Classifications

• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
  • C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
  • C10L1/1832—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom mono-hydroxy
• • 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
  • C10M2207/02—Hydroxy compounds
  • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
  • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
• • 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
  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
  • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
  • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
• • 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
  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
  • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
• • 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
  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/22—Acids obtained from polymerised unsaturated 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/08—Amides
• • 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/08—Amides
  • C10M2215/082—Amides containing hydroxyl groups; Alkoxylated 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/086—Imides
• • 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/14—Containing carbon-to-nitrogen double bounds, e.g. guanidines, hydrazones, semicarbazones
• • 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/28—Amides; Imides
• • 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
  • C10N2040/135—Steam engines or 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
  • C10N2040/14—Electric or magnetic purposes
  • C10N2040/16—Dielectric; Insulating oil or insulators
• • 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
  • C10N2040/14—Electric or magnetic purposes
  • C10N2040/17—Electric or magnetic purposes for electric contacts

Definitions

• This invention relates to the production of mineral oil compositions having properties which render them especially suitable for use as lubricants for turbines and as dielectrics for electrical equipment such as transformers. It also deals with lubricating oils containing small amounts of an addition agent which renders the oil highly resistant to oxidation and gum or slud e formation. More particularly, it deals with the use of 2,4-dimethyl-6-tertiary octyl phenol for stabilizing turbine oils against oxidation and gum formation.
• 2,4-dimethyl-6- tertiary octyl phenol possesses outstanding characteristics which distinguish this compound from related tri-alkylated phenols for use in the particular mineral oil blends herein contemplated. These outstanding characteristics are improved oxidation stability and reduced tendency to disperse iron rust in the compounded oil.
• metallic iron and/or copper which is always used in the construction of-turbine oiling systems, has a catalytic efiect on oil oxidation.
• a good turbine oil must therefore be highly resistant to oxidation in the presence of iron and copper, must not tend to disperse metallic oxidation catalysts throughout the oil and must maintain a reasonably high interfacial tension against water during use.
• Turbine oils having the above properties can be produced from well refined lubricating oils of the proper viscosity range, which may be about these lubricating oils about .01% to 1% of 2,4- dimethyl-S-tertiary octyl phenol.
• the phenols which may be alkylated to form the useful tertiary octyl antioxidant are either (1) pure 2,4-dimethyl phenol, or (2) a narrow boilin liquid phenol fraction having an A. S. T. M. 5% boiling point of 206-211 (2., a 50% boiling point of 210-212 C. and a 95% boiling point of 211-216 C. Preferably the 5% boiling point is not lower than 209C. and the 95% point not above 213 C.
• Such fraction normally contains about 60% of 2,4-dimethyl phenol, the most important of the remaining phenols being about 25% 2,5-dimethyl phenol.
• Alkylation may be carried out by using as alkylating compound tertiary base octylene such as di-isobutylene or so-called hot acid octylenes; or tertiary octyl chloride, or the corresponding alcohol, or di-tertiary octyl ether.
• tertiary base octylene such as di-isobutylene or so-called hot acid octylenes
• tertiary octyl chloride or the corresponding alcohol, or di-tertiary octyl ether.
• Catalysts or condensing agents useful in alkyating the phenols are the inorganic poly-oxy acids such as sulfuric acid, sulfonic acids, phosphoric acid, P205, etc.; Friedel-Craft catalysts such as aluminum chloride, zinc chloride, acid zinc sulfate, tin tetrachloride, ferric chloride, boron trichloride, boron fluoride; complex compounds of Friedel-Crafts catalysts such as halides of Al, B, Fe, Sn, Sb and W, with inactive halide salts as NaCl, HgClz, AgCl, etc., or dissolved in organic liquids such as nitrobenzene, acetone, acetophenone, benzoyl chloride, di-ethyl sulfone,
• reaction may be carried out in dilution of inert solvents for the alkyl phenols such as carbon dlsulfide, nitrobenzene, parafllns free of reactive tertiary atoms, etc.-
• inert solvents for the alkyl phenols such as carbon dlsulfide, nitrobenzene, parafllns free of reactive tertiary atoms, etc.
• Temperatures suitable for our process may vary with the catalyst but usually are between about 0 and 100 C. and the quantities of catalysts may vary from very small amounts to those equalling or slightly exceeding the amount of alkyl phenols present.
• the following example illustrates one method of preparation of the 2,4-dimethyl-6-tertiary octyl phenol:
• Starting material was xylenol fraction boiling at about 211 C. and containing 82.5% 2,4-dimethyl phenol and 17.5% 2,5-dimethyl phenol, the latter being relatively unreactive under the conditions of this reaction.
• To the xylenol fraction was added tertiary octyl chloride. ferric chloride and carbon disuliide. The mixture was refluxed for 8 hours. Carbon disulflde was removed under vacuum. The high boiling residue dissolved in benzene and the solution was washed with water to remove ferric chloride. The benzene was distilled oil!
• 2,4-dimethyl-6-tertiary octyl phenol may be used in combination with other secondary additivessuch as corrosion inhibitors, e. g. allwl succinic acids, aromatic imino alpha di-carboxylic acids, etc., E.'P. compounds,- blooming agents, etc.
• corrosion inhibitors e. g. allwl succinic acids, aromatic imino alpha di-carboxylic acids, etc., E.'P. compounds,- blooming agents, etc.
• a well-refined turbine oil oi. 150 S. S. U. viscosity at 100 F. tree from added oxidation inhibitors was divided into three portions. To-one portion was added 2% by weight of 2,4-dimethyl- I 'B-tertiary butyl phenol. To another portion was [the top of the 3 oil layer. oxidation were set up in a water bath to maintain the temperature of the oil at (2.11. Omen was then bubbled through each tube at the rate of 3 liters per hour. The passage or oxygen was maintained until the oil in each tube darkened and its neutralization number had reached a value of 5. V i t V Results were as iollowsz I claim as my invention:
• a mineral oil composition comprising turbine oil normally susceptible to oxidation under conditions encountered in use and a small amount of 2,4-dimethyl-6-tertiary octyl phenol suillcient to retard oxidation.
• Turbine 011 comprising predominantly a refined mineral lubricating oil having a viscosity at F. or 75 to 750 Bay. Univ. Seconds, and containing dissolved 415% to 2% of 2,4-dimethyld-tertiary octyl phenol.
• Turbine oil comprising predominantly a refined mineral lubricating oil having a viscosity at 100 I". of 7,5 to 750 Bay. Univ. Seconds, and containing dissolved .05% to 3% of 2,4-dlmethyld-tertiary'octyl phenol.
• a refined hydrocarbon oil subject to oxidation containing as an active anti-oxidant 2,4- dimethyl-B-tertiary octyl phenol.

Landscapes

• Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Health & Medical Sciences (AREA)
• Emergency Medicine (AREA)
• Lubricants (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Priority Applications (3)

Applications Claiming Priority (1)

Publications (1)

Family

ID=23772044

Family Applications (1)

Country Status (3)

Cited By (10)

• 0
  • NL NL66833D patent/NL66833C/xx active
• 1942
  • 1942-06-08 US US446291A patent/US2351347A/en not_active Expired - Lifetime
• 1943
  • 1943-09-06 GB GB14581/43A patent/GB572012A/en not_active Expired

Also Published As

Similar Documents