Manipulating hydrophilicity of conventional dye molecules for tracer applications

Patent metadata

Field	Value
Publication number	US-12286574-B2
Application number	US-202318193299-A
Country	US
Kind code	B2
Filing date	Mar 30, 2023
Priority date	Dec 13, 2021
Publication date	Apr 29, 2025
Grant date	Apr 29, 2025

Abstract

A composition includes a functionalized fluorescent dye. The functionalized fluorescent dye includes an isothiocyanate-containing dye that is functionalized with a functional group. The functional group includes a primary amine. The functionalized fluorescent dye can be mixed with a fluid to form a tracer fluid for tracing fluid flow in a subterranean formation.

First claim

What is claimed is:

1. A method of tracing fluid flow in a subterranean formation, comprising:
mixing a functionalized fluorescent tracer and a fluid to yield a tracer fluid, wherein the functionalized fluorescent tracer is prepared from an isothiocyanate-containing dye reacted with a primary amine, wherein:
the isothiocyanate-containing dye is selected from the group consisting of fluorescein isothiocyanate, Rhodamine B isothiocyanate, or tetramethylrhodamine isothiocyanate; and
the primary amine is selected from Group I or Group II, wherein:
Group I consists of aminomethanesulfonic acid, 2-aminoethanesulfonic acid, 3-amino-1-propanesulfonic acid, 2-aminoethyl(trimethyl)azanium, and 3-aminopropyl(trimethyl)azanium; and
Group II consists of 4-aminobenzenesulfonic acid, 3-aminobenzenesulfonic acid, 2-aminobenzenesulfonic acid, 3-amino-4-hydroxybenzenesulfonic acid, 4-amino-3-hydroxybenzenesulfonic acid, (4-aminophenyl)-trimethylazanium, 6-amino-4-hydroxy-2-naphthalenesulfonic acid, 4-amino-3-hydroxy-1-naphthalenesulfonic acid, 7-aminonaphthalene-1,3-disulfonic acid, 4-aminonaphthalene-1,7-disulfonic acid, 8-amino-1,3,6-naphthalenetrisulfonic acid, and 8-aminopyrene-1,3,6-trisulfonic acid;

flowing the tracer fluid into a first subterranean formation;
recovering a sample from the first subterranean formation or a second subterranean formation connected to the first subterranean formation; and
analyzing the sample for a fluorescent signal.

2. The method of claim 1 , comprising identifying the functionalized fluorescent tracer in the sample using fluorescence imaging, fluorescence spectroscopy, ultraviolet-visible (UV-Vis) spectroscopy, Fourier-transform infrared spectroscopy (FTIR), Raman spectroscopy, mass spectroscopy (MS), high performance liquid chromatography (HPLC), liquid chromatography-mass spectroscopy (LC-MS), or pyrolysis gas chromatography-mass spectroscopy (pyrolysis GC-MS), or any combination thereof.

3. The method of claim 1 , where in the sample is a fluid sample.

4. The method of claim 1 , wherein the fluid is a fracking fluid.

5. The method of claim 1 , wherein the fluid is a drilling mud.

6. The method of claim 1 , wherein the primary amine is selected from Group I.

7. The method of claim 1 , wherein the primary amine is selected from Group II.

8. The method of claim 1 , wherein the isothiocyanate-containing dye is fluorescein isothiocyanate.

9. The method of claim 8 , wherein the primary amine is selected from Group I.

10. The method of claim 8 , wherein the primary amine is selected from Group II.

11. The method of claim 1 , wherein the isothiocyanate-containing dye is Rhodamine B isothiocyanate.

12. The method of claim 11 , wherein the primary amine is selected from Group I.

13. The method of claim 11 , wherein the primary amine is selected from Group II.

14. The method of claim 1 , wherein the isothiocyanate-containing dye is tetramethylrhodamine isothiocyanate.

15. The method of claim 14 , wherein the primary amine is selected from Group I.

16. The method of claim 14 , wherein the primary amine is selected from Group II.

17. The method of claim 1 , wherein the isothiocyanate-containing dye is fluorescein isothiocyanate 5-isomer.

18. The method of claim 1 , wherein the isothiocyanate-containing dye is fluorescein isothiocyanate 6-isomer.

19. The method of claim 1 , wherein the isothiocyanate-containing dye is tetramethylrhodamine isothiocyanate 5-isomer.

20. The method of claim 1 , wherein the isothiocyanate-containing dye is tetramethylrhodamine isothiocyanate isomer R.

Assignees

• Saudi Arabian Oil Co

Inventors

• Wang Wei

Classifications

• C09B68/4253

  Sulfonic acid groups · CPC title

• C09K2211/1018

  Heterocyclic compounds · CPC title

• E21B47/11

  using tracers; using radioactivity · CPC title

• C09K8/62

  Compositions for forming crevices or fractures · CPC title

• C09K8/035

  Organic additives · CPC title