# US 11,111,444 B2 · Process for reducing nitrogen content of hydrocarbon feed

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- Number: US 11,111,444 B2
- Document ID: US11111444B2
- Status: Granted
- Kind: B2
- Application number: 16/760,251
- Filed: 2018-10-30
- Published: 2020-11-05
- Granted: 2021-09-07
- Earliest claimed: 2017-10-31
- Assignees: Reliance Industries Limited
- Applicants: Reliance Industries Limited
- Inventors: Rajesh Vishnudev Sharma; Sanjeev Shriniwas Katti
- Web page: https://patentgrep.com/patent/US11111444B2

## CPC

- C10G 25/00: Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents
- C10G 25/003: {Specific sorbent material, not covered by C10G25/02 or C10G25/03}
- B01J 20/08: comprising aluminium oxide or hydroxide; comprising bauxite
- C10G 2300/1055: Diesel having a boiling range of about 230 - 330 °C
- C10G 2300/202: Heteroatoms content, i.e. S, N, O, P
- 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
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

The present disclosure relates to a process for reducing the nitrogen content in a hydrocarbon feed comprising nitrogen compound. The process comprises mixing the hydrocarbon feed containing nitrogen compounds with at least one adsorbent and stirring at a temperature in the range of 25° C. to 80° C. for a pre-determined time period. The adsorbents of the present disclosure are efficient for the removal of refractory organic nitrogen compounds in the range of 0.01 ppm to 10 ppm. The process of the present disclosure is simple and use inexpensive adsorbent and requires mild operation conditions.

## Claims

### Claim 1

A process for reducing the nitrogen content in a hydrocarbon feed comprising nitrogen compounds, the process comprising the following steps:
a. mixing the hydrocarbon feed with at least one adsorbent to obtain a mixture;
b. stirring the mixture at a temperature in the range of 25° C. to 80° C. for a pre-determined time period to obtain a resultant mixture;
c. allowing the resultant mixture to settle to separate an upper phase comprising treated hydrocarbon having reduced nitrogen content and a lower phase comprising a complex of nitrogen compounds and the adsorbent; and
d. separating the upper phase from the lower phase to obtain treated hydrocarbon having reduced nitrogen content;
wherein the adsorbent is a mixture of a Lewis acid and a Lewis base;
wherein the Lewis acid is at least one selected from the group consisting of AlCl3, FeCl3, ZnCl2, GaCl3, InCl3, TiCl4, SnCl4, BiCl3 and ZrCl4; and the Lewis base is at least one selected from the group consisting of Al(OH)3, Fe(OH)3 and Zn(OH)2.

### Claim 2 (depends on 1)

The process as claimed in claim 1, wherein the nitrogen compounds comprise refractory organic nitrogen compounds.

### Claim 3 (depends on 1)

The process as claimed in claim 1, the nitrogen compounds are selected from the group consisting of pyrrole, pyrrolidine, quinolone, indole, acridine and derivatives thereof.

### Claim 4 (depends on 1)

The process as claimed in claim 1, wherein the hydrocarbon feed is diesel.

### Claim 5 (depends on 1)

The process as claimed in claim 1, wherein the mass of the adsorbent used is in the range of 0.25 mass % to 1.0 mass % of the mass of the hydrocarbon feed.

### Claim 6 (depends on 1)

The process as claimed in claim 1, wherein the adsorbent is a mixture of AlCl3, and Al(OH)3.

### Claim 7 (depends on 1)

The process as claimed in claim 1, wherein the mole ratio of the Lewis acid to the Lewis base is in the range of 1:1 to 5:1.

### Claim 8 (depends on 1)

The process as claimed in claim 1, wherein the stirring in step (ii) is carried out at atmospheric pressure and at a stirring speed in the range of 100 rpm to 1000 rpm.

### Claim 9 (depends on 1)

The process as claimed in claim 1, wherein the pre-determined time period is in the range of 15 minutes to 120 minutes.

### Claim 10 (depends on 1)

The process as claimed in claim 1, wherein the treated hydrocarbon has nitrogen compounds in the range of 0.01 ppm to 10 ppm.

### Claim 11 (depends on 1)

The process as claimed in claim 1, wherein the treated hydrocarbon has sulfur compounds in the range of 0.1 ppm to 10 ppm.