# US 5,344,806 A · Process for producing monoalkenyl aromatic hydrocarbon compound > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,344,806 A - Document ID: US5344806A - Status: Granted - Kind: A - Application number: 08/011,216 - Filed: 1993-01-29 - Granted: 1994-09-06 - Earliest claimed: 1992-03-03 - Assignees: Mitsubishi Gas Chemical Company, Inc. - Inventors: Norio Fushimi; Kenji Inamasa; Makoto Takagawa - Web page: https://patentgrep.com/patent/US5344806A ## CPC - B01J 23/04: Alkali metals - C07C 2/72: Addition to a non-aromatic carbon atom of hydrocarbons containing a six-membered aromatic ring - C07C 2521/10: Magnesium; Oxides or hydroxides thereof - C07C 2523/02: of the alkali- or alkaline earth metals or beryllium - C07C 2523/04: Alkali metals - B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract There is disclosed a process for producing a monoalkenyl aromatic hydrocarbon compound which comprises alkenylating a side chain of an aromatic hydrocarbon compound having at least one hydrogen atom bonded at .alpha.-position of the side chain (such as xylene) with a conjugated diene having 4 or 5 carbon atoms (such as butadiene) in the presence of a catalyst comprising the mixture obtained by heat treating metallic sodium together with an alkaline earth metal oxide containing a potassium compound in the atmosphere of an inert gas. According to the aforesaid process, a monoalkenyl aromatic hydrocarbon compound such as industrially useful monoalkenylbenzene can be produced in high yield at a low cost with enhanced safety from a specific aromatic hydrocarbon compound and a specific conjugated diene compound. ## Claims ### Claim 1 A process for producing a monoalkenyl aromatic hydrocarbon compound which comprises alkenylating a side chain of an aromatic hydrocarbon compound having at least one hydrogen atom bonded at .alpha.-position of the side chain with a conjugated diene having 4 or 5 carbon atoms in the presence of a catalyst comprising the mixture obtained by heat treating metallic sodium together with a mixture of an alkaline earth metal oxide and a potassium compound selected from the group consisting of potassium hydroxide, potassium carbonate and potassium hydrogen carbonate in an inert gas atmosphere. ### Claim 2 (depends on 1) The process according to claim 1 wherein the alkaline earth metal oxide is magnesium oxide. ### Claim 3 (depends on 1) The process according to claim 1 wherein the alkaline earth metal oxide is calcium oxide. ### Claim 4 (depends on 1) The process according to claim 1 wherein the alkaline earth metal oxide containing a potassium compound contains 0.001 to 5 parts by weight of said potassium compound in terms of metallic potassium per one part by weight of said alkaline earth metal oxide. ### Claim 5 (depends on 1) The process according to claim 1 wherein the atomic ratio of the metallic sodium to the metallic potassium in the potassium compound is 0.01 to 10. ### Claim 6 (depends on 1) The process according to claim 1 wherein the aromatic hydrocarbon compound having at least one hydrogen atom bonded at .alpha.-position of a side chain is selected from the group consisting of monoalkylbenzene, dialkylbenzene, trialkylbenzene, tetraalkylbenzene, pentaalkylbenzene, hexaalkylbenzene, monoalkylnaphthalene, dialkylnaphthalene, tetrahydronaphthalene and indane. ### Claim 7 (depends on 1) The process according to claim 1 wherein the conjugated diene having 4 or 5 carbon atoms is selected from the group consisting of 1,3-butadiene; 1,3-pentadiene; and isoprene. ### Claim 8 (depends on 1) The process according to claim 1 wherein the molar ratio of the conjugated diene having 4 or 5 carbon atoms to the aromatic hydrocarbon compound having at least one hydrocarbon atom bonded at .alpha.-position of a side chain is 0.01 to 1. ### Claim 9 (depends on 1) The process according to claim 1 wherein the catalyst is used in alkenylation in an amount of at least 0.01% by weight based on the aromatic hydrocarbon compound having at least one hydrocarbon atom bonded at .alpha.-position of a side chain. ### Claim 10 (depends on 1) The process according to claim 1 wherein said aromatic hydrocarbon compound having at least one hydrogen atom bonded at .alpha.-position of a side chain is selected from the group consisting of monoalkylbenzene, dialkylbenzene, trialkylbenzene, tetraalkylbenzene, pentaalkylbenzene, hexaalkylbenzene, monoalkylnaphthalene, dialkylnaphthalene, tetrahydronaphthalene and indane; said conjugated diene having 4 or 5 carbon atoms is selected from the group consisting of 1,3-butadiene; 1,3-pentadiene; and isoprene; the molar ratio of said conjugated diene having 4 or 5 carbon atoms to said aromatic hydrocarbon compound having at least one hydrocarbon atom bonded at .alpha.-position of a side chain is 0.01 to 1; said catalyst is in an amount of at least 0.01% by weight based on said aromatic hydrocarbon compound having at least one hydrocarbon atom bonded at .alpha.-position of a side chain; in said catalyst, the atomic ratio of the metallic sodium to the metallic potassium in the potassium compound is 0.01 to 10; and said mixture of the alkaline earth metal oxide and a potassium compound contains 0.001 to 5 parts by weight of said potassium compound in terms of metallic potassium per one part by weight of said alkaline earth metal oxide. ### Claim 11 (depends on 10) The process according to claim 10, wherein said molar ratio is 0.03 to 0.5; said catalyst is in an amount of at least 0.05% based on said aromatic hydrocarbon compound; said atomic ratio of metallic sodium to metallic potassium is 0.02 to 5; said mixture of the alkaline earth metal oxide and a potassium compound contains 0.002 to 2 parts of said potassium compound in terms of metallic potassium per one part of said alkaline earth metal oxide; and said catalyst comprises a mixture obtained by heating metallic sodium at a temperature above the melting point of metallic sodium together with said mixture of alkaline earth metal oxide and a potassium compound. ### Claim 12 (depends on 10) The process according to claim 10, wherein said alkaline earth metal oxide is magnesium oxide or calcium oxide. ### Claim 13 (depends on 11) The process according to claim 11, wherein said alkaline earth metal oxide is magnesium oxide or calcium oxide. ### Claim 14 (depends on 13) The process according to claim 13, wherein said potassium compound is potassium hydroxide. ### Claim 15 (depends on 13) The process according to claim 13, wherein said potassium compound is potassium carbonate. ### Claim 16 (depends on 13) The process according to claim 13, wherein said potassium compound is potassium hydrogen carbonate. ### Claim 17 (depends on 13) The process according to claim 13, wherein said aromatic hydrocarbon compound is o-xylene, m-xylene, p-xylene, or 2-ethylbenzene and said conjugated diene is 1,3-butadiene. ### Claim 18 (depends on 17) The process according to claim 17, wherein said aromatic hydrocarbon compound is o-xylene. ### Claim 19 (depends on 17) The process according to claim 17, wherein said aromatic hydrocarbon compound is m-xylene. ### Claim 20 (depends on 17) The process according to claim 17, wherein said aromatic hydrocarbon compound is p-xylene. ### Claim 21 (depends on 17) The process according to claim 17, wherein said aromatic hydrocarbon compound is 2-ethylbenzene.