US3514402A - Synthetic lubricants containing trimethylol - alkane - di - ortho-silicic acid esters - Google Patents

Synthetic lubricants containing trimethylol - alkane - di - ortho-silicic acid esters Download PDF

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US3514402A
US3514402A US686293A US68629367A US3514402A US 3514402 A US3514402 A US 3514402A US 686293 A US686293 A US 686293A US 68629367 A US68629367 A US 68629367A US 3514402 A US3514402 A US 3514402A
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ester
esters
synthetic lubricants
acid esters
trimethylolpropane
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Herbert Gothel
Hans Feichtinger
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Ruhrchemie AG
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Ruhrchemie AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/04—Esters of silicic acids
    • 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
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108—Phenothiazine
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/02—Esters of silicic acids
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
    • 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
    • C10N2040/12—Gas-turbines
    • 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
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines

Definitions

  • Z is the ester residue of said carboxylic acid and R is hydrogen or a lower alkyl of about 1 to 6 carbon atoms, R is alkyl, R' is diethylene glycol-n-butyl ether residue, R and R may be the same or diiferent, and n is to 3.
  • Synthetic lubricants for turbine engines must possess a number of properties in order to be capable of heavy duty service undervarying operationg conditions. They must be on the one hand fiowable at 55 C., in order to allow low temperature starting of the oil pumps at great heights. They must also withstand temperatures of 400 C. and even higher, which temperatures are reached at hot points of the engine, without undergoing thermal or oxidative decomposition.
  • esters of polyvalent alcohols having a quaternary carbon atom as lubricants for jet power aircraft engines, as for instance neopentylglycol, trimethylolethane and trimethylolpropane (see, for instance, Ullmanns Enzyklopadie der ischen Chemie, vol. 15, 1964, p. 292 et seq.).
  • esters possess high thermal and oxidative stability, but their viscosity-temperatureresponsivity and their viscosity at low temperatures are unfavorable (see Table 1, esters A to D).
  • silicones as lubricants (see for instance Ullmann l.c., p. 295 et seq.). These compounds possess an excellent viscosity-temperature-responsivity, since they are stable at high temperatures and have low setting points, however, their lubricity is limited. It was attempted to overcome this drawback by the use of halogenated silicones, but these materials cannot be employed at high temperatures, since they are corrosive even at 260 C. (see Gunderson/ Hart, Synthetic Lubricants, p. 314).
  • Lubricants bases on orthosilicic and disilicic acid esters are described in Ullmann, l.c., p. 298 et seq. They also possess excellent viscosity-temperature-responsivity, but become easily hydrolized with formation of gels. Their oxidative stability is unsatisfactory (see Table II, esters 1 to 3), so that they must be stabilized by the addition of other substances. Furthermore, lubricating films of tetraalkyl-orthosilicic acid esters exhibit unsatisfactory load carrying capacities at mixed friction.
  • Another object of the invention is to provide fluid compositions suitable for use as lubricants in jet propulsion aircrafts.
  • liquid materials comprising di-orthosilicic acid esters of the formula wherein A represents a radical of an ester derived from a trimethylol-alkane containing a quaternary carbon atom and having up to about 10 carbon atoms, preferably a trimethylol-alkane, and a saturated carboxylic acid having about 3 to 20 carbon atoms corresponding to the structural formula:
  • Z is the ester residue of said carboxylic acid and R is hydrogen or a lower alkyl of about 1 to 6 carbon atoms
  • R represents an alkyl group having about 4 to 20 carbon atoms
  • R represents a n-butoxy-diethylene glycol ether radical
  • n has a value of 0 to 3 and wherein R and R may be the same or different, as lubricants in jet propulsion aircrafts.
  • liquid compositions of this invention may be used alone or admixed with other liquid materials, e.g., conventional fluid materials suitable for use as lubricants as well as with the conventional additive materials, i.e., antioxidants, etc.
  • di-orthosilicic acid esters wherein the A-groups are radicals of the monoester of trimethylolethane, trimethylolpropane or trimethylolbutane with pivalic acid, isobutyric acid or 6,5- dimethylbutyric acid constitute broadly preferred di-orthosilicic acid esters.
  • Di-orthosilicic acid esters wherein R represents alkyl radicals having about 7 to 20 carbon atoms are well suited.
  • the monoesters of polyvalent alcohols characterized by A in the formula given hereinbefore, can be obtained by reaction of one mole of the polyvalent alcohol and one mole of the carboxylic acid hereinbefore defined, at a temperature below about C. followed by distillative recovery of the ester thereby formed.
  • the starting materials for the R groups having about 7 to 20 carbon atoms may be derived from alcohols obtained by hydroformylation of straight chain olefins followed by hydrogenation.
  • di-orthosilicic acid esters according to the invention have hitherto not been described. They may be prepared 'by the conventional methods employed for the production of di-orthosilicic acid esters as known in the art, as for instance by reacting stoichiometric amounts of corresponding water-free alcohols, polyoxyalkylene glycols and monocarboxylic acid esters of the polyvalent alcohols with gaseous silicon tetrachloride as disclosed in German Pat. 1,142,855 or as discolsed in German patent applica- 3 tion R 32,696 IVb/ 12 0, German Auslegeschrift 1 180 359.
  • esters of the invention used in the comparison and listed in Table I are the following:
  • esters of the invention having molecular weights above 1000 boil at temperatures above 450 C. at 760 torr, above 250 C. at 1 torr and above 180 C. at 0.01 torr. Their flame points range above 260 C.
  • the viscosity-temperature-responsivity of the esters of the invention determined according to the viscosity index of Dean and Davis (DIN 51 563, see G. V6gtle, Lexikon der Schmleiterstechnik, Stuttgart, 1964) is low.
  • Diorthosilicic acid esters wherein A consists of a radical of a trimethylolethaneor trimethylolpropane-pivalic acidmono-ester distinguish themselves from esters with equal R-groups, but other acid components in the A-group by their lowest viscosity and their highest viscosity index.
  • the esters according to the invention exhibit outstanding low temperature characteristics.
  • the setting points set out in Table I depends on their viscosity and are not caused by solid deposits.
  • the thermal stability of the esters was determined by the following test:
  • the oxidative stability of the di-orthosilic acid esters according to the invention was evaluated in comparison with that of dibasic esters and orthosilicic acid esters known in the art.
  • Ester A is illustrative of lubricants which can be employed in the subsonic range. Those lubricants are distinguished by outstanding low temperature characteristics and favorable viscosity indices, but possess only low oxidative stability.
  • Ester B and ester D are typical for lubricants to be used in the supersonic range up to Mach 2.2. Their oxidative stability is good but their viscosity indices and low temperature characteristics are unsatisfactory.
  • the di-orthosilicic acid esters according to the invention possess the excellent low temperature characteristics as well as viscosity-temperature-responsivity as the ester A comparable therewith in combination with a good or even better oxidative stability as the illustrative esters B to D.
  • orthosilicic acid esters (esters 1 to 3 given as example) yield too high evaporation values at the oxidation test.
  • esters according to the invention are surprisingly heat-stable; no gel formation occurs by heating above 300 C. in the presence of air. They are also water-resistant.
  • the esters according to the invention exhibit further good lubricating action.
  • Differentiated numerical characteristics therefor were determined by the attrition test with the four-ball apparatus of Boerlage (Lexikon der Schmiertechnik, G. Vogtle, Franckhsche Verlags Stuttgart, Stuttgart, 1964) at 200 C. under a constant load of 40 kg. dependent upon the testing time (after 60, 120 and 180 minutes).
  • the four-ball apparatus was heated in an electrically heated metal bath.
  • the oils to be tested were inhibited against oxidation by addition of 1 percent by weight of phenothiazine.
  • the diameters of the scratches thereby obtained (mm.) were determined by microscopic inspection.
  • the esters according to the invention yielded the lowest attrition values after 60, 120 and 180 minutes. Further, the small rates of growth of the attrition values demonstrate the efficiency of the esters according to the invention as lubricants.
  • esters according to the invention can be admixed with other lubricants known in the art in any ratio whatever. Particularly, they are ad mixed with up to 75 percent other lubricants as for instance with mineral lubricating oils, carboxylic acid esters,
  • organosilicon compounds of various structures different from those of this invention, polyphenyl-ether-oils or with phosphoric acid esters. Due to their oxidative and thermal stability, lubricating power and viscosity characteristics, including their flowability at low temperatures, the esters according to the invention improve the properties of the added lubricants.
  • the heat-stable esters according to the invention can be used as desirable lubricating components for stabilized dibasic esters with quaternary carbon atoms whose viscosity indices alone are unsatisfactory.
  • Synthetic lubricants comprising diorthosilicic acid esters of the formula wherein A represents a radical selected from the group consisting of esters of trirnethylolalkanes having a quarternary carbon atom and comprising a total number of up to about 10 carbon atoms and at least one saturated monocarboxylic acid having about 3 to 20 carbon atoms corresponding to the structural formula:
  • Z is the ester residue of said acid and said monocarboxylic acid and R" is a member selected from the group consisting of hydrogen and alkyl having up to 6 carbon atoms, R represents alkyl groups having about 4 to 20 carbon atoms, R represents n-butoxy-diethyleneglycol-ether radical, and n is 0 to 3.
  • Synthetic lubricants according to claim 1 containing up to percent conventional lubricating oil.
  • Synthetic lubricants according to claim 1 containing at least one anti-oxidant.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US686293A 1966-12-01 1967-11-28 Synthetic lubricants containing trimethylol - alkane - di - ortho-silicic acid esters Expired - Lifetime US3514402A (en)

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DE (1) DE1594552B2 (ja)
GB (1) GB1210510A (ja)
NL (2) NL6716037A (ja)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3994948A (en) * 1973-09-25 1976-11-30 Castrol Limited Hydraulic fluids
US4013698A (en) * 1974-03-25 1977-03-22 Ciba-Geigy Corporation Polysiloxanes containing hydroxyl groups
US4093554A (en) * 1974-03-27 1978-06-06 Castrol Limited Hydraulic fluid compositions
US9592527B2 (en) 2007-04-05 2017-03-14 Ppg Architectural Finishes, Inc. Spray texture material compositions, systems, and methods with accelerated dry times

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2776307A (en) * 1953-12-30 1957-01-01 California Research Corp Polyglycol silicates
US2909551A (en) * 1956-08-20 1959-10-20 Hollingshead Corp Disiloxane ester ethers
US3029269A (en) * 1956-08-21 1962-04-10 California Research Corp Silicon esters
US3085104A (en) * 1953-04-30 1963-04-09 Exxon Research Engineering Co Silicon containing lubricating compositions
US3133111A (en) * 1961-04-07 1964-05-12 Union Carbide Corp Process for the transesterification of alkoxy-containing organosilicon compounds
US3218271A (en) * 1960-04-06 1965-11-16 Wong Robert Foamable novolac composition and cellular phenolic body produced by cure
US3287384A (en) * 1961-01-11 1966-11-22 Houghton & Co E F Ortho esters of aluminum, silicon or titanium with a metal soap of a hydroxy-fatty acid
US3336227A (en) * 1964-07-10 1967-08-15 Ruhrchemie Ag Polyalkylene glycol-diorthosilicic acid ester lubricants and power transmitting fluids
US3383315A (en) * 1964-09-11 1968-05-14 Ruhrchemie Ag Polyalkylene glycol-diorthosilicic acid ester lubricants and power transmitting fluids

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3085104A (en) * 1953-04-30 1963-04-09 Exxon Research Engineering Co Silicon containing lubricating compositions
US2776307A (en) * 1953-12-30 1957-01-01 California Research Corp Polyglycol silicates
US2909551A (en) * 1956-08-20 1959-10-20 Hollingshead Corp Disiloxane ester ethers
US3029269A (en) * 1956-08-21 1962-04-10 California Research Corp Silicon esters
US3218271A (en) * 1960-04-06 1965-11-16 Wong Robert Foamable novolac composition and cellular phenolic body produced by cure
US3287384A (en) * 1961-01-11 1966-11-22 Houghton & Co E F Ortho esters of aluminum, silicon or titanium with a metal soap of a hydroxy-fatty acid
US3133111A (en) * 1961-04-07 1964-05-12 Union Carbide Corp Process for the transesterification of alkoxy-containing organosilicon compounds
US3336227A (en) * 1964-07-10 1967-08-15 Ruhrchemie Ag Polyalkylene glycol-diorthosilicic acid ester lubricants and power transmitting fluids
US3383315A (en) * 1964-09-11 1968-05-14 Ruhrchemie Ag Polyalkylene glycol-diorthosilicic acid ester lubricants and power transmitting fluids

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3994948A (en) * 1973-09-25 1976-11-30 Castrol Limited Hydraulic fluids
US4013698A (en) * 1974-03-25 1977-03-22 Ciba-Geigy Corporation Polysiloxanes containing hydroxyl groups
US4093554A (en) * 1974-03-27 1978-06-06 Castrol Limited Hydraulic fluid compositions
US9592527B2 (en) 2007-04-05 2017-03-14 Ppg Architectural Finishes, Inc. Spray texture material compositions, systems, and methods with accelerated dry times

Also Published As

Publication number Publication date
DE1594552B2 (de) 1973-03-29
NL6716037A (ja) 1968-06-04
NL134718C (ja)
DE1594552A1 (de) 1970-12-03
GB1210510A (en) 1970-10-28

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