# US 11,078,431 B2 · Modified ultra-stable Y (USY) zeolite catalyst for deolefinization of hydrocarbon streams > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,078,431 B2 - Document ID: US11078431B2 - Status: Granted - Kind: B2 - Application number: 16/715,555 - Filed: 2019-12-16 - Published: 2021-06-17 - Granted: 2021-08-03 - Earliest claimed: 2019-12-16 - Assignees: Saudi Arabian Oil Company; JGC Catalysts and Chemicals Ltd.; Japan Cooperation Center Petroleum - Applicants: Saudi Arabian Oil Company; JGC Catalysts and Chemicals Ltd.; Japan Cooperation Center, Petroleum - Inventors: Omer Refa Koseoglu; Robert Peter Hodgkins; Mitsunori Watabe; Tomoyasu Kagawa; Koji Uchida - Web page: https://patentgrep.com/patent/US11078431B2 ## CPC - C10G 29/20: Organic compounds not containing metal atoms - C10G 35/065: {containing crystalline zeolitic molecular sieves, other than aluminosilicates} - B01J 29/088: {Y-type faujasite} - C07C 2/66: Catalytic processes - C10G 35/24: Controlling or regulating of reforming operations - B01J 2229/183: in framework positions - C07C 2529/08: of the faujasite type, e.g. type X or Y - C07C 2529/16: containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium - C10G 2300/1096: Aromatics or polyaromatics - C10G 2300/4006: Temperature - C10G 2300/4012: Pressure - C10G 2300/4018: Spatial velocity, e.g. LHSV, WHSV - C10G 2400/30: Aromatics - Y02P 20/52: using catalysts, e.g. selective catalysts - 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 - B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS ## Abstract The present disclosure relates to a process for the deolefinization of hydrocarbon streams through an aromatic alkylation reaction by olefins, using a catalyst containing a framework-substituted zirconium and/or titanium and/or hafnium-modified ultra-stable Y (USY) type zeolite. ## Claims ### Claim 1 A process for deolefinization of a hydrocarbon feed containing aromatic compounds and olefins, the process comprising the step of contacting the hydrocarbon feed with a catalyst containing a framework-substituted ultra-stable Y (USY)-type zeolite in which a portion of aluminum atoms constituting a zeolite framework thereof is substituted with zirconium atoms and/or titanium and/or hafnium atoms, wherein the olefins alkylate the aromatic compounds in the hydrocarbon feed, thereby producing a deolefinated hydrocarbon product. ### Claim 2 (depends on 1) The process according to claim 1, wherein the framework-substituted USY-type zeolite in the catalyst comprises zirconium atoms and titanium atoms. ### Claim 3 (depends on 1) The process according to claim 1, wherein the framework-substituted USY-type zeolite in the catalyst comprises from about 0.1 to about 5% by mass zirconium and/or titanium and/or hafnium atoms, each calculated as the oxide basis. ### Claim 4 (depends on 1) The process according to claim 1, wherein the framework-substituted USY-type zeolite in the catalyst further includes a support comprising inorganic oxides selected from the group consisting of alumina, silica-alumina and combinations thereof. ### Claim 5 (depends on 1) The process according to claim 1, wherein the hydrocarbon feed comprises an aromatic rich hydrocarbon oil having a boiling point range of about 15° C. to about 500° C. ### Claim 6 (depends on 1) The process according to claim 1, wherein the contacting is operated at reaction temperature range of about 50° C. to about 250° C., a pressure of about 1 to about 30 bars and a liquid hourly space velocity (LHSV) of about 0.5 to about 50 h−1. ### Claim 7 (depends on 1) The process according to claim 1, wherein the deolefinated product contains less than about 500 ppm sulfur. ### Claim 8 (depends on 1) The process according to claim 1, wherein the deolefinated hydrocarbon product containing less than about 100 ppm nitrogen. ### Claim 9 (depends on 1) The process according to claim 1, wherein the hydrocarbon feed contains greater than about 1 wt % olefins. ### Claim 10 (depends on 1) The process according to claim 1, wherein the deolefinated hydrocarbon product contains less than about 10 wt % olefins. ### Claim 11 (depends on 1) The process according to claim 1, wherein the hydrocarbon feed is deolefinated at least about 95 wt %. ### Claim 12 (depends on 1) The process according to claim 1, wherein the deolefinated hydrocarbon product has bromine index less than about 60,000. ### Claim 13 (depends on 1) The process according to claim 1, wherein the aromatic compounds in the hydrocarbon feed contains benzene and alkylated benzenes. ### Claim 14 (depends on 13) The process according to claim 13, wherein the aromatic compounds in the hydrocarbon feed comprise C6 to C10 aromatic compounds. ### Claim 15 (depends on 1) The process according to claim 1, wherein the deolefinated hydrocarbon product comprises less olefin hydrocarbons and more alkylated aromatic compounds as compared with the hydrocarbon feed. ### Claim 16 (depends on 1) The process according to claim 1, wherein the hydrocarbon feed is fluid catalytic cracking (FCC) naphtha, coking naphtha or other naphtha coming from the cracking units in which no hydrogen is used. ### Claim 17 (depends on 1) The process according to claim 1, wherein the catalyst further includes an active metal selected from the group consisting of IUPAC Group 7 to 11 metal of the Periodic Table. ### Claim 18 (depends on 1) The process according to claim 1, wherein the deolefinated product contains less than about 10 ppm sulfur. ### Claim 19 (depends on 1) The process according to claim 1, wherein the deolefinated product contains less than about 0.5 ppm sulfur. ### Claim 20 (depends on 1) The process according to claim 1, wherein the deolefinated hydrocarbon product containing less than about 10 ppm nitrogen. ### Claim 21 (depends on 1) The process according to claim 1, wherein the deolefinated hydrocarbon product containing less than about 0.5 ppm nitrogen. ### Claim 22 (depends on 1) The process according to claim 1, wherein the deolefinated hydrocarbon product contains less than about 1 wt % olefins. ### Claim 23 (depends on 1) The process according to claim 1, wherein the deolefinated hydrocarbon product contains less than about 0.5 wt % olefins. ### Claim 24 (depends on 1) The process according to claim 1, wherein the hydrocarbon feed is deolefinated at least about 99 wt %. ### Claim 25 (depends on 1) The process according to claim 1, wherein the hydrocarbon feed is deolefinated at least about 99.99 wt %. ### Claim 26 (depends on 1) The process according to claim 1, wherein the deolefinated hydrocarbon product has bromine index less than about 10,000. ### Claim 27 (depends on 1) The process according to claim 1, wherein the deolefinated hydrocarbon product has bromine index less than about 1,000. ### Claim 28 A process for alkylating aromatic compounds in a hydrocarbon feed containing aromatic compounds and olefins, the process comprising the step of contacting the hydrocarbon feed with a catalyst containing framework-substituted ultra-stable Y (USY)-type zeolite in which a portion of aluminum atoms constituting a zeolite framework thereof is substituted with zirconium atoms and/or titanium and/or hafnium atoms, wherein the olefins alkylate the aromatic compounds in the hydrocarbon feed, thereby producing alkylated aromatic compounds.