GB810087A - Alkyl arylstearates and process of producing same - Google Patents

Alkyl arylstearates and process of producing same

Info

Publication number
GB810087A
GB810087A GB34050/56A GB3405056A GB810087A GB 810087 A GB810087 A GB 810087A GB 34050/56 A GB34050/56 A GB 34050/56A GB 3405056 A GB3405056 A GB 3405056A GB 810087 A GB810087 A GB 810087A
Authority
GB
United Kingdom
Prior art keywords
acid
methyl
alkyl
ethylhexyl
butyl
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
Application number
GB34050/56A
Inventor
Jacques Artozoul
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IFP Energies Nouvelles IFPEN
Original Assignee
IFP Energies Nouvelles IFPEN
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by IFP Energies Nouvelles IFPEN filed Critical IFP Energies Nouvelles IFPEN
Publication of GB810087A publication Critical patent/GB810087A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
    • C07C69/616—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety polycyclic
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/48—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing ten 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
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic 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
    • C10M2207/282—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
    • C10M2207/286—Esters of polymerised unsaturated 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/06—Instruments or other precision apparatus, e.g. damping fluids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Cosmetics (AREA)

Abstract

The invention comprises alkyl arylstearates of general formula <FORM:0810087/IV (b)/1> where x + y = 15, Ar is aryl, R1 is hydrogen or an alkyl, cycloalkyl or alkyl substituted cycloalkyl group of 4-18 carbon atoms, or together with R2 is a divalent alkylene group containing from 4-18 carbon atoms and R2 and R3 are alkyl cycloalkyl or alkyl substituted cycloalkyl groups containing from 4-18 carbon atoms. The compounds may be prepared in two stages. In the first stage a substituted aromatic compound of the formula <FORM:0810087/IV (b)/2> is condensed with an hydroxystearate of the formula <FORM:0810087/IV (b)/3> where R4 is methyl or ethyl, in the presence of boron fluoride, the methyl or ethyl arylstearate so formed being hydrolysed to give the free arylstearic acid, which is then esterified with an alcohol of formula R3OH. The first stage of the invention is preferably carried out at elevated temperatures, e.g. 120-180 DEG C. in the presence of a dehydrating agent such as phosphoric acid, zinc chloride or phosphoric anhydride, in a proportion of 1/4 to 2 mols. per mol. of hydroxystearate. The boron fluoride is preferably present in 1/2 to 3 mols. per mol. of hydroxystearate. The methyl or ethyl arylstearate may be isolated by neutralizing the reaction mixture and then distilling it under reduced pressure. The hydrolysis may be carried out by adding the methyl or ethyl amylstearate to a boiling solution of a strong base, e.g. caustic soda or potash, calcium or barium hydroxide, in an aqueous alcohol. The mixture is kept at elevated temperature for a time and then cooled and acidified with e.g. 5 per cent aqueous hydrochloric acid when the liberated arylstearic acid separates out on top of the aqueous phase. The esterification of the acid may be carried out in the presence of an acid catalyst such as sulphuric acid benzene sulphonic acid, or b -naphthylsulphonic acid, and an inert solvent such as benzene. The excess water is azeotropically distilled off and the excess inert solvent evaporated. Specified substituents Ar are phenyl or naphthyl and specified substituents for R1, R2 and R3 are butyl, hexyl, ethylhexyl, cyclohexyl, methylcyclohexyl, dimethyl cyclohexyl, ethylcyclohexyl, diethylcyclohexyl, bicyclodecyl, dodecyl, palmityl and stearyl. Examples are given of the preparation of 2-ethylhexyl dibutylphenylstearate, dodecyl 2-ethylhexylphenylstearate, butyl dodecylphenylstearate, butyl di-2-ethylhexylphenylstearate, 2-ethylhexyl bicyclododecylphenylstearate, butyl stearylphenylstearate, methylcyclohexyl cyclohexylphenylstearate, 2-ethylhexyl dodecylnaphthylstearate, stearyl tetrahydronaphthylstearate and their corresponding methyl compounds.
GB34050/56A 1955-11-09 1956-11-07 Alkyl arylstearates and process of producing same Expired GB810087A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR1136066T 1955-11-09

Publications (1)

Publication Number Publication Date
GB810087A true GB810087A (en) 1959-03-11

Family

ID=9640060

Family Applications (1)

Application Number Title Priority Date Filing Date
GB34050/56A Expired GB810087A (en) 1955-11-09 1956-11-07 Alkyl arylstearates and process of producing same

Country Status (3)

Country Link
BE (1) BE551835A (en)
FR (1) FR1136066A (en)
GB (1) GB810087A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3337460A (en) * 1965-09-03 1967-08-22 Sinclair Research Inc Esters of polyhydric alkanols and dibasic aryl-fatty acids

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3337460A (en) * 1965-09-03 1967-08-22 Sinclair Research Inc Esters of polyhydric alkanols and dibasic aryl-fatty acids

Also Published As

Publication number Publication date
FR1136066A (en) 1957-05-09
BE551835A (en) 1900-01-01

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