# US 10,870,808 B2 · Isomerization and catalytic activation of pentane-enriched hydrocarbon mixtures > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,870,808 B2 - Document ID: US10870808B2 - Status: Granted - Kind: B2 - Application number: 16/855,312 - Filed: 2020-04-22 - Published: 2020-10-29 - Granted: 2020-12-22 - Earliest claimed: 2019-04-24 - Assignees: Phillips 66 Company - Applicants: Phillips 66 Company - Inventors: Anthony O. Baldridge; Neal D. McDaniel; James A. Suttil; Jianhua Yao; Edward C. Weintrob; Matthew J. Wulfers; Bruce B. Randolph; Maziar Sardashti - Web page: https://patentgrep.com/patent/US10870808B2 ## CPC - C10G 69/123: {alkylation} - C07C 5/2708: {with crystalline alumino-silicates, e.g. molecular sieves} - C07C 5/2775: {with crystalline alumino-silicates, e.g. molecular sieves} - C10G 45/64: containing crystalline alumino-silicates, e.g. molecular sieves - C10G 65/043: {at least one step being a change in the structural skeleton} - C10G 69/126: {polymerisation, e.g. oligomerisation} - C07C 5/22: by isomerisation (with simultaneous hydrogenation C07C5/13; with simultaneous dehydrogenation C07C5/373) - C07C 9/16: Branched-chain hydrocarbons - C07C 2529/40: of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11 - C10G 2300/1081: Alkanes - C10G: CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION (cracking to hydrogen or synthesis gas C01B; cracking or pyrolysis of hydrocarbon gases to individual hydrocarbons or mixtures thereof of definite or specified constitution C07C; cracking to cokes C10B); RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract Processes for producing liquid transportation fuels by converting a hydrocarbon feed stream comprising both isopentane and n-pentane. The hydrocarbon feed stream is separated into a first fraction that predominantly comprises isopentane and a second fraction that predominantly comprises n-pentane and some C6 paraffins. The first fraction is catalytically activated to an activation effluent comprising olefins and aromatics, while the second fraction is isomerized to convert at least a portion of the n-pentane to isopentane, then combined with the hydrocarbon feed stream to allow the newly-produced isopentane to be separated into the first fraction. The process yields products that are suitable for use as a blend component of liquid transportation fuels. ## Claims ### Claim 1 A method for converting a feed stream comprising pentanes to produce a blend component of liquid transportation fuel, the method comprising: a) providing a hydrocarbon feed stream comprising at least 50 wt. % pentanes, including both n-pentane and isopentane; b) at least partially separating the hydrocarbon feed stream in a separator to produce: a first fraction that comprises at least 80% of the isopentane present in the hydrocarbon feed stream (on a molar basis), and that further comprises at least 90% of hydrocarbons present in the hydrocarbon feed stream (on a molar basis) that are characterized by a vapor pressure equal to or greater than the vapor pressure of isopentane, and a second fraction that comprises at least 80% of the n-pentane content of the hydrocarbon feed stream (on a molar basis) and at least 90% of hydrocarbons from the hydrocarbon feed stream that contain six or more carbons (on a molar basis); Step c): contacting the first fraction with an activation catalyst at a temperature and a pressure that facilitates catalytic activation of at least a portion of the first fraction by the activation catalyst to produce an activation effluent comprising olefins containing from two to five carbon atoms, monocyclic aromatics and unconverted hydrocarbons containing from two to five carbon atoms; Step d): removing a first portion of the second fraction as the blend component of liquid transportation fuel; e) contacting a second portion the second fraction with at least one isomerization catalyst in an isomerization reactor that is maintained at a temperature and a pressure that facilitates the isomerization of at least a portion of n-pentane in the second fraction to produce isopentane, thereby producing an isomerization effluent characterized by an increased ratio of isopentane to n-pentane (on a wt. % basis) relative to the isopentane to n-pentane ratio of the hydrocarbon feed stream; f) combining the isomerization effluent with the hydrocarbon feed stream of a). ### Claim 2 (depends on 1) The method of claim 1, additionally comprising compressing and at least partially condensing the activation effluent to produce a liquid hydrocarbons fraction that comprises monocyclic aromatics and unreacted hydrocarbons containing at least five carbon atoms, and a compressed light hydrocarbons fraction that comprises hydrogen and at least 80 wt. % hydrocarbons containing four or less carbon atoms. ### Claim 3 (depends on 2) The method of claim 2, further comprising separating the liquid hydrocarbons fraction into an liquid hydrocarbon product and an unreacted C5/C6 hydrocarbons fraction, wherein the liquid hydrocarbon product comprises monocyclic aromatics the unreacted C5/C6 hydrocarbons fraction comprises alkanes and olefins containing from five to six carbons. ### Claim 4 (depends on 3) The method of claim 3, wherein the unreacted C5/C6 hydrocarbons fraction is mixed with the hydrocarbon feed stream of a). ### Claim 5 (depends on 2) The method of claim 2, wherein the compressed light hydrocarbons fraction is separated to produce a hydrogen stream and a light paraffins stream comprising paraffins containing four or less carbon atoms. ### Claim 6 (depends on 5) The method of claim 5, further comprising adding a diluent to the first fraction prior to the contacting of c), wherein the diluent is characterized as less chemically reactive with the activation catalyst than the first fraction at the conditions of temperature and pressure that are maintained in the activation reactor and wherein at least a portion of the light paraffins stream is mixed with the first fraction and serves as the diluent. ### Claim 7 (depends on 1) The method of claim 1, wherein the hydrocarbon feed stream comprises at least 70 wt. % pentanes. ### Claim 8 (depends on 1) The method of claim 1, wherein the activation catalyst comprises one or more zeolites characterized by a Si/Al ratio ranging from 12 to 80. ### Claim 9 (depends on 1) The method of claim 1, wherein the activation catalyst comprises ZSM-5 zeolite. ### Claim 10 (depends on 1) The method of claim 1, wherein the activation catalyst facilitates carbon-hydrogen bond activation that leads to at least one of olefination, dimerization, oligomerization and aromatization of the first fraction. ### Claim 11 (depends on 1) The method of claim 1, wherein the temperature in the activation reactor is maintained at a temperature in the range from 500° C. to 625° C. and a pressure in the range from 15 psig to 100 psig. ### Claim 12 (depends on 1) The method of claim 1, wherein the temperature in the activation reactor is maintained at a temperature in the range from 550° C. to 600° C. and a pressure in the range from 20 psig to 60 psig. ### Claim 13 (depends on 1) The method of claim 1, wherein the temperature in the activation reactor is maintained at a temperature in the range from 550° C. to 575° C. and a pressure in the range from 20 psig to 50 psig. ### Claim 14 (depends on 1) The method of claim 1, further comprising adding a diluent to the first fraction prior to the contacting of c), wherein the diluent is characterized as less chemically reactive with the activation catalyst than the first fraction at the conditions of temperature and pressure that are maintained in the activation reactor. ### Claim 15 (depends on 14) The method of claim 14, wherein the diluent is added in an amount that alters the specificity of the activation catalyst to increase the production of olefins, decrease the production of aromatics, or combinations thereof, thereby increasing the ratio of olefins to aromatics in the activation effluent. ### Claim 16 (depends on 14) The method of claim 14, wherein the diluent is added in an amount that is effective to produce an activation effluent that is characterized by an olefins to aromatics ratio in the range of 0.5 to 2.0. ### Claim 17 (depends on 14) The method of claim 14, wherein the diluent is added in an amount that is effective to produce an activation effluent that is characterized by an olefins to aromatics ratio in the range of 0.5 to 1.0. ### Claim 18 (depends on 14) The method of claim 14, wherein the diluent is selected from at least one of methane, ethane, propane and butane isomers. ### Claim 19 (depends on 1) The method of claim 1, further comprising adding a diluent to the first fraction prior to the contacting of c), wherein the diluent is characterized as chemically non-reactive with the activation catalyst at the conditions of temperature and pressure that are maintained in the activation reactor. ### Claim 20 (depends on 1) The method of claim 1, wherein wherein step e) comprises multiple isomerization reactors that are arranged in series configuration, wherein each of the multiple reactors contains at least one isomerization catalyst and is maintained at a temperature and a pressure that facilitates the isomerization of n-pentane to isopentane by the at least one isomerization catalyst.