Process for producing fluoroalkyl iodide
View Patent ↗To provide a process for producing a fluoroalkyl iodide, whereby the selectivity for a fluoroalkyl iodide having a desired degree of polymerization is high and the productivity is high. A process for producing a fluoroalkyl iodide (2) represented by R f CF 2 CF 2 I (wherein R f is a fluoroalkyl group having at most 4 carbon atoms), which comprises reacting a fluoroalkyl iodide (1) represented by R f I with tetrafluoroethylene in the presence of a radical initiator, wherein a first reaction step of supplying and reacting tetrafluoroethylene and a radical initiator to the fluoroalkyl iodide (1), is followed by repeating (n−1) times (provided that n is an integer of at least 3) a subsequent reaction step of supplying and reacting a radical initiator, or a radical initiator and tetrafluoroethylene, to a reaction mixture (1) formed in the first reaction step.
1. A process for producing a fluoroalkyl iodide (2) represented by formula (2), comprising:
a first reaction step of supplying and reacting tetrafluoroethylene and a radical initiator to a fluoroalkyl iodide (1) represented by formula (1), to thereby form a reaction mixture (1), followed by
a second reaction step of supplying and reacting a radical initiator, or a radical initiator and tetrafluoroethylene, to the reaction mixture (1) formed in the first reaction step, to thereby form a reaction mixture (2) comprising the fluoroalkyl iodide (1) represented by formula (1) and the fluoroalkyl iodide (2) represented by formula (2):
R f I (1)
R f CF 2 CF 2 I (2)
wherein
R f is a fluoroalkyl group having at most 4 carbon atoms,
the maximum amount of tetrafluoroethylene present in each reaction step is maintained to be within a range of from 0.01 to 10 mol % to the total number of moles of the fluoroalkyl iodide (1) and the fluoroalkyl iodide (2),
the maximum amount of the radical initiator present in each reaction step is adjusted to be from 0.0005 to 0.5 mol % to the total number of moles of the fluoroalkyl iodide (1) and the fluoroalkyl iodide (2), and
the conversion of the fluoroalkyl iodide (1) in the reaction mixture (2) after completion of the second reaction step is adjusted to be at most 10%.
2. The process according to claim 1 , which has, prior to each reaction step, a step of mixing the fluoroalkyl iodide (1) and/or the fluoroalkyl iodide (2), tetrafluoroethylene and the radical initiator by a stirrer.
3. The process according to claim 1 , which has a step (d) of separating the fluoroalkyl iodide (2) from the reaction mixture (2).
4. The process according to claim 1 , wherein the reaction temperature in each reaction step is from 40 to 120° C.
5. The process according to claim 1 , wherein after separating the fluoroalkyl iodide (2) from the reaction mixture (2), the fluoroalkyl iodide (1) is used as the fluoroalkyl iodide in the reaction step (1).
6. The process according to claim 1 , wherein the fluoroalkyl iodide (1) is C 4 F 9 I, or a mixture of C 4 F 9 I and C 2 F 5 I.
7. The process according to claim 1 , wherein the fluoroalkyl iodide (2) is C 6 F 13 I.
8. The process according to claim 1 , wherein the radical initiator is a fluorinated peroxide.
9. The process according to claim 1 , wherein the conversion of the fluoroalkyl iodide (1) is from 1.8 to 5%, and the selectivity for a fluoroalkyl iodide having at least 8 carbon atoms is at most 6%.
10. A process for producing a fluoroalkyl iodide (2) represented by formula (2), comprising:
a first reaction step of supplying and reacting tetrafluoroethylene and a radical initiator to a fluoroalkyl iodide (1) represented by formula (1), to thereby form a reaction mixture (n−1), followed by
a total of n reaction steps by repeating (n−1) times (provided that n is an integer of at least 3) a subsequent reaction step of supplying and reacting a radical initiator, or a radical initiator and tetrafluoroethylene, to the reaction mixture (n−1) formed in the preceding reaction step, to thereby form a reaction mixture (n) comprising the fluoroalkyl iodide (1) represented by formula (1) and the fluoroalkyl iodide (2) represented by formula (2)
R f I (1)
R f CF 2 CF 2 I (2)
wherein
R f is a fluoroalkyl group having at most 4 carbon atoms,
the maximum amount of tetrafluoroethylene present in each reaction step is maintained to be within a range of from 0.01 to 10 mol % to the total number of moles of the fluoroalkyl iodide (1) and the fluoroalkyl iodide (2),
the maximum amount of the radical initiator present in each reaction step is adjusted to be from 0.0005 to 0.5 mol % to the total number of moles of the fluoroalkyl iodide (1) and the fluoroalkyl iodide (2), and
the conversion of the fluoroalkyl iodide (1) in the reaction mixture (n) after completion of the n-th reaction step is adjusted to be at most 10%.
11. The process according to claim 10 , which has, prior to each reaction step, a step of mixing the fluoroalkyl iodide (1) and/or the fluoroalkyl iodide (2), tetrafluoroethylene and the radical initiator by a stirrer.
12. The process according to claim 10 , which has a step (d) of separating the fluoroalkyl iodide (2) from the reaction mixture (n) after completion of the n-th reaction step.
13. The process according to claim 10 , wherein the reaction temperature in each reaction step is from 40 to 120° C.
14. The process according to claim 10 , wherein after separating the fluoroalkyl iodide (2) from the reaction mixture (n), the fluoroalkyl iodide (1) is used as the fluoroalkyl iodide in the reaction step (1).
15. The process according to claim 10 , wherein the fluoroalkyl iodide (1) is C 4 F 9 I, or a mixture of C 4 F 9 I and C 2 F 5 I.
16. The process according to claim 10 , wherein the fluoroalkyl iodide (2) is C 6 F 13 I.
17. The process according to claim 10 , wherein the radical initiator is a fluorinated peroxide.
18. The process according to claim 10 , wherein the conversion of the fluoroalkyl iodide (1) is from 1.8 to 5%, and the selectivity for a fluoroalkyl iodide having at least 8 carbon atoms is at most 6%.