US2929828A - Lubricant additives - Google Patents
Lubricant additives Download PDFInfo
- Publication number
- US2929828A US2929828A US537278A US53727855A US2929828A US 2929828 A US2929828 A US 2929828A US 537278 A US537278 A US 537278A US 53727855 A US53727855 A US 53727855A US 2929828 A US2929828 A US 2929828A
- Authority
- US
- United States
- Prior art keywords
- oils
- reaction
- aluminum
- hydrocarbon
- product
- 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
- 239000003879 lubricant additive Substances 0.000 title description 4
- 239000000047 product Substances 0.000 claims description 29
- 229910052782 aluminium Inorganic materials 0.000 claims description 26
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 26
- 239000007795 chemical reaction product Substances 0.000 claims description 19
- 229930195733 hydrocarbon Natural products 0.000 description 33
- 150000002430 hydrocarbons Chemical class 0.000 description 33
- 239000003921 oil Substances 0.000 description 28
- 239000004215 Carbon black (E152) Substances 0.000 description 23
- 239000010687 lubricating oil Substances 0.000 description 19
- 239000000654 additive Substances 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- -1 cracked cycle stocks Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 150000001336 alkenes Chemical class 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 229920002367 Polyisobutene Polymers 0.000 description 8
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 239000002480 mineral oil Substances 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 239000001993 wax Substances 0.000 description 8
- 239000002199 base oil Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 229910052698 phosphorus Inorganic materials 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000000314 lubricant Substances 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000011574 phosphorus Substances 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 150000001993 dienes Chemical class 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000010688 mineral lubricating oil Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 239000004435 Oxo alcohol Substances 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 238000007664 blowing Methods 0.000 description 4
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 150000005673 monoalkenes Chemical class 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 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
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 239000003502 gasoline Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 235000019271 petrolatum Nutrition 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-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
- 150000007513 acids Chemical class 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 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
- 239000003245 coal Substances 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000010685 fatty oil Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 150000004715 keto acids Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- DSEKYWAQQVUQTP-XEWMWGOFSA-N (2r,4r,4as,6as,6as,6br,8ar,12ar,14as,14bs)-2-hydroxy-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1h-picen-3-one Chemical compound C([C@H]1[C@]2(C)CC[C@@]34C)C(C)(C)CC[C@]1(C)CC[C@]2(C)[C@H]4CC[C@@]1(C)[C@H]3C[C@@H](O)C(=O)[C@@H]1C DSEKYWAQQVUQTP-XEWMWGOFSA-N 0.000 description 1
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-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
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 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
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- JPUHCPXFQIXLMW-UHFFFAOYSA-N aluminium triethoxide Chemical compound CCO[Al](OCC)OCC JPUHCPXFQIXLMW-UHFFFAOYSA-N 0.000 description 1
- KMJRBSYFFVNPPK-UHFFFAOYSA-K aluminum;dodecanoate Chemical compound [Al+3].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O KMJRBSYFFVNPPK-UHFFFAOYSA-K 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 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
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011280 coal tar Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005336 cracking 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
- 239000010779 crude oil Substances 0.000 description 1
- 239000010730 cutting oil Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- VAROLYSFQDGFMV-UHFFFAOYSA-K di(octanoyloxy)alumanyl octanoate Chemical compound [Al+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O VAROLYSFQDGFMV-UHFFFAOYSA-K 0.000 description 1
- WIYAGHSNPUBKDT-UHFFFAOYSA-N dinonyl hexanedioate Chemical compound CCCCCCCCCOC(=O)CCCCC(=O)OCCCCCCCCC WIYAGHSNPUBKDT-UHFFFAOYSA-N 0.000 description 1
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910001502 inorganic halide Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- PMBXCGGQNSVESQ-UHFFFAOYSA-N n-hexyl mercaptan Natural products CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 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
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadecene Natural products CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000012186 ozocerite Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NUMNZKICGJJSHN-UHFFFAOYSA-N phenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC1=CC=CC=C1 NUMNZKICGJJSHN-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 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
- 125000004437 phosphorous atom Chemical group 0.000 description 1
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Classifications
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- C07F5/069—Aluminium compounds without C-aluminium linkages
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- C10N2040/20—Metal working
- C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
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Definitions
- This invention relates to lubricants and more particularly relates to a new class of products useful as lubricant additives. Still more particularly the invention relates to reaction products of aluminum alcoholates with phosphosulfurized hydrocarbons, to methods for preparing these reaction products, and to lubricant compositions containing these products as additives.
- additives in lubricating oil compositions are well known. These additives are used to improve one or more characteristics of the lubricating oil compositions such as viscosity index, pour point, oxidation resistance, corrosion resistance, detergency, and the like, and are employed extensively in lubricating oil compositions for internal combustion engines such as automotive and aviation engines. Due to the increasing severity of engine operation, there is a continuing and critical need for new and improved additives which are capable of imparting improved characteristics to the lubricating oil compositions. Preferably, such new additives will improve more than one characteristic or property of the oil.
- reaction products of aluminum alcoholates with phosphosulfurized hydrocarbons are outstanding lubricant additives. More particularly, these reaction products have been found to be particularly effective detergents and inhibitors for lubricating oil compositions, particularly in mineral lubricating oil compositions, used in internal combustion engines. In addition to these outstanding properties, the present reaction products have reduced tendency to evolve hydrogen sulfide upon storage and use.
- the hydrocarbon materials which may be reacted with a phosphorus sulfide in the first step of the production of additives of the present invention may be paraflins, olefins or olefin polymers, diolefins, acetylenes, aromatics or alkyl aromatics, cyclic aliphatics, petroleum fractions, such as lubricating oil fractions, petrolatums, waxes, cracked cycle stocks, or condensation products of petroleum fractions, solvent extracts of petroleum fractions, etc.
- Hydrocarbons such as bright stock residuums, lubricating oil distillates, petrolatums or paraflin waxes may be employed.
- monoolefins may be mentioned isobutylene, decene, dodecene, cetene (C octadecene (C cerotene (C melene 30), olefinic extracts from gasoline or gasoline itself, cracked cycle stocks and polymers thereof, resin oils from crude oil, hydrocarbon coal resins, cracked waxes, dehydrohalogenated chlorinated waxes, and any mixed high molecular weight alkenes obtained by cracking petroleum oils.
- a preferred class of olefins are those having at least 20 carbon Patent cc 299299828 Patented Mar.
- Such olefins may be obtained by the dehydrogenation of p'araifin waxes, by the dehydrohalogenation of long chain alkyl halides, by the synthesis of hydrocarbons from C0 and H by the dehydration of alcohols, etc.
- olefinic materials are the monoolefin polymers, in which the molecular weight ranges from to 50,000, preferably from about 250 to about 10,000. These polymers may be obtained by the polymerization of low molecular weight monoolefinic hydrocarbons, such as ethylene, propylene, butylene, isobutylene, normal and isoamylenes, or hexenes, or by the copolymerization of any combination of the above monoolefinic materials. 1
- Diolefins which may be employed include well known materials such as butadiene, isoprene, chloroprene, cyclopentadiene, 2,3-dimethylbutadiene, pentadiene-1,3, hexadiene-2,4, terpenes and the like. Acetylene and substituted acetylenes may similarly be employed.
- Another class of unsaturated hydrocarbon materials which may be advantageously employed in the preparation of the additives of this invention are high molecular weight copolymers of low molecular weight monoolefins and diolefins.
- the copolymer is prepared by controlled copolymerization of a low molecular weight olefin and a non-aromatic hydrocarbon showing the general formula C I-l in which x is 2 or a multiple of 2, in the presence of a catalyst of the Friedel-Crafts or peroxide type.
- the low molecular weight olefin is preferably an isoolefin or a tertiary base olefin preferably one having less than 7 carbon atoms per molecule.
- olefins examples include isobutylene, Z-methylbutene-1,2-ethylbutene- 1, secondary and tertiary base amyiene, hexylenes, and the like.
- non-aromatic hydrocarbons of the above formula which can be used are the conjugated diolefins listed in the preceding paragraph, diolefins such as 1,4-hexadiene, in which the double bond is not conjugated, as well as the acetylenes.
- the copolymerization is preferably carried out in the presence of aluminum chloride, boron fluoride, or benzoyl peroxide, and the copolymer is preferably one having a molecular weight of about 1,000 to 30,000.
- hydrocarbons which may be employed in a similar manner are aromatic hydrocarbons, such as benzene, naphthalene, anthracene, toluene, xylene, diphenyl, and the like, including aromatic hydrocarbons having alkyl substituents and aliphatic hydrocarbons having aryl substituents.
- a still further classof hydrocarbons which may be employed in the reaction with sulfides of phosphorus are condensation products of halogenated aliphatic hydrocarbons with an aromatic compound, produced by condensation in the presence of aluminum chloride or other Friedel-Crafts type catalyst.
- the halogenated aliphatic hydrocarbon is preferably a halogenated long chain paraffin hydrocarbon having more than 8 carbon atoms, such as paraflin wax, petrolatum, ozocerite wax, etc.
- High viscosity paraffin oils particularly heavy residual oil which has been treated with chemicals or extracted with propane or other solvents for the removal of asphalts, may be employed.
- the aromatic constituent may be naphthalene, fiuorene, phcnanthrene, anthracene, coal tar residues, and the like.
- hydrocarbon material which may be similarly employed is a resin-like oil which has a molecular weight of from about 1,000 to 2,000 or higher, obtained preferably from a paraflinic oil which has been dewaxed and which is then treated with a liquefied normally gaseous hydrocarbon, e.g., propane, to precipitate.
- a resin-like oil which has a molecular weight of from about 1,000 to 2,000 or higher, obtained preferably from a paraflinic oil which has been dewaxed and which is then treated with a liquefied normally gaseous hydrocarbon, e.g., propane, to precipitate.
- a heavy propane-insoluble fraction is a substantially wax-free and asphalt-free product having a Saybolt viscosity at 210 F. of about 1,000 to about 4,000 seconds or more.
- the preferred hydrocarbon materials of this invent on are isobutylene polymers and refined mineral lubr cating oil bright stocks.
- the polyisabutylenes useful in this invention have molecular weights in the range of about 100 to 50,000, preferably about 250 to 10,000 and more preferably about 500 to 2,000.
- the refined mineral lubricating oil bright stocks are preferably those which have been deasphalted, solvent extracted or acid treated, dewaxed and filtered, having SSU viscosities at 210 F. in the range of about 100 to 200, preferably about 130 to 170.
- the phosphorus sulfide-hydrocarbon reaction product may be readily obtained by reacting a phosphorus sulfide, e.g., P P 8 P 8 P 8 or other phosphorus sulfide, preferably P 8 with the hydrocarbon at a temperature of about 200 F. to about 600 F., and preferably from about 300 F. to about 550 F., using from about 1 to about 10, preferably about 2 to about 5, molecular proportions of hydrocarbon to 1 molecular proportion of the sulfide of phosphorus in the reaction. It is advantageous to maintain a non-oxidizing atmosphere, such as an atmosphere of nitrogen, above the reaction mixture.
- a non-oxidizing atmosphere such as an atmosphere of nitrogen
- the preferred ratio is one molecular proportion of the sulfide of phosphorus to two to five molecular proportions of polymer. In such case the reaction is continued until all or substantially all of the phosphorus sulfide has reacted.
- the reaction time is not critical, and the time required to cause the maximum amount of phosphorus sulfide to react will vary greatly with the temperature. A reaction time of 2 to 10 hours is frequently necessary. If desired, the reaction product may be further treated by blowing with steam; alcohol, ammonia, or an amine at an elevated temperature of about 200 F.
- the phosphosulfurized hydrocarbons will generally contain at least 1.0%, usually at least 2.0%, by weight of chemically combined sulfur.
- the phosphosulfurized hydrocarbons prepared as do scribed above are believed to be predominantly dihydrocarbon phosphinodithioic acids having the formula P R ⁇ SH where R and R are each derived from a molecule of the hydrocarbon.
- the proportions of hydrocarbon and phosphorus sulfide will be selected to form a product derived from about 2 molecules of the hydrocarbon and containing 1 phosphorus atom.
- the phosphosulfurized hydrocarbons are reacted with an aluminum alcoholate having the formula Al(OR) and more'particularly the formula alcoholates useful in the present invention are aluminum methylate, aluminum ethylate, aluminum propylate, aluminum amylate, aluminum octylate, aluminum dodecylate, aluminum octadecylate. aluminum dipropyl-monoamylate.
- These aluminum alcoholates useful in the present invention are prepared by well-known methods. For example, they may be prepared by direct action of alcohols on metallic aluminum in the presence of mercury or mercury compounds. Where the reaction is too vigorous, it is moderated by mixing the alcohol with a light petroleum fraction such as petroleum ether.
- reaction between the aluminum alcoholate and the phosphosulfurized hydrocarbon is carried out utilizing about 1 to 2 moles of the phosphosulfurized hydrocarbon per mole of aluminum alcoholate, preferably using approximately equimolar proportions of the phosphosulfurized hydrocarbon and aluminum alcoholate.
- reaction temperatures in the range of about to 450 may be used. Preferred reaction temperatures are in the range of about 200 to 350 F. A reaction temperature of about 275 to 325 F. is particularly preferred.
- the reaction may be carried out for a period of time of about 0.2 to 10 hours, preferably about 2 to 6 hours. A reaction time of about 3 to 5 hours is particularly preferred.
- the reaction may be very effectively carried out utilizing a solvent such as, for example, a mineral lubricating oil.
- the solvent when a solvent is employed, it is preferred to employ the solvent in proportions to form a composition containing about 25% to 75% active ingredient (the reaction product of the aluminum alcoholate with the phosphosulfurized hydrocarbon).
- the by-product alcohol formed in the reaction may be removed from the reaction mixture by any one of a number of methods such as blowing with an inert gas, preferably at an elevated temperature, e.g., 150 to 450 F., or distillation under vacuum.
- oxygen-containing reaction prod uct formed in accordance with the present invention is predominantly one or both of the following compounds:
- R, R R and R have their aforementioned definitions.
- the particular proportions of these two types of products in the final reaction products will depend upon the molar proportions of reactants employed. More specifically, the formation of the first-listed compound will be favored by the use of equimolar proportions of phosphosulfurized hydrocarbon and aluminum alcoholate whereas the second-listed compound will be favored by using about 2 moles of the phosphosulfurized hydrocar' bon per mole of aluminum alcoholate.
- additives of the present invention When additives of the present invention are employed in lubricating oils, they are preferably added in proportions of about 0.01 to about 20.0% or more, preferably about 0.5 to 10.0%, and more preferably about 1.0 to 6.0% by weight. , The proportions giving the best results will vary somewhat according to the nature of the additive, the nature of the lubricating oil base stock to which it is added and the specific purpose which the lubricant is to serve in a given case. For commercial purposes, 'it is'convenient to prepare concentrated oil solutionsin' whichthe amount of additivein the composition ranges from to 50% by weight, and to transport and store them in such form. In preparing a lubricating oil composition for use as a crankcase lubricant the additive concentrate is merely blended with the base oil in the required amount.
- 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 alcoholates, 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, reaction 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 alcoholates, metal alkyl phenol sulfides, metal organo phosphates, thiophosphates, phosphites and thio
- additives of the present invention may be used in lubricating oils containing such other addition agents as barium tert.-octyl-phenol sulfide, calcium tert.-amylphenol sulfide, nickel oleate, barium octadecylate, ca cium phenyl stearate, zinc diisopropyl salicylate, aluminum naphthenate, calcium cetyl phosphate, barium di-tert.- amylphenol sulfide, calcium petroleum sulfonate, zinc methylcyclohexyl thiophosphate, calcium dichlorostearate, etc.
- Other types of additivcs 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 paraffinic, 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, dichlorodiethyl ether, nitrobenzene, crotonaldehyde, etc.
- Hydrogenated oils, white oils, or shale oil may be employed as well as synthetic oils, such as esters and polyethers as well as those 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.
- synthetic oils such as esters and polyethers as well as those 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.
- animal, vegetable or fish oils or their hydrogenated or voltolized products may be employed in admixture with mineral oils.
- Synthetic lubricating oils may also be employed which have a viscosity of at least SSU at 100 F.
- esters of monobasic acids e.g., ester of C Oxo alcohol with C Oxo acid, ester of C Oxo alcohol with octanoic acid, etc.
- esters of dibasic acids e.g., di-2- ethyl hexyl sebacate, di-nonyl adipate, etc.
- esters of glycols e.g. C Oxo acid diester of tetraethylene glycol, etc.
- complex esters e.g.
- the complex ester formed by reacting one mole of sebacic acid with two moles of tetraethylene glycol and two moles of 2ethyl-hexanoic acid complex ester formed by reacting one mole of tetraethylene glycol with two moles of sebacic acid and two moles of 2-ethyl hexanol
- esters of phosphoric acid e.g.
- halocarbon oils e.g. the polymer of chlorotrifiuoroethylene containing twelve recurring units of chlorotrifiuoroethylene
- alkyl silicates e.g. methyl polysiloxanes, ethyl polysiloxanes, methyl-phenyl polysiloxanes, ethyl-phenyl polysiloxanes, etc.
- sulfite esters e.g.
- carbonates e.g. the carbonate formed by reacting C Oxo alcohol with ethyl carbonate to form a half ester and reacting this half ester with tetraethylene glycol
- mercaptals e.g. the mercaptal formed by reacting Z-ethyl hexyl mercaptan with formaldehyde
- formals e.g. the formal formed by reacting C 0x0 alcohol with formaldehyde
- polyglycol type synthetic oils e.g. the compound formed by condensing butyl alcohol with fourteen units of propylene oxide, etc.
- mixtures of any of the above (or with mineral oils) in any proportions may also be used.
- 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 oil 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.
- the lubricating oils 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 seconds Saybolt viscosity at 210 F.
- the general practice has often been to use a lubricating oil base stock prepared from naphthenic or aromatic crudes and having a Saybolt viscosity at 210 F. of 45 to seconds and a viscosity index of O to 50.
- oils of higher viscosfty 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, anti-oxidants, thickeners, viscosity index improvers, oiliness agents, resins, rubber, olefin polymers, voltolized fats, voltolized mineral 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.
- the additives of the present invention may also be used in motor fuels, hydraulic fluids, torque converter fluids, cutting oils, flushing oils, turbine oils or transformer oils industrial oils, process oils and generally as detergents and inhibitors in mineral oil products. They may also be used in gear lubricants and greases.
- Example I.-Preparati0n of reaction product of aluminum amylate with P S' -treated polyisobutylene A reaction product of aluminum amylate with P 5 where R and R are each derived from a molecule of polyisobutylene (1100 molecular weight) was prepared *7 in the following manner: 100 grams of polyisobutylene (M.W. 1100 Staudinger) were heated with 10 grams of P 5 at 425 F. for hours in a stream of nitrogen. This material was cooled to 350 F. and 110 grams of a solvent extracted parafiinic mineral oil distillate added. The product was filtered. The product contained 1.14% phosphorus and 2.35% sulfur.
- Example II.Evaluation of product A in Caterpillar 1A Test A lubricating oil composition was then prepared which consisted essentially of 6 weight percent of product A (described in Example I) and 94 weight percent of a mineral lubricating oil (hereinafter termed base oil).
- the base oil was approximately 75% of a solvent extracted neutral mineral oil and of a solvent extracted mineral oil bright stock (both of Mid-Continent origin). This oil corresponded to an S.A.E. grade product and had an SSU viscosity at 210 F. of about 65 and a viscosity index of about 102.
- This lubricating oil composition, containing 6 weight percent of product A, was then evaluated in an engine made by the Caterpillar Tractor Co.
- an oxygen-containing reaction product obtained by reacting about one mole of an aluminum alcoholate having the formula where R' is an aliphatic hydrocarbon group containing 1 to'20 carbon atoms with about 1 to 2 moles of a phosphosulfurized olefinic hydrocarbon at a temp rature between about to 450 F. fora period of time between about 0.2 to 10 hours with the removal of alcohol.
- an oxygen-containing reaction prodduct obtained by reacting about one mole of an aluminum alcoholate having the formula where R is an alkyl group containing about 3 to 8 carbon atoms with about 1 to 2 moles of 21 P 8 treatedolefinic hydrocarbon at a temperature between about 200 to 35051 for a period of time between about 2 to 6 hours with the removal of alcohol.
- an oxygen-containing reaction prodnot obtained by reacting about one hole of aluminum amylate with about one mole of a P S -treated polyisobutylene having a molecular weight of about 500 to 2,000 at a temperature of about 300 F. for about 4 hours, and then blowing the reaction product with nitrogen until essentially free from alcohol.
- an oxygen-containing reaction product obtained by reacting one molar proportion of an aluminrm alcoholate having the formula AKOR');
- the method which comprises reacting about 1 molar proportion of an aluminum alcoholate having the formula Al(OR) where R is an alkyl radical containing 3 to 8 carbon atoms.
- a method for preparing a product useful as a lubricating oil additive which comprises reacting about one mole ofaluminum amylate with about one mole of a P S -treated'polyisobutylene having a molecular weight of about 500t o 2,000 at a temperature of about 300 F. for about 4 hours, and then blowing the reaction prodnot with nitrogen until essentially free from alcohol.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US537278A US2929828A (en) | 1955-09-28 | 1955-09-28 | Lubricant additives |
GB24812/56A GB793152A (en) | 1955-09-28 | 1956-08-14 | Lubricant additives |
DEE12929A DE1128423B (de) | 1955-09-28 | 1956-09-08 | Verfahren zur Herstellung von Schmieroelzusatzstoffen |
FR1158893D FR1158893A (fr) | 1955-09-28 | 1956-09-27 | Additifs pour lubrifiants |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US537278A US2929828A (en) | 1955-09-28 | 1955-09-28 | Lubricant additives |
Publications (1)
Publication Number | Publication Date |
---|---|
US2929828A true US2929828A (en) | 1960-03-22 |
Family
ID=24141983
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US537278A Expired - Lifetime US2929828A (en) | 1955-09-28 | 1955-09-28 | Lubricant additives |
Country Status (4)
Country | Link |
---|---|
US (1) | US2929828A (fr) |
DE (1) | DE1128423B (fr) |
FR (1) | FR1158893A (fr) |
GB (1) | GB793152A (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1137732B (de) * | 1960-04-23 | 1962-10-11 | Kalk Chemische Fabrik Gmbh | Verfahren zur Herstellung von Metallkomplexen der Dialkyldithiophosphine |
DE1166191B (de) * | 1960-04-07 | 1964-03-26 | Kalk Chemische Fabrik Gmbh | Verfahren zur Herstellung von Metallkomplexen der Dialkyldithiophosphine |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113136256A (zh) * | 2021-04-09 | 2021-07-20 | 西安航天动力试验技术研究所 | 一种煤基抗磨液压油及其制备方法 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2274302A (en) * | 1940-01-22 | 1942-02-24 | Standard Oil Co | Compounded oil |
US2422585A (en) * | 1944-05-08 | 1947-06-17 | Standard Oil Co | Lubricant |
US2427272A (en) * | 1944-05-18 | 1947-09-09 | Socony Vacuum Oil Co Inc | Mineral oil composition |
US2506570A (en) * | 1945-10-05 | 1950-05-09 | Socony Vacuum Oil Co Inc | Lubricating oil compositions |
US2613205A (en) * | 1949-04-23 | 1952-10-07 | Standard Oil Dev Co | Product of reaction of phosphorus sulfide, and hydrocarbon, with guanidine carbonate |
US2688013A (en) * | 1950-11-04 | 1954-08-31 | Continental Oil Co | Light metal thiocyanate derivatives of phosphor-sulfurized aliphatic hydrocarbons |
US2724725A (en) * | 1954-01-26 | 1955-11-22 | Lubrizol Corp | Preparation of phosphinothioic halides from phosphinodithioic acids and hydrogen halides |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE843852C (de) * | 1950-08-06 | 1952-07-14 | Basf Ag | Verfahren zur Herstellung von Schwefel und Phosphor enthaltenden Schmieroelverbesserungsmitteln |
-
1955
- 1955-09-28 US US537278A patent/US2929828A/en not_active Expired - Lifetime
-
1956
- 1956-08-14 GB GB24812/56A patent/GB793152A/en not_active Expired
- 1956-09-08 DE DEE12929A patent/DE1128423B/de active Pending
- 1956-09-27 FR FR1158893D patent/FR1158893A/fr not_active Expired
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2274302A (en) * | 1940-01-22 | 1942-02-24 | Standard Oil Co | Compounded oil |
US2422585A (en) * | 1944-05-08 | 1947-06-17 | Standard Oil Co | Lubricant |
US2427272A (en) * | 1944-05-18 | 1947-09-09 | Socony Vacuum Oil Co Inc | Mineral oil composition |
US2506570A (en) * | 1945-10-05 | 1950-05-09 | Socony Vacuum Oil Co Inc | Lubricating oil compositions |
US2613205A (en) * | 1949-04-23 | 1952-10-07 | Standard Oil Dev Co | Product of reaction of phosphorus sulfide, and hydrocarbon, with guanidine carbonate |
US2688013A (en) * | 1950-11-04 | 1954-08-31 | Continental Oil Co | Light metal thiocyanate derivatives of phosphor-sulfurized aliphatic hydrocarbons |
US2724725A (en) * | 1954-01-26 | 1955-11-22 | Lubrizol Corp | Preparation of phosphinothioic halides from phosphinodithioic acids and hydrogen halides |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1166191B (de) * | 1960-04-07 | 1964-03-26 | Kalk Chemische Fabrik Gmbh | Verfahren zur Herstellung von Metallkomplexen der Dialkyldithiophosphine |
DE1137732B (de) * | 1960-04-23 | 1962-10-11 | Kalk Chemische Fabrik Gmbh | Verfahren zur Herstellung von Metallkomplexen der Dialkyldithiophosphine |
Also Published As
Publication number | Publication date |
---|---|
DE1128423B (de) | 1962-04-26 |
GB793152A (en) | 1958-04-09 |
FR1158893A (fr) | 1958-06-20 |
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