Method for preparing fluoroorganic compounds
AssigneeArkema France
InventorLaurent Wendlinger
Life of this patent
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Abstract
A process for preparing a compound of formula (I) HR1R2C—CF2—(C═O)—Y starting with a compound of formula (II) R1R2C═CX—(C═O)—Y or of formula (III) HR1R2C—CX1X2—(C═O)—Y placed in contact with hydrofluoric acid; R1 and R2 being independently selected from H, F, Cl, Br, I, C1-C20-alkyl, C6-C20-aryl and C2-C20-alkenyl, C3-C20-cycloalkenyl and C3-C20-cycloalkyl; X1 and X2 being independently selected from F, Cl, Br and I on condition that X1 and X2 are not simultaneously F; Y being selected from the group of H, C1-C20-alkyl, C1-C20-haloalkyl, C6-C20-aryl, —OH, —OR, —NH2, —NHR, —NR2, —SR, C3-C20-cycloalkyl, C3-C20-cycloalkenyl and C2-C20-alkenyl; R being independently selected from the group of C1-C20-alkyl, C6-C20-aryl and C2-C20-alkenyl, C3-C20-cycloalkenyl and C3-C20-cycloalkyl.
Claims13
A process for preparing a compound of formula (I) HR1R2C—CF2—(C═O)—Y, the process being carried out at a temperature of at least 30° C. and comprising the steps of:
- a) placing a compound of formula (II) R1R2C═CX1—(C═O)—Y or of formula (III) HR1R2C—CX1X2—(C═O)—Y in contact with hydrofluoric acid;
- R1 and R2 being independently selected from H, F, Cl, Br, I, C1-C20-alkyl, C6-C20-aryl and C2-C20-alkenyl, C3-C20-cycloalkenyl and C3-C20-cycloalkyl;
- X1 and X2 being independently selected from F, Cl, Br and I on condition that X1 and X2 are not simultaneously F;
- Y being selected from the group consisting of H, C1-C20-alkyl, C1-C20-haloalkyl, C6-C20-aryl, —OH, —OR, —NH2, —NHR, —NR2, —SR, C3-C20-cycloalkyl, C3-C20-cycloalkenyl and C2-C20-alkenyl;
- R being independently selected from the group consisting of C1-C20-alkyl, C6-C20-aryl and C2-C20-alkenyl, C3-C20-cycloalkenyl and C3-C20-cycloalkyl;
- and
- b) recovery of a stream A comprising said compound (1).
A composition comprising a compound of formula (V) R1R2C═CF—(C═O)—Y and optionally or not less than 500 ppm of water and optionally or not less than 500 ppm of hydrofluoric acid and optionally or not less than 100 ppm of a hydrogen halide other than hydrofluoric acid;
- with
- R1 and R2 being independently selected from H, F, Cl, Br, I, C1-C20-alkyl, C6-C20-aryl and C2-C20-alkenyl, C3-C20-cycloalkenyl and C3-C20-cycloalkyl;
- X1 being selected from Cl, Br and I;
- Y being selected from the group consisting of H, C1-C20-alkyl, C1-C20-haloalkyl, C6-C20-aryl, —OH, —NH2, —NHR, —NR2, —SR, C3-C20-cycloalkyl, C3-C20-cycloalkenyl and C2-C20-alkenyl;
- R being independently selected from the group consisting of C1-C20-alkyl, C6-C20-aryl and C2-C20-alkenyl, C3-C20-cycloalkenyl and C3-C20-cycloalkyl.
A process for preparing a compound of formula (I) HR1R2C—CF2—(C═O)—Y comprising the steps of:
- a) placing a compound of formula (II) R1R2C═CX1—(C═O)—Y or of formula (III) HR1R2C—CX1X2—(C═O)—Y in contact with only hydrofluoric acid and optionally a metal catalyst and/or a solvent;
- R1 and R2 being independently selected from H, F, Cl, Br, I, C1-C20-alkyl, C6-C20-aryl and C2-C20-alkenyl, C3-C20-cycloalkenyl and C3-C20-cycloalkyl;
- X1 and X2 being independently selected from F, Cl, Br and I on condition that X1 and X2 are not simultaneously F;
- Y being selected from the group consisting of H, C1-C20-alkyl, C1-C20-haloalkyl, C6-C20-aryl, —OH, —OR, —NH2, —NHR, —NR2, —SR, C3-C20-cycloalkyl, C3-C20-cycloalkenyl and C2-C20-alkenyl;
- R being independently selected from the group consisting of C1-C20-alkyl, C6-C20-aryl and C2-C20-alkenyl, C3-C20-cycloalkenyl and C3-C20-cycloalkyl;
- and
- b) recovery of a stream A comprising said compound (1).
A process comprising the steps of:
- a) placing the compound of formula (II) R1R2C═CX1—(C═O)—Y in contact with hydrofluoric acid under conditions that are effective for forming a compound of formula (V) R1R2C═CF—(C═O)—Y with:
- R1 and R2 being independently selected from H, F, Cl, Br, I, C1-C20-alkyl, C6-C20-aryl and C2-C20-alkenyl, C3-C20-cycloalkenyl and C3-C20-cycloalkyl;
- X1 being selected from Cl, Br and I;
- Y being selected from the group consisting of H, C1-C20-alkyl, C1-C20-haloalkyl, C6-C20-aryl, —OH, —OR, —NH2, —NHR, —NR2, —SR, C3-C20-cycloalkyl, C3-C20-cycloalkenyl and C2-C20-alkenyl;
- R being independently selected from the group consisting of C1-C20-alkyl, C6-C20-aryl and C2-C20-alkenyl, C3-C20-cycloalkenyl and C3-C20-cycloalkyl;
- and
- b) recovery of a stream A comprising said compound (1).
Dependencies are inferred from the claim text.