GB844335A - High barium content complex salts of sulphonic acids - Google Patents
High barium content complex salts of sulphonic acidsInfo
- Publication number
- GB844335A GB844335A GB10481/58A GB1048158A GB844335A GB 844335 A GB844335 A GB 844335A GB 10481/58 A GB10481/58 A GB 10481/58A GB 1048158 A GB1048158 A GB 1048158A GB 844335 A GB844335 A GB 844335A
- Authority
- GB
- United Kingdom
- Prior art keywords
- barium
- oil
- solution
- basic
- methylate
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
- C10L1/2431—Organic compounds containing sulfur, selenium and/or tellurium sulfur bond to oxygen, e.g. sulfones, sulfoxides
- C10L1/2437—Sulfonic acids; Derivatives thereof, e.g. sulfonamides, sulfosuccinic acid esters
-
- 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
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
-
- 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—Overbasedsulfonic acid salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/251—Alcohol fueled engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
- C10N2040/28—Rotary engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
- F02B3/00—Engines characterised by air compression and subsequent fuel addition
- F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
Complex carbonated barium sulphonates, which contain a high percentage of barium, are obtained by reacting a solution, in hydrocarbon oil, of a basic barium sulphonate of the general formula: <FORM:0844335/IV(b)/1> with carbon dioxide followed by basic barium methylate. In the above formula, A is a benzene or naphthalene nucleus, R is an alkyl radical containing 8 to 24 carbon atoms, and n is 1 to 5. The oil solution is maintained at a temperature of from about 150 DEG C. to about 250 DEG C. while the carbon dioxide is passed into it, and the treatment is continued until at least 1 mol of CO2 has reacted with each mol of basic barium sulphonate. The reaction-mixture is then cooled to about 25 DEG -60 DEG C., and barium methylate BaOH(OCH3) is added in an amount sufficient to provide at least 1 equivalent of barium per mol of basic barium sulphonate. The product contains 3 equivalents of barium, and may be subjected to further carbonation and barium methylate treatments to obtain salts of higher barium content. Salts having 14 equivalents of barium per equivalent of sulphonic acid have been prepared, the ratio of combined CO2 to Ba in the salt being approximately 1:1. The products are useful as addition agents for lubricating and fuel oils (see Group III). Suitable starting materials are produced by the action of barium hydroxide on acids obtained by sulphonation of petroleum or synthetic alkyl-substituted benzenes and naphthalenes wherein the alkyl groups contain 8 to 24 carbon atoms. In an example, paraffin wax having an average of 24 carbon atoms per molecule is chlorinated at about 100 DEG C. until its weight has increased by about 12 DEG . The chlorowax is reacted, at 60 DEG -100 DEG C., with benzene in such proportions that there is 1 mol of benzene per 2 atomic proportions of chlorine in the chlorowax, the reaction being catalysed by aluminium chloride. The waxbenzene is reacted with oleum, and the product is poured into water. The mixture is stirred with a solvent refined Mid-Continent oil, and allowed to stand; the water is then drained-off. Barium hydroxide octahydrate is added to the solution of the wax-benzene sulphonic acid, and the temperature of the mixture is slowly raised to 150 DEG C. and held there for 1 hour. The solution of the basic barium salt is filtered through diatomaceous clay, and diluted with mineral oil to provide a solution (Product A) containing 7,5% by weight of barium. This solution is blown with CO2 for 3 hours at 200 DEG C. The mixture is cooled to 60 DEG C., and a solution of barium methylate is methanol is added. The mixture is then heated to 175 DEG C. to eliminate uncombined methanol, and filtered. The product is an oil blend containing 10% of barium. In Example 2, Product A is subjected to a two-stage process, of carbonation and barium methylate addition, to yield an oil blend p containing 13% of barium. In Example 4, the oil blend containing 10% of barium obtained in the first example is subjected to a three-stage process, of carbonation and barium addition, to yield an oil blend containing 18% of barium. Example 6 describes the preparation, from Product A, of an oil blend containing 31,5% of barium by a twelve-stage process of carbonation and barium-addition.ALSO:Hydrocarbon oils (e.g. mineral lubricating oils or fuel oils) contain dissolved therein complex carbonated barium sulphonates containing a high percentage (viz. 10 to 30%) of barium. The additives are prepared by reacting a hydrocarbon oil solution of a basic barium salt of an alkylated aromatic sulphonic acid first with carbon dioxide and then with basic barium methylate (see Group IV(b)). In examples, the starting material is a mineral oil solution of the basic barium salt of a C24-alkyl benzene sulphonic acid, from which oil blends containing 10, 13, 16, 18, 21 and 31.5% barium are obtained, although basic barium salts of petroleum sulphonic acids are also mentioned. The Specification gives the results of comparative tests (showing the sludge-inhibiting and wear-inhibiting properties of the additives) carried out on gasoline- and diesel-engines using mineral lubricating oils with and without minor proportions (3 to 6%) of one or other of the high-barium oil blends referred to above. The Specification also includes the results of tests which evaluate the ability of the complex barium salts to prevent the deterioration of fuel oil on storage, and as anti-screen clogging agents in contaminated fuel oil. The fuel oil employed comprised a blend of 60% catalytically cracked component and 40% straight-run component and had a boiling-range of approximately 320 DEG to 640 DEG F.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US664465A US3046224A (en) | 1957-06-10 | 1957-06-10 | High barium content complex salts of sulfonic acids and petroleum fractions containing the same |
US813069A US3031284A (en) | 1957-06-10 | 1959-05-14 | Fuel oil compositions containing high barium content complex salts of sulfonic acids |
US813070A US3158572A (en) | 1957-06-10 | 1959-05-14 | High barium content complex salts of sulfonic acids and method for preparing same |
Publications (1)
Publication Number | Publication Date |
---|---|
GB844335A true GB844335A (en) | 1960-08-10 |
Family
ID=27418107
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB10481/58A Expired GB844335A (en) | 1957-06-10 | 1958-04-01 | High barium content complex salts of sulphonic acids |
Country Status (2)
Country | Link |
---|---|
US (3) | US3046224A (en) |
GB (1) | GB844335A (en) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3172855A (en) * | 1965-03-09 | Barium-calcium sulfonate complexes and lubricating compositions con- taining same | ||
US3213019A (en) * | 1962-02-15 | 1965-10-19 | Socony Mobil Oil Co Inc | High barium-content carbonated salts of phosphorus sulfide-hydrocarbon products and method for preparing the same |
GB1077560A (en) * | 1964-04-06 | 1967-08-02 | Lubrizol Corp | Diesel fuel |
US3852204A (en) * | 1966-02-01 | 1974-12-03 | Cosden Oil & Chem Co | Lubricant compositions |
US4116644A (en) * | 1975-03-24 | 1978-09-26 | Jackisch Philip F | Gasoline compositions |
DE2861399D1 (en) * | 1977-08-04 | 1982-01-28 | Exxon Research Engineering Co | Overbased monoalkyl orthoxylene and monoalkyl toluene sulfonates and use as lubricant additives |
US4159973A (en) * | 1978-03-06 | 1979-07-03 | Tenneco Chemicals, Inc. | Stabilizer systems and vinyl halide resin compositions containing same |
US4665117A (en) * | 1985-12-20 | 1987-05-12 | The Lubrizol Corporation | Basic metal salts having improved color and stability and vinyl halide polymers containing same |
US4661544A (en) * | 1985-12-20 | 1987-04-28 | The Lubrizol Corporation | Homogeneous stabilizer compositions for vinyl halide polymers |
GB8723909D0 (en) * | 1987-10-12 | 1987-11-18 | Exxon Chemical Patents Inc | Lubricant oil additive |
US5859267A (en) * | 1995-11-08 | 1999-01-12 | Omg Americas, Inc. | Process for improving color of basic metal organic salts and stabilizing halogen-containing polymers therewith |
US5830935A (en) * | 1996-06-13 | 1998-11-03 | Omg Americas, Inc. | Color of basic metal organic salts by employing C7 -C17 alkyl glycidyl esters and stabilized halogen-containing polymers |
ATE236867T1 (en) | 1997-08-26 | 2003-04-15 | Omg Americas Inc | METHOD FOR IMPROVING THE STORAGE STABILITY OF LIQUID OVERBASE CALCIUM CARBOXYLATES, METAL MIX STABILIZERS CONTAINING THESE, AND STABILIZATION OF HALOGEN-CONTAINING POLYMERS WITH THESE |
US6639090B2 (en) | 2001-05-18 | 2003-10-28 | Omg Americas, Inc. | Powdered overbased amorphous alkaline earth metal salts and processes for making |
US6773631B2 (en) * | 2001-05-18 | 2004-08-10 | Hammond Group, Inc. | Liquid overbased mixed metal stabilizer composition of calcium, barium and zinc for stabilizing halogen-containing polymers |
US6689893B2 (en) | 2001-05-18 | 2004-02-10 | Omg Americas, Inc. | Shelf stable haze free liquids of overbased alkaline earth metal salts |
US7163912B2 (en) * | 2001-05-18 | 2007-01-16 | Omg Americas, Inc. | Lubricant compositions containing an overbased amorphous alkaline earth metal salt as a metal protectant |
US20090264327A1 (en) * | 2008-04-21 | 2009-10-22 | Omg Americas, Inc. | Overbased metal carboxylate precursor and process for making |
US9102610B2 (en) | 2011-11-29 | 2015-08-11 | Am Stabilizers Corporation | Process for preparing liquid overbased metal carboxylates, mixed metal stabilizers containing same, and stabilized halogen-containing polymers therewith |
US9828487B2 (en) | 2013-03-15 | 2017-11-28 | Delta specialties | Liquid compositions of overbased calcium carboxylate and process for its preparation |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2296069A (en) * | 1940-03-21 | 1942-09-15 | Allied Chem & Dye Corp | Fuel for internal combustion engines |
US2413311A (en) * | 1943-10-08 | 1946-12-31 | Standard Oil Dev Co | Lubricant and process for preparing same |
US2501731A (en) * | 1946-10-14 | 1950-03-28 | Union Oil Co | Modified lubricating oil |
US2585520A (en) * | 1948-12-03 | 1952-02-12 | Shell Dev | Lubricating compositions containing highly basic metal sulfonates |
US2866694A (en) * | 1950-09-02 | 1958-12-30 | Shell Dev | Anti-clogging fuel oil compositions |
US2695910A (en) * | 1951-05-03 | 1954-11-30 | Lubrizol Corp | Methods of preparation of superbased salts |
BE511937A (en) * | 1951-06-07 | |||
US2767209A (en) * | 1952-11-03 | 1956-10-16 | Lubrizol Corp | Complexes of dissimilar metals and methods of making same |
US2794828A (en) * | 1953-04-10 | 1957-06-04 | Sonneborn Sons Inc L | Petroleum mahogany sulfonates with high alkaline earth metal content |
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 |
US2791558A (en) * | 1954-10-21 | 1957-05-07 | Standard Oil Co | Sulfonate composition of high barium content |
US2861951A (en) * | 1955-04-27 | 1958-11-25 | Continental Oil Co | Method of dispersing barium carbonate in a non-volatile carrier |
US2924617A (en) * | 1955-06-27 | 1960-02-09 | Continental Oil Co | Preparation of oil-dispersible highly basic sulfonates |
US2856360A (en) * | 1956-07-20 | 1958-10-14 | Texas Co | Superbasic alkaline earth metal sulfonates |
BE533324A (en) * | 1957-02-06 | |||
US2881206A (en) * | 1957-04-08 | 1959-04-07 | Sinclair Refining Co | Process for preparing stable high detergency barium sulfonates |
NL228145A (en) * | 1957-05-28 |
-
1957
- 1957-06-10 US US664465A patent/US3046224A/en not_active Expired - Lifetime
-
1958
- 1958-04-01 GB GB10481/58A patent/GB844335A/en not_active Expired
-
1959
- 1959-05-14 US US813069A patent/US3031284A/en not_active Expired - Lifetime
- 1959-05-14 US US813070A patent/US3158572A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
US3158572A (en) | 1964-11-24 |
US3046224A (en) | 1962-07-24 |
US3031284A (en) | 1962-04-24 |
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