US2416985A - Compounded mineral oil - Google Patents

Compounded mineral oil Download PDF

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Publication number
US2416985A
US2416985A US374078A US37407841A US2416985A US 2416985 A US2416985 A US 2416985A US 374078 A US374078 A US 374078A US 37407841 A US37407841 A US 37407841A US 2416985 A US2416985 A US 2416985A
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United States
Prior art keywords
phosphate
oil
aluminum
calcium
acid
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
Application number
US374078A
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English (en)
Inventor
Bruce B Farrington
James O Clayton
John T Rutherford
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
California Research LLC
Original Assignee
California Research LLC
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to BE436573D priority Critical patent/BE436573A/xx
Priority to NL54880D priority patent/NL54880C/xx
Priority claimed from US241648A external-priority patent/US2228659A/en
Priority to US242292A priority patent/US2228671A/en
Priority to CH221931D priority patent/CH221931A/de
Priority to FR860580D priority patent/FR860580A/fr
Priority to GB27128/39A priority patent/GB537816A/en
Priority to GB30163/39A priority patent/GB538474A/en
Priority to GB30164/39A priority patent/GB539293A/en
Priority to NL95973A priority patent/NL60510C/xx
Priority to CH222547D priority patent/CH222547A/de
Application filed by California Research LLC filed Critical California Research LLC
Priority to US374078A priority patent/US2416985A/en
Priority to US374241A priority patent/US2321804A/en
Priority to US471276A priority patent/US2382043A/en
Publication of US2416985A publication Critical patent/US2416985A/en
Application granted granted Critical
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Expired - Lifetime legal-status Critical Current

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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
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    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
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    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
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    • C10N2040/30—Refrigerators lubricants or compressors lubricants
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    • C10N2040/32—Wires, ropes or cables lubricants
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    • C10N2040/34—Lubricating-sealants
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    • C10N2040/36—Release agents or mold release agents
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    • C10N2040/42—Flashing oils or marking oils
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    • C10N2050/10—Semi-solids; greasy
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    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • This invention relates to a new and useful composition of matter and involves a composition comprising a viscous hydrocarbon oil and a polyvalent metal salt of certain substituted acids of phosphorus.
  • a characteristic which has been the subject of extensive investigation is the tendency of hydrocarbon oils to deteriorate or partially decompose and oxidize when subjected to high temperatures. This deterioration is evidenced by the deposition of adhesive deposits on hot metal surfaces over which the hydrocarbon oil may flow. It is important that resistance to such deterioration be imparted to hydrocarbon oils, particularly to lubricating oils, in order that such compositions may be relatively free from the tendency to form such deposits even under high temperatures and severe operating conditions.
  • a direct result .of this type of deterioration during lubrication of internal combustion engines, such as engines of the Diesel type is the tendency of the oil to cause or permit the sticking of pistonrings.
  • crankcase lubricant in internal combustion engines is subjected to extremely severe operating conditions and in engines of the Diesel type the lubricant encounters in the piston ring zone temperatures of from approximately e25 to 650 F, and pressures from the oxidizing combustion gases as high as 750 to 1150 lbs. per sq. in.
  • Addition agents which render hydrocarbon oils resistant to deterioration by heat at high temperature levels in the order of those above mentioned usually impart to the oil the ability to inhibit piston ring sticking in internal combustion engines and permit longer periods of operation of such engines without the necessity of major overhauls heretofore occasioned by stuck piston rings.
  • stabilizing agents which are effective at low temperatures to impart increased stability to hydrocarbon oils, or which are effective at temperatures even as high as 200 or 250 F., are often ineffective under the more severe operating conditions and higher tem-, perature levels to which lubricating oils are subjected in Diesel engines.
  • a stabilizer at atmospheric temperatures, or even temperatures as high as 200 to 300 F. gives no adequate basis for predicting the action of the same stabilizing. agent at materially higher temperatures and under more severe operating conditions.
  • the disclosures in the prior art relative to such stabilizers therefore cannot serve as a guide for one seeking stabilizing agents or oxidation inhibitors effective at higher temperature levels.
  • the phenomena involved are catalytic in nature, are highly empirical and require extensive experimentation to determine the action of a given type of addition agent.
  • Th present invention involves the discovery that dispersion of polyvalent metal salts of substituted oxy acids of phosphorus in hydrocarbon oils such as mineral lubricating oil imparts new, unpredictable and highly desirable properties to the compositinon. These new properties render the compounded oil particularly usefulfor various purposes.
  • increased resistance to deterioration at high temperature levels comprises one of th principal advantages of the compounded oils of this invention, it is to be understood that the invention is not limited to this feature, that different compounds of the general type herein involved vary in their degree of eifectiveness and may impart one ,or more other desirable properties to th lubricating composition. For example, certain of the compounds reduce the amount of Wear produced as compared with a straight uncompounded mineral oil.
  • the new compositions herein disclosed are more stable to heat than is a hydrocarbon oil with which the compositions are compounded.
  • the new compositions of this invention are therefore useful where resistance to deterioration by heat is important.
  • An example of such utility other than as a lubricating oil, comprises use as a heat transfer fluid where it may be desirable to inhibit or prevent the formation of a deposit on the metal surfaces from or to which heat is being conveyed.
  • the increased resistance to oxidation imparted to the .oil by the compounds of this invention will find various applications as, for instance, in an insulating, switch, or transformer oil.
  • Metal salts of substituted oxy acids of phosphorus which may be added to hydrocarbon lubricating oils to provide a new composition of matter of the type herein involved comprise the salts of metals selected from groups 11, III, IV and VI of Mendeleffs Periodic Table of the Elements. Specific examples of such metals are aluminum, calcium, barium, strontium, chromium and magnesium. Salts of iron, cobalt, nicke1, zinc, tin and lead comprise additional examples of compounds falling within the broader aspects of the invention.
  • the metal salts of this invention are preferably formed from substituted oxy acids of pentavalent phosphorus of the following type formulae:
  • R and R may be alkyl, aryl, alkaryl, aralkyl or cyclic nonbenzenoid radicals.
  • Substituted phosphoric acids containing at least twelve carbon atoms are preferred.
  • Examples of preferred type acids are alkyl or alkaryl substituted phosphoric acids having at least twelve carbon atoms in the molecule.
  • the broader aspects of the invention include the use of other types of substituted oxy acids of phosphorus containing more than twelve carbon atoms. Additional examples of substituted oxy acids of phosphorus which may be used in forming the metal salts of the present invention are as follows:
  • R and R may be alkyl, aryl, alkaryl, aralkyl or cyclic nonbenzenoid groups.
  • substituted or substituted derivatives of acids of phosphorus such as phosphorous acid, hypophosphoric acid, HzPOs; orthophosphoric acid, H3PO4; pyrophosphoric acid, H4P2O7; fall within the broadest aspects of the invention.
  • substituted or substituted derivatives of acids of phosphorus whenever used herein, it is intended to designate acids containing an organic group of the type previously listed, 1. e., alkyl, aryl, alkaryl, aralkyl, or cyclic nonbenzenoid groups.
  • the organic groups may be either directly attached to the phosphorus atom of the compound or attached thereto through an intervening atom such as oxygen.
  • oxy acids of phosphorus is intended to designate throughout the specification and claims acidsiof phosphorus in which one oxygen atom may intervene between the hydrogen and phosphorus atoms of the ester.
  • the preferred acids are substituted orthophosphoric acids and the preferred salts comprise the aluminum, calcium, barium and chromium salts of these acids.
  • such salts are aluminum lauryl phosphate, aluminum cetyl phosphate, aluminum octadecyl phosphate, aluminum spermol phosphate, aluminum oley1 phosphate, aluminum spermenyl phosphate, aluminum cetyl phenyl phosphate, aluminum di-(amylphenyl) phosphate, aluminum naphthenyl phosphate; calcium lauryl phosphate, calcium cetyl phosphate, calcium octadecyl phosphate, calcium spermol phosphate, calcium oleyl phosphate, calcium spermenyl phosphate, calcium cetyl phenyl phosphate, calcium di-(amylphenyl) phosphate, calcium naphthenyl phosphate; chromium lauryl phosphate, chromium cetyl phosphate, chro
  • the substituted oxy acids of phosphorus utilized in the present invention may be prepared by methods known in the art. For example, a mixture of a higher alcohol and phosphorus pentoxide in ethyl ether may be refluxed for several hours.
  • the reaction by which the substituted phosphoric acid is formed in this operation is believed to be represented by the following equation:
  • R is an alkyl radical.
  • the alkyl ethyl phosphoric acid is soluble in ether, while the ethyl meta phosphate is not and the ether solution of the former may-be separated from the latter by decantation.
  • Table 1 gives a number of TABLE 1 Acid Method of preparation Monocetylphosphoric 9.25 lb. cetyl alcohol and 5.61 lb.
  • P205 were refluxed with 5 gal. ethyl ether for 24 hr. Cetylphosphoric acid solution decanted.
  • the ethyl group in the ethyl phosphoric acid above mentioned may be hydrolyzed off to form the metal salt of the monoalkylorthophosphoric acid, i. e., the salt of RHQPO.
  • This type of operation is not limited to the alkyl derivatives but includes arylethylphosphoric acid, alkarylethylphosphoric acid, aralkylethylphosphoric acid and ethylphosphoric acids containing a cyclic nonbenzenoid group.
  • the metal salts of the various substituted oxy acids of phosphorus may be conveniently prepared by reacting the acid with sodium hydrox- Product was hydrolyzed 6. ide or potassium hydroxide and then precipitating the desired metal salt from the solution of the sodium or potassium salt by the addition of the appropriate metal ion.
  • the salt may also be prepared by the direct neutralization of the acid as, for example, with lime where the calcium salt is to be obtained.
  • Basic aluminum salts prepared by the precipitation method are preferred by reason of their low corrosivity to alloy bearing metals although the so-called normal salts are not precluded. It is also preferred to maintain the amount of coprecipitated alkali metal salt in the heavy metal compounds at a minimum because the alkali metal salts decrease the stability of the oil solution in the presence of water.
  • the calcium salts may also be prepared in the nonaqueous environment by the reaction of calcium carbide with the free substituted acids of phosphorus.
  • the aluminum salts may also be prepared in an environment substantially free of water by the reaction of aluminum chloride with the free substituted acids of phosphorus.
  • aluminum salts have properties difierent from the unique properties possessed by the compounded oils of this invention, data from extensive tests are given in Table 2.
  • anyl phosphate Aluminum dHamyl- 1.0 3.0 Fair 0.5 2.0 131 Amylphenol+P10 Do.
  • phenyl) phosphate luminum di-stearoglyc- 0.7 2.0 .do Glyceryldistearate+P2O +ether
  • the wear tests were carried out in a Weeks machine comprising a /2 inch steel ball pressed against a 1% inch steel cylinder with a force of 40 Has, the cylinder dipping in the oil to be tested and rotating at 600 R. P. M.
  • the duration of the test was sixteen hours and the wear rate determined by measuring the amount of metal removed from the ball.
  • the lubricant was maintained at approximately 300 F. as indicated.
  • the corrosion tests were carried out in the following manner: Glass tubes 2 inches in diameter and 20 inches long were immersed in an oil bath, the temperature of which was automatically controlled to within i1 F. of the test temperature which was 300 F. Approximately 300 cc. of oil under the test was placed in each tube and air was bubbled through it at the rate of liters per hour. Strips of the difierent types of bearing metals were cut to size and placed in the oils; in most cases the copper-lead mixture and cadmium-silver bearing alloys were tested simultaneously in the same sample of oil. The weight loss of each strip was recorded. Before weighing, each strip was washed in petroleum ether and carefully wiped with a soft cotton cloth. The duration of the test was 72 hours.
  • the compounding agents herein disclosed mal have one or more advantages, depending upon the particular compound selected, the proportion utilized, and the environment which the lubricating oil is to encounter. It should be observed, for example, that even though a compounded oil may be somewhat corrosive to copper-lead or cadmium-silver bearing metals, Babbitt bearings are little if at all affected by such corrosive action.
  • compounded oils which may not be particularly desirable for lubrication of copper-lead or cadmium-silver bearings may be highly useful and extremely advantageous in conjunction with the operation of internal combustion engines having bearings 01' Babbitt or other corrosive-resistant bearing metals.
  • the present invention in its broader aspects is therefore not limited to the use of a particular compound having all or the greatest number of advantages, but embraces various of the less advantageous addition agents which will find utility in particular applications where all the possible improvement in properties may not be required or where the standard of performance may not be so high.
  • polyvalent metal salts of substituted oxy acids of pentavalent phosphorus containing more than twelve carbon atoms in the molecule and preferably containing an alkyl or alkaryl substituent should be utilized. It is to be understood that by polyvalent metal salts used in the above connection the alkaline earth metals are included.
  • a moderately acid refined Western naphthenic base oil is the preferred oil stock used as a base for the compounded lubricants involved herein.
  • the compounding ingredients appear to function more efiiciently in such a base oil than in a highly paraflinic oil stock or a highly refined Western oil.
  • the invention is not limited to any particular base stock since advantages herein disclosed may be obtained at least to some degree with various oil stocks, the selection of which will be determined by conditions and service which the compounded lubricant is to encounter.
  • the proportion of metal salts of substituted oxy acids of phosphorus added to mineral lubricating oils may vary widely depending upon the uses involved and the properties desired. As little as 0.05% by weight of the compound gives measurable improvements, particularly as respects the color of the compounded oil after use in internal combustion engines. From approximately 0.25 to approximately 2% of the compound may be added to lubricants where ability to inhibit piston ring sticking comprises the principal property desired. Solutions containing more than 2% of the compounds in mineral oil may be utilized for the purpose of preparing lubricating greases and concentrates capable of dilution with lubricating oils and the like. Such higher concentrations comprise a convenient method of handling the compounds and may be used as addition agents for lubricants in general as well as for other purposes.
  • the metal salts of this invention may be added to hydrocarbon oils containing other compounding ingredients such as pour point depressors, oiliness agents, extreme pressure addition agents, blooming agents, compounds for enhancing the viscosity index of the hydrocarbon oil, corrosion inhibitors, color stabilizers, etc.
  • the invention in its broader aspects embraces mineral hydrocarbon oils containing, in addition to metal salts of the substituted acids of phosphorus, thickening agents and/or metal soaps in grease-forming proportions or in amounts insufficient to form greases, as in the case of mineral castor machine oils or other compounded liquid lubricants.
  • An aluminum salt of a phosphoric acid ester containing at least one alkyl aryl group and a total of 5 to 16 saturated carbon atoms in the alkyl radicals of said alkyl aryl groups.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Molecular Biology (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Lubricants (AREA)
  • Sliding-Contact Bearings (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
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US374078A 1938-10-04 1941-01-11 Compounded mineral oil Expired - Lifetime US2416985A (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
BE436573D BE436573A (no) 1938-10-04
NL54880D NL54880C (no) 1938-10-04
US242292A US2228671A (en) 1938-10-04 1938-11-25 Compounded mineral oil
CH221931D CH221931A (de) 1938-10-04 1939-09-30 Hitzebeständiges Kohlenwasserstofföl.
FR860580D FR860580A (fr) 1938-10-04 1939-10-02 Produit d'huile minérale
GB27128/39A GB537816A (en) 1938-10-04 1939-10-03 Hydrocarbon lubricating oil compositions
GB30163/39A GB538474A (en) 1938-10-04 1939-11-15 Compounded mineral oil
GB30164/39A GB539293A (en) 1938-10-04 1939-11-15 Compounded mineral oil
NL95973A NL60510C (no) 1938-10-04 1939-11-21
CH222547D CH222547A (de) 1938-10-04 1939-11-23 Hitzebeständiges Kohlenwasserstofföl.
US374078A US2416985A (en) 1938-10-04 1941-01-11 Compounded mineral oil
US374241A US2321804A (en) 1938-10-04 1941-01-13 Compounded mineral oil
US471276A US2382043A (en) 1938-10-04 1943-01-04 Compounded mineral oil

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US221931XA 1938-10-04 1938-10-04
US241648A US2228659A (en) 1938-11-21 1938-11-21 Compounded mineral oil
US374078A US2416985A (en) 1938-10-04 1941-01-11 Compounded mineral oil
US374241A US2321804A (en) 1938-10-04 1941-01-13 Compounded mineral oil
US471276A US2382043A (en) 1938-10-04 1943-01-04 Compounded mineral oil

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US (3) US2416985A (no)
BE (1) BE436573A (no)
CH (2) CH221931A (no)
FR (1) FR860580A (no)
GB (3) GB537816A (no)
NL (2) NL60510C (no)

Cited By (7)

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US2630442A (en) * 1949-05-21 1953-03-03 Metal & Thermit Corp Organotin phosphate esters
US2733184A (en) * 1956-01-31 Inject able penicillin repository prep ar a-
US2885417A (en) * 1955-11-10 1959-05-05 Bohme Fettchemie Gmbh Organic complex salts of polyvalent metals and methods of producing the same
US3488368A (en) * 1967-01-30 1970-01-06 Geigy Chem Corp Metal derivatives of alkylhydroxyphenylalkylphosphinic acids
US3491133A (en) * 1964-03-06 1970-01-20 Cities Service Res & Dev Co Metal organo phosphates and amine salts thereof
US3494949A (en) * 1967-01-03 1970-02-10 Dow Chemical Co Aluminum salts of alkyl orthophosphates
US4163018A (en) * 1976-12-18 1979-07-31 Sakai Chemical Industry Company, Ltd. Process for preparing metal salts of alkyl phosphates

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US2982727A (en) * 1957-12-31 1961-05-02 Exxon Research Engineering Co Lubricants containing salts and esters of oxygen-containing acids of phosphorus
NL266093A (no) * 1960-06-15
BE469342A (no) * 1961-01-23
US3213020A (en) * 1963-03-11 1965-10-19 Lubrizol Corp Lubricants containing metal phosphinothioate-epoxide reaction products
US3481717A (en) * 1968-10-22 1969-12-02 Sinclair Research Inc Gasoline composition
US4321424A (en) * 1978-03-31 1982-03-23 Rte Corporation Hydrocarbon electrical insulation oil containing tri-cresyl phosphate to increase water retention capability
US4200540A (en) * 1978-04-20 1980-04-29 Halliburton Company Method for fracturing subterranean formations
US4298723A (en) 1978-09-26 1981-11-03 Occidental Research Corporation Layered or amorphous acyclic organometallic inorganic polymers
EP0010857B1 (en) * 1978-09-26 1982-10-20 Occidental Research Corporation Layered or amorphous organometallic inorganic polymers and their use
US4487922A (en) * 1979-07-24 1984-12-11 Occidental Research Corp. Layered organophosphorous inorganic polymers containing cyclic groups
US4210542A (en) * 1978-12-01 1980-07-01 Gulf Research And Development Company Multicomponent stabilized hydraulic fluid
US4390690A (en) 1979-07-24 1983-06-28 Occidental Research Corp. Layered organophosphorous inorganic polymers containing oxygen bonded to carbon
US4429111A (en) 1979-07-24 1984-01-31 Occidental Research Corporation Layered organophosphorus inorganic polymers containing mixed functional groups
US4299943A (en) 1980-03-25 1981-11-10 Occidental Research Corporation Nonaqueous preparation of layered or amorphous organometallic inorganic polymers
US5059335A (en) * 1989-02-08 1991-10-22 The Lubrizol Corporation Lubricants containing salts of hydroxyalkane phosphonic acids
WO2000037591A1 (en) * 1998-12-23 2000-06-29 Rhodia Inc. Phosphate ester compositions in a weight ratio greater than 1:1 monoalkyl to dialkyl phosphate used as lubricant additives

Non-Patent Citations (1)

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2733184A (en) * 1956-01-31 Inject able penicillin repository prep ar a-
US2630442A (en) * 1949-05-21 1953-03-03 Metal & Thermit Corp Organotin phosphate esters
US2885417A (en) * 1955-11-10 1959-05-05 Bohme Fettchemie Gmbh Organic complex salts of polyvalent metals and methods of producing the same
US3491133A (en) * 1964-03-06 1970-01-20 Cities Service Res & Dev Co Metal organo phosphates and amine salts thereof
US3494949A (en) * 1967-01-03 1970-02-10 Dow Chemical Co Aluminum salts of alkyl orthophosphates
US3488368A (en) * 1967-01-30 1970-01-06 Geigy Chem Corp Metal derivatives of alkylhydroxyphenylalkylphosphinic acids
US4163018A (en) * 1976-12-18 1979-07-31 Sakai Chemical Industry Company, Ltd. Process for preparing metal salts of alkyl phosphates

Also Published As

Publication number Publication date
FR860580A (fr) 1941-01-18
GB538474A (en) 1941-08-06
NL60510C (no) 1947-12-16
GB539293A (en) 1941-09-04
US2321804A (en) 1943-06-15
NL54880C (no)
GB537816A (en) 1941-07-08
US2382043A (en) 1945-08-14
CH222547A (de) 1942-07-31
CH221931A (de) 1942-06-30
BE436573A (no)

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