GB1103145A - Process for the preparation of organic esters - Google Patents

Process for the preparation of organic esters

Info

Publication number
GB1103145A
GB1103145A GB23339/65A GB2333965A GB1103145A GB 1103145 A GB1103145 A GB 1103145A GB 23339/65 A GB23339/65 A GB 23339/65A GB 2333965 A GB2333965 A GB 2333965A GB 1103145 A GB1103145 A GB 1103145A
Authority
GB
United Kingdom
Prior art keywords
tert
butyl
hydroxyphenyl
carbon atoms
residue
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
GB23339/65A
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.)
Novartis AG
Original Assignee
JR Geigy AG
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 JR Geigy AG filed Critical JR Geigy AG
Publication of GB1103145A publication Critical patent/GB1103145A/en
Expired legal-status Critical Current

Links

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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio 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
    • C10M2207/283—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
    • C10M2207/287—Partial 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
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/015—Dispersions of solid lubricants
    • C10N2050/02—Dispersions of solid lubricants dissolved or suspended in a carrier which subsequently evaporates to leave a lubricant coating

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

As stabilizers for polyethylene, polypropylene or polystyrene, use is made of esters of the formula <FORM:1103145/C3/1> in which a lower alkyl or lower alkylene group contains up to 6 carbon atoms, n is 1-6 and R is the non-hydroxylated residue of an organic compound containing n hydroxy groups, more particularly the residue of a monohydric aliphatic alcohol containing 7-30 carbon atoms, the residue of a di- or poly-hydric alcohol of 2-30 carbon atoms, the residue of an alicylic alcohol of 5-7 carbon atoms or the residue of a mercapto alcohol containing 4-40 carbon atoms and 1-3 non-terminal sulphide linkages (see Division C2). Specific esters described include tetra - [3 - (3,5 - di - tert. - butyl - 4 - hydroxyphenyl) propionyloxymethyl] methane, 1,2,3,4,5,6 - hexa - [3 - (3,5 - di - tert. - butyl - 4 - hydroxyphenyl) propionyloxy] hexane and 3 - (dodecylthio)propyl - 3 - (3,5 - di - tert. - butyl - 4 - hydroxyphenyl) propionate. No details of the stabilizing treatment are given.ALSO:As stabilizers for animal, vegetable and hydrocarbon and ester lubricating oils, use is made of esters of the formula <FORM:1103145/C4-C5/1> in which a lower alkyl or lower alkylene group contains up to 6 carbon atoms, n is 1-6 and R is the non-hydroxylated residue of an organic compound containing n hydroxy groups, more particularly the residue of a monohydric aliphatic alcohol containing 7-30 carbon atoms, the residue of a di- or poly-hydric alcohol of 2-30 carbon atoms, the residue of an alicyclic alcohol of 5-7 carbon atoms or the residue of a mercapto alcohol containing 4-40 carbon atoms and 1-3 non-terminal sulphide linkages (see Division C2). Specific esters described include tetra - [3 - (3,5 - di - tert. - butyl - 4 - hydroxyphenyl propionyloxymethyl] methane 1,2,3,4,5,6 - hexa - [3 - (3,5 - di - tert. - butyl - 4 - hydroxyphenyl) propionyloxy] hexane and 3 - (dodecylthio) propyl - 3 - (3,5-di - tert. - butyl - 4 - hydroxyphenyl) propionate. No details of the stabilizing treatment are given.ALSO:The invention relates to a process for the manufacture of esters of the formula <FORM:1103145/C2/1> in which a lower alkyl or lower alkylene group contains up to 6 carbon atoms, n is 1-6 and R is the non-hydroxylated residue of an organic compound containing n hydroxy groups, more particularly the residue of a monohydric aliphatic alcohol containing 7-30 carbon atoms, the residue of a di- or poly-hydric aliphatic alcohol of 2-30 carbon atoms, the residue of an alicyclic alcohol of 5-7 carbon atoms or the residue of a mercapto alcohol containing 4-40 carbon atoms and 1-3 non-terminal sulphide linkages. The process consists in reacting an ester of the formula above, in which n is 1 and R denotes an alkyl group of 1-6 carbon atoms, with an alcohol of the formula (HO)nR in the presence of a hydride of an alkali or alkaline-earth metal, subject to the proviso that, when R contains only 1-6 carbon atoms and n is 1, the initial ester must contain fewer carbon atoms than the desired product. The reaction may be effected at 70-150 DEG C. under atmospheric or reduced pressure. In typical examples, methyl 3 - (3,5 - di - tert. - butyl - 4-hydroxyphenyl) propionate reacts, in the presence of lithium or calcium hydride, (1) with pentaerythritol, to produce tetra-[3-(3,5-di - tert. - butyl - 4 - hydroxyphenyl) propionyloxymethyl] methane; (2) with 1,1,1-trimethylolpropane, to produce 1,1,1-tris-[3-(3,5-di - tert. - butyl - 4 - hydroxyphenyl) propionyloxymethyl] propane; (3) with sorbitol, to produce 1,2,3,4,5,6 - hexa - [3 - (3,5 - di - tert.-butyl - 4 - hydroxyphenyl) propionyloxy] hexane; (4) with 1,4-butanediol, to produce 1,4-bis - [3 - (3,5 - di - tert. - butyl - 4 - hydroxyphenyl) propionyloxy] butane; and (5) with n-dodecylthiopropanol, to produce 3-(dodecylthio) propyl - 3 - (3,5 - di - tert. - butyl - 4 - hydroxyphenyl) propionate. Other specified alcohols which may be used include decyl alcohol, octadecyl alcohol, ethylene glycol, 1,2-octanediol, glycerol, 1,2,3-butanetriol, cyclopentanol, inositol, 2,21-diethanol sulphide and n - octylthioethylthioethanol. The products are useful as stabilizers for aliphatic ester lubricants and certain other materials (see Divisions C3 and C5). Methyl 3 - (3,5 - di - tert. - butyl - 4 - hydroxyphenyl) propionate, used as starting material in the examples, is obtainable by reacting 2,6-di-tert.-butylphenol with methyl acrylate. A number of similar esters similarly obtainable are also specified. Ethyl 2 - (3,5 - di - tert. - butyl - 4 - hydroxyphenyl) isobutyrate, another specified starting material, is obtainable by reacting 2,6-di-tert.-butyl-phenol with ethyl a -bromo-a -methyl-propionate. Ethyl (3,5 - di - tert. - butyl - 4 - hydroxyphenyl) acetate, another specified starting material, is obtainable by treating 3,5-di-tert.-butyl-4-hydroxybenzyl cyanide with hydrogen chloride. Methyl (3,5 - di - tert. - butyl - 4 - hydroxyphenyl) acetate, another specified starting material, is obtainable by esterifying the corresponding acid with methanol in the presence of p - toluene - sulphonic acid. Methyl 6 - (3,5-di - tert. - butyl - 4 - hydroxyphenyl) hexanoate is similarly obtainable from 6-(3,5-di-tert.-butyl-4-hydroxyphenyl) hexanoic acid.
GB23339/65A 1964-06-02 1965-06-01 Process for the preparation of organic esters Expired GB1103145A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US37208364A 1964-06-02 1964-06-02

Publications (1)

Publication Number Publication Date
GB1103145A true GB1103145A (en) 1968-02-14

Family

ID=23466654

Family Applications (1)

Application Number Title Priority Date Filing Date
GB23339/65A Expired GB1103145A (en) 1964-06-02 1965-06-01 Process for the preparation of organic esters

Country Status (7)

Country Link
AT (1) AT253491B (en)
BE (1) BE664811A (en)
CH (1) CH454171A (en)
ES (1) ES313657A1 (en)
FR (1) FR1436393A (en)
GB (1) GB1103145A (en)
NL (1) NL6506933A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0255743A1 (en) * 1986-07-25 1988-02-10 ENICHEM SYNTHESIS S.p.A. Tetrakis[3-(3,5-di-tert.buthyl-4-hydroxyphenyl)propionyl-oxymethyl]methane with amorphous structure, process for its preparation and its use as a stabilizer
EP0358157A1 (en) * 1988-09-07 1990-03-14 Yoshitomi Pharmaceutical Industries, Ltd. Individual alpha-form particle crystals of tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionyl-oxymethyl]methane and process for its production
EP0573393A1 (en) * 1992-06-04 1993-12-08 Ciba-Geigy Ag Perfluoroalkyl substituted hydroxyphenylalkanoic ester antioxidants
US6878843B2 (en) 2000-06-23 2005-04-12 Ciba Specialty Chemicals Corp. Method for preparing hydroxyphenyl carboxylic acid esters
CN103193635A (en) * 2013-04-08 2013-07-10 南通惠康国际企业有限公司 Method for preparing antioxidant bi[3-(3,5-di-tert-butyl-4-hydroxy phenyl)] N-butyl glycol ester
WO2019096868A1 (en) * 2017-11-17 2019-05-23 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Compounds having a stabilizing effect, method for producing said compounds, composition containing said stabilizing compounds, method for stabilizing an organic component, and use of stabilizing compounds

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2364126A1 (en) * 1972-12-27 1974-07-11 Ciba Geigy Ag PROCESS FOR THE PREPARATION OF HYDROXYALKYLPHENYL DERIVATIVES
US3984460A (en) * 1973-09-25 1976-10-05 Ciba-Geigy Corporation Esters of trisubstituted hydroxyphenylalkanoic acids
JPS50147711A (en) 1974-05-17 1975-11-27
US3956361A (en) 1974-05-23 1976-05-11 Ciba-Geigy Corporation Hindered phenolic derivatives of norbornane thioalcohols
US4093587A (en) * 1974-07-23 1978-06-06 Ciba-Geigy Corporation Trisubstituted hydroxyphenylalkanoic acid ester and amide stabilized compositions
US3954839A (en) * 1974-12-12 1976-05-04 Ciba-Geigy Corporation Hindered hydroxyphenylalkanoates of thioether isopropanols
US3987086A (en) * 1974-12-12 1976-10-19 Ciba-Geigy Corporation Hindered hydroxyphenylalkanoates of substituted vicinal glycols
US4001299A (en) * 1974-12-12 1977-01-04 Ciba-Geigy Corporation Hindered hydroxyphenylalkanoates of substituted isopropanols

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0255743A1 (en) * 1986-07-25 1988-02-10 ENICHEM SYNTHESIS S.p.A. Tetrakis[3-(3,5-di-tert.buthyl-4-hydroxyphenyl)propionyl-oxymethyl]methane with amorphous structure, process for its preparation and its use as a stabilizer
EP0358157A1 (en) * 1988-09-07 1990-03-14 Yoshitomi Pharmaceutical Industries, Ltd. Individual alpha-form particle crystals of tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionyl-oxymethyl]methane and process for its production
US5089655A (en) * 1988-09-07 1992-02-18 Yoshitomi Pharmaceutical Industries, Ltd. Individual α-form particle crystals of tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionyloxymethyl]methane and process for its production
EP0573393A1 (en) * 1992-06-04 1993-12-08 Ciba-Geigy Ag Perfluoroalkyl substituted hydroxyphenylalkanoic ester antioxidants
US5310773A (en) * 1992-06-04 1994-05-10 Ciba-Geigy Corporation Perfluoroalkyl substituted hydroxyphenylalkanoic ester antioxidants and stabilized compositions
US6878843B2 (en) 2000-06-23 2005-04-12 Ciba Specialty Chemicals Corp. Method for preparing hydroxyphenyl carboxylic acid esters
CN103193635A (en) * 2013-04-08 2013-07-10 南通惠康国际企业有限公司 Method for preparing antioxidant bi[3-(3,5-di-tert-butyl-4-hydroxy phenyl)] N-butyl glycol ester
CN103193635B (en) * 2013-04-08 2015-06-03 南通大学 Method for preparing antioxidant bi[3-(3,5-di-tert-butyl-4-hydroxy phenyl)] N-butyl glycol ester
WO2019096868A1 (en) * 2017-11-17 2019-05-23 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Compounds having a stabilizing effect, method for producing said compounds, composition containing said stabilizing compounds, method for stabilizing an organic component, and use of stabilizing compounds
CN111556864A (en) * 2017-11-17 2020-08-18 弗劳恩霍弗应用研究促进协会 Compound with stabilizing effect, preparation method of compound, composition containing stabilizing compound, method for stabilizing organic component and application of stabilizing compound
JP2021503456A (en) * 2017-11-17 2021-02-12 フラウンホーファー−ゲゼルシャフト ツゥア フェアデルング デア アンゲヴァンドテン フォァシュング エー．ファウ． A compound having a stabilizing effect, a method for producing the compound, a composition containing the stabilizing compound, a method for stabilizing an organic component, and the use of the stabilizing compound.
CN111556864B (en) * 2017-11-17 2022-07-08 弗劳恩霍弗应用研究促进协会 Compounds with stabilizing effect, preparation method and use thereof, compositions containing same and method for stabilizing organic components
US11407720B2 (en) 2017-11-17 2022-08-09 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Compounds having a stabilizing effect, method for producing said compounds, composition containing said stabilizing compounds, and uses of the compounds

Also Published As

Publication number Publication date
BE664811A (en) 1965-12-02
CH454171A (en) 1968-04-15
FR1436393A (en) 1966-04-22
NL6506933A (en) 1965-12-03
AT253491B (en) 1967-04-10
ES313657A1 (en) 1966-02-16

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