Method for producing an iodofluoroalkane compound
The present invention relates to a process for producing an iodofluoroalkane compound, comprising the steps of: a) placing a fluoroolefin in contact with hydrogen iodide to form a stream A comprising said iodofluoroalkane compound and unreacted hydrogen iodide, b) separating said stream A into a first stream B1 comprising said iodofluoroalkane compound and a stream B2 comprising unreacted hydrogen iodide, c) recycling stream B2 into step a).
1 . A process for producing an iodofluoroalkane compound, comprising the steps of:
a) placing a fluoroolefin in contact with hydrogen iodide to form a stream A comprising said iodofluoroalkane compound and unreacted hydrogen iodide,
b) separating said stream A into a first stream B1 comprising said iodofluoroalkane compound and a stream B2 comprising unreacted hydrogen iodide, and
c) recycling stream B2 into step a),
wherein step a) is performed in the gas phase and optionally performed with a catalyst, and
if step a) is performed in the presence of a catalyst, the catalyst is selected from the group consisting of an oxide, oxyhalide or halide of an element chosen from Li, Na, K, Cs, Mg, Cr and Ca.
2 . The process as claimed in claim 1 , characterized in that the hydrogen iodide is anhydrous.
3 . The process as claimed in claim 1 , characterized in that said fluoroolefin is anhydrous.
4 . The process as claimed in claim 1 , characterized in that said fluoroolefin is of formula (I) (R 1 )(R 2 )C═C(R 3 )(R 4 ) in which R 1 , R 2 , R 3 and R 4 are, independently of each other, selected from the group consisting of H, F, CI, I, a C 1 -C 10 alkyl radical optionally substituted with at least one fluorine atom, a C 3 -C 10 cycloalkyl radical optionally substituted with at least one fluorine atom, a C 2 -C 10 alkenyl radical optionally substituted with at least one fluorine atom, a C 3 -C 10 cycloalkenyl radical optionally substituted with at least one fluorine atom, and a C 6 -C 10 aryl radical optionally substituted with at least one fluorine atom; with the proviso that at least one of the substituents R 1 , R 2 , R 3 or R 4 is F or is a radical as defined above including at least one fluorine atom.
5 . The process as claimed in claim 4 , characterized in that said iodofluoroalkane compound is of formula (II) (R 1 )(R 2 )CH—C(I)(R 3 )(R 4 ) in which R 1 , R 2 , R 3 and R 4 are as defined in claim 4 .
6 . The process as claimed in claim 1 , characterized in that said fluoroolefin is of formula (I) (R 1 )(R 2 )C═C(R 3 )(R 4 ) in which R 1 , R 2 , R 3 and R 4 are, independently of each other, selected from the group consisting of H, F, I, a C 1 -C 5 perfluoroalkyl radical, a C 5 -C 10 perfluorocycloalkyl radical, a C 2 -C 5 perfluoroalkenyl radical, a C 5 -C 10 perfluorocycloalkenyl radical, a C 6 -C 10 perfluoroaryl radical; provided that at least one of the substituents R 1 , R 2 , R 3 or R 4 is F or is a perfluoro radical as defined above.
7 . The process as claimed in claim 6 , characterized in that said iodofluoroalkane compound is of formula (II) (R 1 )(R 2 )CH—C(I)(R 3 )(R 4 ) in which R 1 , R 2 , R 3 and R 4 are as defined in claim 6 .
8 . The process as claimed in claim 1 , characterized in that said fluoroolefin is of formula (I) (R 1 )(R 2 )C═C(R 3 )(R 4 ) in which R 1 , R 2 , R 3 and R 4 are, independently of each other, selected from the group consisting of H, F or Y 1 —[—C(Y 2 )(Y 3 )—] n — in which Y 1 , Y 2 and Y 3 are, independently of each other and independently for each unit n, selected from the group consisting of H and F; and n is an integer from 1 to 5; provided that at least one of the substituents R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 is F.
9 . The process as claimed in claim 8 , characterized in that said iodofluoroalkane compound is of formula (II) (R 1 )(R 2 )CH—C(I)(R 3 )(R 4 ) in which R 1 , R 2 , R 3 and R 4 are as defined in claim 8 .
10 . The process as claimed in claim 1 , characterized in that said fluoroolefin is selected from the group consisting of CHF═CH 2 , CF 2 ═CH 2 , CHF═CHF, CF 2 ═CHF, CF 2 ═CF 2 , CH 3 —CF═CH 2 , CH 3 —CH═CHF, CH 2 F—CH═CH 2 , CH 3 —CF═CHF, CH 2 F—CF═CH 2 , CH 3 —CH═CF 2 , CH 2 F—CH═CHF, CHF 2 —CH═CH 2 , CH 3 —CF═CF 2 , CH 2 F—CF═CHF, CHF 2 —CF═CH 2 , CH 2 F—CH═CF 2 , CHF 2 —CH═CHF, CF 3 —CH═CH 2 , CH 2 F—CF═CF 2 , CHF 2 —CF═CHF, CF 3 —CF═CH 2 , CHF 2 —CH═CF 2 , CF 3 —CH═CHF, CHF 2 —CF═CF 2 , CF 3 —CF═CHF, CF 3 —CH═CF 2 , and CF 3 —CF═CF 2 .
11 . The process as claimed in claim 1 , characterized in that said iodofluoroalkane compound is selected from the group consisting of CH 2 F—CH 2 I, CHFI—CH 3 , CHF 2 —CH 2 I, CF 2 I—CH 3 , CH 2 F—CHFI, CHF 2 —CHFI, CF 2 I—CH 2 F, CHF 2 —CF 2 I, CH 3 —CHF—CH 2 I, CH 3 —CFI—CH 3 , CH 3 —CH 2 —CHFI, CH 3 —CHI—CH 2 F, CH 2 F—CH 2 —CH 2 I, CH 3 —CHF—CHFI, CH 3 —CFI—CH 2 F, CH 2 F—CHF—CH 2 I, CH 3 —CH 2 —CF 2 I, CH 3 —CHI—CHF 2 , CH 2 F—CH 2 —CHFI, CH 2 F—CHI—CH 2 F, CHF 2 —CH 2 —CH 2 I, CH 3 —CHF—CF 2 I, CH 3 —CFI—CHF 2 , CH 2 F—CHF—CHFI, CH 2 F—CFI—CH 2 F, CHF 2 —CHF—CH 2 I, CH 2 F—CH 2 —CF 2 I, CH 2 F—CHI—CHF 2 , CHF 2 —CH 2 —CHFI, CF 3 —CH 2 —CH 2 I, CF 3 —CHI—CH 3 , CH 2 F—CHF—CF 2 I, CH 2 F—CFI—CHF 2 , CHF 2 —CHF—CHFI, CF 3 —CHF—CH 2 I, CF 3 —CFI—CH 3, CHF 2 —CH 2 —CF 2 I, CHF 2 —CHI—CHF 2 , CF 3 —CH 2 —CHFI, CF 3 —CHI—CH 2 F, CHF 2 —CHF—CF 2 I, CHF 2 —CFI—CHF 2 , CF 3 —CHF—CHFI, CF 3 —CFI—CH 2 F, CF 3 —CH 2 —CF 2 I, CF 3 —CHI—CHF 2 , CF 3 —CHF—CF 2 I, and CF 3 —CFI—CHF 2 .
12 . The process as claimed in claim 1 , characterized in that step a) also involves:
converting CF 2 ═CH 2 into CF 2 I—CH 3 ; or
converting CF 2 ═CHF into CF 2 I—CH 2 F; or
converting CF 2 ═CF 2 into CHF 2 —CF 2 I; or
converting CF 3 —CH═CH 2 into CF 3 —CH 2 —CH 2 I; or
converting CF 3 —CF═CH 2 into CF 3 —CFI—CH 3 ; or
converting CF 3 —CH═CHF into CF 3 —CH 2 —CHFI; or
converting CF 3 —CF═CHF into CF 3 —CHF—CHFI; or
converting CF 3 —CF═CF 2 into CF 3 —CHF—CF 2 I.
13 . The process as claimed in claim 1 , characterized in that said fluoroolefin has a boiling point below 100° C. at atmospheric pressure.
14 . The process as claimed in claim 1 , characterized in that step a) is performed at a temperature of from 150° C. to 700° C.
15 . A process for producing an iodofluoroalkane compound, comprising:
placing a fluoroolefin in contact with hydrogen iodide in the liquid phase in the presence of a solvent S1,
wherein said fluoroolefin is of formula (I) (R1)(R2)C═C(R3)(R4) in which R1, R2, R3 and R4 are, independently of each other, chosen from the group consisting of H, F, I, a C1-C5 perfluoroalkyl radical, a C5-C10 perfluorocycloalkyl radical, a C2-C5 perfluoroalkenyl radical, a C5-C10 perfluorocycloalkenyl radical, and a C6-C10 perfluoroaryl radical; provided that at least one of the substituents R1, R2, R3 or R4 is F or is a perfluoro radical as defined above;
wherein said fluoroolefin has a boiling point below 100° C. at atmospheric pressure;
wherein the solvent S1 has a boiling point of from 0° C. to 250° C. and is chosen from the group consisting of acetic acid, CC14, chloroform, dichloromethane, sulfolane, tetramethylene sulfone, N,N-dimethylformamide, dimethyl sulfoxide, N,N-dimethylacetamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, 1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone, and mixtures thereof;
wherein the process is performed in the presence of a catalyst chosen from alkali metal or alkaline-earth metal salts; and
wherein the process is performed at a temperature of from 50° C. to 280° C.
16 . The process as claimed in claim 15 , characterized in that the hydrogen iodide is anhydrous.
17 . The process as claimed in claim 15 , characterized in that said fluoroolefin is anhydrous.
18 . The process as claimed in claim 15 , characterized in that said fluoroolefin is of formula (I)(R 1 )(R 2 )C═C(R 3 )(R 4 ) in which R 1 , R 2 , R 3 and R 4 are, independently of each other, selected from the group consisting of H, F or Y 1 —[—C(Y 2 )(Y 3 )—] n — in which Y 1 , Y 2 and Y 3 are, independently of each other and independently for each unit n, selected from the group consisting of H and F; and n is an integer from 1 to 5; provided that at least one of the substituents R 1 , R 2 , R 3 , R 4 , Y 1 , Y 2 or Y 3 is F.
19 . The process of claim 15 , wherein the catalyst is an alkali metal salt.
20 . The process of claim 19 , wherein the catalyst is chosen from NaI, KI, and mixtures thereof.