# US 10,501,391 B2 · Process for producing butadiene from ethanol, comprising purification of a butadiene-loaded effluent by extractive distillation > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,501,391 B2 - Document ID: US10501391B2 - Status: Granted - Kind: B2 - Application number: 16/314,004 - Filed: 2017-06-26 - Published: 2019-06-06 - Granted: 2019-12-10 - Earliest claimed: 2016-06-29 - Assignees: Ifp Energies Nouvelles; Compagnie Generale Des Etablissements Michelin - Applicants: IFP Energies Nouvelles; Compagnie Generale des Establissements Michelin - Inventors: Sophie Couderc; Rejane Dastillung; Olivier Thinon - Web page: https://patentgrep.com/patent/US10501391B2 ## CPC - C07C 11/167: 1, 3-Butadiene - C07C 1/20: starting from organic compounds containing only oxygen atoms as heteroatoms - C07C 1/24: by elimination of water - C07C 7/005: {Processes comprising at least two steps in series} - C07C 7/04: by distillation - C07C 7/08: by extractive distillation - C07C 7/11: by absorption, i.e. purification or separation of gaseous hydrocarbons with the aid of liquids - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract The invention relates to a process for producing butadiene from an ethanol feedstock, comprising a step of converting the ethanol into butadiene, a distillation step, a step of washing with water, a butadiene purification step comprising at least one section for separating the 1-butene by extractive distillation and a final distillation section fed with the topped butadiene distillate, separating at the top a purified butadiene effluent and at the bottom a butene residue, and an effluent treatment step. ## Claims ### Claim 1 Process for producing butadiene from an ethanol feedstock comprising at least 80% by weight of ethanol, said process comprising: a) a step for converting the ethanol into butadiene, comprising: a water-ethanol separation section fed with at least a fraction of said ethanol feedstock and with a fraction of the ethanol-water effluent obtained from step e) and producing an ethanol effluent and a purged water effluent; a reaction section fed with said ethanol effluent and operated at a pressure of between 0.1 and 1.0 MPa and at a temperature of between 200 and 500° C. in the presence of a catalyst and producing a reaction effluent; b) a distillation step fed with the reaction effluent obtained from step a) and producing a polluted reagent residue and a butadiene distillate, operated at a pressure of between 0.1 and 1 MPa; c) a step of washing with water comprising at least one gas-liquid washing section fed at the bottom with the butadiene distillate obtained from step b) and at the top with a stream of water, and producing at the top a hydrated butadiene extract and at the bottom a spent water raffinate; d) a butadiene purification step fed with the butadiene extract obtained from step c) and producing at least one light gas effluent and a purified butadiene effluent comprising at least: a section for separating the 1-butene by extractive distillation fed with said butadiene extract and with a stream comprising a solvent, separating at the top a light gas effluent and, at the bottom a butadiene residue; a section for separating out the solvent by distillation fed with said butadiene residue obtained from the 1-butene separation section and separating at the top a topped butadiene distillate and at the bottom a solvent residue; a final distillation section fed with the topped butadiene distillate obtained from the solvent separation section, separating at the top a purified butadiene effluent and at the bottom a butene residue; e) an effluent treatment step fed with the spent water raffinate obtained from step c) and with the polluted reagent residue obtained from step b) and producing at least one ethanol-acetaldehyde effluent, an ethanol-water effluent and one or more brown oil effluents. ### Claim 2 (depends on 1) Process according to claim 1, wherein said water-ethanol separation section of said step a) is operated by distillation. ### Claim 3 (depends on 1) Process according to claim 1, wherein the ethanol effluent obtained from the water-ethanol separation section of step a) undergoes a purification step before being fed into the reaction section. ### Claim 4 (depends on 1) Process according to claim 1, wherein said reaction section of said step a) comprises two reaction zones, the first fed with a fraction of said ethanol effluent and optionally a part of said ethanol feedstock, and the second fed with the effluent from the first reaction zone, with the residual fraction of said ethanol effluent and with a fraction of the ethanol-acetaldehyde effluent obtained from step e) and optionally with a part of said ethanol feedstock, the ethanol/acetaldehyde mole ratio at the inlet of said second reaction zone being between 1 and 5. ### Claim 5 (depends on 4) Process according to claim 4, wherein a gas-liquid separation means is used between the two reaction zones to separate the effluent from the first reaction zone into a gaseous effluent and a liquid effluent, the liquid effluent feeding the second reaction zone. ### Claim 6 (depends on 1) Process according to claim 1, wherein the reaction effluent obtained from step a) undergoes a gas-liquid separation before feeding step b) consisting in cooling the reaction effluent obtained from step a) to a temperature of between 10 and 100° C. and to obtain, in a gas/liquid separator, at least one liquid effluent and at least one vapour effluent, the vapour effluent feeding the distillation step b) as reaction effluent obtained from step a), the liquid effluent feeding the effluent treatment step e). ### Claim 7 (depends on 1) Process according to claim 1, wherein the hydrated butadiene extract obtained from step c) is compressed to a pressure of between 0.1 and 1.0 MPa. ### Claim 8 (depends on 1) Process according to claim 1, wherein the solvent of said 1-butene separation section of said step d) is chosen from the group constituted by dimethylformamide, N-methylpyrrolidone and acetonitrile, and mixtures thereof. ### Claim 9 (depends on 1) Process according to claim 1, wherein said butadiene extract obtained from step c) is prewashed by placing in contact with a stream comprising a polar solvent chosen from the group constituted by dimethylformamide (DMF), N-methylpyrrolidone (NMP) and acetonitrile, prior to being fed into said 1-butene separation section. ### Claim 10 (depends on 1) Process according to claim 1, wherein said solvent residue from the solvent separation section of step d) feeds the 1-butene separation section of step d) as a stream comprising a solvent. ### Claim 11 (depends on 1) Process according to claim 1, wherein the topped butadiene distillate is treated, prior to being fed into the final distillation section of step d), in a second extractive distillation section, said second extractive distillation section being fed with said topped butadiene distillate and with a stream comprising a solvent and producing at the top the topped butadiene distillate feeding the final distillation section of step d), and at the bottom a spent solvent residue, said spent solvent residue feeding a second section for separating out the solvent by distillation, separating at the top a distillate of alkynes containing 4 carbon atoms and at the bottom a solvent residue. ### Claim 12 (depends on 11) Process according to claim 11, wherein said solvent residue obtained from the second solvent separation section feeds the second extractive distillation section as a stream comprising a solvent. ### Claim 13 (depends on 12) Process according to claim 12, wherein the solvent residue obtained from the solvent separation section and the solvent residue obtained from the second solvent separation section are mixed before feeding the 1-butene separation section and the second extractive distillation section.