DE1282828B - Esterschmieroel - Google Patents
EsterschmieroelInfo
- Publication number
- DE1282828B DE1282828B DES90657A DES0090657A DE1282828B DE 1282828 B DE1282828 B DE 1282828B DE S90657 A DES90657 A DE S90657A DE S0090657 A DES0090657 A DE S0090657A DE 1282828 B DE1282828 B DE 1282828B
- Authority
- DE
- Germany
- Prior art keywords
- ester lubricating
- acid
- ppm
- lubricating oil
- ester
- 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.)
- Pending
Links
- 150000002148 esters Chemical class 0.000 title claims description 16
- 239000010687 lubricating oil Substances 0.000 title claims description 13
- 229910019142 PO4 Inorganic materials 0.000 claims description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 6
- 239000010452 phosphate Substances 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 11
- -1 diaryl haloalkyl phosphates Chemical class 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 235000021317 phosphate Nutrition 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 6
- 239000005069 Extreme pressure additive Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 4
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 229920006389 polyphenyl polymer Polymers 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- CXURGFRDGROIKG-UHFFFAOYSA-N 3,3-bis(chloromethyl)oxetane Chemical compound ClCC1(CCl)COC1 CXURGFRDGROIKG-UHFFFAOYSA-N 0.000 description 1
- STGFANHLXUILNY-UHFFFAOYSA-N 3,7-dioctyl-10h-phenothiazine Chemical compound C1=C(CCCCCCCC)C=C2SC3=CC(CCCCCCCC)=CC=C3NC2=C1 STGFANHLXUILNY-UHFFFAOYSA-N 0.000 description 1
- VRWHPVMGJTYPLS-UHFFFAOYSA-N 3-chloro-2,2-bis(chloromethyl)propan-1-ol Chemical compound OCC(CCl)(CCl)CCl VRWHPVMGJTYPLS-UHFFFAOYSA-N 0.000 description 1
- LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 1
- QTHRIIFWIHUMFH-UHFFFAOYSA-N 3-chloropropyl dihydrogen phosphate Chemical compound OP(O)(=O)OCCCCl QTHRIIFWIHUMFH-UHFFFAOYSA-N 0.000 description 1
- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
- LRUDIIUSNGCQKF-UHFFFAOYSA-N 5-methyl-1H-benzotriazole Chemical compound C1=C(C)C=CC2=NNN=C21 LRUDIIUSNGCQKF-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 101150023426 Ccin gene Proteins 0.000 description 1
- ASMQGLCHMVWBQR-UHFFFAOYSA-N Diphenyl phosphate Chemical group C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229940067597 azelate Drugs 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 239000011436 cob Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- MHZDONKZSXBOGL-UHFFFAOYSA-N propyl dihydrogen phosphate Chemical compound CCCOP(O)(O)=O MHZDONKZSXBOGL-UHFFFAOYSA-N 0.000 description 1
- 239000013514 silicone foam Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
-
- 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
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
-
- 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
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
-
- 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
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
- C10M2207/122—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms monocarboxylic
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
- C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/22—Acids obtained from polymerised unsaturated acids
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- C10N2040/12—Gas-turbines
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Lubricants (AREA)
Description
BUNDESREPUBLIK DEUTSCHLAND
DEUTSCHES
PATENTAMT
AUSLEGESCHRIFT
Int. CL:
ClOm
Deutsche Kl.: 23 c-1/01
Nummer: 1 282 828
Aktenzeichen: P 12 82 828.3-43 (S 90657)
Anmeldetag: 21. April 1964
Auslegetag: 14. November 1968
CO
CO
CO
Es sind schon verschiedene organische Stoffe als Zusatz zu Esterschmierölen empfohlen worden, um
ihnen Hochdruck- oder Extrerndruckeigenschaften zu verleihen, z. B. chlorierte Di- und Polyphenylverbindungen.
Solche Zusätze müssen aber auch »sauber« sein, womit gemeint ist, daß sie unter abbauenden
Arbeitsbedingungen des Motors keinen Anlaß zur Niederschlagsbildung geben. Außerdem
müssen sie auch thermisch stabil sein, da Esterschmieröle bei hohen Temperaturen eingesetzt werden.
Es ist nun gefunden worden, daß gewisse neue Diarylhalogenalkylphosphate als Extremdruckzusätze
besonders geeignet sind, insbesondere wenn sie in relativ geringen Mengen zu Esterschmierölen
zugesetzt werden, und daß sie auch die erforderlichen Eigenschaften der Sauberkeit und thermischen Stabilität
aufweisen. Sie wirken weit besser als die bekannten Zusatzstoffe.
Das erfindungsgemäße, 0.1 bis K) Gewichtsprozent eines Diarylhalogenalkylphosphats enthaltende
Esterschmieröl isl dadurch gekennzeichnet, daß es
ein Diarylhalogenalkylphosphat der allgemeinen Formel
RO
Esterschmieröl
CH,C(Y),
RO
worin R Arylreste sind, die gegebenenfalls durch
eine oder mehrere Ci m-Alkylreste substituiert sein
können. X Sauerstoff oder Schwefel bedeutet und Y gleiche oder verschiedene Reste von CH>C1,
CFlCIi. CCIn. CHi und C2Hr1 sind, wobei jedoch
nur ein CHa- oder C2H.-,-Rest vorhanden ist. enthält.
Die neuen Diarylhalogenalkylphosphate. die in den Esterschmierölen gemäß der Erfindung verwendet
werden, können am besten hergestellt werden durch Umsetzen eines 3-Halogenalkyloxetans mit Salzsäure
und darauffolgende Behandlung des bei dieser Reaktion gebildeten Alkohols mit einem Phosphorsäurechlorid
von der allgemeinen Formel
RO
RO
P-Cl
in welcher R und X die vorstehend angegebene Bedeutung haben.
Beispiele für diese neuen Diarylhalogenalkylphosphate sind Diphenyl-2.2 -bis-(chlormethyl)-3
- chlorpropylphosphat. Diphenyl - 2.2 - bis - (chlor-Anmelder:
Shell Internationale Research Maatschappij N. V.. Den Haag
Vertreter:
Dr. E. Jung, Patentanwalt,
8000 München 23, Siegesstr. 26
Als Erfinder benannt:
Derek Southern Heswall, Wirral, Cheshire;
Francis Henry Waight,
Eastham, Wirral, Cheshire;
Alexander Colquhoun Barr Macphail,
Little Sutton, Wirral, Cheshire (Großbritannien)
Beanspruchte Priorität:
Großbritannien vom 23. April 1963 (15 953)
methyl) - 3 - chlorpropylphosphorthionat, Dioctylphenyl-2,2-bis-(chlormethyl)-3-chlorpropylphosphat,
Dioctylphenyl - 2,2 - bis -(chlormethyl) - 3 -chlorpropylphosphorthionat.
Die nachstehenden Angaben dienen zur Erläuterung der Herstellungsmethode der neuen Extremdruckzusatzstoffe.
Herstellungsverfahren I
Diphenyl-2,2-bis-(chlormethyl)-3-chlorpropylphosphat
3.3-Bis-(chlormethyl)-oxetan (989 g) (6,38 Mol) werden in eine 2-1-Flasche eingebracht, die mit
einem bis zum Boden der Flasche reichenden Einführungsrohr, einem Thermometer und einem Kondensator
mit einem Gaszuführungsrohr versehen isl. Das Oxetan wird bis zum Schmelzen erhitzt,
und dann wird während 2 Stunden Chlorwasserstoff durch die Flasche hindurchgeblasen. In dieser
Zeit erhöht sich die Reaktionstemperatur langsam bis zu einem Maximum von 110 C. Das Reaktions-
809 637/882
3 4
produkt wird erst mit verdünnter Natriumcarbonat- durch Waschen mit NaOH-Lösung aktiviert worden
lösung, dann mit Wasser bis zur neutralen Reaktion ist. Nach dem Filtrieren wird das Lösungsmittel abgewaschen
und schließlich destilliert. Das so erhaltene destilliert, wobei ein bernsteinfarbiges flüssiges Pro-2,2-Bis-(chlormethyl)-3-chlorpropanol
hat folgende dukt zurückbleibt, welches Di-p-octylphenyl-2,2-di-Analysendaten:
5 (chlormethylJ-S-chlorpropylphosphat ist und die fol
genden Analysenwerte ergibt:
Chlor (Gewichtsprozent) 53,9
Hydroxylwert 5,12 Säurewert 0,7 mg/KOH/g
Freies Chlorid 0
100 g (0,52 Mol) des 2,2-Bis-(chlormethyl)-3-chlor- io Chlor (Gewichtsprozent) 16,45
propanols, 134 g (0,5MoI) Phosphorsäurediphenyl-
esterchlorid und Pyridin (50 g) (0,63 Mol) werden Die Esterschmieröle gemäß vorliegender Erfindung
in einer Flasche geschüttelt, wobei das Reaktions- enthalten die Diarylhalogenalkylphosphate in kleigefäß
mit Wasser gekühlt wird, bis die Reaktion neren Mengen von vorzugsweise 2 bis 6 Gewichtsaufhört.
Nach Zugabe von Toluol (50 ecm) wird 15 prozent, berechnet auf die fertige Mischung.
4 Stunden unter Rückfluß erhitzt. Das abgekühlte Als Basisschmieröle werden vorzugsweise alipha-
4 Stunden unter Rückfluß erhitzt. Das abgekühlte Als Basisschmieröle werden vorzugsweise alipha-
Reaktionsgemisch wird mit 50 ecm leichtem Petro- tische Diester aus zweibasischen Carbonsäuren mit
leumspirit (Siedepunkt 100 bis 12O0C, Benzol 6 bis 20 Kohlenstoffatomen und einwertigen Alko-(50
ecm) und Wasser (50 ecm) verdünnt. Die ge- holen mit 1 bis 5 Kohlenstoffatomen eingesetzt, z. B.
bildete organische Schicht wird nacheinander mit 20 Ester von Adipinsäure, Pimelinsäure, Suberinsäure,
Wasser, verdünnter Natriumbicarbonatlösung und Azelainsäure und Sebazinsäure mit Laurylalkohol,
Wasser bis zur neutralen Reaktion gewaschen. Heptylalkohol, Octylalkohol und Nonylalkohol.
Wasser und organisches Lösungsmittel werden durch Die Esterschmieröle gemäß der Erfindung können
Wasser und organisches Lösungsmittel werden durch Die Esterschmieröle gemäß der Erfindung können
Destillation entfernt, und das Endprodukt wird unter auch weitere bekannte Zusatzstoffe enthalten, wie
vermindertem Druck destilliert. Beim Abkühlen 25 z. B. Verdickungsmittel, Antioxydationsmittel, die
kristallisiert Diphenyl^^-bis-ichlormethyty-S-chlor- Lackbildung verhindernde Mittel, schaumhindernde
propylphosphat als weißer Festkörper aus, der Mittel, Farbstoffe, korrosionshindernde Mittel, Mefolgende
Analysenwerte ergibt: tallentaktivatoren und gewünschtenfalls zusätzliche
JixtremdruckzusatzstofTe.
Säurewert 0 30 Geeignete Verdickungsmittel sind Polyalkylen-
Freies Chlorid 0 sulfone und ihre Mono- oder Diäther und Ester
Chlor (Gewichtsprozent) 24,8 sowie die Polymeren der Ester von Acrylsäure oder
1 -Alkylacrylsäure, wie in der britischen Patentschrift 703 445 beschrieben.
Herstellungsverfahren II 35 Eine besonders bevorzugte Klasse von Antioxy-
Dioctylphenyl-2,2-bis-(chlormethyl)- dationsmitteln bilden die Thiodiarylamine z. B.
3-chlorpropylphosphat Phenothmzm und 3,7-Dioctylphenothiazm. Es können
auch Gemische von Antioxydationsmitteln ver-
Destilliertes p-Octylphenol (116 g) (0,56 Mol) und wendet werden, insbesondere Gemische, die ein Thiodestilliertes
Phosphorylchlorid (43,2 g) (0,28 Mol) 4c diarylamin enthalten, z. B. ein Gemisch von Phenowerden
in einen Kolben eingebracht, der mit Thermo- thiazin und Phenyl-alpha-naphthylamin.
meter und Rührvorrichtung ausgerüstet ist. Die Geeignete schaumhindernde Mittel sind die PolyTemperatur des Reaktionsgemisches wird im Verlauf dimethylsiloxane mit einer Viskosität von 100 bis von 2 Stunden langsam auf 228 0C gesteigert und 100 000 sC bei 251C.
meter und Rührvorrichtung ausgerüstet ist. Die Geeignete schaumhindernde Mittel sind die PolyTemperatur des Reaktionsgemisches wird im Verlauf dimethylsiloxane mit einer Viskosität von 100 bis von 2 Stunden langsam auf 228 0C gesteigert und 100 000 sC bei 251C.
weitere 2 Stunden auf diesem Wert gehalten. Das 45 Beispiele von Antikorrosionsmitteln und Metallerhaltene
Produkt wird destilliert, und die bis 2400C entaktivatoren sind Benzotriazol, 5-Methylbenzobei
15 mm Hg siedende Fraktion wird analysiert triazol und Dicarbonsäuren mit niedrigem MoI-
und ergibt die Werte für Phosphorsäure-di-p-octyl- gewicht, wie Azelainsäure und Pimelinsäure,
phenylester-chlorid: Andere geeignete Extremdruckzusatzstoffe sind
phenylester-chlorid: Andere geeignete Extremdruckzusatzstoffe sind
50 z. B. die chlorierten Di- oder Polyphenyle und die
Chlor (Gewichtsprozent) 7,20 Triarylester von Phosphor- oder Phosphorothion-
säure.
27,6 g (0,06 Mol) Phosphorsäure-di-p-octylphenyl- Um die verbesserten Schmieröle gemäß der vor-
ester-chlorid, 13,8 g (0,07 Mol) 2,2-Bis-(chlormethyl)- liegenden Erfindung weiter zu erläutern, wurden
3-chlorpropanol, hergestellt nach dem Herstellungs- 55 Gemische der in Tabelle I angegebenen Zusammenverfahren
I, und Pyridin (6 g) (0,01 Mol) werden in Setzung (Beispiele 4 bis 7) hergestellt, geprüft und mit
einer Flasche unter Kühlung geschüttelt. Nach Zu- dem Basisöl (Beispiel 1) sowie Mischungen versatz
von Toluol (50 ecm) wird das Gemisch unter glichen, welche die gleichen Mengen eines bekannten
Rückfluß 4 Stunden erhitzt, wobei sich zwei getrennte Extremdruckzusatzstoffes enthielten (Beispiele 2
Phasen bilden. Das Produkt wird verdünnt mit 60 und 3).
100 ecm einer Mischung aus leichtem Petroleum- Diese Mischungen wurden auf ihr Belastungsverspirit
(Siedepunkt 100 bis 12O0C) und Benzol, und mögen geprüft in einem I. A. E.-Getriebekasten, wie
es wird dann mit Wasser, verdünnter Natriumbi- beschrieben in der Vorschrift 166/60 T des Institute
carbonatlösung und Wasser bis zur neutralen Re- of Petroleum, welcher bei einer öltemperatur von
aktion gewaschen, worauf man das Lösungsmittel 65 entweder 60 oder 1100C arbeitete. Die mittleren
abdestilliert. Der Rückstand, der freies Chlorid ent- Grenzbelastungen bei 2000 und 6000 U/min bei den
hält, wird mit Toluol verdünnt und diese Lösung mit beiden vorgenannten Temperaturen wurden beeinem
Ionenaustauscherharz aufgeschlämmt, das stimmt und in Tabelle II zusammengestellt.
Zusammensetzung nach Beispiel
3 I 4 I 5
Gewichtsprozent
6 j 7
Di-(isooctylazelat)
Chloriertes Diphenyl
Diphenyl-^-bis-chlormethyl-3-chlorpropylphosphat
Di-octylphenyl-^-bischlormethyl-3-chlorpropylphosphat
3,7-Dioctylphenothiazin ...
Phenyl-alpha-naphthylamin
Phenyl-alpha-naphthylamin
5-Methylbenzotriazol
Azelainsäure
Silicon/Antischaummittel ..
100,0
93,98 3,0
1,5 1,5
25 ppm 0,02 5 ppm
91,98 5,0
25 ppm 0,02 5 ppm 93,98
3,0
1,5
1,5
1,5
25 ppm
0,02
5 ppm
0,02
5 ppm
91,98
5,0
1,5
1,5
1,5
25 ppm 0,02
5 ppm
5 ppm
93,98
3,0 1,5 1,5
25 ppm 0,02 5 ppm
91,98
5,0 1,5 1,5
25 ppm 0,02 5 ppm
1 | 2 | 3 | Beispiel 4 |
5 | 6 | 7 | |
I. A. E.-Freßbelastung (kg) 2000 U/min 60 C |
25,4 25,4 15,42 10,43 76,65 |
37,65 33,57 18,14 14,51 103,87 |
43,09 36,29 20,41 16,33 116,12 |
47,63 38,56 22,68 20,41 129,28 |
58,97 43,09 24,95 22,68 149,69 |
43,09 38,56 20,41 18,14 120,20 |
49,90 40,82 24,93 20,41 136,06 |
110 C | |||||||
6000 U/min 60 C |
|||||||
110"C | |||||||
Summe der Freßbelastung (kg) .. |
Aus den Resultaten in Tabelle II ist deutlich zu ersehen, daß die Esterschmieröle gemäß der Erfindung,
welche die neuen Diarylhalogenalkylphosphate enthalten, überlegene Belastungseigenschaften
haben im Vergleich zu ähnlichen Mischungen, welche dieselben Mengen eines in der Praxis laufend verwendeten
Höchstdruckzusatzstoffes enthalten.
ROn
Claims (1)
- Patentanspruch:Esterschmieröl, enthaltend 0,1 bis 10 Gewichtsprozent eines Diarylhalogenalkylphosphates, dadurch gekennzeichnet, daß es ein Diarylhalogenalkylphosphat der allgemeinen FormelROP-O- CH2C(Y)3 Xworin R Arylreste sind, die gegebenenfalls durch eine oder mehrere Ci lo-Alkylreste substituiert sein können, X Sauerstoff oder Schwefel "bedeutet und Y gleiche oder verschiedene Reste von CH2Cl, CHCl2, CCk, CH3 und C2H5 sind, wobei jedoch nur ein CH3- oder C2Hs-ReSt vorhanden ist, enthält.In Betracht gezogene Druckschriften: Britische Patentschrift Nr. 763 967.809 617/882 11.68 O Bundesdruckerei Berlin
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB15953/63A GB1035984A (en) | 1963-04-23 | 1963-04-23 | Chlorine-containing phosphorus esters and lubricating oil compositions containing them |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1282828B true DE1282828B (de) | 1968-11-14 |
Family
ID=10068538
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DES90657A Pending DE1282828B (de) | 1963-04-23 | 1964-04-21 | Esterschmieroel |
Country Status (5)
Country | Link |
---|---|
US (1) | US3287266A (de) |
BE (1) | BE646836A (de) |
DE (1) | DE1282828B (de) |
GB (1) | GB1035984A (de) |
NL (1) | NL6404323A (de) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4159960A (en) * | 1977-05-02 | 1979-07-03 | Mobil Oil Corporation | Lubricant compositions |
US5279752A (en) * | 1989-02-22 | 1994-01-18 | Nippon Oil Co., Ltd. | Composition for lubricating oil |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB763967A (en) * | 1952-04-21 | 1956-12-19 | Monsanto Chemicals | Lubricating compositions |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2289509A (en) * | 1933-11-01 | 1942-07-14 | Atlantic Refining Co | Lubricant |
US2758091A (en) * | 1947-10-28 | 1956-08-07 | Shell Dev | Lubricating compositions |
US2656373A (en) * | 1950-04-14 | 1953-10-20 | Monsanto Chemicals | Process for producing mixed diaryl esters of ortho-phosphoric acid |
US2760937A (en) * | 1951-10-31 | 1956-08-28 | Exxon Research Engineering Co | Phosphorus-containing lubricant additives |
NL247300A (de) * | 1959-01-14 |
-
1963
- 1963-04-23 GB GB15953/63A patent/GB1035984A/en not_active Expired
-
1964
- 1964-03-30 US US355949A patent/US3287266A/en not_active Expired - Lifetime
- 1964-04-21 NL NL6404323A patent/NL6404323A/xx unknown
- 1964-04-21 DE DES90657A patent/DE1282828B/de active Pending
- 1964-04-21 BE BE646836D patent/BE646836A/xx unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB763967A (en) * | 1952-04-21 | 1956-12-19 | Monsanto Chemicals | Lubricating compositions |
Also Published As
Publication number | Publication date |
---|---|
GB1035984A (en) | 1966-07-13 |
BE646836A (de) | 1964-10-21 |
US3287266A (en) | 1966-11-22 |
NL6404323A (de) | 1964-10-26 |
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