# US 11,305,259 B2 · Synthesis of 4-phenyl-1,2,3-triazole functionalized SBA-15 and its application thereof

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- Number: US 11,305,259 B2
- Document ID: US11305259B2
- Status: Granted
- Kind: B2
- Application number: 16/296,480
- Filed: 2019-03-08
- Published: 2020-09-10
- Granted: 2022-04-19
- Earliest claimed: 2019-03-08
- Assignees: King Fahd University of Petroleum and Minerals
- Applicants: King Fahd University of Petroleum and Minerals
- Inventors: Khalid Alhooshani; Abdulkadir Tanimu
- Web page: https://patentgrep.com/patent/US11305259B2

## CPC

- B01J 20/3255: {comprising a cyclic structure containing at least one of the heteroatoms nitrogen, oxygen or sulfur, e.g. heterocyclic or heteroaromatic structures}
- B01J 20/103: {comprising silica}
- B01J 20/28061: {being in the range 100-500 m2/g}
- B01J 20/28071: {being less than 0.5 ml/g}
- B01J 20/28073: {being in the range 0.5-1.0 ml/g}
- B01J 20/28083: {being in the range 2-50 nm, i.e. mesopores}
- B01J 20/3236: {containing metal, other than zeolites, e.g. oxides, hydroxides, sulphides or salts}
- B01J 2220/46: Materials comprising a mixture of inorganic and organic materials (materials coated or impregnated on a carrier B01J20/32)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

A functionalized silica sorbent is described. The sorbent comprises mesoporous silica nanoparticles having a surface functionalized with a conjugated system comprising an azole and a phenyl. The surface may be functionalized by a Cu-catalyzed click reaction. The nanoparticles have an average particle size of 10-80 nm, and may be used to adsorb phenolic contaminants from aqueous solutions.

## Claims

### Claim 1

A functionalized silica sorbent comprising:
porous silica nanoparticles having a surface functionalized with a conjugated system attached by an alkyl chain of length C8-C16,
wherein the conjugated system comprises an azole group and a phenyl group, and
wherein the porous silica nanoparticles have an average particle size of 10-80 nm.

### Claim 2 (depends on 1)

The functionalized silica sorbent of claim 1, wherein the porous silica nanoparticles are clustered in agglomerates having an average diameter of 1-4 μm.

### Claim 3 (depends on 1)

The functionalized silica sorbent of claim 1, wherein the porous silica nanoparticles have an average pore size in a range of 4-9 nm.

### Claim 4 (depends on 1)

The functionalized silica sorbent of claim 1, wherein the porous silica nanoparticles have a BET surface area of 200-380 m2/g.

### Claim 5 (depends on 1)

The functionalized silica sorbent of claim 1, wherein the porous silica nanoparticles have a total pore volume in a range of 0.380-0.700 cm3/g.

### Claim 6 (depends on 1)

The functionalized silica sorbent of claim 1, wherein the conjugated system consists of a triazole group and a phenyl group.

### Claim 7 (depends on 6)

The functionalized silica sorbent of claim 6, wherein the conjugated system is 4-phenyl-1,2,3-triazole.

### Claim 8 (depends on 1)

The functionalized silica sorbent of claim 1, wherein the alkyl chain has a length of C10-C12.

### Claim 9 (depends on 1)

The functionalized silica sorbent of claim 1, which has 3-12 wt % N relative to a total weight of the functionalized silica sorbent.

### Claim 10 (depends on 1)

The functionalized silica sorbent of claim 1, which has 50-58 wt % Si relative to a total weight of the functionalized silica sorbent.

### Claim 11 (depends on 1)

A method for producing the functionalized silica sorbent of claim 1, comprising:
mixing a silicon alkoxide, an azidoalkyltrialkoxysilane, and a structure directing agent with an acidic solution to produce a reaction mixture;
heating the reaction mixture in an autoclave at 80-120° C. for 18-30 h to produce an azide-functionalized silica; and
mixing the azide-functionalized silica with an aqueous solution, a copper salt, and an arylalkyne for 4-24 h to produce the functionalized silica sorbent.

### Claim 12 (depends on 11)

The method of claim 11, wherein the azidoalkyltrialkoxysilane is azidoundecyltrimethoxysilane.

### Claim 13 (depends on 11)

The method of claim 11, wherein the silicon alkoxide is tetraethyl orthosilicate.

### Claim 14 (depends on 11)

The method of claim 11, wherein the structure directing agent is a nonionic block copolymer.

### Claim 15 (depends on 11)

The method of claim 11, wherein the copper salt is CuSO4.

### Claim 16 (depends on 1)

A method of adsorbing a contaminant from an aqueous solution, the method comprising:
mixing the functionalized silica sorbent of claim 1 with the aqueous solution comprising the contaminant at a concentration of 1-600 ng/mL,
wherein a concentration of the functionalized silica sorbent after mixing is 1-100 mg/mL, and
wherein at least 85 wt % of the contaminant relative to a total weight of the contaminant is adsorbed by the functionalized silica sorbent in 10-25 min.

### Claim 17 (depends on 16)

The method of claim 16, wherein the contaminant is at least one selected from the group consisting of a dichlorophenol, a trichlorophenol, 2,6-di-tert-butyl-4-methylphenol, 4-tert-octylphenol, and a benzyl-chlorophenol.

### Claim 18 (depends on 16)

The method of claim 16, wherein the functionalized silica sorbent is confined within a porous membrane bag.

### Claim 19 (depends on 16)

The method of claim 16, wherein the aqueous solution further comprises an inorganic salt at a concentration of 0.01-0.2 g/mL.

### Claim 20 (depends on 16)

The method of claim 16, further comprising desorbing the contaminant by sonicating the functionalized silica sorbent with the adsorbed contaminant in an organic solvent for 15-30 min.