CA1103699A - Alkylates and sulphonic acids and sulphonates produced therefrom - Google Patents
Alkylates and sulphonic acids and sulphonates produced therefromInfo
- Publication number
- CA1103699A CA1103699A CA295,829A CA295829A CA1103699A CA 1103699 A CA1103699 A CA 1103699A CA 295829 A CA295829 A CA 295829A CA 1103699 A CA1103699 A CA 1103699A
- Authority
- CA
- Canada
- Prior art keywords
- cation
- sulphonates
- alkylate
- olefine
- sulfonates
- 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
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 title description 25
- 239000002253 acid Substances 0.000 title description 12
- 150000007513 acids Chemical class 0.000 title description 12
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims description 31
- 229910052791 calcium Inorganic materials 0.000 claims description 19
- 239000011575 calcium Substances 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 12
- 150000001768 cations Chemical class 0.000 claims description 12
- 150000001491 aromatic compounds Chemical class 0.000 claims description 11
- 150000001336 alkenes Chemical class 0.000 claims description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 6
- 229910052788 barium Inorganic materials 0.000 claims description 6
- 229910052749 magnesium Inorganic materials 0.000 claims description 6
- 239000011777 magnesium Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 230000002152 alkylating effect Effects 0.000 claims description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 150000003871 sulfonates Chemical class 0.000 claims 7
- 150000003460 sulfonic acids Chemical class 0.000 claims 6
- 238000006277 sulfonation reaction Methods 0.000 claims 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract description 19
- 238000005187 foaming Methods 0.000 abstract description 12
- 125000000217 alkyl group Chemical group 0.000 abstract description 7
- 238000005804 alkylation reaction Methods 0.000 abstract description 6
- 239000003995 emulsifying agent Substances 0.000 abstract description 6
- 230000029936 alkylation Effects 0.000 abstract description 5
- 239000003879 lubricant additive Substances 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 239000000314 lubricant Substances 0.000 description 9
- -1 alkyl aromatic compounds Chemical class 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 6
- 239000002518 antifoaming agent Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 150000004996 alkyl benzenes Chemical class 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000010687 lubricating oil Substances 0.000 description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 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
- 235000010269 sulphur dioxide Nutrition 0.000 description 2
- 239000004291 sulphur dioxide Substances 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001246 colloidal dispersion Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical group NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/12—Sulfonates of aromatic or alkylated aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
- C07C2/70—Catalytic processes with acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
- C10M135/10—Sulfonic acids or derivatives 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
- 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
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral 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
- C10M2219/04—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—Overbased sulfonic acid salts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB355777 | 1977-01-28 | ||
| GB3557/77 | 1977-01-28 | ||
| GB32726/77 | 1977-08-04 | ||
| GB3272677 | 1977-08-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1103699A true CA1103699A (en) | 1981-06-23 |
Family
ID=26238417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA295,829A Expired CA1103699A (en) | 1977-01-28 | 1978-01-27 | Alkylates and sulphonic acids and sulphonates produced therefrom |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5395924A (enrdf_load_stackoverflow) |
| CA (1) | CA1103699A (enrdf_load_stackoverflow) |
| DE (1) | DE2803420A1 (enrdf_load_stackoverflow) |
| FR (2) | FR2381004A1 (enrdf_load_stackoverflow) |
| IT (1) | IT1091965B (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5071576A (en) * | 1987-10-12 | 1991-12-10 | Exxon Chemical Patents Inc. | Lubricant oil additive |
| US5089155A (en) * | 1987-10-12 | 1992-02-18 | Exxon Chemical Patents Inc. | Overbased magnesium sulphonate composition |
| US5112506A (en) * | 1987-10-12 | 1992-05-12 | Exxon Chemical Patents Inc. | Overbased metal sulphonate composition |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63168792U (enrdf_load_stackoverflow) * | 1987-04-20 | 1988-11-02 | ||
| CA2204461C (en) * | 1996-05-14 | 2006-07-04 | Thomas V. Harris | Process for producing an alkylated, non-oxygen-containing aromatic hydrocarbon |
| JP4632465B2 (ja) * | 1997-05-30 | 2011-02-16 | 東燃ゼネラル石油株式会社 | 潤滑油組成物 |
| US6392109B1 (en) * | 2000-02-29 | 2002-05-21 | Chevron U.S.A. Inc. | Synthesis of alkybenzenes and synlubes from Fischer-Tropsch products |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2712530A (en) * | 1950-03-31 | 1955-07-05 | Exxon Research Engineering Co | Sulfonate detergent blend |
| GB749737A (en) * | 1953-12-30 | 1956-05-30 | Exxon Research Engineering Co | Sulfonate detergent blend |
| US2806875A (en) * | 1954-06-21 | 1957-09-17 | Continental Oil Co | Preparation of alkaryl sulfonic acids |
| NL214609A (enrdf_load_stackoverflow) * | 1957-02-15 | |||
| US3410925A (en) * | 1964-05-14 | 1968-11-12 | Continental Oil Co | Dimerization of c3 to c18 olefins |
| GB1093359A (en) * | 1965-08-12 | 1967-11-29 | Grange Chemicals Ltd | Production of heavy alkylate |
| US3681442A (en) | 1968-12-26 | 1972-08-01 | Universal Oil Prod Co | Alkylaromatic sulfonate detergent process of preparation |
| US3732324A (en) * | 1971-04-02 | 1973-05-08 | Continental Oil Co | Process for producing oil-soluble sulfonate feedstock |
| US3772198A (en) | 1971-06-07 | 1973-11-13 | Continental Oil Co | Method for preparing overbased oil soluble compositions |
| FR2264011B1 (enrdf_load_stackoverflow) | 1974-03-13 | 1978-01-06 | Exxon Research Engineering Co | |
| GB1572496A (en) | 1976-02-20 | 1980-07-30 | Exxon Research Engineering Co | Stabilisation of alkylaryl sulphonic acids and sulphonates |
-
1978
- 1978-01-12 IT IT19220/78A patent/IT1091965B/it active
- 1978-01-13 JP JP259878A patent/JPS5395924A/ja active Granted
- 1978-01-26 DE DE19782803420 patent/DE2803420A1/de active Granted
- 1978-01-27 FR FR7802401A patent/FR2381004A1/fr active Granted
- 1978-01-27 CA CA295,829A patent/CA1103699A/en not_active Expired
- 1978-06-01 FR FR7816457A patent/FR2381026A1/fr active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5071576A (en) * | 1987-10-12 | 1991-12-10 | Exxon Chemical Patents Inc. | Lubricant oil additive |
| US5089155A (en) * | 1987-10-12 | 1992-02-18 | Exxon Chemical Patents Inc. | Overbased magnesium sulphonate composition |
| US5112506A (en) * | 1987-10-12 | 1992-05-12 | Exxon Chemical Patents Inc. | Overbased metal sulphonate composition |
| US5137648A (en) * | 1987-10-12 | 1992-08-11 | Exxon Chemical Patents Inc. | Overbased metal sulphonate composition |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1091965B (it) | 1985-07-06 |
| FR2381026A1 (fr) | 1978-09-15 |
| FR2381004A1 (fr) | 1978-09-15 |
| IT7819220A0 (it) | 1978-01-12 |
| DE2803420C2 (enrdf_load_stackoverflow) | 1992-10-29 |
| JPS5395924A (en) | 1978-08-22 |
| JPS629093B2 (enrdf_load_stackoverflow) | 1987-02-26 |
| FR2381026B1 (enrdf_load_stackoverflow) | 1983-09-30 |
| DE2803420A1 (de) | 1978-08-31 |
| FR2381004B1 (enrdf_load_stackoverflow) | 1981-06-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |