EP0016676B1 - Procédé de préparation d'alkylphénates de magnésium - Google Patents
Procédé de préparation d'alkylphénates de magnésium Download PDFInfo
- Publication number
- EP0016676B1 EP0016676B1 EP80400270A EP80400270A EP0016676B1 EP 0016676 B1 EP0016676 B1 EP 0016676B1 EP 80400270 A EP80400270 A EP 80400270A EP 80400270 A EP80400270 A EP 80400270A EP 0016676 B1 EP0016676 B1 EP 0016676B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- active
- magnesium oxide
- weight
- phenolic
- magnesium
- 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
- 239000011777 magnesium Substances 0.000 title claims abstract description 22
- 229910052749 magnesium Inorganic materials 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 66
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims abstract description 65
- 239000000395 magnesium oxide Substances 0.000 claims abstract description 49
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims abstract description 33
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000000725 suspension Substances 0.000 claims abstract description 20
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 17
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 11
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 7
- 238000009835 boiling Methods 0.000 claims abstract description 3
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000007865 diluting Methods 0.000 claims 3
- 239000003921 oil Substances 0.000 abstract description 23
- 238000010790 dilution Methods 0.000 abstract description 21
- 239000012895 dilution Substances 0.000 abstract description 21
- 239000000654 additive Substances 0.000 abstract description 6
- 239000010687 lubricating oil Substances 0.000 abstract description 6
- 239000002270 dispersing agent Substances 0.000 abstract description 5
- 230000000306 recurrent effect Effects 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 8
- KJWMCPYEODZESQ-UHFFFAOYSA-N 4-Dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=C(O)C=C1 KJWMCPYEODZESQ-UHFFFAOYSA-N 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- JOONSONEBWTBLT-UHFFFAOYSA-N 2-tetradecylphenol Chemical class CCCCCCCCCCCCCCC1=CC=CC=C1O JOONSONEBWTBLT-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 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
- 238000001354 calcination Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 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 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 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 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000005987 sulfurization reaction Methods 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
Definitions
- the present invention relates to a process for the preparation of magnesium alkylphenates, the products obtained according to the process and the application of said products as detergent-dispersant additives for lubricating oils.
- Such a process uses not an alkylphenol alone but an alkylphenol-sulfonic acid mixture which is easier to neutralize and requires the presence of a promoter.
- the Applicant has found a process making it possible to prepare magnesium alkylphenates using an alkylphenol alone (that is to say not mixed with a sulfonic acid), active magnesia and which does not require the use of a promoter.
- active magnesium oxide denotes magnesium oxide which can be obtained by gentle calcination of the basic magnesium carbonate, for example at a temperature of the order of 500 to 700 ° C. for at least 3 hours; the specific surface of this type of oxide is greater than 80 m 2 / g and generally greater than 100 m 2 / g.
- alkylphenol denotes both non-sulfurized alkylphenols and sulfurized alkylphenols.
- alkylphenols which can be used, mention may be made of those bearing one or more C 9 -C 15 substituents, in particular nonyl, decyl, dodecyl and tetradecylphenols, optionally sulfurized.
- paraffin spikes such as 100 Neutral oil
- naphthenic or mixed oils may also be suitable.
- heavy alcohols that can be used, mention may preferably be made of isobutanol, hexanol or 2-ethylhexanol.
- the operation of suspending the “active” magnesium oxide in methanol takes place favorably at ordinary temperature.
- the contacting and carbonation operations can be carried out at a temperature between 0 and 40 ° C. preferably between 15 and 30 ° C.
- the operations described above may optionally be followed by a water treatment operation, in particular when a ratio of the number of moles of “active” magnesium oxide / number of phenolic OH units greater than 1 has been set. in use and if one seeks to reduce the viscosity of the product obtained.
- This water treatment can be carried out in a conventional manner using 1 to 2 moles of water per mole of “active active” magnesium oxide.
- Another subject of the present invention is the magnesium alkylphenates obtained according to the process described above, as well as the application of said alkylphenates as detergent additives.
- dispersants for lubricating oils The amount of alkylphenates to be added to petrol engine oils is generally in the range of 1 to 4% by weight; that to be added in the oils for diesel engine is generally of the order of 1 to 8% by weight.
- the lubricating oils which can thus be improved can be chosen from a wide variety of lubricating oils, such as the naphthenic base, paraffinic base and mixed base lubricant oils, other hydrocarbon lubricants, for example lubricant oils.
- lubricating oils such as the naphthenic base, paraffinic base and mixed base lubricant oils, other hydrocarbon lubricants, for example lubricant oils.
- derived from coal products, and synthetic oils for example alkylene polymers, alkylene oxide type polymers and their derivatives, including alkylene oxide polymers prepared by polymerizing alkylene oxide in the presence of water or alcohols, for example ethyl alcohol, esters of dicarboxylic acids, liquid esters of liquid acids of phosphorus acids, alkylbenzenes and dialkylbenzenes, polyphenyls, alkylbiphenyl ethers, polymers of silicon.
- Additional additives may also be present in said lubricating oils alongside the detergent-dispersants obtained according to the process of the invention; include, for example, anti-oxidant, anti-corrosion additives, ashless dispersant additives, etc.
- the alkylphenol used is presulfurized paradodecyl phenol (A) containing 11.5% of sulfur (obtained by sulfurization with sulfur).
- the “active” magnesium oxide (B) used has a specific surface of 145 m 2 / g and a purity of MgO of 90%.
- the phenolic MgO / OH molar ratio used is 0.5.
- the amount of active MgO is 9% relative to methanol.
- the amount of dilution oil is 68.3% relative to the alkylphenol.
- a suspension of 11 g of the active magnesium oxide (B) (ie 0.25 mol) in 120 g of methanol is prepared separately and this suspension is added to the preceding mixture.
- the mixture thus obtained is then carbonated at 20 ° C with stirring by introducing into the reactor carbon dioxide under a pressure of 10 kg / cm 2 for 8 hours.
- the apparatus is brought back to atmospheric pressure and the methanol is removed by distillation while gradually raising the temperature to 180 ° C.
- Example 1 We repeat Example 1 but without first preparing the suspension of magnesium oxide in methanol and by loading all the constituents of the mixture without special precautions.
- Example 1 The operation described in Example 1 is carried out in the presence of an amount of MgO "active corresponding to 5% by weight of methanol.
- the suspension of “active MgO” thus consists of 11 g of active MgO (ie 0.25 mole) in 220 g of methanol.
- a suspension of 22 g of active magnesium oxide (B) (i.e. 0.5 mol) in 250 g of methanol is prepared and this suspension is added to the preceding mixture.
- the mixture is carbonated for 10 hours at room temperature under a pressure of 10 kg / cm 2 of carbon dioxide.
- the mixture is brought back to atmospheric pressure and the alcohols are removed by distillation by heating the product to 180 ° C. under vacuum to properly remove the hexanol.
- 270 g of finished product are thus recovered having a TBN of 170 mg and containing: 3.7% of magnesium and 3.5% of CO 2 while 20 g of crude product remain absorbed on the cake. filtration.
- a suspension of 19 g of active magnesium oxide (B) (i.e. 0.425 mole) in 220 g of methanol is prepared and we add this suspension to the preceding mixture.
- the mixture is carbonated for 10 hours at room temperature under a pressure of 12 kg / cm 2 of carbon dioxide.
- a suspension of 13 g of active magnesium oxide B (ie 0.3 mole) in 150 g of methanol is prepared and this suspension is added to the preceding mixture.
- the resulting mixture is carbonated for 8 hours at room temperature under a pressure of 12 kg / cm 2 of carbon dioxide.
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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT80400270T ATE1647T1 (de) | 1979-03-09 | 1980-02-27 | Verfahren zur herstellung von magnesiumalkylphenaten. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7906060 | 1979-03-09 | ||
| FR7906060A FR2450868A1 (fr) | 1979-03-09 | 1979-03-09 | Procede de preparation d'alkylphenates de magnesium et application des produits obtenus comme additifs detergents-dispersants pour huiles lubrifiantes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0016676A1 EP0016676A1 (fr) | 1980-10-01 |
| EP0016676B1 true EP0016676B1 (fr) | 1982-10-13 |
Family
ID=9222946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP80400270A Expired EP0016676B1 (fr) | 1979-03-09 | 1980-02-27 | Procédé de préparation d'alkylphénates de magnésium |
Country Status (11)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2529224B1 (fr) * | 1982-06-24 | 1986-02-07 | Orogil | Nouvel additif detergent-dispersant suralcalinise 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 |
| JPS60127396A (ja) * | 1983-12-12 | 1985-07-08 | Cosmo Co Ltd | 塩基性アルカリ土類金属サリチレ−ト型清浄剤の製造法 |
| JPS62127886U (enrdf_load_stackoverflow) * | 1986-02-06 | 1987-08-13 | ||
| JPS62178288U (enrdf_load_stackoverflow) * | 1986-05-06 | 1987-11-12 | ||
| US4971710A (en) * | 1986-10-21 | 1990-11-20 | Chevron Research Company | Methods for preparing, Group II metal overbased sulfurized alkylphenols |
| US5024773A (en) * | 1986-10-21 | 1991-06-18 | Chevron Research Company | Methods for preparing, group II metal overbased sulfurized alkylphenols |
| US4744921A (en) * | 1986-10-21 | 1988-05-17 | Chevron Research Company | Methods for preparing, group II metal overbased sulfurized alkylphenols |
| GB8730220D0 (en) * | 1987-12-29 | 1988-02-03 | Exxon Chemical Patents Inc | Detergents |
| US5292443A (en) * | 1992-08-21 | 1994-03-08 | Texaco Inc. | Process for producing neutralized sulfurized alkylphenate lubricant detergent additive |
| US6310009B1 (en) * | 2000-04-03 | 2001-10-30 | The Lubrizol Corporation | Lubricating oil compositions containing saligenin derivatives |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL107072C (enrdf_load_stackoverflow) * | 1960-03-09 | 1964-01-15 | ||
| US3350310A (en) * | 1965-02-08 | 1967-10-31 | Mobil Oil Corp | Preparation of overbased calcium alkylphenate sulfides |
| US4065396A (en) * | 1970-02-09 | 1977-12-27 | Bray Oil Co. | Magnesium oxide process |
| US3878116A (en) * | 1970-09-09 | 1975-04-15 | Bray Oil Co | Overbased sulfonates |
| US3932289A (en) * | 1973-11-09 | 1976-01-13 | Chevron Research Company | Preparation of overbased carbonated sulfurized magnesium alkylphenates |
| GB1470338A (en) * | 1974-05-17 | 1977-04-14 | Exxon Research Engineering Co | Lubricating oil compositions |
| GB1469289A (en) * | 1974-07-05 | 1977-04-06 | Exxon Research Engineering Co | Detergent additives |
| IT1044574B (it) * | 1975-07-14 | 1980-03-31 | Liquichimica Robassomero Spa | Additivo detergentfe per la sua preparazione |
| US4010106A (en) * | 1976-02-02 | 1977-03-01 | Chevron Research Company | Corrosion-retarding functional fluid |
| US4016093A (en) * | 1976-03-19 | 1977-04-05 | Mobil Oil Corporation | Metal alkylphenate sulfides of reduced corrosiveness and method of preparing same |
| FR2412607A1 (fr) * | 1977-12-20 | 1979-07-20 | Orogil | Nouveaux complexes basiques de magnesium et leur application pour la fabrication d'additifs detergents-dispersants pour huiles lubrifiantes |
-
1979
- 1979-03-09 FR FR7906060A patent/FR2450868A1/fr active Granted
-
1980
- 1980-02-27 DE DE8080400270T patent/DE3060929D1/de not_active Expired
- 1980-02-27 EP EP80400270A patent/EP0016676B1/fr not_active Expired
- 1980-02-27 AT AT80400270T patent/ATE1647T1/de not_active IP Right Cessation
- 1980-03-06 MX MX808695U patent/MX7049E/es unknown
- 1980-03-07 ZA ZA00801364A patent/ZA801364B/xx unknown
- 1980-03-07 ES ES489289A patent/ES489289A1/es not_active Expired
- 1980-03-07 BR BR8001372A patent/BR8001372A/pt unknown
- 1980-03-07 JP JP55028232A patent/JPS6011894B2/ja not_active Expired
- 1980-03-07 CA CA347,252A patent/CA1123015A/fr not_active Expired
-
1981
- 1981-08-03 US US06/289,220 patent/US4382004A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA1123015A (fr) | 1982-05-04 |
| FR2450868B1 (enrdf_load_stackoverflow) | 1983-05-20 |
| BR8001372A (pt) | 1980-11-11 |
| US4382004A (en) | 1983-05-03 |
| MX7049E (es) | 1987-04-07 |
| JPS6011894B2 (ja) | 1985-03-28 |
| EP0016676A1 (fr) | 1980-10-01 |
| DE3060929D1 (en) | 1982-11-18 |
| JPS55143923A (en) | 1980-11-10 |
| ATE1647T1 (de) | 1982-10-15 |
| ES489289A1 (es) | 1980-08-16 |
| FR2450868A1 (fr) | 1980-10-03 |
| ZA801364B (en) | 1981-03-25 |
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