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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • 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
  • C10L1/1835—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom having at least two hydroxy substituted non condensed benzene rings
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/13—Phenols; Phenolates
• • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/103—Liquid carbonaceous fuels containing additives stabilisation of anti-knock agents
• • 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
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
  • C11B5/00—Preserving by using additives, e.g. anti-oxidants
  • C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
  • C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D9/00—Compositions of detergents based essentially on soap
  • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
  • C11D9/045—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps containing substances which prevent the deterioration of soaps, e.g. light or heat stabilisers or antioxidants
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D9/00—Compositions of detergents based essentially on soap
  • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
  • C11D9/22—Organic compounds, e.g. vitamins
  • C11D9/26—Organic compounds, e.g. vitamins containing oxygen
• • 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
  • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring

Definitions

• inhibitors are substituted dihydroxydiphenyls having the general configuration n a R a H 011 wherein one R. attached to each pheny radical is any alkyl group, preferably an lkyl group having alkylated phenols having alkyl groups attached to the two carbon atoms adjacent to that linking the phenolic hydroxyl group.
• Such alkylated phenols have the general configuration R 1 a a wherein R1, R2, R3 and R4 are dissimilar alkyl groups and each phenyl radical contains at least one primary or secondary alkyl group.
• the symmetrical type of inhibitors represented by Formula 1 above may be prepared by the oxi; dation of a, single 2,6-dialkyl phenol wherein the alkyl groups are identical groups of primary or secondary configuration.
• Such diphenyl derivatives include 3,5,3,5-tetramethyl-4,4dihydroxydiphenyl, 3,5,3',5' tetraethyl 4,4 dihydroxydiphenyl, 3,5,3',5' tetrapropyl 4,4 dihydroxydiphenyl, 3,5,3,5-tetraamyl 4,4 dihydroxydiphenyl, 3,5.3',5 tetrahexyl 4,4 dihydroxydiphenyl, 3,5,3',5 tetraheptyI-4,4' dihydroxydi- :phenyl, 3,5,3',5'-tetraoctyl-4,4-dihydroxydiphenyl, 3,5,3,5-tetranonyl 4,4 dihydroxydiphenyl, 3,5.3 ',
• Inhibitors having the general configuration of Formula 2 above may be prepared by the simul-' taneous oxidation of two 2,6-dialkyl phenols, each having at least one alkyl group of primary or sec-. ondary configuration, one of which phenols has dissimilar alkyl groups, the other of which has alkyl groups which are both identical with one of said groups of the first phenol.
• This type of 3 v inhibitor is illustrated by such diphenyl derivatives as 3,5',5'-trimethy1-5-ethyl-4,4-clihydroxydiphenyl, 3,3',5-triethyl-5-methyl-4-4'-dihydroxydiphenyl,
• Inhibitors of this category may be the simultaneous oxidation of two symmetrical Prepared y the Oxidation Of a single unsymmetzsdialky ⁇ phenols the alkyl groups of one phenol rical 3,5-d1alkyl phenol having at least one alkyl differing from those of the other phenol but each gm?!) of primary or Secondary configuration phenol having at least one alkyl group of primary hibltof's of thls type are or secondary configuration.
• Inhibitors having 3,3'-dimethy1-5,5'-d yl- 3'dr0 y P this type of configuration include y 1 i 3,5-dimethyl-3 5'- iethyl-4,4'-dihydroxydiphenihgifs l dflsopmpy 4,4 -dyhydmxydi y], I r 3,5-diethyl-3',5'-dipropyl-4,4'-dihydroxydiphen 'i gif f methyl dflydmxm yl, r r I 3,5-diisopropyl-3,5'-dimethyl-4,4 dihydroxydi- 1 21 3 buty] methyl 'dihydxoxydl phenyl, 3,5-di-tert-butyl-3',5'-diethyl-4,4' dihydroxydi-- methyl d-mydmxydlphen phenyl,
• alkyl inhibitors having the general configuration of groups of the first dlfiermfg from those of the present invention are effective in relatively second but each phenol having at least one alkyl Small amounts; usually from about 00 to group of primary or secondary, configuration.
• oleaginous materials such as benzene, turpentine, corn oil, cottonseed oil; animal oils such as neats-foot oil and lanolin; fish oils such as sperm oils; synthetic cellulose derivatives such as ethyl cellulose, cellulose acetate, hydroxyethyl cellulose, carboxymethyl cellulose and cellulose nitrate; polymers of unsaturated materials, such as acrylic acid ester polymers, methacrylate polymers, polyvinyl compounds, polystyrene;- fats, oils and soaps; aromatic amines, dienes, terpenes and other naval stores.
• the statements as to properties and proportions as discussed hereinbefore in connection with cracked gasoline apply here as well.
• EXAMPLE III A leaded aviation gasoline was tested for stability as described in Example 1, above. It had an induction period of minutes. Two samples of this gasoline were inhibited with 1 and 2 mg. 3,5,3 ,5 -tetramethyl-4,4' -dihydroxydiphenyl of gasoline per 100 cc. respectively, and then tested for stability. The samples had induction periods of 400 and 4'70 minutes.
• a stable cracked gasoline composition comradical is a primary alkyl radical having from .one to twelve carbon atoms.
• a leaded aviation gasoline stabilized by the addition thereto of a small amount of 3,5,3,5',-tetramethyl-4,4'-dihydroxydiphenyi.
• a highly refined white oil stabilized by the addition thereto of a small amount of 3,3'-dimethyl-5,5'-di tert butyl 4,4 dihydroxydiphenyl.

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• Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Life Sciences & Earth Sciences (AREA)
• Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• General Chemical & Material Sciences (AREA)
• Emergency Medicine (AREA)
• Polymers & Plastics (AREA)
• Medicinal Chemistry (AREA)
• Biochemistry (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Lubricants (AREA)
• Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Priority Applications (4)

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Cited By (20)

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Citations (1)

• 0
  • FR FR959564D patent/FR959564A/fr not_active Expired
  • NL NL66455D patent/NL66455C/xx active
• 1947
  • 1947-01-25 US US724470A patent/US2479948A/en not_active Expired - Lifetime
  • 1947-12-24 GB GB34154/47A patent/GB646952A/en not_active Expired

Patent Citations (1)

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