GB833163A - Fluoroaromatic compounds and method of making the same - Google Patents

Fluoroaromatic compounds and method of making the same

Info

Publication number
GB833163A
GB833163A GB1652558A GB1652558A GB833163A GB 833163 A GB833163 A GB 833163A GB 1652558 A GB1652558 A GB 1652558A GB 1652558 A GB1652558 A GB 1652558A GB 833163 A GB833163 A GB 833163A
Authority
GB
United Kingdom
Prior art keywords
acid
fluoro
fluoborate
xylyloxyacetic
see group
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
GB1652558A
Inventor
Edgar Clay Britton
Theodore Rolland Keil
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.)
Dow Chemical Co
Original Assignee
Dow Chemical Co
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
Priority to DENDAT1075581D priority Critical patent/DE1075581B/en
Application filed by Dow Chemical Co filed Critical Dow Chemical Co
Priority to GB1652558A priority patent/GB833163A/en
Publication of GB833163A publication Critical patent/GB833163A/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
    • C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises 5-fluoro-2-biphenyloxyacetic acid and 4-fluoro-2,5-xylyloxyacetic acid. In a process wherein an aromatic diazonium fluoborate is decomposed by heating to form a corresponding fluoro-aromatic compound while having the diazonium fluoroborate dispersed in a substantially anhydrous inert liquid organic compound as reaction medium, said inert liquid organic compound being a solvent for the fluoro-aromatic compound, the decomposition reaction is carried out in the presence of an alkali metal fluoride or an alkali metal acid fluoride, in amount corresponding to from 1 to 2 stoichiometric proportions of the inorganic fluoride per part of the boron trifluoride theoretically possible to be evolved in the reactions, based on the aromatic diazonium fluoborate used. Representative of the solvents specified are heptane, benzene, chlorbenzenes, alkylated benzenes, phenetole, ethylene dichloride and trichloroethane. Atmospheric and higher or lower pressures may be employed and the process may be carried out batchwise or continuously. The preparation is described of fluorobenzene, p - fluorophenetole, p - fluoroanisole, p-fluorophenoxyacetic acid, 5-fluoro-2-biphenyloxyacetic acid and 4-fluoro-2,5-xylyloxyacetic acid. The products are employed as herbicides and insecticides (see Group VI). 2-(Carboxymethoxy) - 5 - biphenyldiazomium fluoborate is prepared by diazotizing 5-amino-2-biphenylyloxyacetic acid and treating the product with sodium fluoborate. 4-(Carboxymethoxy - 2,5 - xylenediazonium fluoborate is similarly prepared.ALSO:An insecticidal spray composition comprises 5-fluoro-2-biphenylyloxyacetic acid (see Group IV (b)) suspended in an aqueous solution containing an alkylaryl sodium sulphonate wetting agent. A herbecidal composition comprises an aqueous dispersion of 4-fluoro-2,5-xylyloxyacetic acid (see Group IV (b)) and an alkylaryl sodium sulphonate wetting agent.
GB1652558A 1958-05-22 1958-05-22 Fluoroaromatic compounds and method of making the same Expired GB833163A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DENDAT1075581D DE1075581B (en) 1958-05-22 Process for the preparation of fluoroaromatic compounds
GB1652558A GB833163A (en) 1958-05-22 1958-05-22 Fluoroaromatic compounds and method of making the same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1652558A GB833163A (en) 1958-05-22 1958-05-22 Fluoroaromatic compounds and method of making the same

Publications (1)

Publication Number Publication Date
GB833163A true GB833163A (en) 1960-04-21

Family

ID=10078904

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1652558A Expired GB833163A (en) 1958-05-22 1958-05-22 Fluoroaromatic compounds and method of making the same

Country Status (2)

Country Link
DE (1) DE1075581B (en)
GB (1) GB833163A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0022942A1 (en) * 1979-07-11 1981-01-28 Bayer Ag Process for preparing diazoniumtetrafluoroborates with nitrosyltetrafluoroborate, and their use
EP0022959A1 (en) * 1979-07-14 1981-01-28 Bayer Ag Process for the preparation of diazoniumtetrafluoroborates in a diluted aqueous solution
CN113401916A (en) * 2021-05-26 2021-09-17 大连鼎燕医药化工有限公司 Waste utilization of substituted aromatic hydrocarbon hydrogen fluoride diazonium salt pyrolysis fluorination reaction

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0022942A1 (en) * 1979-07-11 1981-01-28 Bayer Ag Process for preparing diazoniumtetrafluoroborates with nitrosyltetrafluoroborate, and their use
EP0022959A1 (en) * 1979-07-14 1981-01-28 Bayer Ag Process for the preparation of diazoniumtetrafluoroborates in a diluted aqueous solution
CN113401916A (en) * 2021-05-26 2021-09-17 大连鼎燕医药化工有限公司 Waste utilization of substituted aromatic hydrocarbon hydrogen fluoride diazonium salt pyrolysis fluorination reaction
CN113401916B (en) * 2021-05-26 2023-05-26 大连鼎燕医药化工有限公司 Waste utilization of pyrolysis fluoro reaction of substituted aromatic hydrocarbon hydrogen fluoride diazonium salt

Also Published As

Publication number Publication date
DE1075581B (en) 1960-02-18

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