# US 10,865,348 B2 · Process which does simultaneous dehydrochlorination and hydrocracking of pyrolysis oils from mixed plastic pyrolysis while achieving selective hydrodealkylation of C9+ aromatics > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,865,348 B2 - Document ID: US10865348B2 - Status: Granted - Kind: B2 - Application number: 16/316,260 - Filed: 2017-06-08 - Published: 2019-08-01 - Granted: 2020-12-15 - Earliest claimed: 2016-07-13 - Assignees: Sabic Global Technologies B.V. - Applicants: SABIC Global Technologies B.V. - Inventors: Ravichander Narayanaswamy; Krishna Kumar Ramamurthy - Web page: https://patentgrep.com/patent/US10865348B2 ## CPC - C10G 47/02: characterised by the catalyst used - C10G 1/002: {in combination with oil conversion- or refining processes} - C10G 1/10: from rubber or rubber waste - C10G 45/08: in combination with chromium, molybdenum, or tungsten metals, or compounds thereof - C10G 47/00: Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions (C10G15/00 takes precedence; destructive hydrogenation of non-melting solid carbonaceous or similar materials C10G1/06) - C10G 47/04: Oxides - C10G 47/06: Sulfides - C10G 47/12: Inorganic carriers - C10G 47/14: the catalyst containing platinum group metals or compounds thereof - C10G 67/02: plural serial stages only - C10G 69/06: including at least one step of thermal cracking in the absence of hydrogen - C10G 2300/1003: Waste materials - C10G 2300/1096: Aromatics or polyaromatics - C10G 2300/202: Heteroatoms content, i.e. S, N, O, P - C10G 2300/703: Activation - 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 ## Abstract A process for hydrodealkylating a hydrocarbon stream comprising (a) contacting the hydrocarbon stream with a hydroprocessing catalyst in a hydroprocessing reactor in the presence of hydrogen to yield a hydrocarbon product, wherein the hydrocarbon stream contains C9+ aromatic hydrocarbons; and (b) recovering a treated hydrocarbon stream from the hydrocarbon product, wherein the treated hydrocarbon stream comprises C9+ aromatic hydrocarbons, wherein an amount of C9+ aromatic hydrocarbons in the treated hydrocarbon stream is less than an amount of C9+ aromatic hydrocarbons in the hydrocarbon stream due to hydrodealkylating of at least a portion of C9+ aromatic hydrocarbons from the hydrocarbon stream during the step (a) of contacting. ## Claims ### Claim 1 A process for hydrodealkylating a hydrocarbon stream comprising: (a) contacting the hydrocarbon stream with a hydroprocessing catalyst in a hydroprocessing reactor in the presence of hydrogen to yield a hydrocarbon product, wherein the hydrocarbon stream contains C9 aromatic hydrocarbons; and (b) recovering a treated hydrocarbon stream from the hydrocarbon product, wherein an amount of C9 aromatic hydrocarbons in the treated hydrocarbon stream is less than an amount of C9 aromatic hydrocarbons in the hydrocarbon stream due to hydrodealkylating of at least a portion of C9 aromatic hydrocarbons from the hydrocarbon stream during the step (a) of contacting; wherein the step (a) of contacting the hydrocarbon stream with a hydroprocessing catalyst is performed at (i) a temperature of 260° C. to 350° C.; (ii) a pressure of 10 barg to 45 barg; (iii) a weight hourly space velocity of about 0.1 hr-1 to about 10 hr-1; and (iv) a hydrogen to hydrocarbon ratio of 200 NL/L to 800 NL/L; wherein the hydroprocessing catalyst is activated in-situ and/or ex-situ by contacting the hydroprocessing catalyst with a stream containing sulphides and chlorides; wherein the hydroprocessing catalyst is activated for simultaneous dehydrochlorination, hydrocracking and hydrodealkylation; and wherein one or more chloride compounds are contained in and/or added to the hydrocarbon stream in an amount of 10 ppm chloride, based on a total weight of the hydrocarbon stream, and the treated hydrocarbon stream comprises one or more chloride compounds in an amount of less than 10 ppm chloride, based on a total weight of the treated hydrocarbon stream. ### Claim 2 (depends on 1) The process of claim 1, wherein the step (a) of contacting the hydrocarbon stream with a hydroprocessing catalyst is performed at (i) a temperature of 260° C. and (ii) a hydrogen to hydrocarbon ratio of 800 NL/L. ### Claim 3 (depends on 1) The process of claim 1, wherein the hydroprocessing catalyst is activated in-situ. ### Claim 4 (depends on 1) The process of claim 1, wherein the hydroprocessing catalyst comprises tungsten and molybdenum on an alumina support, platinum and palladium on an alumina support, nickel sulphides, nickel sulphides on an alumina support, molybdenum sulphides, molybdenum sulphides on an alumina support, or combinations thereof. ### Claim 5 (depends on 1) The process of claim 1, wherein one or more sulphides are contained in and/or added to the hydrocarbon stream in an amount effective to provide for a sulphur content of the hydrocarbon stream of from about 0.05 wt. % to about 5 wt. %, based on the total weight of the hydrocarbon stream. ### Claim 6 (depends on 1) The process of claim 1, further comprising feeding the treated hydrocarbon stream to a steam cracker. ### Claim 7 (depends on 6) The process of claim 6, wherein the treated hydrocarbon stream is characterized by a boiling end point of 370° C. ### Claim 8 (depends on 1) The process of claim 1, wherein the step (b) of recovering a treated hydrocarbon stream from the hydrocarbon product comprises (i) separating a treated product from a sulphur and chlorine-containing gas in a separator; and (ii) flowing the treated product in the treated hydrocarbon stream from the separator. ### Claim 9 (depends on 1) The process of claim 1, wherein the step (b) of recovering a treated hydrocarbon stream from the hydrocarbon product comprises: (i) separating an intermediate treated product from a sulphur and chlorine-containing gas in a separator; (ii) distilling the intermediate treated product in a distillation column to produce a treated hydrocarbon stream characterized by a boiling end point of less than about 370° C. and a heavy treated hydrocarbon stream characterized by a boiling end point of equal to or greater than about 370° C.; (iii) feeding at least a portion of the treated hydrocarbon stream to a steam cracker; and (iv) recycling at least a portion of the heavy treated hydrocarbon stream to the hydroprocessing reactor. ### Claim 10 (depends on 1) The process of claim 1, wherein the hydrocarbon stream further comprises C6-8 aromatic hydrocarbons and the treated hydrocarbon stream further comprises C6-8 aromatic hydrocarbons, and wherein an amount of C6-8 aromatic hydrocarbons in the treated hydrocarbon stream is greater than an amount of C6-8 aromatic hydrocarbons in the hydrocarbon stream. ### Claim 11 (depends on 1) The process of claim 1, wherein the hydrocarbon stream further comprises C6-8 aromatic hydrocarbons and heavy hydrocarbon molecules, and the treated hydrocarbon stream further comprises C6-8 aromatic hydrocarbons, and wherein an amount of C6-8 aromatic hydrocarbons in the treated hydrocarbon stream is increased by equal to or greater than at least 1 wt. % when compared to an amount of C6-8 aromatic hydrocarbons in the hydrocarbon stream. ### Claim 12 (depends on 1) The process of claim 1, wherein at least about 5 wt. % of the C9 aromatic hydrocarbons in the hydrocarbon stream are hydrodealkylated in step (a). ### Claim 13 (depends on 1) The process of claim 1, wherein the hydroprocessing catalyst comprises tungsten and molybdenum on an alumina support. ### Claim 14 (depends on 1) The process of claim 1, wherein the hydroprocessing catalyst comprises platinum and palladium on an alumina support. ### Claim 15 (depends on 1) The process of claim 1, wherein the hydroprocessing catalyst comprises nickel sulphides. ### Claim 16 A process for hydrodealkylating a hydrocarbon stream consisting of the steps of: (a) contacting the hydrocarbon stream with a hydroprocessing catalyst in a hydroprocessing reactor in the presence of hydrogen to yield a hydrocarbon product, wherein the hydrocarbon stream contains C9 aromatic hydrocarbons; and (b) recovering a treated hydrocarbon stream from the hydrocarbon product, wherein the treated hydrocarbon stream comprises C9 aromatic hydrocarbons, wherein an amount of C9 aromatic hydrocarbons in the treated hydrocarbon stream is less than an amount of C9 aromatic hydrocarbons in the hydrocarbon stream due to hydrodealkylating of at least a portion of C9 aromatic hydrocarbons from the hydrocarbon stream during the step (a) of contacting; wherein the step (a) of contacting the hydrocarbon stream with a hydroprocessing catalyst is performed at (i) a temperature of from 100° C.; (ii) a pressure of 1 bar absolute; (iii) a weight hourly space velocity of 0.1 hr−1; and (iv) a hydrogen to hydrocarbon ratio of 3,000 NL/L; and wherein the hydroprocessing catalyst is activated in-situ and/or ex-situ by contacting the hydroprocessing catalyst with a stream containing sulphides and chlorides and the hydroprocessing catalyst is activated for simultaneous dehydrochlorination, hydrocracking and hydrodealkylation.