# US 12,422,430 B2 · Fluid analyses and sensor constructs employing hexasubstituted benzenes

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 12,422,430 B2
- Document ID: US12422430B2
- Status: Granted
- Kind: B2
- Application number: 17/637,972
- Filed: 2020-09-10
- Published: 2022-09-08
- Granted: 2025-09-23
- Earliest claimed: 2019-09-10
- Assignees: Countertrace LLC
- Applicants: Countertrace, LLC
- Inventors: Robert E. Hanes, Jr.; Richard L. Pettys; David M. Headley; Paul T. Hoopingarner
- Web page: https://patentgrep.com/patent/US12422430B2

## CPC

- G01N 33/54353: {with ligand attached to the carrier via a chemical coupling agent (coatings G01N33/54393)}
- G01N 33/5438: {Electrodes}
- G01N 33/18: Water
- G01N 33/2835: {Specific substances contained in the oils or fuels}
- G01N 33/48707: {by electrical means (G01N33/49, G01N33/493 take precedence)}
- E21B 47/00: Survey of boreholes or wells (monitoring pressure or flow of drilling fluid E21B21/08)
- G01N 31/22: using chemical indicators (G01N31/02 takes precedence)
- 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)
- E21B: EARTH OR ROCK DRILLING; OBTAINING OIL, GAS, WATER, SOLUBLE OR MELTABLE MATERIALS OR A SLURRY OF MINERALS FROM WELLS

## Abstract

Phenyl rings provide a robust scaffold for molecular design, given the limited number of ring carbon atoms and the fixed geometry in between. Alternating groups in hexasubstituted benzenes may be directed toward opposite faces of the phenyl ring, such that orthogonal reactive groups are directed toward the opposite faces for promoting both surface attachment and introduction of functionalities suitable for promoting analyte detection. Hexasubstituted benzenes capable of covalent bonding to a surface and having functionalities capable of promoting detection of one or more analytes in fluids may be realized. An analytical response of the hexasubstituted benzenes or a change thereof may be correlated to an amount of at least one analyte present in a fluid, including both single- and multi-phase complex fluids.

## Claims

### Claim 1

A sensing method comprising:
exposing a fluid containing at least one analyte to a sensor construct comprising a hexasubstituted benzene having at least one sensing functionality capable of undergoing molecular association with the at least one analyte, wherein the fluid comprises an oilfield fluid comprising oil, gas, a treatment fluid, produced water, or any combination thereof;
determining an analytical response of the hexasubstituted benzene in the presence of the at least one analyte; and
correlating the analytical response or a change thereof to an amount of the at least one analyte present in the fluid.

### Claim 2 (depends on 1)

The method of claim 1, wherein the fluid comprises a single-phase or multi-phase complex fluid.

### Claim 3 (depends on 1)

The method of claim 1, further comprising:
Conducting or modifying a treatment operation based upon the analytical response or the change thereof.

### Claim 4 (depends on 1)

The method of claim 1, wherein the fluid comprises a multi-phase complex fluid selected from the group consisting of a liquid-liquid, solid-liquid, gas-liquid, solid-gas, or gas-liquid-solid complex fluid.

### Claim 5 (depends on 1)

The method of claim 1, wherein the hexasubstituted benzene is covalently bonded to a surface.

### Claim 6 (depends on 5)

The method of claim 5, wherein the surface is selected from the group consisting of a polymer surface, a metal surface, a ceramic surface, a glass surface, a cement surface, a wood surface, a geological surface, and any combination thereof.

### Claim 7 (depends on 5)

The method of claim 5, wherein the hexasubstituted benzene has a structure of
when covalently bonded to the surface;
wherein B is the surface;
wherein each A is a reaction product formed from opening of an epoxide with a nucleophile; and
wherein each L is a linking group connecting a benzylic carbon of the hexasubstituted benzene to the surface, each L being formed as a reaction product of an azide or a primary amine located upon the benzylic carbon.

### Claim 8 (depends on 7)

The method of claim 7, wherein each L comprises a cycloaddition reaction product of the azide, a secondary or tertiary amine reaction product of the primary amine, or a secondary or tertiary amide reaction product of the primary amine.

### Claim 9 (depends on 7)

The method of claim 7, wherein the hexasubstituted benzene has a structure of
wherein Nu1, Nu2 and Nu3 are each nucleophiles, and each Y is independently H or OH.

### Claim 10 (depends on 9)

The method of claim 9, wherein Nu1, Nu2 and Nu3 are each different.

### Claim 11 (depends on 9)

The method of claim 9, wherein at least one of Nu1, Nu2 and Nu3 includes functionality that is spectroscopically or electrochemically active to promote detection of the at least one analyte.

### Claim 12 (depends on 1)

The method of claim 1, wherein the sensor construct comprises a plate-based sensor or a flow-through sensor.