CA1253873A - Process for the preparation of sulphurized overbased salicylates - Google Patents
Process for the preparation of sulphurized overbased salicylatesInfo
- Publication number
- CA1253873A CA1253873A CA000484253A CA484253A CA1253873A CA 1253873 A CA1253873 A CA 1253873A CA 000484253 A CA000484253 A CA 000484253A CA 484253 A CA484253 A CA 484253A CA 1253873 A CA1253873 A CA 1253873A
- Authority
- CA
- Canada
- Prior art keywords
- overbased
- sulphurized
- process according
- meq
- salicylic acid
- 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
- 238000000034 method Methods 0.000 title claims abstract description 16
- 150000003873 salicylate salts Chemical class 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims abstract description 21
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000005864 Sulphur Substances 0.000 claims abstract description 12
- 229910052751 metal Inorganic materials 0.000 claims abstract description 12
- 239000002184 metal Substances 0.000 claims abstract description 12
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229960004889 salicylic acid Drugs 0.000 claims abstract description 11
- 229960001860 salicylate Drugs 0.000 claims abstract description 10
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims description 13
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- -1 alkaline earth metal salicylate Chemical class 0.000 claims description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract description 14
- 239000001569 carbon dioxide Substances 0.000 abstract description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract description 7
- 125000001931 aliphatic group Chemical group 0.000 abstract description 4
- 150000003819 basic metal compounds Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 18
- 239000003921 oil Substances 0.000 description 14
- 239000002253 acid Substances 0.000 description 10
- 239000011575 calcium Substances 0.000 description 9
- 238000006114 decarboxylation reaction Methods 0.000 description 8
- 239000010688 mineral lubricating oil Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- 239000010687 lubricating oil Substances 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
- 235000011116 calcium hydroxide Nutrition 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003749 cleanliness Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000295 fuel oil Substances 0.000 description 2
- 239000003502 gasoline Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XOJRBTBFGUKLPU-UHFFFAOYSA-N 2,5-ditert-butyl-4-[(2,5-ditert-butyl-4-hydroxyphenyl)methyl]phenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(CC=2C(=CC(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1C(C)(C)C XOJRBTBFGUKLPU-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- 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 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical class [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C10M159/22—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing phenol 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Carbonaceous Fuels (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848417297A GB8417297D0 (en) | 1984-07-06 | 1984-07-06 | Preparation of sulphurized overbased salicylates |
| GB8417297 | 1984-07-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1253873A true CA1253873A (en) | 1989-05-09 |
Family
ID=10563523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000484253A Expired CA1253873A (en) | 1984-07-06 | 1985-06-17 | Process for the preparation of sulphurized overbased salicylates |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0168880B1 (en, 2012) |
| JP (1) | JPS6124560A (en, 2012) |
| BR (1) | BR8503201A (en, 2012) |
| CA (1) | CA1253873A (en, 2012) |
| DE (1) | DE3564570D1 (en, 2012) |
| GB (1) | GB8417297D0 (en, 2012) |
| SG (1) | SG7090G (en, 2012) |
| ZA (1) | ZA855048B (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63266424A (ja) * | 1987-04-24 | 1988-11-02 | Alps Electric Co Ltd | 液晶表示素子 |
| GB8714922D0 (en) * | 1987-06-25 | 1987-07-29 | Shell Int Research | Lubricating oil composition |
| JPH0676589B2 (ja) * | 1987-07-24 | 1994-09-28 | コスモ石油株式会社 | ヒドロキシアルキル安息香酸およびアルキルフェノ−ルのアルカリ土類金属塩硫化混合物の製造法 |
| JPH083767Y2 (ja) * | 1992-07-09 | 1996-01-31 | 日本ピラー工業株式会社 | 軸封装置 |
| MX9305120A (es) * | 1992-09-04 | 1994-03-31 | Lubrizol Corp | Composiciones sobrebasificadas sulfuradas. |
| TW278098B (en, 2012) * | 1992-09-18 | 1996-06-11 | Cosmo Sogo Kenkyusho Kk | |
| US6828415B2 (en) | 1993-02-19 | 2004-12-07 | Zentaris Gmbh | Oligopeptide lyophilisate, their preparation and use |
| JPH1161165A (ja) * | 1997-06-12 | 1999-03-05 | Tonen Corp | サリチル酸金属塩からなる摩擦低減剤およびそれを含有する潤滑油組成物 |
| US7136522B2 (en) * | 2002-10-09 | 2006-11-14 | Xerox Corporation | Systems for spectral multiplexing of source images to provide a composite image, for rendering the composite image, and for spectral demultiplexing of the composite image to animate recovered source images |
| JP2005220197A (ja) * | 2004-02-04 | 2005-08-18 | Nippon Oil Corp | 鉛含有金属材料と接触する潤滑油組成物 |
| US7956022B2 (en) | 2005-07-29 | 2011-06-07 | Chevron Oronite Company Llc | Low sulfur metal detergent-dispersants |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2319662A (en) * | 1941-10-31 | 1943-05-18 | American Cyanamid Co | Lubricating oils |
| US2311931A (en) * | 1941-12-27 | 1943-02-23 | American Cyanamid Co | Lubricant |
| USRE22910E (en) * | 1941-12-31 | 1947-09-02 | E-oxcxs-m | |
| US2336074A (en) * | 1942-05-16 | 1943-12-07 | American Cyanamid Co | Lubricating oil |
| GB786167A (en) * | 1954-09-27 | 1957-11-13 | Shell Res Ltd | Improvements in or relating to the preparation of basic oil-soluble polyvalent metalsalts of organic acids and solutions of said basic salts in oils, and the resultingsalts |
| GB825315A (en) * | 1957-02-18 | 1959-12-16 | Socony Mobil Oil Co Inc | Complex carbonated metal salts of alkyl phenol sulphides |
| GB1094609A (en) * | 1965-08-23 | 1967-12-13 | Lubrizol Corp | Oil soluble basic alkaline earth metal salts of phenol sulfides |
| US3595791A (en) * | 1969-03-11 | 1971-07-27 | Lubrizol Corp | Basic,sulfurized salicylates and method for their preparation |
| SU644811A1 (ru) * | 1975-07-14 | 1980-02-05 | Всесоюзный научно-исследовательский институт по переработке нефти | Способ получени сульфидалкилфенол тной присадки к смазочных маслам |
| GB1597482A (en) * | 1977-01-28 | 1981-09-09 | Exxon Research Engineering Co | Metal phenates |
| US4228022A (en) * | 1979-06-28 | 1980-10-14 | Chevron Research Company | Sulfurized alkylphenol-olefin reaction product lubricating oil additive |
| US4320016A (en) * | 1979-09-24 | 1982-03-16 | Texaco Inc. | Carbon dioxide-blown overbased calcium alkylphenolate lubricating compositions |
| IN155264B (en, 2012) * | 1979-11-07 | 1985-01-12 | Lubrizol Corp | |
| JPH07103390B2 (ja) * | 1982-05-14 | 1995-11-08 | エクソン リサーチ アンド エンヂニアリング コムパニー | 潤滑油添加剤 |
-
1984
- 1984-07-06 GB GB848417297A patent/GB8417297D0/en active Pending
-
1985
- 1985-06-17 CA CA000484253A patent/CA1253873A/en not_active Expired
- 1985-07-04 JP JP14760585A patent/JPS6124560A/ja active Granted
- 1985-07-04 DE DE8585201083T patent/DE3564570D1/de not_active Expired
- 1985-07-04 BR BR8503201A patent/BR8503201A/pt not_active IP Right Cessation
- 1985-07-04 EP EP85201083A patent/EP0168880B1/en not_active Expired
- 1985-07-04 ZA ZA855048A patent/ZA855048B/xx unknown
-
1990
- 1990-02-05 SG SG70/90A patent/SG7090G/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE3564570D1 (en) | 1988-09-29 |
| JPH0580517B2 (en, 2012) | 1993-11-09 |
| BR8503201A (pt) | 1986-03-25 |
| GB8417297D0 (en) | 1984-08-08 |
| ZA855048B (en) | 1986-02-26 |
| EP0168880A1 (en) | 1986-01-22 |
| EP0168880B1 (en) | 1988-08-24 |
| SG7090G (en) | 1990-07-13 |
| JPS6124560A (ja) | 1986-02-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |