GB679676A - Improved method for the production of salts of aromatic-oxy-aliphatic carboxylic acids - Google Patents

Improved method for the production of salts of aromatic-oxy-aliphatic carboxylic acids

Info

Publication number
GB679676A
GB679676A GB828950A GB828950A GB679676A GB 679676 A GB679676 A GB 679676A GB 828950 A GB828950 A GB 828950A GB 828950 A GB828950 A GB 828950A GB 679676 A GB679676 A GB 679676A
Authority
GB
United Kingdom
Prior art keywords
alkali
phenol
solution
salt
reaction
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
GB828950A
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
Application filed by Dow Chemical Co filed Critical Dow Chemical Co
Priority to GB828950A priority Critical patent/GB679676A/en
Publication of GB679676A publication Critical patent/GB679676A/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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • 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
    • 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

Abstract

Salts of aryloxy-aliphatic acids are made by forming an aqueous solution of a phenol, a water-soluble salt of a monochloro-aliphatic carboxylic acid and an alkali, which solution initially contains alkali in an amount (excluding that necessary for forming the salt of the chloroacid) equivalent to 80-100 per cent of the phenol and is of pH at least 9.5 when using a nuclear-chlorinated phenol; the mixture is heated to reaction temperature and alkali is added as necessary to maintain the pH within the range defined by the alkali concentrations given above throughout the major part of the reaction. The solution may be formed by mixing the reactants in any order, preferably by adding a solution of the chloroacid salt to a hot solution of the phenol and alkali. The further addition of alkali may be effected automatically by feed mechanism controlled by change of pH as detected by a pair of electrodes in the reaction mixture. The product may be isolated by crystallization, or alternatively the mixture may be acidified, extracted with a solvent and the free acid purified by distillation or crystallization. Alternatively the free acid may be obtained from the purified salt. The reaction temperature is usually above 80 DEG C. and may be up to 150 DEG C. under pressure. The process may be carried out continuously. Examples show the reaction of sodium chloroacetate with 2 : 4-dichlorophenol, b -naphthol, 2 : 6 - dimethoxyphenol, 2 : 5 - dimethylphenol and 2- and 4-nitrophenols. Also, sodium a -chloropropionate is reacted with 2-and 3-chlorphenols and with 2 : 4-dichlorophenol. Other specified reactants are phenol itself, 4 - chlorophenol, 2 : 6 - dichlorophenol, 2 : 4 : 6 - trichlorophenol, 2 - bromophenol, 2 : 4 - dibromophenol, cresols, the three ethylphenols, isopropylphenols, guaiacol, dimethoxyphenols, a -naphthol and 2- and 4-phenylphenols and b -chloropropionic and the three chlorobutyric acid salts. The alkali is preferably sodium, potassium or lithium hydroxide. Other alkalis, e.g. ammonia, sodium carbonate, lime or barium hydroxide may be used alone or with an alkali metal hydroxide.
GB828950A 1950-04-03 1950-04-03 Improved method for the production of salts of aromatic-oxy-aliphatic carboxylic acids Expired GB679676A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB828950A GB679676A (en) 1950-04-03 1950-04-03 Improved method for the production of salts of aromatic-oxy-aliphatic carboxylic acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB828950A GB679676A (en) 1950-04-03 1950-04-03 Improved method for the production of salts of aromatic-oxy-aliphatic carboxylic acids

Publications (1)

Publication Number Publication Date
GB679676A true GB679676A (en) 1952-09-24

Family

ID=9849665

Family Applications (1)

Application Number Title Priority Date Filing Date
GB828950A Expired GB679676A (en) 1950-04-03 1950-04-03 Improved method for the production of salts of aromatic-oxy-aliphatic carboxylic acids

Country Status (1)

Country Link
GB (1) GB679676A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4035416A (en) * 1972-11-02 1977-07-12 The Dow Chemical Company Process for making phenoxyalkanoic acids
FR2486071A2 (en) * 1979-06-29 1982-01-08 Rhone Poulenc Agrochimie Optically active aryloxy-alkanoic acid herbicides prepn. - by reacting optically active alkali metal 2-halo-alkanoic acids with alkali metal phenolate in aq. medium
EP0108374A1 (en) * 1982-11-05 1984-05-16 Hoechst Aktiengesellschaft Process for the preparation of hydroxy-phenoxy-alkane-carboxylic acids
US5798362A (en) * 1994-03-18 1998-08-25 Recordati S.A. Chemical And Pharmaceutical Company Quinazolinyl-amino derivatives having α-antagonist activity
CN109053409A (en) * 2017-06-13 2018-12-21 江西天宇化工有限公司 A kind of preparation method of 2,4-D

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4035416A (en) * 1972-11-02 1977-07-12 The Dow Chemical Company Process for making phenoxyalkanoic acids
FR2486071A2 (en) * 1979-06-29 1982-01-08 Rhone Poulenc Agrochimie Optically active aryloxy-alkanoic acid herbicides prepn. - by reacting optically active alkali metal 2-halo-alkanoic acids with alkali metal phenolate in aq. medium
EP0108374A1 (en) * 1982-11-05 1984-05-16 Hoechst Aktiengesellschaft Process for the preparation of hydroxy-phenoxy-alkane-carboxylic acids
US5798362A (en) * 1994-03-18 1998-08-25 Recordati S.A. Chemical And Pharmaceutical Company Quinazolinyl-amino derivatives having α-antagonist activity
CN109053409A (en) * 2017-06-13 2018-12-21 江西天宇化工有限公司 A kind of preparation method of 2,4-D
CN109053409B (en) * 2017-06-13 2021-12-24 江西天宇化工有限公司 Preparation method of 2,4-D

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