# US 9,435,688 B2 · Method for quantitation of acid sites in acidic catalysts using silane and borane compounds > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,435,688 B2 - Document ID: US9435688B2 - Status: Granted - Kind: B2 - Application number: 14/703,249 - Filed: 2015-05-04 - Published: 2015-11-05 - Granted: 2016-09-06 - Earliest claimed: 2014-05-05 - Assignees: Uop LLC - Applicants: Uop LLC - Inventors: Susie C. Martins; Erin M. Broderick - Web page: https://patentgrep.com/patent/US9435688B2 ## CPC - G01J 3/28: Investigating the spectrum (using colour filters G01J3/51) - B01J 31/00: Catalysts comprising hydrides, coordination complexes or organic compounds (catalyst compositions used only in polymerisation reactions C08 {; catalytic antibodies C12N9/0002}) - B01J 31/40: Regeneration or reactivation - G01N 23/223: by irradiating the sample with X-rays or gamma-rays and by measuring X-ray fluorescence - G01N 30/02: Column chromatography - G01N 31/10: using catalysis - G01R 33/46: NMR spectroscopy - B01J 31/0298: {the ionic liquids being characterised by the counter-anions} - B01J 2231/32: Addition reactions to C=C or C-C triple bonds - G01N 24/08: by using nuclear magnetic resonance (G01N24/12 takes precedence) - G01N 30/88: Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 - G01N 2030/025: {Gas chromatography} - G01N 2030/027: {Liquid chromatography} - G01J: MEASUREMENT OF INTENSITY, VELOCITY, SPECTRAL CONTENT, POLARISATION, PHASE OR PULSE CHARACTERISTICS OF INFRARED, VISIBLE OR ULTRAVIOLET LIGHT; COLORIMETRY; RADIATION PYROMETRY (light sources F21, H01J, H01K, H05B; investigating properties of materials by optical means G01N) - B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS - G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q) - G01R: MEASURING ELECTRIC VARIABLES; MEASURING MAGNETIC VARIABLES (indicating correct tuning of resonant circuits H03J3/12) ## Abstract A method of quantifying an amount of Brønsted acid sites in an aluminum chloride-containing catalyst is described. The method involves adding a known amount of at least one silane or borane compound to the aluminum chloride-containing catalyst being analyzed. The Brønsted acid sites in the aluminum chloride-containing catalyst react with the silane or borane compound to form a silyl boryl compound, resulting in a catalyst phase and a hydrocarbon phase which contains the silyl or boryl compound. The amount of silyl or boryl compound in the hydrocarbon phase is measured. From the measured amount of silyl or boryl compound formed, the amount of Brønsted acid sites can be determined. ## Claims ### Claim 1 A method of quantifying an amount of Brønsted acid sites in an aluminum chloride-containing catalyst comprising: contacting a known amount of at least one silane or borane compound with the aluminum chloride-containing catalyst, the Brønsted acid sites in the aluminum chloride-containing catalyst reacting with the at least one silane or borane compound resulting in an catalyst phase and a hydrocarbon phase comprising at least one silyl or boryl compound; measuring an amount of the at least one silyl or boryl compound in the hydrocarbon phase; determining the amount of Brønsted acid sites from the measured amount of the at least one silyl or boryl compound. ### Claim 2 (depends on 1) The method of claim 1 wherein measuring the amount of the at least one silyl or boryl compound comprises measuring the amount of the at least one silyl or boryl compound using gas chromatography, infrared spectroscopy, nuclear magnetic resonance spectroscopy, x-ray fluorescence, liquid chromatography, ion chromatography, or combinations thereof. ### Claim 3 (depends on 1) The method of claim 1 further comprising separating the catalyst phase from the hydrocarbon phase before measuring the amount of the at least one silyl or boryl compound. ### Claim 4 (depends on 3) The method of claim 3 further comprising adding an acid or acid precursor to the catalyst phase to regenerate the Brønsted acid sites in the aluminum chloride-containing catalyst. ### Claim 5 (depends on 3) The method of claim 3 further comprising chemically reducing the at least one silyl or boryl compound with a compound containing hydrogen to regenerate the at least one silane or borane compound. ### Claim 6 (depends on 5) The method of claim 5 wherein the compound containing hydrogen comprises a metal hydride. ### Claim 7 (depends on 6) The method of claim 6 wherein the metal hydride comprises LiH, NaH, CaH2, NaAlH4, LiAlH4, KH, NaBH4, diisobutylaluminum hydride, or combinations thereof. ### Claim 8 (depends on 1) The method of claim 1 wherein the at least one silane compound has the formula: R3SiH, R2SiH2, RSiH3, or SiH4, where each R is independently selected from hydrocarbons or halides. ### Claim 9 (depends on 1) The method of claim 1 wherein the at least one borane compound comprises a compound having a formula R2BH, where each R is independently selected from hydrocarbons or halides, or B2H6, or combinations thereof. ### Claim 10 (depends on 9) The method of claim 9 wherein the hydrocarbon solvent comprises a paraffin having up to 10 carbon atoms, an aromatic, or the at least one silane or borane compound. ### Claim 11 (depends on 1) The method of claim 1 wherein contacting the known amount of the at least one silane or borane compound with the aluminum chloride-containing catalyst comprises contacting the known amount of the at least one silane or borane compound with the aluminum chloride-containing catalyst in a hydrocarbon solvent. ### Claim 12 (depends on 1) The method of claim 1 wherein the aluminum chloride-containing catalyst further comprises a conjunct polymer, the conjunct polymer reacting with the at least one silane or borane compound, and further comprising: determining an amount of conjunct polymer from the measured amount of the at least one silyl or boryl compound. ### Claim 13 (depends on 12) The method of claim 12 wherein the conjunct polymer reacting with the at least one silane or borane compound releases conjunct polymer and additional silyl or boryl compound, the hydrocarbon phase further comprising the conjunct polymer and the additional silyl or boryl compound, and further comprising separating the conjunct polymer from the hydrocarbon phase. ### Claim 14 (depends on 1) The method of claim 1 wherein contacting the known amount of the at least one silane or borane compound with the aluminum chloride-containing catalyst further comprises mixing the known amount of the at least one silane or borane compound with the aluminum chloride-containing catalyst. ### Claim 15 A method of quantifying an amount of Brønsted acid sites in an aluminum chloride-containing catalyst comprising: contacting a known amount of at least one silane or borane compound with the aluminum chloride-containing catalyst, the Brønsted acid sites in the aluminum chloride-containing catalyst reacting with the at least one silane or borane compound resulting in an catalyst phase and a hydrocarbon phase comprising at least one silyl or boryl compound; separating the catalyst phase from the hydrocarbon phase; measuring an amount of the at least one silyl or boryl compound in the hydrocarbon phase using gas chromatography, infrared spectroscopy, nuclear magnetic resonance spectroscopy, x-ray fluorescence, liquid chromatography, ion chromatography, or combinations thereof; determining the amount of Brønsted acid sites from the measured amount of the at least one silyl or boryl compound. ### Claim 16 (depends on 15) The method of claim 15 further comprising chemically reducing the at least one silyl or boryl compound with a compound containing hydrogen to regenerate the at least one silane or borane compound. ### Claim 17 (depends on 16) The method of claim 16 wherein the compound containing hydrogen comprises a metal hydride. ### Claim 18 (depends on 15) The method of claim 15 wherein the at least one silane compound has the formula: R3SiH, R2SiH2, RSiH3, or SiH4, where each R is independently selected from hydrocarbons or halides. ### Claim 19 (depends on 15) The method of claim 15 wherein the at least one borane compound comprises a compound having a formula R2BH, where each R is independently selected from hydrocarbons or halides, or B2H6, or combinations thereof. ### Claim 20 (depends on 15) The method of claim 15 wherein contacting the known amount of the at least one silane or borane compound with the aluminum chloride-containing catalyst comprises contacting the known amount of the at least one silane or borane compound with the aluminum chloride-containing catalyst in a hydrocarbon solvent.