Isolation of choline esters from aqueous solutions by extraction with sodium tetraphenylboron in organic solvents.
1. The method is based on the observation that choline esters and sodium tetraphenylboron (Kalignost) form complexes that are insoluble in water but soluble in organic solvents such as nitriles, higher ketones and benzyl alcohol. 2. The extraction procedure is an example of liquid cation exchange where tetraphenylboron is the cation-exchange group. 3. The proportion of choline esters extracted depends on the type and total amount of cation in the aqueous phase and the amount of sodium tetraphenylboron in the organic solvent. 4. The proportion of choline esters extracted is independent of the choline ester concentration, the pH (between 8 and 3) and the relative volumes of the two phases. 5. The affinity of sodium tetraphenylboron for choline esters increases with an increase in the size of the acyl group. 6. The choline ester extracted can be released into an aqueous solution by treatment with strong acids, silver salts and anion-exchange resins.
D000109:Acetylcholine / Q000032:analysis*; D000438:Alcohols; D001896:Boron Compounds; D002794:Choline; D004952:Esters; D007659:Ketones; D008722:Methods; D009570:Nitriles; D012997:Solvents
D000438:Alcohols; D001896:Boron Compounds; D004952:Esters; D007659:Ketones; D009570:Nitriles; D012997:Solvents; D002794:Choline; D000109:Acetylcholine