Cyanuric chloride → Cyanuric fluoride

HRID 1155753Notes

Reaction equation

HRID 1155753 reaction equation
F.[F:2]C1N=C(Cl)N=C(Cl)N=1.[F:11][C:12]1[N:17]=[C:16]([F:18])[N:15]=[C:14](Cl)[N:13]=1.FC1N=C(Cl)N=C(Cl)N=1.N1C(Cl)=NC(Cl)=NC=1Cl>>[N:13]1[C:14]([F:2])=[N:15][C:16]([F:18])=[N:17][C:12]=1[F:11]

Participants

5

Reactant 4

HCID 7954Cyanuric chlorideHCID 20537880HCID 20537880, compoundHCID 232339542-Chloro-4,6-difluoro-1,3,5-triazineHCID 86738398HCID 86738398, compound

Product 1

HCID 12664Cyanuric fluoride

Procedure

If 2,4-difluoro-6-chloro-s-triazine or 2-fluoro-4,6-dichloro-s-triazine is used in place of cyanuric chloride as the starting material, very good yields of pure cyanuric fluoride are possible even with molar ratios of hydrogen fluoride/cyanuric halide which are lower than those mentioned above. For example, when 2,4-difluoro-6-chloro-s-triazine is used the reaction is advantageously carried out with a molar ratio of hydrogen fluoride/2,4-difluoro-6-chloro-s-triazine of 1:1 to 4:1, preferably about 2:1; if 2-fluoro-4,6-dichloro-s-triazine is used as the starting material, advantageous results are obtained with a molar ratio of hydrogen fluoride/2-fluoro-4,6-dichloro-s-triazine of 2:1 to 5:1 and preferably the reaction is carried out using a molar ratio of hydrogen fluoride/2-fluoro-4,6-dichloro-s-triazine of 3:1. When 2,4-difluoro-6-chloro-s-triazine or 2-fluoro-4,6-dichloro-s-triazine is used as the starting material, the reaction is also carried out at temperatures betwen 150° C. and 300° C.; preferably the reaction is carried out at between 180° C. and 220° C., as when cyanuric chloride is used as the starting material. Pure cyanuric fluoride is likewise obtaining in high yield when a mixture of 2,4-difluoro-6-chloro-s-triazine and 2-fluoro-4,6-dichloro-s-triazine or a mixture of cyanuric chloride, 2,4-difluoro-6-chloro-s-triazine and 2-fluoro-4,6-dichloro-s-triazine is employed, in place of cyanuric chloride, 2,4-difluoro-6-chloro-s-triazine or 2-fluoro-4,6-dichloro-s-triazine, as the starting material. In this case the most advantageous molar ratio of hydrogen fluoride/cyanuric halide mixture depends on the mixing ratio of the two or the three cyanuric halide components in the starting mixture. The most advantageous temperature range for the reaction when a mixture of cyanuric halides is used is the same as that when pure cyanuric chloride is employed as the starting material.

Workup

  1. customis also carried out at temperatures betwen 150° C. and 300° C.

Sources & evidence

ORD record
ord-2fe7bc83ac91415d8c9cc1f7abbfac96
Source dataset
uspto-grants-1982_06
Patent number
US04332939

Reaction notes

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