# US 10,119,079 B2 · Composition for removal of sulfur-containing compounds

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- Number: US 10,119,079 B2
- Document ID: US10119079B2
- Status: Granted
- Kind: B2
- Application number: 15/126,191
- Filed: 2015-03-11
- Published: 2017-03-23
- Granted: 2018-11-06
- Earliest claimed: 2014-03-17
- Assignees: Kuraray Co., Ltd.
- Applicants: Kuraray Co., Ltd.
- Inventors: Junichi Fuji; Ryoko Miyazaki; Takahiro Suzuki
- Web page: https://patentgrep.com/patent/US10119079B2

## CPC

- C10G 29/24: Aldehydes or ketones
- C10G 29/20: Organic compounds not containing metal atoms
- C10L 3/103: {Sulfur containing contaminants}
- C23F 11/122: {Alcohols; Aldehydes; Ketones}
- 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
- C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C23F: NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE (working metal by laser beams B23K26/00; desurfacing by applying flames B23K7/00; working of metal by electro-erosion B23H; producing decorative effects by removing surface material, e.g. by engraving, by etching, B44C1/22; electrolytic etching or polishing C25F); INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25

## Abstract

Disclosed is a composition capable of removing safely and efficiently a sulfur-containing compound contained in a hydrocarbon, particularly hydrogen sulfide, an —SH group-containing compound, or a mixture thereof. Provided is a composition for removal of a sulfur-containing compound in a hydrocarbon, the sulfur-containing compound being hydrogen sulfide, an —SH group-containing compound or a mixture thereof: the composition containing a dialdehyde having 6 to 16 carbon atoms as an active ingredient.

## Claims

### Claim 1

A method for removing a sulfur-containing compound in a hydrocarbon, the method comprising contacting the hydrocarbon with a composition consisting of 1) 1,9-nonanedial, 2-methyl-1,8-octanedial, or both; 2) optionally, a solvent selected from water, toluene, xylene, heavy aromatic naphtha, petroleum distillate, or a monoalcohol or diol having 1 to 10 carbon atoms; and 3) optionally, a nitrogen-containing compound selected from α-amino ether compounds, alkoxy-hexahydrotriazine compounds, alkyl-hexahydrotriazine compounds, hydroxyalkyl-hexahydrotriazine compounds, monoamine compounds, diamine compounds, reaction products between an alkylenepolyamine and formaldehyde, quaternary ammonium salt compounds, imine compounds, imidazoline compounds, hydroxyaminoalkyl ether compounds, morpholine compounds, pyrrolidone compounds, piperidone compounds, alkylpyridine compounds, 1H-hexahydroazepine, polyvalent metal chelate compounds of an aminocarboxylic acid, polyethyleneimine, polyallylamine, polyvinylamine, amino carbinol compounds, aminal compounds, and bisoxazolidine compounds, wherein the sulfur-containing compound is hydrogen sulfide, an —SH group-containing compound, or a mixture thereof.

### Claim 2 (depends on 1)

The method according to claim 1, comprising further contacting the hydrocarbon with a nitrogen-containing compound.

### Claim 3 (depends on 1)

The method according to claim 1, wherein the hydrocarbon is one or more selected from the group consisting of natural gas, liquefied natural gas, sour gas, crude oil, naphtha, heavy aromatic naphtha, gasoline, kerosene, diesel oil, light oil, heavy oil, FCC slurry, asphalt, and an oil field concentrate.

### Claim 4 (depends on 1)

The method according to claim 1, wherein an amount of the composition is from 1 to 10,000 ppm relative to a mass of the hydrocarbon.

### Claim 5 (depends on 1)

The method according to claim 1, wherein the composition and the hydrocarbon are brought into contact with each other at a temperature of from 20° C. to 200° C.

### Claim 6

A method for removing a sulfur-containing compound in a hydrocarbon, the method comprising contacting the hydrocarbon with a composition consisting of 1) 3-methylglutaraldehyde; 2) optionally, a solvent selected from water, toluene, xylene, heavy aromatic naphtha, petroleum distillate, or a monoalcohol or diol having 1 to 10 carbon atoms; and 3) optionally, a nitrogen-containing compound selected from α-amino ether compounds, alkoxy-hexahydrotriazine compounds, alkyl-hexahydrotriazine compounds, hydroxyalkyl-hexahydrotriazine compounds, monoamine compounds, diamine compounds, reaction products between an alkylenepolyamine and formaldehyde, and quaternary ammonium salt compounds, imine compounds, imidazoline compounds, hydroxyaminoalkyl ether compounds, morpholine compounds, pyrrolidone compounds, piperidone compounds, alkylpyridine compounds, 1H-hexahydroazepine, polyvalent metal chelate compounds of an aminocarboxylic acid, polyethyleneimine, polyallylamine, polyvinylamine, amino carbinol compounds, aminal compounds, and bisoxazolidine compounds, wherein the sulfur-containing compound is hydrogen sulfide, an SH group-containing compound, or a mixture thereof.

### Claim 7 (depends on 6)

The method according to claim 6, comprising further contacting the hydrocarbon with a nitrogen-containing compound.

### Claim 8 (depends on 6)

The method according to claim 6, wherein the hydrocarbon is one or more selected from the group consisting of natural gas, liquefied natural gas, sour gas, crude oil, naphtha, heavy aromatic naphtha, gasoline, kerosene, diesel oil, light oil, heavy oil, FCC slurry, asphalt, and an oil field concentrate.

### Claim 9 (depends on 6)

The method according to any of claim 6, wherein an amount of the composition is from 1 to 10,000 ppm relative to a mass of the hydrocarbon.

### Claim 10 (depends on 6)

The method according to any of claim 6, wherein the composition and the hydrocarbon are brought into contact with each other at a temperature of from 20° C. to 200° C.