Epichlorohydrin → N,N,N,N',N',N'-Hexamethyl-2-(oxiranylmethoxy)-1,3-propanediaminium dichloride

Epichlorohydrin (18.5 g, 0.2 mole, Aldrich) and hexane (100 mL) were charged to a round bottom flask fitted with a reflux condenser. An alkaline solution consisting of BTA (24.74 g, 0.1 mole), NaOH (12 g, 0.3 mole) and 44 g of water was prepared and added dropwise to the epichlorohydrin solution over approx. 30 minutes with vigorous stirring. The addition of BTA solution was begun with all components at room temperature, but the strongly exothermic reaction caused the temperature to rise sharply. The rate of addition was controlled such that at no time did the temperature of the reaction mixture exceed 50° C. Vigorous stirring was continued for 1 hour after addition of the alkaline BTA solution was finished. After the reaction mixture had cooled to room temperature, stirring was stopped and the liquid portion was decanted from the sodium chloride precipitate. The water and hexane layers were separated and the hexane layer was discarded. The water layer was evaporated under reduced pressure. The resulting residue was triturated with 100 mL anhydrous MeOH and additional insoluble sodium chloride precipitate was filtered away. Solvent was evaporated under reduced pressure to yield 32 g of a thick, yellowish liquid. By direct titration of epoxy groups (tetrabutylammonium iodide/perchloric acid method), the crude product was determined to be 91.4% pure (96.4% yield). 1H-NMR, 13C-NMR and mass spectrometry were consistent with the assigned structure.

1. customfitted with a reflux condenser
2. customwas prepared
3. additionThe addition of BTA solution
4. customwas begun with all components at room temperature
5. customthe strongly exothermic reaction
6. additionThe rate of addition
7. customexceed 50° C
8. additionafter addition of the alkaline BTA solution
9. stirringstirring
10. customthe liquid portion was decanted from the sodium chloride precipitate
11. customThe water and hexane layers were separated
12. customThe water layer was evaporated under reduced pressure
13. customThe resulting residue was triturated with 100 mL anhydrous MeOH and additional insoluble sodium chloride precipitate
14. filtrationwas filtered away
15. customSolvent was evaporated under reduced pressure
16. customto yield 32 g of a thick, yellowish liquid

ORD record

ord-edf621c06f82492b9dad928b9edb554c

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07214806B2