Fluorescent compound for tertiary oil recovery oil flooding viscosity detection and its preparation method and application

Abstract

The invention relates to the technical field of photochemical detection and analysis, and discloses a fluorescent compound used for oil flooding viscosity detection in tertiary oil recovery, a preparation method and application thereof. The fluorescent probe is 2-(4-(bis(4-methoxyphenyl)amino)phenyl)anthracene-9,10-dione (TPAMD). The probe compound of the present invention is composed of groups with aggregation-induced luminescent properties and anthraquinone groups with electron-withdrawing effects, and simultaneously have aggregation-induced luminescent properties and intramolecular charge transfer properties. The probe is easy to prepare, has a high yield, has a good response to viscosity, and has a good linear response. At the same time, it can cope with complex solvent environments and has good resistance to solvent interference. It can detect the viscosity of chemical displacement agents in the oil recovery field. , has the potential for analytical detection in many viscosity-sensitive fields such as chemistry, food, and the environment.

Description

technical field [0001] The invention relates to the technical field of photochemical detection and analysis, in particular to a fluorescent compound used for oil flooding viscosity detection in tertiary oil recovery and its preparation method and application. Background technique [0002] Petroleum, a viscous dark brown liquid, is known as "the blood of industry" and "flowing gold". Through later refining, countless downstream commodities can be obtained to support the development of modern civilization. Chemical industry, energy, textile, pharmaceutical and many other fields have varying degrees of field control power, and it is also an important non-renewable strategic energy source. In order to alleviate the direct and sharp contradiction between unlimited development and limited resources, increasing the oil recovery rate is the only way. After the primary oil recovery stage that depends on the eruption of formation pressure and the secondary oil recovery stage that inj...

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Problems solved by technology

Viscosity, as a physical indicator, has applications in many occasions. The advantages of fluorescence methods make it very suitable for detecting changes in viscosity. However, so far, most of the literature has used fluorescent probes for biological Viscosity detection and analysis in the field, for example: In a research paper published in Journal of Materials Chemistry B, 2018, 6, 2894-2900 in 2018, a rhodamine derivative was used for the detection of intracellular viscosity changes. Cells are full of organelles, macromolecular proteins, lipids, nucleic acids, sugars, etc., and the crowding of the cytoplasm may hinder the diffusion of solutes, thereby affecting some key metabolic functions, including protein folding, enzyme catalysis, intracellular signal transduction , intracellular transport and other functions, one of the passive factors that determine the diffusion of solutes is viscosity, and whether the intracellular metabolism is normal can be indirectly analyzed by detecting the change of viscosity; however, the synthesis of molecular probes described in the literature is relatively complicated, and the fluorescent probe It may have the aggregation-induced fluorescence quenching (ACQ) effect, that is, the fluorescence quenching phenomenon will occur when the dose is used at a high concentration. crosstalk

Similarly, in the article published in Journal of Materials Chemistry B, 2017, 5, 2743-2749, a molecular probe for detecting intracellular microscopic viscosity was prepared. Although the probe has two-photon imaging, the preparation is complicated. The emission wavelength is short, the Stokes shift is short, the molecule as a whole has a rigid conjugated structure, and has a typical ACQ effect, which makes it difficult to achieve objective application of large doses in the industrial field

Another example is the research paper published in SpectrochimicaActa Part A: Molecular and Biomolecular Spectroscopy, 2019, 214, 339-347, which also prepared three fluorescent probe molecules for viscosity detection, which are also applied to the detection of intracellular microscopic viscosity. Fluorescent probe molecules can "Turn-on" fluorescence when the viscosity increases because of the inhibition of twisted intramolecular charge transfer (TICT), but there are disadvantages of complex preparation, and because the three molecules are all conjugated aromatic structures , tends to π-π stacking aggregation in highly polar solvents, has the property of aggregation-induced quenching, complex synthesis, and the final yield reduction effect generally brought by the yield per step is not conducive to large-scale application in industrial fields

[0006] Although the current fluorescence technology for viscosity detection and the corresponding developed probes have made some progress in the field of biological imaging, there are few applications of fluorescence technology for the detection and analysis of chemical flooding viscosity in tertiary oil recovery.

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