Hydrochloric Acid → N-Methyl-N-(prop-2-en-1-yl)prop-2-en-1-amine--hydrogen chloride (1/1)

Temperature

80 °C

A four-necked resin kettle was fitted with a glass stirring shaft connected to an overhead stirrer, a pH probe, a thermocouple, an addition funnel and a condenser. A Thermowatch® (manufactured by I-2-R, Instruments for Research and Industry Inc., Cheltenham, Pa.) was used to maintain the temperature throughout the reaction. A quantity of 223 g methyldiallylamine (MDAA, 98%) was charged to the reactor. The reactor was then cooled with an ice bath and 189 g of 37% hydrochloric acid (HCl) was added to the stirred reaction mixture at such a rate to maintain the temperature of the reaction mixture below 25° C. Upon finishing the addition of hydrochloric acid, the ice bath was removed and the reaction mixture was stirred at ambient temperature for one hour. At this point the reaction mixture was a clear light yellow solution. Into this solution of MDAA·HCl solution, 0.5 g of Versenex® 80 (40% aqueous solution of the sodium salt of ethylenediamine tetraacetate, available from Dow Chemical Co., Midland, Mich.) was added. A septum was inserted in place of the addition funnel and a sparge of high purity nitrogen gas was started through the reaction mixture. A bubbler was attached at the condenser. The stirrer was started at 500 rpm and an insulated heating mantle was placed on the reaction flask. The reaction mixture was heated to 80° C. and was sparged with high purity N2 for 30 minutes. Meanwhile, an aqueous initiator solution was prepared by dissolving 18.2 g of ammonium persulfate (APS) in 40 (mL) of deionized water followed by sparging of the APS solution with high purity N2 for 30 minutes. While maintaining the N2 sparge and heating the reaction at 80° C. the APS initiator solution was added to the reaction flask using a syringe pump at a rate of 0.30 (mL/min) until 15 mL APS initiator solution had been added. At this point the addition of initiator solution was halted and the reaction mixture was maintained at 80° C. for one hour while continuing to stir at 500 rpm. A second portion of 15 mL of APS initiator solution was added to the reaction flask using a syringe pump at a rate of 0.30 (mL/min). When this addition was completed the addition of initiator solution was halted and the reaction mixture was maintained at 80° C. for one hour while continuing to stir at 500 rpm. The remaining 20 mL of APS solution was added at this point via syringe pump at a rate of 0.30 mL per minute. The reaction mixture was held at 80° C. for 1 hour after the last of the APS solution had been added. Heating was then discontinued and 320 mL of DI water were added. Analysis of the final product solution by 13C NMR showed that a MDAA monomer conversion of 99+% had been achieved. The RSV of the resin was 0.160 dL/g. Total solids of the final solution was 44.8% and pH was 2.5.

1. customA four-necked resin kettle was fitted with a glass
2. customconnected to an overhead stirrer
3. temperatureto maintain the temperature
4. customthroughout the reaction
5. temperatureThe reactor was then cooled with an ice bath
6. temperatureto maintain the temperature of the reaction mixture below 25° C
7. customthe ice bath was removed
8. stirringthe reaction mixture was stirred at ambient temperature for one hour
9. addition) was added
10. customa sparge of high purity nitrogen gas
11. customwas sparged with high purity N2 for 30 minutes
12. customMeanwhile, an aqueous initiator solution was prepared
13. customby sparging of the APS solution with high purity N2 for 30 minutes
14. temperatureWhile maintaining the N2
15. customsparge
16. temperatureheating
17. customthe reaction at 80° C. the APS initiator solution
18. additionwas added to the reaction flask
19. additionhad been added
20. additionAt this point the addition of initiator solution
21. temperaturethe reaction mixture was maintained at 80° C. for one hour
22. stirringto stir at 500 rpm
23. additionWhen this addition
24. additionthe addition of initiator solution
25. temperaturethe reaction mixture was maintained at 80° C. for one hour
26. stirringto stir at 500 rpm
27. temperatureHeating

ORD record

ord-a16bd1d2fe554c9ca43ee84e2c33ed09

Source dataset

uspto-grants-2005_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06906133B2