A hydrofluoroolefin compound represented by the following general formula (II): Formula (II) where Rf is a linear, branched, or cyclic perfluoroalkyl group having 1-6 carbon atoms, and optionally comprises at least one catenated heteroatom selected from nitrogen or oxygen; n is 0 or 1; X is Cl or Br; with the following proviso: when Rf is CF3, then n is 1.

A hydrofluoroolefin compound represented by the following general formula (II): Formula (II) where Rf is a linear, branched, or cyclic perfluoroalkyl group having 1-6 carbon atoms, and optionally comprises at least one catenated heteroatom selected from nitrogen or oxygen; n is 0 or 1; X is Cl or Br; with the following proviso: when Rf is CF3, then n is 1.

A full continuous flow synthesis process of fluorine-containing aromatic hydrocarbon compounds. Aromatic amine and hydrogen fluoride are respectively pumped into thermostats A and B, then flow into micro-channel reactor C for salt forming reaction whose temperature is kept constant; sulfuric acid solution of nitrosylsulfuric acid is pumped into thermostat D; after keeping the temperature constant, the sulfuric acid solution of nitrosylsulfuric acid and salt forming product flowing out from the micro-channel reactor C flow into micro-channel reactor E for diazotization reaction; the obtained product flows into micro-channel reactor F for thermal decomposition reaction, is cooled in cooler G, then enters three-phase separator H for continuous separation, fluorine-containing aromatic hydrocarbon crude product is subjected to continuous alkaline washing, drying and rectification to obtain fluorine-containing aromatic hydrocarbon finished product, and mixture of hydrofluoric acid and sulfuric acid is continuously distilled to obtain hydrogen fluoride and sulfuric acid.

A full continuous flow synthesis process of fluorine-containing aromatic hydrocarbon compounds. Aromatic amine and hydrogen fluoride are respectively pumped into thermostats A and B, then flow into micro-channel reactor C for salt forming reaction whose temperature is kept constant; sulfuric acid solution of nitrosylsulfuric acid is pumped into thermostat D; after keeping the temperature constant, the sulfuric acid solution of nitrosylsulfuric acid and salt forming product flowing out from the micro-channel reactor C flow into micro-channel reactor E for diazotization reaction; the obtained product flows into micro-channel reactor F for thermal decomposition reaction, is cooled in cooler G, then enters three-phase separator H for continuous separation, fluorine-containing aromatic hydrocarbon crude product is subjected to continuous alkaline washing, drying and rectification to obtain fluorine-containing aromatic hydrocarbon finished product, and mixture of hydrofluoric acid and sulfuric acid is continuously distilled to obtain hydrogen fluoride and sulfuric acid.

Processes for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene and intermediates for producing same. A process for producing 2-chloro-1,1,1,4,4,4-hexafluorobutane comprises contacting 1,1,2,4,4-pentachlorobuta-1,3-diene with HF in the liquid phase in the presence of a fluorination catalyst. A process for producing 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane comprises contacting 2-chloro-1,1,1,4,4,4-hexafluorobutane with a chlorine source. A process for producing 1,1,1,4,4,4-hexafluoro-2-butyne comprises contacting 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane with a base. A process for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene comprises contacting 1,1,1,4,4,4-hexafluoro-2-butyne with hydrogen.

Processes for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene and intermediates for producing same. A process for producing 2-chloro-1,1,1,4,4,4-hexafluorobutane comprises contacting 1,1,2,4,4-pentachlorobuta-1,3-diene with HF in the liquid phase in the presence of a fluorination catalyst. A process for producing 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane comprises contacting 2-chloro-1,1,1,4,4,4-hexafluorobutane with a chlorine source. A process for producing 1,1,1,4,4,4-hexafluoro-2-butyne comprises contacting 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane with a base. A process for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene comprises contacting 1,1,1,4,4,4-hexafluoro-2-butyne with hydrogen.

A metal cyclopentadienyl complex has the formula:

##STR00001##

wherein m≥0; M is a Group I, II or III main group metal, alkali or transition metal; C.sub.5H.sub.4 represents a Cp ring where two hydrogens are substituted by M and R(F).sub.m; R(F).sub.m is connected to any one of the carbon atoms of the Cp and selected from a hydrocarbyl, fluorohydrocarbyl, silyl group [SiR′.sub.3], or amino group [—NR.sup.1R.sup.2]. The metal cyclopentadienyl complexes include Li(C.sub.5H.sub.4-2-C.sub.5H.sub.11) (CAS No: 2413046-23-6), K(C.sub.5H.sub.4-2-C.sub.5H.sub.11), Na(C.sub.5H.sub.4-2-C.sub.5H.sub.11), K(C.sub.5H.sub.4-1-F—C.sub.4H.sub.10), K(C.sub.5H.sub.4-1,1,1-3F—C.sub.4H.sub.6), Li(C.sub.5H.sub.4-2-C.sub.4H.sub.9), or In(C.sub.5H.sub.4-2-C.sub.5H.sub.11) (CAS No.: 2364634-67-1).

A mono-substituted cyclopentadiene has the formula:

##STR00002##

wherein m≥0; C.sub.5H.sub.5 represents the Cp ring where one hydrogen is substituted R(F).sub.m; R(F).sub.m is connected to any one of the carbon atoms of the Cp and selected from a hydrocarbyl, fluorohydrocarbyl, silyl group [SiR′.sub.3], or amino group [—NR.sup.1R.sup.2]. The mono-substituted cyclopentadienes include C.sub.5H.sub.5-1-F—C.sub.4H.sub.10, C.sub.5H.sub.5-2-C.sub.5H.sub.11, C.sub.5H.sub.5-2-C.sub.4H.sub.9, or C.sub.5H.sub.5-1,1,1-3F—C.sub.4H.sub.6.

A metal cyclopentadienyl complex has the formula:

##STR00001##

wherein m≥0; M is a Group I, II or III main group metal, alkali or transition metal; C.sub.5H.sub.4 represents a Cp ring where two hydrogens are substituted by M and R(F).sub.m; R(F).sub.m is connected to any one of the carbon atoms of the Cp and selected from a hydrocarbyl, fluorohydrocarbyl, silyl group [SiR′.sub.3], or amino group [—NR.sup.1R.sup.2]. The metal cyclopentadienyl complexes include Li(C.sub.5H.sub.4-2-C.sub.5H.sub.11) (CAS No: 2413046-23-6), K(C.sub.5H.sub.4-2-C.sub.5H.sub.11), Na(C.sub.5H.sub.4-2-C.sub.5H.sub.11), K(C.sub.5H.sub.4-1-F—C.sub.4H.sub.10), K(C.sub.5H.sub.4-1,1,1-3F—C.sub.4H.sub.6), Li(C.sub.5H.sub.4-2-C.sub.4H.sub.9), or In(C.sub.5H.sub.4-2-C.sub.5H.sub.11) (CAS No.: 2364634-67-1).

A mono-substituted cyclopentadiene has the formula:

##STR00002##

wherein m≥0; C.sub.5H.sub.5 represents the Cp ring where one hydrogen is substituted R(F).sub.m; R(F).sub.m is connected to any one of the carbon atoms of the Cp and selected from a hydrocarbyl, fluorohydrocarbyl, silyl group [SiR′.sub.3], or amino group [—NR.sup.1R.sup.2]. The mono-substituted cyclopentadienes include C.sub.5H.sub.5-1-F—C.sub.4H.sub.10, C.sub.5H.sub.5-2-C.sub.5H.sub.11, C.sub.5H.sub.5-2-C.sub.4H.sub.9, or C.sub.5H.sub.5-1,1,1-3F—C.sub.4H.sub.6.

Disclosed is a fluorination method comprising providing an aryl fluorosulfonate and a fluorinating reagent to a reaction mixture; and reacting the aryl fluorosulfonate and the fluorinating reagent to provide a fluorinated aryl species. Also disclosed is a fluorination method comprising providing, a salt comprising a cation and an aryloxylate, and SO.sub.2F.sub.2 to a reaction mixture; reacting the SO.sub.2F.sub.2 and the ammonium salt to provide a fluorinated aryl species. Further disclosed a fluorination method comprising providing a compound having the structure Ar—OH to a reaction mixture; where Ar is an aryl or heteroaryl; providing SO.sub.2F.sub.2 to the reaction mixture; providing a fluorinating reagent to the reaction mixture; reacting the SO.sub.2F.sub.2, the fluorinating reagent and the compound having the structure Ar—OH to provide a fluorinated aryl species having the structure Ar—F.

Disclosed is a fluorination method comprising providing an aryl fluorosulfonate and a fluorinating reagent to a reaction mixture; and reacting the aryl fluorosulfonate and the fluorinating reagent to provide a fluorinated aryl species. Also disclosed is a fluorination method comprising providing, a salt comprising a cation and an aryloxylate, and SO.sub.2F.sub.2 to a reaction mixture; reacting the SO.sub.2F.sub.2 and the ammonium salt to provide a fluorinated aryl species. Further disclosed a fluorination method comprising providing a compound having the structure Ar—OH to a reaction mixture; where Ar is an aryl or heteroaryl; providing SO.sub.2F.sub.2 to the reaction mixture; providing a fluorinating reagent to the reaction mixture; reacting the SO.sub.2F.sub.2, the fluorinating reagent and the compound having the structure Ar—OH to provide a fluorinated aryl species having the structure Ar—F.