CN101024655B - 含硫含磷化合物的盐及其制备方法 - Google Patents
含硫含磷化合物的盐及其制备方法 Download PDFInfo
- Publication number
- CN101024655B CN101024655B CN2006100639970A CN200610063997A CN101024655B CN 101024655 B CN101024655 B CN 101024655B CN 2006100639970 A CN2006100639970 A CN 2006100639970A CN 200610063997 A CN200610063997 A CN 200610063997A CN 101024655 B CN101024655 B CN 101024655B
- Authority
- CN
- China
- Prior art keywords
- compound
- alkyl
- amine
- hydrogen
- salt
- 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 - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 82
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 150000003839 salts Chemical class 0.000 title claims abstract description 25
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 22
- 239000011574 phosphorus Substances 0.000 title claims abstract description 22
- 229910052717 sulfur Inorganic materials 0.000 title claims abstract description 21
- 239000011593 sulfur Substances 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims description 46
- -1 nitrogenous compound Chemical class 0.000 claims description 69
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 150000001412 amines Chemical class 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 229920001021 polysulfide Polymers 0.000 claims description 12
- 239000005077 polysulfide Substances 0.000 claims description 12
- 150000008117 polysulfides Polymers 0.000 claims description 12
- 150000001721 carbon Chemical group 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 description 31
- 125000001183 hydrocarbyl group Chemical group 0.000 description 13
- 239000005864 Sulphur Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000314 lubricant Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 238000005987 sulfurization reaction Methods 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000005299 abrasion Methods 0.000 description 5
- 150000003973 alkyl amines Chemical class 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920013639 polyalphaolefin Polymers 0.000 description 4
- 150000003141 primary amines Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000008431 aliphatic amides Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- XXUJMEYKYHETBZ-UHFFFAOYSA-N ethyl 4-nitrophenyl ethylphosphonate Chemical compound CCOP(=O)(CC)OC1=CC=C([N+]([O-])=O)C=C1 XXUJMEYKYHETBZ-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 description 3
- TYQTYRXEMJXFJG-UHFFFAOYSA-N phosphorothious acid Chemical class OP(O)S TYQTYRXEMJXFJG-UHFFFAOYSA-N 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001149 thermolysis Methods 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- JECLIFURJWCALG-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) dihydrogen phosphite Chemical compound OCC(C)(C)COP(O)O JECLIFURJWCALG-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- NYLJHRUQFXQNPN-UHFFFAOYSA-N 2-(tert-butyltrisulfanyl)-2-methylpropane Chemical compound CC(C)(C)SSSC(C)(C)C NYLJHRUQFXQNPN-UHFFFAOYSA-N 0.000 description 2
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 125000005265 dialkylamine group Chemical group 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- 150000003009 phosphonic acids Chemical class 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- VSAISIQCTGDGPU-UHFFFAOYSA-N phosphorus trioxide Inorganic materials O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- 125000002769 thiazolinyl group Chemical group 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- UATFHWVUSDADRL-FPLPWBNLSA-N (z)-hexadec-9-en-1-amine Chemical compound CCCCCC\C=C/CCCCCCCCN UATFHWVUSDADRL-FPLPWBNLSA-N 0.000 description 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- POACDWSNBNLUDD-UHFFFAOYSA-N 1-butoxybutane;1,4-dioxane Chemical compound C1COCCO1.CCCCOCCCC POACDWSNBNLUDD-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- NYSLGVBILCQCOS-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;trihydroxy(sulfanylidene)-$l^{5}-phosphane Chemical compound OP(O)(O)=S.OCC(C)(C)CO NYSLGVBILCQCOS-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- FIWYWGLEPWBBQU-UHFFFAOYSA-N 2-heptylphenol Chemical compound CCCCCCCC1=CC=CC=C1O FIWYWGLEPWBBQU-UHFFFAOYSA-N 0.000 description 1
- MTANQWXSMWFCNJ-UHFFFAOYSA-N 5,5-dimethyl-1,3,2-dioxaphosphinane Chemical compound CC1(C)COPOC1 MTANQWXSMWFCNJ-UHFFFAOYSA-N 0.000 description 1
- AAIUWVOMXTVLRG-UHFFFAOYSA-N 8,8-dimethylnonan-1-amine Chemical compound CC(C)(C)CCCCCCCN AAIUWVOMXTVLRG-UHFFFAOYSA-N 0.000 description 1
- 241000567772 Cetorhinus maximus Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 1
- XOCUXOWLYLLJLV-UHFFFAOYSA-N [O].[S] Chemical compound [O].[S] XOCUXOWLYLLJLV-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001356 alkyl thiols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- OSPSWZSRKYCQPF-UHFFFAOYSA-N dibutoxy(oxo)phosphanium Chemical compound CCCCO[P+](=O)OCCCC OSPSWZSRKYCQPF-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000012208 gear oil Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- JOVBTVIBOUJCPQ-UHFFFAOYSA-N hydroxy-bis(2-methylpropoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)COP(O)(=S)OCC(C)C JOVBTVIBOUJCPQ-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 125000005645 linoleyl group Chemical group 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- NMBXMBCZBXUXAM-UHFFFAOYSA-N n-butyl-1-dibutoxyphosphorylcyclohexan-1-amine Chemical compound CCCCOP(=O)(OCCCC)C1(NCCCC)CCCCC1 NMBXMBCZBXUXAM-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ZXRDVSMSMOZCPT-UHFFFAOYSA-N phosphorodithious acid Chemical compound OP(S)S ZXRDVSMSMOZCPT-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000010734 process oil Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical group CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000005323 thioketone group Chemical group 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657109—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms esters of oxyacids of phosphorus in which one or more exocyclic oxygen atoms have been replaced by (a) sulfur atom(s)
- C07F9/657118—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms esters of oxyacids of phosphorus in which one or more exocyclic oxygen atoms have been replaced by (a) sulfur atom(s) non-condensed with carbocyclic rings or heterocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
- C07F9/1652—Polyol derivatives esterified at least twice by thiophosphoric acid groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/10—Thio derivatives
- C10M137/105—Thio derivatives not containing metal
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16H—GEARING
- F16H57/00—General details of gearing
- F16H57/04—Features relating to lubrication or cooling or heating
-
- 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
- C10M2223/043—Ammonium or amine salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/047—Thioderivatives not containing metallic elements
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- 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
- C10M2223/049—Phosphite
-
- 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
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- 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
- C10N2030/08—Resistance to extreme temperature
-
- 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
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Mechanical Engineering (AREA)
- Lubricants (AREA)
Abstract
本文公开了一种含硫含磷化合物的盐。还公开了制备所述盐的方法。
Description
相关申请
本申请享有申请日为2005年11月9日提交的美国临时申请No.60/734,757的优先权。
技术领域
本申请涉及一种含硫含磷化合物的盐及其制备方法。
背景技术
含磷化合物用于润滑剂组合物的应用是已知的。尤其是，含磷化合物通常含直链烷基链。然而，这些化合物存在问题的是，已知在完全配制(fullyformulated)的齿轮润滑剂中这些化合物在高温下是热不稳定的。热不稳定化合物很可能在润滑剂组合物中过早分解并且将不再对润滑剂组合物提供例如抗磨损的特性。
润滑剂组合物例如齿轮油通常要经历高温，因此提供一种不会在高温下过早分解的热稳定化合物将是有益的。热稳定化合物可就此长时间保留在润滑剂组合物中并为组合物长时间提供例如抗磨损的特性。因此需要具有适当热稳定性以维持其抗磨损特性的化合物。
发明内容
根据本发明，其公开了一种油溶性的式(III)化合物：
其中R1、R2、R3、R4、R5、R6、R7、R8和R9独立地选自氢、氰基和含约1-约30个碳原子的烃基。
本发明还公开了式(VI)的化合物：
其中n是1-5的整数；和
其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10和R11独立地选自氢、氰基和含约1-约30个碳原子的烃基。
另一方面，本发明公开了一种制备含硫含磷化合物的盐的方法，包括：提供含硫化合物、含氮化合物和至少一种式(I)和式(IV)的化合物：
其中n是1-5的整数；和
其中R1、R2、R3、R4、R5、R6、R10和R11独立地选自氢、氰基和含约1-约30 个碳原子的烃基。
进一步地本发明还公开了包含含氮化合物、新戊二醇亚磷酸酯和含硫化合物的反应产物的组合物。
本发明的其它目的和优点将部分地在随后说明阐明，和/或可通过本发明的实践获悉。本发明的目的和优点通过在权利要求中所特别提出的要素和组合来实现和获得。
应当理解的是上述一般性描述以及下文的详细说明仅是示范性的和说明性的，而不是对所要求保护的本发明的限制。
图1是说明各种含磷物质的热稳定性的图。
附图说明
本发明更具体地涉及如下方面：
具体实施方式
1.一种油溶性的式(III)化合物：
其中R1、R2、R3、R4、R5、R6、R7、R8和R9独立地选自氢、氰基和含约1-约30个碳原子的烃基。
2.项目1的化合物，其中R3、R4、R5、R6、R7和R8是氢，R1和R2是甲基，并且R9是叔C12-14烷基其中R1、R2、R3、R4、R5、R6、R10和R11独立地选自氢、氰基和含约1-约30个碳原子的烃基。
6.项目5的方法，其中在式(I)化合物中R3、R4、R5和R6是氢；并且R1和R2是甲基。
其中n是1-5的整数；和
其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10和R11独立地选自氢、氰基和含约1-约30个碳原子的烃基。
4.项目3的化合物，其中R1和R2是甲基，R3、R4、R5、R6、R7和R8是氢；R9是叔C12-14烷基；并且R10和R11是含约1-约6个碳原子的烷基。
5.一种制备含硫含磷化合物的盐的方法，包括：
提供含硫化合物、含氮化合物和至少一种式(I)和(IV)的化合物：
其中n是1-5的整数；和
6.项目5的方法，其中在式(I)化合物中R3、R4、R5和R6是氢；并且R1和R2是甲基。
7.项目5的方法，其中在式(IV)化合物中R1和R2是甲基；R3、R4、R5和R6是氢；并且R10和R11是含约1-约6个碳原子的烷基。
8.项目5的方法，其中含硫化合物选自元素硫、多硫化物和硫化烯烃。
9.项目8的方法，其中含硫化合物是元素硫。
10.项目5的方法，其中使用至少等摩尔当量或更多的含硫化合物。
11.项目5的方法，其中反应温度为约23℃-约90℃。
12.项目5的方法，其中所述含硫含磷化合物的盐是式(III)和(VI)化合物中的至少一种：
其中n是1-5的整数；和
其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10和R11独立地选自氢、氰基和含约1-约30个碳原子的烃基。
13.项目12的方法，其中在式(III)中R3、R4、R5、R6、R7和R8是氢；R1和R2是甲基；并且R9是叔C12-14烷基。
14.项目12的方法，其中在式(VI)中R1和R2是甲基，R3、R4、R5、R6、R7和R8是氢；R9是叔C12-14烷基；并且R10和R11是含约1-约6个碳原子的烷基。
15.项目5的方法，其中含氮化合物是胺。
16.项目5的方法，其中含氮化合物选自直链胺和支化胺。
17.项目16的方法，其中胺是选自C8-16叔烷基伯胺混合物和C14-24叔烷基伯胺混合物的支化胺。
18.项目16的方法，其中含氮化合物是直链胺。
19.项目5的方法，其中使用约0.05至约2摩尔当量的含氮化合物。
20.项目11的方法，其中所述方法进行约1至约8小时。
21.一种组合物，其包含含氮化合物、新戊二醇亚磷酸酯和含硫化合物的反应产物。
在这里所使用的术语“烃基取代基”或“烃基”代表以本领域技术人员所公知的其普通含义使用。更具体是指，具有直接与分子其余部分连接的碳原子并且具有主导烃特征的基团。烃基的实例包括：
(1)烃取代基，更确切地说，脂肪族的(例如烷基或烯基)、脂环族的(例如环烷基、环烯基)取代基和芳香族-、脂肪族-和脂环族-取代的芳香族取代基，以及通过分子的另一部分形成环的环状取代基(例如两个取代基一起形成脂环基)；
(2)取代的烃取代基，更确切地说，含有在本发明情况下不改变主导烃取代基的非烃基团(例如，卤代(特别是氯和氟代)、羟基、烷氧基、巯基、烷基巯基、硝基、亚硝基和硫氧基(sulfoxy))的取代基；
(3)杂取代基，更确切地说，在本发明情况下具有主导烃特征但同时在环或链中除碳原子外还含有非碳原子的取代基。杂原子包括硫、氧、氮，并涵盖取代基例如吡啶基、呋喃基、噻吩基和咪唑基。通常而言，在烃基中对于每十个碳原子至多有两个非烃取代基，例如至多有一个非烃取代基；一般地在烃基中没有非烃取代基。
这里所使用的术语“重量百分数”，除非特别声明，是指所述组分与整个组合物重量的百分比。
一方面，本发明提供了一种具有改善的抗磨损性和热稳定性中至少一种特性的化合物。所述化合物可以是含硫含磷化合物和/或其盐，它可含有位阻从而使化合物在高温下的分解最小化和/或阻止其分解。本发明的化合物和/或其盐可显示出改善的热稳定性，因此比那些不包括位阻的组合物更长期地保留在润 滑剂组合物中。所述位阻可以任何形式存在，例如以烃基链支化、附属(dependant)烃基链等等形式存在。
在本发明方法中可使用含磷化合物，例如亚磷酸酯或磷酸酯。制备亚磷酸酯和磷酸酯的方法是已知的。例如，亚磷酸酯可通过亚磷酸或者不同亚磷酸酯与各种醇反应来制备。另一种合成方法包括使三氯化磷与过量的醇反应。此外，环状亚磷酸酯可通过亚磷酸酯与二醇的酯交换反应来制备，所述酯交换反应可得到单体和聚合产物的混合物。参见Oswald，Alexis A.，“Synthesis of CyclicPhosphorous Acid Esters by Transesterification，”Can.J.Chem.，37：1498-1504(1959)；和Said，Musa A.等人，“Reactivity of Cyclic Arsenites and Phosphites：X-raystructures of bis(5，5-dimethyl-1，3，2-diosarsenan-2-yl)ether and bis(2，4，8，10-tetra-tert-butyl-12H-dibenzo[d，g][1，3，2-dioxarsenocin-6-yl)ether，”J.Chem.Soc.，22：2945-51(1995)，所述文献的公开内容通过引用并入本文。制备环状氢代硫代亚磷酸酯(hydrogen thiophosphites)的方法也是已知的，例如在吡啶的存在下通过使环状氯代亚磷酸酯与硫化氢反应来制备。参见Zwierzak，A.，“Cyclicorganophosphorus compounds.I.Synthesis and infrared spectral studies of cyclichydrogen phosphites and thiophosphites.Can.J.Chem.，45：2501-12(1967)，所述文献的公开内容通过引用并入本文。
在一方面，亚磷酸酯可以是亚磷酸的二或三烃基酯。各个烃基可以具有约1到约24个碳原子，或1到约18个碳原子，或约2到约8个碳原子。各个烃基可以独立地是烷基、烯基、芳基及其混合物。当烃基是芳基时，其可以含有至少约6个碳原子；或约6到约18个碳原子。烷基或烯基的非限制性例子包括丙基、丁基、己基、庚基、辛基、油基(oleyl)、亚油基(linoleyl)、硬脂基等等。芳基的非限制性例子包括苯基、萘基、庚基苯酚等。在一方面，各个烃基可以独立地是甲基、丙基、丁基、戊基、己基、庚基、油基或苯基，例如甲基、丁基、油基或苯基，和进一步例如甲基、丁基、油基或苯基。
可用的亚磷酸酯的非限制性例子包括氢代膦酸二丁酯(dibutyl hydrogenphosphonate)、氢代膦酸二异丁酯、氢代膦酸二油基酯、氢代膦酸二(C14-18)酯、亚磷酸三苯酯、亚磷酸二烃基酯诸如式(I)化合物、和聚合物型亚磷酸酯诸如式(IV)化合物，式(I)和式(IV)的化合物如下所示：
其中n为约1到约5的整数；和
其中R1、R2、R3、R4、R5、R6、R10和R11可独立地选自氢、氰基和含约1到约30个碳原子的烃基，例如含约1到约20个碳原子的烃基，和进一步例如含约1到约10个碳原子的烃基。在一方面，如果n为大于约5的整数，则不受任何特定理论限制，相信重复单元将不会完全硫化。
在一方面，在式(I)的化合物中，R3、R4、R5和R6可以是氢；R1和R2可以是甲基。该化合被通称为亚磷酸新戊二醇酯(NPGP)并且在化学文摘库登记号为CAS#4090-60-2(5，5-二甲基-1，3，2-二氧磷杂环己烷(dioxaphosphorinan)-2-酮)。在一方面，在式(IV)的化合物中，R1和R2可以是甲基；R3、R4、R5和R6可以是氢；并且R10和R11可以是含约1到约6个碳原子的烷基。该化合物是在制备亚磷酸新戊二醇酯的过程中产生的聚合物型副产物。
含磷化合物还可以是磷酸酯或其盐、亚磷酸或亚磷酸酐与不饱和化合物的反应产物中的至少一种，或其两种或多种的混合物。
二硫代磷酸金属盐可以通过使金属碱与至少一种硫代亚磷酸(其可以是单硫代亚磷酸或二硫代亚磷酸)反应制备。
亚磷酸或亚磷酸酐可以与不饱和化合物反应，所述不饱和化合物包括但不限于酰胺、酯、酸、酸酐和醚类。
在一方面，含磷化合物，如亚磷酸酯，可以包括各种增加所述化合物的位阻并因此增加所述化合物抵抗热分解能力的官能团。在一方面，含磷化合物可以在烃基链中的相对氧原子的β位置处支化。据信在该β-碳原子上的支化可改变(例如可改善)所述含磷化合物在润滑剂组合物中的热稳定性。
此外，含磷化合物可使用那些增加所生成的化合物的位阻的组分制备。例如，用于制备如亚磷酸酯的醇可以是β-支化醇。β-支化醇的非限制性例子包括异丁醇、2-乙基己醇、新戊二醇、新戊醇、姥鲛烷醇(pristanol)和甲基异丁基甲醇(MIBC)。
本文公开的含磷化合物可用作起始材料以得到含硫含磷化合物的盐。在一方面，制备含硫含磷化合物的盐的方法可以包括提供诸如上述那些的含磷化合物、含硫化合物和含氮化合物以得到含硫含磷化合物的盐。在另一方面，本发明包括一种组合物，其包含含氮化合物、含磷化合物例如亚磷酸新戊二醇酯和含硫化合物的反应产物。与非含硫含磷化合物相比，所述反应产物可提供改善的抗磨损特性。
含硫化合物可以是任何包含游离硫和/或活性硫的化合物。含硫化合物的非限制性例子包括硫化的动物或植物脂肪或油，硫化的动物或植物脂肪酸酯，三价或五价磷酸的完全酯化或部分酯化的酯，硫化烯烃，二烃基多硫化物，硫化的狄尔斯-阿德耳反应加成物，硫化的二环戊二烯，脂肪酸酯和单不饱和烯烃的硫化或共硫化混合物，脂肪酸、脂肪酸酯和α-烯烃的共硫化共混物，官能团取代的二烃基多硫化物，硫醛、硫酮及其衍生物(例如酸、酯、亚胺或内酯)，环硫化合物，含硫的缩醛衍生物，萜烯和非环状烯烃的共硫化共混物，多硫化物烯烃产物，和元素硫。
在一方面，含硫化合物可通过使烯烃如异丁烯与硫反应制备。产物如硫化异丁烯或硫化聚异丁烯通常具有的硫含量为10到55重量％，例如30到50重量％。可使用各种其它的烯烃或不饱和烃例如异丁烯二聚物或三聚物用于形成这种含硫化合物。
在另一方面，多硫化物由一种或多种由式R20-Sx-R21表示的化合物组成，其中R20和R21可以是各自可含有约3到约18个碳原子的烃基，x可以为约2到约8，例如为约2到约5，可进一步例如为3。烃基可以是各种类型的烃基，如烷基、环烷基、烯基、芳基或芳烷基。可以使用叔烷基多硫化物如二叔丁基三硫化物， 和包含二叔丁基三硫化物的混合物(例如主要由或完全由三、四和五硫化物组成的混合物)。其它有用的二烃基多硫化物的例子包括二戊基多硫化物、二壬基多硫化物和二(十二烷基)多硫化物和二苄基多硫化物。
每一当量的含磷化合物可以使用至少是等摩尔的或更多的含硫化合物。在一方面，可使用约1到约1.5摩尔当量的含硫化合物。
本文公开的方法可包括溶剂的使用。溶剂可以是反应物中至少一种可溶于其中或者产物可溶于其中的任何惰性流体物质。溶剂的非限制性例子包括苯、甲苯、二甲苯、正己烷、环己烷、石脑油、二乙基醚卡必醇、二丁醚二氧杂环己烷、氯苯、硝基苯、四氯化碳、氯仿、聚α-烯烃、原油(base oil)和工艺用油。
所公开的方法进一步包括提供含氮化合物。含氮化合物可以帮助促进所公开的含磷化合物的硫化和/或可帮助中和任何的酸。可使用任何含氮化合物，只要其可溶于润滑剂组合物中即可，所述润滑剂组合物可包含原油。含氮化合物的非限制性例子包括酰胺、胺和含碱性氮的杂环化合物如吡啶。在一方面，含氮化合物是胺，其可以是伯胺、仲胺或叔胺。
在一方面，烃基胺可以是在烃基中含约4到约30个碳原子的伯烃基胺，例如在烃基中含约8到约20个碳原子的伯烃基胺。烃基可以是饱和或不饱和的。饱和的伯胺的典型例子是已知作为脂肪族伯脂肪胺的那些。典型的脂肪胺包括烷基胺如正己基胺、正辛基胺、正癸基胺、正十二烷基胺、正十四烷基胺、正十五烷基胺、正十六烷基胺、正十八烷基胺(硬脂胺)等。这些伯胺以蒸馏级或工业级获得。蒸馏级可提供更纯的反应产物，而工业级的胺可在反应中形成酰胺和酰亚胺。混合的脂肪胺也是适当的。
在一方面，所公开的化合物的胺盐可以是来自在烷基中具有至少约4个碳原子的叔脂肪族伯胺的那些。对于大部分，它们可来自在烷基中具有总共低于约30个碳原子的烷基胺。
通常，叔脂肪族伯胺是由下式表示的单胺：
其中R1、R2和R3可以相同或不同并且可以是含约1到约30个碳原子的烃基。这种胺的示例性例子为叔丁基胺、叔己基伯胺、1-甲基-1-氨基-环己烷、叔辛基伯胺、叔癸基伯胺、叔十二烷基伯胺、叔十四烷基伯胺、叔十六烷基伯胺、叔十八烷基伯胺、叔二十四烷基伯胺、叔二十八烷基伯胺。
胺的混合物也可用于本公开的目的。这种类型的胺的混合物的示例性例子可以是C8-C16叔烷基伯胺的混合物，和类似的C14-C24叔烷基伯胺的混合物。叔烷基伯胺及其制备方法是本领域普通技术人员公知的，因此没有必要进一步讨论。可用于本公开目的的叔烷基伯胺及其制备方法在美国专利2,945,749中描述，所述文献因此方面的教导内容通过引用并入本文。
其中烃链包含烯属不饱和度的伯胺也可以是非常有用的。因此，根据链的长度，R基团可含有至少一个烯属不饱和度，通常每10个碳原子包含不超过一个双键。典型的胺是十二烯基胺、肉豆蔻油基胺(myristoleylamine)、棕榈油基胺(palmitoleylamine)、油基胺和亚油基胺。
仲胺包括具有上述烷基中两个的二烷基胺，包括脂肪仲胺，还包括混合的二烷基胺，其中R′可以是脂肪胺，R″可以是低级烷基(1-9个碳原子)如甲基、乙基、正丙基、异丙基、丁基等，或者R″可以是带有其它非活性或极性取代基(CN、烷基、烷氧羰基、酰胺、醚、硫醚、卤代、亚砜、砜)的烷基。脂肪多胺二胺可包括单-或二烷基的对称或不对称的乙二胺、丙二胺(1，2或1，3)或上述的多胺类似物。适当的脂肪多胺包括N-椰油基(coco)-1，3-二氨基丙烷，N-soya烷基三亚甲基二胺、N-牛油基(tallow)-1，3-二氨基丙烷和N-油基-1，3-二氨基丙烷。
在一方面，含氮化合物不是三乙基胺或环己基胺。
含氮化合物可以任何促成所公开的方法完成所必需的任何量被提供，即，如果不存在足够的含氮化合物，则含磷化合物不完全硫化。在一方面，含氮化合物可以相对于每当量的含磷化合物以约0.05到约2的摩尔当量被提供，例如 相对于每当量的含磷化合物提供约1到约1.5摩尔当量的含氮化合物。
本文公开的方法可以在约室温(23℃)或更高温度下进行，例如在至少约50℃进行，进一步例如在约50℃到约90℃的范围内进行。通常，在室温下混合约1分钟到约8小时的时段是足够的。
所得化合物可以是至少一种式(III)和式(VI)化合物，其结构表示如下：
其中n为1到5的整数；和
其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10和R11可独立地选自氢、氰基和含约1到约30个碳原子的烃基，例如含约1到约20个碳原子的烃基，进一步例如含约1到约10个碳原子的烃基。
在一方面，在式(III)化合物中，R3、R4、R5、R6、R7和R8可以是氢；R1和R2可以是甲基；且R9可以是叔C12-14烷基。在一方面，在式(VI)化合物中，R1和R2可以是甲基；R3、R4、R5、R6、R7和R8可以是氢；R9可以是叔C12-14烷基；且R10和R11可以是含约1到约6个碳原子的烷基。
制备所述盐的方法是公知的并且在文献中有报道。参见例如美国专利2,063,629；2,224,695；2,447,288；2,616,905；3,984,448；4,431,552；5,354,484；Pesin等人的Zhurnal Obshchei Khimii，31(8)：2508-2515(1961)；和PCT国际 申请公开WO 87/07638，所述文献的公开内容并入本文作为参考。
可单独形成含硫含磷化合物的盐，然后将其添加到润滑或功能性流体组合物中。或者，当含磷化合物(如本文公开的亚磷酸酯)与其它组分共混以形成润滑或功能性流体组合物时形成所述盐。然而，如果原地形成盐，则对存在于组合物中的酸(如防锈组分)的限制很重要，因为酸可以与含氮化合物反应并中止硫化作用和盐的形成。
含硫含磷化合物的盐可以是油溶性的，即，盐的烃基链可以足够长，如具有至少六个碳原子，使得生成的化合物可溶于配制成的组合物中。引入疏水基团可以增加在非极性介质中的溶解度。含硫含磷化合物的盐的非限制性例子包括二异丁基硫代磷酸C8-16叔烷基伯胺盐，二-2-乙基己基-硫代磷酸C8-16叔烷基伯胺盐，和新戊二醇硫代磷酸C8-16叔烷基伯胺盐。在一方面，考虑了二硫代磷酸的盐。
实施例
实施例1-新戊二醇亚磷酸酯(NPGP)与支化胺的硫化
往装备有均压加料漏斗的1L反应器中装入硫(53.3g，1.7mol)、含氮化合物(PRIMENE
81R)(320.7g，1.7mol)和4cSt聚α-烯烃(375.6g)。然后往加料漏斗中装入液体NPGP(250.04g，1.7mol)。所述NPGP在标准条件下是固体并具有约60℃到约65℃的熔点。加热加料漏斗避免凝固。
在搅拌和氮气保护气氛下，将NPGP添加到反应器中并同时保持物质温度(mass temperature)为约60℃到约90℃。根据反应体系控制放热的能力控制加料速率。该过程是放热的；因此，在加料期间需要对反应物质进行冷却。在加料完毕后，反应混合物在70到90℃搅拌2到6小时直到所有的硫耗尽。
所观察到的硫化NPGP的P-31NMR化学位移(ppm)为52.96。
如以上所讨论的，可使用任一含硫化合物用作硫源，只要存在游离的活性硫。例如，下列步骤被认为也可制备本文公开的化合物。
可往装备有均压加料漏斗的2L反应器中装入2，5-双-(t-壬基二硫)-1，3，4-噻二唑(396.8g，0.85mol)、PRIMENE81R(320.7g，1.7mol)和4Cst PAO(375.6g)。然后可往加料漏斗中装入液体NPGP(250.04g，1.7mol)。所述NPGP在标准条件下是固体，并具有约60℃到约65℃的熔点。可加热加料漏斗避免凝固。
在搅拌和氮气保护气氛下，应将NPGP添加到反应器中并同时保持物质温度为约60℃到约90℃。根据反应体系控制放热的能力控制加料速率。在加料完毕后，反应混合物可在约70到约90℃搅拌约2小时。
实施例2-新戊二醇亚磷酸酯(NPGP)与直链胺的硫化
可往装备有均压加料漏斗的1L反应器中装入硫(53.3g，1.7mol)、含氮化合物(ARMEENOL)(464.1g，1.7mol)和4cSt聚α-烯烃(375.6g)。然后可往加料漏斗中装入液体NPGP(250.04g，1.7mol)。所述NPGP在标准条件下是固体，并具有约60℃到约65℃的熔点。应加热加料漏斗避免凝固。在搅拌和氮气保护气氛下，可将NPGP添加到反应器中并同时保持物质温度为约60℃到90℃。可根据反应体系控制放热的能力控制加料速率。该过程是放热的；因此，在加料期间可能需要对反应物质进行冷却。在加料完毕后，反应混合物可在约70到约90℃搅拌约2至约6小时直到所有的硫耗尽。
实施例3-抗磨损效力
通过磷物质在高温下的持续时间测量抗磨损效力水平。完全配制的齿轮用流体置于处于约325℉下的热浴中。将小份的完全配制的齿轮用流体以定时间隔取样并测定31P核磁共振(NMR)谱。观察31P NMR谱中的磷物质并对时间和热分解绘图。生成了针对磷抗磨损性物质的曲线。磷物质的分解速率或分解量根据烃基链的化学结构的不同而改变。磷抗磨损性组分的例子是二烷基硫代磷酸胺盐。烷基支化的变化改变了二烷基硫代磷酸胺盐在325℉热浴中的热分解速率。当相对磷-氧键的β-碳原子被甲基支化或被高同系烷基支化时，热稳定作用是最有效的。增加的稳定性的例子通过图1中渐低(shallower)斜率示出。
对于本说明书和权利要求的目的，除非另有说明，所有表示数量、百分比或比例的数字以及在说明书和权利要求中使用的其它数值，可理解为是在所有情况下由术语“约”进行修饰。因此，除非有不同说明，在以下说明书和权利要求中所述的数字参数是可以根据由本发明公开所试图获得的所需性质而改变的近似值。至少地并且并不试图对与权利要求范围等价物原则的应用构成限制，每个数字参数至少应根据所报道的显著数字或通过应用通常的舍入技术而进行解释。
值得注意的是，如本说明书和权利要求使用的，单数形式“一”和“所述的”包括复数形式，除非清楚地和明确地限于是指一个。因此，例如关于“抗 氧化剂”，其包括两种或多种不同的抗氧化剂。如本文使用的，术语“包括”及其语法上的变体是非限制性的，使得在该术语下列举的项目不排除其它可以被替换或添加到所列项目中的类似项目。
尽管已经描述了具体实施方案，但是应用者或本领域的其它技术人员可以意识到目前未预见或可能目前未预见的替换物、修饰、变体、改善、实质等价物。因此，提交的和可能进行修改的权利要求试图包括所有的这些替换物、修饰、变体、改善和实质等价物。
Claims (15)
1.一种式(VI)的化合物：
其中n是1-5的整数；和
其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10和R11独立地选自氢、氰基和含1-30个碳原子的烃基。
2.权利要求1的化合物，其中R1和R2是甲基，R3、R4、R5、R6、R7和R8是氢；R9是C12-14叔烷基；并且R10和R11是含1-6个碳原子的烷基。
3.一种制备含硫含磷化合物的盐的方法，包括：
提供含硫化合物、含氮化合物和式(IV)的化合物：
其中n是1-5的整数；和
其中R1、R2、R3、R4、R5、R6、R10和R11独立地选自氢、氰基和含1-30个碳原子的烃基；和
其中所述含硫、含氮化合物的盐是式(VI)的化合物：
其中n是1-5的整数；和
其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10和R11独立地选自氢、氰基和含1-30个碳原子的烃基。
4.权利要求3的方法，其中在式(IV)化合物中R1和R2是甲基；R3、R4、R5和R6是氢；并且R10和R11是含1-6个碳原子的烷基。
5.权利要求3的方法，其中含硫化合物选自单质硫、多硫化物和硫化烯烃。
6.权利要求5的方法，其中含硫化合物是单质硫。
7.权利要求3的方法，其中使用至少等摩尔当量的含硫化合物。
8.权利要求3的方法，其中反应温度为23℃-90℃。
9.权利要求3的方法，其中在式(VI)中，R1和R2是甲基，R3、R4、R5、R6、R7和R8是氢；R9是C12-14叔烷基；并且R10和R11是含1-6个碳原子的烷基。
10.权利要求3的方法，其中含氮化合物是胺。
11.权利要求4的方法，其中含氮化合物选自直链胺和支化胺。
12.权利要求11的方法，其中胺是选自C8-16叔烷基伯胺混合物和C14-24叔烷基伯胺混合物的支化胺。
13.权利要求11的方法，其中含氮化合物是直链胺。
14.权利要求3的方法，其中使用0.05至2摩尔当量的含氮化合物。
15.权利要求3的方法，其中所述方法进行1至8小时。
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73475705P | 2005-11-09 | 2005-11-09 | |
| US60/734757 | 2005-11-09 | ||
| US11/372443 | 2006-03-09 | ||
| US11/372,443 US20070142660A1 (en) | 2005-11-09 | 2006-03-09 | Salt of a sulfur-containing, phosphorus-containing compound, and methods thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101024655A CN101024655A (zh) | 2007-08-29 |
| CN101024655B true CN101024655B (zh) | 2011-07-06 |
Family
ID=37671934
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2006100639970A Expired - Fee Related CN101024655B (zh) | 2005-11-09 | 2006-11-08 | 含硫含磷化合物的盐及其制备方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US20070142660A1 (zh) |
| EP (2) | EP2270120A1 (zh) |
| JP (1) | JP4743712B2 (zh) |
| KR (1) | KR100844299B1 (zh) |
| CN (1) | CN101024655B (zh) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8461293B2 (en) * | 2010-08-03 | 2013-06-11 | Chevron Phillips Chemical Company Lp | Methods of mercaptanizing olefinic hydrocarbons and compositions produced therefrom |
| JP6712223B2 (ja) * | 2013-12-06 | 2020-06-17 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 組成物およびその形成方法 |
| US9481696B1 (en) * | 2015-08-19 | 2016-11-01 | Afton Chemical Corporation | Thiophosphates and thiophosphate derivatives as lubricant additives |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4077860A (en) * | 1976-12-29 | 1978-03-07 | Stauffer Chemical Company | Photopolymerizable composition stabilized with ammonium salts of phosphorus acid and process |
| US4544492A (en) * | 1983-05-09 | 1985-10-01 | Ciba-Geigy Corporation | Lubricant compositions |
Family Cites Families (83)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2063629A (en) * | 1935-02-19 | 1936-12-08 | Du Pont | Esters of the thio acids of phosphorus |
| US2224695A (en) * | 1938-11-25 | 1940-12-10 | Carl F Prutton | Inhibitor |
| US2284409A (en) * | 1940-03-08 | 1942-05-26 | Pittsburgh Corning Corp | Fitting for tempered glass panels |
| US2284410A (en) * | 1940-08-22 | 1942-05-26 | John F Farmer | Adjustable end slide grille |
| US2447288A (en) * | 1946-03-06 | 1948-08-17 | Gulf Oil Corp | Primary aliphatic amine salts of dialiphatic substituted mono-thiophosphoric acids |
| US2616905A (en) * | 1952-03-13 | 1952-11-04 | Lubrizol Corp | Organic alkaline earth metal complexes and methods of making same |
| US3192162A (en) * | 1955-08-12 | 1965-06-29 | Exxon Research Engineering Co | Cyclo-organo compounds of phosphorus |
| US2945749A (en) * | 1956-04-18 | 1960-07-19 | Socony Mobil Oil Co Inc | Stabilized fuel oil containing tertiary alkyl primary amines |
| DE1248643B (de) * | 1959-03-30 | 1967-08-31 | The Lubrizol Corporation, Cleveland, Ohio (V. St. A.) | Verfahren zur Herstellung von öllöslichen aeylierten Aminen |
| NL124842C (zh) * | 1959-08-24 | |||
| US3087936A (en) * | 1961-08-18 | 1963-04-30 | Lubrizol Corp | Reaction product of an aliphatic olefinpolymer-succinic acid producing compound with an amine and reacting the resulting product with a boron compound |
| US3216939A (en) * | 1962-06-18 | 1965-11-09 | Universal Oil Prod Co | Stabilization of lubricants |
| US3184411A (en) * | 1962-09-28 | 1965-05-18 | California Research Corp | Lubricants for reducing corrosion |
| US3281428A (en) * | 1963-04-29 | 1966-10-25 | Lubrizol Corp | Reaction product of certain acylated nitrogen containing intermediates and a boron compound |
| US3338832A (en) * | 1963-04-29 | 1967-08-29 | Lubrizol Corp | Lubricating oil containing reaction product of certain acylated nitrogen containing intermediates and a boron compound |
| US3282955A (en) * | 1963-04-29 | 1966-11-01 | Lubrizol Corp | Reaction products of acylated nitrogen intermediates and a boron compound |
| GB1054276A (zh) * | 1963-05-17 | |||
| US3513093A (en) * | 1963-06-17 | 1970-05-19 | Lubrizol Corp | Lubricant containing nitrogen-containing and phosphorus-containing succinic derivatives |
| US3533945A (en) * | 1963-11-13 | 1970-10-13 | Lubrizol Corp | Lubricating oil composition |
| US3216936A (en) | 1964-03-02 | 1965-11-09 | Lubrizol Corp | Process of preparing lubricant additives |
| US3658836A (en) * | 1964-04-16 | 1972-04-25 | Monsanto Co | Hydroxyboroxin-amine salts |
| US3342735A (en) * | 1965-04-23 | 1967-09-19 | Texaco Inc | Alkenyl succinic anhydride-amine-ps reaction product |
| US3344069A (en) * | 1965-07-01 | 1967-09-26 | Lubrizol Corp | Lubricant additive and lubricant containing same |
| US3272746A (en) * | 1965-11-22 | 1966-09-13 | Lubrizol Corp | Lubricating composition containing an acylated nitrogen compound |
| US3511780A (en) * | 1966-02-09 | 1970-05-12 | Exxon Research Engineering Co | Oil-soluble ashless dispersant-detergent-inhibitors |
| US3502607A (en) * | 1966-10-31 | 1970-03-24 | Celanese Corp | Art of making dyeable polyacrylonitrile products |
| US3703536A (en) * | 1967-11-24 | 1972-11-21 | Standard Oil Co | Preparation of oil-soluble boron derivatives of an alkylene polyamine-substituted phenol-formaldehyde addition product |
| US3718663A (en) * | 1967-11-24 | 1973-02-27 | Standard Oil Co | Preparation of oil-soluble boron derivatives of an alkylene polyamine-urea or thiourea-succinic anhydride addition product |
| GB1268561A (en) * | 1969-02-06 | 1972-03-29 | Exxon Research Engineering Co | Lubricating and fuel oil compositions |
| DE2008843A1 (de) * | 1969-02-27 | 1970-09-10 | Shell Internationale Research Maatschappij N.V., Den Haag (Niederlande) | Phosphorinan-Derivate, Verfahren zu ihrer Herstellung und Schmierstoffe, die solche Verbindungen enthalten |
| GB1268562A (en) * | 1970-06-23 | 1972-03-29 | Exxon Research Engineering Co | Lubricating oil and fuel oil additives |
| GB1329978A (en) * | 1971-06-17 | 1973-09-12 | Exxon Research Engineering Co | Lubricating oil compositions |
| DE2363388C2 (de) * | 1973-12-20 | 1982-08-19 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Dialkylthiophosphaten |
| US4234435A (en) * | 1979-02-23 | 1980-11-18 | The Lubrizol Corporation | Novel carboxylic acid acylating agents, derivatives thereof, concentrate and lubricant compositions containing the same, and processes for their preparation |
| US4348291A (en) | 1979-07-02 | 1982-09-07 | Stauffer Chemical Company | Novel phosphoramides, lubricating compositions and method of improving wear and extreme pressure characteristics of lubricating oil |
| GB2081300A (en) * | 1980-07-29 | 1982-02-17 | Exxon Research Engineering Co | Gear or axle oils |
| US4431552A (en) * | 1982-11-26 | 1984-02-14 | Chevron Research Company | Lubricant composition containing an alkali-metal borate and a mixture of phosphates, monothiophosphates and dithiophosphates in a critical ratio |
| US4455243A (en) * | 1983-02-24 | 1984-06-19 | Chevron Research Company | Succinimide complexes of borated fatty acid esters of glycerol and lubricating oil compositions containing same |
| US4615826A (en) * | 1983-09-22 | 1986-10-07 | Chevron Research Company | Hydrocarbon soluble nitrogen containing dispersant-fluorophosphoric acid adducts |
| US4648980A (en) * | 1983-09-22 | 1987-03-10 | Chevron Research Company | Hydrocarbon soluble nitrogen containing dispersant - fluorophosphoric acid adducts |
| AU595358B2 (en) * | 1986-06-13 | 1990-03-29 | Lubrizol Corporation, The | Phosphorus-containing lubricant and functional fluid compositions |
| AU7870787A (en) | 1986-06-13 | 1988-01-11 | Lubrizol Corporation, The | Phosphorous- and sulfur-containing lubricant and functional fluid compositions |
| US4652387A (en) * | 1986-07-30 | 1987-03-24 | Mobil Oil Corporation | Borated reaction products of succinic compounds as lubricant dispersants and antioxidants |
| US4755311A (en) * | 1986-08-14 | 1988-07-05 | The Lubrizol Corporation | Phosphorus-, sulfur- and boron-containing compositions, and lubricant and functional fluid compositions containing same |
| US4943672A (en) * | 1987-12-18 | 1990-07-24 | Exxon Research And Engineering Company | Process for the hydroisomerization of Fischer-Tropsch wax to produce lubricating oil (OP-3403) |
| US5198133A (en) * | 1988-03-14 | 1993-03-30 | Ethyl Petroleum Additives, Inc. | Modified succinimide or sucinamide dispersants and their production |
| US4900460A (en) * | 1988-08-02 | 1990-02-13 | Mobil Oil Corp. | Sulfurized olefin adducts of dihydrocarbyl phosphates and phosphites and lubricant compositions containing same |
| US4857214A (en) * | 1988-09-16 | 1989-08-15 | Ethylk Petroleum Additives, Inc. | Oil-soluble phosphorus antiwear additives for lubricants |
| US4997968A (en) * | 1989-09-28 | 1991-03-05 | The Lubrizol Corporation | Method of preparing monothiophosphoric acid by sulfurizing a phosphite in the presence of an amide |
| CA2040819A1 (en) | 1990-05-17 | 1991-11-18 | Stephen Norman | Lubricant compositions |
| ES2079626T3 (es) | 1990-06-26 | 1996-01-16 | Ciba Geigy Ag | Compuestos dioxafosforinano como estabilizadores de materiales organicos. |
| CA2099314A1 (en) | 1992-07-09 | 1994-01-10 | Ian Macpherson | Friction modification of synthetic gear oils |
| US5358650A (en) * | 1993-04-01 | 1994-10-25 | Ethyl Corporation | Gear oil compositions |
| US6096691A (en) * | 1993-04-09 | 2000-08-01 | Ethyl Corporation | Gear oil additive concentrates and lubricants containing them |
| US5698498A (en) | 1993-06-28 | 1997-12-16 | The Lubrizol Corporation | Hydroxyalkyl dithiocarbamates, their borated esters and lubricants, functional fluids, greases and aqueous compositions containing the same |
| CA2130139C (en) * | 1993-08-20 | 2004-06-29 | Sean S. Bigelow | Lubricating compositions with improved thermal stability and limited slip performance |
| US20030096713A1 (en) * | 1994-04-19 | 2003-05-22 | Eric R. Schnur | Lubricating compositions with improved oxidation resistance containing a dispersant and an antioxidant |
| US5569644A (en) * | 1995-05-18 | 1996-10-29 | The Lubrizol Corporation | Additive combinations for lubricants and functional fluids |
| EP1389635A1 (en) * | 1995-12-08 | 2004-02-18 | ExxonMobil Research and Engineering Company | Biodegradable high performance hydrocarbon base oils |
| SG64414A1 (en) * | 1996-01-16 | 1999-04-27 | Lubrizol Corp | Lubricating compositions |
| US5882505A (en) * | 1997-06-03 | 1999-03-16 | Exxon Research And Engineering Company | Conversion of fisher-tropsch waxes to lubricants by countercurrent processing |
| WO1999018112A1 (fr) | 1997-10-06 | 1999-04-15 | Idemitsu Kosan Co., Ltd. | Composes organophosphoreux renfermant du soufre |
| US5968880A (en) | 1997-10-23 | 1999-10-19 | The Lubrizol Corporation | Lubricating compositions, functional fluids and greases containing thiophosphorus esters or their salts with a oxyalkylene group, and methods of using the same |
| US6013171A (en) * | 1998-02-03 | 2000-01-11 | Exxon Research And Engineering Co. | Catalytic dewaxing with trivalent rare earth metal ion exchanged ferrierite |
| US6180575B1 (en) * | 1998-08-04 | 2001-01-30 | Mobil Oil Corporation | High performance lubricating oils |
| US6080301A (en) * | 1998-09-04 | 2000-06-27 | Exxonmobil Research And Engineering Company | Premium synthetic lubricant base stock having at least 95% non-cyclic isoparaffins |
| US6103099A (en) * | 1998-09-04 | 2000-08-15 | Exxon Research And Engineering Company | Production of synthetic lubricant and lubricant base stock without dewaxing |
| US6165949A (en) * | 1998-09-04 | 2000-12-26 | Exxon Research And Engineering Company | Premium wear resistant lubricant |
| US6451745B1 (en) | 1999-05-19 | 2002-09-17 | The Lubrizol Corporation | High boron formulations for fluids continuously variable transmissions |
| JP4363701B2 (ja) | 1999-06-01 | 2009-11-11 | シェブロンジャパン株式会社 | ギヤ潤滑油組成物 |
| ATE466921T1 (de) * | 1999-12-22 | 2010-05-15 | Lubrizol Corp | Schmiermittel mit einer mischung aus einer molybdänkomponente, phosphorkomponente und dispergiermittel |
| EP1195426B1 (en) | 2000-10-05 | 2007-08-15 | Infineum International Limited | Lubricating oil composition for gas-fuelled engines |
| US6844300B2 (en) * | 2001-02-20 | 2005-01-18 | Ethyl Corporation | Low phosphorus clean gear formulations |
| US20030166474A1 (en) | 2002-01-31 | 2003-09-04 | Winemiller Mark D. | Lubricating oil compositions with improved friction properties |
| US6528458B1 (en) | 2002-04-19 | 2003-03-04 | The Lubrizol Corporation | Lubricant for dual clutch transmission |
| US6562765B1 (en) | 2002-07-11 | 2003-05-13 | Chevron Oronite Company Llc | Oil compositions having improved fuel economy employing synergistic organomolybdenum components and methods for their use |
| EP1544279B1 (en) | 2002-08-27 | 2016-09-28 | Nippon Oil Corporation | Lubricating composition |
| US20040192564A1 (en) * | 2003-03-25 | 2004-09-30 | Vasudevan Balasubramaniam | Bimodal gear lubricant formulation |
| US20040259743A1 (en) | 2003-06-18 | 2004-12-23 | The Lubrizol Corporation, A Corporation Of The State Of Ohio | Lubricating oil composition with antiwear performance |
| NZ545920A (en) * | 2003-09-12 | 2009-10-30 | Renewable Lubricants Inc | Vegetable oil lubricant comprising all-hydroprocessed synthetic oils |
| JP5033419B2 (ja) | 2003-09-13 | 2012-09-26 | エクソンモービル・ケミカル・パテンツ・インク | 自動車用ギアのための潤滑組成物 |
| CA2496100A1 (en) * | 2004-03-10 | 2005-09-10 | Afton Chemical Corporation | Power transmission fluids with enhanced extreme pressure characteristics |
| US20070105728A1 (en) | 2005-11-09 | 2007-05-10 | Phillips Ronald L | Lubricant composition |
-
2006
- 2006-03-09 US US11/372,443 patent/US20070142660A1/en not_active Abandoned
- 2006-11-08 JP JP2006303287A patent/JP4743712B2/ja not_active Expired - Fee Related
- 2006-11-08 CN CN2006100639970A patent/CN101024655B/zh not_active Expired - Fee Related
- 2006-11-08 EP EP10186112A patent/EP2270120A1/en not_active Withdrawn
- 2006-11-08 EP EP06023239A patent/EP1785472B1/en not_active Not-in-force
- 2006-11-09 KR KR1020060110341A patent/KR100844299B1/ko not_active IP Right Cessation
-
2008
- 2008-09-03 US US12/203,626 patent/US7928260B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4077860A (en) * | 1976-12-29 | 1978-03-07 | Stauffer Chemical Company | Photopolymerizable composition stabilized with ammonium salts of phosphorus acid and process |
| US4544492A (en) * | 1983-05-09 | 1985-10-01 | Ciba-Geigy Corporation | Lubricant compositions |
Non-Patent Citations (3)
| Title |
|---|
| Maria Michalska, et al.."Glycosylation of organic thio- and selenoacids ofPhosphorus the reaction of organic monothio acids ofphosphorus with glycosyl bromides. thiono-thiolorearrangement of glycosyl phosphorothioates".Tetrahedron34.1978,34617-622. * |
| Mikolajczyk, M. et al.."Stereochemistry of organophosphorus cyclic compounds. I.Stereospecific synthesis of cis- and trans-2-hydroxy-2-thio and(seleno)-4-methyl-1,3,2-dioxaphosphorinanes".Tetrahedron28 21.1972,28(21),5411-5422. |
| Mikolajczyk, M. et al.."Stereochemistry of organophosphorus cyclic compounds. I.Stereospecific synthesis of cis- and trans-2-hydroxy-2-thio and(seleno)-4-methyl-1,3,2-dioxaphosphorinanes".Tetrahedron28 21.1972,28(21),5411-5422. * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2270120A1 (en) | 2011-01-05 |
| CN101024655A (zh) | 2007-08-29 |
| US7928260B2 (en) | 2011-04-19 |
| JP2007131624A (ja) | 2007-05-31 |
| EP1785472B1 (en) | 2012-08-29 |
| JP4743712B2 (ja) | 2011-08-10 |
| KR20070049985A (ko) | 2007-05-14 |
| US20070142660A1 (en) | 2007-06-21 |
| KR100844299B1 (ko) | 2008-07-07 |
| EP1785472A1 (en) | 2007-05-16 |
| US20080319216A1 (en) | 2008-12-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102597190A (zh) | 含有酯的润滑组合物 | |
| KR101480202B1 (ko) | 내마모제 및 이의 윤활 조성물 | |
| EP1974000B1 (en) | Lubricant composition for a final drive axle | |
| CN102575186A (zh) | 抗磨损组合物及润滑传动装置的方法 | |
| CN102459535A (zh) | 含苹果酸衍生物的润滑组合物 | |
| CN103534341B (zh) | 作为润滑剂添加剂的芳族酰亚胺和酯 | |
| RU2012155783A (ru) | Смазочные композиции для трансмиссий автомобилей | |
| JP2007131848A5 (zh) | ||
| CN101024655B (zh) | 含硫含磷化合物的盐及其制备方法 | |
| CN101012238A (zh) | 含硫含磷化合物、其盐及其方法 | |
| CN110573599B (zh) | 用高焦磷酸酯含量的润滑剂润滑机械装置的方法 | |
| KR100828470B1 (ko) | 황-함유, 인-함유 화합물, 이의 염, 및 이의 제조 방법 | |
| CN102517131A (zh) | 润滑剂组合物 | |
| CN103209984A (zh) | 用于润滑剂组合物的含磷抗磨化合物的制备 | |
| CN101184828B (zh) | 具有改进的储存稳定性的润滑组合物 | |
| GB914412A (en) | Nitrogen-phosphorus-sulfur-containing lubricants | |
| KR20100095562A (ko) | 붕산 인지질을 포함하는 윤활제 조성물 | |
| JP5424228B2 (ja) | 硫黄を含んだリン含有化合物および／またはその塩から成る組成物、およびそれらの用途 | |
| US3073857A (en) | Method of preparing phosphorotetrathioate esters | |
| CN114402058B (zh) | 用于润滑汽车齿轮、车轴和轴承的组合物和方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20110706 Termination date: 20141108 |
|
| EXPY | Termination of patent right or utility model |