US2766207A - Hydrocarbon oil products - Google Patents
Hydrocarbon oil products Download PDFInfo
- Publication number
- US2766207A US2766207A US329112A US32911252A US2766207A US 2766207 A US2766207 A US 2766207A US 329112 A US329112 A US 329112A US 32911252 A US32911252 A US 32911252A US 2766207 A US2766207 A US 2766207A
- Authority
- US
- United States
- Prior art keywords
- product
- oils
- oil
- products
- phenol
- 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 - Lifetime
Links
- 229930195733 hydrocarbon Natural products 0.000 title description 8
- 150000002430 hydrocarbons Chemical class 0.000 title description 8
- 239000004215 Carbon black (E152) Substances 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims description 18
- 239000010687 lubricating oil Substances 0.000 claims description 13
- 239000010688 mineral lubricating oil Substances 0.000 claims description 11
- 230000003647 oxidation Effects 0.000 claims description 9
- 238000007254 oxidation reaction Methods 0.000 claims description 9
- LJKQIQSBHFNMDV-UHFFFAOYSA-N 7-thiabicyclo[4.1.0]hepta-2,4-dien-6-ol Chemical compound C1=CC=CC2(O)C1S2 LJKQIQSBHFNMDV-UHFFFAOYSA-N 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 239000000047 product Substances 0.000 description 61
- 239000003921 oil Substances 0.000 description 33
- 229910052717 sulfur Inorganic materials 0.000 description 21
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 239000000654 additive Substances 0.000 description 15
- -1 alkyl phenol sulfide dithiophosphoric acids Chemical class 0.000 description 15
- 150000002989 phenols Chemical class 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 13
- 229910052698 phosphorus Inorganic materials 0.000 description 13
- 239000011593 sulfur Substances 0.000 description 13
- 150000001298 alcohols Chemical class 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 238000005260 corrosion Methods 0.000 description 9
- 230000007797 corrosion Effects 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000002199 base oil Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 239000011574 phosphorus Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000002485 combustion reaction Methods 0.000 description 5
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 5
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 5
- 239000000314 lubricant Substances 0.000 description 5
- 239000003209 petroleum derivative Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 4
- 238000007664 blowing Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- MTZWHHIREPJPTG-UHFFFAOYSA-N phorone Chemical compound CC(C)=CC(=O)C=C(C)C MTZWHHIREPJPTG-UHFFFAOYSA-N 0.000 description 4
- 229930193351 phorone Natural products 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- WIKSRXFQIZQFEH-UHFFFAOYSA-N [Cu].[Pb] Chemical compound [Cu].[Pb] WIKSRXFQIZQFEH-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 3
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 3
- 150000008117 polysulfides Polymers 0.000 description 3
- 150000003139 primary aliphatic amines Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000010802 sludge Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 239000010685 fatty oil Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- 239000010705 motor oil Substances 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- 239000005077 polysulfide Substances 0.000 description 2
- 229920001021 polysulfide Polymers 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- FUPAJKKAHDLPAZ-UHFFFAOYSA-N 1,2,3-triphenylguanidine Chemical compound C=1C=CC=CC=1NC(=NC=1C=CC=CC=1)NC1=CC=CC=C1 FUPAJKKAHDLPAZ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- XFHFHASAGYJPOW-UHFFFAOYSA-N 1-octyl-7-thiabicyclo[4.1.0]hepta-2,4-dien-6-ol Chemical compound C1=CC=CC2(CCCCCCCC)C1(O)S2 XFHFHASAGYJPOW-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- LLIGXYDULHXBDJ-UHFFFAOYSA-N 2-(4-methylpentyl)phenol Chemical compound CC(C)CCCC1=CC=CC=C1O LLIGXYDULHXBDJ-UHFFFAOYSA-N 0.000 description 1
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 1
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 1
- 101710098247 Exoglucanase 1 Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229910000978 Pb alloy Inorganic materials 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical class S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000746181 Therates Species 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- AGXUVMPSUKZYDT-UHFFFAOYSA-L barium(2+);octadecanoate Chemical compound [Ba+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AGXUVMPSUKZYDT-UHFFFAOYSA-L 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- NSAODVHAXBZWGW-UHFFFAOYSA-N cadmium silver Chemical compound [Ag].[Cd] NSAODVHAXBZWGW-UHFFFAOYSA-N 0.000 description 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 description 1
- DHJGVCITGOCTCA-UHFFFAOYSA-L calcium;hexadecyl phosphate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCOP([O-])([O-])=O DHJGVCITGOCTCA-UHFFFAOYSA-L 0.000 description 1
- LSCGCDXAEHGNMD-UHFFFAOYSA-N calcium;phenyl octadecanoate Chemical compound [Ca].CCCCCCCCCCCCCCCCCC(=O)OC1=CC=CC=C1 LSCGCDXAEHGNMD-UHFFFAOYSA-N 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- KDFFXYVOTKKBDI-UHFFFAOYSA-N n-ethylnaphthalen-1-amine Chemical compound C1=CC=C2C(NCC)=CC=CC2=C1 KDFFXYVOTKKBDI-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 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 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000010734 process oil Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 230000013707 sensory perception of sound Effects 0.000 description 1
- 239000003079 shale oil Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical group ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 150000003582 thiophosphoric acids Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- BDRXBLJBLMWRHN-UHFFFAOYSA-L zinc cyclohexyloxy-methoxy-oxido-sulfanylidene-lambda5-phosphane Chemical compound P(=S)(OC)(OC1CCCCC1)[O-].[Zn+2].COP(=S)(OC1CCCCC1)[O-] BDRXBLJBLMWRHN-UHFFFAOYSA-L 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
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- C10M137/04—Phosphate esters
- C10M137/10—Thio derivatives
- C10M137/105—Thio derivatives not containing metal
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
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- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
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- C10L1/10—Liquid carbonaceous fuels containing additives
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- C10L1/2658—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond) amine salts
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- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
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- 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
- C10M2223/045—Metal containing thio derivatives
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- 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
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- 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
- C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
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- 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
- C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
- C10M2223/121—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy of alcohols or phenols
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- 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
- C10N2010/00—Metal present as such or in compounds
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- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
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- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/06—Groups 3 or 13
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- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
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- 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
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
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- 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
- C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
- C10N2060/04—Oxidation, e.g. ozonisation
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- 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
Definitions
- the present invention relates to the improvement of hydrocarbon products derived from petroleum sources and more particularly to the preparation of improved mineral lubricating oil compositions by the incorporation therein of a class of. additives which impart improved properties to such hydrocarbon compositions.
- a new class of compounds has been discovered which when added to refined lubricating oils and other petroleum hydrocarbon products in small proportions substantially reduces the tendency of such oils to corrode the metal surfaces, particularly the surfaces of copper-lead and cadmium-silver bearings which are employed in internal combustion engines, and they are likewise effective in inhibiting oxidation of petroleum hydrocarbon products generally.
- the products of the present invention are also usefulas detergent additives for internal combustion engine lubricants. Since the products contain no metal, they are particularly useful as ashless detergents in service where ash-forming constituents lead'to harmful'etfects inengines operating under severe conditions, such as in the case of aviation engines.
- the compounds of the present invention may be described as nitrogen base salts of alkyl phenol sulfide dithiophosphoric acids having the following general formula:
- R represents at least one alkylradical, preferably having in the range of about 4 to 20 carbon atoms
- T represents a nitrogen base radical
- x repice form a phenol sulfide, then reacting the phenol sulfide with a sulfide of phosphorus such as phosphorus pentasulfide, and finally converting the resulting dithiophosphoric acid derivative to a salt by neutralizing the same with a nitrogen base such as ammonia or an amine.
- the additives of the present invention may be prepared in a light solvent and isolated, or, if they are to be employed as lubricating oil additives, they may be made directly in a lubrication oil medium to form a concentrate containing in the range of 20 to 60% of active ingredient.
- the alkylated phenols are conveniently prepared by reacting simple phenols with olefinic hydrocarbons such as propylene, butylene, isobutylene, amylenes, diisobutylene, triisobu'tylene, etc., or olefin-containing mixtures obtained in petroleum refining processes as refinery gases.- The reaction of these materials is promoted by means of a catalyst, such as sulfuric acid.
- a catalyst such as sulfuric acid.
- the sulfurized phenols employed in accordance with the present invention are prepared by reacting the pheml with a sulfur halide.
- a sulfur halide For example, sulfur monochloride (S2Cl2), is conveniently reacted in proportion of about /2 mol per mol of phenol and preferably in a solvent such as dichlorethane to produce an alkyl phenol disulfide.
- SClz sulfur dichloride
- thealkyl phenols are given thi'oether linkage substituents.
- the sulfide of phosphorus employed in the preparation of substituted thiophosphoric acid is preferably phosphorus pentasulfide (P2S5).
- the nitrogen bases which may be employed in the preparation of the salts of the present invention include ammonia and the organic bases. Among the latter, the most useful are the primary and secondary aliphatic amines, but other organic basic materials may be used, such as text-aliphatic amines, aromatic amines, monocyclohexyland dicycloh'exyl amines.- Specific examples of such amines include methylamine, ethylamine, isopropylamine, diisopropylamine, diethylamine, aniline, ethylaniline, benzylamine, ethylnaphthylamine, p-phenylenediamine and theheterocyclic amines, such as pyridine and piperidine.
- the quaternary ammonium hydroxides may also be employed.
- Compounds having a guanidine structure such as guanidine, triphenyl guanidine, and the like, may likewise be employed.
- the quantity of the additives of the present invention which is most advantageously blended in mineral lubricating oils or other petroleum hydrocarbon products is generally from about 0.1% to 2% by weight when the addi- EXAMPLE I.PREPARATION OF n-BUTYLAMINE TERT.-OCTYLPHENOL SULFIDE DITHIOPHOS- PHATE Product
- A.Sulfurized tert.-ctylphenol A 4-necked 3 liter flask equipped with a stirrer, thermometer, reflux condenser and dropping funnel was charged with 1.5 liters of ethylene dichloride and 412 g. (2 mol) of tert.-octylphenol (prepared by reacting phenol with diisobutylene in the presence of a catalyst).
- Product B -Sulfurized terL-octylpheliol dithiophosphoric acid 379 g. (0.8 mol) of sulfurized terL-octylphenol (Product A) was placed in a 3-necked 2 liter flask equipped with a stirrer, thermometer, and reflux condenser. The viscous material was fluidized by heating to about 70 C., after which 88.8 g. (0.4 mol) of P285 was added. The mixture was heated at 160 C. for 2 hours with rapid stirring, after which it was dissolved in 1 liter of ethylene dichloride and filtered to remove a small amount of unreacted P285. A 15 ml. portion of the solution was poured into an evaporating dish and placed on the steam bath to remove the solvent. A dark sticky solid was obtained which analyzed 4.7% P (phosphorus) and 17.7% S.
- Product C consists chiefly of compounds having-the approximate average formula:
- the structure ofProduct C arises from the fact that the reaction of a phenol and sulfur halide'is known to form a phenol sulfide containing one-or more sulfur atoms interconnecting benzene nuclei. Subsequent reaction with phosphorus pentasulfide forms the dithiophosphate having an available'sulfhydryl group which in turn reacts with the amine. Evidence of reaction'of the amine and thiophosphate is further shown inthat a temperature rise of 16 C. occurred when the amine was added. Drastic hydrolysis of product C resultedin substantially no reduction of the sulfur content of the'compound. This is characteristic of the sulfur bridge between aromatic nuclei, such bridges not beingrsusceptible to hydrolysis even under severe conditions.
- Product G on the other handyappears to be chiefly a polysulfi-de derivative of diaryldithiophosphoric: acid .in which the hydrogen of the sulfhydryl groups of two molecules :of-the. dithiophosphoric acid, formed by reacting phenol and-P285, is removedyand the two resultingradicals are joined by'oneor more atoms -.of sulfur when reacted with sulfur'halide. Nowacid groupsare available for further reaction. Thisagrees with experimental data. There was no evidence of reaction between the polysultide and the amine since substantiallyno temperature increase occurred when the'two materials were :mixed together. The amine appeared to be present.
- EXAMPLE 4 -COMPARISON OF LUBRICANT AD- DITIVE' PROPERTIES OF PRODUCTSC AND G Phorone detergency test Blends containing 1% by weight each of products C and G in a paraflinic-type mineral lubricating oil of SAE-3O grade and a sample of the unblended base oil were submitted to adetergencyrtest designed to measure the effectiveness of theadditives for preventing harmful engine deposits in internal combustion engines. The test is conducted as follows: 100 g. of testoil 'are weighed into a clean, 300 cc. tall-form, open glass beaker provided with a stirrer. The beaker is placed in an oil bath maintained at a-temperature of 275 'F.
- the test was conducted as follows: 500 cc. of the oil was placed in a glass oxidation tube (13 inches long and 2% inches in diameter) fitted at the bottom with a /1 inch air inlet tube perforated to facilitate air distribution.
- the oxidation tube was then immersed in a heating bath so that the oil temperature was maintained at 325 F during the test.
- Two quarter sections of automotive bearings of copper-lead alloy of known weight having a total area of 25 sq. cm. were attached to opposite sides of a stainless steel rod which was then immersed in the test'oil and rotated at 600 R. P. M., thus providing sufiicient agitation of the sample during the test.
- Air was then blown through the oil at therate of 2 cu. ft. per hour. At the end of each 4-hour period the hearings were removed, washed with naphtha and weighed to determine the amount of loss by corrosion.
- the bearings were then repolished (to increase-the'severity of the test) ,reweighed, and then subjected to the test for additional 4-hour periods in likemanner.
- the results are given in Table II as corrosion life, which indicates the number of hours 'required for the bearings to lose 100 mg. in weight, determined by interpolation of the data obtained in the various periods.
- EXAMPLE 5 PREPARATION OF ISOPROPYL- AMINE SALT OF TERT.-OCTYL PHENOL SUL- FIDE TI-HOPHOSPHATE sulfide so prepared (containing 1.5 gram atoms of sulfur per mol), and 716 g. of a refined light lubricating oil of approximately SAE10 grade was heated in a 4 liter beaker until a homogeneous solution was obtained (90 C.). 111 g. of P285 was added and the reaction temperature was increased to 140 C. and maintained at this point for 4 hours, followed by filtration to remove a small amount of insoluble material. The filtrate was placed in a 4 liter beaker, and a solution of 118 g.
- a lubricant blend containing the product of this example was submitted to a bearing corrosion test conducted by the conditions described in Example IV.
- the base stock employed was an SAE grade paraflinic-type mineral lubricating oil having a bearing corrosion life of 10 hours.
- This base oil containing 0.25% by weight of the isopropyl amine salt of tert.-octyl phenol sulfide thiophosphate had a bearing corrosion life of 33 hours.
- the products of the present invention may be employed not only in ordinary hydrocarbon lubricating oils but also in the heavy duty type of lubricating oils which have been compounded with such detergent type additives as metal soaps, metal petroleum sulfonates, metal phenates, metal alco'holates, metal alkyl phenol sulfides, metal organo phosphates, thiophosphates, phosphites and thiophosphites, metal salicylates, metal xanthates and thioxanthates, metal thiocarbamates, amines and amine derivatives, reaction products of metal phenates and sulfur, re action products of metal phenates and phosphorus sulfides, metal phenol sulfonates, and the like.
- detergent type additives as metal soaps, metal petroleum sulfonates, metal phenates, metal alco'holates, metal alkyl phenol sulfides, metal organo phosphates, thiophosphates,
- the additives of the present invention may be used in lubrieating oils containing such other addition agents as bariurn tert.-octylphenol sulfide, calcium tert.-amylphenol sulfide, nickel oleate, barium stearate, calcium phenyl stearate, zinc diisopropyl salicylate, aluminum naphthenate, calcium cetyl phosphate, barium di-tert.-amylphenol sulfide, calcium petroleum sulfonate, zinc methyl cyclohexyl thiophosphate, calcium dichlorostearate, etc.
- Other types of additives such as phenols and phenol sulfides may be employed.
- the lubricating oil base stocks used in the compositions of this invention may be straight mineral lubricating oils or distillates derived from paraflinic, naphthenic, asphaltic or mixed base crudes, or, if desired, various blended oils may be employed as well as residuals, particularly those from which asphaltic constituents have been carefully removed.
- the oils may be refined by conventional methods using acid, alkali and/or clay or other agents such as aluminum chloride, or they may be extracted oils produced, for example, by solvent extraction with solvents of the type of phenol, sulfur dioxide, furfural, dichlorod-iethyl ether, nitrobenzene, crotonaldehyde, etc.
- Hydrogenated oils or white oils may be employed as well as 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 and coal tar or shale oil distillates may also be used.
- animal, vegetable or fish oils or their hydrogenated or voltolized products may be employed in admixture with mineral oils.
- the base stock chosen should normally be that oil which without the new additive present gives the optimum performance in the service contemplated.
- one advantage of the additives is that their use also makes feasible the employment of less satisfactory mineral oils or other oils, no strict rule can be laid down for the choice of the base stock.
- Certain essentials must of course be observed.
- the oils must possess the viscosity and volatility characteristics known to be required for the service contemplated.
- the oil must be a satisfactory solvent for the additive, although in some cases auxiliary solvent agents may be used; 7
- the lubricating oils, however they may have been produced, may vary considerably in viscosity and other properties depending upon the particular use for which they are desired, but they usually range from about 40 to 150 sec- 0nd Saybolt viscosity at 210 F.
- oils of higher viscosity index are often preferred, for example, up to 75 to 100, or even higher, viscosity index.
- agents may also be used such as dyes, pour depressors, heat thickened fatty oils,.sulfurized fatty oils, organo-metallic compounds, metallic or other soaps, sludge dispersers, antioxidants, thickeners, viscosity index improvers, oiliness agents, resins, rubber, olefin polymers, voltolized fats, voltolized oils, and/or voltolized waxes and colloidal solids such as graphite or zinc oxide, etc.
- Solvents and assisting agents such as esters, ketones, alcohols, aldehydes, halogenated or nitrated compounds, and the like may also be employed.
- Assisting agents which are particularly desirable as plasticizers and def oamers are the higher alcohols having eight or more carbon atoms and preferably 12 to 20 carbon atoms.
- the alcohols may be saturated straight and branched chain aliphatic alcohols such as octyl alcohol (CBHI'IOH), lauryl alcohol (C12H25OH), cetyl alcohol (CrsHzaOH), stearyl alcohol, sometimes referred to as octadecyl alcohol (C18H3'IOH), heptadecyl alcohol (C17H35OH), and the like, the corresponding olefinic alcohols such as oleyl alcohol; cyclic alcohols such as naphthenic alcohols; and aryl substituted alkyl alcohols,'for
- phenyl octyl alcohol, or octadecyl benzyl alcohol or mixtures of these various alcohols which may be pure or substantially pure synthetic alcohols.
- One may also use mixed naturally occurring alcohols such as those found in wool fat (which is known to contain a substantial percentage of alcohols having about 16 to 18 carbon atoms) and in sperm oil (which contains a high percentage of cetyl alcohol); and although it is preferable to isolate the alcohols from those materials, for some purposes, the wool fat, sperm oil or other natural products rich in alcohols may be used per se.
- Products prepared synthetically by chemical processes may also be used, such as .alcohols prepared by the oxidation of petroleum hydrocarbons, e. g. paraflin wax, petrolatum, etc.
- the additives of the present invention may also be used in extreme pressure lubricants, engine flushing oils, industrial oils, general machinery oils, process oils, rust preventive compositions and greases.
- the additives of the present invention may be employed as antioxidant or stabilizing agents not only in mineral lubricating oils, but also in petroleum hydrocarbon products generally, where improved resistance to oxidation is desired.
- the products may be added to motor oils, diesel fuels, kerosene, waxes, hydrocarbon polymers, etc. and other mineral oils.
- a lubricating oil composition comprising a major proportion of a mineral lubricating oil and a minor, oxi dation inhibiting amount of a product obtained by react- 10 ing about 2 moles of an alkyl phenol sulfide having the formula:
- R is an alkyl group having in the range of about 4 to 20 carbon atoms and x represents an integer of about 1 to 3, with about 1 mole of P285 at a temperature of about to C. for about 2 to 4 hours, and thereafter reacting the resulting alkyl phenol sulfide-P285 reaction product with about 2 moles of a primary aliphatic amine, selected from the group consisting of n-butylamine and isopropylamine.
- a lubricating oil composition comprising a major proportion of a mineral lubricating oil and about 0.1 to 2.0% by weight, based on the total composition, of a prodnot obtained by reacting about 2 moles of tert. octyl phenol sulfide with about 1 mole of P285 at a temperature of about 140 to 160 C. for about 2 to 4 hours, and thereafter reacting the resultant tert. octyl phenol sulfide-P285 reaction with about 2 moles of a primary aliphatic amine selected from the group consisting of n-butylarnine and isopropylamine.
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Description
United States atent O HYDROCARBON OIL PRODUCTS John Patrick McDermott, Springfield, N. 1., assignor to Esso Research and Engineering Company, a corporation of Delaware No Drawing. Application December 31, 1952, Serial No. 329,112
2 Claims. (Cl. 252-325) The present invention relates to the improvement of hydrocarbon products derived from petroleum sources and more particularly to the preparation of improved mineral lubricating oil compositions by the incorporation therein of a class of. additives which impart improved properties to such hydrocarbon compositions.
This application is a continuation-in-part of U. S. patent application Serial No. 776,870, filed September 29, 1947,, now abandoned.
In the development of petroleum lubricating oils the trend has been to use more and more eflicient refining methods in order to reduce the tendency of the oils to formv carbon and deposits of solid matter or sludge. While such highly refined oils possess many advantages, their resistance to oxidation particularly under conditions. of. severe service is generally decreased and they are more prone; to form soluble acidic oxidation products which are corrosive. They are generally less effective than the untreated oils in protecting the metal surfaces which they contact against rusting and corrosion due to oxygen and moisture. They also often deposit thickfilms of varnish on hot metal surfaces, such as the pistons of internal combustion engines.
In accordance with the present invention a new class of compoundshas been discovered which when added to refined lubricating oils and other petroleum hydrocarbon products in small proportions substantially reduces the tendency of such oils to corrode the metal surfaces, particularly the surfaces of copper-lead and cadmium-silver bearings which are employed in internal combustion engines, and they are likewise effective in inhibiting oxidation of petroleum hydrocarbon products generally. The products of the present invention are also usefulas detergent additives for internal combustion engine lubricants. Since the products contain no metal, they are particularly useful as ashless detergents in service where ash-forming constituents lead'to harmful'etfects inengines operating under severe conditions, such as in the case of aviation engines.
The compounds of the present invention may be described as nitrogen base salts of alkyl phenol sulfide dithiophosphoric acids having the following general formula:
In this formula R represents at least one alkylradical, preferably having in the range of about 4 to 20 carbon atoms, T represents a nitrogen base radical, and x repice form a phenol sulfide, then reacting the phenol sulfide with a sulfide of phosphorus such as phosphorus pentasulfide, and finally converting the resulting dithiophosphoric acid derivative to a salt by neutralizing the same with a nitrogen base such as ammonia or an amine. The additives of the present invention may be prepared in a light solvent and isolated, or, if they are to be employed as lubricating oil additives, they may be made directly in a lubrication oil medium to form a concentrate containing in the range of 20 to 60% of active ingredient.
Examples of phenols which may be sulfurized and then converted into acids of phosphorus and then new tralized include the simple phenols which are preferably alkylated to provide sufficient oilsolubility in the final product. The alkylated phenols are conveniently prepared by reacting simple phenols with olefinic hydrocarbons such as propylene, butylene, isobutylene, amylenes, diisobutylene, triisobu'tylene, etc., or olefin-containing mixtures obtained in petroleum refining processes as refinery gases.- The reaction of these materials is promoted by means ofa catalyst, such as sulfuric acid. By these means bothmonoalkyland polyalkyl phenols may be prepared and employed in accordance with the present invention. Another class of phenols which may be likewise employed for the purpose of this invention consists of what is known as petroleum phenols, which are obtained by extraction of various petroleum hydrocarbon stocks, chiefly from cracking and heating processes, with caustic soda and acidification of the alkaline extract witha mineral acid, followed by distillation if desired. These petroleum phenols are considered to contain alkyl or cycloalkyl sidechains. Specific phenols which are particularly useful in preparing the salts of the present invention are tert.-amyl phenol, isohexyl phenol, tert.-octyl phenol, di-tert.-amyl phenol, and the like. Phenols containing wax chains or side chains containing cycloaliphaticring structures may also be employed.
The sulfurized phenols employed in accordance With the present invention are prepared by reacting the pheml with a sulfur halide. For example, sulfur monochloride (S2Cl2), is conveniently reacted in proportion of about /2 mol per mol of phenol and preferably in a solvent such as dichlorethane to produce an alkyl phenol disulfide. Using substantially the same procedure but substituting sulfur dichloride (SClz) for the monochloride, thealkyl phenols are given thi'oether linkage substituents. The sulfide of phosphorus employed in the preparation of substituted thiophosphoric acid is preferably phosphorus pentasulfide (P2S5)..
The nitrogen bases which may be employed in the preparation of the salts of the present invention include ammonia and the organic bases. Among the latter, the most useful are the primary and secondary aliphatic amines, but other organic basic materials may be used, such as text-aliphatic amines, aromatic amines, monocyclohexyland dicycloh'exyl amines.- Specific examples of such amines include methylamine, ethylamine, isopropylamine, diisopropylamine, diethylamine, aniline, ethylaniline, benzylamine, ethylnaphthylamine, p-phenylenediamine and theheterocyclic amines, such as pyridine and piperidine. The quaternary ammonium hydroxides may also be employed. Compounds having a guanidine structure, such as guanidine, triphenyl guanidine, and the like, may likewise be employed.
In choosing the reactants for the preparation of a salt in accordance'with the present invention, which is to be employed as an additive'for a mineral oil, consideration should be given'to the oil solubility of the final product. It phenols containing short side chains are employed, it is advisable to employ for the neutralizing reaction an amine containing a'long aliphatic group for the purpose of providing oil solubility. If the solubility is provided in long chains in the phenols, a satisfactory product may be prepared by using ammonia or amines containing only short chains.
The quantity of the additives of the present invention which is most advantageously blended in mineral lubricating oils or other petroleum hydrocarbon products is generally from about 0.1% to 2% by weight when the addi- EXAMPLE I.PREPARATION OF n-BUTYLAMINE TERT.-OCTYLPHENOL SULFIDE DITHIOPHOS- PHATE Product A.Sulfurized tert.-ctylphenol A 4-necked 3 liter flask equipped with a stirrer, thermometer, reflux condenser and dropping funnel was charged with 1.5 liters of ethylene dichloride and 412 g. (2 mol) of tert.-octylphenol (prepared by reacting phenol with diisobutylene in the presence of a catalyst). After the phenol had dissolved, 135 g. (1 mol) of sulfur monochloride was added dropwise from thedropping funnel over a period of 1% hrs. during which time the reaction temperature rose from 25 C. to 38 C., with copious evolution of hydrogen chloride. The reaction solution was stirred under reflux (86 C.) for 18 hours. The solvent was then removed from the product by nitrogen blowing on the steam bath, yielding a straw-colored viscous liquid which analyzed 13.0% S (sulfur).
Product B.-Sulfurized terL-octylpheliol dithiophosphoric acid 379 g. (0.8 mol) of sulfurized terL-octylphenol (Product A) was placed in a 3-necked 2 liter flask equipped with a stirrer, thermometer, and reflux condenser. The viscous material was fluidized by heating to about 70 C., after which 88.8 g. (0.4 mol) of P285 was added. The mixture was heated at 160 C. for 2 hours with rapid stirring, after which it was dissolved in 1 liter of ethylene dichloride and filtered to remove a small amount of unreacted P285. A 15 ml. portion of the solution was poured into an evaporating dish and placed on the steam bath to remove the solvent. A dark sticky solid was obtained which analyzed 4.7% P (phosphorus) and 17.7% S.
Product C.n-Butylamine tert.-octylphenol sulfiide dithiophosphate The reaction solution containing Product B was poured into a 4-necked 2 liter flask equipped with a stirrer, thermometer, reflux condenser, and dropping funnel, after which 58.4 g. (0.8 mol) of n-butyl amine was added dropwise over a 30 minute period during which time the temperature rose from 28 C. to 46 C. After stirring at room temperature for one hour, the solution was poured into a large evaporating dish and the solvent removed by nitrogen blowing on the steam bath. An amber, tacky solid was obtained which analyzed 14.8% S, 3.9% P, and 2.0% N (nitrogen). The product was completely insoluble in CS2, diflicultly soluble in CCl4, and had a mild odor.
Product D.Hydrolysis of n-butylamine tert.-octylphenol sulfide dithiophosphate A solution of 56.0 g. (0.05 mol) of Product C in 500 ml. of dioxane was placed in a 4-necked 2 liter flask equipped with a stirrer, thermometer, reflux condenser, and dropping funnel. Over a 30 minute period, 40 g.
, (1 mol) of NaOH in 200 ml. of
H2O was added dropwise. The reaction mixture was heated at reflux with rapid stirring for 5 hours after which it was placed on the steam bath and evaporated to'dryness. The light yellow pasty mass was mixed with about 400 ml. of hot water and neutralized by the addition of HCl. The aqueous mixture was extracted with 3-200 ml. portions of ether. The ether extract was dried over anhydrous Na2SO4. Evaporation of the solvent yielded a sticky reddish black solid which analyzed 13.9% S, 0.8% I, and 2.3% N. This material was practically odorless. EXAMPLE 2.PREPARATION OF PRIOR ART PRODUCTS In order to obtain a direct comparison of the products A 3-necked 2 liter flask equipped with a stirrer, thermometer and condenser was charged with 412 g. (2 mol) of tert.-octylphenol. After heating to melt the phenol, 111 g. of P2S5 (0.5 mol) was added with stirring after which the reaction mixture was heated at C. for 2 hours. The product was then dissolved in ethylene dichloride and filtered to remove a small amount of unreacted P285. After removal of the solvent on the steam bath, a viscous brown liquid was obtained which analyzed 6.2% P and 9.7% S.
Product F.Reaction of tert.-octylphenol dithiophosphoric acid with sulfur monochloride 430 g. of Product E, tert.-octylphenol dithiophosphoric acid (0.85 mol) was dissolved in 800 ml. of ethylene dichloride. The solution was poured into a 4-necked 2 liter flask equipped with a stirrer, thermometer, reflux condenser, and dropping funnel. 57.4 g. of sulfur monochloride (0.425 mol) was then added dropwise over a period of 45 minutes with no temperature rise and a mild evolution of hydrogen chloride. The reaction mixture was heated at reflux (86 C.) with stirring for 18 hours after which the solvent was removed by N2 blowing on the steam bath. A reddish brown tacky solid was obtained which analyzed 5.7% P and 14.8% S.
Product G.Treatment of Product F with n-butylamine Product F was dissolved in 1 liter of ethylene dichloride and the solution was poured into a 4-necked 2 liter flask equipped with a stirrer,- thermometer, reflux condenser and dropping funnel. 62.0 g. (0.85 mol) of n-butylamine was then added over a 30 minute period during which time the temperature rose from 30 C. to 33 C. After stir-ring at room temperature for 1 hour, the solution was poured into an evaporating dish for removal of the solvent. A black viscous liquid was obtained which analyzed 4.7% P, 12.7% S, and 2.2% N. This product was readily soluble in both CS: and CCL; and had a strong disagreeable odor.
Product H .Hydrolysis of Product G This hydrolysis was carried out by the same procedure as described in making Product D using 54.0 g. of Product G. A dark solid was obtained which analyzed 0.3% P, 1.8% N, and 4.3% S and possessed an unpleasant, phenolic odor.
EXAMPLE 3.COMPARISON OF PHYSICAL AND CHEMICAL CHARACTERISTICS OF PRODUCTS C AND G In view of the marked differences in physical and chemical characteristics of the two products, it is possible to draw the following conclusions:
Product C consists chiefly of compounds having-the approximate average formula:
s sn-mNtotm 0 BEN C 2 17 08H CH having the following theoretical analysis: N-1.2 wt. percent, Sl 6.7 wt percent, P5.4 wt.-percent.
The structure ofProduct C arises from the fact that the reaction of a phenol and sulfur halide'is known to form a phenol sulfide containing one-or more sulfur atoms interconnecting benzene nuclei. Subsequent reaction with phosphorus pentasulfide forms the dithiophosphate having an available'sulfhydryl group which in turn reacts with the amine. Evidence of reaction'of the amine and thiophosphate is further shown inthat a temperature rise of 16 C. occurred when the amine was added. Drastic hydrolysis of product C resultedin substantially no reduction of the sulfur content of the'compound. This is characteristic of the sulfur bridge between aromatic nuclei, such bridges not beingrsusceptible to hydrolysis even under severe conditions.
Product G, on the other handyappears to be chiefly a polysulfi-de derivative of diaryldithiophosphoric: acid .in which the hydrogen of the sulfhydryl groups of two molecules :of-the. dithiophosphoric acid, formed by reacting phenol and-P285, is removedyand the two resultingradicals are joined by'oneor more atoms -.of sulfur when reacted with sulfur'halide. Nowacid groupsare available for further reaction. Thisagrees with experimental data. There was no evidence of reaction between the polysultide and the amine since substantiallyno temperature increase occurred when the'two materials were :mixed together. The amine appeared to be present. in a mechanically occluded state or as a loose coordination compound with the polysulfide. Additional evidence that Product G is a polysulfide compound arises from the fact-that drastic hydrolysis of this material, under the identical conditions used in hydrolyzing product C, resulted in a loss of approximately two-thirds of the sulfur content and most of the phosphorus. It is characteristic that the sulfur of such polysulfide structures is relatively loosely bound and is quite susceptible to hydrolysis.
Additional evidence of the marked difierences in chemical structure between products C and G is found in the fact that the former compound was insoluble in carbon disulfide whereas the latter compound was readily soluble inthis solvent.
EXAMPLE 4.-COMPARISON OF LUBRICANT AD- DITIVE' PROPERTIES OF PRODUCTSC AND G Phorone detergency test Blends containing 1% by weight each of products C and G in a paraflinic-type mineral lubricating oil of SAE-3O grade and a sample of the unblended base oil were submitted to adetergencyrtest designed to measure the effectiveness of theadditives for preventing harmful engine deposits in internal combustion engines. The test is conducted as follows: 100 g. of testoil 'are weighed into a clean, 300 cc. tall-form, open glass beaker provided with a stirrer. The beaker is placed in an oil bath maintained at a-temperature of 275 'F. After stirring the test oil for 10 minutes, 10 cc. of phorone and a measured amount of 10% sulfuric acid are added. The mixture is then stirred for one hour during which time a synthetic sludge is formed. The oil is poured off, the beaker-is rinsed with heptane, wiped with a clean cloth to remove loose deposits, dried and'then weighed to determine the amount of tenaciously adhering deposits'remaining in the beaker. The amount of tenaciously adhering deposits correlates with engine deposits formed in heavy duty internal combustion engines operating at relatively high temperatures.
Several runs were carried out on each blend in which the amount of sulfuric acid added was varied. From these data, the phorone number, which is defined as the cubic centimeters of 10% sulfuric acid required to form 10 mgs. of beaker deposits, is determined. A relatively high phorone number is indicative of an additive having good detergency characteristics- The results of the tests follow: TABLE.I.-PHORONE DETERGENCY TEST Beaker Deposit, mgs.
cc.ot10% H2804 Base Oil Base Oil Base Oil 1 a 1 a Product Product O G 48 3 p 22 0 39 0.5 2e 14 Phoronc N 0., ea. 10% 112804110 form 10 mg. beaker deposits 2 2. 1 0. 3
1 Not determined. 1 Obtained by interpolation of plotted data.
It. is seen from this test that Product C is approximately seven times more efl ective in detergency character? istics than Product G at a deposit level of 10 mg. Product G imparted substantially no beneficial detergency properties to the lubricant base stock.
Bearing Corrosion tests Blends containing 0.25 each of the products C and G in an acid-treated naphthenic-type mineral lubricating oil having a viscosity at F. of 355 SUS, and a sample of the unblended base oil, were submitted to a' corrosion test designed to measure the effectiveness of the products-in inhibiting the corrosiveness of a typical min-- eral lubricating oil toward the surfaces of copper-lead bearings. The test was conducted as follows: 500 cc. of the oil was placed in a glass oxidation tube (13 inches long and 2% inches in diameter) fitted at the bottom with a /1 inch air inlet tube perforated to facilitate air distribution. The oxidation tube was then immersed in a heating bath so that the oil temperature was maintained at 325 F during the test. Two quarter sections of automotive bearings of copper-lead alloy of known weight having a total area of 25 sq. cm. were attached to opposite sides of a stainless steel rod which was then immersed in the test'oil and rotated at 600 R. P. M., thus providing sufiicient agitation of the sample during the test. Air was then blown through the oil at therate of 2 cu. ft. per hour. At the end of each 4-hour period the hearings were removed, washed with naphtha and weighed to determine the amount of loss by corrosion. The bearings were then repolished (to increase-the'severity of the test) ,reweighed, and then subjected to the test for additional 4-hour periods in likemanner. The results are given in Table II as corrosion life, which indicates the number of hours 'required for the bearings to lose 100 mg. in weight, determined by interpolation of the data obtained in the various periods.
TABLEIL- t HOUR BEARING CORROSION TEST 4-Hour S. O. D. Life (Hrs. to lose 100 mg./25 sq. cm. Cu-Pb Bearing Surface) Blend Base Oil Base on +0.25% Product ml Base Oil +0.25% Product G H Product C is more than 3.5 times as effective as Product G as a corrosioninhibitor.
EXAMPLE 5.PREPARATION OF ISOPROPYL- AMINE SALT OF TERT.-OCTYL PHENOL SUL- FIDE TI-HOPHOSPHATE sulfide so prepared (containing 1.5 gram atoms of sulfur per mol), and 716 g. of a refined light lubricating oil of approximately SAE10 grade was heated in a 4 liter beaker until a homogeneous solution was obtained (90 C.). 111 g. of P285 was added and the reaction temperature was increased to 140 C. and maintained at this point for 4 hours, followed by filtration to remove a small amount of insoluble material. The filtrate was placed in a 4 liter beaker, and a solution of 118 g. of isopropylarnine in 300 g. of a refined light lubricating oil of approximately SAE-10 grade was added over a 2 hour period, with rapid stirring, the temperature being kept at 4050 C. by means of an ice bath. The product was then left on the steam bath overnight with nitrogen blowing, followed by filtration to remove a slight haze. The product was a dark red, viscous, practically odorless concentrate containing 1.86% phosphorus and 6.92% sulfur. The calculated values for a 40% concentrate of /P\ 0 O @SMQ CsHn CaHr! are 2.01% phosphorus and 7.32% sulfur.
A lubricant blend containing the product of this example was submitted to a bearing corrosion test conducted by the conditions described in Example IV. The base stock employed was an SAE grade paraflinic-type mineral lubricating oil having a bearing corrosion life of 10 hours. This base oil containing 0.25% by weight of the isopropyl amine salt of tert.-octyl phenol sulfide thiophosphate had a bearing corrosion life of 33 hours.
The products of the present invention may be employed not only in ordinary hydrocarbon lubricating oils but also in the heavy duty type of lubricating oils which have been compounded with such detergent type additives as metal soaps, metal petroleum sulfonates, metal phenates, metal alco'holates, metal alkyl phenol sulfides, metal organo phosphates, thiophosphates, phosphites and thiophosphites, metal salicylates, metal xanthates and thioxanthates, metal thiocarbamates, amines and amine derivatives, reaction products of metal phenates and sulfur, re action products of metal phenates and phosphorus sulfides, metal phenol sulfonates, and the like. Thus, the additives of the present invention may be used in lubrieating oils containing such other addition agents as bariurn tert.-octylphenol sulfide, calcium tert.-amylphenol sulfide, nickel oleate, barium stearate, calcium phenyl stearate, zinc diisopropyl salicylate, aluminum naphthenate, calcium cetyl phosphate, barium di-tert.-amylphenol sulfide, calcium petroleum sulfonate, zinc methyl cyclohexyl thiophosphate, calcium dichlorostearate, etc. Other types of additives such as phenols and phenol sulfides may be employed.
The lubricating oil base stocks used in the compositions of this invention may be straight mineral lubricating oils or distillates derived from paraflinic, naphthenic, asphaltic or mixed base crudes, or, if desired, various blended oils may be employed as well as residuals, particularly those from which asphaltic constituents have been carefully removed. The oils may be refined by conventional methods using acid, alkali and/or clay or other agents such as aluminum chloride, or they may be extracted oils produced, for example, by solvent extraction with solvents of the type of phenol, sulfur dioxide, furfural, dichlorod-iethyl ether, nitrobenzene, crotonaldehyde, etc. Hydrogenated oils or white oils may be employed as well as 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. In certain instances cracking coil tar fractions and coal tar or shale oil distillates may also be used. Also, for special application, animal, vegetable or fish oils or their hydrogenated or voltolized products may be employed in admixture with mineral oils.
For the best results the base stock chosen should normally be that oil which without the new additive present gives the optimum performance in the service contemplated. However, since one advantage of the additives is that their use also makes feasible the employment of less satisfactory mineral oils or other oils, no strict rule can be laid down for the choice of the base stock. Certain essentials must of course be observed. The oils must possess the viscosity and volatility characteristics known to be required for the service contemplated. The oil must be a satisfactory solvent for the additive, although in some cases auxiliary solvent agents may be used; 7 The lubricating oils, however they may have been produced, may vary considerably in viscosity and other properties depending upon the particular use for which they are desired, but they usually range from about 40 to 150 sec- 0nd Saybolt viscosity at 210 F. For the lubrication of certain low and medium speed diesel engines the general practice has often been to use a lubricating oil base stock prepared from naphthcnic or aromatic crudes and having a Saybolt viscosity at 210 F. of 45 to seconds and a viscosity index of 0 to 50. However, in certain types of diesel engine and other gasoline engine service, oils of higher viscosity index are often preferred, for example, up to 75 to 100, or even higher, viscosity index.
In addition to the material to be added according to the present invention, other agents may also be used such as dyes, pour depressors, heat thickened fatty oils,.sulfurized fatty oils, organo-metallic compounds, metallic or other soaps, sludge dispersers, antioxidants, thickeners, viscosity index improvers, oiliness agents, resins, rubber, olefin polymers, voltolized fats, voltolized oils, and/or voltolized waxes and colloidal solids such as graphite or zinc oxide, etc. Solvents and assisting agents, such as esters, ketones, alcohols, aldehydes, halogenated or nitrated compounds, and the like may also be employed.
Assisting agents which are particularly desirable as plasticizers and def oamers are the higher alcohols having eight or more carbon atoms and preferably 12 to 20 carbon atoms. The alcohols may be saturated straight and branched chain aliphatic alcohols such as octyl alcohol (CBHI'IOH), lauryl alcohol (C12H25OH), cetyl alcohol (CrsHzaOH), stearyl alcohol, sometimes referred to as octadecyl alcohol (C18H3'IOH), heptadecyl alcohol (C17H35OH), and the like, the corresponding olefinic alcohols such as oleyl alcohol; cyclic alcohols such as naphthenic alcohols; and aryl substituted alkyl alcohols,'for
instance, phenyl octyl alcohol, or octadecyl benzyl alcohol or mixtures of these various alcohols, which may be pure or substantially pure synthetic alcohols. One may also use mixed naturally occurring alcohols such as those found in wool fat (which is known to contain a substantial percentage of alcohols having about 16 to 18 carbon atoms) and in sperm oil (which contains a high percentage of cetyl alcohol); and although it is preferable to isolate the alcohols from those materials, for some purposes, the wool fat, sperm oil or other natural products rich in alcohols may be used per se. Products prepared synthetically by chemical processes may also be used, such as .alcohols prepared by the oxidation of petroleum hydrocarbons, e. g. paraflin wax, petrolatum, etc.
In addition to being employed in crankcase lubricants the additives of the present invention may also be used in extreme pressure lubricants, engine flushing oils, industrial oils, general machinery oils, process oils, rust preventive compositions and greases.
The additives of the present invention may be employed as antioxidant or stabilizing agents not only in mineral lubricating oils, but also in petroleum hydrocarbon products generally, where improved resistance to oxidation is desired. Thus the products may be added to motor oils, diesel fuels, kerosene, waxes, hydrocarbon polymers, etc. and other mineral oils.
The present invention is not to be considered as limited by any of the examples described herein, which are given by way of illustration only, but it is to be limited solely by the terms of the appended claims.
What is claimed is:
1. A lubricating oil composition comprising a major proportion of a mineral lubricating oil and a minor, oxi dation inhibiting amount of a product obtained by react- 10 ing about 2 moles of an alkyl phenol sulfide having the formula:
OH OH R S: R
where R is an alkyl group having in the range of about 4 to 20 carbon atoms and x represents an integer of about 1 to 3, with about 1 mole of P285 at a temperature of about to C. for about 2 to 4 hours, and thereafter reacting the resulting alkyl phenol sulfide-P285 reaction product with about 2 moles of a primary aliphatic amine, selected from the group consisting of n-butylamine and isopropylamine.
2. A lubricating oil composition comprising a major proportion of a mineral lubricating oil and about 0.1 to 2.0% by weight, based on the total composition, of a prodnot obtained by reacting about 2 moles of tert. octyl phenol sulfide with about 1 mole of P285 at a temperature of about 140 to 160 C. for about 2 to 4 hours, and thereafter reacting the resultant tert. octyl phenol sulfide-P285 reaction with about 2 moles of a primary aliphatic amine selected from the group consisting of n-butylarnine and isopropylamine.
References Cited in the file of this patent UNITED STATES PATENTS
Claims (1)
1. A LUBRICATING OIL COMPOSITION COMPRISING A MAJOR PROPORTION OF A MINERAL LUBRICATING OIL AND A MINOR, OXIDATION INHIBITING AMOUNT OF A PRODUCT OBTAINED BY REACTING ABOUT 2 MOLES OF AN ALKYL PHENOL SULFIDE HAVING THE FORMULA:
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US329112A US2766207A (en) | 1952-12-31 | 1952-12-31 | Hydrocarbon oil products |
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US329112A US2766207A (en) | 1952-12-31 | 1952-12-31 | Hydrocarbon oil products |
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US2766207A true US2766207A (en) | 1956-10-09 |
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US329112A Expired - Lifetime US2766207A (en) | 1952-12-31 | 1952-12-31 | Hydrocarbon oil products |
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3002014A (en) * | 1958-07-30 | 1961-09-26 | Monsanto Chemicals | S-amine phosphorothioates |
US3159578A (en) * | 1960-02-26 | 1964-12-01 | Shell Oil Co | Organic functional fluids and polymeric amine salt additives therefor |
US4377527A (en) * | 1981-03-09 | 1983-03-22 | Standard Oil Company (Indiana) | Ammonia catalyzed preparation of zinc dihydrocarbyl dithiophosphates |
US5102566A (en) * | 1987-10-02 | 1992-04-07 | Exxon Chemical Patents Inc. | Low ash lubricant compositions for internal combustion engines (pt-727) |
US5141657A (en) * | 1987-10-02 | 1992-08-25 | Exxon Chemical Patents Inc. | Lubricant compositions for internal combustion engines |
WO2001012761A1 (en) * | 1999-08-17 | 2001-02-22 | Exxonmobil Research And Engineering Company | Crystal formation reduction in lubricating compositions |
WO2001012762A1 (en) * | 1999-08-17 | 2001-02-22 | Exxonmobil Research And Engineering Company | Crystal formation inhibition in lubricating compositions |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2362624A (en) * | 1943-01-21 | 1944-11-14 | Standard Oil Co | Lubricant |
US2556963A (en) * | 1946-07-15 | 1951-06-12 | Gaudin Olivier | Benzenes containing sulfur in their allylic or propenylic side chains and process of preparing them |
-
1952
- 1952-12-31 US US329112A patent/US2766207A/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2362624A (en) * | 1943-01-21 | 1944-11-14 | Standard Oil Co | Lubricant |
US2556963A (en) * | 1946-07-15 | 1951-06-12 | Gaudin Olivier | Benzenes containing sulfur in their allylic or propenylic side chains and process of preparing them |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3002014A (en) * | 1958-07-30 | 1961-09-26 | Monsanto Chemicals | S-amine phosphorothioates |
US3159578A (en) * | 1960-02-26 | 1964-12-01 | Shell Oil Co | Organic functional fluids and polymeric amine salt additives therefor |
US4377527A (en) * | 1981-03-09 | 1983-03-22 | Standard Oil Company (Indiana) | Ammonia catalyzed preparation of zinc dihydrocarbyl dithiophosphates |
US5102566A (en) * | 1987-10-02 | 1992-04-07 | Exxon Chemical Patents Inc. | Low ash lubricant compositions for internal combustion engines (pt-727) |
US5141657A (en) * | 1987-10-02 | 1992-08-25 | Exxon Chemical Patents Inc. | Lubricant compositions for internal combustion engines |
WO2001012761A1 (en) * | 1999-08-17 | 2001-02-22 | Exxonmobil Research And Engineering Company | Crystal formation reduction in lubricating compositions |
WO2001012762A1 (en) * | 1999-08-17 | 2001-02-22 | Exxonmobil Research And Engineering Company | Crystal formation inhibition in lubricating compositions |
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