GB720838A - Esters of ª‡-2,4,5-trichlorophenoxypropionic acid - Google Patents

Esters of ª‡-2,4,5-trichlorophenoxypropionic acid

Info

Publication number
GB720838A
GB720838A GB7966/53A GB796653A GB720838A GB 720838 A GB720838 A GB 720838A GB 7966/53 A GB7966/53 A GB 7966/53A GB 796653 A GB796653 A GB 796653A GB 720838 A GB720838 A GB 720838A
Authority
GB
United Kingdom
Prior art keywords
butoxy
reaction
acid
water
propoxy
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
GB7966/53A
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
Publication of GB720838A publication Critical patent/GB720838A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters 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
    • C07C69/67—Esters 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
    • C07C69/708—Ethers
    • C07C69/712—Ethers 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

Abstract

The invention comprises esters of a -2,4,5-trichlorophenoxypropionic acid having the formula <FORM:0720838/IV (b)/1> wherein n is 2 or 3, m is 1, 2 or 3 and R represents an alkyl radical containing 1, 2, 3 or 4 carbon-atoms. The compounds are prepared by reacting one molecular proportion of a -2,4,5-trichlorophenoxypropionic acid with one molecular proportion of a glycol or polyglycol monoether of the formula R-(OCnH2n)m-OH in the presence of an esterification catalyst such as sulphuric acid or an aryl sulphuric acid. The reaction is preferably carried out at reflux temperature in an inert solvent, which should be substantially immiscible with water and boiling in the range of 80 DEG to 150 DEG C. (e.g. benzene, toluene, xylene and ethylene dichloride), when the water of reaction distils out of the reaction zone as it is formed. The reaction product is washed free from catalyst and excess acid with aqueous sodium carbonate and water, and the solvent and traces of water are then removed by distillation under reduced pressure. Alternatively, an excess of the ether alcohol reactant may be used as a solvent, the excess ether alcohol together with water of reaction being distilled out of the reaction zone under vacuum during the reaction. The examples describe the preparation of the 2-(2-butoxy - 1 - methylethoxy) - 1 - methylethanol, 1 - butoxy - 2 - propyl, 2 - ethoxyethyl, 2 -(2 - methoxyethoxy) ethyl and a mixture of the butoxy-propyl, butoxy-propoxy-propyl, and butoxy - propoxy - propoxy - propyl esters of a - 2,4,5 - trichlorophenoxypropionic acid. Glycol and polyglycol alkylmonoethers such as 1 - butoxy - 2 - propanol, 2 - (2 - butoxy - 1 - methylethoxy) - 1 - methylethanol, 2 - ethoxy - ethanol, 2 -(2 - methoxyethoxy) - ethanol and butoxy - propoxy - propanol are obtained by the reaction of ethylene oxide and/or propylene oxide with the appropriate molecular proportion of a monohydric aliphatic alcohol in the presence of a catalyst such as sulphuric acid or sodium hydroxide. The reactants may, for example, be mixed and heated together in the presence of the catalyst for half-an-hour at 170 DEG C. and under autogenous pressure.
GB7966/53A 1952-06-02 1953-03-23 Esters of ª‡-2,4,5-trichlorophenoxypropionic acid Expired GB720838A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US720838XA 1952-06-02 1952-06-02

Publications (1)

Publication Number Publication Date
GB720838A true GB720838A (en) 1954-12-29

Family

ID=22105453

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7966/53A Expired GB720838A (en) 1952-06-02 1953-03-23 Esters of ª‡-2,4,5-trichlorophenoxypropionic acid

Country Status (1)

Country Link
GB (1) GB720838A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1085151B (en) * 1957-08-07 1960-07-14 Basf Ag Process for the production of more highly chlorinated trichloromethylcyclooctanes
US4227009A (en) 1976-05-26 1980-10-07 Hoechst Aktiengesellschaft Phenoxyphenoxy-propionic acid derivatives
US4354034A (en) * 1978-06-30 1982-10-12 Imperial Chemical Industries Limited Dihalophenoxypropionic acids and their derivatives, and their use as cotton desiccants

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1085151B (en) * 1957-08-07 1960-07-14 Basf Ag Process for the production of more highly chlorinated trichloromethylcyclooctanes
US4227009A (en) 1976-05-26 1980-10-07 Hoechst Aktiengesellschaft Phenoxyphenoxy-propionic acid derivatives
US4354034A (en) * 1978-06-30 1982-10-12 Imperial Chemical Industries Limited Dihalophenoxypropionic acids and their derivatives, and their use as cotton desiccants

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