Granted Patent
B2
US 12,631,612 · App. 17/643,931 · Granted May 19, 2026
Fluorescent dye molecules for tracer applications in subterranean formations
Assignee:
Saudi Arabian Oil Company
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Abstract
A composition includes a functionalized fluorescent dye. The functionalized fluorescent dye includes an isothiocyanate-containing dye functionalized with a functional group. The functional group includes an aromatic compound with 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.
Claims (32)
1 . A composition comprising:
a functionalized fluorescent dye, wherein the functionalized fluorescent dye is formed from an isothiocyanate-containing dye reacted with a primary amine, wherein:
the isothiocyanate-containing dye is selected from the group consisting of fluorescein isothiocyanate, an isomer thereof, Rhodamine B isothiocyanate, an isomer thereof, tetramethylrhodamine isothiocyanate, and an isomer thereof, and
the primary amine is selected from the group consisting of 2-aminoanthracene, 6-chrysenamine, 9-aminophenanthrene, 2-aminofluorene, 9-aminoacridine, 9H-carbazol-2-amine, and 3-amino-9-ethylcarbazole.
2 . The composition of claim 1 , wherein the isothiocyanate-containing dye is tetramethylrhodamine isothiocyanate or an isomer thereof, and the primary amine is 2-aminofluorene.
3 . The composition of claim 1 , wherein the primary amine is 2-aminoanthracene, 1-aminopyrene, 6-chrysenamine, 9-aminophenanthrene, 2-aminofluorene, 9-aminoacridine, 9H-carbazol-2-amine, or 3-amino-9-ethylcarbazole.
4 . The composition of claim 1 , wherein the primary amine is 6-chrysenamine, 9-aminophenanthrene, or 2-aminoanthracene.
5 . The composition of claim 1 , wherein the primary amine is 2-aminofluorene, 9-aminoacridine, 9H-carbazol-2-amine, or 3-amino-9-ethylcarbazole.
6 . A method of making a functionalized fluorescent dye, comprising:
dissolving a water-soluble isothiocyanate-containing fluorescent dye in an aqueous solvent to yield an aqueous dye solution, wherein the water-soluble isothiocyanate-containing fluorescent dye is selected from the group consisting of fluorescein isothiocyanate, or an isomer thereof, Rhodamine B isothiocyanate, or an isomer thereof, tetramethylrhodamine isothiocyanate, and an isomer thereof;
dissolving a primary amine in an organic solvent to yield a primary amine solution, wherein the primary amine is selected from the group consisting of 2-aminoanthracene, 6-chrysenamine, 9-aminophenanthrene, 2-aminofluorene, 9-aminoacridine, 9H-carbazol-2-amine, and 3-amino-9-ethylcarbazole;
mixing the aqueous dye solution and the primary amine solution to form an emulsion;
separating the emulsion into an aqueous phase and an organic phase; and
extracting the functionalized fluorescent dye from the organic phase, wherein the functionalized fluorescent dye is a reaction product of the water-soluble isothiocyanate-containing dye and the primary amine.
7 . The method of claim 6 , wherein the aqueous solvent is deionized water.
8 . The method of claim 6 , wherein the aqueous solvent is a mixture of water and ethanol.
9 . The method of claim 8 , wherein a volumetric ratio of water to ethanol of the aqueous solvent is about 9:1.
10 . The method of claim 6 , wherein the organic solvent is chloroform.
11 . The method of claim 6 , wherein the organic solvent is cyclohexane.
12 . The method of claim 6 , wherein extracting the functionalized fluorescent dye from the organic phase comprises evaporating the organic solvent.
13 . A method of tracing fluid flow in a subterranean formation, comprising:
mixing a functionalized fluorescent tracer and a fluid to form a tracer fluid, wherein the functionalized fluorescent tracer is formed from an isothiocyanate-containing dye reacted with a primary amine, wherein:
the isothiocyanate-containing dye is selected from the group consisting of fluorescein isothiocyanate, an isomer thereof, Rhodamine B isothiocyanate, an isomer thereof, tetramethylrhodamine isothiocyanate, and an isomer thereof; and
the primary amine is selected from the group consisting of 2-aminoanthracene, 6-chrysenamine, 9-aminophenanthrene, 2-aminofluorene, 9-aminoacridine, 9H-carbazol-2-amine, and 3-amino-9-ethylcarbazole;
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.
14 . The method of claim 13 , comprising identifying the functionalized fluorescent tracer in the sample using fluorescence spectroscopy, fluorescence imaging, ultraviolet-visible (UV-Vis) spectroscopy, Fourier-transform infrared spectroscopy (FTIR), Raman spectroscopy, mass spectrometry (MS), high performance liquid chromatography (HPLC), liquid chromatography-mass spectrometry (LC-MS), or pyrolysis gas chromatograph-mass spectrometry (pyrolysis GC-MS), or any combination thereof.
15 . The method of claim 13 , where in the sample is a fluid sample.
16 . The method of claim 13 , wherein the sample is a solid sample.
17 . The method of claim 13 , wherein the fluid is a fracking fluid.
18 . The method of claim 13 , wherein the fluid is a drilling mud.
Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Jun 1, 2022
From: ARAMCO SERVICES COMPANY
To: SAUDI ARAMCO UPSTREAM TECHNOLOGY COMPANY
Reel/Frame 060066/0887 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Jun 1, 2022
From: SAUDI ARAMCO UPSTREAM TECHNOLOGY COMPANY
To: SAUDI ARABIAN OIL COMPANY
Reel/Frame 060067/0052 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Dec 16, 2021
From: WANG, WEI
To: ARAMCO SERVICES COMPANY
Reel/Frame 058410/0713 →
Continuity (1)
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