US2493216A - Mineral oil composition - Google Patents

Mineral oil composition Download PDF

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Publication number
US2493216A
US2493216A US673150A US67315046A US2493216A US 2493216 A US2493216 A US 2493216A US 673150 A US673150 A US 673150A US 67315046 A US67315046 A US 67315046A US 2493216 A US2493216 A US 2493216A
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Prior art keywords
oil
product
reaction
per cent
reaction product
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Henry G Berger
Everett W Fuller
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ExxonMobil Oil Corp
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Socony Vacuum Oil Co Inc
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Priority to NL71486D priority Critical patent/NL71486C/xx
Priority claimed from US539597A external-priority patent/US2416281A/en
Application filed by Socony Vacuum Oil Co Inc filed Critical Socony Vacuum Oil Co Inc
Priority to US673150A priority patent/US2493216A/en
Priority to US673152A priority patent/US2493217A/en
Priority to GB18726/47A priority patent/GB644043A/en
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Publication of US2493216A publication Critical patent/US2493216A/en
Priority to DES19741A priority patent/DE907332C/de
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    • C10M163/00—Lubricating compositions characterised by the additive being a mixture of a compound of unknown or incompletely defined constitution and a non-macromolecular compound, each of these compounds being essential
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    • C10M2207/128—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids containing hydroxy groups; Ethers thereof
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Definitions

  • This invention has-to do with a new and novel mineral oil composition and, more particularly, has to do with a mineral oil composition containing minor proportions of an oil-soluble detergent and of an oil-soluble, phosphorusand sulfurcontaining reaction product.
  • mineral oils are generally characterized by onevor more undesirable characteristics which limit their use.
  • One such characteristic is their instability under operating conditions normally encountered in present day engines, such that after a relatively short time, metal engine parts become contaminated with sludge, lacquer and resinous materials. In many instances, the said materials form in and about piston rings causing them to stick, the phenomenon being referred to as ring-sticking. As a consequence of the instability of the oil, engine operating emciency is seriously reduced.
  • Another undesirable characteristic of mineral oils is their tendency to oxidize, whereupon acidic materials are formed.
  • oil-soluble metal sulfonates are contemplated herein, typical of which are those obtained from aromatic hydrocarbons or substituted aromatic hydrocarbons, and a sulfonating agent such as strong sulfuric acid, oleum, chlor-'- sulfonic acid and the like.
  • Typical sulionates are those obtained by treatment of paraffins, naphthenes and various petroleum fractions-paraffinic, naphthenic or aromatic -with the same reagents.
  • All metals are contemplated herein as constituents of the said metal sulfonates. Especially suitable, however, are calcium, barium and zinc.
  • oils containing other detergentsoil-soluble salts of organic 'acids possessing cleansing or detergent action in oil are also substantially improved in character when a small amount of the aforesaid oi1- soluble, phosphorusand sulfur-containing reaction product of a phosphorus sulfide and a di-' assure typical salts are well known in the art and may be prepared by any suitable method.
  • the oil-soluble, phosphorusand sulfur-containing reaction products contemplated herein are those obtained by reacting a dicyclic terpene and a phosphorus sulfide at a temperature above about 100 C.
  • any one of the several phosphorus sulfides such as P381 (or P81), P48 (01' P281), P483, P285 (or P4510), P481, etc., may be used in the preparation of the said reaction products, particularly preferred are those reaction products obtained from Pass.
  • Dicyclic terpenes are defined herein as those" terpenes which are characterized by the presence of one double bond in the molecule and which are comprised of two ring systems. Typical of such terpenes are pinene, camphene and fenchene. contemplated as coming within this par ticular designation are those materials which are predominantly comprised of one or more dicyclic terpenes; representative of such materials are the essential or volatile oils which are predominantly comprised of such a terpene, or terpenes, and are typified by turpentine oil, the predominant constituent of which is pinene.
  • Preferred of the dicyclic terpene reactants are pinene'and turpentine oil. Accordingly, the preferred reaction prodnets are those obtained from Pass and pinene, and P385 and turpentine oil.
  • reaction product obtained in thisreaction contains phosphorus and sulfur in substantially the same amounts as was added in the phosphorus sulfide It wouldappear, then, that the reaction is one of addition; that is, addition of the phosphorus sulfide to the .one unsaturated bond present in pinene.
  • reaction temperature for the reaction described above should be one of at least about 100 C.
  • the preferred temperatures fall within the range of about 100 C. to about 160 C.
  • the proportions of reactants used herein may be'varied in order to prepare reaction products different degrees of oil solubility and different degrees of oil improving power. It is preferred, however, to use about 1 mol of a phos, phorus sulfide with 4 mols of a dicyclic terpene for the preparation of a reaction product readily soluble in petroleum oils. For example, when 4 by using approximately 1 mol of a phosphorus sulfide for every 4 mols of a dicyclic terpene.
  • a blend of a dicyclic terpene, such as pinene, and a comparatively inert solvent such as a petroleum'oil may be treated as described above to provide an oil blend of the reaction product.
  • the preferred procedure of this type involves the use of a 1:1 blend of dicyclic terpene and petroleum oil with a phosphorus sulfide, the molar ratio of said terpene to said sulfide being 4:1.
  • the oil compositions contemplated herein may also contain, in addition to an oil detergent and a dicyclic terpene-phosphorus sulfide reaction product, a small amount of one or more other oil-soluble, phosphorusand sulfur-containing reaction products.
  • One such reaction product is that which is obtained by reaction of approximore than 1 mol of P285 is used with 4 mols of pinene, a viscous gel-like reaction product is obmately 1 mol of phosphorus pentasulfide with 4 mols of oleyl alcohol, or ocenol, at a temperature between about 125 C. and about 150 C. for a relatively short time.
  • EXAMPLE 1 Basic barium diwax benzene suljonate A parafiln'wax having an average of 24 carbon atoms to the molecule and a melting point of 126 1". was chlorinated at about C. with chlorine gas until the weight of the wax had increased about 10%. The chlorowax (10% Cl) thus obtained was then blown with nitrogen to remove any occluded chlorine and hydrogen chloride.
  • EXAMPLE 2 Zinc diwax benzene suljonate A diwax benzene sulfonic acid was prepared as described in Example 1 above and this was then treated with zinc acetate. After distilling oil the acetic acid, the product was filtered through clay leaving a material-product B--that contained 3.36% zinc and 1.6% sulfur.
  • EXAMPLE 3 Basic barium diwax naphthalene sulfonate Five hundred (500) parts of chlorowax, containing 12% chlorine, were added to 500 parts of Stoddard solvent and 108 parts of naphthalene. The mixture was warmed to 5060 C. and 30 grams of AlCls were added gradually. When the reaction stopped the mixture was heated to 90 C. and blown with N2 gas to remove HCl. It was then allowed to stand overnight at room temperature. The lower sludge layer was removed and the oil layer was filtered through clay. This consisted essentially of diwax naphthalene.
  • the diwax naphthalene was treated with 250 parts of oleum (15% S03) by adding the latter slowly so as to keep the temperature at 40-50 C.
  • One thousand (1000) parts of water were then added with stirring and this was followed by 500 parts of an S. A. E. 30 grade motor oil.
  • the mixture was allowed to stand at 6070 C. overnight and the oil layer was then withdrawn.
  • This acid was treated with an excess of barium hydroxide and the mixture was heated to a maximum temperature of 150 C. in the presence of a stream of nitrogen to remove the water.
  • the Stoddard solvent was removed by heating to 170 C. at a vacuum of 5 mm. This left an approximately 50% solution of the basic barium diwax naphthalene sulfonate in the petroleum motor oil, which is identified herein as product C. It contained Ba and 2.0% S.
  • EXAMPLE4 Barium salt of petroleum oil sulfonate A Mid-Continent distillate of 95 seconds Saybolt viscosity at 100 F. was treated with oleum, the sludge was settled and removed, and the oil layer was neutralized with caustic soda solution. The sodium sulfonates thus formed were recovered by adding ethyl alcohol, separating the alcohol layer, and then evaporating off the alcohol. This left a mixture of oil and sodium sulfonates. This was contacted with a water solution of barium chloride and, after separation of the oil layer and drying, the latter-product D-was found to contain 6.9% Ba and 2.5% 8.
  • Vanadyl oleyl phthalate A mol of oleyl alcohol was reacted with 2. mol of phthalic anhydride to give the half ester of oleyl phthalate. This was neutralized with sodium hydroxide and the sodium salt thus formed was treated with vanadyl chloride to give the vanadyl salt of oleyl phthalate (3.94% vanadium), which is identified herein as product H.
  • EXAMPLE 9 Pinene-P2S reaction product Eight hundred (800) parts by weight of pinene and an equal weight of a motor oil (Saybolt Universal viscosity of 45 seconds at 210 F.) were heated to C. with stirring. Three hundred and twenty-six (326) parts of Pass (a ratio of 4 mols of pinene to 1 mol of P285) were added slowly the temperature rising to C. because of the exothermic reaction. The mixture was then heated to C. for 1 hour, 20 parts of clay were added and the resultant mixture filtered. The filtrate, consisting of 1842 parts by weight, was then vacuum topped at 5 mm. pressure to a pot temperature of 150 C. The residue consisting of 1693 parts by weight was a clear, viscous f oil-product X-containing 12.5% sulfur and 5.1% phosphorus.
  • EXAMPLE 10 Oleyl alcohol-P285 reaction product Approximately 4 mols of ocenol, a commercial material consisting essentially of oleyl alcohol, and 1 mol of P285 were reacted at about 150 C. for 2 hours. The resulting product-product Y- contained 5.0% phosphorus and 9.8% sulfur.
  • the apparatus used consists of a circulating 333332 3: 3 3: 1 :1 zi z g g: system whereby oil at 325 F. under a pressure of f 11 m m the time (in hours) pounds per square inch, is sprayed against a a z i'g 0 e 1 a b on that standard cadmium-nickel bearing for a period of a 22 1 y p it. 5 hours.
  • the amount of oil under constant cir- A t n u to culation in the system is 1500 cc.
  • the Detergent PEI'WCZmt 8mm Perwficnt Emu degree of oxidation suffered by the oil is shown by the development of acidity therein as meas- 29 Product A 4 M ured by the neutralization number (N. N.), the a g a loss in weight of the cadmium-nickel bearing g ggg 3 M and the percentage viscosity increase.
  • the oil used was a solvent refined oil having a Do 1 s I w saybolt Universal viscosity of 65 seconds at 210 F. and containing 0.17% Of Nuodex.
  • the results The results presented above in Table n demon- Of these are Shown in Table I belOW- state that an oil containing a small amount of Table 1 Percent Brg. t For t Detergent W Stabilizer ff N.N InVis. m
  • EXAMIPLEIZ The corrosivity of an oil and of an oil containing an oil detergent toward alloy bearings is demonstrated by the following test. Also demonstrated is the non-corrosive nature of the oil compositions contemplated herein, which contain small amounts of a phosphorusand sulfurcontaining reaction product of the aforesaid type, and an oil detergent.
  • EXAMPLE 14 As indicated hereinabove, preference is given A single cylinder Caterpillar Diesel engine was run for 96 hours at 19.8 brake horsepower and 1000 R. P. M. The oil temperature and the water temperature were both maintained at 195 F. The piston was then removed and rated for cleanliness. The results of several engine tests are presented in Table IV below.
  • 011 detergents defined as metal sulfonates or wax-substituted aromatic hydrocarbons.
  • This preference is infiuenced'by-their outstanding pour depressing properties as illustrated below in Table VI which gives results for products A and C, barium salts of diwax benzene sulfonic acid and diwax naphthalenesulfonic acid respectively, and for product D,- a barium salt of a sulfonic acid derived from petroleum ojll.
  • the two former materials are efiective in lowering the pour point while the latter is ineffective.
  • concentrations of from about 0.5% to about 10% of an oil detergent are used in an oil fraction, but concentrations of the order of about 4% have been found to be satisfactory for most purposes.
  • concentration of an oil soluble, phosphorusand sulfur-containing reaction product of a dicyclic terpene and a phosphorus sulfide may be varied from about 0.1% to about 3.0%; in general, however, about 0.5 will be satisfactory.
  • the mineral oil compositions of this invention may also contain one or more other oil-soluble, phosphorusand sulfurcontaining reaction products, such as those obtained from oleyl alcohol and P285, as defined above.
  • Oils of excellent quality are obtained with Oil +2% product F+0.25% product X...-... 272 from about 0.25% to about 2.0% of such a reac- 11' tion product, incorporated with the aforesaid quantities of an oil detergent and of a dicyclic terpene reaction product of the type defined above.
  • Mineral oil concentrates are also contemplated herein. such concentrates containing substantially larger concentrations of an oil detergent and of a dicyclic terpene-phosphorus sulfide reaction product, than those enumerated above. That is, relatively large amounts of the said materials may be incorporated in an oil fraction in which they are readily soluble, and the oil concentrate so obtained may thereafter be diluted with a suitable quantity of the said oil fraction prior to use. It is to be understood that these mineral oil concentrates may also contain one or more of the aforesaid other oil-soluble, phosphorusand sulfur-containing reaction products, such as those obtained from oleyl alcohol in amounts substantially in excess of those described above.
  • an oil detergent and a dicyclic terpene-phosphorus sulfide reaction product may be incorporated in a mineral oil in any one of several ways.
  • the dicyclic terpene reaction product may be added to an oil fraction containing an oil detergent; also, an oil detergent may be added to the reactants (dicyclic terpene and phosphorus sulfide) used in the preparation of the said reaction product and, in such case, will be present during the reaction.
  • the oil detergent may react with the dicyclic terpene and phosphorus sulfide to form a complex reaction product under the reaction conditions enumeratedabove; the product obtained in this manner may then be added to an oil fraction.
  • the mineral oil compositions and concentrates of this invention are complex in nature, for it is possible that an oil detergent and a dicyclic terpene-phosphorus sulfide reaction product may be present individually in an oil fraction, or may also be present therein as a physical combination or, further, may be present therein in the form of a single chemical composition. In the same connection, it will also used as a lubricant under certain conditions, such for example, as a lubricant in an engine operating at relatively high temperatures.
  • mineral oil composition is inclusive of all mineral oil fractions containing an oil detergent and a dicyclic terpene-phosphorus sulfide reaction product of the type defined above, in the concentrations previously enumerated, and is inclusive of oil compositions obtained or prepared by any of the aforesaid several procedures.
  • mineral oil concentra is inclusive of all mineral oil fractions containing relatively large amounts of the said 011 detergent and said reaction product.
  • An improved mineral oil composition comprising a viscous mineral oil fraction having in admixture therewith: a minor proportion, from about 0.5 per cent to about 10 per cent, of an oilsoluble metal sulfonate; a minor proportion, from about 0.1 per cent to about 3.0 per cent, of an oil-soluble, phosphorusand sulfur-containing reaction product obtained by reaction of a phosphorus sulfide and amaterial selected from the group consisting of a dicyclic terpene and an essential oil predominantly comprised of a dicyclic terpene, at a temperature greater than about C. and a minor proportion, from about 0.25 per cent to about 2.0 per cent. of an oil-soluble, phosphorusand sulfur-containing reaction product obtained by reaction of substantially one moi of phosphorus pentasulfide and four mols of oleyl alcohol at a temperature from about C. to about C. for a relatively short time.
  • An improved mineral oil composition comprising a viscous mineral oil fraction having in admixture therewith: a minor proportion, from about 0.5 per cent to about 10 per cent, of an oilsoluble, metal petroleum sulfonate; a minor proportion, from about 0.1 per cent to about 3.0 per cent, of an oil-soluble, phosphorusand sulfur-containing reaction product obtained by reaction of a phosphorus sulfide and a material selected from the group consisting of a dicyclic terpene and an essential oil predominantly comprised of a dicyclic terpene, at a temperature greater than about 100 C.; and a minor proportion, from about 0.25 per cent to about 2.0 per cent, of an oil-soluble, phosphorusand sulfurcontaining reaction product obtained by reaction of substantially one moi of phosphorus pentasulflde and four mols of oleyl alcohol at a temperature from about 125 C. to about 150". C. for a relatively short time.

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  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
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US2711395A (en) * 1953-11-25 1955-06-21 Sinclair Refining Co Cutting oil composition
DE942582C (de) * 1952-05-15 1956-05-03 Basf Ag Zusaetze fuer Schmiermittel
DE948075C (de) * 1952-05-15 1956-08-30 Basf Ag Zusaetze fuer Schmiermittel
US2762773A (en) * 1953-05-22 1956-09-11 Monsanto Chemicals Mineral oil compositions
US2798045A (en) * 1954-09-27 1957-07-02 Shell Dev Lubricating compositions
DE1031916B (de) * 1952-07-14 1958-06-12 Exxon Research Engineering Co Verfahren zur Herstellung von Zusatzstoffen fuer Mineraloele, z. B. Schmieroele
US2916451A (en) * 1952-12-18 1959-12-08 Monsanto Chemicals Oil-soluble carbonated metallo alkylated aryl sulfonates and compositions containing the same
US2928789A (en) * 1954-05-07 1960-03-15 Monsanto Chemicals Mineral oil compositions
US2969324A (en) * 1958-02-20 1961-01-24 Exxon Research Engineering Co Phosphosulfurized detergent-inhibitor additive
DE1137160B (de) * 1959-11-16 1962-09-27 Shell Int Research Hochdruckschmierfett und Verfahren zu seiner Herstellung
US3132101A (en) * 1956-05-21 1964-05-05 Sinclair Research Inc Detergent and anti-oxidant lubricant

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US2665252A (en) * 1948-09-25 1954-01-05 Lubrizol Corp Lubricants
US2658872A (en) * 1949-03-05 1953-11-10 Standard Oil Dev Co Modified copolymers and preparation and uses thereof
US2684334A (en) * 1951-05-25 1954-07-20 Shell Dev Lubricating oil containing a reaction product of p2s5-terpene and 2.4.6-trialkylphenol
NL228145A (is") * 1957-05-28

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US2375222A (en) * 1943-09-15 1945-05-08 Shell Dev Aviation lubricating oil
US2379453A (en) * 1944-06-01 1945-07-03 Socony Vacuum Oil Co Inc Mineral oil composition
US2411153A (en) * 1944-02-29 1946-11-19 Socony Vacuum Oil Co Inc Mineral oil composition and improving agent
US2416281A (en) * 1944-06-09 1947-02-25 Socony Vacuum Oil Co Inc Mineral oil composition

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US2256441A (en) * 1940-03-08 1941-09-16 Socony Vacuum Oil Co Inc Mineral oil composition and improving agent therefor
US2308503A (en) * 1940-08-02 1943-01-19 Standard Oil Co Compounded hydrocarbon oil

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2375222A (en) * 1943-09-15 1945-05-08 Shell Dev Aviation lubricating oil
US2411153A (en) * 1944-02-29 1946-11-19 Socony Vacuum Oil Co Inc Mineral oil composition and improving agent
US2379453A (en) * 1944-06-01 1945-07-03 Socony Vacuum Oil Co Inc Mineral oil composition
US2416281A (en) * 1944-06-09 1947-02-25 Socony Vacuum Oil Co Inc Mineral oil composition

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE942582C (de) * 1952-05-15 1956-05-03 Basf Ag Zusaetze fuer Schmiermittel
DE948075C (de) * 1952-05-15 1956-08-30 Basf Ag Zusaetze fuer Schmiermittel
DE1031916B (de) * 1952-07-14 1958-06-12 Exxon Research Engineering Co Verfahren zur Herstellung von Zusatzstoffen fuer Mineraloele, z. B. Schmieroele
US2916451A (en) * 1952-12-18 1959-12-08 Monsanto Chemicals Oil-soluble carbonated metallo alkylated aryl sulfonates and compositions containing the same
US2762773A (en) * 1953-05-22 1956-09-11 Monsanto Chemicals Mineral oil compositions
US2711395A (en) * 1953-11-25 1955-06-21 Sinclair Refining Co Cutting oil composition
US2928789A (en) * 1954-05-07 1960-03-15 Monsanto Chemicals Mineral oil compositions
US2798045A (en) * 1954-09-27 1957-07-02 Shell Dev Lubricating compositions
US3132101A (en) * 1956-05-21 1964-05-05 Sinclair Research Inc Detergent and anti-oxidant lubricant
US2969324A (en) * 1958-02-20 1961-01-24 Exxon Research Engineering Co Phosphosulfurized detergent-inhibitor additive
DE1137160B (de) * 1959-11-16 1962-09-27 Shell Int Research Hochdruckschmierfett und Verfahren zu seiner Herstellung

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