# US 2023/0053833 A1 · Preparation of halogenated alkoxyethane > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2023/0053833 A1 - Document ID: US20230053833A1 - Status: Published application - Kind: A1 - Application number: 17/786,360 - Filed: 2019-12-19 - Published: 2023-02-23 - Earliest claimed: 2019-12-19 - Assignees: Commonwealth Scientific and Industrial Research Organisation - Applicants: Commonwealth Scientific and Industrial Research Organisation - Inventors: John TSANAKTSIDIS; Cecily ELDRIDGE; Scott COURTNEY - Web page: https://patentgrep.com/patent/US20230053833A1 ## CPC - B01J 19/2415: {Tubular reactors} - C07C 41/06: by addition of organic compounds only - B01J 19/0006: {Controlling or regulating processes (controlling or regulating in general G05)} - B01J 19/0053: {Details of the reactor} - B01J 19/1831: {spirally, concentrically or zigzag wound} - B01J 19/2405: {provoking a turbulent flow of the reactants, such as in cyclones, or having a high Reynolds-number} - B01J 19/2425: {in parallel} - B01J 19/243: {spirally, concentrically or zigzag wound} - C07C 41/38: by liquid-liquid treatment - B01J 2208/00026: Controlling or regulating the heat exchange system - B01J 2208/00557: controlling the residence time inside the reactor vessel - B01J 2219/00076: with heat exchange elements inside the reactor - B01J 2219/00245: Avoiding undesirable reactions or side-effects - B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract A process for continuous preparation of halogenated alkoxyethane of general formula XClHC—CF2OR, where X is —Cl or —F and OR is C1-4 alkoxy, the process comprising a step of introducing in a flow reactor reaction components comprising (i) a compound of general formula XClC═CF2, (ii) abase, and (iii) a C1-4 alkanol, wherein a) the flow reactor comprises one or more tubular flow line(s) having an internal cross-sectional area of less than 115 mm2 through which the reaction components flow as a reaction mixture, and b) the halogenated alkoxyethane is formed at least upon the reaction components mixing, with the so formed halogenated alkoxyethane flowing out of the flow reactor in a reactor effluent. ## Claims ### Claim 1 A process for continuous preparation of halogenated alkoxyethane of general formula XClHC—CF2OR, where X is —Cl or —F and OR is C1-4 alkoxy, the process comprising a step of introducing in a flow reactor reaction components comprising (i) a compound of general formula XClC═CF2, (ii) a base, and (iii) a C1-4 alkanol, wherein a) the flow reactor comprises one or more tubular flow line(s) having an internal cross-sectional area of less than 115 mm2 through which the reaction components flow as a reaction mixture, and b) the halogenated alkoxyethane is formed at least upon the reaction components mixing, with the so formed halogenated alkoxyethane flowing out of the flow reactor in a reactor effluent. ### Claim 2 (depends on 1) The process of claim 1, wherein the one or more tubular flow line(s) has/have an internal cross-sectional area of less than 30 mm2. ### Claim 3 (depends on 1, 2) The process of claim 1 or 2, wherein the one or more tubular flow line(s) has/have a circular internal cross-section. ### Claim 4 (depends on 3) The process of claim 3, wherein the one or more tubular flow line(s) has/have a diameter between 0.1 and 6 mm. ### Claim 5 (depends on 1, 2, 3, 4) The process of any one of claims 1-4, wherein the one or more tubular flow line(s) are provided in a coiled arrangement. ### Claim 6 (depends on 1, 2, 3, 4, 5) The process of any one of claims 1-5, wherein the one or more tubular flow line(s) has/have a total internal volume of at least 100 ml. ### Claim 7 (depends on 1, 2, 3, 4, 5, 6) The process of any one of claims 1-6, wherein the reactor effluent containing the halogenated alkoxyethane exits the reactor at a flow rate of at least 50 ml/min. ### Claim 8 (depends on 1, 2, 3, 4, 5, 6, 7) The process of any one of claims 1-7, wherein the reactor effluent contains at least 90% by volume of the halogenated alkoxyethane. ### Claim 9 (depends on 1, 2, 3, 4, 5, 6, 7, 8) The process of any one of claims 1-8, wherein the flow reactor provides a residence time of less than about 5 minutes. ### Claim 10 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9) The process of any one of claims 1-9, wherein the reaction mixture is obtained by mixing (i) a solution of the C1-4 alkanol and the base with (ii) the compound of general formula XClC═CF2. ### Claim 11 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10) The process of any one of claims 1-10, wherein the mixing is performed by combining (i) a flow of the solution of the C1-4 alkanol and the base with (ii) a flow of the compound of general formula XClC═CF2 according to a flow-rate ratio from 1:1 to 10:1. ### Claim 12 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11) The process of any one of claims 1-11, wherein the base is used in an amount of between 1% and 30% by weight relative to the total weight of base and C1-4 alkanol. ### Claim 13 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12) The process of any one of claims 1-12, wherein the compound of general formula XClC═CF2 is Cl2C═CF2 or FClC═CF2. ### Claim 14 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13) The process of any one of claims 1-13, wherein the C1-4 alkanol is selected from methanol (CH3OH), ethanol (CH3CH2OH), 1-propanol (CH3CH2CH2OH), 2-propanol ((CH3)2CHOH), 1-butanol (CH3CH2CH2CH2OH), 2-butanol (CH3CH2CHOHCH3), 2-methyl-1-propanol ((CH3)2CHCH2OH), 2-methyl-2-propanol ((CH3)3COH), and a combination thereof. ### Claim 15 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14) The process of any one of claims 1-14, wherein the halogenated alkoxyethane is Cl2HC—CF2OCH3 (methoxyflurane) or ClFHC—CF2OCH3. ### Claim 16 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15) The process of any one of claims 1-15, wherein the base comprises an alkali metal base cation or an ammonium base cation. ### Claim 17 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16) The process of any one of claims 1-16, wherein the base is used in substoichiometric amount relative to the compound of general formula XClC═CF2. ### Claim 18 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17) The process of any one of claims 1-17, wherein the base is selected from sodium hydroxide, potassium hydroxide, sodium methoxide, potassium methoxide, tetrabutylammonium hydroxide, benzyl(trimethyl)ammonium hydroxide, N-methyl-N,N,N-trioctylammonium chloride, tetraethylammonium hydroxide, tetramethylammonium hydroxide, and tetramethylphosphonium hydroxide. ### Claim 19 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18) The process of any one of claims 1-18, wherein water is added to the reactor effluent. ### Claim 20 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19) The process of any one of claims 1-19, further comprising a purification step in which the reactor effluent, or an organic phase derived from the reactor effluent and containing the halogenated alkoxyethane, is treated with an acid. ### Claim 21 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19) The process of any one of claims 1-19, further comprising a purification procedure that comprises, in the following order, the steps of: a) mixing the reactor effluent with a polar solvent to induce phase separation between a polar phase and an organic phase, b) separating the organic phase from the polar phase, c) treating the separated organic phase with an amine, d) washing the organic phase obtained in c) with an acid solution, e) desiccating the organic phase obtained in d), and f) distilling the organic phase obtained in e) to retrieve a purified distillate comprising the halogenated alkoxyethane. ### Claim 22 (depends on 20, 21) The process of claim 20 or 21, wherein the acid is selected from hydrochloric acid, sulfuric acid, sulphurous acid, methanesulfonic acid, trifluoromethanesulfonic acid, phosphoric acid, acetic acid, trifluoroacetic acid, nitric acid, nitrous acid, hypochlorous acid, chlorous acid, chloric acid, perchloric acid, and a combination thereof. ### Claim 23 (depends on 20, 21) The process of claim 20 or 21, wherein the acid is methanesulfonic acid.