EP0308445A1 - Verfahren zur herstellung eines ein anorganisches borderivat enthaltenden überbasischen additivs, danach erhaltene additive und diese enthaltende schmiermittel. - Google Patents
Verfahren zur herstellung eines ein anorganisches borderivat enthaltenden überbasischen additivs, danach erhaltene additive und diese enthaltende schmiermittel.Info
- Publication number
- EP0308445A1 EP0308445A1 EP88902504A EP88902504A EP0308445A1 EP 0308445 A1 EP0308445 A1 EP 0308445A1 EP 88902504 A EP88902504 A EP 88902504A EP 88902504 A EP88902504 A EP 88902504A EP 0308445 A1 EP0308445 A1 EP 0308445A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- weight
- boron
- reaction mixture
- additive
- esters
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 58
- 239000000654 additive Substances 0.000 title claims abstract description 36
- 150000001638 boron Chemical class 0.000 title claims abstract description 28
- 230000000996 additive effect Effects 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 239000000203 mixture Substances 0.000 title claims description 27
- 230000001050 lubricating effect Effects 0.000 title claims 2
- 239000003921 oil Substances 0.000 claims abstract description 28
- 239000011541 reaction mixture Substances 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 18
- 239000003599 detergent Substances 0.000 claims abstract description 17
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 14
- 239000003085 diluting agent Substances 0.000 claims abstract description 14
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 11
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 11
- 230000000694 effects Effects 0.000 claims abstract description 7
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract 2
- 150000001340 alkali metals Chemical class 0.000 claims abstract 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 46
- 229910052796 boron Inorganic materials 0.000 claims description 43
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 26
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 17
- 239000004327 boric acid Substances 0.000 claims description 17
- 239000001569 carbon dioxide Substances 0.000 claims description 13
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- -1 aliphatic alcohols Chemical class 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000002989 phenols Chemical class 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 8
- 239000006185 dispersion Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 150000002334 glycols Chemical class 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 150000001639 boron compounds Chemical class 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000007865 diluting Methods 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 229920005862 polyol Polymers 0.000 claims description 3
- 150000003077 polyols Chemical class 0.000 claims description 3
- 150000003870 salicylic acids Chemical class 0.000 claims description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 150000001543 aryl boronic acids Chemical class 0.000 claims description 2
- 150000001896 cresols Chemical class 0.000 claims description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 2
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- 239000010695 polyglycol Substances 0.000 claims description 2
- 229920000151 polyglycol Polymers 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 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 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000005619 boric acid group Chemical group 0.000 claims 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims 1
- 150000004679 hydroxides Chemical class 0.000 claims 1
- 239000006193 liquid solution Substances 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000010689 synthetic lubricating oil Substances 0.000 claims 1
- 239000010687 lubricating oil Substances 0.000 abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 239000000047 product Substances 0.000 description 38
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 16
- 239000008096 xylene Substances 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 229910021538 borax Inorganic materials 0.000 description 7
- 235000010339 sodium tetraborate Nutrition 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- YFMUPHJGWWRKLX-UHFFFAOYSA-N boric acid;propane-1,2-diol Chemical compound OB(O)O.CC(O)CO YFMUPHJGWWRKLX-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 239000004328 sodium tetraborate Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 5
- 239000011149 active material Substances 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical group CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 239000007866 anti-wear additive Substances 0.000 description 4
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 4
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 4
- 239000000920 calcium hydroxide Substances 0.000 description 4
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 4
- 235000011116 calcium hydroxide Nutrition 0.000 description 4
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 229940092714 benzenesulfonic acid Drugs 0.000 description 3
- 238000001246 colloidal dispersion Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- QUKZABJWJDFCMS-UHFFFAOYSA-N OB(O)O.OB(O)O.OB(O)O.OB(O)O.N.N.O.O.O.O Chemical compound OB(O)O.OB(O)O.OB(O)O.OB(O)O.N.N.O.O.O.O QUKZABJWJDFCMS-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- 235000012501 ammonium carbonate Nutrition 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 125000005587 carbonate group Chemical group 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- AUTNMGCKBXKHNV-UHFFFAOYSA-P diazanium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [NH4+].[NH4+].O1B([O-])OB2OB([O-])OB1O2 AUTNMGCKBXKHNV-UHFFFAOYSA-P 0.000 description 2
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- JKTAIYGNOFSMCE-UHFFFAOYSA-N 2,3-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1CCCCCCCCC JKTAIYGNOFSMCE-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- WECIKJKLCDCIMY-UHFFFAOYSA-N 2-chloro-n-(2-cyanoethyl)acetamide Chemical compound ClCC(=O)NCCC#N WECIKJKLCDCIMY-UHFFFAOYSA-N 0.000 description 1
- GDTSJMKGXGJFGQ-UHFFFAOYSA-N 3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound O1B([O-])OB2OB([O-])OB1O2 GDTSJMKGXGJFGQ-UHFFFAOYSA-N 0.000 description 1
- QGBLCIBATKETJC-UHFFFAOYSA-N 3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane;manganese(2+) Chemical compound [Mn+2].O1B([O-])OB2OB([O-])OB1O2 QGBLCIBATKETJC-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000005069 Extreme pressure additive Substances 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical group CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CVIYUGFFLDJRAO-UHFFFAOYSA-N OB(O)O.OB(O)O.OB(O)O.OB(O)O.N.N.N Chemical compound OB(O)O.OB(O)O.OB(O)O.OB(O)O.N.N.N CVIYUGFFLDJRAO-UHFFFAOYSA-N 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- GMBCWYJNYUIBKS-UHFFFAOYSA-N [B]=O.OB(O)O Chemical compound [B]=O.OB(O)O GMBCWYJNYUIBKS-UHFFFAOYSA-N 0.000 description 1
- FZQSLXQPHPOTHG-UHFFFAOYSA-N [K+].[K+].O1B([O-])OB2OB([O-])OB1O2 Chemical compound [K+].[K+].O1B([O-])OB2OB([O-])OB1O2 FZQSLXQPHPOTHG-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
- QBLDFAIABQKINO-UHFFFAOYSA-N barium borate Chemical compound [Ba+2].[O-]B=O.[O-]B=O QBLDFAIABQKINO-UHFFFAOYSA-N 0.000 description 1
- 229910052810 boron oxide Inorganic materials 0.000 description 1
- 125000005620 boronic acid group Chemical class 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 210000004534 cecum Anatomy 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- PSHMSSXLYVAENJ-UHFFFAOYSA-N dilithium;[oxido(oxoboranyloxy)boranyl]oxy-oxoboranyloxyborinate Chemical compound [Li+].[Li+].O=BOB([O-])OB([O-])OB=O PSHMSSXLYVAENJ-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Chemical group CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- KRHIGIYZRJWEGL-UHFFFAOYSA-N dodecapotassium;tetraborate Chemical compound [K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-] KRHIGIYZRJWEGL-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229940047135 glycate Drugs 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- ZPPSOOVFTBGHBI-UHFFFAOYSA-N lead(2+);oxido(oxo)borane Chemical compound [Pb+2].[O-]B=O.[O-]B=O ZPPSOOVFTBGHBI-UHFFFAOYSA-N 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000010691 naphtenic oil Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical group CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Chemical group CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000010690 paraffinic oil Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- JAKYJVJWXKRTSJ-UHFFFAOYSA-N sodium;oxido(oxo)borane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B=O JAKYJVJWXKRTSJ-UHFFFAOYSA-N 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical group ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
-
- 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
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
- C10M159/22—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing phenol radicals
-
- 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
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
- C10M159/24—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing sulfonic radicals
-
- 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
- C10M2207/028—Overbased 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/26—Overbased carboxylic acid salts
-
- 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
- C10M2207/26—Overbased carboxylic acid salts
- C10M2207/262—Overbased carboxylic acid salts derived from hydroxy substituted aromatic acids, e.g. salicylates
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/28—Amides; Imides
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/046—Overbasedsulfonic acid salts
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/089—Overbased salts
Definitions
- This invention relates to a process for preparing an over-alkalized additive for lubricating oils containing a boron derivative, the additive thus obtained and a lubricant composition containing said additive.
- additives improving their properties.
- these additives are detergents, dispersants, anti-wear and extreme pressure additives and additives providing a basic reserve.
- the detergent and dispersing properties of a lubricant correspond to its ability to maintain impurities and burnt i in suspension in the hot parts of the engine by its detergency effect but also in the cold parts by its dispersing effect. The fixing of these particles in the form of varnish or lacquers is thus avoided.
- the role of basic reserve additives consists in combating the acidity caused in engines by the combustion of organic sulfur derivatives contained in fuels and by the oxidation of the components of lubricating oils.
- Anti-wear additives act by forming a solid or plastic thin film which separates the friction surfaces and prevents wear of the different parts of the engine.
- the detergent and dispersant properties as well as the basicity reserve are generally provided by overbased additives. These are alkali or alkaline earth metal carbonates in a detergent solution of the al yl sulfonate, phenate or salicylate type.
- Antiwear additives are generally sulfur and / or phosphorus compounds, the most commonly used being the Zn dialkyldithiophosphates.
- Boron derivatives form another class of antiwear additives.
- the boron mineral compounds provide an antiwear and extreme pressure function (US patents 3,907,691 and 4,10081) while the organic compounds provide antiwear and antifriction properties rather (American patents 4,549,775 and 4,599,183).
- US Patent 3,907,691 provides for the format of a complex by heating the intermediate product fo by reaction of boric acid with the overbased sulfonate.
- US Patent 4,539,126 claims the preparation of complexes by reaction of boric acid with overbased alkylsalicylate.
- the alkaline value (VA) is fictitiously equivalent to the number of milligrams of KOH per gram of additive surba titrated by a strong acid. It is determined by direct potentiometric dosa according to standard ASTM D-2896.
- the process for the preparation of overbased additi with antiwear effect consists in carbonating a reaction mixture composed of at least detergent, of a metal, alkali or alkaline earth derivative of at least one nitrogenous and / or oxygenated promoter in a diluting oil and a hydrocarbon solvent characterized in that it operates in the presence of at least one boron derivative.
- Inorganic or bi organic derivatives of boron can be used.
- the oxides and anhydrides of boron as well as boric ac and its salts.
- esters boric acid and the liberated or esterified alkyl and arylboronic acids are particularly useful.
- Esters are formed with aliphatic, cyclic or phenol alcohols.
- the aliphatic alcohols are generally linear or branched in C. to C__ and preferably in C.
- glycols having the two hydroxyl groups in positions 1-2, 1-3, or 1-4, such as glycol, propylene glycol or neopentyl glycol as well as polyglycols such as diethylene glycol, dipropyl glycol or tripropylene glycol.
- Polyols such as glycerol, trimethylolpropane or pentaerythritol are also suitable.
- alkoxyalkanols and preferably the alkoxyalkanols corresponds to the general formula RO (CHR .. (CH_) JOL H or R is C 1 to C alkyl group, R. hydrogen or an alk group C- to C. ,, a is between 1 and 3 and b corresponds or 2.
- alkoxyalkanols examples include methoxyethanol, 1 • ethoxyethanol or ETHYL-CELLOSOLVE and BUTYL-CELLOSOLVE.
- Alcohols the molecule of which contains several amino functions, are also suitable.
- alkanolamines such as diethanolamine or triethanola ine and oxyalkylated alkylmono polyamines.
- the oxyalkylated alkyl monoamines preferably correspond to the formula R_NH Z, or R is hydrogen or alkyl, C. to C__ preferably C.
- Q to C-, g corresponds to the group -CHR, -CH? -OH, R., being a C 1 to C 4 alkyl group or an aromatic ring, c may be 0 or and c + d is equal to 2.
- the oxyalkylated alkyl polyamines preferably correspond to the formula R_NZ n - (CH_) -NZ_Z, or Z., Z_ and identical or different correspond to hydrogen and at least one of the three corresponds to Z defined above, R_ has the same meaning as above .
- cyclic alcohols cyclopentanol, cyclohexanol and their mono polyalkylated derivatives can be mentioned on the ring.
- phenols phenol itself and its substituted derivatives, such as cresols, are most commonly used.
- the boric acid esters can be prepared by any known method, in particular by reacting boron trichloride with alcohols and phenols. In the event of the esterification of boric acid by the polyols, the water formed must be removed by azeotropic entrainment.
- boron derivatives are used alone or as a mixture.
- the boron derivatives can be added to the reaction mixture in pulverulent form, optionally previously dispersed in an oil, in the form of an aqueous solution or in liquid form.
- the detergents commonly used in overbased additives are salts of sulfonic acids, salicyclic acids or phenols
- R 4 is a radical hydrocarbon from 12 to 100 carbon atoms, n is between i and 6 and m is between 1 and 5.
- the sulfonic acids are of petroleum or synthetic origin.
- the average molecular weight of petroleum sulfonates is generally greater than 320. They are obtained by sulfonation of petroleum distillates. Synthetic sulfonic acids are particularly useful in the context of the invention. They may be products obtained by sulfonation of olefins with a carbon number greater than or equal to 12 or alternatively alkylarylsulfonic acids.
- Alkylarylsulfonic acids have one or more alkyl chains on an aromatic ring, generally a benzenic ring.
- the alkyl chains must contain a minimum of 8 carbon atoms. Their structure is linear or branched.
- Oil-soluble salicylic acids substituted on the aromatic ring by a chain have at least 10 and in general 16 to 18 carbon atoms.
- the phenols soluble in organic medium which are particularly advantageous in the context of the invention are phenols substituted by one or more linear or branched alkyl chai comprising at least 8 carbon atoms.
- the most common commercial products are for example nonylphenol, dinonylphenol, dodecylphenol and their mixtures.
- Phenols are used in the form of alkali or alkaline earth metal salts. They are particularly appreciated after having undergone sulfurization by reaction with the flower of sulfur or enc with sulfur chloride.
- Sulfonic salicylic acids or phenols can be used in mela with dispersants derived from alkenylsuccinic acids chain greater than or equal to 12 carbon atoms or b with carboxylic acids having at least 8 carbon atoms.
- the alkali or alkaline earth metal derivative is generally an oxide, hydroxide or alcoholate of such a metal
- the oxygenated promoters are mainly aliphatic alcohols, generally C 1 to C 2, most often methanol, ethanol, butanol or glycols. Ethers such as dioxolane or dialkoxymethanes are also used.
- the alcohols can be used alone when mixed with water.
- the nitrogen promoters are among others ammonia, ethylenediamine, ethanolamines, ammonium chloride or ammonium carbonate.
- the role of the diluent oil is to allow easy handling at room temperature.
- paraffinic oils such as 7,100 or 150 Neutral or naphtenic oils, type 100 Pa solvent.
- Hydrocarbon solvents have an aliphatic structure, such as heptane, isooctane, nonane or an aromatic structure, such as toluene or xylene. These solvents can be used as a mixture. It is particularly advantageous to use solvents which give azeotropes with water, such as alcohols, glycols or alkoxyalkanols
- a double jacket reactor is generally used, provided with a vigorous stirring system, a temperature regulator, a condenser, a system allowing a vacuum to be produced. o a slight overpressure, a gas diffuser and a solvent recovery system.
- the boron derivatives are used in the form of an oil dispersion, this dispersion is added to the reaction mixture before the introduction of carbon dioxide.
- the boron derivatives used in dispersion are boric acid and its salts.
- the boron derivatives used in powder form or in the form of an aqueous solution if their solubility is sufficient, are boron oxide boric acid and its salts.
- the boron derivatives used in liquid form are certain boric esters and alkyl or ary boronic acids.
- the pulverulent, liquid compounds or the aqueous solutions are introduced before carbonation o during carbonation a few minutes after starting the starting of the reaction.
- the reaction mixture is subjected to vigorous stirring until the introduction of 50 to 350 parts by inch of carbon dioxide by bubbling into the reaction millet.
- the duration of carbonation generally varies from 20 minutes to 4 hours at constant flow.
- the mixture is maintained at a temperature varying from 20 to 80 ° C and preferably from 35 to 70 ° C.
- reaction mixture containing the boron derivative may be advantageous to bring the reaction mixture containing the boron derivative to reflux, for a period of 30 minutes to 2 hours before carbonation.
- Solvents can be removed in just one step, but generally there are two steps.
- the solvents, apart from the hydrocarbon diluent, are removed by heating and then the solid residues by centrifugation or filtrate before the removal of the hydrocarbon solvent.
- the overbased additives obtained by the process according to the invention have alkaline values (VA), measured according to standard ASTM D-2896, generally greater than 200 KOH / g. VAs greater than 300 and even 500 can be obtained.
- VA alkaline values
- reaction mixture free of bo derivative is brought to reflux for at least half an hour. After cooling, the boron derivative is added. The introduction of carbon dioxide and the subsequent treatment proceed as before.
- the overbased phenates obtained have d alkaline values (VA) generally greater than 150 KOH / g. VAs greater than 250 even 320 can be obtained.
- the amount of boron incorporated can vary between 0 and 10% by weight and preferably 0.25 to 5%. This amount is sufficient to provide antiwear properties to lubricating oils.
- the antiwear properties are measured by mechanical tests commonly used, such as the method of the 4 wear balls (NF-E 48-617) and 4 extreme pressure balls (ASTM D 2783-69T or NF E 48-617) and the FALEX tests ( ASTM D 32-33).
- the additives according to the invention have a limpid aspect and keep a homogeneous consistency over time. They have viscosities sufficiently low to allow easy handling and are compatible with the other additives usually used in lubricating oils.
- the overbased additives are added to lubricating oils of natural or synthetic origin at a concentration of between 0.5 and 40% by weight and preferably between 1 and 30% by weight.
- Example 3 The procedure of Example 1 is repeated except that 1 'adds 5 g of sodium metaborate tetrahydrate to the reaction medium before the 10th minute of carbonation. collects a product much more fluid than the previous VA 425, stable in oil and whose boron content is about 0.37% by weight EXAMPLE 3
- Example 4 The experiment described in Example 1 is repeated, except that 2g of powdered sodium tetraborate are added to the reaction medium before the 10th minute of carbonation. A product of VA 403 mg KOH / g whose boron content is 0.45% by weight is collected. EXAMPLE 4
- Example 6 A simple mixture of 13 g of overbased sulfonate in Example 1 is prepared with 3 g of the dispersion of sodium tetraborate in Example 4. A product of VA 35 containing 0.36% by weight of boron, with a cloudy appearance, is obtained. Examination with an electron microscope of the product shows the presence of calcium carbonate globules of 60 A diameter and sodium borate particles of 0.6 ⁇ m diameter. EXAMPLE 6
- Example 3 The procedure described in Example 3 is repeated, with the difference that 4 g of 200N diluent oil are introduced instead of 22.5 g. 20.5 g of the sodium tetraborate dispersion of Example 4 are added before the carbonation begins. A product with a clear appearance, of 369 mg KOH / g at 0.46% by weight of boron, is then collected. IL "examination with an electron microscope reveals the presence of globules of approximately 60 A in diameter only. The analysis of globules in loss of energy gives a spectrum where 1'O notices a peak characteristic of the presence of boron.
- Example 6 according to the invention allows effective incorporation of boron into the globules of the colloidal dispersion.
- Example 3 The procedure of Example 3 is repeated, except that 30 grams of calcium oxide, 10.2 ml of water are introduced and the product is carbonated for 75 minutes at a rate of 103 ml / minute. Before the 15th minute of carbonation o add 9.52g of potassium tetraborate powder. O collects a clear product of VA 310 mg KOH / g and contains 0.86% by weight of boron.
- Example 9 The procedure of Example 7 is repeated, but the boron compound is boric acid. 8.98 g of boric acid and powder are added to the 10th minute of carbonation. We then obtain a product of VA 411 mg KOH / g and of very viscous consistency. It contains 1.23% by weight of boron. EXAMPLE 9
- Example 10 The procedure of Example 7 is repeated after adding only 4.5 ml of methanol to the reaction medium. O obtains a clear, very fluid product of VA 298 mg KOH / and containing 1.3% by weight of boron.
- EXAMPLE 10 The procedure of Example 7 is repeated after adding only 4.5 ml of methanol to the reaction medium. O obtains a clear, very fluid product of VA 298 mg KOH / and containing 1.3% by weight of boron.
- Example 8 The procedure of Example 8 is repeated, but the diluent oil is replaced with 28.5 g of a dispersion of boric acid in the oil at around 5% by weight of boron. This dispersion is introduced into the mixture before the start of carbonation. A clear product of VA 303 KOH / g and 1.2% by weight of boron is obtained.
- Example 8 The procedure of Example 8 is repeated, but 11.2 of powdered boron trioxide are added.
- Example 7 The procedure of Example 7 is repeated but 1 of trimethylborate is added to the 10th minute of carbonation. then obtains a viscous product of VA 437 mg KOH / g e 1.2% by weight of boron.
- Example 14 The procedure of Example 1 is repeated except that 9.53 g of powdered diammonium tetraborate are added after minutes of carbonation. A relatively fluid limp product of VA 438 mg KOH / g and containing 1, weight of boron is obtained.
- EXAMPLE 14 The procedure of Example 1 is repeated except that 9.53 g of powdered diammonium tetraborate are added after minutes of carbonation. A relatively fluid limp product of VA 438 mg KOH / g and containing 1, weight of boron is obtained.
- Example 10 The procedure of Example 10 is repeated but the same conditions are added 19.06 g of diammonium tetraborate.
- a product of VA 437 mg KOH / g is collected which contains 1, weight of boron.
- Example 10 The procedure of Example 10 is repeated, but the carbonate additive for 23 minutes at 148 ml / minute.
- reaction mixture is carbonated as soon as the temperature has dropped to 49 ° C.
- Example 1 The procedure of Example 1 is repeated except that the o uses instead of the C_ 4 -benzene sulfonic acid, 23 of an 80/20 mixture by mole of C_ 4 acid ⁇ benzene sulfonic acid by weight. molar 520 to 70% of active material and C_ carboxylic acid obtained by hydroformylation of olefin (CK9 acid distributed by the company NORSOLOR). 30.7 g of slaked lime at 97% purity are added.
- Carbonation is carried out for 25 minutes at a flow rate of 210ml / minute.
- a solution of propylene glycol borate in xylene is prepared by heating to 50 ° C. with stirring of a mixture of 46.4 g of propylene glycol, 41 g of boric acid and 300 m of xylene. The water formed is removed by azeotropic distillatio. 314 g of a 2.6% boron solution are obtained Into the reactor described above, from Example 1, 34.6 g of the propylene glycol borate solution, 16.61 g of C., ⁇ -alkylbenzenesulfonic acid 96% of active material and of molecular weight 430, 24, d are introduced. diluent oil, 112ml of xylene, 7ml of methanol and 23ml of slaked lime at 99% purity.
- the mixture is carbonated for 26 minutes at 42 at a flow rate of 230ml / minute.
- the mixture is carbonate at a flow rate of 156 ml / minute for 26 minutes at a temperature of 42 ° C.
- the limpi product collected has a VA of 351 and contains 0.36% of boron.
- the mixture is brought to reflux for 3 hours then it is carbonated for 50 minutes a flow rate of approximately 90 ml / minute at a temperature of 53 ° C.
- the solvents and the hydrocarbon diluent are removed by heating to 100 ° under reduced pressure.
- Example 19 The procedure of Example 19 is repeated, except that 6.75 g of powdered diammoni tetraborate are added to the reaction medium after 10 minutes of carbonation. A relatively fluid product is obtained, of VA 267 mg KOH and containing 1.43% of boron.
- the procedure is as in the previous example but by introducing 40.6 g of tributylborate and 28 ml of methanol before carbonation.
- the product has a VA of 265 and contains 1.8% boron.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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FR8703646 | 1987-03-17 | ||
FR8703646A FR2612526B1 (fr) | 1987-03-17 | 1987-03-17 | Procede de preparation d'un additif suralcanise renfermant un derive du bore, l'additif ainsi obtenue et compositions lubrifiantes renfermant ledit additif |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
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EP90104404A Division EP0383359B1 (de) | 1987-03-17 | 1988-03-16 | Verfahren zur Herstellung eines, ein anorganisches Borderivat enthaltenden, }berbasischen Additivs, so erhaltenes Additiv und Schmiermittel, die dieses Additiv enthalten. |
EP90104404.0 Division-Into | 1990-03-08 |
Publications (2)
Publication Number | Publication Date |
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EP0308445A1 true EP0308445A1 (de) | 1989-03-29 |
EP0308445B1 EP0308445B1 (de) | 1991-08-28 |
Family
ID=9349073
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP88902504A Expired - Lifetime EP0308445B1 (de) | 1987-03-17 | 1988-03-16 | Verfahren zur herstellung eines ein anorganisches borderivat enthaltenden überbasischen additivs, danach erhaltene additive und diese enthaltende schmiermittel |
Country Status (6)
Country | Link |
---|---|
US (1) | US5098587A (de) |
EP (1) | EP0308445B1 (de) |
JP (1) | JPH01502759A (de) |
DE (1) | DE3864483D1 (de) |
FR (1) | FR2612526B1 (de) |
WO (1) | WO1988007073A1 (de) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2653780A1 (fr) * | 1989-10-26 | 1991-05-03 | Elf Aquitaine | Additif surbase pour huiles lubrifiantes renfermant un derive du cuivre ou un derive du cuivre et du bore, son procede de preparation et compositions renfermant ledit additif . |
JP2814131B2 (ja) * | 1990-03-14 | 1998-10-22 | 日本石油株式会社 | アルコール系燃料用エンジン油組成物 |
JP2617807B2 (ja) * | 1990-03-16 | 1997-06-04 | 日本石油株式会社 | エンジン油組成物 |
FR2698019B1 (fr) * | 1992-11-18 | 1995-02-24 | Inst Francais Du Petrole | Produits colloïdaux contenant du calcium et/ou du magnésium, ainsi que du bore et/ou du phosphore et/ou du soufre, leur préparation et leur utilisation comme additifs pour lubrifiants. |
US6451745B1 (en) | 1999-05-19 | 2002-09-17 | The Lubrizol Corporation | High boron formulations for fluids continuously variable transmissions |
US6368969B1 (en) | 2000-06-30 | 2002-04-09 | International Business Machines Corporation | Chemical-mechanical polishing methods |
US7479568B2 (en) * | 2005-11-30 | 2009-01-20 | Chevron Oronite Company Llc | Process for making alkaline earth metal borated sulfonates |
US7981846B2 (en) * | 2005-11-30 | 2011-07-19 | Chevron Oronite Company Llc | Lubricating oil composition with improved emission compatibility |
US7868209B2 (en) * | 2007-05-30 | 2011-01-11 | Chevron Oronite Sa | Process for making borated alkaline earth metal toluene sulfonates |
US20080300154A1 (en) * | 2007-05-30 | 2008-12-04 | Chevron Oronite Company Llc | Lubricating oil with enhanced protection against wear and corrosion |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB789820A (en) * | 1955-03-25 | 1958-01-29 | Continental Oil Co | Improvements in or relating to dispersions of inorganic metal compounds in lubricating oil and methods of making the same |
US3480548A (en) * | 1967-06-21 | 1969-11-25 | Texaco Inc | Alkaline earth metal polyborate carbonate overbased alkaline earth metal sulfonate lube oil composition |
US3829381A (en) * | 1970-02-02 | 1974-08-13 | Lubrizol Corp | Boron-and calcium-containing compositions and process |
US3679584A (en) * | 1970-06-01 | 1972-07-25 | Texaco Inc | Overbased alkaline earth metal sulfonate lube oil composition manufacture |
CA966148A (en) * | 1971-05-07 | 1975-04-15 | Mack W. Hunt | Preparation of oil-soluble metal sulfonates |
US3929650A (en) * | 1974-03-22 | 1975-12-30 | Chevron Res | Extreme pressure agent and its preparation |
FR2271281B2 (de) * | 1974-03-29 | 1977-01-21 | Inst Francais Du Petrole | |
US3907691A (en) * | 1974-07-15 | 1975-09-23 | Chevron Res | Extreme-pressure mixed metal borate lubricant |
US4560489A (en) * | 1983-09-14 | 1985-12-24 | Witco Chemical Corporation | High performance calcium borate modified overbased calcium sulfonate complex greases |
GB2149810B (en) * | 1983-11-15 | 1987-04-08 | Shell Int Research | Borated basic metal salt and oil composition containing it |
JPS61204298A (ja) * | 1985-03-08 | 1986-09-10 | Nippon Oil Co Ltd | アルカリ土類金属ホウ酸塩分散体の製造方法 |
US4601837A (en) * | 1985-09-06 | 1986-07-22 | Amoco Corporation | Process for the preparation of overbased, molybdenum-alkaline earth metal sulfonate dispersions |
US4659488A (en) * | 1985-09-18 | 1987-04-21 | The Lubrizol Corporation | Metal working using lubricants containing basic alkaline earth metal salts |
FR2588268B1 (fr) * | 1985-10-03 | 1988-02-05 | Elf France | Procede de synthese d'additifs surbases par carbonatation sous pression constante d'anhydride carbonique |
US4744920A (en) * | 1986-12-22 | 1988-05-17 | The Lubrizol Corporation | Borated overbased material |
US4965004A (en) * | 1989-04-21 | 1990-10-23 | Texaco Inc. | Process for a borated detergent additive |
US4965003A (en) * | 1989-04-21 | 1990-10-23 | Texaco Inc. | Borated detergent additive by an improved process |
-
1987
- 1987-03-17 FR FR8703646A patent/FR2612526B1/fr not_active Expired - Fee Related
-
1988
- 1988-03-16 WO PCT/FR1988/000137 patent/WO1988007073A1/fr active IP Right Grant
- 1988-03-16 EP EP88902504A patent/EP0308445B1/de not_active Expired - Lifetime
- 1988-03-16 JP JP63502573A patent/JPH01502759A/ja active Pending
- 1988-03-16 DE DE8888902504T patent/DE3864483D1/de not_active Expired - Fee Related
-
1990
- 1990-06-29 US US07/546,670 patent/US5098587A/en not_active Expired - Fee Related
Non-Patent Citations (1)
Title |
---|
See references of WO8807073A1 * |
Also Published As
Publication number | Publication date |
---|---|
DE3864483D1 (de) | 1991-10-02 |
WO1988007073A1 (fr) | 1988-09-22 |
US5098587A (en) | 1992-03-24 |
FR2612526A1 (fr) | 1988-09-23 |
EP0308445B1 (de) | 1991-08-28 |
JPH01502759A (ja) | 1989-09-21 |
FR2612526B1 (fr) | 1990-02-02 |
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