# US 2019/0169100 A1 · Process for the dehydrochlorination of a chloroalkane > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2019/0169100 A1 - Document ID: US20190169100A1 - Status: Published application - Kind: A1 - Application number: 16/311,761 - Filed: 2017-06-22 - Published: 2019-06-06 - Earliest claimed: 2016-06-23 - Assignees: Blue Cube IP LLC - Applicants: Blue Cube IP LLC - Inventors: John D. Myers; Max Tirtowidjojo - Web page: https://patentgrep.com/patent/US20190169100A1 ## CPC - C07C 17/25: by splitting-off hydrogen halides from halogenated hydrocarbons - B01J 27/10: Chlorides - C07C 17/04: to unsaturated halogenated hydrocarbons - Y02P 20/10: Process efficiency - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS - Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS ## Abstract A process for the production of a chloroalkene that includes contacting a liquid phase chloroalkane with a solid catalyst, a catalyst deposited on a solid substrate, or combinations thereof, thereby causing the dehydrochlorination of the chloroalkane to produce a chloroalkene product and HCl. Processes for the production of 1,1,2,3-tetrachloropropene and 1,1,1,2,3-pentachloropropane are further provided. ## Claims ### Claim 1 A process for the production of a chloroalkene comprising: contacting a liquid phase first chloroalkane with a solid catalyst, a catalyst deposited on a solid substrate, or combinations thereof, and thereby causing dehydrochlorination of the first chloroalkane to produce a first chloroalkene product and HCl. ### Claim 2 (depends on 1) The process according to claim 1, wherein the catalyst comprises a metal chloride deposited on a substrate comprising carbon, alumina, silica, titania, an aluminosilicate, a zeolite, or combinations thereof. ### Claim 3 (depends on 1) The process according to claim 1, wherein the catalyst comprises a reduced (zero-valence) metal deposited on a substrate comprising carbon, alumina, silica, titania, an aluminosilicate, a zeolite, or combinations thereof. ### Claim 4 (depends on 1) The process according to claim 1, wherein the first chloroalkane comprises a chloropropane. ### Claim 5 (depends on 1) The process according to claim 1, wherein the first chloroalkane comprises 1,1,1,3-tetrachloropropane and the first chloroalkene product comprises 1,1,3-trichloropropene, 3,3,3-trichloropropene, 1,2,3-trichloropropene, or mixtures thereof. ### Claim 6 (depends on 1) The process according to claim 1, wherein the catalyst comprises ZnCl2, FeCl3, CuCl2, or combinations thereof, deposited on a carbon substrate. ### Claim 7 (depends on 1) The process according to claim 1, wherein the solid catalyst, a catalyst deposited on a solid substrate, or combinations thereof, comprises an aluminosilicate molecular sieve, a zeolite molecular sieve, a Y-type molecular sieve, a 13× molecular sieve, or combinations thereof. ### Claim 8 (depends on 1) The process according to claim 1, further comprising removing at least a portion of the first chloroalkene product as a gas or vapor. ### Claim 9 (depends on 1) The process according to claim 1, further comprising reacting at least a portion of the first chloroalkene product with a chlorinating agent to form at least some of a second chloroalkane product, wherein the first chloroalkane and the second chloroalkane are different. ### Claim 10 (depends on 9) The process according to claim 9, wherein the chlorinating agent comprises chlorine gas, liquid chlorine, sulfuryl chloride, or combinations thereof. ### Claim 11 (depends on 9) The process according to claim 9, further comprising dehydrochlorinating the second chloroalkane to produce at least some second chloroalkene. ### Claim 12 (canceled) ### Claim 13 (depends on 9) The process according to claim 9, wherein the second chloroalkane comprises a pentachloropropane. ### Claim 14 (depends on 11) The process according to claim 11, wherein the second chloroalkene comprises a tetrachloropropene. ### Claim 15 (depends on 13) The process according to claim 13, wherein the pentachloropropane is 1,1,1,2,3-pentachloropropane. ### Claim 16 (depends on 14) The process according to claim 14, wherein the tetrachloropropene is 1,1,2,3-tetrachloropropene. ### Claim 17 (depends on 1) The process according to claim 1, wherein the dehydrochlorination of the first chloroalkane and the chlorination of the first chloroalkene product occurs contemporaneously in the same vessel, in different sections of the same vessel, or in separate vessels. ### Claim 18 (depends on 1) The process according to claim 1, wherein dehydrochlorination of the first chloroalkane or second chloroalkane is conducted at a temperature of from about 0° C. to about 200° C. and at a pressure of from about 0 psig to about 200 psig. ### Claim 19 (depends on 1) The process according to claim 1, wherein at least a portion of the process is conducted in a reactor comprising a packed bed reactor, a packed bed column reactor, a continuous stirred tank reactor, a reactive distillation system, a shell and multitube reactor, or combinations thereof. ### Claim 20 (canceled) ### Claim 21 (canceled) ### Claim 22 (depends on 1) The process according to claim 1, further comprising removing at least some of the first chloroalkene product as a vapor and removing at least some of the first chloroalkane as a liquid. ### Claim 23 (depends on 11) The process according to claim 11, wherein the dehydrochlorination of the first chloroalkane or the second chloroalkane occurs in a reactive distillation system, the process further comprising removing at least some of the first chloroalkene product as a vapor and removing at least some of the first chloroalkane or the second chloroalkane as a liquid. ### Claim 24 (depends on 11) The process according to claim 11, wherein the solid catalyst, catalyst deposited on a solid substrate, or combinations thereof, is contained in at least a plurality of reactor tubes of a shell and multitube reactor, the process further comprising maintaining the dehydrochlorination of the first chloroalkane or the second chloroalkane at near-isothermal operating conditions by passing a heat transfer fluid across the outer surfaces of the reactor tubes. ### Claim 25 (canceled) ### Claim 26 A process for the production of 1,1,1,2,3-pentachloropropane comprising: contacting 1,1,1,3-tetrachloropropane in liquid phase with a solid catalyst, a catalyst deposited on a solid substrate, or combinations thereof, and thereby causing dehydrochlorination of the 1,1,1,3-tetrachloropropane to produce a trichloropropene product and HCl; and reacting at least a portion of the trichloropropene product with a chlorinating agent to form at least some 1,1,1,2,3-pentachloropropane. ### Claim 27 A process for the production of 1,1,2,3-tetrachloropropene comprising: contacting 1,1,1,3-tetrachloropropane in liquid phase with a solid catalyst, a catalyst deposited on a solid substrate, or combinations thereof, and thereby causing dehydrochlorination of the 1,1,1,3-tetrachloropropane to produce a trichloropropene product and HCl; reacting at least a portion of the trichloropropene product with a chlorinating agent to form at least some 1,1,1,2,3-pentachloropropane; and contacting the 1,1,1,2,3-pentachloropropane in liquid phase with a homogeneous catalyst, a solid catalyst, a catalyst deposited on a solid substrate, or combinations thereof, and thereby causing dehydrochlorination of the 1,1,1,2,3-pentachloropropane to produce at least some 1,1,2,3-tetrachloropropene. ### Claim 28 (canceled) ### Claim 29 (depends on 1) The process of claim 1, wherein the chloroalkene and/or the chloroalkane is converted to produce a fluorinated product.