# US RE47,429 E1 · Process for producing chlorinated hydrocarbons > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US RE47,429 E1 - Document ID: USRE47429E1 - Status: Granted - Kind: E1 - Application number: 15/244,045 - Filed: 2016-08-23 - Granted: 2019-06-11 - Earliest claimed: 2013-01-22 - Assignees: Eagle US 2 LLC - Applicants: Axiall Ohio, Inc. - Inventors: Scott A. Sherwood; Stephen Robert Lester - Web page: https://patentgrep.com/patent/USRE47429E1 ## CPC - C07C 17/35: by reactions not affecting the number of carbon or of halogen atoms in the reaction - B01J 27/10: Chlorides - C07C 17/10: of hydrogen atoms (combined with addition of halogens to unsaturated hydrocarbons C07C17/06) - C07C 17/25: by splitting-off hydrogen halides from halogenated hydrocarbons - C07C 17/275: of hydrocarbons and halogenated hydrocarbons - C07C 19/01: containing chlorine - C07C 21/04: Chloro-alkenes - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS ## Abstract The preparation of chlorinated hydrocarbons, such as pentachloropropanes, such as 1,1,1,2,3-pentachloropropane, from tetrachloropropanes, such as 1,1,1,3-tetrachloropropane, in the presence of a polyvalent antimony compound that includes a pentavalent antimony compound, such as antimony pentachloride, is described. Also described are methods for preparing optionally chlorinated alkenes, such as, tetrachloropropenes, from chlorinated alkanes, such as pentachloropropanes, in the presence of ferric chloride and a polyvalent antimony compound that includes a pentavalent antimony compound. ## Claims ### Claim 1 A method of forming an alkene product 1,1,2,3-tetrachloropropene comprising, (1) reacting carbon tetrachloride with ethylene in the presence of an iron chloride, iron metal, and a trialkylphosphate to form 1,1,1,3-tetrachloropropane; (2) reacting the 1,1,1,3-tetrachloropropane with a source of chlorine in the presence of a polyvalent antimony compound comprising a pentavalent antimony compound, thereby forming a product comprising 1,1,1,2,3-pentachloropropane; (3) performing a dehydrochlorination reaction comprising, heating a chlorinated alkane substrate the 1,1,1,2,3-pentachloropropane in the presence of ferric chloride and a polyvalent antimony compound comprising a pentavalent antimony compound and a trivalent antimony compound, thereby forming a product comprising said alkene product 1,1,2,3-tetrachloropropene, wherein said alkene product optionally has at least one chlorine group covalently bonded thereto, and said chlorinated alkane substrate and said alkene product each have a carbon backbone structure that is in each case the same ferric chloride and the polyvalent antimony compound in each of steps (2) and (3) are each independently present in a catalytic amount. ### Claim 2 (depends on 1) The method of claim 1, wherein said polyvalent antimony compound comprises said pentavalent antimony compound and optionally a trivalent antimony compound, in step (3) said pentavalent antimony compound comprising comprises one or more pentavalent antimony compounds represented by the following Formula (I), Sb(R1)a(Cl)b (I) wherein the sum of a and b is 5, provided that b is at least 2, and R1 independently for each a is selected from the group consisting of linear, branched, or cyclic alkyl, and aryl, and said trivalent antimony compound comprising comprises one or more trivalent antimony compounds represented by the following Formula (II), Sb(R2)c(Cl)d (II) wherein the sum of c and d is 3, and R2 independently for each c is selected from the group consisting of linear, branched, or cyclic alkyl, and aryl. ### Claim 3 (depends on 2) The method of claim 2, wherein in step (3) said pentavalent antimony compound comprises antimony pentachloride, and said trivalent antimony compound comprises antimony trichloride. ### Claim 4 (depends on 1) The method of claim 1, wherein ferric chloride and said polyvalent antimony compound are each independently present in a catalytic amount. ### Claim 5 (depends on 1) The method of claim 1, wherein said method is performed as a batch method, a continuous method, and combinations thereof. ### Claim 6 (depends on 1) The method of claim 1 wherein, said chlorinated alkane substrate is 1,1,1,2,3-pentachloropropane, and said alkene product is 1,1,2,3-tetrachloropropene. ### Claim 7 (depends on 6) The method of claim 6 1, wherein heating 1,1,1,2,3-pentachloropropane in the presence of ferric chloride and said polyvalent antimony compound is conducted at a temperature of from 50° C. to 200° C., and a pressure of from 0.6 psia to 215 psia. ### Claim 8 (depends on 6) The method of claim 6 1, wherein heating 1,1,1,2,3-pentachloropropane in the presence of ferric chloride and said polyvalent antimony compound is conducted with a mole ratio of ferric chloride to polyvalent antimony compound of from 1000:1 to 1:1000. ### Claim 9 (depends on 1) The method of claim 1, wherein, heating the chlorinated alkane substrate 1,1,1,2,3-pentachloropropane in the presence of ferric chloride and the polyvalent antimony compound comprising the pentavalent antimony compound and the trivalent antimony compound, thereby forming the product comprising said alkene product 1,1,2,3-tetrachloropropene, is performed in a liquid phase. ### Claim 10 (depends on 1) The method of claim 1, wherein said source of chlorine is selected from chlorine (Cl2), sulfuryl chloride, and combinations thereof. ### Claim 11 (depends on 1) The method of claim 1, wherein said source of chlorine is chlorine (Cl2), and reacting 1,1,1,3-tetrachloropropane with said source of chlorine is conducted with a mole ratio of chlorine (Cl2) to 1,1,1,3-tetrachloropropane of 0.2:1 to 1.5:1. ### Claim 12 (depends on 1) The method of claim 1, wherein in step (2) said polyvalent antimony compound comprises said pentavalent antimony compound and optionally a trivalent antimony compound, said pentavalent antimony compound comprising one or more pentavalent antimony compounds represented by the following Formula (I), Sb(R1)a(Cl)b (I) wherein the sum of a and b is 5, provided that b is at least 2, and R1 independently for each a is selected from the group consisting of linear, branched, or cyclic alkyl, and aryl, and said trivalent antimony compound comprising one or more trivalent antimony compounds represented by the following Formula (II), Sb(R2)c(Cl)d (II) wherein the sum of c and d is 3, and R2 independently for each c is selected from the group consisting of linear, branched, or cyclic alkyl, and aryl. ### Claim 13 (depends on 12) The method of claim 12, wherein step (2) further comprises forming at least a portion of said pentavalent antimony compound from a precursor of said pentavalent antimony compound. ### Claim 14 (depends on 12) The method of claim 12, wherein in step (2) said trivalent antimony compound is selected from the group consisting of antimony trichloride, triphenyl antimony, and combinations thereof.