FKADHWVRTVGYKN-UHFFFAOYSA-N o-propan-2-yl (6-propan-2-yloxycarbothioylsulfanyl-9-thiabicyclo[3.3.1]nonan-2-yl)sulfanylmethanethioate Chemical compound S1C2C(SC(=S)OC(C)C)CCC1C(SC(=S)OC(C)C)CC2 FKADHWVRTVGYKN-UHFFFAOYSA-N 0.000 claims 1
- 239000012991 xanthate Substances 0.000 abstract description 7
- 230000000269 nucleophilic effect Effects 0.000 abstract description 3
- 239000003879 lubricant additive Substances 0.000 abstract description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- VYXHVRARDIDEHS-QGTKBVGQSA-N (1z,5z)-cycloocta-1,5-diene Chemical compound C\1C\C=C/CC\C=C/1 VYXHVRARDIDEHS-QGTKBVGQSA-N 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 75
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 42
- 239000000047 product Substances 0.000 description 39
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 22
- 239000000460 chlorine Substances 0.000 description 21
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 20
- 238000004458 analytical method Methods 0.000 description 18
- 229910052801 chlorine Inorganic materials 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000543 intermediate Substances 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000010902 straw Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- QUZIEYDEASXPSN-UHFFFAOYSA-N 2,6-dichloro-9-thiabicyclo[3.3.1]nonane Chemical compound S1C2C(Cl)CCC1C(Cl)CC2 QUZIEYDEASXPSN-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 4
- 229960004592 isopropanol Drugs 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- DRLWTRZTIYZZNR-UHFFFAOYSA-N 2,9-dichloro-13-thiabicyclo[8.2.1]tridec-5-ene Chemical compound ClC1CCC=CCCC(Cl)C2CCC1S2 DRLWTRZTIYZZNR-UHFFFAOYSA-N 0.000 description 3
- 125000003963 dichloro group Chemical group Cl* 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 241000692870 Inachis io Species 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- SXIFNAOBIAIYJO-SXVCMZJPSA-N (1E,3E,7E)-cyclododeca-1,3,7-triene Chemical compound C/1=C\CCCC\C=C\C=C\CC\1 SXIFNAOBIAIYJO-SXVCMZJPSA-N 0.000 description 1
- ZOLLIQAKMYWTBR-MOLCZBCNSA-N (1z,5z,9z)-cyclododeca-1,5,9-triene Chemical compound C\1C\C=C/CC\C=C/CC\C=C/1 ZOLLIQAKMYWTBR-MOLCZBCNSA-N 0.000 description 1
- ORWQBKPSGDRPPA-UHFFFAOYSA-N 3-[2-[ethyl(methyl)amino]ethyl]-1h-indol-4-ol Chemical compound C1=CC(O)=C2C(CCN(C)CC)=CNC2=C1 ORWQBKPSGDRPPA-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FGLXICOLXZORLT-UHFFFAOYSA-N O-but-2-enyl (9-but-2-enoxycarbothioylsulfanyl-13-thiabicyclo[8.2.1]tridec-5-en-2-yl)sulfanylmethanethioate Chemical compound C(C=CC)OC(=S)SC1C2CCC(C(CCC=CCC1)SC(=S)OCC=CC)S2 FGLXICOLXZORLT-UHFFFAOYSA-N 0.000 description 1
- LKGQVRYHLHDAFG-UHFFFAOYSA-N O-octyl (9-cyano-13-thiabicyclo[8.2.1]tridec-5-en-1-yl)sulfanylmethanethioate Chemical compound C(CCCCCCC)OC(=S)SC12CCCC=CCCC(C(CC1)S2)C#N LKGQVRYHLHDAFG-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 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
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007866 anti-wear additive Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- OUGWQTNZGOBWTD-UHFFFAOYSA-N dichloromethane nonane Chemical compound C(Cl)Cl.CCCCCCCCC OUGWQTNZGOBWTD-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
- ZMWBGRXFDPJFGC-UHFFFAOYSA-M potassium;propan-2-yloxymethanedithioate Chemical compound [K+].CC(C)OC([S-])=S ZMWBGRXFDPJFGC-UHFFFAOYSA-M 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- VDFGUEPMNNLWOZ-UHFFFAOYSA-N tridec-5-ene Chemical compound CCCCCCCC=CCCCC VDFGUEPMNNLWOZ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/10—Thio derivatives
- C10M137/105—Thio derivatives not containing metal
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
- C10M135/14—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond
- C10M135/18—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond thiocarbamic type, e.g. containing the groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
- C10M135/34—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/086—Imides [having hydrocarbon substituents containing less than thirty carbon atoms]
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- C10M2215/28—Amides; Imides
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- C10M2215/30—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
- C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
- C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
- C10M2219/066—Thiocarbamic type compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/047—Thioderivatives not containing metallic elements
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9074/74A GB1500282A (en) | 1974-02-28 | 1974-02-28 | Sulphur-containing lubricating oil additives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1047506A true CA1047506A (en) | 1979-01-30 |
Family
ID=9864877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA220,916A Expired CA1047506A (en) | 1974-02-28 | 1975-02-27 | Sulphur containing lubricating oil additives |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS50124901A (enExample) |
| AT (1) | AT347556B (enExample) |
| AU (1) | AU7865575A (enExample) |
| BE (1) | BE826087A (enExample) |
| CA (1) | CA1047506A (enExample) |
| DE (1) | DE2508623A1 (enExample) |
| DK (1) | DK78075A (enExample) |
| FR (1) | FR2262661A1 (enExample) |
| IT (1) | IT1033196B (enExample) |
| NL (1) | NL7502335A (enExample) |
| NO (1) | NO750663L (enExample) |
| SE (1) | SE7502234L (enExample) |
| ZA (1) | ZA751228B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3260775A (en) * | 1962-09-18 | 1966-07-12 | Sheffield Plastics Inc | Method for making container lid fitting |
-
1975
- 1975-02-25 IT IT20660/75A patent/IT1033196B/it active
- 1975-02-27 DK DK78075*#A patent/DK78075A/da unknown
- 1975-02-27 NL NL7502335A patent/NL7502335A/xx not_active Application Discontinuation
- 1975-02-27 JP JP50024913A patent/JPS50124901A/ja active Pending
- 1975-02-27 NO NO750663A patent/NO750663L/no unknown
- 1975-02-27 FR FR7506108A patent/FR2262661A1/fr not_active Withdrawn
- 1975-02-27 BE BE153837A patent/BE826087A/xx unknown
- 1975-02-27 AT AT151975A patent/AT347556B/de not_active IP Right Cessation
- 1975-02-27 CA CA220,916A patent/CA1047506A/en not_active Expired
- 1975-02-27 ZA ZA00751228A patent/ZA751228B/xx unknown
- 1975-02-27 DE DE19752508623 patent/DE2508623A1/de active Pending
- 1975-02-27 SE SE7502234A patent/SE7502234L/xx unknown
- 1975-02-27 AU AU78655/75A patent/AU7865575A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7502335A (nl) | 1975-09-01 |
| BE826087A (fr) | 1975-06-16 |
| NO750663L (enExample) | 1975-08-29 |
| AT347556B (de) | 1979-01-10 |
| DK78075A (enExample) | 1975-10-20 |
| DE2508623A1 (de) | 1975-09-04 |
| JPS50124901A (enExample) | 1975-10-01 |
| IT1033196B (it) | 1979-07-10 |
| ZA751228B (en) | 1976-10-27 |
| ATA151975A (de) | 1978-05-15 |
| FR2262661A1 (en) | 1975-09-26 |
| AU7865575A (en) | 1976-09-02 |
| SE7502234L (enExample) | 1975-08-29 |
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