GB853099A - Improvements in the production of aryloxy fatty acids - Google Patents

Improvements in the production of aryloxy fatty acids

Info

Publication number
GB853099A
GB853099A GB17854/59A GB1785459A GB853099A GB 853099 A GB853099 A GB 853099A GB 17854/59 A GB17854/59 A GB 17854/59A GB 1785459 A GB1785459 A GB 1785459A GB 853099 A GB853099 A GB 853099A
Authority
GB
United Kingdom
Prior art keywords
acid
phenol
dichlorophenoxy
alcohol
acids
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
GB17854/59A
Inventor
Tim Toepel
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.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik 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 BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB853099A publication Critical patent/GB853099A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • 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
    • C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

A process for the production of aryloxy fatty acids comprises reacting a phenol with a halogenated fatty acid containing at least 3 carbon atoms at elevated temperature in aqueous alkali hydroxide solution in the presence of an aliphatic or cycloaliphatic alcohol of at least 3 carbon atoms which is volatile with steam. The reaction is preferably carried out at 90-110 C. using a 40-60% aqueous sodium hydroxide solution and 60-150% by weight of the alcohol based on the phenol which may be present in a slight excess. The alkali solution is added to the mixture of acid, phenol and alcohol which is then refluxed, a mineral acid added to neutralise the excess alkali and phenol, the alcohol and excess phenol removed by steam distillation and further mineral acid added to precipitate the aryloxy fatty acid. The phenol used is preferably phenol itself or naphthol or phenols or naphthols bearing one or more alkyl and/or halogen substituents. The halogenated fatty acid is preferably an a -chloro acid. Lists of suitable acids and phenols are given. Examples illustrate the use of n-propanol, n-butanol, iso-butanol, isoamyl alcohol, 2-ethyl-hexanol and cyclo-hexanol and describe the preparation of a -2-methylphenoxy, phenoxy, 2, 4-dimethyl-phenoxy, 2, 4-dichlorophenoxy, 2, 4, 5-trichlorophenoxy and b -naphthoxy-propionic acids ; b -(2, 4-dichlorophenoxy) propionic acid ; a -(2, 4-dichlorophenoxy) caproic acid ; a -phenoxy and a -(2, 4-dichlorophenoxy)-isovaleric acid and a -phenoxy and a -(2,4-dichlorophenoxy)-stearic acid. a -bromo-caproic and isovaleric acids are prepared by reacting the acids with bromine and phosphorous trichloride. a -bromo-stearic acid is prepared by reacting the acid with bromine and red phosphorous.
GB17854/59A 1958-05-29 1959-05-26 Improvements in the production of aryloxy fatty acids Expired GB853099A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE853099X 1958-05-29

Publications (1)

Publication Number Publication Date
GB853099A true GB853099A (en) 1960-11-02

Family

ID=6786869

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17854/59A Expired GB853099A (en) 1958-05-29 1959-05-26 Improvements in the production of aryloxy fatty acids

Country Status (1)

Country Link
GB (1) GB853099A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0288305A1 (en) * 1987-04-23 1988-10-26 Riker Laboratories, Inc. Di-t-butylphenyl alkyl and benzyl ethers

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0288305A1 (en) * 1987-04-23 1988-10-26 Riker Laboratories, Inc. Di-t-butylphenyl alkyl and benzyl ethers
US4973731A (en) * 1987-04-23 1990-11-27 Riker Laboratories, Inc. Di-t-butylphenyl alkyl and benzyl ether nitriles

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