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1. WO1992017626 - SYNTHESE ELECTROCHIMIQUE DE SELS DE DIARYLIODONIUM

Note: Texte fondé sur des processus automatiques de reconnaissance optique de caractères. Seule la version PDF a une valeur juridique

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CLAIMS

We Claim:

1. An electrolytic process for the preparation of a diaryliodonium salt comprising
(A) charging an electrolytic cell fitted with a
carbon anode and a cathode in a single
compartment with a reaction mixture comprising an iodoaryl compound, an aryl compound, a
stable electrolyte, and a solvent, and
(B) applying an electric potential to the cathode and anode under conditions to promote
formation of the desired diaryliodonium salt
product.

2. The process of Claim 1 wherein the electrolyte
functions partially or totally as the solvent.

3. The process of Claim 1 wherein said iodoaryl
compound contains 6 to 11 carbon atoms, and said aryl compound contains 6 to 11 carbon atoms.

4. The process of Claim 1 wherein said iodoaryl
compound is iodotoluene, iodobenzene, iodo—
naphthalene, or iodobenzene substituted with 1 to 5 substituents independently selected from —R,

—OR, and —C—O—R wherein R is an alkyl group of 1 to

12 carbon atoms; and said aryl compound is benzene, toluene, or naphthalene.

5. The process of Claim 1 wherein the solvent is
acetic acid.

6. The process of Claim 1 wherein the electrolyte
comprises sulfuric acid.

7. The process of Claim 5 wherein the electrolyte is a compound of fluorine, sulfuric acid or a
combination thereof.

8. The process of Claim 7 wherein the reaction mixture further comprises 1 to 10% of a drying agent, based on the total weight of the reaction mixture.

9. The process of Claim 8 wherein said compound of
fluorine is NH3HF or HF.

10. The process of Claim l wherein the molar ratio of the iodoaryl compound: aryl compound is 40:1 to
1:40; and the amount of electrolyte is 1% to 99%, said percentages being based on the total weight of the reaction mixture.

11. The process of Claim 1 wherein each aryl group of the diaryliodonium salt product is monosubstituted and the ratio of the yield of para, para
substituted product:ortho, para substituted product is greater than 5.

12. The process of Claim 7 wherein said ratio of the yield is greater than 20 and wherein the current efficiency is greater than 20.

13. The process of Claim 1 wherein the current
efficiency is greater than 75.

14. The process of Claim 1 wherein the cathode is
comprised of zinc, platinum, nickel, cadmium, tin, stainless steel, copper, vanadium, or carbon.

15. The process of Claim 1 wherein the cathode is
comprised of carbon.

16. The process of Claim 1 wherein the electric
potential is 1.8 to 2.2 volts.

17. The process of Claim 1 wherein the electric
potential is applied for a period of time of 2 to
10 hours, at a temperature of 15°C to 85°C.

18. The process of Claim 1 wherein the carbon anode is a graphitic carbon anode.

19. An electrolytic process for the preparation of a ditolyliodoniu fluoride comprising
(A) charging an electrolytic cell fitted with a
carbon anode and a cathode in a single
compartment with a reaction mixture comprising p—iodotoluene, toluene, an electrolyte
consisting essentially NH3HF, sulfuric acid,
or a mixture thereof, a solvent comprising
acetic acid, and a drying agent comprising
acetic anhydride, and
(B) applying an electric potential to the cathode and anode under conditions to promote
formation of the desired diaryliodonium salt
product.

20. The process of Claim 18 wherein said reaction
mixture comprises 0.5 to 20 weight % p—iodotoluene, 0.5 to 20 weight % toluene, 0.05 to 5 weight % of the electrolyte, 50 to 95 weight % acetic acid, and 0.01 to 10 weight % acetic anhydride.

21. The process of Claim 19 wherein the electrolyte consists essentially of NH3HF or 0.05 to 5 weight % HF plus 1 to 10 weight % sulfuric acid.

22. The process of Claim 19 wherein the carbon anode is a graphitic carbon anode.