US2727861A - Method of converting an ammonium petroleum sulfonate to barium sulfonate - Google Patents
Method of converting an ammonium petroleum sulfonate to barium sulfonate Download PDFInfo
- Publication number
- US2727861A US2727861A US297754A US29775452A US2727861A US 2727861 A US2727861 A US 2727861A US 297754 A US297754 A US 297754A US 29775452 A US29775452 A US 29775452A US 2727861 A US2727861 A US 2727861A
- Authority
- US
- United States
- Prior art keywords
- barium
- sulfonates
- ammonium
- alcohol
- petroleum
- 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 - Lifetime
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- 229910052788 barium Inorganic materials 0.000 title claims description 30
- 239000003208 petroleum Substances 0.000 title claims description 27
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 title claims description 19
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 11
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 title description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 48
- -1 HYDROXYL GROUPS Chemical group 0.000 claims description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000012141 concentrate Substances 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 7
- 239000003921 oil Substances 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000003809 water extraction Methods 0.000 claims description 4
- 150000001553 barium compounds Chemical class 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims 6
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 34
- 239000000203 mixture Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- 150000003871 sulfonates Chemical class 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 229910001863 barium hydroxide Inorganic materials 0.000 description 7
- 239000010687 lubricating oil Substances 0.000 description 7
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical compound [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 241000630665 Hada Species 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- CSSYLTMKCUORDA-UHFFFAOYSA-N barium(2+);oxygen(2-) Chemical group [O-2].[Ba+2] CSSYLTMKCUORDA-UHFFFAOYSA-N 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/62—Sulfonated fats, oils or waxes of undetermined constitution
Definitions
- Our invention relates to the production of concentrates of barium sulfonates in petroleum oils. More particularly, our invention relates to an improved method of converting ammonium petroleum sulfonates to barium petroleum sulfonates. Barium petroleum sulfonates are particularly valuable as addends for lubricating oils in which they act as corrosion inhibitors and efiective detergents.
- Pending application Serial No. 297,753 filed July 8, 1952, of Lee V. Brown discloses a process for the production of petroleum oil concentrates of barium sulfonates.
- the process comprises ammoniating an acid petroleum oil and treating the ammoniated oil with a solvent composed of water and a Water soluble lower aliphatic alcohol, e. g. isopropyl alcohol, of a concentration of about to 70 per cent isopropyl alcohol and at a solvent to oil ratio of 0.3 to 3.1.
- An alcohol soluble phase (extract) is recovered which contains ammonium sulfonates.
- the ammonium sulfonates are then reacted at a temperature of 175 to 250 F. with a barium compound, e. g.
- barium oxide or hydroxide to produce barium petroleum sulfonates.
- the reaction may be carried out with the dilute alcohol solution of ammonium sulfonates (extract) or with a concentrated solution obtained by topping the extract.
- extract dilute alcohol solution of ammonium sulfonates
- a concentrated solution obtained by topping the extract When the extract is used the resulting barium sulfonate solution is concentrated by heating to remove alcohol and water.
- an alcohol solution of ammonium sulfonates obtained by extraction of an ammoniated acid oil with a solvent composed of alcohol, e. g. isopropyl alcohol, and water, to a temperature of about 200 to 250 F. until essentially all the isopropyl alcohol is removed.
- the solution is first heated to about 200 F. and then the heated solution is flash distilled at a temperature of about 200 to 250 F. until essentially all the isopropyl alcohol is removed.
- the alcohol is recovered and also most of the water is removed.
- Ammonium sultonates containing more than about 1 per cent of water are more viscous and harder to handle.
- the bottoms from the alcohol removal step may then be steam stripped to insure the removal of essentially all of the alcohol.
- a concentrate of ammonium sulfonates in petroleum oils that is essentially isopropyl alcohol-free, e. g. less than about 1 per cent, is recovered and reacted at a temperature of about to 250 F. with barium oxide or bydroxide, either dry or in solution.
- a slurry is prepared by adding barium oxide to water.
- the barium oxide forms barium hydroxide and the heat of formation is efiectively utilized to maintain the temperature in the reaction zone at about 175 to 250 F., thereby substantially reducing the supply of heat required and correspondingly reducing heat transfer surface requirements.
- the essentially alcohol-free ammonium sulfonate concentrate is then added slowly to and intimately admixed with the slurry.
- the reactants are digested for about 1 hour at a temperature of about 175 to 250 F.
- the barium sulfonate solution formed is then dehydrated to about 300 F. Ammonia is removed and recovered. The solution is filtered while hot to separate excess barium oxide or hydroxide and the filtrate is recovered as a haze-free petroleum oil concentrate of barium sulfonates of high quality and concentration.
- the reaction proceeds smoothly, avoiding viscous reaction mixtures that prevent efiicient reaction and cause handling problems. Moreover, a haze-free barium sulfonate is produced that is highly desirable for use as a lubricating oil blending agent.
- the product of our invention forms clear solutions with lubricating oils, that are free of precipitates, and which are of superior marketability.
- Example Tests were run on the conversion to barium sulfonates of ammonium sulfonate solutions obtained by isopropyl alcohol and water extraction of an ammoniated acid petroleum oil.
- test 1 a decanted solution of barium oxide in 3 /2 parts of water was added to an alcohol solution of ammonium sulfonates (extract) at 170 F. The mixture was digested for 2.3 hours at 180 F. and stirred easily. The mixture was then dehydrated to 300 F. The filtering speed was rapid. The product contained 14.5 per cent barium, had a base number of 51.9, an O. D. color of 865 and was hazy.
- test 4 the extract was topped to a temperature of 208 F. and a solution of. barium oxide in 3% parts of water was added to the resulting concentrate at a temperature of 200 F.
- the mixture was digested for one hour at 200 F.
- the mixture formed a stiff emulsion during the. digestion period.
- the mixture was then dehydrated to 300 F.
- the filtering speed was rapid and the product was clear.
- the product contained 17.2 per cent barium and had a base number of 73.4 and an O. D. color of 1220.
- test 5 the extract-was topped to a temperature of 250 F., and the resulting concentrate was added to a slurry of barium oxide in 1 part of water over 30 minutes at 190 F. The mixture was digestedfor 1 hour at 190 F. and stirred easily. The mixture was then. dehydrated to 300 F. The filtration was rapid and the product was clear. The product contained 14.9 per cent barium and hada base number of 59.1 and an O. D. color oi 1322.
- test 4 show that a stifi emulsionformed when a barium oxide slurry was added to the concentrated ammonium sulfonate solution, apparently due to the formation of viscous neutral sulfonates.
- results of test 5 show, however, when the concentrated ammonium sulfonate solution was added to a barium oxide 4. slurry no emulsions were formed and the mixture stirred easily, apparently due to the formation of less viscous basic sulfonates.
- the method of producing hazefree petroleum oilv concentrates of barium sulfonates which comprises heating the ammonium sulfonates to a temperature of about 200 to 250 F. until the isopropyl alcohol content is less than about 1 per cent, recovering isopropyl alcohol, adding the resulting essentially isopropyl alcohol-free concentrate of ammonium su l'fonates to and intimately admixing it'with a barium compoundinwhich the barium is in combination. with a group selected from oxy and hydroxyl groups while maintaining. the tempera ture at about 175 to 250 F. and separating a hazefree concentrate of barium sulfonates in petroleum oils.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent METHOD OF CONVERTING AN AMIVIONIUM PETROLEUM SULFONATE TO BARIUM SULFONATE No Drawing. Application July 8, 1952, Serial No. 297,754
2 Claims. (Cl. 252-33) Our invention relates to the production of concentrates of barium sulfonates in petroleum oils. More particularly, our invention relates to an improved method of converting ammonium petroleum sulfonates to barium petroleum sulfonates. Barium petroleum sulfonates are particularly valuable as addends for lubricating oils in which they act as corrosion inhibitors and efiective detergents.
Pending application Serial No. 297,753 filed July 8, 1952, of Lee V. Brown discloses a process for the production of petroleum oil concentrates of barium sulfonates. The process comprises ammoniating an acid petroleum oil and treating the ammoniated oil with a solvent composed of water and a Water soluble lower aliphatic alcohol, e. g. isopropyl alcohol, of a concentration of about to 70 per cent isopropyl alcohol and at a solvent to oil ratio of 0.3 to 3.1. An alcohol soluble phase (extract) is recovered which contains ammonium sulfonates. The ammonium sulfonates are then reacted at a temperature of 175 to 250 F. with a barium compound, e. g. barium oxide or hydroxide, to produce barium petroleum sulfonates. The reaction may be carried out with the dilute alcohol solution of ammonium sulfonates (extract) or with a concentrated solution obtained by topping the extract. When the extract is used the resulting barium sulfonate solution is concentrated by heating to remove alcohol and water.
We have found, however, that in the conversion of ammonium sulfonates to barium sulfonates an unfilterable haze develops in the product when barium oxide or hydroxide comes into contact with an ammonium sulfonate mixture containing alcohol, e. g. isopropyl alcohol, during the reaction. The haze makes the product particularly undesirable for use as a lubricating oil blending agent as the lubricating oil blend has a hazy appearance that detracts from its marketability. Moreover, the barium sulfonates prepared in this manner often cause an undesirable precipitate to form when they are added to lubricating oil.
We have now found that reducing the amount of alcohol in ammonium sulfonates, obtained by aqueous alcohol extraction of an ammoniated acid petroleum oil, so that it is essentially alcohol-free, e. g. less than about 1 per cent isopropyl alcohol, and reacting this essentially alcohol-free concentrate with barium oxide or hydroxide produces desirable haze-free barium sulfonates that do not form precipitates with lubricating oil. The amount of alcohol is reduced by heating, advantageously flash distilling, the ammonium sulfonate solution to about 200 to 250 F. until the alcohol content is less than about 1 per cent. The bottoms from the flash distillation may, if desired, be steam stripped to insure a concentrate of less than 1 per cent alcohol.
We have also found that when barium oxide or hydroxide is added to an essentially alcohol-flee concentrate of ammonium sulfonates a viscous and even rubbery mixture forms that prevents proper stirring and eflicient reaction. This appears to be due to the formation of 2,727,861 Patented Dec. 20, 195 5- viscous neutral barium sulfonates. We have found, however, that adding the essentially alcohol-free concentrate of ammonium sulfonates slowly to the barium oxide or hydroxide avoids viscous mixtures and produces an eflicient reaction. It appears that the excess of barium compound causes the reaction to proceed directly to the formation of less viscous basic sulfonates.
According to the method of our invention, we heat an alcohol solution of ammonium sulfonates, obtained by extraction of an ammoniated acid oil with a solvent composed of alcohol, e. g. isopropyl alcohol, and water, to a temperature of about 200 to 250 F. until essentially all the isopropyl alcohol is removed. Advantageously, the solution is first heated to about 200 F. and then the heated solution is flash distilled at a temperature of about 200 to 250 F. until essentially all the isopropyl alcohol is removed. The alcohol is recovered and also most of the water is removed. We have found that it is advantageous to remove essentially all water from the ammonium sulfonates to eliminatehandling problems. Ammonium sultonates containing more than about 1 per cent of water are more viscous and harder to handle. The bottoms from the alcohol removal step may then be steam stripped to insure the removal of essentially all of the alcohol. A concentrate of ammonium sulfonates in petroleum oils that is essentially isopropyl alcohol-free, e. g. less than about 1 per cent, is recovered and reacted at a temperature of about to 250 F. with barium oxide or bydroxide, either dry or in solution.
Advantageously, a slurry is prepared by adding barium oxide to water. The barium oxide forms barium hydroxide and the heat of formation is efiectively utilized to maintain the temperature in the reaction zone at about 175 to 250 F., thereby substantially reducing the supply of heat required and correspondingly reducing heat transfer surface requirements. The essentially alcohol-free ammonium sulfonate concentrate is then added slowly to and intimately admixed with the slurry. The reactants are digested for about 1 hour at a temperature of about 175 to 250 F. The barium sulfonate solution formed is then dehydrated to about 300 F. Ammonia is removed and recovered. The solution is filtered while hot to separate excess barium oxide or hydroxide and the filtrate is recovered as a haze-free petroleum oil concentrate of barium sulfonates of high quality and concentration.
By the method of our invention the reaction proceeds smoothly, avoiding viscous reaction mixtures that prevent efiicient reaction and cause handling problems. Moreover, a haze-free barium sulfonate is produced that is highly desirable for use as a lubricating oil blending agent. The product of our invention forms clear solutions with lubricating oils, that are free of precipitates, and which are of superior marketability.
The method of our invention will be further illustrated by the following example.
Example Tests were run on the conversion to barium sulfonates of ammonium sulfonate solutions obtained by isopropyl alcohol and water extraction of an ammoniated acid petroleum oil.
In tests 1 to 3 inclusive, the conversion was carried out in the presence of some alcohol.
In test 1, a decanted solution of barium oxide in 3 /2 parts of water was added to an alcohol solution of ammonium sulfonates (extract) at 170 F. The mixture was digested for 2.3 hours at 180 F. and stirred easily. The mixture was then dehydrated to 300 F. The filtering speed was rapid. The product contained 14.5 per cent barium, had a base number of 51.9, an O. D. color of 865 and was hazy.
dry barium oxide was added to the topped extract at 150 F. with 25 per cent isopropyl alcohol (based on the extract) as a diluent. The mixture was digested for 1.3 hours at 155 F. and stirred easily. The mixture was thendehydrated to 300 F. The filtering speed was slow and the product was cloudy.
Other tests were run on an extract which had been topped to a temperature ofv208 to 250 F. to remove essentially all the alcohol present. These tests were 4 and 5.
In test 4, the extract was topped to a temperature of 208 F. and a solution of. barium oxide in 3% parts of water was added to the resulting concentrate at a temperature of 200 F. The mixture was digested for one hour at 200 F. The mixture formed a stiff emulsion during the. digestion period. The mixture was then dehydrated to 300 F. The filtering speed was rapid and the product was clear. vThe product contained 17.2 per cent barium and had a base number of 73.4 and an O. D. color of 1220.
In test 5, the extract-was topped to a temperature of 250 F., and the resulting concentrate was added to a slurry of barium oxide in 1 part of water over 30 minutes at 190 F. The mixture was digestedfor 1 hour at 190 F. and stirred easily. The mixture was then. dehydrated to 300 F. The filtration was rapid and the product was clear. The product contained 14.9 per cent barium and hada base number of 59.1 and an O. D. color oi 1322.
- The results of tests 1 to 3 show that a hazy product resulted when barium oxide was reacted with ammonium sulfonates in the presence of isopropyl alcohol. The results'of tests 4 and 5 show, however, that when essentially all the alcohol was removed from the ammonium sulfonatesolution and when no alcohol was present in the reaction with barium oxide 9. clear desirable product was obtained.
The'results of test 4 show that a stifi emulsionformed when a barium oxide slurry was added to the concentrated ammonium sulfonate solution, apparently due to the formation of viscous neutral sulfonates. The results of test 5 show, however, when the concentrated ammonium sulfonate solution was added to a barium oxide 4. slurry no emulsions were formed and the mixture stirred easily, apparently due to the formation of less viscous basic sulfonates.
Therefore, these tests show that to obtain a clear product and to avoid reaction difiiculties essentially all the alcohol must be removed from the ammonium sulfon'ate solution and the reaction must be carried out by adding the solution slowly to the barium oxide slurry.
We claim:
1. In the conversion of ammonium petroleum sulfonates, obtained by isopropyl alcohol and water extraction of an ammoniated acid petroleum oil, to barium petroleum sulfonates, the method of producing hazefree petroleum oilv concentrates of barium sulfonates which comprises heating the ammonium sulfonates to a temperature of about 200 to 250 F. until the isopropyl alcohol content is less than about 1 per cent, recovering isopropyl alcohol, adding the resulting essentially isopropyl alcohol-free concentrate of ammonium su l'fonates to and intimately admixing it'with a barium compoundinwhich the barium is in combination. with a group selected from oxy and hydroxyl groups while maintaining. the tempera ture at about 175 to 250 F. and separating a hazefree concentrate of barium sulfonates in petroleum oils.
2. In the conversion of ammonium petroleum sulfonates, obtained-by isopropyl alcohol and water extraction of an ammoniated acid petroleum oil to barium petroleum sulfonates, the method of producingv hazefree petroleum oil concentrates of barium sulfonates which,
References Cited in the file of this patent UNITED STATES PATENTS- 1,707,l87 Cobb Mar. 26, 1929 1,811,535 Buc June 23, 1931 2,097,440 Blumer Nov. 2, 1937 2,413,311 Cohen Dec. 31, 1946' 2,418,894 McNab .Apr. 15, 1947 2,509,863 Harlan May 30, 1950 2,559,439 Jones July 3, 1951 2,632,694
Watkins Mar. 24, 1953
Claims (1)
1. IN THE CONVERSION OF AMMONIUM PETROLEUM SULFONATES, OBTAINED BY ISOPRROPYL ALCOHOL AND WATER EXTRACTION OF AN AMMONIATED ACID PETROLEUM OIL, TO BARIUM PETROLEUM SULFONATES, THE METHOD OF PRODUCING HAZE-FREE PETROLEUM OIL CONCENTRATES OF BARIUM SULFONATES WHICH COMPRISES HEATING THE AMMONIUM SULFONATES TO A TEMPERATURE OF ABOUT 200* TO 250* F. UNTIL THE ISOPROPYL ALCOHOL CONTENT IS LESS THAN ABOUT 1 PER CENT, RECOVERING ISOPROPYL ALCOHOL ADDING THE RESULTING ESSENTIALLY IOSPROPYL ALCOHOL-FREE CONCENTRATED OF AMMONIUM SULFONATES TO AND INTIMATELY ADMIXING IT WITH A BARIUM COMPOUND IN WHICH THE BARIUM IS IN COMBINATION WITH A GROUP SELECTED FROM OXY AND HYDROXYL GROUPS WHILE MAINTAINING THE TEMPERATURE AT ABOUT 175* TO 250* F. AND SEPARATING A HAZEFREE CONCENTRATE OF BARIUM SULFONATES IN PETROLEUM OILS.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US297754A US2727861A (en) | 1952-07-08 | 1952-07-08 | Method of converting an ammonium petroleum sulfonate to barium sulfonate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US297754A US2727861A (en) | 1952-07-08 | 1952-07-08 | Method of converting an ammonium petroleum sulfonate to barium sulfonate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2727861A true US2727861A (en) | 1955-12-20 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US297754A Expired - Lifetime US2727861A (en) | 1952-07-08 | 1952-07-08 | Method of converting an ammonium petroleum sulfonate to barium sulfonate |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2727861A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2824126A (en) * | 1956-04-16 | 1958-02-18 | Bray Oil Co | Manufacture of sulfonates from petroleum oils |
| US2856359A (en) * | 1956-07-20 | 1958-10-14 | Texas Co | Superbasic alkaline earth metal sulfonates |
| US2856360A (en) * | 1956-07-20 | 1958-10-14 | Texas Co | Superbasic alkaline earth metal sulfonates |
| US2856361A (en) * | 1956-07-20 | 1958-10-14 | Texas Co | Superbasic alkaline earth metal sulfonates |
| US2924617A (en) * | 1955-06-27 | 1960-02-09 | Continental Oil Co | Preparation of oil-dispersible highly basic sulfonates |
| US2947694A (en) * | 1955-10-06 | 1960-08-02 | Phillips Petroleum Co | Preparation of metal petroleum sulfonates |
| US3959164A (en) * | 1972-12-20 | 1976-05-25 | Standard Oil Company | Method of preparing overbased barium sulfonates |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1707187A (en) * | 1925-10-27 | 1929-03-26 | Standard Oil Dev Co | Process for making white petrolatum |
| US1811535A (en) * | 1927-11-19 | 1931-06-23 | Standard Oil Dev Co | Processes for purification of oil soluble sodium sulphonates |
| US2097440A (en) * | 1934-10-16 | 1937-11-02 | Sonneborn Sons Inc L | Process for purifying mahogany soap |
| US2413311A (en) * | 1943-10-08 | 1946-12-31 | Standard Oil Dev Co | Lubricant and process for preparing same |
| US2418894A (en) * | 1944-12-09 | 1947-04-15 | Standard Oil Dev Co | Compounded lubricating oil |
| US2509863A (en) * | 1946-06-10 | 1950-05-30 | Standard Oil Dev Co | Method for producing divalent metal sulfonates |
| US2559439A (en) * | 1949-09-27 | 1951-07-03 | Shell Dev | Process of recovering sulfonates |
| US2632694A (en) * | 1950-11-14 | 1953-03-24 | Sinclair Refining Co | Petroleum distillates containing ammonium mahogany sulfonates and oil soluble carboxylic acids to prevent corrosion |
-
1952
- 1952-07-08 US US297754A patent/US2727861A/en not_active Expired - Lifetime
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1707187A (en) * | 1925-10-27 | 1929-03-26 | Standard Oil Dev Co | Process for making white petrolatum |
| US1811535A (en) * | 1927-11-19 | 1931-06-23 | Standard Oil Dev Co | Processes for purification of oil soluble sodium sulphonates |
| US2097440A (en) * | 1934-10-16 | 1937-11-02 | Sonneborn Sons Inc L | Process for purifying mahogany soap |
| US2413311A (en) * | 1943-10-08 | 1946-12-31 | Standard Oil Dev Co | Lubricant and process for preparing same |
| US2418894A (en) * | 1944-12-09 | 1947-04-15 | Standard Oil Dev Co | Compounded lubricating oil |
| US2509863A (en) * | 1946-06-10 | 1950-05-30 | Standard Oil Dev Co | Method for producing divalent metal sulfonates |
| US2559439A (en) * | 1949-09-27 | 1951-07-03 | Shell Dev | Process of recovering sulfonates |
| US2632694A (en) * | 1950-11-14 | 1953-03-24 | Sinclair Refining Co | Petroleum distillates containing ammonium mahogany sulfonates and oil soluble carboxylic acids to prevent corrosion |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2924617A (en) * | 1955-06-27 | 1960-02-09 | Continental Oil Co | Preparation of oil-dispersible highly basic sulfonates |
| US2947694A (en) * | 1955-10-06 | 1960-08-02 | Phillips Petroleum Co | Preparation of metal petroleum sulfonates |
| US2824126A (en) * | 1956-04-16 | 1958-02-18 | Bray Oil Co | Manufacture of sulfonates from petroleum oils |
| US2856359A (en) * | 1956-07-20 | 1958-10-14 | Texas Co | Superbasic alkaline earth metal sulfonates |
| US2856360A (en) * | 1956-07-20 | 1958-10-14 | Texas Co | Superbasic alkaline earth metal sulfonates |
| US2856361A (en) * | 1956-07-20 | 1958-10-14 | Texas Co | Superbasic alkaline earth metal sulfonates |
| US3959164A (en) * | 1972-12-20 | 1976-05-25 | Standard Oil Company | Method of preparing overbased barium sulfonates |
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