Catalyzed hydrofluorination of alkenes

Claim 2

A process for the preparation of fluorinated alkanes which comprises contacting, at a temperature of about 0° C. to about 185° C., under substantially anhydrous conditions, one molar equivalent of an alkene selected from alkenes of the following formulas R.sup.1 R.sup.2 C═CR.sup.3 R.sup.4 and R.sup.5 R.sup.6 C═CR.sup.7 R.sup.8 wherein R 1 , R 2 , R 3 , R 4 and R 5 , R 6 , R 7 , R 8 are each selected from the group represented by C x Z 2x+1 , wherein Z is H, F, Br or Cl and wherein x=0 to 10; and at least one of the pairs R 5 and R 6 , R 7 and R 8 , R 5 and R 7 , and R 6 and R 8 taken together is --(CH 2 ) n --wherein "n" is an integer from 2 to 7 with the proviso that when R 5 and R 7 and/or R 6 and R 8 are trans, "n" must be 6 to 7, and when only two of the group R 5 R 6 , R 7 , R 8 are combined to form a cyclic structure the remaining two groups may be C x Z 2x+1 , wherein Z is H, F, Br or Cl and x=0 to 10, with HF in the presence of at least one catalyst consisting essentially of tantalum pentachloride or tantalum pentabromide to produce reaction products; removing said reaction products from contact with said catalyst and isolating a fluorinated alkane having one or more fluorine atoms above the number present in said alkene.

Claim 3

A process for the preparation of fluorinated alkanes which comprises contacting, at a temperature of about 0° C. to about 185° C., under substantially anhydrous conditions, one molar equivalent of a halogenated alkene selected from alkenes of the following formulas R.sup.1 R.sup.2 C═CR.sup.3 R.sup.4 and R.sup.5 R.sup.6 C═CR.sup.7 R.sup.8 wherein R 1 , R 2 , R 3 , R 4 and R 5 , R 6 , R 7 , R 8 are each selected from the group represented by C x Z 2x+1 , wherein Z is H, F, Br, or Cl and wherein X=0 to 10, with the proviso that in at least one of R 1 , R 2 , R 3 , R 4 , and R 4 and in at least one of R 5 , R 6 , R 7 and R 8 , Z is F, Br or Cl; and at least one of the pairs R 5 and R 6 , R 7 and R 8 , R 5 and R 7 , and R 6 and R 8 taken together is --(CH 2 ) n --wherein "n" is an integer from 2 to 7 with the proviso that when R 5 and R 7 and/or R 6 and R 8 are trans, "n" must be 6 to 7, and when only two of the group R 5 , R 6 , R 7 , R 8 are combined to form a cylic structure the remaining two groups may be C x Z 2x+1 , wherein Z is H, F, Br, or Cl and x=0 to 10, with HF in the presence of at least one catalyst consisting essentially of tantalum pentachloride or tantalum pentabromide to produce reaction products; removing said reaction products from contact with said catalyst and isolating a fluorinated alkane having one or more fluorine atoms above the number present in said alkene.

Claim 4

A process for the preparation of fluorinated alkanes which comprises contacting, at a temperature of about 0° C. to about 185° C., under substantially anhydrous conditions, one molar equivalent of a halogenated alkene selected from alkenes of the following formulas R.sup.1 R.sup.2 C═CR.sup.3 R.sup.4 and R.sup.5 R.sup.6 C═CR.sup.7 R.sup.8 wherein R 1 , R 2 , R 3 , R 4 and R 5 , R 6 , R 7 , R 8 are each selected from the group represented by C x Z 2x+1 , wherein Z is H, F, Br, or Cl and wherein X=0 to 10, with the proviso that in at least one of R 1 , R 2 , R 3 , R 4 , and R 4 and in at least one of R 5 , R 6 , R 7 and R 8 , Z is F, Br or Cl; and at least one of the pairs R 5 and R 6 , R 7 and R 8 , R 5 and R 7 , and R 6 and R 8 taken together is --(CH 2 ) n --wherein "n" is an integer from 2 to 7 with the proviso that when R 5 and R 7 and/or R 6 and R 8 are trans, "n" must be 6 to 7, and when only two of the group R 5 , R 6 , R 7 , R 8 are combined to form a cylic structure the remaining two groups may be C x Z 2x+1 , wherein Z is H, F, Br, or Cl and x=0 to 10, with HF in the presence of at least one catalyst consisting essentially of tantalum pentachloride or tantalum pentabromide to produce reaction products; removing said reaction products from contact with said catalyst and isolating a fluorinated alkane having one or more fluorine atoms above the number present in said alkene.

Claim 5

The process of claim 2 wherein the amount of HF is 1 to 30 molar equivalents.

Claim 6

The process of claim 2 wherein the catalyst is present in an amount of 0.001 to about 5 molar equivalents.

Claim 7

The process of claim 2 wherein the catalyst is tantalum pentachloride.

Claim 8

The process of claim 2 wherein the temperature is about 35° C. to 175° C.

Claim 9

The process of claim 2 wherein at least two of R 1 , R 2 , R 3 or R 4 are Cl.

Claim 10

The process of claim 2 wherein at least three of R 1 , R 2 , R 3 or R 4 are Cl.

Claim 11

The process of claim 2 wherein x=1-3.

Claim 12

The process of claim 2 wherein x=1.

Claim 13

The process of claim 2 wherein the amount of HF is 3-30 molar equivalents.

Claim 14

The process of claim 2 wherein the amount of HF is 5-30 molar equivalents.

Claim 15

The process of claim 2 wherein the alkene is selected from Cl 2 C═CCl 2 , HClC═CCl 2 , HFC═CF 2 , ClFC═CF 2 , H 2 C═CCl 2 , H 2 C═CF 2 , and H 2 C═CHCl.