Patent GB-768777-A (GB)
Title: Chloroaryloxyacetates and chloroaryloxypropionates of the partial esters of 2, 2-dichloropropionic acid and an aliphatic polyhydric alcohol
IPC: C07C69/712
Filed: 1955-04-15
Abstract: The invention comprises a mixed ester of an aliphatic polyhydric alcohol consisting of glycerol, ethylene glycol, propylene glycol, trimethylene glycol, butylene glycol or a di-or tri-alkylene glycol of the ethylene, propylene or trimethylene series in which at least one hydroxyl of the alcohol is esterified with 2,2-dichloropropionic acid and the other hydroxyls of the alcohol are esterified with a chloroaryloxyacetic acid or a chloroaryloxypropionic acid.  Such compounds can be produced by reacting (1) a chloraryloxyacetic acid or a chloraryloxypropionic acid with (2) a partial ester of 2,2-dichloro-propionic acid and the appropriate polyhydric alcohol, suitably in the presence of an esterification catalyst, with removal of water as formed and in the presence of a solvent such as toluene, chlorobenzene or ethylene dichloride.  Alternatively there may be reacted together (1) 2,2-dichloropropionic acid, and (2) a partial ester of a chloroaryloxyacetic acid or chloroaryloxypropionic acid with the aliphatic polyhydric alcohol.  Examples describe the preparation by these methods of (1) ethylene glycol 2,2-dichloropropionate 2,4-dichlorophenoxyacetate; (2) glycerol 2,2-dichloropropionate bis - (2,4,5 - trichlorophenoxyacetate); (3) diethylene glycol 2,2-dichloropropionate 2 - (2,4,5 - trichlorophenoxy) - propionate; (4) dipropylene glycol 2,2-dichloropropionate 2 - (2,4 - dichlorophenoxy) - propionate; (5) trimethylene glycol 2,2-dichloropropionate 4 - chloro - 2 - methylphenoxyacetate; and (6) propylene glycol 2,2-dichloropropionate 2,4,5-trichlorophenoxyacetate.  The starting compounds are obtained by reacting the appropriate polyhydric alcohol with a chloroaryloxyacetic acid, chloroaryloxypropionic acid or 2,2-dichloropropionic acid.ALSO:A herbicidal composition comprises as active ingredient a mixed ester of an aliphatic polyhydric alcohol consisting of glycerol, ethylene glycol, propylene glycol, trimethylene glycol, butylene glycol or a di- or trialkylene glycol of the ethylene, propylene or trimethylene series in which at least one hydroxyl of the alcohol is esterified with 2, 2-dichloropropionic acid and the other hydroxyls of the alcohol are esterified with a chloroaryloxyacetic acid or a chloroaryloxypropionic acid.  The ester may be dispersed on an inert finely divided solid and employed as dusts and such mixtures may be dispersed in water with wetting agents.  The esters may also be used as constituents of oil-in-water emulsions or water dispersions, with or without wetting, dispersing and emulsifying agents.  Esters of the preparation of which is described (see Group IV(b)) are ethylene glycol 2, 2-dichloropropionate 2, 4 - dichlorophenoxy - acetate; glycerol 2, 2 - dichloropropionate bis (2, 4, 5 - trichlorophenoxyacetate); diethylene glycol 2, 2 - dichloropropionate 2 - (2, 4, 5 - trichlorophenoxy) propionate; dipropylene glycol 2, 2-dichloropropionate 2 - (2, 4 - dichlorophenoxy) - propionate; trimethylene glycol 2, 2 - dichloropropionate 4 - chloro - 2 - methylphenoxyacetate; propylene glycol 2, 2 - dichloro - propionate 2, 4, 5 - trichlorophenoxyacetate.