GB794380A - Improved oils - Google Patents
Improved oilsInfo
- Publication number
- GB794380A GB794380A GB3668/56A GB366856A GB794380A GB 794380 A GB794380 A GB 794380A GB 3668/56 A GB3668/56 A GB 3668/56A GB 366856 A GB366856 A GB 366856A GB 794380 A GB794380 A GB 794380A
- Authority
- GB
- United Kingdom
- Prior art keywords
- boronic
- borinic
- acids
- acid
- oils
- 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
Links
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
- C10L1/30—Organic compounds compounds not mentioned before (complexes)
- C10L1/301—Organic compounds compounds not mentioned before (complexes) derived from metals
- C10L1/303—Organic compounds compounds not mentioned before (complexes) derived from metals boron 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
- 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
- C10M2207/28—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
- C10M2207/34—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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/40—Fatty vegetable or animal oils
-
- 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
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
-
- 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
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
- C10M2215/065—Phenyl-Naphthyl amines
-
- 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
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/066—Arylene diamines
-
- 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
- C10M2227/08—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 having metal-to-carbon bonds
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/06—Groups 3 or 13
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/10—Groups 5 or 15
-
- 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
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
- F02B3/00—Engines characterised by air compression and subsequent fuel addition
- F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition
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)
- Lubricants (AREA)
Abstract
Alkanolamine esters of boronic acids, R1B(OH)2, and borinic acids, R1,R2,BOH are added to fuel and lubricating oils (see Group III). The groups R1 and R2 contain at least three carbon atoms and may be aliphatic, cycloaliphatic, aromatic or heterocyclic and either may contain one or more substituents such as alkoxy, esterified carboxyl, hydroxyl, amino, nitrile, nitro, or boromic or borinic acid groups or halogen atoms. Preferred acids are benzyl, phenyl and tolyl boronic and dibenzyl, diphenyl and ditolyl borinic acids and phenylene-1,4- and naphthalene-1,4-diboronic acids. Suitable alkanolamines are mono-, di-, and triethanolamine, the amino-propyl alcohols and their N-dimethyl and N-diethyl derivatives and the amino butyl alcohols. Particularly preferred alkanolamines are N-hexyl, N-decyl, N-dodecyl and N-octadecyl ethanolamines and N-hexyl and N-octadecyl diethanolamines. The esters may be prepared by the azeotropic esterification of the acid or its anhydride with the alkanolamine in molar proportions in the presence of a suitable water entrainer which may also act as solvent, e.g. benzene or toluene. In examples, the preparation is described of (i) 3-azapentamethylene phenylbozonate from phenylboronic acid and diethanolamine in toluene solution; (ii) bis-(2-aminoethyl) phenylboronate from phenylboronic acid and ethanolamine in benzene solution; (iii) 2-aminoethyl diphenylborinate from diphenylborinic acid and ethanolamine in methylated spirits solution; (iv) N - hexyl - 3 - azapentamethylene phenylboronate from N-hexyl diethanolamine and phenylboronic acid in benzene solution, and (v) an N-tertiary alkyl ethanolamine ester of diphenyl borinic acid in xylene solution.ALSO:Oil compositions comprise a major proportion of an oil and a minor proportion of an ester of an alkanolamine and a boronic or borinic acid containing a group having at least three carbon atoms attached to the boron atom by a carbon to boron linkage. The oil may be of any type, e.g. hydrocarbon fuel, lubricating, and electrical oils, fatty oils and synthetic oils. Examples of suitable oils include straight-run, reformed, cracked or polymerized gasolines, or blends of gasolines with one another or with volatile alcohols or ethers, benzene, mixtures of aromatic hydrocarbons, such as benzene and toluene, naphthas, aviation turbine fuels, kerosines, diesel fuels, gas oils, or mixtures of two or more of these fuels; mineral lubricating oils, fatty oils and synthetic lubricating oils, e.g. polymerized olefines, polyoxyalkylene compounds, silicones and esters such as di-(2-ethyl hexyl) sebacate and trioctyl phosphate. Suitable alkanolamines are mono-, di-, and triethanolamine, 2-aminopropyl alcohol, 3-aminopropyl alcohol and its N-dimethyl and N-diethyl derivatives and the amino butyl alcohols, the preferred compounds being the N-alkyl (especially C6-24 alkyl) derivatives of mono- and dialkanolamines, e.g. N-hexyl mono- and diethanolamine, N-decyl ethanolamine, N-dodecyl ethanolamine, N-octadecyl ethanolamine and N-octadecyl diethanolamine. The boron acids have the general formula <FORM:0794380/III/1> when R1 is a group having at least 3 carbon atoms and R2 is an organic group, both being attached to the boron atom by a carbon to boron linkage. R1 and R2 may be aliphatic, cycloaliphatic, aromatic or heterocyclic groups and either may contain one or more substituents such as methoxy, ethoxy, esterified carboxyl, hydroxyl, amino, nitrile, nitro, boronic or borinic acid groups or halogen atoms. Examples of suitable boronic and borinic acids are those where R1 and/or R2 are propyl, butyl, octyl, decyl, hexadecyl, octadecyl, heptadecenyl, benzyl, phenyl, methyl phenyl, hydroxyphenyl, methoxyphenyl, dimethoxyphenyl, chlorophenyl, methyl chlorophenyl, nitrophenyl, benzoylaminophenyl, naphthyl, methylnaphthyl, methoxynaphthyl, chloronaphthyl, nitronaphthyl, aminonaphthyl, tolyl, fluorenyl, anthryl, phenanthryl, pyridyl, picolyl, pyrrolyl, indolyl, carbazolyl, furyl, benzofuranyl, or dibenzofuranyl, the aromatic boronic and borinic acids such as benzyl boronic, dibenzyl borinic, phenyl boronic, diphenyl borinic, tolyl boronic and ditolyl borinic acids being preferred. Arylene di-boronic or di-borinic acids may also be used, e.g. phenylene- or naphthalene-1,4-diboronic acid. Examples of suitable esters of the boron acids are those derived by esterifying diethanolamine with phenylboronic, p-tolyl boronic, p-methoxyphenylboronic, p-bromophenyl boronic or m-nitrophenyl boronic acid. Details are given of the preparation (see Group IV (b)) of : (i) 3-azapentamethylene phenylboronate; (ii) bis - (2 - aminoethyl) phenylboronate; (iii) 2 - aminoethyl diphenylborinate; (iv) N-hexyl-3-azapentamethylene phenylboronate; and (v) the diphenyl borinic ester of a commercial N-t-alkyl ethanolamine. Optional ingredients are lead tetralkyls (ethyl and/or methyl) and antioxidants such as dimethyl-6-t-butyl phenol, 2,6 - di - t - butyl - 4 - methyl phenol, N - phenylalpha - naphthylamine and N,N1 - dibutyl - p - phenylene diamine. In examples a petroleum hydrocarbon fraction of boiling range 80-100 DEG C. is treated with above-mentioned esters (iv) and (v).
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3668/56A GB794380A (en) | 1956-02-06 | 1956-02-06 | Improved oils |
FR1172224D FR1172224A (en) | 1956-02-06 | 1957-02-06 | Oil composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3668/56A GB794380A (en) | 1956-02-06 | 1956-02-06 | Improved oils |
Publications (1)
Publication Number | Publication Date |
---|---|
GB794380A true GB794380A (en) | 1958-04-30 |
Family
ID=9762688
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3668/56A Expired GB794380A (en) | 1956-02-06 | 1956-02-06 | Improved oils |
Country Status (2)
Country | Link |
---|---|
FR (1) | FR1172224A (en) |
GB (1) | GB794380A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1170192B (en) * | 1959-03-20 | 1964-05-14 | Ethyl Corp | Fuels for carburettor engines |
US4335005A (en) * | 1980-09-11 | 1982-06-15 | Mobil Oil Corporation | Lubricant compositions containing metal antifatigue additives |
CN114774181A (en) * | 2022-05-05 | 2022-07-22 | 张跃富 | Extreme pressure antiwear additive, extreme pressure antiwear lubricating oil and preparation method thereof |
-
1956
- 1956-02-06 GB GB3668/56A patent/GB794380A/en not_active Expired
-
1957
- 1957-02-06 FR FR1172224D patent/FR1172224A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1170192B (en) * | 1959-03-20 | 1964-05-14 | Ethyl Corp | Fuels for carburettor engines |
US4335005A (en) * | 1980-09-11 | 1982-06-15 | Mobil Oil Corporation | Lubricant compositions containing metal antifatigue additives |
CN114774181A (en) * | 2022-05-05 | 2022-07-22 | 张跃富 | Extreme pressure antiwear additive, extreme pressure antiwear lubricating oil and preparation method thereof |
Also Published As
Publication number | Publication date |
---|---|
FR1172224A (en) | 1959-02-06 |
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