CA1122962A - Procede de preparation de detergents-dispersants de haute alcalinite pour huiles lubrifiantes - Google Patents
Procede de preparation de detergents-dispersants de haute alcalinite pour huiles lubrifiantesInfo
- Publication number
- CA1122962A CA1122962A CA321,059A CA321059A CA1122962A CA 1122962 A CA1122962 A CA 1122962A CA 321059 A CA321059 A CA 321059A CA 1122962 A CA1122962 A CA 1122962A
- Authority
- CA
- Canada
- Prior art keywords
- parts
- mixture
- alkylphenol
- weight
- alkylbenzene sulfonate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 36
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 239000000654 additive Substances 0.000 title claims description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 101
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 60
- -1 alkylbenzene sulfonate Chemical class 0.000 claims abstract description 45
- 239000000203 mixture Substances 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 35
- 239000011575 calcium Substances 0.000 claims description 31
- 239000003921 oil Substances 0.000 claims description 30
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 28
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 20
- 239000002585 base Substances 0.000 claims description 19
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 15
- 238000005987 sulfurization reaction Methods 0.000 claims description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- 239000011593 sulfur Substances 0.000 claims description 14
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 13
- 239000000047 product Substances 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 10
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 9
- 239000011777 magnesium Substances 0.000 claims description 9
- 229910052749 magnesium Inorganic materials 0.000 claims description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- 239000001569 carbon dioxide Substances 0.000 claims description 5
- 238000010790 dilution Methods 0.000 claims description 5
- 239000012895 dilution Substances 0.000 claims description 5
- 150000001336 alkenes Chemical class 0.000 claims description 4
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- 229910052788 barium Inorganic materials 0.000 claims description 3
- 150000004679 hydroxides Chemical class 0.000 claims description 3
- JOONSONEBWTBLT-UHFFFAOYSA-N 2-tetradecylphenol Chemical class CCCCCCCCCCCCCCC1=CC=CC=C1O JOONSONEBWTBLT-UHFFFAOYSA-N 0.000 claims description 2
- 208000005156 Dehydration Diseases 0.000 claims description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 235000021178 picnic Nutrition 0.000 claims description 2
- 238000006277 sulfonation reaction Methods 0.000 claims description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910001863 barium hydroxide Inorganic materials 0.000 claims 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims 1
- 159000000007 calcium salts Chemical class 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims 1
- 239000000347 magnesium hydroxide Substances 0.000 claims 1
- 239000003599 detergent Substances 0.000 abstract description 5
- 239000000243 solution Substances 0.000 description 33
- 229910052791 calcium Inorganic materials 0.000 description 24
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 21
- 235000011941 Tilia x europaea Nutrition 0.000 description 21
- 239000004571 lime Substances 0.000 description 21
- 239000013049 sediment Substances 0.000 description 13
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000283986 Lepus Species 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 2
- 239000010705 motor oil Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004435 Oxo alcohol Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000010710 diesel engine oil Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000010690 paraffinic oil 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000009656 pre-carbonization Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 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
- C10M159/24—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing sulfonic radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Detergent Compositions (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7803464A FR2416942A1 (fr) | 1978-02-08 | 1978-02-08 | Procede de preparation de detergents-dispersants de haute alcalinite pour huiles lubrifiantes |
| FR78.03464 | 1978-02-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1122962A true CA1122962A (fr) | 1982-05-04 |
Family
ID=9204324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA321,059A Expired CA1122962A (fr) | 1978-02-08 | 1979-02-07 | Procede de preparation de detergents-dispersants de haute alcalinite pour huiles lubrifiantes |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4251379A (en, 2012) |
| EP (1) | EP0003694B1 (en, 2012) |
| JP (1) | JPS6018714B2 (en, 2012) |
| AT (1) | AT369354B (en, 2012) |
| BR (1) | BR7900759A (en, 2012) |
| CA (1) | CA1122962A (en, 2012) |
| DE (1) | DE2962163D1 (en, 2012) |
| ES (1) | ES477477A1 (en, 2012) |
| FR (1) | FR2416942A1 (en, 2012) |
| IT (1) | IT1114549B (en, 2012) |
| MX (1) | MX5771E (en, 2012) |
| ZA (1) | ZA79532B (en, 2012) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2429831A2 (fr) * | 1978-06-26 | 1980-01-25 | Orogil | Nouveau procede de preparation de detergents-dispersants de haute alcalinite pour huiles lubrifiantes |
| FR2429833A1 (fr) * | 1978-06-26 | 1980-01-25 | Orogil | Procede de preparation de detergents-dispersants metalliques suralcalinises pour huiles lubrifiantes |
| FR2529226B1 (fr) * | 1982-06-24 | 1987-01-16 | Orogil | Procede de preparation d'alkylphenates sulfurises de metaux alcalino-terreux utilisables comme additifs pour huiles lubrifiantes |
| FR2529225B1 (fr) * | 1982-06-24 | 1986-04-25 | Orogil | Nouvel additif detergent-dispersant metallique de haute alcalinite pour huiles lubrifiantes |
| FR2529224B1 (fr) * | 1982-06-24 | 1986-02-07 | Orogil | Nouvel additif detergent-dispersant suralcalinise pour huiles lubrifiantes |
| FR2549080B1 (fr) * | 1983-07-11 | 1986-04-04 | Orogil | Procede de preparation d'additifs detergents-dispersants de tres haute alcalinite a base de calcium et additifs detergents-dispersants pour huiles lubrifiantes ainsi obtenus |
| US4543194A (en) * | 1984-03-28 | 1985-09-24 | Phillips Petroleum Company | Precarbonation in overbasing calcium petroleum sulfonates |
| US4664246A (en) * | 1984-03-28 | 1987-05-12 | Phillips Petroleum Company | Apparatus for producing and recovering overbased petroleum sulfonate |
| FR2584414B1 (fr) * | 1985-07-08 | 1987-10-30 | Orogil | Nouveaux additifs detergents-dispersants sulfones et sulfurises pour huiles lubrifiantes |
| GB8723909D0 (en) * | 1987-10-12 | 1987-11-18 | Exxon Chemical Patents Inc | Lubricant oil additive |
| US5169545A (en) * | 1991-08-30 | 1992-12-08 | Mobil Oil Corporation | Metal phenate sulfides |
| US5330664A (en) * | 1992-09-02 | 1994-07-19 | Chevron Research And Technology Company | Neutral and low overbased alkylphenoxy sulfonate additive compositions derived from alkylphenols prepared by reacting an olefin or an alcohol with phenol in the presence of an acidic alkylation catalyst |
| US5330663A (en) * | 1992-09-02 | 1994-07-19 | Chevron Research And Technology Company | Neutral and low overbased alkylphenoxy sulfonate additive compositions |
| US5320762A (en) * | 1993-03-12 | 1994-06-14 | Chevron Research And Technology Company | Low viscosity Group II metal overbased sulfurized C12 to C22 alkylphenate compositions |
| US5320763A (en) * | 1993-03-12 | 1994-06-14 | Chevron Research And Technology Company | Low viscosity group II metal overbased sulfurized C10 to C16 alkylphenate compositions |
| US5318710A (en) * | 1993-03-12 | 1994-06-07 | Chevron Research And Technology Company | Low viscosity Group II metal overbased sulfurized C16 to C22 alkylphenate compositions |
| US7405185B2 (en) * | 2003-09-26 | 2008-07-29 | Chevron Oronite Company Llc | Process for making Group II metal overbased sulfurized alkylphenols |
| US8198225B2 (en) * | 2007-11-29 | 2012-06-12 | Chevron Oronite Company Llc | Sulfurized metal alkyl phenate compositions having a low alkyl phenol content |
| US10150930B2 (en) | 2015-02-18 | 2018-12-11 | Chevron Oronite Technology B.V. | Low sulfur marine distillate fuel trunk piston engine oil composition |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1080531A (fr) * | 1952-02-01 | 1954-12-09 | Standard Oil Dev Co | Préparation de produits composés contenant des sulfonates métalliques et des selsmétalliques de sulfures aromatiques |
| USB194963I5 (en, 2012) * | 1962-05-15 | |||
| US3424679A (en) * | 1966-08-15 | 1969-01-28 | Chevron Res | Nonvicinal glycols in overbased phenate preparation |
-
1978
- 1978-02-08 FR FR7803464A patent/FR2416942A1/fr active Granted
-
1979
- 1979-01-24 EP EP79400045A patent/EP0003694B1/fr not_active Expired
- 1979-01-24 DE DE7979400045T patent/DE2962163D1/de not_active Expired
- 1979-01-26 US US06/006,866 patent/US4251379A/en not_active Expired - Lifetime
- 1979-02-06 AT AT0087079A patent/AT369354B/de not_active IP Right Cessation
- 1979-02-06 ES ES477477A patent/ES477477A1/es not_active Expired
- 1979-02-06 MX MX797704U patent/MX5771E/es unknown
- 1979-02-07 CA CA321,059A patent/CA1122962A/fr not_active Expired
- 1979-02-07 ZA ZA79532A patent/ZA79532B/xx unknown
- 1979-02-07 BR BR7900759A patent/BR7900759A/pt unknown
- 1979-02-07 IT IT47932/79A patent/IT1114549B/it active
- 1979-02-08 JP JP54012872A patent/JPS6018714B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2416942B1 (en, 2012) | 1982-04-30 |
| DE2962163D1 (en) | 1982-03-25 |
| MX5771E (es) | 1984-07-06 |
| BR7900759A (pt) | 1979-08-28 |
| AT369354B (de) | 1982-12-27 |
| ZA79532B (en) | 1980-02-27 |
| US4251379A (en) | 1981-02-17 |
| IT1114549B (it) | 1986-01-27 |
| JPS54132607A (en) | 1979-10-15 |
| IT7947932A0 (it) | 1979-02-07 |
| JPS6018714B2 (ja) | 1985-05-11 |
| EP0003694A1 (fr) | 1979-08-22 |
| EP0003694B1 (fr) | 1982-02-24 |
| ATA87079A (de) | 1982-05-15 |
| FR2416942A1 (fr) | 1979-09-07 |
| ES477477A1 (es) | 1979-07-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |