# US 8,540,871 B2 · Denitrification of a hydrocarbon feed > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,540,871 B2 - Document ID: US8540871B2 - Status: Granted - Kind: B2 - Application number: 12/847,107 - Filed: 2010-07-30 - Published: 2012-02-02 - Granted: 2013-09-24 - Earliest claimed: 2010-07-30 - Assignees: Chevron U.S.A. Inc. - Applicants: Bi-Zeng Zhan; Akshay Verma; Zunqing He; Zhen Zhou; Marcus Dutra e Mello; Sheila Yeh - Inventors: Bi-Zeng Zhan; Akshay Verma; Zunqing He; Zhen Zhou; Marcus Dutra e Mello; Sheila Yeh - Web page: https://patentgrep.com/patent/US8540871B2 ## CPC - C10G 25/003: {Specific sorbent material, not covered by C10G25/02 or C10G25/03} - C10G 67/06: including a sorption process as the refining step in the absence of hydrogen - C10G 2300/1037: Hydrocarbon fractions - C10G 2300/107: Atmospheric residues having a boiling point of at least about 538 °C - C10G 2300/1074: Vacuum distillates - C10G 2300/1077: Vacuum residues - C10G 2300/202: Heteroatoms content, i.e. S, N, O, P - C10G 2400/10: Lubricating oil - 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 denitrification method is disclosed for removing nitrogen compounds from a hydrocarbon feed in which the feed is contacted with an adsorbent including an organic heterocyclic salt deposited on a porous support. Additionally, a method for hydrotreating a hydrocarbon feed which includes a hydroprocessing step is disclosed, wherein prior to hydroprocessing, the feed is contacted with an adsorbent including an organic heterocyclic salt deposited on a support. Additionally, a method for producing a lube oil which includes isomerization dewaxing of a base oil fraction is disclosed, wherein prior to the isomerization dewaxing step, the base oil fraction is contacted with an adsorbent including an organic heterocyclic salt deposited on a support. ## Claims ### Claim 1 A method for removing nitrogen compounds from a hydrocarbon feed, comprising: contacting the feed with an adsorbent comprising at least one organic heterocyclic salt deposited on a porous support selected from the group consisting of molecular sieve, silica, alumina, silica-alumina, carbon, clay and mixtures thereof, thereby resulting in a product containing a reduced amount of nitrogen as compared with the feed and the product has a nitrogen concentration of less than 10 ppm; wherein the feed is selected from any of hydrotreated products, hydrocracked products, coker products, straight run feed, distillate products, FCC bottoms, atmospheric and vacuum bottoms, vacuum gas oils and unconverted oils, the feed has a nitrogen concentration of 3-50 ppm, wherein the adsorbent is stationary in a fixed bed adsorber in a continuous process and no mechanical stirring is applied to the process. ### Claim 2 (depends on 1) The method of claim 1, wherein no external heat is applied to the process. ### Claim 3 (depends on 1) The method of claim 1, wherein the feed contacts the adsorbent at a temperature in the range of 0° C. to 200° C. ### Claim 4 (depends on 1) The method of claim 1, wherein the product contains less than 1 ppm nitrogen. ### Claim 5 (depends on 1) The method of claim 1, wherein the porous support comprises carbon which has been oxidized having a BET surface area of between 200 m2/g and 3000 m2/g. ### Claim 6 (depends on 1) The method of claim 1, wherein the porous support comprises an inorganic material selected from the group consisting of molecular sieve, silica, alumina, silica-alumina, clay and mixtures thereof having a BET surface area of between 50 m2/g and 1500 m2/g. ### Claim 7 (depends on 1) The method of claim 1, wherein the porous support comprises pores having an average pore diameter of between 0.5 nm and 20 nm and a pore volume of between 0.1 and 3 cm3/g. ### Claim 8 (depends on 1) The method of claim 1, wherein the organic heterocyclic salt has a general formula of: wherein: A is a nitrogen cation containing heterocyclic group selected from the group consisting of imidazolium, pyrazolium, 1,2,3-triazolium, 1,2,4-triazolium, pyridinium, pyrazinium, pyrimidinium, pyridazinium, 1,2,3-triazinium, 1,2,4-triazinium, 1,3,5-triazoinium, quinolinium, and isoquinolinium; R1, R2, R3, and R4 are substituent groups attached to the carbon or nitrogen of the heterocyclic group A, independently selected from the group consisting of hydroxyl, amino, acyl, carboxyl, linear unsubstituted C1-C12 alkyl groups, branched unsubstituted C1-C12 alkyl groups, linear C1-C12 alkyl groups substituted with oxy, amino, acyl, carboxyl, alkenyl, alkynyl, trialkoxysilyl, and alkyldialkoxysilyl groups, branched substituted C1-C12 alkyl groups substituted with oxy, amino, acyl, carboxyl, alkenyl, alkynyl, trialkoxysilyl, and alkyldialkoxysilyl groups; and X is an inorganic or organic anion selected from the group consisting of fluoride, chloride, bromide, iodide, aluminum tetrachloride, heptachloroaluminate, sulfite, sulfate, phosphate, phosphoric acid, mono hydrogen phosphate, bicarbonate, carbonate, hydroxide, nitrate, trifluoromethanesulfonate, sulfonate, phosphonate, carboxylate groups of C2-C18 organic acids, and chloride or fluoride substituted carboxylate groups. ### Claim 9 (depends on 1) The method of claim 1, wherein the organic heterocyclic salt comprises an imidazolium ion. ### Claim 10 (depends on 9) The method of claim 9, wherein the adsorbent has a denitrification capacity of at least 0.17 mole of nitrogen adsorbed per mole of imidazolium ion. ### Claim 11 (depends on 1) The method of claim 1, wherein the adsorber has a bottom end and top end and the feed is introduced to the adsorber at the bottom end and the product is recovered at the top end. ### Claim 12 (depends on 1) The method of claim 1, further comprising: ceasing the contacting step; and regenerating the adsorbent by contacting the adsorbent with an aromatics-containing regenerant. ### Claim 13 (depends on 12) The method of claim 12, wherein the adsorbent is regenerated completely in the regenerating step. ### Claim 14 (depends on 1) The method of claim 1, followed by at least one hydroprocessing step selected from hydrotreating, hydrocracking, hydroisomerization and hydrodemetallization. ### Claim 15 A method for producing a lube oil comprising contacting a hydrocarbon feed with a hydrocracking catalyst, separating the hydrocracked feed into at least one light fraction and a base oil fraction, and contacting the base oil fraction with a bed of isomerization dewaxing catalyst to produce a stream, wherein prior to contacting the hydrocracked feed with the isomerization dewaxing catalyst, the base oil fraction is contacted with an adsorbent comprising an organic heterocyclic salt deposited on a support.