Chemical process for the production of haloalkenone ethers
View Patent ↗The present invention relates to a continuous process for producing a haloalkenone ether of the Formula (I) wherein R 1 is C 1 -C 6 haloalkyl, R 2 is a C 1 -C 6 alkyl or phenyl, the process comprising:—(i) reacting, in a first continuous stirred tank reactor comprising a solvent, a halide of Formula (II) wherein R 1 is as previously defined and R 3 is halogen, with a vinyl ether of Formula (III) wherein R 2 is as previously defined, to form an intermediate compound of Formula (IV), wherein the concentration of the vinyl ether of Formula (III) in the reaction mass is 15% or less w/w; and (ii) transferring the reaction mass from the first continuous stirred tank reactor into a subsequent continuous stirred tank reactor, wherein the conditions within the subsequent reactor permit the elimination of hydrogen halide (HR 3 ) from the intermediate compound of Formula (IV) to provide the haloalkenone ether of Formula (I).
1. A continuous process for producing a haloalkenone ether of Formula (I):
wherein R 1 is a C 1 -C 6 haloalkyl, and R 2 is a C 1 -C 6 alkyl or phenyl, the process comprising:
(i) reacting, in a first continuous stirred tank reactor comprising a solvent, a halide of Formula (II):
wherein R 3 is a halogen, with a vinyl ether of Formula (III):
to form an intermediate compound of Formula (IV):
wherein a concentration of the vinyl ether of Formula (III) in a reaction mass of said reacting step is 15% or less w/w; and
(ii) transferring the reaction mass from the first continuous stirred tank reactor into a subsequent continuous stirred tank reactor, wherein conditions within the subsequent reactor permit elimination of hydrogen halide (HR 3 ) from the intermediate compound of Formula (IV) to provide the haloalkenone ether of Formula (I).
2. A process according to claim 1 , wherein the concentration of the vinyl ether of Formula (III) in the reaction mass is 10% or less w/w.
3. A process according to claim 1 , wherein the solvent in the first continuous stirred tank reactor is (i) a compound of Formula (I), (ii) a compound of Formula (IV), or a mixture of (i) and (ii).
4. A process according to claim 1 , wherein R 1 is selected from the group consisting of CH 2 F, CHF 2 , CH 3 , C 2 H 5 and CF 3 .
5. A process according to claim 4 , wherein R 1 is CF 3 .
6. A process according to claim 1 , wherein R 2 is ethyl.
7. A process according to claim 1 , wherein R 3 is chlorine.
8. A process according to claim 1 , wherein an internal temperature of the first continuous stirred tank reactor is from −20° C. to +35° C.
9. A process according to claim 8 , wherein the internal temperature of the first continuous stirred tank reactor is from −10° C. to +10° C.
10. A process according to claim 1 , wherein the reaction mass from the first continuous stirred tank reactor is transferred to a plug-flow reactor before being transferred to the subsequent continuous stirred tank reactor.
11. A process according to claim 10 , wherein a residence time in the plug-flow reactor is from 15 minutes to three hours.
12. A process according to claim 10 , wherein an internal temperature of the plug-flow reactor is from 0° C. to +35° C.
13. A process according to claim 1 , wherein an internal temperature of the subsequent continuous stirred tank reactor is from +30° C. to +150° C.
14. A process according to claim 13 , wherein the internal temperature of the subsequent continuous stirred tank reactor is from +90° C. to +100° C.
15. A process according to claim 1 , wherein an internal pressure of the subsequent continuous stirred tank reactor is from 0 to 500 mbar.
16. A process according to claim 3 , wherein the concentration of the vinyl ether of Formula (III) in the reaction mass of said reacting step is 10% or less w/w.
17. A process according to claim 1 , wherein the concentration of the vinyl ether of Formula (III) in the reaction mass of said reacting step is 5% or less w/w.