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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L10/00—Use of additives to fuels or fires for particular purposes
  • C10L10/02—Use of additives to fuels or fires for particular purposes for reducing smoke development
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • 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
  • 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

Definitions

• This invention relates to improvements in preparing alkaline earth sulfonates, in particular to an improved method of preparing highly basic alkaline earth sulfonates, and more particularly highly basic magnesium sulfonates.
• over-basing Increasing the alkalinity of alkaline earth sulfonates to provide an alkaline reserve is commonly referred to as over-basing or super-basing.
• Many methods have been proposed for obtaining compounds possessing an alkaline reserve. In general, such prior art methods make preparation by controlled carbonation of the alkaline earth oxide or hydroxide in the presence of the neutral sulfonic acid soap.
• the preparation of over based magnesium sulfonates is particularly different because of long reaction time, poor metal utilization and difiicult filtration.
• the above objects ate attained by preparing over-based alkaline earth sulfonates, particularly over-based magnesium sulfonates, in the presence of an amine promoter.
• the amine promoter used in concentrations of from about 0.05% to about 18% of the weight of the basic alkaline earth compound, may be introduced prior to or during the overbasing stage of the process, and may be retained in the final product or removed therefrom by suitable means.
• the process of the present invention comprises neutralizing at a temperature of from about 80 F. to about 212 F., a preferentially oil-soluble sulfonid acid, preferably in solution in a hydrocarbon solvent, which may be aromatic, e.g. xylenes or aliphatic, e.g. hexanes, with a basic alkaline earth compound, such as an alkaline earth oxide or hydroxide, adding to the neutral sulfonate an excess of the basic alkaline earth compound, the amine, a lower alkanol, e.g.
• a hydrocarbon solvent which may be aromatic, e.g. xylenes or aliphatic, e.g. hexanes
• a basic alkaline earth compound such as an alkaline earth oxide or hydroxide
• the carbon dioxide-treated product may be heated to reflux for about 10 minutes to about 60 minutes.
• water is added and the mixture may be blown with carbon dioxide for about 15 to minutes at about 70 F. to about 212 F.
• the mixture is then heated to remove water and solvent, and filtered. If desired, only the water may be removed prior to filtration, and the solvent removed after filtration.
• the amine can be added during the formation of the neutral sulfonate.
• Sulfonic acids suitably used in accordance with this invention are preferentially oil-soluble sulfonic acids.
• Such sulfonic acids include preferentially oil-solublepetroleum sulfonic acids, commonly referred to as mahogany acids, alkyl sulfonic acids, aryl sulfonic acids, and alkaryl sulfonic acids.
• suitable sulfonic acids are the preferentially oil-soluble petroleum sulfonic acids, e.g.
• sulfonic acids can be prepared by reacting the material to be sulfonated with a suitable sulfonating agent, such as concentrated sulfuric acid, fuming sulfuric acid, chlorosulfonic acid or sulfur trioxide for a period of time suflicient to effect sulfonation, and thereafter separating insoluble acid sludge from the oil-soluble sulfonic acid.
• a suitable sulfonating agent such as concentrated sulfuric acid, fuming sulfuric acid, chlorosulfonic acid or sulfur trioxide
• the amine promoter used in accordance with the present invention can be an aliphatic amine, an aromatic amine, or heterocyclic amine.
• Suitable amines are methylamine, N-methyloctylamine, dibutylamine, cyclohexylamine, dodecylamine, octadecylamine, methylene amines, ethylene amines, butylene amines, propylene amines, hexylene amines, ethylene diamine, triethylene tetramine, propylene diamine, octylmethylene diamine, tetraethylene pentamine, dipropylene triamine, 1,3-diamino propanes such as compounds of the general formula RNHCH CH CH NH in which R is the alkyl radical derived from tallow fatty acids and from cocoa fatty acids; such products are commercially marketed as Duomeen T and Duomeen C, respectively.
• Part 2 To the sulfonic acid solution of Part 1, free of sulfuric acid, were added 460 grams of a solvent extracted SAE petroleum oil, 450 grams of xylene, 16 grams of magnesium oxide and 200 cc. methanol, and the mixture stirred and heated at reflux temperature of about 160 F.
• Part 4 The product of Part 3 was heated to 190 F. to remove the methanol, then 50 grams of water added and the mixture heated to 270 F. The mixture was then cooled to 190 F., 100 grams of water added and the mixture blown with CO at 1.6 c.f.h. for one hour at 180 F.
• Part 5 The product of Part 4 was heated to 320 F. to remove the water and xylene and then filtered through diatomaceous earth.
• the recovered product had the following properties:
• Part 2 To the product of Part 1 were added 500 grams xylene, 110 grams magnesium oxide powder, 400 grams methanol, 50 cubic centimeters water and 20 grams ethylene diamine and the mixture stirred and cooled to a temperature of 76 F. Carbon dioxide was then passed into the mixture at the rate of 1.6 cubic feet per hour for 1.5 hours. The temperature of the mixture rose to 114 F after 55 minutes, and then fell to 104 F. at the end of 1.5 hours.
• Part 3 The product of Part 2 was then heated to 210 F. to remove the methanol, then 50 cc. of water added, and the mixture heated, without the reflux condenser, to 240 F. to distill 01f most of the water.
• Part 4 The product of Part 3 was then filtered at 240 F. through diatomaceous earth and the filtrate heated to 320 F. under reduced pressure to remove the xylene solvent.
• EXAMPLE III The product of this example was prepared substantially as in Example II, except that the ethylene diamine was omit d n P t 2, i
• Example II Example III Percent Sulfonate 30 34 Q Total Base Number 350 105 MgO Utilization, percent 95+ 33 Viscosity at F Fluid Fluid Filterability Excellent Fair EXAMPLE IV Part 1
• Part 2 The product of Part 2 was heated to 210 F. and 50 cubic centimeters of water added. The reflux condenser was removed and the mixture heated to 240 F. until substantially all of the water was distilled off.
• Part 4 The product of Part 3 was filtered through diatomaceous earth and the filtrate heated to 320 F. under reduced pressure to remove the xylenes.
• Example IV Example V Percent Sulfonate 30 34 Total Base Number 250 97 MgO Utilization. percent 38 Viscosity at 80 F Fluid Fluid Filterability Excellent Good
• the data presented by the foregoing examples demonstrate that the use of amine promoters in the preparation of over-based alkaline earth sulfonates in accordance with the herein-described invention results in improved metal utilization, improved filterability, shorter reaction time and increase total base number of the sulfonates. While in the examples given we have employed magnesium oxide as the basic alkaline earth compound, similar results are attainable with the hydroxides, carbonates and oxides of the other members of the alkaline earth group, such as, for example, calcium and barium.
• step (d) is treated with additional carbon dioxide prior to removal of water therefrom.
• alkaryl sulfonate is a polypropylene-alkylated benzene sulfonate in which the polypropylene substituent has a molecular weight of about 290-1500.
• reaction mixture contains about 2.75-4 mols of magnesium oxide.

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• Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Combustion & Propulsion (AREA)
• Lubricants (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Liquid Carbonaceous Fuels (AREA)

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Cited By (11)

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Citations (7)

• 1966
  • 1966-05-27 US US553326A patent/US3492230A/en not_active Expired - Lifetime
• 1967
  • 1967-05-25 NL NL676707246A patent/NL140859B/xx not_active IP Right Cessation
  • 1967-05-25 BE BE699010D patent/BE699010A/xx not_active IP Right Cessation
  • 1967-05-26 GB GB24705/67A patent/GB1166744A/en not_active Expired
  • 1967-05-26 JP JP42033190A patent/JPS4913782B1/ja active Pending
  • 1967-05-26 LU LU53755D patent/LU53755A1/xx unknown

Patent Citations (7)

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