GB1448729A - Process for the production of hydroxyalkylphenyl derivatives - Google Patents

Process for the production of hydroxyalkylphenyl derivatives

Info

Publication number
GB1448729A
GB1448729A GB5977073A GB5977073A GB1448729A GB 1448729 A GB1448729 A GB 1448729A GB 5977073 A GB5977073 A GB 5977073A GB 5977073 A GB5977073 A GB 5977073A GB 1448729 A GB1448729 A GB 1448729A
Authority
GB
United Kingdom
Prior art keywords
formula
alkali metal
phenol
represent
alkyl
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
GB5977073A
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
Ciba 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 Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of GB1448729A publication Critical patent/GB1448729A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
    • 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
    • C08K5/134—Phenols containing ester groups
    • C08K5/1345—Carboxylic esters of phenolcarboxylic acids
    • 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
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/37—Thiols
    • C08K5/375—Thiols containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

1448729 Preparation of alkyl phenol derivatives CIBA GEIGY AG 27 Dec 1973 [27 Dec 1972] 59770/73 Heading C2C wherein R 1 and R 2 represent C 1 to C 6 alky groups, x is 6 to 30, y is 2 to 8 and each of z and z<SP>1</SP> are 2 to 12; are obtained by gradually adding methyl acrylate to a phenol of the formula so that the overall molar ratio of methyl acrylate and the phenol compound is at least 1 : 1 and an alcohol selected from (a) a monohydric alcohol of the formula HO(CH 2 ) x H, (b) a dihydric alcohol of the formula HO(CH 2 ) y OH, and (c) a thioether of the formula HO(CH 2 ) z -S-(CH 2 ) z1 OH, said reaction being carried out in the presence of from 0À001 to 10 mole per cent based on the phenol of Formula IV of an alkaline catalyst selected from alkali metal hydrides, alkali metal alkoxides of the formula wherein M is an alkali metal ion, X 1 , X 2 and X 3 represent H, alkyl, aryl or aralkyl groups having up to 12 C atoms; and alkali metal amides of the formula wherein X 4 and X 5 represent H, alkyl or aryl groups having up to 12 C atoms. The products are useful in the stabilization of organic materials normally subject to oxidative deterioration.
GB5977073A 1972-12-27 1973-12-27 Process for the production of hydroxyalkylphenyl derivatives Expired GB1448729A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US31881072A 1972-12-27 1972-12-27

Publications (1)

Publication Number Publication Date
GB1448729A true GB1448729A (en) 1976-09-08

Family

ID=23239658

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5977073A Expired GB1448729A (en) 1972-12-27 1973-12-27 Process for the production of hydroxyalkylphenyl derivatives

Country Status (6)

Country Link
JP (1) JPS4994645A (en)
CH (1) CH582124A5 (en)
DE (1) DE2364121A1 (en)
FR (1) FR2212324B1 (en)
GB (1) GB1448729A (en)
NL (1) NL7317616A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110156650A (en) * 2019-05-30 2019-08-23 杭州国盛新材料科技有限公司 A kind of thioether-type antioxidant and its synthetic method
CN114213291A (en) * 2021-12-31 2022-03-22 江苏极易新材料有限公司 Synthesis method of thiodiethylene bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ]

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3639400A1 (en) * 1986-11-18 1988-05-26 Huels Chemische Werke Ag Esters of 3-tert-butyl- or 3-tert-butyl-5-alkyl-4-hydroxyphenyl(alkane)carboxylic acids with ethoxylates of monofunctional thiophenols and thiols, process for their preparation and their use as stabilisers
EP0432089B1 (en) * 1989-11-08 1996-09-04 Ciba-Geigy Ag Lubricating oil compositions
US5206414A (en) * 1990-01-11 1993-04-27 Ciba-Geigy Corporation Process for the preparation of hydroxyphenylpropionic acid esters

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110156650A (en) * 2019-05-30 2019-08-23 杭州国盛新材料科技有限公司 A kind of thioether-type antioxidant and its synthetic method
CN114213291A (en) * 2021-12-31 2022-03-22 江苏极易新材料有限公司 Synthesis method of thiodiethylene bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ]
WO2023123566A1 (en) * 2021-12-31 2023-07-06 江苏极易新材料有限公司 Synthesis method for thiodiethylene bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]

Also Published As

Publication number Publication date
NL7317616A (en) 1974-07-01
FR2212324A1 (en) 1974-07-26
FR2212324B1 (en) 1976-10-08
DE2364121A1 (en) 1974-07-11
JPS4994645A (en) 1974-09-09
CH582124A5 (en) 1976-11-30

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee