US3249541A - Stabilized mineral oil compositions - Google Patents

Stabilized mineral oil compositions Download PDF

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Publication number
US3249541A
US3249541A US332855A US33285563A US3249541A US 3249541 A US3249541 A US 3249541A US 332855 A US332855 A US 332855A US 33285563 A US33285563 A US 33285563A US 3249541 A US3249541 A US 3249541A
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United States
Prior art keywords
oil
fuel
gms
mixture
primene
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US332855A
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English (en)
Inventor
Paul Y C Gee
Jr Harry J Andress
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ExxonMobil Oil Corp
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Socony Mobil Oil Co Inc
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Priority to US332855A priority Critical patent/US3249541A/en
Priority to FR995487A priority patent/FR1458938A/fr
Priority to DES94780A priority patent/DE1284010B/de
Priority to GB52232/64A priority patent/GB1086859A/en
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    • 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
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224—Amides; Imides carboxylic acid amides, imides
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/44—Preparation of metal salts or ammonium salts
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    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/08—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic sulfur-, selenium- or tellurium-containing compound
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    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/135—Steam engines or turbines

Definitions

  • This invention relates to stabilized mineral oil compositions and, more particularly, to mineral oil compositions adapted for use as fuel oils containing certain additives to inhibit the presence of sediment during prolonged periods of storage and to prevent screen-clogging and rusting of ferrous metal surfaces.
  • the invention furthermore, relates to mineral oil compositions adapted for use as lubricating oils containing the aforementioned additives as rust-inhibitors, which, aside from imparting such desired properties to fuel oils and lubricating oils, also inhibit such fuel oils and lubricating oils against undesirable emulsification.
  • emulsification of the oil is also objectionable in lubricating oils, and, in the case of turbine lubricating oils, is particularly objectionable in that the desired degree of lubrication for metal parts in contact with the emulsified oil, is reduced.
  • Another object of the invention is to provide new and improved stabilized mineral oil compositions containing the aforementioned additives, and which are useful as fuel oils and lubricating oils.
  • the present invention relates to mineral oil compositions containing a small amount, sufficient to provide the aforementioned improvements, of a metal salt of maleamic acid and a mixture of aliphatic hydrocarbyl primary branched-chain amines having from about 4 to about 30 carbon atoms per molecule.
  • the aforementioned mixtures of aliphatic hydrocarbyl primary branched-chain amines having about 4 to about 30 carbon atoms per molecule employed in forming the metal salts of maleamic acid therewith comprise, in general, the tertiary-alkyl primary mono-amines in which a carbon atom of a tertiary-alkyl group is attached to the amino group and which have from about 4 to about 30 carbon atoms, and preferably from about 12 to about 24 carbon atoms, per molecule.
  • these amines contain the group:
  • Non-limiting examples of these amine reactants are t-butyl amine, t-hexyl primary amine, n-octenylamine, toctyl primary amine, t-decyl primary amine, t-dodecyl primary amine, t-tetradecyl primary amine, t-octadecyl primary amine, t-eicosyl primary amine, t-docosyl primary amine, t-tetracosyl primary amine, and t-triacontyl primary amine.
  • the amine reactants can be prepared in several ways well known to those skilled in the art.
  • the metal of the metal salts of the additive compositions of the present invention is a divalent metal, and, preferably, includes magnesium, barium, calcium, zinc and strontium, although other divalent metals may also be employed.
  • the metal salts are prepared, in general, by first reacting one mole of the aforementioned aliphatic primary amines with one mole maleic anhydride at a temperature within the range from about 65 C. to about C., for a period of from about 1 to about 3 hours.
  • the resulting amine amic acid is next heated with the appropriate divalent metal, (e.g. a Group II metal), in the form of a metal alkoxide, or metal hydroxide, or, if so desired, by the use of an alkali metal hydroxide and double displacement with, for example, a Group II metal halide, (e.g., zinc chloride).
  • a Group II metal e.g., zinc chloride
  • the normal metal salts are prepared by heating two moles of the aforementioned amine amic acid with one mole of the metal alkoxide or metal hydroxide, for example, magnesium methoxide or magnesium hydroxide.
  • the alkoxy metal salts are prepared by heating one mole of the aforementioned amine amic acids with one mole of metal alkoxide, for example, magnesium rnethoxide.
  • the fuel oils that are improved in accordance with this invention are hydrocarbon fractions having an initial boiling point of at least about 100 F. and an end boiling point no higher than about 750 F., and boiling substantially continuously throughout their distillation range.
  • Such fuel oils are generally known as distillate fuel oils. It is to be understood, however, that this term is not restricted to straight-run distillate fractions.
  • the distillate fuel oils can be straight-run distillatefuel oils, catalytically or thermally cracked (including hydrocracked) distillate fuel oils, or mixtures of straight-run distillate fuel oils, naphthas and the like with cracked distillate fuel stocks.
  • such fuel oils can be treated in accordance with well known commercial methods, such as, acid or caustic treatment, hydrogenation, solvent refining, clay treatment, etc.
  • distillate fuel oils are characterized by their relatively low viscosities, pour points, and the like.
  • the principal property which characterizes the contemplated hydrocarbons, however, is the distillate range. As mentioned hereinbefore, this range will lie between about 100 F. and about 750 F. Obviously, the distillate range of each individual fuel oil will cover a narrower boiling range falling, nevertheless, within the above-specified limits. Likewise, each fuel oil will boil substantially continuously throughout its distillation range.
  • the fuel oils are Nos. 1, 2, and 3 fuel oils used in heating and as Diesel fuel oils, and the jet combustion fuels.
  • the domestic fuel oils generally conform to the specifications set forth in ASTM Specifications D396-48T.
  • Specifications for Diesel fuels are defined in ASTM Specifications D975-48T.
  • Typical jet fuels are defined in Military Specification MIL-F-5624B.
  • the amount of the metal salt of maleamic acid and the aforementioned amines that is added to the distillate fuel oil in accordance with this invention will depend, of course, upon the intended purpose and the particular metal salt selected, as they are not all equivalent in their activities. Some may have to be used in greater concentrations than others to be effective.
  • additive concentrations varying between 10 pounds per thousand barrels of oil and about 200 pounds per thousand barrels of oil will be employed. It may not always be desired, however, to accomplish all of the aforementioned results. In such cases, where it is desired to effect only one or two results, lower concentrations can be used. Thus, if it is desired only to prevent rust under dynamic conditions, as in a pipeline, it has been found that concentrations as low as about 5 p.p.m., i.e., about one pound of additive per thousand barrels of oil, are effective.
  • the amount of metal salt of maleamic acid and the aforementioned amines that can be added to the distillate fuel oil will vary generally between about one pound per thousand barrels of oil and about 200 pounds per thousand barrels of oil. Preferably, it will vary between about and about 200 pounds per thousand barrels of oil.
  • the fuel oil compositions can contain other additives for the purpose of achieving other results.
  • foam inhibitors and ignition and burning quality improvers are present.
  • silioones dinitropropane, amyl nitrate, metal sulfonates, and the like.
  • the additives embodied for use are effective to impart anti-rust properties while also inhibiting emulsification and, particularly, to impart such properties to highly refined mineral lubricating oils for use in steam turbines.
  • the additive embodied herein can be used in amounts that can vary over a rather wide range, based on the weight of the lubricating oil but, generally, in an amount of from about 0.001 to ten percent and, preferably, between about 0.05 and about one percent.
  • other substances can be added to the lubricating oil to impart other properties and, for example, anti-oxidants, pour point depressants, V.I. improvers, extreme pressure agents, etc.
  • the improving agents of this invention are useful for various petroleum fractions in concentrations ranging from about 0.001% up to about ten percent based on the weight of the fraction with the actual concentration used being dependent on the particular oil fraction (fuel oil or lubricating oil) and the use for which the improving agent is intended.
  • Primene 81R and Primene JMT used in the specific working Examples 1 through 10 are mixtures of pure amines.
  • Primene 81R is a mixture of primary amines having a carbon atom of a tertiary alkyl group attached to the amino (--NH group and containing 12 to 15 carbon atoms per amine molecule. This mixture contains, by weight, about 85 percent tertiarydodecyl primary amine, about 10 percent tertiary-pentadecyl primary amine, and relatively small amounts i.e., less than 5 percent of amines having less than 12 or more than 15 carbon atoms.
  • Primene JMT is a mixture of tertiary-alkyl primary amines containing 18 to 24 carbons, having a tertiary carbon atom attached to the NH group, and containing, by weight, about 40 percent tertiary-octadecyl primary amine, about 30 percent tertiary-eicosyl primary amine, about 15 percent tertiarydocosyl primary amine, about 10 percent tertiary-tetracosyl primary amine, and a small amount, less than 5 percent, other amines as high as tertiary-triacontyl primary amine.
  • Example 11 there is shown that the metal salts of maleamic acid prepared from primary straight-chain amines (rather than from the primary branched-chain amines of the present invention) are unsatisfactory as fuel additives, since they are found to develope undesirable, heavy emulsions with water in fuels; whereas the metal salts of the primary branched-chain maleamic acids of the present invention do not form such emulsions.
  • Armeen 12D is a mixture of primary straight-chain amines containing, approximately, by weight, 2 percent decylamine, percent dodecylamine, and 3 percent tetradecylamine.
  • EXAMPLE 1 A mixture of 49 gms. (0.5 mole) of maleic anhydride, gms. (0.5 mole) of Primene 81R and 310 gms. of xylene as diluent was stirred at 95-100 C. for two hours to form the Primene 81R maleamic acid. The Primene 81R maleamic acid was then added at room temperature with stirring to 6.1 gms. (0.25 mole) of magnesium in the form of a magnesium methylate solution. The mixture was gradually heated to C. and was held at 125 C. until the methanol stopped coming over. The reaction product was filtered through Hyflo clay. The final product, the magnesium salt of Primene 81R maleamic acid, which contained 66 /3% xylene, was clear and fluid at room temperature.
  • the mixture was gradually JMT maleamic acid, which contained 50% Process oil heated to 140 C. to distill out the methanol.
  • the reac- #5 was clear and fluid at room temperature.
  • tion product being viscous, was diluted with 366 gms. of xylene and filtered through Hyflo clay.
  • EXAMPLE 7 Percent Ba u 523
  • a mixture of 49 gms. (0.5 mole) of maleic anhydride, PercentN 1.0 1.13 100 gms. (0.5 mole) of Primene 81R and 100 cc. of xylene as diluent was stirred at 95 C. for 2 hours to form EXAMPLE 4 the Primene 81R maleamic acid.
  • To the Primene 81R 3O maleamic acid was added at room temperature with stir- A mixture of 49 mole) of malelc ahhydrlde, ring 20 gms.
  • EXAMPLE 5 A mixture of 49 Thole) of maleic anhydride, A mixture of 49 gms. (0.5 mole) of maleic anhydride, 100 gIhS- 111016) of Primene 81R and 150 of. 150 gms. (0.5 mole) of Primene JMT and 209 gms. of Xylene as diluent was Stirred at 2 hours to Process oil #5 was stirred at 95 C. for 2 hours to form form the Primene 81R maleamic acid.
  • the final product the zinc salt of Priroduct, the calcium salt of Primene JMT maleamic acid, mene 81R maleamic acid, which weight 150 gms., theory which contained 66 /s% Process oil #5, was clear and gms., was diluted with 158 gms. of xylene. fluid at room temperature.
  • the reaction mixture fluidized and was gradually heated to 150 C.
  • the reaction product was allowed to settle and filtered through Hyflo clay.
  • the test used to determine the sedimentation characteristics of the fuel oils is the 110 F. Storage Test.
  • a SOD-milliliter sample of the fuel oil under test is placed in a convected oven maintained at 110 F. for a period of 12 weeks. the oven and cooled. The cooled sample is filtered through a tared asbestos filter (Gooch crucible) to remove insoluble matter. The weight of such matter in milligrams is reported as the amount of sediment.
  • a sample of the blank, uninhibited oil is run along with a fuel oil blend under test. The effectiveness of a fuel oil containing an inhibitor is determined by comparing the weight of sediment formed in the inhibitor oil with that formed in the uninhibited oil.
  • Blank fuel blend Fail. Blank fuel blend plus Ex. 1. 50 Pass. Blank fuel blend plus Ex. 3- 10 D0. Blank fuel blend plus Ex. 4 25 Do. Blank fuel blend plus Ex. 5 Do. Blank fuel blend plus Ex. 7.-. 25 Do. Blank fuel blend plus Ex. 9. 25 D0. Blank fuel blend plus Ex. 10 25 Do.
  • addition agents also function as inhibitors against objectionable emulsification.
  • the presence of the tertiary carbon atom linked to the nitrogen atom in the alkyl grouping of the metal salts embodied herein is important as, when corresponding metal salts, but in which the nitrogen atom is linked to a normal primary aliphatic group, such salts induce severe emulsification with water.
  • Example 11 shows preparation of a magnesium salt of maleamic acid derived from Armeen 12D, which is a mixture of primary straight-chain amines as hereinbefore described.
  • fuel oil compositions were prepared by (1) addition of the metal salt of Example 1 at a concentration of 25 lbs./ thousand barrels of a fuel oil as used for the aforedescribed fuel oil tests and (2) addition in the same concentration in such a fuel of the metal salt of Example 11, and such fuel oil compositions were subjected to the following emulsion test:
  • Emulsion test The procedure for the fuel oil emulsion test is as follows: a 200 milliliter portion of the fuel to be tested and milliliters of distilled water are placed in a clear glass pint bottle. The bottle is tightly capped and set in an Everbach mechanical shaker in a horizontal position such that the maximum degree of agitation is afforded. The shaker is run at its maximum setting for 5 minutes. The bottle is then removed and allowed to stand in an upright position in the dark for 24 hours. At the end of the 24 hour settling period, the appearance of the water layer is noted. The fuel layer is siphoned off, care being taken not to disturb the oil-water interface, and is discarded. A fresh portion of the fuel oil being tested is then added. The described sequence of steps is repeated.
  • First sign of white emulsion Usually forms at the bottom and in the center of the bottle. It is circular in shape and approximately to 1 inch in diameter.
  • Circular emulsion at bottom of bottle extends outward and upward resembling spokes. Emulsion at the interface a little thicker than #4.
  • Emulsion on bottom of Water layer is almost solid. Emulsion on sides of bottle is broken in a feW spots enabling the operator to see the water layer.
  • a liquid mineral oil containing a small amount sufficient to inhibit corrosion of said oil of a divalent metal salt of the reaction product of maleic anhydride and a mixture of aliphatic hydrocarbyl primary branchedchain amines having from about 4 to about 30 carbon atoms per molecule.
  • composition as defined in claim 1, wherein the metal is a divalent metal of the group consisting of magnesium, barium, calcium, zinc and strontium.
  • composition as defined in claim 1 wherein the mineral oil is a distillate fuel oil having an initial boiling point of at least about 100 F. and an end boiling point not higher than about 750 F. and boiling substantially continuously throughout its distillation range.
  • a liquid mineral oil containing from about 1 to about 200 pounds, per thousand barrels of said oil, of a divalent metal salt of the reaction product of maleic anhydride and a mixture of aliphatic hydrocarbyl primary branchedchain amines having from about 4 to about 30 carbon atoms per molecule.
  • a liquid mineral oil containing from about 1 to about 200 pounds, per thousand barrels of said oil, of a divalent metal salt of the reaction product of maleic-anhydride and a mixture of primary amines having a carbon atom of a tertiary alkyl group attached to the amino group and having from about 12 to about 24 carbon atoms per amine molecule.
  • Aliquid mineral oil containing from about 1 to about 200 pounds, per thousand barrels of said oil, of a divalent metal salt of the reaction product of maleic anhydride and a mixture of primary amines having a carbon atom of a tertiary alkyl group attached to the amino group and having from about 12 to about 15 carbon atoms per amine molecule.
  • a liquid mineral oil containing from about 1 to about 200 pounds, per thousand barrels of said oil, of a divalent metal salt of the reaction product of maleic anhydride and a mixture of primary amines having a carbon atom of a tertiary alkyl group attached to the amino group and having from about 18 to about 24 carbon atoms per amine molecule.
  • metal is a divalent metal of the group consisting of magnesium, barium, calcium, zinc and strontium.

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US332855A 1963-12-23 1963-12-23 Stabilized mineral oil compositions Expired - Lifetime US3249541A (en)

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US332855A US3249541A (en) 1963-12-23 1963-12-23 Stabilized mineral oil compositions
FR995487A FR1458938A (fr) 1963-12-23 1964-11-19 Nouvelles compositions d'huiles minérales stabilisées
DES94780A DE1284010B (de) 1963-12-23 1964-12-22 Inhibitor gegen Rost-, Schlamm- und Emulsionsbildung in Distallatbrennstoffoelen
GB52232/64A GB1086859A (en) 1963-12-23 1964-12-23 Maleamic acid derivatives and mineral oil compositions containing them

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US4871375A (en) * 1987-07-30 1989-10-03 Basf Aktiensellschaft Fuels for Otto engines

Citations (3)

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Publication number Priority date Publication date Assignee Title
US2699427A (en) * 1952-10-02 1955-01-11 Gulf Oil Corp Mineral oil compositions containing amidic acids or salts thereof
US2977309A (en) * 1955-04-21 1961-03-28 Monsanto Chemicals Lubricating oil containing branched chain alkyl amine derivatives of dicarboxylic acids
US3046102A (en) * 1958-10-06 1962-07-24 Socony Mobil Oil Co Inc Stabilized distillate fuel oil

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Publication number Priority date Publication date Assignee Title
US2592204A (en) * 1949-02-15 1952-04-08 Socony Vacuum Oil Co Inc Mineral oil composition
US2692287A (en) * 1951-03-29 1954-10-19 Eastman Kodak Co Production of n-tertiary-alkylated aromatic secondary monoamines
US2945749A (en) * 1956-04-18 1960-07-19 Socony Mobil Oil Co Inc Stabilized fuel oil containing tertiary alkyl primary amines

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2699427A (en) * 1952-10-02 1955-01-11 Gulf Oil Corp Mineral oil compositions containing amidic acids or salts thereof
US2977309A (en) * 1955-04-21 1961-03-28 Monsanto Chemicals Lubricating oil containing branched chain alkyl amine derivatives of dicarboxylic acids
US3046102A (en) * 1958-10-06 1962-07-24 Socony Mobil Oil Co Inc Stabilized distillate fuel oil

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