Classifications

• • 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
  • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
• • 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
  • 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
  • C07F9/09—Esters of phosphoric acids
  • C07F9/12—Esters of phosphoric acids with hydroxyaryl 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
  • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
  • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
  • C10M2211/024—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
• • 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
  • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
  • C10M2211/06—Perfluorinated 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
  • 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
  • C10M2223/041—Triaryl phosphates
• • 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
  • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
  • C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
• • 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
  • C10N2040/08—Hydraulic fluids, e.g. brake-fluids

Definitions

• properties which are required for safe and satisfactory low temperature operation include a low pour point which permits a hydraulic fluid to operate at low temperature.
• Other important properties which are desirable in hydraulic fluids are a high viscosity and a flat viscosity temperature curve, that is, a high viscosity index which allows the fluid to remain operable over a wide range of temperatures.
• One of the vital properties which is required for hydraulic fluids which are to be utilized in either commercial industry and mining or military use is minimum flammability.
• Other desirable qualities for such products include a relatively high boiling point, low corrosion characteristics and low oxidation susceptibility.
• novel styrenated phenyl bis(isopropylphenyl) phosphates are suitable for use as hydraulic fluids having been found, surprisingly, to possess all the above described properties required for the successful utilization of such products.
• these phosphates have high viscosities in the range from about 800 to about I ,200 Saybolt Universal Seconds at 100 F. and have relatively high viscosity indices when compared to commercial fluids in this viscosity range. Further, they have pour points below F. and high autoignition temperatures in the range from about 900 to about 1,100" F.
• the phosphates employed in the process of the present invention are novel styrenated phenyl bis(isopropylphenyl) phosphates having the structure:
• n is a number greater than 0 and less than i
• m is a number from i to 2 inclusive.
• Steps (a) and (b) can be carried out sequentially or simultaneously. However, the sequential process is preferred because it allows for better control over the value of n, which value is essential to the hydraulic fluids of the present invention.
• the reaction of the present invention is conducted in the presence of a Lewis acid catalyst.
• Lewis acid catalyst is meant to designate those inorganic compounds which are strong electron pair acceptors. These compounds are well known in the art and are illustrated by the following: ferric, aluminum, zinc and magnesium chloride, molybdenum pentachloride, starinic tetrachloride and boron trifluoride,
• the Lewis acid catalyst is employed in amounts from about 0.1 to about 5.0 percent by weight of the entire reaction mixture and preferably in the range from about 0.05 to about 2 percent by weight.
• the styrenated phenols employed in making the hydraulic fluids of the present invention are commercially available as mixtures of a major portion of styrenated phenol, and minor portions of phenol and the di-styrenated phenols. They can also be synthesized by reacting styrene with phenol at elevated temperatures in the presence of various catalysts.
• the isopropylated phenols are also commercially available, normally as mixtures consisting of a major portion of ortho, meta and para isopropyl phenols; together with smaller portions of the 2,6-diisopropyl phenol, 2,4-diisopropyl phenol: triisopropyl phenol and phenol.
• the ratio of the isopropylphenyl moiety to the styrenated phenyl moiety must be maintained within certain limits in order to obtain hydraulic fluids having the desired properties mentioned above.
• This ratio should be greater than 2 to i, that is, n is a number less than 1, in order to get fluids having viscosities in the desired range of from about 900 to about 1,200 S.U.S. Therefore, less than 1 mole of the styrenated phenol or a styrenated phenol mixture should normally be employed per mole of phosphorus oxyhalide in step (a) and at least 2 moles of isopropyl phenol or of an isopropyl phenol mixture should be employed in step (b).
• the reaction temperature should be maintained in the range from about 20 to about 300 C. and preferably in the range from about to about 200 C.
• the reaction times are normally in the range from about 4 to about 20 hours; the shorter times being obtained when the higher temperatures are employed.
• the styrenated phenyl bis(isopropylphenyl) phosphate esters are characterized by having desirable and unusually high viscosities and viscosity indices. This is surprising since they have a large proportion of cyclic structures per molecule which would normally be expected to lower their viscosity indices as was stated above. Thus, one would expect the triaryl phosphate functional fluids having a base stock of the tricresyl and trixylyl phosphates to have higher viscosity indices than the styrenated phenyl bis(isopropylphenyl) phosphates of the present invention. However, the compounds of the present invention exhibit viscosity indices which are much higher than those of the triaryl phosphates.
• the styrenated triaryl phosphates used in the process of the present invention can be used individually or blended with anticorrosion agents, defoarners and various load bearing additives all of which are well described in the literature.
• the functional fluids of this invention can be mixed with less costly petroleum oils and/or polychloroaromatic compounds, particularly polychlorobenzenes and polychlorobiphenyls.
• the compounds used in the process of the present invention are deployed in a closed hydraulic system such as compressors, hydraulic lifts, deck edge elevators, brake systems, basic oxygen furnaces, die casting equipment, leveling devices or servo control units in such a manner that when pressure is applied to the phosphate at a specific point within the confines of the hydraulic system, the pressure will be transmitted to every other point along the hydraulic system by the phosphate.
• a closed hydraulic system such as compressors, hydraulic lifts, deck edge elevators, brake systems, basic oxygen furnaces, die casting equipment, leveling devices or servo control units
• EXAMPLE 1 A 2 liter Pyrex 3 neck reactor was fitted with a thermometer, condenser, dropping funnel and a magnetic stirrer. The condenser was connected by means of a Y tube to a nitrogen bleed system and an aqueous l-lCl trap. The reactor was charged with 163.4 grams of phosphorus oxychloride and 195 grams of a commercially available styrenated phenol which is composed of 21.4 percent phenol, 57.8 percent monostyrenated phenol, 15.3 percent di-styrenated phenol, and 5.3 percent tri-styrenated phenol. The system was bled with nitrogen gas while the contents of the reactor were stirred at a moderate speed.
• the temperature was gradually raised to 160 C. and maintained at that temperature until 1.9 moles of hydrogen chloride was collected in the aqueous trap.
• the reaction mixture was then transferred to 1 liter distilling flask and stripped of low boiling substituents at 187 C. (0.50 mm) for 1 hour.
• the crude product was added dropwise to a flask containing 500 milliliters of well agitated 1 percent caustic solution at 60 C. and stirred for 1 hour.
• the mixture was allowed to phase and then separated by means of a separatory funnel.
• the caustic wash was repeated 3 more times at 60 and then washed with a 1 percent solution of phosphoric acid.
• the product was then washed with water and azeotroped with 1 liter of benzene to dryness.
• the benzene was removed by distilling at 42 C. (200 mm).
• the cloudy product was filtered through a bed of Fullers Earth at 60-70 C.
• the product was then analyzed and the results
• Example 11 S.U.S. F. 1,029 1,087 NMR moles styraphenyl 1.0 1.0 per mole phosphate Acid No. mg. KOH/gm. 0.14 0.56 n 1.5571 1.5580 d 1.1 l 1.1 1
• Example 3 The process of Example 1 was repeated. The product was shown by NMR to contain approximately 0.7 styraphenyl groups per molecule. It was compared with a commercially available hydraulic fluid in the same viscosity range sold under the name of Fyrquel 1,000 by Stauffer Chemical Company of New York. The results of this comparison are contained in Table 11.
• the fluids employed in the present invention also perform favorably when tested in a Vickers 104 Vane Pump. During test runs, these fluids exhibit viscosity, color and neutralization characteristics which are equal to or superior to the com yorkally available hydraulic fluids tested.
• a process for the transmission of pressure in a hydraulic system which comprises deploying within said hydraulic system an efiective amount of a phosphate ester having the structure corresponding to the formula:
• n is a number greater than 0 and less than 1 and m is a number from 1 to 2 inclusive; and applying pressure to said phosphate ester at any point in said system so as to thereby transmit the thus applied pressure throughout said system through the medium of said phosphate.
• n is a number from about 0.5 to about 0.9 inclusive.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Biochemistry (AREA)
• General Health & Medical Sciences (AREA)
• Molecular Biology (AREA)
• Lubricants (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Applications Claiming Priority (1)

Publications (1)

Family

ID=21761723

Family Applications (1)

Country Status (7)

• 1970
  • 1970-02-24 US US13781A patent/US3674697A/en not_active Expired - Lifetime
• 1971
  • 1971-01-22 CA CA103,390A patent/CA962660A/en not_active Expired
  • 1971-02-05 NL NL7101568A patent/NL7101568A/xx unknown
  • 1971-02-19 FR FR7105773A patent/FR2081032B1/fr not_active Expired
  • 1971-02-23 DE DE19712108487 patent/DE2108487A1/de active Pending
  • 1971-02-23 BE BE763302A patent/BE763302A/xx unknown
  • 1971-04-19 GB GB2402071*A patent/GB1309020A/en not_active Expired

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