GB700048A - Improvements in the manufacture of a composition of matter containing an aryloxyacetic ester - Google Patents

Improvements in the manufacture of a composition of matter containing an aryloxyacetic ester

Info

Publication number
GB700048A
GB700048A GB28004/51A GB2800451A GB700048A GB 700048 A GB700048 A GB 700048A GB 28004/51 A GB28004/51 A GB 28004/51A GB 2800451 A GB2800451 A GB 2800451A GB 700048 A GB700048 A GB 700048A
Authority
GB
United Kingdom
Prior art keywords
keryl
acids
alkyl
acetic
acid
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
GB28004/51A
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.)
Uniroyal Inc
Original Assignee
United States Rubber 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 United States Rubber Co filed Critical United States Rubber Co
Publication of GB700048A publication Critical patent/GB700048A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/708Ethers
    • C07C69/712Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Compositions comprising an ester of an aryloxy-acetic acid, e.g. phenoxyacetic and naphthoxy acetic acids, together with the amine salt of an alkyl substituted aryl sulphonic acid (the alkyl group of which contains at least ten carbons), which acts as a surface active agent, may be used as plasticizers for nitro-cellulose, polyvinyl acetate or polyvinyl chloride (see Group IV (b)).ALSO:Insecticidal compositions comprising an ester of an aryloxy acetic acid and an organic amine salt of an alkyl substituted aryl sulphonic acid, are prepared by reacting an aryloxy acetic acid with an alcohol in the presence of an alkyl substituted aryl sulphonic acid, the alkyl grouping containing at least ten carbon atoms as an esterification catalyst until esterification of said acid with said alcohol is substantially complete, thereafter neutralizing said alkyl substituted aryl sulphonic acid with an organic amine, and thereby forming in situ an amine salt which is available as a surface active agent when the resulting mixture is used. Particular aryloxy acetic acids are those phenoxy and naphthoxy acetic acids which may be nuclearly substituted with lower alkyl or halogen groups, and especially 2:4-dichloro- and 2:4:5-trichloro-phenoxyacetic acids. Alcohols mentioned include n-butanol, isopropanol, glycerol, butoxy ethanol, polypropylene glycol, iso-octyl alcohol and lauryl alcohol. The substituted aryl sulphonic acids are preferably those wherein the alkyl side chain is derived from long chain paraffinic hydrocarbons, and include keryl benzene, keryl toluene and keryl naphthalene sulphonic acids. The term "keryl" denotes a mixture of alkyl side-chains of length ranging from C12 to C16 derived from a highly saturated paraffinic kerosene. Other surface active agents, emulsifiers and aromatic, petroleum or chlorinated aliphatic hydrocarbon oils may also be added to give a stable concentrate, prior to mixing with oil or water for spraying purposes. In examples the esterification mixture of sulphonic acid, phenoxyacetic acid and alcohol are refluxed, removing water azeotropically, excess of the alcohol distilled off, and the ester produced formulated by the addition of a suitable amine (e.g. iso-propylamine, triethylamine, triethanolamine), to neutralize the sulphonic acid and then other additives, emulsifiers and solvents as described.ALSO:Plant growth regulants comprise an ester of an aryloxy acetic acid and an amine salt of an alkyl substituted aryl sulphonic acid (see Group IV (b)). Particular aryloxy acetic acids are 2:4-di and 2:4:5-tri-chlorophenoxy acetic, mono and di-chlorotoloxy acetic and b -naphthoxy acetic acids, esterified with lauryl, n-butyl, iso butyl, iso-octyl alcohols, polypropylene glycol and butoxy ethanol. Particular sulphonic acids are those in which the alkyl substituent contains at least ten carbon atoms, e.g. keryl benzene sulphonic and keryl toluene sulphonic acids (keryl denotes mixture of alkyl chains of from twelve to sixteen carbons). Various amines may be used including isopropylamine, triethylamine and mixtures of high primary aliphatic amines. Formulations may also contain solvents, e.g. petroleum oils such as kerosene, naphtha; aromatic hydrocarbons such as benzene, toluene, methyl naphthalene and chlorinated hydrocarbon oils; or alcohols such as mono-n-butyl ether of ethylene glycols. Other diluents may be present, e.g. emulsifiers such as polyoxy ethylene esters.ALSO:Weed killers or plant growth regulators comprise an ester of an aryloxy acetic acid and an organic amine salt of an alkyl substituted aryl sulphonic acid, (see Group IV(b)). Particular aryloxyacids include 2:4-di and 2:4:5-tri chlorophenoxy-acetic, b -naphthoxy acetic, monoand di-chlorotoloxy acetic acids, esterified with lauryl alcohol, n-butyl, iso-butyl, isooctyl alcohols, polypropylene glycol and butoxy ethanol. The particular sulphonic acids are those in which the alkyl substituent contains at least ten carbon atoms, such as keryl benzene sulphonic, and keryl toluene sulphonic acids (keryl denotes mixture of alkyl chains of from 12 to 16 carbon atoms). Particular amines which are used for salt-formation include isopropylamine, triethylamine, triethanolamine, and mixtures of high primary aliphatic amines. In addition, the formulations may contain as solvents petroleum oils such as kerosene, naphtha, aromatic hydrocarbons, benzene, toluene, methyl naphthalene, and chlorinated hydrocarbon oils; alcohols such as mono-n-butyl ether of ethylene glycol. The solvent hydrocarbon oil is preferably capable of admixture with water, to give a spraying emulsion. Additive surface action agents e.g. polyoxyethylene esters may be added for this purpose if necessary. Other diluents including emulsifiers may be included.
GB28004/51A 1951-03-28 1951-11-29 Improvements in the manufacture of a composition of matter containing an aryloxyacetic ester Expired GB700048A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US700048XA 1951-03-28 1951-03-28

Publications (1)

Publication Number Publication Date
GB700048A true GB700048A (en) 1953-11-25

Family

ID=22092524

Family Applications (1)

Application Number Title Priority Date Filing Date
GB28004/51A Expired GB700048A (en) 1951-03-28 1951-11-29 Improvements in the manufacture of a composition of matter containing an aryloxyacetic ester

Country Status (1)

Country Link
GB (1) GB700048A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2980646A (en) * 1957-12-16 1961-04-18 Eastman Kodak Co Stabilized polyethylene

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2980646A (en) * 1957-12-16 1961-04-18 Eastman Kodak Co Stabilized polyethylene

Similar Documents

Publication Publication Date Title
US3282971A (en) Fatty acid esters of polyhydric alcohols
US2614919A (en) Process of making herbicidal composition of matter
GB688056A (en) Improvements in or relating to esters of chlorinated phenoxyacetic acids
GB700048A (en) Improvements in the manufacture of a composition of matter containing an aryloxyacetic ester
US3158645A (en) 2, 3, 6-trichlorobenzyl-2, 4-dichlorophenoxy-acetate
US2198583A (en) Ether esters of nuclear substituted salicylic acids
DE1920187A1 (en) Aromatic polyisobutenyl succinimide etc derivatives
GB796505A (en) Improved synthetic lubricant
US2759965A (en) Esters of alpha-(2, 4-dichlorophenoxy) propionic acid
US2728653A (en) Tetrahydrofurfuryl ester of 4-chloro-2-methylphenoxyacetic acid
US2596089A (en) Esters of chlorinated phenoxyacetic acids
US2959609A (en) Process for preparing vinyl-phosphonic-acid-bis-(beta-chlorethyl)-ester
GB971527A (en) Process for reducing the readiness with which synthetic fibres accept an electric charge
GB728995A (en) Improvements in or relating to herbicidal compositions
US2010731A (en) Esters of substituted saturated fatty acids having 12 to 18 carbon atoms
US3459857A (en) Phospho-acid esters as fungitoxic agents
DE867396C (en) Process for the production of condensation products
US2846298A (en) Method of defoliating plants with sulfenyl and thiosulfenyl xanthates
US2194517A (en) Contact insecticide
GB717265A (en) Tetrahydrofurfuryl esters of polychlorophenoxy acetic acids as herbicidal agents
US3549750A (en) Alkoxy vinyl phosphono dithioates as nematocides
GB963044A (en) New phosphacyclohexanes and their preparation
GB853334A (en) Improvements relating to lubricating oil compositions
US2903348A (en) Defoliating cotton with isooctyl xanthoacetic acid
GB687347A (en) Improved lubricant blend