GB586841A - Improvements in and relating to the inhibition of oxidation in hydrocarbon oils - Google Patents
Improvements in and relating to the inhibition of oxidation in hydrocarbon oilsInfo
- Publication number
- GB586841A GB586841A GB15820/43A GB1582043A GB586841A GB 586841 A GB586841 A GB 586841A GB 15820/43 A GB15820/43 A GB 15820/43A GB 1582043 A GB1582043 A GB 1582043A GB 586841 A GB586841 A GB 586841A
- Authority
- GB
- United Kingdom
- Prior art keywords
- barium
- phenol
- phenate
- metal
- calcium
- 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
- 239000003921 oil Substances 0.000 title abstract 14
- 229930195733 hydrocarbon Natural products 0.000 title abstract 7
- 150000002430 hydrocarbons Chemical class 0.000 title abstract 7
- 239000004215 Carbon black (E152) Substances 0.000 title abstract 6
- 230000003647 oxidation Effects 0.000 title abstract 4
- 238000007254 oxidation reaction Methods 0.000 title abstract 4
- 230000005764 inhibitory process Effects 0.000 title 1
- 229910052788 barium Inorganic materials 0.000 abstract 25
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical group [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract 22
- 229910052751 metal Inorganic materials 0.000 abstract 19
- 239000002184 metal Substances 0.000 abstract 19
- -1 sulphhydryl groups Chemical group 0.000 abstract 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 15
- 239000005864 Sulphur Substances 0.000 abstract 15
- 150000002989 phenols Chemical class 0.000 abstract 15
- 150000001875 compounds Chemical class 0.000 abstract 12
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 10
- 229910052791 calcium Inorganic materials 0.000 abstract 10
- 239000011575 calcium Substances 0.000 abstract 10
- 238000006243 chemical reaction Methods 0.000 abstract 10
- 229910052725 zinc Inorganic materials 0.000 abstract 9
- 239000011701 zinc Chemical group 0.000 abstract 9
- 150000001298 alcohols Chemical class 0.000 abstract 8
- 125000003118 aryl group Chemical group 0.000 abstract 8
- 159000000009 barium salts Chemical class 0.000 abstract 7
- 239000000203 mixture Substances 0.000 abstract 7
- 150000003839 salts Chemical class 0.000 abstract 7
- LJKQIQSBHFNMDV-UHFFFAOYSA-N 7-thiabicyclo[4.1.0]hepta-2,4-dien-6-ol Chemical class C1=CC=CC2(O)C1S2 LJKQIQSBHFNMDV-UHFFFAOYSA-N 0.000 abstract 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- 239000003208 petroleum Substances 0.000 abstract 6
- 241000158728 Meliaceae Species 0.000 abstract 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 5
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 abstract 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- 229910052749 magnesium Chemical group 0.000 abstract 4
- 239000011777 magnesium Chemical group 0.000 abstract 4
- 229910000000 metal hydroxide Inorganic materials 0.000 abstract 4
- 229910044991 metal oxide Inorganic materials 0.000 abstract 4
- 150000004706 metal oxides Chemical class 0.000 abstract 4
- 239000010688 mineral lubricating oil Substances 0.000 abstract 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 abstract 4
- 235000019271 petrolatum Nutrition 0.000 abstract 4
- 229920000098 polyolefin Polymers 0.000 abstract 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 150000001336 alkenes Chemical class 0.000 abstract 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 229930003836 cresol Natural products 0.000 abstract 3
- 239000010687 lubricating oil Substances 0.000 abstract 3
- 229920000642 polymer Polymers 0.000 abstract 3
- 239000000344 soap Substances 0.000 abstract 3
- 229910052712 strontium Inorganic materials 0.000 abstract 3
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical group [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 abstract 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 abstract 3
- 239000001993 wax Substances 0.000 abstract 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 2
- DDMRDXBZTRHWPH-UHFFFAOYSA-N 2-(14-methylpentadecyl)phenol Chemical compound CC(C)CCCCCCCCCCCCCC1=CC=CC=C1O DDMRDXBZTRHWPH-UHFFFAOYSA-N 0.000 abstract 2
- GTRHHOMIEMLBPC-UHFFFAOYSA-N 2-dodecoxybenzoic acid Chemical class CCCCCCCCCCCCOC1=CC=CC=C1C(O)=O GTRHHOMIEMLBPC-UHFFFAOYSA-N 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 2
- 229910019142 PO4 Inorganic materials 0.000 abstract 2
- 239000004264 Petrolatum Substances 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 230000002152 alkylating effect Effects 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 239000003963 antioxidant agent Substances 0.000 abstract 2
- 235000006708 antioxidants Nutrition 0.000 abstract 2
- 235000010290 biphenyl Nutrition 0.000 abstract 2
- 239000004305 biphenyl Substances 0.000 abstract 2
- 159000000007 calcium salts Chemical class 0.000 abstract 2
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 229910017052 cobalt Inorganic materials 0.000 abstract 2
- 239000010941 cobalt Substances 0.000 abstract 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 2
- 239000003599 detergent Substances 0.000 abstract 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 239000010685 fatty oil Substances 0.000 abstract 2
- 239000007789 gas Substances 0.000 abstract 2
- 125000005843 halogen group Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 239000004615 ingredient Substances 0.000 abstract 2
- 239000003350 kerosene Substances 0.000 abstract 2
- 239000000314 lubricant Substances 0.000 abstract 2
- 159000000003 magnesium salts Chemical class 0.000 abstract 2
- 239000002480 mineral oil Substances 0.000 abstract 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052759 nickel Inorganic materials 0.000 abstract 2
- 229910052755 nonmetal Inorganic materials 0.000 abstract 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 239000012188 paraffin wax Substances 0.000 abstract 2
- 230000000737 periodic effect Effects 0.000 abstract 2
- 229940066842 petrolatum Drugs 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 abstract 2
- 239000011135 tin Substances 0.000 abstract 2
- 235000013311 vegetables Nutrition 0.000 abstract 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 abstract 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 abstract 1
- DRHABPMHZRIRAH-UHFFFAOYSA-N 2,4,4,6,6-pentamethylhept-2-ene Chemical group CC(C)=CC(C)(C)CC(C)(C)C DRHABPMHZRIRAH-UHFFFAOYSA-N 0.000 abstract 1
- URRHKOYTHDCSDA-UHFFFAOYSA-N 2,5,8,11-tetramethyldodec-2-ene Chemical group CC(C)CCC(C)CCC(C)CC=C(C)C URRHKOYTHDCSDA-UHFFFAOYSA-N 0.000 abstract 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 abstract 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 abstract 1
- WCRKLZYTQVZTMM-UHFFFAOYSA-N 2-octadecylphenol Chemical compound CCCCCCCCCCCCCCCCCCC1=CC=CC=C1O WCRKLZYTQVZTMM-UHFFFAOYSA-N 0.000 abstract 1
- 244000226021 Anacardium occidentale Species 0.000 abstract 1
- 229910015900 BF3 Inorganic materials 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 abstract 1
- XSKJGHHMELWSMA-UHFFFAOYSA-L P(=S)(SCCCCCCCC)(OCCCCCCCC)[O-].[Ba+2].C(CCCCCCC)SP(=S)(OCCCCCCCC)[O-] Chemical compound P(=S)(SCCCCCCCC)(OCCCCCCCC)[O-].[Ba+2].C(CCCCCCC)SP(=S)(OCCCCCCCC)[O-] XSKJGHHMELWSMA-UHFFFAOYSA-L 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 abstract 1
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 abstract 1
- ULGYAEQHFNJYML-UHFFFAOYSA-N [AlH3].[Ca] Chemical compound [AlH3].[Ca] ULGYAEQHFNJYML-UHFFFAOYSA-N 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 239000006079 antiknock agent Substances 0.000 abstract 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 1
- VLXUEDDQRWDTCD-UHFFFAOYSA-N calcium hexadecoxy(hexadecylsulfanyl)phosphinite Chemical compound P(SCCCCCCCCCCCCCCCC)(OCCCCCCCCCCCCCCCC)[O-].[Ca+2].C(CCCCCCCCCCCCCCC)SP(OCCCCCCCCCCCCCCCC)[O-] VLXUEDDQRWDTCD-UHFFFAOYSA-N 0.000 abstract 1
- FTOSZADXYFNRQP-UHFFFAOYSA-L calcium;2,2-dichlorooctadecanoate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCC(Cl)(Cl)C([O-])=O.CCCCCCCCCCCCCCCCC(Cl)(Cl)C([O-])=O FTOSZADXYFNRQP-UHFFFAOYSA-L 0.000 abstract 1
- ZMRQTIAUOLVKOX-UHFFFAOYSA-L calcium;diphenoxide Chemical compound [Ca+2].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 ZMRQTIAUOLVKOX-UHFFFAOYSA-L 0.000 abstract 1
- DHJGVCITGOCTCA-UHFFFAOYSA-L calcium;hexadecyl phosphate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCOP([O-])([O-])=O DHJGVCITGOCTCA-UHFFFAOYSA-L 0.000 abstract 1
- LSCGCDXAEHGNMD-UHFFFAOYSA-N calcium;phenyl octadecanoate Chemical compound [Ca].CCCCCCCCCCCCCCCCCC(=O)OC1=CC=CC=C1 LSCGCDXAEHGNMD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000006229 carbon black Substances 0.000 abstract 1
- 235000020226 cashew nut Nutrition 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 239000003245 coal Substances 0.000 abstract 1
- 238000005336 cracking Methods 0.000 abstract 1
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- 230000006866 deterioration Effects 0.000 abstract 1
- 239000002283 diesel fuel Substances 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 239000003925 fat Substances 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 229940013317 fish oils Drugs 0.000 abstract 1
- 238000011010 flushing procedure Methods 0.000 abstract 1
- 239000000446 fuel Substances 0.000 abstract 1
- 239000010439 graphite Substances 0.000 abstract 1
- 229910002804 graphite Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000011133 lead Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 229910001507 metal halide Inorganic materials 0.000 abstract 1
- 150000005309 metal halides Chemical class 0.000 abstract 1
- LVBIMKHYBUACBU-CVBJKYQLSA-L nickel(2+);(z)-octadec-9-enoate Chemical compound [Ni+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LVBIMKHYBUACBU-CVBJKYQLSA-L 0.000 abstract 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 150000002902 organometallic compounds Chemical class 0.000 abstract 1
- 235000019809 paraffin wax Nutrition 0.000 abstract 1
- QWENMOXLTHDKDL-UHFFFAOYSA-N pentoxymethanedithioic acid Chemical compound CCCCCOC(S)=S QWENMOXLTHDKDL-UHFFFAOYSA-N 0.000 abstract 1
- 235000021317 phosphate Nutrition 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 159000000001 potassium salts Chemical class 0.000 abstract 1
- 230000003449 preventive effect Effects 0.000 abstract 1
- 239000010734 process oil Substances 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000005060 rubber Substances 0.000 abstract 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 abstract 1
- 229960001860 salicylate Drugs 0.000 abstract 1
- 239000003079 shale oil Substances 0.000 abstract 1
- 239000010802 sludge Substances 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000002562 thickening agent Substances 0.000 abstract 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 abstract 1
- 239000012991 xanthate Substances 0.000 abstract 1
- HMWOZFDPTNURLH-UHFFFAOYSA-L zinc cyclohexyloxy-methylsulfanyl-oxido-sulfanylidene-lambda5-phosphane Chemical compound P(=S)(SC)(OC1CCCCC1)[O-].[Zn+2].CSP(=S)(OC1CCCCC1)[O-] HMWOZFDPTNURLH-UHFFFAOYSA-L 0.000 abstract 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 abstract 1
- 239000011787 zinc oxide Substances 0.000 abstract 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/20—Thiols; Sulfides; Polysulfides
- C10M135/28—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring
- C10M135/30—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring containing hydroxy groups; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- 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
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/04—Elements
- C10M2201/041—Carbon; Graphite; Carbon black
-
- 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
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/04—Elements
- C10M2201/041—Carbon; Graphite; Carbon black
- C10M2201/042—Carbon; Graphite; Carbon black halogenated, i.e. graphite fluoride
-
- 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
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- Lubricants (AREA)
Abstract
Oxidation and deterioration of hydrocarbon oils is inhibited by incorporating therein a small quantity of a reaction product of sulphur with a compound containing the structural group ArXMT where Ar is an aromatic nucleus, X is a non-metal of Group 6 of the Periodic Table, M is calcium, barium, strontium, zinc or magnesium, and T is OH or (OM)nXAr where n is O, 1 or 2. The aromatic nucleus may be benzene, biphenyl, naphthalene or anthracene, and may contain substituents such as alkyl, aryl, carboxyl, hydroxyl, alkoxy or sulphhydryl groups, metal-substituted carboxyl, hydroxyl or sulphhydryl groups, or halogen atoms. Preferably the compound to be reacted with sulphur contains the structural group RArXMT where R represents at least one alkyl radicle joined to the aromatic nucleus Ar, the sum total of carbon atoms in such radicles being at least 5 and T in this case being OH or (OM)nXArR. Specific compounds suitable for reaction with sulphur are barium tert.-octyl phenate, barium di-(tert.-octyl) phenate, calcium tert.-octyl phenate, barium di-(tert.-amyl) phenate, barium cetyl phenate, zinc isohexadecyl phenate, calcium salt of petroleum phenols, barium salt of wax-alkylated phenol, magnesium salt of octadecyl cresol, barium salt of phenol alkylated with refinery olefin polymers, metal phenate salts of alkylated aromatic hydroxy carboxylic acids and their carboxylate salts such as the barium phenate-zinc carboxylate of lauryl salicylic acid and metal salts of phenol sulphides or alkylated phenol sulphides, where the sulphur acts as a link between two or more of the structural groups, as in the case of the barium salt of tert.-octyl phenol sulphide. Where the compound to be reacted with sulphur is formed by reacting an alkylated phenol with a metal oxide or hydroxide, both reactions may be carried out simultaneously by reacting the alkylated phenol with a metal oxide or hydroxide and sulphur. The sulphurizing reaction may be carried out in presence of an aliphatic alcohol having from 8 to 20 carbon atoms per molecule, such as lauryl, cetyl, stearyl or woolfat alcohol, or of an unsaturated alcohol or of olefinic material such as tetraisobutylene or lower aliphatic olefins. The hydrocarbon oils may be mineral lubricating oils including hydrogenated or white oils, synthetic oils prepared for example by the polymerization of olefins or by the reaction of oxides of carbon with hydrogen or by the hydrogenation of coal or its products, cracking coil tar fractions or shale oil distillates. Hydrocarbon oil compositions mentioned are crankcase lubricants, extreme pressure lubricants, engine flushing oils, process oils, industrial oils, general machinery oils, greases, rust preventive compositions, motor fuels particularly those containing tetraethyl lead or other anti-knock agents, Diesel fuels and kerosene. The hydrocarbon oil compositions may contain additional ingredients such as dyes, pour depressors, heat-thickened fatty oils, sulphurized fatty oils, organo-metallic compounds, metallic or other soaps, sludge dispersers, anti-oxidants, thickeners, viscosity index improvers, oiliness agents, resins, rubber, olefin polymers, voltolized fats, voltolized mineral oils, voltolized waxes, colloidal solids such as graphite or zinc oxide, and solvents and assisting agents such as esters, ketones, alcohols, aldehydes, or halogenated or nitrated compounds. Specific alcohols mentioned are octyl, lauryl, cetyl, heytadecyl, stearyl, oleyl, phenyloctyl, or octadecylbenzyl alcohols, naphthenic alcohols, alcohols from woolfat or sperm oil and alcohols prepared by the oxidation of petroleum hydrocarbons such as paraffin wax or petrolatum. Woolfat or sperm oils may be used instead of the alcohols obtained from them. In the case of lubricating oil compositions, additional ingredients of the detergent type such as metal soaps, metal phenates, metal alcoholates, metal phenol sulphides, metal organo-phosphates, -thiophosphates, -phosphites, or -thiophosphites, metal sulphonates, metal thiocarbamates, metal xanthates or metal thioxanthates may be present. Specific detergents mentioned are barium tert.-octyl phenol sulphide, cobalt tert. -amyl phenol sulphide, calcium mahogany sulphonate, tin salt of wax alkylated phenol sulphide, strontium mahogany sulphonate, magnesium cetyl phenate, nickel oleate, aluminium -calcium mixed soap of fatty acid from oxidation of petroleum fractions, calcium isohexadecyl phenol sulphonate, barium octadecylate, calcium dichlorostearate, nickel amyl xanthate, calcium phenyl stearate, nickel dibutyl dithiocarbamate, barium dioctyl dithiophosphate, zinc methyl cyclohexyl dithiophosphate, calcium dihexadecyl monothiophosphite, calcium cetyl phosphate, barium mahogany sulphonates, zinc diisopropyl salicylate, aluminium naphthenate, magnesium mahogany sulphonates, di-calcium salt of octadecyl phenol sulphonic acid in which calcium replaces both the phenolic and the acid hydrogen, barium phenate-zinc sulphonate of isohexadecyl phenol sulphonic acid, barium di-tert. -amyl phenol sulphide, calcium phenate -barium carboxylate of octadecyl salicyclic acid and tin naphthenate. Mineral lubricating oil compositions are described which contain, in addition to the sulphurized compound, calcium, barium or zinc mahogany sulphonate. In the examples, (a) sulphurized calcium or barium p-tert.-octyl phenate and stearyl alcohol with or without carbon black, (b) sulphurized barium 2, 4 ditert.-amyl phenate and stearyl alcohol and (c) sulphurized barium phenate of alkyl phenol obtained by alkylating ordinary phenol with butene polymers, are incorporated in mineral lubricating oil. For comparison purposes mineral lubricating oil compositions containing (i) the unsulphurized barium phenate of (c) or (ii) barium tert.-octyl phenol sulphide and barium tert.-octyl phenol disulphide are described. The Specification as open to inspection under Sect. 91 refers to the reaction products of sulphur with compounds in which M of the structural group is tin, lead, cobalt or nickel. It is stated that the reaction with sulphur may be applied to other organic compounds containing the -OM group such as the metal alcoholates, e.g., calcium octadecylate or the barium salts of wax alcohols, or metal ketonates to form compositions useful as lubricating oil additives. The addition of the sulphurized compounds to lubricating oils comprising animal, vegetable or fish oils or their hydrogenated or voltolized products, either alone or in admixture with mineral oils, is described. This subject-matter does not appear in the Specification as accepted.ALSO:Anti-oxidants for adding to hydrocarbon oils are prepared by reacting sulphur with a compound containing the structural group ArXMT where Ar is an aromatic nucleus, X is a nonmetal of Group 6 of the Periodic Table, M is calcium, barium, strontium, magnesium or zinc, and T is OH or (OM)nXAr where n is 0.1 or 2. The aromatic nucleus may be benzene, biphenyl, naphthalene or anthracene and may contain substituents such as alkyl, aryl, carboxyl, hydroxyl, alkoxy or sulphhydryl groups, metal-substituted carboxyl, hydroxyl or sulphhydryl groups, or halogen atoms. Preferably the compound to be reacted with sulphur contains the structural group RAr XMT where R represents at least one alkyl radicle joined to the aromatic nucleus Ar, the sum total of carbon atoms in such radicles being at least 5 and T in this case being OH or (OM)nXArR. Specific compounds suitable for reaction with sulphur are barium tert.-octyl phenate, barium di-(tert-octyl)-phenate, calcium tert.-octyl phenate, barium di-(tert.-amyl)-phenate, barium cetyl phenate, zinc isohexadecyl phenate, calcium salt of petroleum phenols, barium salt of wax-alkylated phenol, magnesium salt of octadecyl cresol, barium salt of phenol alkylated with refinery olefin polymers, metal phenates of alkylated aromatic hydroxy carboxylic acids and their carboxylate salts such as the barium phenate-zinc carboxylate of lauryl salicylic acid and metal salts of phenol sulphides or alkylated phenol sulphides, where the sulphur acts as a link between two or more of the structural groups, as in the case of the barium salt of tert.-octyl phenol sulphide. Suitable alkylated phenols, whose metal salts may be reacted with sulphur, may be prepared by alkylating phenol, cresol, naphthol or other phenolic compounds with such alkylating agents as alcohols, alkyl halides, alkyl phosphates or olefins, with the aid of catalysts such as aluminium chloride, boron fluoride and other metal halides, hydrochloric acid, hydrofluoric acid, sulphuric acid, phosphoric acid or activated clay. Suitable olefins are petroleum refinery gases, butene, amylene and olefin polymers such as di-isobutylene, triisobutylene or other isobutylene polymers or normal butene polymer. Other suitable alkylated phenols are those prepared by condensing phenols with chlorinated paraffin wax, chlorinated petrolatum, or with a chlorinated kerosene or gas oil. Halogenated or nitrated phenols or naturally occuring phenols such as those obtained by alkaline extraction of certain petroleum stocks or those obtained from cashew nut shell liquid or from other vegetable sources, may also be employed. The phenols may be converted to their metal salts by direct reaction with the oxide, hydroxide or alcoholate of the desired metal or the sodium or potassium salts may first be formed by reaction with sodium or potassium hydroxide and those salts converted to the desired divalent metal salts by double decomposition. Where the compound to be reacted with sulphur is formed by reacting an alkylated phenol with a metal oxide or hydroxide, both reactions may be carried out simultaneously by reacting the alkylated phenol with a metal oxide or hydroxide and sulphur. The sulphurizing reaction may be carried out in presence of an aliphatic alcohol having from 8 to
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US586841XA | 1943-05-10 | 1943-05-10 |
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GB586841A true GB586841A (en) | 1947-04-02 |
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GB15820/43A Expired GB586841A (en) | 1943-05-10 | 1943-09-27 | Improvements in and relating to the inhibition of oxidation in hydrocarbon oils |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115975693A (en) * | 2021-10-14 | 2023-04-18 | 中国石油化工股份有限公司 | Industrial lubricating oil composition and preparation method thereof |
CN115975702A (en) * | 2021-10-14 | 2023-04-18 | 中国石油化工股份有限公司 | Gasoline engine oil composition and preparation method thereof |
-
1943
- 1943-09-27 GB GB15820/43A patent/GB586841A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115975693A (en) * | 2021-10-14 | 2023-04-18 | 中国石油化工股份有限公司 | Industrial lubricating oil composition and preparation method thereof |
CN115975702A (en) * | 2021-10-14 | 2023-04-18 | 中国石油化工股份有限公司 | Gasoline engine oil composition and preparation method thereof |
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