Lewis acid catalyzed conjugated iodofluorination of fluoroolefins
First Claim
1. A process for the preparation of RCFICF2 X wherein R is selected from the group consisting of F and Cn F2n+1, n has a value of 1-10, X is selected from the group consisting of F and OR'"'"', and R'"'"' is a perfluoroalkyl containing up to about 10 carbon atoms, branched or straight, optionally containing in-chain ether oxygen, and having F, SO2 F, or CO2 CH3 as an end group, provided that when X is OR'"'"', R is F, which process comprises reacting a compound of the formula RCF═
- CFX where R, X and n are as defined above, with an ICl/HF mixture in the presence of a Lewis acid catalyst which increases the Ho acidity of HF of -11 to at least -13, at a temperature of from about 0°
to about 200°
C., wherein the Lewis acid catalyst is selected from the group consisting of BF3, TaF5 and NbF5, and wherein the yield of RCFICF2 X product is at least 50%.
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Abstract
A process for the preparation of perfluoroalkyl iodides, especially perfluoroethyl iodide, by reaction of perfluorinated compounds which contain a carbon carbon double bond with ICl in HF solvent in the presence of Lewis acid catalysts. The compounds are used as telogens for the telomerization of tetrafluoroethylene to long-chain perfluoroalkyl iodides.
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Citations
19 Claims
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1. A process for the preparation of RCFICF2 X wherein R is selected from the group consisting of F and Cn F2n+1, n has a value of 1-10, X is selected from the group consisting of F and OR'"'"', and R'"'"' is a perfluoroalkyl containing up to about 10 carbon atoms, branched or straight, optionally containing in-chain ether oxygen, and having F, SO2 F, or CO2 CH3 as an end group, provided that when X is OR'"'"', R is F, which process comprises reacting a compound of the formula RCF═
- CFX where R, X and n are as defined above, with an ICl/HF mixture in the presence of a Lewis acid catalyst which increases the Ho acidity of HF of -11 to at least -13, at a temperature of from about 0°
to about 200°
C., wherein the Lewis acid catalyst is selected from the group consisting of BF3, TaF5 and NbF5, and wherein the yield of RCFICF2 X product is at least 50%. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15)
- CFX where R, X and n are as defined above, with an ICl/HF mixture in the presence of a Lewis acid catalyst which increases the Ho acidity of HF of -11 to at least -13, at a temperature of from about 0°
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16. A process for the preparation of C2 F5 I comprising reacting tetrafluoroethylene with ICl/HF mixture in the presence of BF3.
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17. A process for the preparation of ICF2 CF2 OCF3 comprising reacting perfluoro-methyl vinyl ether with ICl/HF in the presence of BF3.
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18. A process for the preparation of ICF2 CF2 OCF2 CF2 CF3 comprising reacting perfluoro-n-propylvinyl ether with ICl/HF mixture in the presence of BF3.
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19. A process for the preparation of RCFICF2 X wherein R is selected from the group consisting of F and CnF2n+1, n has a value of 1-10, X is selected from the group consisting of F and OR'"'"', and R'"'"' is a perfluoroalkyl containing up to about 10 carbon atoms, branched or straight, optionally containing -n-chain ether oxygen, and having F, SO2 F, or CO2 CH3 as an end group, provided that when X is OR'"'"', R is F, which process comprises reacting a compound of the formula RCF═
- CFX where R, X and n are as defined above, with an ICl/HF mixture in the presence of a BF3 Lewis acid catalyst which increases the --Ho acidity of HF of 11 to at least 13 and and wherein the yield of RCFICF2 X product is at least 60%.
Specification