Triethylamine ((CH3CH2)3N) is less soluble in water than ((CH3CH2)3N•HCl). Compared to the uncharged N atom in triethylamine, the positive charge on the N atom in triethylammonium chloride is more polar.
If your compound is not susceptible to moisture, you should dissolve it in dichloromethane or chloroform before giving it a brief wash in cold water and separating it. Cold water washing reduces the product's water solubility. Triethylamine and HCl (strong acid) are combined to form the salt triethylammonium chloride (weak base).
Chloroform readily dissolves the salt of triethylamine hydrochloride. To produce 93 grammes of crude using triethylamine hydrochloride salt, chloroform is first removed. In order to get a certain acidic pH, it is dissolved in 250 mL of water, cooled to 10 °C, then acidified by adding 10% hydrochloric acid.
Triethylamine ((CH3CH2)3N) is less soluble in water than ((CH3CH2)3N•HCl). Compared to the uncharged N atom in triethylamine, the positive charge on the N atom in triethylammonium chloride is more polar. Enhanced solubility results from greater interactions with water as a result of this increased polarity.
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