# US 2010/0168482 A1 · Processes for the production of fluoropropanes and halopropenes > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2010/0168482 A1 - Document ID: US20100168482A1 - Status: Published application - Kind: A1 - Application number: 12/444,462 - Filed: 2007-10-31 - Published: 2010-07-01 - Earliest claimed: 2006-10-31 - Assignees: E.I. du Pont de Nemours and Company - Inventors: Velliyur Nott Mallikarjuna Rao; Allen Capron Sievert - Web page: https://patentgrep.com/patent/US20100168482A1 ## CPC - C07C 17/21: with simultaneous increase of the number of halogen atoms - B01J 23/26: Chromium - C07C 17/06: combined with replacement of hydrogen atoms by halogens - C07C 17/10: of hydrogen atoms (combined with addition of halogens to unsaturated hydrocarbons C07C17/06) - C07C 17/206: {the other compound being HX} - C07C 17/25: by splitting-off hydrogen halides from halogenated hydrocarbons - C07C 19/08: containing fluorine - C07C 21/18: containing fluorine - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS ## Abstract A process is disclosed for making CF3CF2CH3, CF3CF═CH2 and/or CF3CCl═CH2. The process involves reacting at least one starting material selected from the group consisting of halopropanes of the formula CX3CH2CH2X, halopropenes of the formula CX3CH═CH2 and halopropenes of the formula CX2═CHCH2X, wherein each X is independently F or Cl, with HF and Cl2 in a reaction zone to produce a product mixture comprising HF, HCl, CF3CF2CH3, CF3CF═CH2, and CF3CCl═CH2; and recovering the CF3CF2CH3, CF3CF═CH2 and/or CF3CCl═CH2 from the product mixture. Also disclosed is a process for making CF3CH2CHF2, CF3CH═CHF, and/or CF3CH═CHCl. This process involves reacting at least one starting material selected from the group consisting of halopropenes of the formula CX3CH═CH2 and halopropenes of the formula CX2═CHCH2X, wherein each X is independently F or Cl, with HF and Cl2 in a reaction zone to produce a product mixture comprising HF, HCl, CF3CH2CHF2, CF3CH═CHF and CF3CH═CHCl; and recovering the CF3CH2CHF2, CF3CH═CHF, and/or CF3CH═CHCl from the product mixture. The molar ratio of HF to the total amount of starting materials fed to the reaction zone for both of these processes is at least stoichiometric, and the molar ratio of Cl2 to total amount of starting material fed to the reaction zone for both of these processes is 2:1 or less. ## Claims ### Claim 1 A process for making at least one product compound selected from the group consisting of CF3CF2CH3, CF3CF═CH2 and CF3CCl═CH2, comprising: reacting at least one starting material selected from the group consisting of halopropanes of the formula CX3CH2CH2X, halopropenes of the formula CX3CH═CH2 and halopropenes of the formula CX2═CHCH2X, wherein each X is independently selected from the group consisting of F and Cl, with HF and Cl2 in a reaction zone, optionally in the presence of a chlorofluorination catalyst, to produce a product mixture comprising HF, HCl, CF3CF2CH3, CF3CF═CH2 and CF3CCl═CH2, wherein the molar ratio of HF to total amount of starting material fed to the reaction zone is at least stoichiometric and wherein the molar ratio of Cl2 to total amount of starting material fed to the reaction zone is 2:1 or less; and recovering said at least one product compound from the product mixture. ### Claim 2 (depends on 1) The process of claim 1 wherein CF3CF═CH2 is recovered. ### Claim 3 (depends on 2) The process of claim 2 wherein CF3CF2CH3 from the product mixture is dehydrofluorinated to produce additional CF3CF═CH2. ### Claim 4 (depends on 1) The process of claim 1 wherein CF3CCl═CH2 from the product mixture is fluorinated to produce at least one of CF3CF═CH2 and CF3CF2CH3. ### Claim 5 (depends on 1) The process of claim 1 wherein the product mixture further comprises CF3CH═CHF; and wherein CF3CH═CHF from the product mixture is recovered. ### Claim 6 (depends on 1) The process of claim 1 wherein the product mixture further comprises CF3CH═CHCl; and wherein CF3CH═CHCl from the product mixture is fluorinated to produce at least one of CF3CH═CHF and CF3CH2CHF2. ### Claim 7 (depends on 1) The process of claim 1 wherein the product mixture further comprises CF3CH2CHF2; and wherein CF3CH2CHF2 from the product mixture is recovered. ### Claim 8 (depends on 1) The process of claim 1 wherein the product mixture further comprises CF3CH2CHF2; and wherein CF3CH2CHF2 from the product mixture is dehydrofluorinated to produce CF3CH═CHF. ### Claim 9 (canceled) ### Claim 10 (depends on 1) The process of claim 1 wherein the product mixture further comprises CF3CH═CHF; and wherein a mixture of CF3CF2CH3 and CF3CH═CHF is recovered and further reacted under dehydrofluorination conditions in the presence of a dehydrofluorination catalyst to produce a mixture comprising CF3CH═CHF and CF3CF═CH2. ### Claim 11 (canceled) ### Claim 12 (canceled) ### Claim 13 (depends on 1) The process of claim 1 wherein the product mixture further comprises CF3CH2CHF2 and CF3CH═CHCl, and wherein the CF3CCl═CH2, CF3CH2CHF2 and CF3CH═CHCl from the product mixture are further reacted with HF in the liquid phase under fluorination conditions in the presence of a fluorination catalyst to produce a mixture comprising CF3CH2CHF2 and CF3CF2CH3. ### Claim 14 (depends on 1) The process of claim 1 wherein the starting material is reacted in the vapor phase in the presence of a chlorofluorination catalyst. ### Claim 15 (depends on 14) The process of claim 14 wherein the chlorofluorination catalyst comprises at least one chromium-containing component selected from the group consisting of crystalline alpha-chromium oxide where from about 0.05 atom % to about 6 atom % of the chromium atoms in the alpha-chromium oxide lattice are replaced by trivalent cobalt atoms, and crystalline alpha-chromium oxide where from about 0.05 atom % to about 6 atom % of the chromium atoms in the alpha-chromium oxide lattice are replaced by trivalent cobalt atoms which has been treated with a fluorinating agent. ### Claim 16 A process for making at least one product compound selected from the group consisting of CF3CH2CHF2, CF3CH═CHF and CF3CH═CHCl, comprising: reacting at least one starting material selected from the group consisting of halopropenes of the formula CX3CH═CH2 and halopropenes of the formula CX2═CHCH2X wherein each X is independently selected from the group consisting of F and Cl, with HF and Cl2 in a reaction zone, optionally in the presence of a chlorofluorination catalyst, to produce a product mixture comprising HF, HCl, CF3CH2CHF2, CF3CH═CHF and CF3CH═CHCl, wherein the molar ratio of HF to total amount of starting material fed to the reaction zone is at least stoichiometric and wherein the molar ratio of Cl2 to total amount of starting material fed to the reaction zone is 2:1 or less; and recovering said at least one product compound from the product mixture. ### Claim 17 (depends on 16) The process of claim 16 wherein CF3CH═CHF is recovered. ### Claim 18 (depends on 17) The process of claim 17 wherein CF3CH2CHF2 from the product mixture is dehydrofluorinated to produce additional CF3CH═CHF. ### Claim 19 (depends on 16) The process of claim 16 wherein CF3CH═CHCl from the product mixture is fluorinated to produce at least one of CF3CH2CHF2 and CF3CH═CHF. ### Claim 20 (canceled) ### Claim 21 (depends on 16) The process of claim 16 wherein the product mixture further comprises CF3CF═CH2; and wherein CF3CF═CH2 from the product mixture is recovered. ### Claim 22 (canceled) ### Claim 23 (canceled) ### Claim 24 (canceled) ### Claim 25 (canceled) ### Claim 26 (canceled) ### Claim 27 (depends on 16) The process of claim 16 wherein the starting material is reacted in the vapor phase in the presence of a chlorofluorination catalyst. ### Claim 28 (canceled)