# US 5,349,116 A · Alkane alkylation and catalyst therefor > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,349,116 A - Document ID: US5349116A - Status: Granted - Kind: A - Application number: 08/082,586 - Filed: 1993-06-25 - Granted: 1994-09-20 - Earliest claimed: 1993-06-25 - Assignees: Phillips Petroleum Company - Inventors: Lyle R. Kallenbach; Marvin M. Johnson - Web page: https://patentgrep.com/patent/US5349116A ## CPC - B01J 31/0227: {being perfluorinated, i.e. comprising at least one perfluorinated moiety as substructure in case of polyfunctional compounds} - B01J 21/02: Boron or aluminium; Oxides or hydroxides thereof - C07C 2/62: with acids - B01J 2231/323: Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation - C07C 2521/02: Boron or aluminium; Oxides or hydroxides thereof - C07C 2521/04: Alumina - C07C 2531/025: Sulfonic acids - B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract A composition of matter comprises trifluorometbanesulfonic acid and a solid inorganic material which contains aluminum borate and aluminum oxide, This composition is used as a catalyst for alkylating at least one C.sub.2 -C.sub.10 alkane (preferably isobutane and/or an isooctane) with at least one C.sub.2 -C.sub.10 alkene (preferably pentene-1 and/or hexene-1). ## Claims ### Claim 1 A process for alkylating alkanes which comprises contacting at least one feed alkane containing about 4-8 carbon atoms per molecule with at least one feed alkene containing about 4-6 carbon atoms per molecule in the presence of a catalyst composition which consists essentially of (a) trifluoromethanesulfonic acid and (b) a solid inorganic material consisting essentially of aluminum borate and aluminum oxide, at effective alkylation conditions comprising a reaction temperature of up to about 100.degree. C., so as to obtain a product in which the weight percentage of product alkanes boiling in a temperature range of about 310.degree. F. to about 500.degree. F. at atmospheric pressure conditions exceeds the weight percentage of product hydrocarbons boiling at a temperature above 500.degree. F. at atmospheric pressure conditions. ### Claim 2 (depends on 1) A process in accordance with claim 1, wherein the weight ratio of trifluorometbanesulfonic acid to said solid inorganic material in said catalyst composition is in the range of about 0.02:1 to about 0.4:1. ### Claim 3 (depends on 2) A process in accordance with claim 2, wherein said solid inorganic material contains about 5-15 weight-% aluminum borate. ### Claim 4 (depends on 3) A process in accordance with claim 3, wherein said solid inorganic material is an alumina-supported coprecipitate of aluminum borate and aluminum oxide. ### Claim 5 (depends on 4) A process in accordance with claim 4 wherein said coprecipitate has a boron:aluminum atomic ratio of about 0.4:1 to about 4: 1. ### Claim 6 (depends on 5) A process in accordance with claim 5, wherein said solid inorganic material has been prepared by a method comprising the steps of forming an aqueous solution of boric acid and at least one water-soluble aluminum salt wherein the molar ratio of boric acid to said at least one aluminum salt is in the range of about 0.03:1 to about 15:1, mixing said aqueous solution with alumina particles so as to form an aqueous slurry, adding an aqueous solution of ammonia to said aqueous slurry so as to attain a pH of about 7-8 of the aqueous phase of said aqueous slurry and to form a solid combination of a coprecipitate of (i) aluminum borate and aluminum oxide and (ii) alumina support particles wherein said solid combination is dispersed in said aqueous phase, separating said solid combination from said aqueous phase washing said solid combination with water, drying the obtained washed solid combination, and calcining the dried solid combination at a temperature of about 450.degree.-600.degree. C. ### Claim 7 (depends on 1) A process in accordance with claim 1, wherein said feed alkane is selected from the group consisting of isobutane and 2,2,4- trimethylpentane, and said at least one feed alkene is selected from the group consisting of pentene-1 and hexene-1. ### Claim 8 (depends on 1) A process in accordance with claim 1 wherein said effective alkylation conditions comprise a molar ratio of said at least one feed alkane to said at least one feed alkene in the range of about 6:1 to about 12:1 and a reaction temperature of about -20.degree. C. to about 100.degree. C. ### Claim 9 (depends on 8) A process in accordance with claim 8, wherein said effective alkylation conditions further comprise a liquid hourly space velocity of the feed comprising said at least one feed alkane and said at least one feed alkene of about 0.5-3 cm.sup.3 feed per cm.sup.3 catalyst composition per hour, a reaction temperature of about 0.degree.-30.degree. C., and a reaction pressure of about 2-8 atmospheres. ### Claim 10 (depends on 6) A process in accordance with claim 6 wherein said drying is carried out at a temperature of about 100.degree.-150.degree. C. for about 0.1-20 hours, and said calcining is carried out at a temperature of about 480-570 for about 2-6 hours. ### Claim 11 (depends on 1) A process in accordance with claim 1, comprising the additional step of separating said product alkanes boiling in a temperature range of about 310.degree. F. to about 500.degree. F. from at least one unconverted feed alkane and at least one unconverted feed alkene. ### Claim 12 (depends on 11) A process in accordance with claim 11, further comprising the additional step of separating said product alkanes boiling in a temperature range of about 310.degree. F. to about 500.degree. F. from said product hydrocarbons boiling at a temperature above 500.degree. F. ### Claim 13 (depends on 11) A process in accordance with claim 11, wherein said separating is carried out by fractional distillation. ### Claim 14 (depends on 12) A process in accordance with claim 12, wherein said separating is carried out by fractional distillation. ### Claim 15 A process for producing alkanes boiling in a temperature range of about 310.degree. F. to about 500.degree. F. at atmospheric pressure conditions which comprises contacting at least one feed alkane containing about 4-8 carbon atoms per molecule with at least one feed alkene containing about 4-6 carbon atoms per molecule in the presence of a catalyst composition which consists essentially of (a) trifluoromethanesulfonic acid and (b) a solid inorganic material consisting essentially of about 5-15 weight-% aluminum borate and aluminum oxide as the remainder, at effective alkylation conditions comprising a reaction temperature of about -20.degree. C. to about 100.degree. C., so as to obtain at least one product alkane boiling at a temperature of about 310.degree.-500.degree. F. at atmospheric pressure conditions. ### Claim 16 (depends on 15) A process in accordance with claim 15, comprising the additional step of separating said at least one product alkane boiling at a temperature of about 310.degree.-500.degree. F. from unconverted feed alkanes. ### Claim 17 (depends on 16) A process in accordance with claim 16, further comprising the additional step of separating said at least one product alkane boiling at a temperature of about 310.degree.-500.degree. F. from by-product hydrocarbons boiling above a temperature of 500.degree. F. at atmospheric pressure conditions. ### Claim 18 (depends on 17) A process in accordance with claim 17, wherein both separating steps are carried out by fractional distillation. ### Claim 19 (depends on 15) A process in accordance with claim 15, wherein said effective alkylation conditions comprise a reaction temperature of about 0.degree. C. to about 30.degree. C. ### Claim 20 (depends on 15) A process in accordance with claim 15, wherein said solid inorganic material contains 7-13 weight-% aluminum borate and about 87-93 weight-% aluminum oxide.