# US 7,411,108 B2 · Process for the removal of conjugated olefins from a monoolefin stream > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,411,108 B2 - Document ID: US7411108B2 - Status: Granted - Kind: B2 - Application number: 10/823,186 - Filed: 2004-04-12 - Published: 2004-12-23 - Granted: 2008-08-12 - Earliest claimed: 2000-06-30 - Assignees: Chevron Phillips Chemical Company LP - Inventors: Saleh A. Elomari; Richard N. Reynolds, Jr.; Steven J. Herron; Eduardo J. Baralt - Web page: https://patentgrep.com/patent/US7411108B2 ## CPC - C07C 7/14875: {with organic compounds (organo-metallic compounds C07C7/173)} - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract A method for removing conjugated olefins from a composition comprising contacting the composition with a Diels-Alder dienophile to convert conjugated olefins to a Diels-Alder adduct and arresting the Diels-Alder adduct. A method comprising confining a Diels-Alder dienophile to a first side of a selectively permeable barrier wherein the barrier is more permeable to conjugated olefins and less permeable to Diels-Alder dienophile and Diels-Alder adduct, and contacting a composition comprising mono-olefins and conjugated olefins with the Diels-Alder dienophile to form Diels-Alder adduct, wherein the contacting reduces the concentration of conjugated olefins in the composition. A method for removing conjugated olefins from a composition comprising bubbling the composition through a liquid comprising Diels-Alder dienophile to form a liquid comprising Diels-Alder adduct. A method for removing conjugated olefins from a non-solid composition comprising contacting the composition with a solid comprising Diels-Alder dienophile to form a solid comprising Diels-Alder adduct. ## Claims ### Claim 1 A method for removing conjugated olefins from a composition comprising: contacting the composition with a Diels-Alder dienophile to convert conjugated olefins to a Diels-Alder adduct; and arresting the Diels-Alder adduct via a selectively permeable barrier or a phase differential. ### Claim 2 (depends on 1) The method of claim 1 further comprising arresting the Diels-Alder dienophile. ### Claim 3 (depends on 1) The method of claim 1 wherein the selectively permeable barrier is a membrane. ### Claim 4 (depends on 1) The method of claim 1 wherein the Diels-Alder adduct is a solid and the composition is not a solid. ### Claim 5 (depends on 4) The method of claim 4 wherein the Diels-Alder dienophile comprises maleic anhydride, benzoquinone, or combinations thereof. ### Claim 6 (depends on 1) The method of claim 1 wherein the Diels-Alder adduct is a liquid and the composition is not a liquid. ### Claim 7 (depends on 1) The method of claim 1 wherein the selectively permeable barrier is disposed in a vessel. ### Claim 8 (depends on 7) The method of claim 7 wherein the selectively permeable barrier forms a removable container arresting the Diels-Alder adduct. ### Claim 9 (depends on 4) The method of claim 4 wherein the solids are disposed in a filter. ### Claim 10 (depends on 9) The method of claim 9 wherein the filter comprises alumina, activated carbon, or combinations thereof. ### Claim 11 (depends on 1) The method of claim 1 further comprising recovering a composition having a lower concentration of conjugated olefins. ### Claim 12 (depends on 11) The method of claim 11 wherein the recovered composition comprises less than or equal to about 80 parts per million by weight of conjugated olefins. ### Claim 13 (depends on 11) The method of claim 11 wherein the lower concentration of conjugated olefins is about 25 percent lower. ### Claim 14 (depends on 11) The method of claim 11 wherein the recovered composition comprises less than or equal to about 5 weight percent of Diels-Alder dienophile. ### Claim 15 (depends on 11) The method of claim 11 wherein the recovered composition comprises less than or equal to about 5 weight percent of Diels-Alder adduct. ### Claim 16 A method comprising: confining a Diels-Alder dienophile to a first side of a selectively permeable barrier wherein the barrier is more permeable to conjugated olefins and less permeable to Diels-Alder dienophile and Diels-Alder adduct; and contacting a composition comprising mono-olefins and conjugated olefins with the Diels-Alder dienophile to form Diels-Alder adduct; wherein the contacting reduces the concentration of conjugated olefins in the composition. ### Claim 17 (depends on 16) The method of claim 16 wherein the contacting further comprises exposing the composition to a second side of the barrier such that conjugated olefins permeate to the first side of the barrier. ### Claim 18 (depends on 17) The method of claim 17 wherein the contacting results in a lower concentration of conjugated olefins in the composition on the second side of the barrier. ### Claim 19 (depends on 18) The method of claim 18 wherein the Diels-Alder dienophile and Diels-Alder adduct are confined to the first side of the barrier. ### Claim 20 A method for removing conjugated olefins from a composition comprising: bubbling the composition through a liquid comprising Diels-Alder dienophile to form a liquid comprising Diels-Alder adduct; and arresting the Diels-Alder adduct via a selectively permeable barrier or a phase differential, wherein the bubbling and the arresting occur in a substantially common zone. ### Claim 21 A method for removing conjugated olefins from a non-solid composition comprising contacting the composition with a solid comprising Diels-Alder dienophile to form a solid comprising Diels-Alder adduct. ### Claim 22 (depends on 1) The method of claim 1 wherein the Diels-Alder dienophile and the Diels-Alder adduct do not mix homogenously with a bulk of the composition before, during, or after the contacting. ### Claim 23 (depends on 1) The method of claim 1 wherein the Diels-Alder adduct is arrested about simultaneously, about concurrently, about instantaneously, or about immediately following the formation of the Diels-Alder adduct. ### Claim 24 (depends on 1) The method of claim 1 wherein the composition further comprises mono-olefins. ### Claim 25 (depends on 20) The method of claim 20 wherein the composition further comprises mono-olefins. ### Claim 26 (depends on 1) The method of claim 1 wherein the Diels-Alder dienophile is maleic anhydride, derivatives of maleic anhydride, benzoquinone, derivatives of benzoquinone, dialkyl fumarates, dialkyl maleates, dialkylacetylenedicarboxylates, or combinations thereof. ### Claim 27 (depends on 1) The method of claim 1 wherein the Diels-Alder dienophile is maleic anhydride, dimethyl acetylene dicarboxylate, benzoquinone, or combinations thereof. ### Claim 28 (depends on 16) The method of claim 16 wherein the Diels-Alder dienophile is maleic anhydride, derivatives of maleic anhydride, benzoquinone, derivatives of benzoquinone, dialkyl fumarates, dialkyl maleates, dialkylacetylenedicarboxylates, or combinations thereof. ### Claim 29 (depends on 16) The method of claim 16 wherein the Diels-Alder dienophile is maleic anhydride, dimethyl acetylene dicarboxylate, benzoquinone, or combinations thereof. ### Claim 30 (depends on 20) The method of claim 20 wherein the Diels-Alder dienophile is maleic anhydride, derivatives of maleic anhydride, benzoquinone, derivatives of benzoquinone, dialkyl flimarates, dialkyl maleates, dialkylacetylenedicarboxylates, or combinations thereof. ### Claim 31 (depends on 20) The method of claim 20 wherein the Diels-Alder dienophile is maleic anhydride, dimethyl acetylene dicarboxylate, benzoquinone, or combinations thereof. ### Claim 32 (depends on 21) The method of claim 21 wherein the Diels-Alder dienophile is maleic anhydride, derivatives of maleic anhydride, benzoquinone, derivatives of benzoquinone, dialkyl fumarates, dialkyl maleates, dialkylacetylenedicarboxylates, or combinations thereof. ### Claim 33 (depends on 21) The method of claim 21 wherein the Diels-Alder dienophile is maleic anhydride, dimethyl acetylene dicarboxylate, benzoquinone, or combinations thereof.