Method for preparation of imidodisulfuryl compounds
View Patent ↗The invention relates to a method for the preparation of imidodisulfuryl compounds in a continuous reaction at elevated temperatures.
1. A method for the preparation of a compound of formula (I);
the method comprising three consecutive steps comprising a step (StepS1), a step (StepS2) and a step (StepS3);
the step (StepS1) comprising a reaction (ReacS1);
wherein the reaction (ReacS1) is a reaction of a compound of formula (II) with a compound of formula (III);
wherein
X1 and X2 are identical or different and X1 and X2 are independently from each other selected from the group consisting of F, Cl, Br, I, C 1-6 perfluoroalkyl, and tolyl;
R n+ is selected from the group consisting of H + , Li + , Na + , K + , Mg 2+ , Ca 2+ , Zn 2+ , Cu 2+ , Al 3+ , Ti 3+ , Fe 2+ , Fe 3+ , B 3+ ,
[N(R20)(R21)(R22)R23] + , and [P(R20)(R21)(R22)R23] + ;
R20, R21, R22 and R23 are identical or different and R20, R21, R22 and R23 are independently from each other selected from the group consisting of H, C 1-8 alkyl, C 5-6 cycloalkyl, phenyl, benzyl, vinyl and ally; and
n is 1, 2 or 3;
wherein the reaction (ReacS1) is continuous;
wherein in the step (StepS1) a mixture of the compound of formula (II) and the compound of formula (III) passes through a device (DevS1), wherein the device (DevS1) is a continuously working device, and in the device (DevS1) the mixture of the compound of formula (II) and the compound of formula (III) is heated to a temperature (TempS1) of from 180 to 300° C. where the reaction (ReacS1) takes place, resulting in a reaction mixture,
wherein in step (StepS2) the reaction mixture from the device (DevS1) passes through a device (DevS2), wherein the device (DevS2) is a device for cooling the reaction mixture;
wherein in step (StepS3) the reaction mixture from the device (DevS2) passes through a device (DevS3), wherein the device (DevS3) is a device for back pressure regulation;
wherein the reaction mixture is cooled to a temperature (TempS2) of from 0 to 150° C. by the device (DevS2), the device (DevS3), or a combination thereof.
2. The method according to claim 1 , wherein the method further comprises
a step (StepS4), which is done after the step (StepS3), wherein in the step (StepS4) the reaction mixture from the device (DevS3) passes through a device (DevS4), wherein the device (DevS4) is a device for separating CO 2 from the reaction mixture.
3. The method according to claim 1 , wherein
X1 and X2 are identical and are selected from the group consisting of F, Cl, Br, C 1-6 perfluoroalkyl and tolyl.
4. The method according to claim 1 , wherein
R n+ is selected from the group consisting of H + , Li + , Na + , K + ,
and [N(R20)(R21)(R22)R23] + ;
R20, R21, R22 and R23 are identical or different and R20, R21, R22 and R23 are independently from each other selected from the group consisting of H, C 1-8 alkyl, C 5-6 cycloalkyl, phenyl, benzyl, vinyl and allyl.
5. The method according to claim 1 , wherein
the device (DevS1) is selected from the group consisting of a tube, a microreactor, a shell and tube heat exchanger, a plate heat exchanger and any device that can exchange heat from a reaction mixture.
6. The method according to claim 1 , wherein
the device (DevS2) is selected from the group consisting of a tube, a microreactor, a shell and tube heat exchanger, a plate heat exchanger and any device that can exchange heat from a reaction mixture.
7. The method according to claim 1 , wherein
the device (DevS3) is a back pressure regulating device.
8. The method according to claim 1 , wherein
the temperature (TempS1) is from 190 to 280° C.
9. The method according to claim 1 , wherein
the temperature (TempS2) is from 10 to 120° C.
10. The method according to claim 1 , wherein
the reaction (ReacS1) is done at a pressure (PressS1) of from 10 to 1000 bar.
11. The method according to claim 1 , wherein
a time (TimeS1) that the mixture is exposed to heating at the temperature (TempS1) in the device (DevS1) is from 0.5 sec to 4 h.
12. The method according to claim 1 , wherein
a time (TimeS2) that the mixture is cooled to the temperature (TempS2) is from 0.1 sec to 2 h.
13. The method according to claim 1 , wherein
the ratio of the molar amount of the compound of formula (III) to the molar amount of the compound of formula (II) is from 0.5:1 to 1.5:1.
14. A method for the preparation of a compound of formula (I);
the method comprising a reaction (ReacS1);
wherein the reaction (ReacS1) is a reaction of a compound of formula (II) with a compound of formula (III) at a temperature (TempS1) of from 180 to 300° C.;
wherein
X1 and X2 are identical or different and X1 and X2 are independently from each other selected from the group consisting of F, Cl, Br, I, C 1-6 perfluoroalkyl, and tolyl;
R n+ is selected from the group consisting of H + , Li + , Na + , K + , Mg 2+ , Ca 2+ , Zn 2+ , Cu 2+ , Al 3+ , Ti 3+ , Fe 2+ , Fe 3+ , B 3+ ,
[N(R20)(R21)(R22)R23] + , and [P(R20)(R21)(R22)R23] + ;
R20, R21, R22 and R23 are identical or different and R20, R21, R22 and R23 are independently from each other selected from the group consisting of H, C 1-8 alkyl, C 5-6 cycloalkyl, phenyl, benzyl, vinyl and allyl; and
n is 1, 2 or 3;
wherein the reaction (ReacS1) continuous, and
wherein the reaction (ReacS1) is done at a pressure (PressS1) of from 10 to 1000 bar.
15. The method according to claim 14 , wherein
the method comprises three consecutive steps comprising a step (StepS1), a step (StepS2) and a step (StepS3);
the step (StepS1) comprising the reaction (ReacS1) as defined in claim 14 ;
wherein in the step (StepS1) a mixture of the compound of formula (II) and the compound of formula (III) passes through a device (DevS1), wherein the device (DevS1) is a continuously working device, and in the device (DevS1) the mixture of the compound of formula (II) and the compound of formula (III) is heated to temperature (TempS1), where the reaction (ReacS1) takes place,
wherein in the step (StepS2) a device (DevS2) for cooling is employed;
wherein in the step (StepS3) a device (DevS3) for back pressure regulation is employed.
16. The method according to claim 15 , wherein the method further comprises
a step (StepS4), which is done after the step (StepS3), wherein in the step (StepS4) a device for separating CO 2 is employed.
17. The method according to claim 14 , wherein
X1 and X2 are identical and are selected from the group consisting of F, Cl, Br, C 1-6 perfluoroalkyl and tolyl.
18. The method according to claim 14 , wherein
R n+ is selected from the group consisting of H + , Li + , Na + , K + ,
and [N(R20)(R21)(R22)R23] + ;
R20, R21, R22 and R23 are identical or different and R20, R21, R22 and R23 are independently from each other selected from the group consisting of H, C 1-8 alkyl, C 5-6 cycloalkyl, phenyl, benzyl, vinyl and allyl.
19. The method according to claim 15 , wherein
the device (DevS1) is selected from the group consisting of a tube, a microreactor, a shell and tube heat exchanger, a plate heat exchanger and any device that can exchange heat from a reaction mixture.
20. The method according to claim 15 , wherein
the device (DevS2) is selected from the group consisting of a tube, a microreactor, a shell and tube heat exchanger, a plate heat exchanger and any device that can exchange heat from a reaction mixture.
21. The method according to claim 15 , wherein
the device (DevS3) is a back pressure regulating device.
22. The method according to claim 14 , wherein
the temperature (TempS1) is from 190 to 280° C.
23. The method according to claim 14 , wherein
the pressure (PressS1) is from 20 to 600 bar.
24. The method according to claim 15 , wherein
a time (TimeS1) that the mixture is exposed to heating at the temperature (TempS1) in the device (DevS1) is from 0.5 sec to 4 h.
25. The method according to claim 14 , wherein
the ratio of the molar amount of the compound of formula (III) to the molar amount of the compound of formula (II) is from 0.5:1 to 1.5:1.
26. The method according to claim 15 , wherein
the reaction (ReacS1) results in a reaction mixture,
wherein in the step (StepS2) the reaction mixture from the device (DevS1) passes through a device (DevS2);
wherein in the step (StepS3) the reaction mixture from the device (DevS2) passes through a device (DevS3);
wherein the reaction mixture is cooled by the device (DevS2), the (DevS3), or a combination thereof.
27. The method according to claim 26 , wherein
the reaction mixture is cooled to a temperature (TempS2) of from 0 to 150° C.
28. The method according to claim 16 , wherein
in the step (StepS4) the reaction mixture from the device (DevS3) passes through a device (DevS4).
29. The method according to claim 27 , wherein
the temperature (TempS2) is from 10 to 120° C.
30. The method according to claim 27 , wherein
a time (TimeS2) that the mixture is cooled to the temperature (TempS2) is from 0.1 sec to 2 h.