A dentatin benzaldehyde-based molecular gyroscope, a preparation method and application thereof in industrial vegetable oil agents

Abstract

The application belongs to the technical field of industrial plant oil agent analysis and detection, and provides a dentatin benzaldehyde-based molecular gyroscope, a preparation method and application of the molecular gyroscope in industrial plant oil agents, and the preparation method is as follows: (1) an organic alkali solution is added to a dentatin solution and mixed to obtain a pre-activation system; (2) the pre-activation system and a 3,5-dimethylbenzaldehyde solution are mixed and subjected to a coupling condensation reaction to obtain the dentatin benzaldehyde-based molecular gyroscope; the dentatin benzaldehyde-based molecular gyroscope is prepared from natural plant source product dentatin and natural aromatic derivative 3,5-dimethylbenzaldehyde as raw materials through a conjugate coupling reaction, the raw materials are derived from nature or biodegradable natural product derivatives, and the source is rich and the environmental compatibility is excellent, so that the molecular gyroscope is endowed with green degradable characteristics from the source, and completely meets the concept of low-carbon sustainable development.

Description

Technical Field

[0001] This invention relates to the field of industrial vegetable oil analysis and detection technology, and in particular to a styrax benzaldehyde-based molecular gyroscope, its preparation method, and its application in industrial vegetable oils. Background Technology

[0002] Industrial oils are crucial functional materials in modern industrial production, widely used in textiles, chemical fibers, metal processing, leather, rubber and plastics, and other fields. They play core roles in lubrication, rust prevention, emulsification, antistatic properties, and smoothing of aggregates, playing a vital role in ensuring processing precision, improving product quality, and stabilizing production processes. In the selection of raw materials for industrial oils, natural oils and their modified products are widely used due to their excellent compatibility and environmental friendliness, with coconut oil being a particularly widely applied core raw material. Coconut oil can be directly incorporated into oil systems as a lubricating component to meet lubrication needs under light-load conditions; its derivatives, such as cocoyl acid, coconut esters, and surfactants, can further optimize the emulsifying, rust-preventing, and antistatic properties of the oil, adapting to various industrial oil formulations. With its outstanding practicality and environmental friendliness, it has mature and widespread applications in various industrial oil products. In industrial oil and industrial oil systems, natural coconut oil is a highly valuable renewable basic raw material, occupying an important position in the industry due to its unique fatty acid structure and excellent compatibility. In practical industrial applications, viscosity can be differentiated by adjusting fatty acid composition, raw material origin, and refining process to meet the diverse needs of various industrial scenarios such as textiles, chemical fibers, metal processing, leather auxiliaries, and rubber and plastic lubricants. High micro-viscosity natural coconut oil forms dense films with high film strength and excellent adhesion and shaping capabilities, making it suitable for applications requiring high lubrication, film formation, and protective performance, such as spinning oils, rust inhibitors, and leather fatliquoring. However, it suffers from poor low-temperature fluidity and insufficient wetting and penetration. Low micro-viscosity natural coconut oil exhibits excellent fluidity, spreading, and penetration, making it more suitable for processing scenarios with stringent requirements for rapid dispersion and efficient wetting, such as metal cutting fluids, textile smoothers, and environmentally friendly release agents. However, it suffers from thinner oil films and weaker long-term lubrication and retention. Therefore, accurately monitoring the micro-viscosity of natural coconut oil is crucial for optimizing its industrial refining process, improving the overall performance of industrial oils, and precisely matching the specific needs of different operating conditions. Developing tools capable of rapid, in-situ, and visual measurement of its micro-viscosity is imperative.

[0003] In the field of fluid oil analysis and testing, photochemical technology, relying on molecular tools, can achieve real-time, in-situ, and visual monitoring of micro-region viscosity. This static photoresponse mode can effectively avoid the shear thinning error caused by traditional shear-based testing, while significantly reducing sample consumption, simplifying operation steps, shortening the testing cycle, and significantly improving detection efficiency and data accuracy. However, at present, the accurate measurement of the physical micro-region viscosity of natural coconut oil for industrial vegetable oils not only generally lacks adaptable molecular-level tools, but also lacks molecular tools reconstructed from green natural products. Such tools are both environmentally friendly and biocompatible, and are more in line with the natural and green product attributes of coconut oil, representing a core technological gap in the current coconut oil testing field. Summary of the Invention

[0004] The purpose of this invention is to overcome the problems of high sample volume and complex detection methods required by existing methods for detecting the gelation degree of industrial oils, and to provide a styrax benzaldehyde-based molecular gyroscope, its preparation method, and its application in industrial vegetable oils.

[0005] To achieve the above-mentioned objectives, the present invention provides the following technical solution: This invention provides a dental amylin benzaldehyde-based molecular gyroscope, the structure of which is shown below: .

[0006] This invention provides a method for preparing the aforementioned acetamiprid benzaldehyde-based molecular gyroscope, comprising the following steps: (1) The organic base solution was added to the amycin solution and mixed to obtain a pre-activated system; (2) The pre-activated system and 3,5-dimethylbenzaldehyde solution were mixed and coupled together to obtain the damizobenzaldehyde-based molecular gyroscope.

[0007] Preferably, the concentration of the amycin solution in step (1) is 1~3M; Amifentanil solution contains amifentanil, alcohol solvents, and organic solvents; The alcohol solvent is one or more of methanol, ethanol, ethylene glycol, propanol and 1,2-propanediol; The organic solvent is one or more of acetonitrile, tetrahydrofuran, acetone, N,N-dimethylformamide, ethyl acetate, and dimethyl sulfoxide; The volume ratio of alcohol solvents to organic solvents is 1 to 6:1.

[0008] Preferably, the organic base solution in step (1) comprises artificial organic base, natural organic base and solvent; The artificial organic base is one or more of triethylamine, 4-dimethylaminopyridine, N,N-diisopropylethylamine, pyridine, 4-diethylaminopyridine and N,N,N',N'-tetramethylethylenediamine; Natural organic bases are one or more of choline, betaine, and acetylcholine; The solvent is one or more of ethanol, methanol, propylene glycol, ethylene glycol, tetrahydrofuran, dioxane, N,N-dimethylformamide and ethyl acetate; The molar ratio of artificial organic bases to natural organic bases is 1:1~3; The molar ratio of artificial organic base to guanylic acid is 0.5~2:1.

[0009] Preferably, the additive in step (1) is a spray additive; the spray rate of the spray additive is 5~10mL / min; In step (1), the mixing temperature is 20~30℃, the rotation speed is 1200~2000rpm, and the time is 0.5~1.5h; The mixture is subjected to ultrasound simultaneously, with an ultrasound power of 100~400W and a single session duration of 5~20min; the interval between two adjacent ultrasound sessions is 25~35min.

[0010] Preferably, the solvent for the 3,5-dimethylbenzaldehyde solution in step (2) is one or more of ethanol, methanol, propylene glycol, ethylene glycol, tetrahydrofuran, dioxane, N,N-dimethylformamide and ethyl acetate; The concentration of 3,5-dimethylbenzaldehyde solution is 1~6M.

[0011] Preferably, the molar ratio of 3,5-dimethylbenzaldehyde to dextrin is 1 to 5:1.

[0012] Preferably, the mixing drop rate in step (2) is 5~15 mL / min; In step (2), the target reaction temperature for the coupling condensation reaction is 60~100℃, the heating rate is 1~5℃ / min, the ultrasonic power is 250~400W, the time for a single ultrasonic treatment is 5~15min, and the interval between two ultrasonic treatments is 3~8min. The coupling condensation reaction takes 2 to 24 hours.

[0013] This invention also provides the application of the aforementioned acetamiprid benzaldehyde-based molecular gyroscope in the physical micro-area viscosity measurement of industrial vegetable oils.

[0014] This invention also provides a method for measuring the physical micro-area viscosity of industrial vegetable oils, comprising the following steps: The benzaldehyde-based molecular gyroscope, solvent, and test sample of the damicin were mixed, and fluorescence excitation was performed to complete the determination. The ratio of the amount of the acetamiprid benzaldehyde-based molecular gyroscope, solvent, and test sample is 1~100 μmol: 1 L: 0.003 L; The solvent is one or more of ethyl acetate, apple ester, and triacetyl ester; The excitation wavelength for fluorescence excitation is 300~400nm.

[0015] This invention provides a dentamicin benzaldehyde-based molecular gyroscope, which is prepared by the following method: (1) adding an organic base solution to a dentamicin solution and mixing to obtain a pre-activated system; (2) mixing the pre-activated system with a 3,5-dimethylbenzaldehyde solution and performing a coupling condensation reaction to obtain the dentamicin benzaldehyde-based molecular gyroscope; the beneficial effects of this invention are as follows: (1) The DMFC molecular gyroscope provided by this invention is precisely constructed by conjugation coupling reaction using DMFC (a natural plant-derived product that is widely found in umbelliferous plants and is green and renewable) and 3,5-dimethylbenzaldehyde (a natural aromatic derivative) as raw materials. The raw materials are all derived from natural or biodegradable natural product derivatives, with abundant sources and excellent environmental compatibility. This gives the molecular gyroscope green and degradable characteristics from the source, which is in line with the concept of low-carbon and sustainable development. The successful preparation of this molecule breaks the application limitations of traditional natural products and realizes the high-value interdisciplinary expansion of natural products in the field of internal rotation functional molecules. It can not only meet the detection needs of multiple fields, but also shows unique compatibility for natural oil systems such as coconut oil. Its preparation adopts a one-step process, which is simple and efficient. It effectively reduces solvent consumption and yield loss in complicated steps, reduces preparation costs, and uses only milligrams. The application cost is low, while meeting the requirements of rapid large-scale manufacturing. It is both green and environmentally friendly and practical.

[0016] (2) The core advantage of the DMFC molecular gyroscope (DMFC) stems from its unique flexible conjugated internal rotation structure, which endows it with highly sensitive response characteristics to the micro-environment. In different systems (especially coconut oil systems), molecules can exhibit different internal rotation states depending on the viscosity / gelation degree of the micro-area: in low-viscosity coconut oil or low-gelation degree industrial oil samples, molecules can rotate freely, and the excited state energy is mainly dissipated through mechanical rotation, resulting in a weak light signal; while in high-viscosity coconut oil or high-gelation degree samples, molecular rotation is significantly suppressed, and energy is released through radiative transitions, generating a strong light signal. The sensitivity coefficient of this molecular gyroscope to environmental changes is as high as 0.72, and the detection limit is as low as 1.034 cP, which can accurately capture the subtle viscosity fluctuations in the micro-area of ​​coconut oil and industrial oil gels; its chromogenic wavelength peak is 481 nm, exhibiting typical cyan-blue light, with extremely strong visualization effect, and the gelation degree or viscosity grade of coconut oil can be directly judged intuitively by the light signal intensity, realizing real-time visual monitoring of the coconut oil system. In addition, DMFC has a stable chemical structure and can remain stable for a long time in complex coconut oil matrix and industrial oil environment. It also has excellent pH tolerance, solvent polarity compatibility and light stability. Even under different processing conditions of coconut oil, it can still maintain stable signal output, providing reliable support for the quality control of coconut oil system.

[0017] (3) The DMFC molecular gyroscope, a molecular-level in-situ detection tool, can achieve undisturbed measurement of the gelation degree / viscosity of coconut oil and industrial oil gel systems. Its measurement process does not require the application of external stresses such as rotation or shear, perfectly avoiding the shear thinning effect caused by shearing in traditional shear-based measurement methods when processing industrial vegetable oil gels containing pseudoplastic components, as well as the resulting microenvironment damage and distortion of detection results. This molecular gyroscope has excellent compatibility with the coconut oil system, and can accurately capture the dynamic changes in micro-region viscosity and gelation degree during coconut oil processing in a relatively static state, providing real-time, non-destructive, and visualized data support for the process optimization (such as hydrogenation, emulsification, and gelation control) and quality monitoring of coconut oil products. Its unique detection mechanism and excellent adaptability fill the technical gap in the accurate monitoring of micro-region performance of natural oil systems, and have enormous application value and market potential in the fields of coconut oil deep processing and the development of industrial oil gel products, providing an innovative molecular tool for the quality upgrading of the natural oil and industrial oil industry. Attached Figure Description

[0018] Figure 1 This is a schematic diagram illustrating the working mechanism of the dental amiocin benzaldehyde-based molecular gyroscope of the present invention. Figure 2 The mass spectrum of the gyroscope containing the benzaldehyde-based motif of Example 1 is shown. Figure 3The carbon NMR spectrum of the gyroscope containing the benzaldehyde-based motif of Example 1 is shown below. Figure 4 The spectra of the toothed amiodarone benzaldehyde-based molecular gyroscope in Example 1 at different viscosities are shown. Figure 5 This is a linear fit graph between the optical signal intensity and solution viscosity of the toothed amiodarone benzaldehyde-based molecular gyroscope in Example 1. Figure 6 The spectrum of the tooth-like benzaldehyde-based molecular gyroscope in Example 1 at different pH solutions; Figure 7 The image shows the photostability test results of the amycin benzaldehyde-based molecular gyroscope in glycerol and purified water in Example 1. Figure 8 The Stokes displacement diagram of the toothed amiodarone benzaldehyde-based molecular gyroscope of Example 1; Figure 9 The detection limit diagram for the phenylaldehyde-based molecular gyroscope of amiodarone in Example 1 is shown. Figure 10 The emission spectra of the dinoflagellate benzaldehyde-based molecular gyroscope prepared in Example 1 in different fluidized coconut oils are shown. Detailed Implementation

[0019] This invention provides a dental amylin benzaldehyde-based molecular gyroscope, the structure of which is shown below: .

[0020] This invention provides a method for preparing the aforementioned acetamiprid benzaldehyde-based molecular gyroscope, comprising the following steps: (1) The organic base solution was added to the amycin solution and mixed to obtain a pre-activated system; (2) The pre-activated system and 3,5-dimethylbenzaldehyde solution were mixed and coupled together to obtain the damizobenzaldehyde-based molecular gyroscope.

[0021] In this invention, the concentration of the amycin solution in step (1) is preferably 1~3M, more preferably 1.5~2.5M, and even more preferably 1.8~2.2M.

[0022] In this invention, the amycin solution contains amycin, an alcohol solvent, and an organic solvent.

[0023] In this invention, the alcohol solvent is one or more of methanol, ethanol, ethylene glycol, propanol and 1,2-propanediol.

[0024] In this invention, the organic solvent is one or more of acetonitrile, tetrahydrofuran, acetone, N,N-dimethylformamide, ethyl acetate, and dimethyl sulfoxide.

[0025] In this invention, the volume ratio of alcohol solvent to organic solvent is preferably 1 to 6:1, more preferably 2 to 5:1, and even more preferably 3 to 4:1.

[0026] In this invention, abamectin is added to a mixture of an alcohol solvent and an organic solvent and stirred. The stirring temperature is preferably 25-50°C, more preferably 30-45°C, and even more preferably 35-40°C; the stirring speed is preferably 300-1200 rpm, more preferably 500-1000 rpm, and even more preferably 700-800 rpm; the ultrasonic power is preferably 150-400 W, more preferably 200-350 W, and even more preferably 250-300 W; the ultrasonic frequency is preferably 10-40 kHz, more preferably 15-35 kHz, and even more preferably 20-30 kHz; the stirring time is preferably 0.3-1 h, more preferably 0.4-0.9 h, and even more preferably 0.5-0.8 h; after stirring, abamectin solution is obtained.

[0027] In this invention, the organic base solution in step (1) comprises artificial organic base, natural organic base and solvent.

[0028] In this invention, the artificial organic base is one or more of triethylamine, 4-dimethylaminopyridine, N,N-diisopropylethylamine, pyridine, 4-diethylaminopyridine and N,N,N',N'-tetramethylethylenediamine.

[0029] In this invention, the natural organic base is one or more of choline, betaine and acetylcholine.

[0030] In this invention, the solvent is one or more of ethanol, methanol, propylene glycol, ethylene glycol, tetrahydrofuran, dioxane, N,N-dimethylformamide, and ethyl acetate; the solvent is used in excess to ensure the dissolution of the alkali; an artificial organic alkali is added to the solvent, and then a natural organic alkali is added and stirred. The stirring temperature is preferably 20~30℃, more preferably 22~28℃, and even more preferably 24~26℃; the stirring time is preferably 0.5~1.5h, more preferably 0.6~1.4h, and even more preferably 0.8~1.2h.

[0031] In this invention, the molar ratio of artificial organic base to natural organic base is preferably 1:1 to 3, more preferably 1:1.5 to 2.5, and even more preferably 1:1.8 to 2.2.

[0032] In this invention, the molar ratio of artificial organic base to guanylic acid is preferably 0.5 to 2:1, more preferably 1 to 1.5:1, and even more preferably 1.2 to 1.3:1.

[0033] In this invention, the addition in step (1) is by spraying; the spraying rate of the spraying is preferably 5~10mL / min, more preferably 6~9mL / min, and even more preferably 7~8mL / min; after all the organic base solution is sprayed in, the system is placed in a shaker for mixing.

[0034] In this invention, the mixing temperature in step (1) is preferably 20~30℃, more preferably 22~28℃, and even more preferably 24~26℃; the rotation speed is preferably 1200~2000rpm, more preferably 1400~1800rpm, and even more preferably 1600~1700rpm; the time is preferably 0.5~1.5h, more preferably 0.6~1.4h, and even more preferably 0.8~1.2h.

[0035] In this invention, ultrasound is performed simultaneously with the mixing process, and the ultrasound is performed intermittently. The power of the ultrasound is preferably 100~400W, more preferably 150~350W, and even more preferably 200~300W. The duration of a single ultrasound is preferably 5~20min, more preferably 10~15min, and even more preferably 12~13min. The interval between two adjacent ultrasounds is preferably 25~35min, more preferably 26~34min, and even more preferably 28~32min.

[0036] In this invention, the solvent for the 3,5-dimethylbenzaldehyde solution in step (2) is one or more of ethanol, methanol, propylene glycol, ethylene glycol, tetrahydrofuran, dioxane, N,N-dimethylformamide and ethyl acetate.

[0037] In this invention, the concentration of the 3,5-dimethylbenzaldehyde solution is preferably 1-6 M, more preferably 2-5 M, and even more preferably 3-4 M.

[0038] In this invention, 3,5-dimethylbenzaldehyde and a solvent are mixed and stirred, with intermittent ultrasound occurring during the stirring process. The ultrasound power is preferably 100-400W, more preferably 150-350W, and even more preferably 200-300W. The duration of a single ultrasound session is preferably 5-10 min, more preferably 6-9 min, and even more preferably 7-8 min. The interval between two adjacent ultrasound sessions is preferably 10-30 min, more preferably 15-25 min, and even more preferably 18-22 min. The stirring speed is preferably 600-1800 rpm, more preferably 800-1600 rpm, and even more preferably 1000-1400 rpm. The stirring time is preferably 0.2-1 h, more preferably 0.3-0.9 h, and even more preferably 0.4-0.8 h.

[0039] In this invention, the molar ratio of 3,5-dimethylbenzaldehyde to styrax is preferably 1 to 5:1, more preferably 2 to 4:1, and even more preferably 2.5 to 3.5:1.

[0040] In this invention, the mixing in step (2) is to add a 3,5-dimethylbenzaldehyde solution dropwise into the system. The preferred dropping rate is 5~15 mL / min, more preferably 6~14 mL / min, and even more preferably 8~12 mL / min. The heating is started at the beginning of the dropping.

[0041] In this invention, the target reaction temperature of the coupling condensation reaction in step (2) is preferably 60~100℃, more preferably 70~90℃, and even more preferably 75~85℃; the heating rate is preferably 1~5℃ / min, more preferably 1.5~4.5℃ / min, and even more preferably 2~4℃ / min; stirring and sonication are maintained during the reaction, the stirring speed is preferably 1500~2000rpm, more preferably 1600~1900rpm, and even more preferably 1700~1800rpm; the sonication power is preferably 250~400W, more preferably 300~350W, and even more preferably 320~330W; the single sonication time is preferably 5~15min, more preferably 6~14min, and even more preferably 8~12min; the interval between two sonications is preferably 3~8min, more preferably 4~7min, and even more preferably 5~6min.

[0042] In this invention, the coupling condensation reaction time is preferably 2-24 h, more preferably 5-20 h, and even more preferably 10-15 h.

[0043] In this invention, after the coupling condensation reaction is completed, nitrogen blowing and depressurization, fractional extraction, chromatography purification, and low-temperature crystallization are performed sequentially to obtain the dinoflagrolide benzaldehyde-based molecular gyroscope.

[0044] In this invention, the system after the reaction is completed is cooled to room temperature and concentrated by nitrogen blowing. The pressure is preferably -0.08 to -0.06 MPa, more preferably -0.075 to -0.065 MPa, and even more preferably -0.072 to -0.068 MPa. The temperature is preferably 30 to 50°C, more preferably 35 to 45°C, and even more preferably 38 to 42°C. After concentration to 1 / 6 of the original volume, the solution is removed by vacuum distillation. The pressure of vacuum distillation is preferably -0.09 to -0.07 MPa, more preferably -0.085 to -0.075 MPa, and even more preferably -0.082 to -0.078 MPa. The temperature is preferably 40 to 60°C, more preferably 45 to 55°C, and even more preferably 48 to 52°C. The concentrated product is obtained.

[0045] The concentrated product is added to an extractant for fractional extraction. The extractant contains ethyl acetate and water, with a volume ratio of ethyl acetate to water preferably of 1-8:1, more preferably 2-7:1, and even more preferably 3-6:1. The product is then placed in a separatory funnel and shaken for 5-10 min, more preferably 6-9 min, and even more preferably 7-8 min. Ultrasonic assisted separation is performed, with an ultrasonic power preferably of 150-250 W, more preferably 160-240 W, and even more preferably 180-220 W, for 5-20 min, more preferably 10-15 min, and even more preferably 12-13 min. The organic phase is collected. The extraction is repeated 1-3 times, the organic phases are combined, and the product is concentrated again by nitrogen blowing until no solvent residue remains, yielding the crude product.

[0046] The crude product is purified by chromatography as follows: the crude product is dissolved in the eluent to prepare a sample solution. The eluent contains dichloromethane and methanol, and the volume ratio of dichloromethane to methanol is preferably 5~30:1, more preferably 10~25:1, and even more preferably 15~20:1. The concentration of the sample solution is preferably 5~10 mg / mL, more preferably 6~9 mg / mL, and even more preferably 7~8 mg / mL. A chromatography column is packed with 300~600 mesh chromatographic grade silica gel powder, and gradient elution is performed with the same eluent. The target component eluent is collected by a UV detector (detection wavelength 254 nm), concentrated to dryness by nitrogen blowing, and the purified intermediate is obtained.

[0047] The low-temperature crystallization process is as follows: the purified intermediate is placed in a mixed system containing ethanol and water, preferably with a volume ratio of ethanol to water of 1:3 to 12, more preferably 1:4 to 10, and even more preferably 1:6 to 8; the solid content is preferably 5 to 30 mg / mL, more preferably 10 to 25 mg / mL, and even more preferably 15 to 20 mg / mL; the mixture is then dispersed in an ultrasonic cleaner, preferably with an ultrasonic power of 50 to 200 W, more preferably 100 to 150 W, and even more preferably 120 to 130 W. The dispersion time is preferably 5-20 min, more preferably 10-15 min, and even more preferably 12-13 min; after dispersion, the mixture is allowed to stand at a temperature preferably 0-8℃, more preferably 2-6℃, and even more preferably 4-5℃ for a time preferably 2-12 h, more preferably 4-10 h, and even more preferably 6-8 h; the crystalline powder precipitated during standing is then subjected to vacuum filtration, with 1-3 layers of rapid filter paper used for vacuum filtration, and the vacuum pressure preferably -0.09 to -0.07 MPa, and even more preferably -0. The pressure is 0.085~-0.075MPa, more preferably -0.082~-0.078MPa; during the filtration process, the crystallizer is repeatedly washed 2~4 times with a mixture of ethanol and water to remove surface impurities. The volume ratio of ethanol to water is preferably 1:5~20, more preferably 1:10~15, and more preferably 1:12~13; then pre-cooling is performed. The pre-cooling temperature is preferably -5~-25℃, more preferably -10~-20℃, and more preferably -15~-18℃; the pre-cooling time is preferably 1~3h, more preferably... The freezing time is selected to be 1.5~2.5h, more preferably 1.8~2.2h; after pre-cooling, freeze drying is performed, and the freeze drying temperature is preferably -15~-50℃, more preferably -20~-40℃, more preferably -25~-35℃; the vacuum degree of freeze drying is preferably ≤10Pa, more preferably ≤8Pa, more preferably ≤5Pa; the freeze drying time is preferably 12~24h, more preferably 14~22h, more preferably 16~20h, and after freeze drying, a dentamicin benzaldehyde-based molecular gyroscope is obtained.

[0048] This invention also provides the application of the aforementioned acetamiprid benzaldehyde-based molecular gyroscope in the physical micro-area viscosity measurement of industrial vegetable oils.

[0049] This invention also provides a method for measuring the physical micro-area viscosity of industrial vegetable oils, comprising the following steps: The benzaldehyde-based molecular gyroscope, solvent, and test sample of the damicin were mixed, and fluorescence excitation was performed to complete the determination. The preferred ratio of the amount of the acetamiprid benzaldehyde-based molecular gyroscope, solvent, and test sample is 1~100 μmol:1 L:0.003 L, more preferably 20~80 μmol:1 L:0.003 L, and even more preferably 40~60 μmol:1 L:0.003 L.

[0050] In this invention, the solvent is one or more of ethyl acetate, apple ester, and triacetylglycerol.

[0051] In this invention, the excitation wavelength of fluorescence excitation is preferably 300~400nm, more preferably 320~380nm, and even more preferably 340~360nm.

[0052] In this invention, the test sample is a liquid oil product, specifically liquid coconut oil, glycerol, etc.

[0053] The working mechanism of the dental amycin benzaldehyde-based molecular gyroscope of the present invention is as follows: Figure 1 As shown.

[0054] The technical solutions provided by the present invention will be described in detail below with reference to the embodiments, but they should not be construed as limiting the scope of protection of the present invention.

[0055] Example 1

[0056] 230.22 g (1 mol) of the natural product amycin was added to a mixture of ethanol and tetrahydrofuran (volume ratio 3.5:1), and stirred continuously at 37.5 °C and 750 rpm. Dynamic ultrasonic treatment (power 275 W, frequency 25 kHz) was applied simultaneously. The stirring-ultrasound synergistic effect lasted for 0.65 h to obtain a 2 M amycin solution. 402.54 g (3 mol) of 3,5-dimethylbenzaldehyde was added to a mixture of ethanol and tetrahydrofuran. The mixture was stirred at 25°C at a stirring speed of 1200 rpm, accompanied by intermittent ultrasonic assistance (power 250W, ultrasonication for 7.5 min every 20 min of stirring) for 0.6 h to obtain a 3M 3,5-dimethylbenzaldehyde solution. 101.19 g (1 mol) of the artificial organic base triethylamine and 242.36 g (2 mol) of the natural organic base choline (the molar ratio of artificial organic base to natural organic base is 1:2) were mixed and stirred continuously at 25°C for 1.0 h to obtain a homogeneous organic base solution. The above-mentioned organic base solution was added to the amycin solution by spraying at a rate of 7.5 mL / min. After spraying, the solution was placed in a constant temperature shaker (temperature 25℃, speed 1600 rpm) and continuously shaken for 1.0 h to achieve pre-activation of amycin. During the shaking period, short-term ultrasound (power 250 W, duration 12.5 min) was applied every 30 min. While maintaining a constant shaking speed of 1600 rpm, 3,5-dimethylbenzaldehyde solution was added dropwise to the above mixture at a rate of 10 mL / min using a constant flow pump. During the dropwise addition, a gradient temperature program was started, with the temperature increase rate controlled at 3℃ / min, gradually increasing to the target temperature of 80℃. During the reaction, the shaking was maintained (speed 1750 rpm), and ultrasonic assistance was continuously provided (power 325 W, intermittent: 10 min of ultrasonication followed by 5 min of rest). After 13 h of reaction, the reaction solution containing the daminovic benzaldehyde molecular gyroscope was obtained by monitoring the reaction until the starting material spot disappeared using thin-layer chromatography (TLC).

[0057] After the reaction was completed, the resulting reaction solution was subjected to nitrogen blowing under reduced pressure, fractional extraction, chromatography purification, and low-temperature crystallization in sequence. The specific operation steps are as follows: The reaction solution was cooled to room temperature and transferred to a nitrogen blower (pressure -0.07 MPa, temperature 40℃) to be concentrated to 1 / 6 of the original volume. Then, the solvent was further removed by vacuum distillation (-0.08 MPa, temperature 50℃) to obtain the concentrated product. Add a mixture of ethyl acetate and purified water at a volume ratio of 4.5:1 to the concentrated product, place it in a separatory funnel and shake vigorously for 7.5 min, then perform ultrasonic-assisted separation (power 200 W, duration 12.5 min), collect the organic phase; repeat the extraction twice, combine the organic phases, and concentrate again with nitrogen until no solvent residue remains to obtain the crude product; The crude product was dissolved in a mixture of dichloromethane and methanol (volume ratio 17.5:1) to prepare a sample solution with a concentration of 7.5 mg / mL. A chromatography column packed with 450-mesh chromatographic grade silica gel powder was used for gradient elution with the same eluent. The eluent of the target component was collected by UV detector (detection wavelength 254 nm) and concentrated to dryness by nitrogen blowing to obtain the purified intermediate. The purified intermediate was redispersed in a 1:7.5 volume ratio of ethanol and purified water, with a solid content of 17.5 mg / mL. The mixture was then placed in an ultrasonic cleaner (125 W, 12.5 min) to promote uniform dispersion. Subsequently, it was transferred to a 4°C cryogenic incubator and allowed to stand for 7 hours to slowly precipitate crystals. The crystals were then filtered using two layers of rapid filter paper (under reduced pressure of -0.08 MPa). During filtration, the crystals were repeatedly rinsed three times with a 1:12.5 volume ratio of ethanol and purified water to remove surface impurities. The crystals were then placed in a freeze-drying oven, pre-frozen at -15°C for 2 hours, then cooled to -32.5°C, maintaining a vacuum of ≤10 Pa, and freeze-dried for 18 hours to obtain the DMFC-based benzaldehyde molecular gyroscope, with a yield of 320.7 g and a yield rate of 92.6%.

[0058] The relative molecular mass of the prepared DMFC benzaldehyde-based gyroscope was analyzed by mass spectrometry, and the results are as follows: Figure 2 As shown. By Figure 2 It is known that the relative molecular mass of the DMFC benzaldehyde-based gyroscope is 346.39106 [M]. + The molecular formula of formula 1 is C 22 H 18 O4, with a theoretical relative mass estimate of 346.38200, shows that the product obtained in Example 1 is consistent with the target product in terms of relative molecular mass. Furthermore, the chemical structure of the obtained product was tested, and its carbon NMR spectrum is shown below. Figure 3 As shown. From Figure 3 From this, we can know that 13 C NMR (101 MHz, DMSO-d6) δ 182.2, 164.8, 163.1, 158.5, 157.8, 146.8, 139.8, 135.9, 135.1, 131.8, 124.1, 119.8, 117.7, 112.7, 108.8, 105.8, 91.3, 61.3, 22.1, confirming the carbon skeleton shift in its molecular structure, thus identifying it as the target product, DMFC, a benzaldehyde-based molecular gyroscope.

[0059] Example 2

[0060] 230.22 g (1 mol) of the natural product amycin was added to a mixture of methanol and acetonitrile (volume ratio 1:1), and stirred continuously at 25℃ (minimum temperature) at a stirring speed of 300 rpm. Simultaneous dynamic ultrasonic treatment (power 150 W, frequency 10 kHz) was applied. The stirring-ultrasonic synergistic effect lasted for 1.0 h (the minimum temperature corresponds to the maximum time), resulting in a amycin solution with a concentration of 1 M (minimum concentration). 134.18 g (1 mol) of 3,5-dimethylbenzaldehyde was added to methanol and stirred at room temperature at a stirring rate of 600 rpm, accompanied by intermittent ultrasonic assistance (power 100 W, ultrasonic for 5 min every 10 min of stirring) for 1.0 h to obtain a 1 M 3,5-dimethylbenzaldehyde solution. 50.60 g (0.5 mol) of artificial organic base triethylamine and 60.59 g (0.5 mol) of natural organic base choline (molar ratio of artificial organic base to natural organic base 1:1) were mixed and stirred continuously at room temperature for 1.5 h to obtain a homogeneous organic base solution. The above-mentioned organic base solution was added to the amycin solution by spraying at a rate of 5 mL / min. After spraying, the solution was placed in a constant temperature shaker (temperature 25℃, speed 1200 rpm) and continuously shaken for 1.5 h to achieve pre-activation of amycin. During the shaking period, short-term ultrasound (power 400 W, duration 5 min) was applied every 30 min. Keeping the shaking speed constant at 1200 rpm, 3,5-dimethylbenzaldehyde solution was added dropwise to the above mixture at a rate of 5 mL / min using a constant flow pump. During the dropwise addition, a gradient temperature program was started, with the temperature increase rate controlled at 1℃ / min, gradually increasing to the target temperature of 60℃. During the reaction, the shaking speed was maintained at 1500 rpm, and ultrasonic assistance was continuously provided (power 250 W, intermittent: 10 min of ultrasonication followed by 5 min of rest). After 24 h of reaction, the reaction solution containing the daminov benzaldehyde molecular gyroscope was obtained by monitoring the reaction until the starting material spot disappeared using thin-layer chromatography (TLC).

[0061] After the reaction was completed, the resulting reaction solution was subjected to nitrogen blowing under reduced pressure, fractional extraction, chromatography purification, and low-temperature crystallization in sequence. The specific operation steps are as follows: The reaction solution was cooled to room temperature and transferred to a nitrogen blower (pressure -0.06 MPa, temperature 40℃) to be concentrated to 1 / 6 of the original volume. Then, the solvent was further removed by vacuum distillation (-0.07 MPa, temperature 50℃) to obtain the concentrated product. Add a mixture of ethyl acetate and purified water in a volume ratio of 1:1 to the concentrated product, place it in a separatory funnel and shake vigorously for 5 min, then perform ultrasonic-assisted separation (power 200 W, duration 5 min), collect the organic phase; repeat the extraction once, combine the organic phases, and concentrate again with nitrogen blowing until no solvent residue remains to obtain the crude product. The crude product was dissolved in a mixture of dichloromethane and methanol in a volume ratio of 5:1 to prepare a sample solution with a concentration of 5 mg / mL. A chromatography column packed with 300-mesh chromatographic grade silica gel powder was used for gradient elution with the same eluent. The eluent of the target component was collected by a UV detector (detection wavelength 254 nm) and concentrated to dryness by nitrogen blowing to obtain the purified intermediate. The purified intermediate was redispersed in a 1:3 volume ratio of ethanol and purified water mixture, with a solid content of 5 mg / mL. The mixture was then placed in an ultrasonic cleaner (50 W, 5 min) to promote uniform dispersion. Subsequently, it was transferred to a 0°C cryogenic incubator and allowed to stand for 12 h to slowly precipitate crystals. The crystals were then filtered using a single layer of rapid filter paper (under reduced pressure of -0.07 MPa). During filtration, the crystals were repeatedly rinsed twice with a 1:5 volume ratio of ethanol and purified water mixture to remove surface impurities. The crystals were then placed in a freeze-drying oven, pre-frozen at -25°C for 3 h, then cooled to -50°C, maintaining a vacuum of ≤10 Pa, and freeze-dried for 24 h to obtain the DMFC-based benzaldehyde molecular gyroscope, with a yield of 313.5 g and a yield rate of 90.5%.

[0062] The high-resolution mass spectrometry results and nuclear magnetic resonance spectra of the DMFC molecular gyroscope prepared in this embodiment are consistent with those obtained in Example 1.

[0063] Example 3

[0064] 230.22 g (1 mol) of the natural product amycin was added to a mixture of ethanol and tetrahydrofuran (volume ratio 6:1), and stirred continuously at 50 °C at a stirring speed of 1200 rpm. Dynamic ultrasonic treatment (power 400 W, frequency 40 kHz) was applied simultaneously. The stirring-ultrasound synergistic effect lasted for 0.3 h to obtain a 3 M amycin solution. 670.90 g (5 mol) of 3,5-dimethylbenzaldehyde was added to a mixture of ethanol and N,N-dimethylformamide. The mixture was stirred at room temperature at a speed of 1800 rpm, accompanied by intermittent ultrasonic assistance (400 W power, 10 min of ultrasonication every 30 min of stirring) for 0.2 h to obtain a 6 M 3,5-dimethylbenzaldehyde solution. 202.38 g (2 mol) of artificial organic base triethylamine and 727.08 g (6 mol) of natural organic base choline (molar ratio of artificial organic base to natural organic base 1:3) were mixed and stirred continuously at room temperature for 0.5 h to obtain a homogeneous organic base solution. The above-mentioned organic base solution was added to the amycin solution by spraying at a rate of 10 mL / min. After spraying, the solution was placed in a constant temperature shaker (temperature 25℃, speed 2000 rpm) and continuously shaken for 0.5 h to achieve pre-activation of amycin. During the shaking period, short-term ultrasound (power 100 W, duration 20 min) was applied every 30 min. While maintaining a constant shaking speed of 2000 rpm, 3,5-dimethylbenzaldehyde solution was added dropwise to the above mixture at a rate of 15 mL / min using a constant flow pump. During the dropwise addition, a gradient temperature program was started, with the temperature increase rate controlled at 5℃ / min, gradually increasing to the target temperature of 100℃. During the reaction, the shaking was maintained at 2000 rpm, and ultrasonic assistance was continuously provided (power 400 W, intermittent: 10 min of ultrasonication followed by 5 min of rest). After 2 h of reaction, the reaction solution containing the daminovic benzaldehyde molecular gyroscope was obtained by monitoring the reaction solution until the starting material spot disappeared using thin-layer chromatography (TLC).

[0065] After the reaction was completed, the resulting reaction solution was subjected to nitrogen blowing under reduced pressure, fractional extraction, chromatography purification, and low-temperature crystallization in sequence. The specific operation steps are as follows: The reaction solution was cooled to room temperature and transferred to a nitrogen blower (pressure -0.08 MPa, temperature 40℃) to be concentrated to 1 / 6 of the original volume. Then, the solvent was further removed by vacuum distillation (-0.09 MPa, temperature 50℃) to obtain the concentrated product. Add a mixture of ethyl acetate and purified water in a volume ratio of 8:1 to the concentrated product, place it in a separatory funnel and shake vigorously for 10 min, then perform ultrasonic-assisted separation (power 200 W, duration 20 min), collect the organic phase; repeat the extraction 3 times, combine the organic phases, and concentrate again with nitrogen blowing until no solvent residue remains to obtain the crude product. The crude product was dissolved in a mixture of dichloromethane and methanol in a volume ratio of 30:1 to prepare a sample solution with a concentration of 10 mg / mL. A chromatography column packed with 600-mesh chromatographic grade silica gel powder was used for gradient elution with the same eluent. The eluent of the target component was collected by a UV detector (detection wavelength 254 nm) and concentrated to dryness by nitrogen blowing to obtain the purified intermediate. The purified intermediate was redispersed in a 1:12 volume ratio of ethanol and purified water, with a solid content of 30 mg / mL. The mixture was then placed in an ultrasonic cleaner (200 W, 20 min) to promote uniform dispersion. Subsequently, it was transferred to a cryogenic incubator at 8°C and allowed to stand for 2 h to slowly precipitate crystals. The crystals were then filtered using three layers of rapid filter paper (under reduced pressure of -0.09 MPa). During filtration, the crystals were repeatedly washed four times with a 1:20 volume ratio of ethanol and purified water to remove surface impurities. The crystals were then placed in a freeze-drying oven, pre-frozen at -5°C for 1 h, then cooled to -15°C, maintaining a vacuum of ≤10 Pa, and freeze-dried for 12 h to obtain the DMFC-based benzaldehyde molecular gyroscope. The yield was 317.98, with a yield of 91.8%.

[0066] The high-resolution mass spectrometry results and nuclear magnetic resonance spectra of the DMFC molecular gyroscope prepared in this embodiment are consistent with those obtained in Example 1.

[0067] Performance testing

[0068] The DMFC, a benzaldehyde-based molecular gyroscope prepared in Example 1, was subjected to various spectroscopic tests, including: physical micro-region viscosity sensitivity test, pH stability test, photostability test, Stokes displacement test, and detection limit test.

[0069] 1. Viscosity sensitivity test of the DMFC (dimethicone benzaldehyde-based molecular gyroscope) prepared in Example 1: By adjusting the volume ratio of glycerol to purified water, a series of test solutions with viscosities ranging from 1.0 cP to 956.0 cP were constructed. The specific correspondences are as follows: 0% glycerol (purified water) resulted in a viscosity of 1.00 cP, 10% in 1.74 cP, 30% in 3.72 cP, 50% in 10.72 cP, 70% in 58.89 cP, and 99% in 956.00 cP. A DMFC (dimethylammonium dimethyl phosphonate gyroscope) was added to each solution at a concentration of 10 µM. Spectroscopic measurements were conducted at room temperature using 350 nm as the external excitation wavelength. The spectra are shown below. Figure 4 As shown.

[0070] Test results show that the light signal intensity of DMFC increases significantly with the increase of solution viscosity: the light signal intensity continues to rise in the full viscosity range from 1.0 cP to 956.0 cP; when the volume percentage of glycerol exceeds 50% (corresponding to a viscosity of 10.72 cP), the light signal intensity enters a stage of rapid increase, reaching a peak in the system with a volume percentage of glycerol of 99% (viscosity of 956.00 cP). Compared with the purified water system (0% glycerol), the light signal intensity is increased by about 135 times, which intuitively demonstrates its strong response capability to high viscosity systems.

[0071] To further quantify the relationship between DMFC and viscosity, the solution viscosity and corresponding fluorescence intensity in the range of 1.00 cP to 956.00 cP were converted to logarithmic form (the logarithm of viscosity, logη, were 0.01, 0.24, 0.57, 1.03, 1.77, and 2.99, respectively; the logarithm of fluorescence intensity, logI, were 1.71, 1.90, 2.12, 2.52, 3.03, and 3.62, respectively). A straight line conforming to the Förster-Hoffmann relation was obtained through fitting, and the linear fitting results are shown below. Figure 5 As shown in the figure. The fitting results show that the viscosity sensitivity coefficient of DMFC is as high as 0.72, and the coefficient of determination is 0.98, which means that there is a very strong linear correlation between its optical signal intensity and the viscosity of the fluid micro-region, and it has ultra-high sensitivity to viscosity changes.

[0072] The core advantage of DMFC lies in its precise ability to capture micro-variables in viscosity: whether it's subtle changes in the low viscosity range (e.g., 1.00 cP to 10.72 cP) or significant fluctuations in the high viscosity range (e.g., 10.72 cP to 956.00 cP), it can achieve rapid identification and quantitative judgment through differentiated feedback of light signal intensity. The monitoring effect is accurate, intuitive, and lag-free. This characteristic makes it show great application potential in the coconut oil formulation process—the viscosity changes of coconut oil are directly related to its processing fluidity, quality stability, and final user experience. DMFC can serve as an in-situ visualization molecular tool to sense micro-visibility fluctuations in coconut oil formulation in real time. It can provide efficient data support for process optimization without complex operations, helping to achieve precise formulation and quality control of coconut oil products, and providing innovative solutions for efficient production in the coconut oil processing industry.

[0073] 2. pH stability test of the DMFC (dimethicone benzaldehyde-based molecular gyroscope) prepared in Example 1: 1.04 mg of the DMFC (dimethylammonium methyl ... Figure 6 As shown in the figure. The test results show that within a wide pH range of 3.0 to 9.0, the fluorescence intensity of DMFC remains weak and stable, without significant increase or decrease or abnormal fluctuation in light signal due to pH fluctuations. This fully demonstrates its excellent pH tolerance, and that its light signal release performance is not easily affected by environmental pH. It can maintain a stable response in various environments, including slightly acidic, neutral, and slightly alkaline environments, and has extremely strong environmental adaptability.

[0074] DMFC's wide pH tolerance allows it to maintain stable monitoring performance in complex acidic and alkaline environments. This advantage is of great practical value in coconut oil formulation: coconut oil itself may exhibit weakly acidic to neutral properties depending on the raw material variety and processing technology, and the emulsifiers, antioxidants, and other excipients added during formulation may cause slight pH fluctuations in the system. DMFC, however, can accurately capture micro-viscosity changes in coconut oil in such complex environments without the need for additional pH adjustment, effectively avoiding the impact of pH interference on monitoring results. Its excellent environmental tolerance makes it suitable for diverse process scenarios in coconut oil formulation, with great application potential, providing reliable molecular tool support for the stable formulation and quality control of coconut oil products.

[0075] 3. Photostability test of the DMFC (dimethicone benzaldehyde-based molecular gyroscope) prepared in Example 1: 1.39 mg of the DMFC (dimethylaminobenzaldehyde-based molecular gyroscope) prepared in Example 1 was dissolved in ethyl acetate to prepare a 4 mM stock solution. This stock solution was then added to low-viscosity purified water (viscosity 1.0 cP) and high-viscosity 90% (v / v) glycerol solution (viscosity 956.0 cP), respectively, controlling the final concentration of DMFC in the system to 10 µM. The changes in light signal intensity were monitored over 60 minutes under continuous irradiation from a 350 nm external excitation source. The monitoring results are as follows: Figure 7 As shown, in purified water, the initial fluorescence intensity of DMFC was 43.1 au, which decreased to 42.6 au after 10 minutes, 42.3 au after 20 minutes, 41.8 au after 30 minutes, and 40.6 au after 60 minutes, with minimal intensity fluctuation throughout. In glycerol solution, the initial fluorescence intensity reached 5942.07 au, which decreased to 5914.19 au after 10 minutes, 5897.6 au after 20 minutes, 5895.2 au after 30 minutes, and 5890.3 au after 60 minutes, also remaining stable.

[0076] DMFC exhibits excellent photostability. Whether in low-viscosity purified water or high-viscosity glycerol systems, its fluorescence intensity did not significantly decrease after 60 minutes of continuous excitation, demonstrating excellent durability. This stability allows it to maintain strong luminescence performance even during long-term continuous irradiation, is not easily affected by external light environments, and maintains a consistently stable and reliable signal output. This advantage is highly valuable in coconut oil industrial production—process monitoring in coconut oil processing often requires long-term continuous monitoring. DMFC can maintain a stable light signal response throughout the entire monitoring process, accurately capturing viscosity changes at each stage of coconut oil production without frequent replacement or calibration, effectively improving monitoring efficiency and data accuracy. Its excellent photostability makes it suitable for continuous production scenarios in the coconut oil industry, with enormous application potential, providing a reliable molecular monitoring tool for the large-scale, high-quality production of coconut oil products.

[0077] 4. Stokes displacement test of the DMFC (Dentamicin Benzaldehyde-based Molecular Gyroscope) prepared in Example 1: 1.73 mg of the DMFC (dimethylaminobenzaldehyde-based molecular gyroscope) prepared in Example 1 was dissolved in ethyl acetate to prepare a 5 mM stock solution. This stock solution was then added to purified water to control the final concentration of DMFC in the system to 10 μM. Its absorption and emission spectra were tested at room temperature. The test results are as follows: Figure 8 As shown, DMFC exhibits a Stokes displacement of up to 136.8 nm in all tested solvents, demonstrating a significant advantage in large displacement.

[0078] The large Stokes shift characteristic of DMFC fundamentally solves the problem of interference between excitation and emission light—the wide wavelength interval completely separates the excitation and emission light, effectively avoiding signal superposition interference of the excitation light, significantly improving the signal-to-noise ratio of monitoring, and making the optical signal response more accurate and the data more reliable. Its insensitivity to solvent polarity further enhances its environmental adaptability. Even in the industrial formulation of coconut oil, facing the complex system composed of coconut oil itself and possibly added emulsifiers, antioxidants, and other polar components, DMFC can still maintain stable light absorption performance and signal output. This combination of advantages makes it highly practical for continuous monitoring in coconut oil production, accurately capturing micro-region viscosity changes in coconut oil, providing efficient and reliable data support for process optimization and quality control, and demonstrating great application potential.

[0079] 5. The detection limit of the DMFC (dimethicone-based benzaldehyde-based molecular gyroscope) prepared in Example 1: 2.08 mg of the DMFC (dimethylaminobenzaldehyde-based molecular gyroscope) prepared in Example 1 was dissolved in linoleic acid to prepare a stock solution with a concentration of 6 mmol / L. For testing, this stock solution was diluted to 10 μmol / L and then added to a water and glycerol mixture with extremely low viscosity. The detection sensitivity to the viscosity of the fluid micro-region was tested at room temperature, and a linear fitting plot of the detection limit of DMFC was obtained, as shown below. Figure 9 As shown in the figure. The test results show that in industrial oil fluid systems with low gelation degree, the viscosity value of DMFC exhibits an excellent linear relationship with the logarithm of the light signal emission intensity, with a fitting determination coefficient as high as 0.95. Based on this, its detection limit is calculated to be as low as 1.034 cP.

[0080] DMFC's ultra-wide detection limit gives it exceptional micro-viscosity sensing capabilities, enabling it to keenly detect extremely subtle viscosity fluctuations in the microenvironment of fluids, providing precise and sensitive monitoring performance. This characteristic is highly valuable in coconut oil production—during the coconut oil formulation process, from raw material processing to finished product molding, small but critical fluctuations in micro-viscosity may occur. These subtle changes directly affect the product's flowability, stability, and final quality. With a low detection limit of 1.034 cP, DMFC can accurately capture these minute viscosity changes, providing reliable data support for real-time control of coconut oil production processes and refined quality management. Its superior detection sensitivity makes it perfectly suited to the monitoring needs of the coconut oil industry, with enormous application potential, providing key technological assurance for the high-quality and standardized production of coconut oil products.

[0081] Application Example 1

[0082] 2.42 mg of the DMFC (dimethylaminobenzaldehyde-based molecular gyroscope) prepared in Example 1 was dissolved in ethanol to prepare a stock solution with a concentration of 7 mmol / L. This stock solution was then added to three commercially available coconut oil products: Nutiva, Viva Naturals, and Kaxiangnian, respectively, controlling the final concentration of DMFC in all systems to be 10 µmol / L. Emission spectra were measured at room temperature using a 350 nm external excitation source. The results are as follows: Figure 10 As shown in the figure, the test results show that DMFC exhibits significant differences in optical signal response to commercially available coconut oil systems of different viscosities: the optical signal intensity of Nutiva coconut oil with a viscosity of 62 cP is 724.4 au, the optical signal intensity of Viva Naturals coconut oil with a viscosity of 75 cP increases to 831.7 au, and the optical signal intensity of Kaxiangnian coconut oil with a viscosity of 88 cP further increases to 955.0 au. The optical signal intensity and coconut oil viscosity are consistently and strictly positively correlated. Meanwhile, the peak emission wavelength of DMFC remains stable at 481 nm, exhibiting bright green light, providing a clear and intuitive visualization effect, and possessing the core technological advantages of in-situ measurement without damaging the sample.

[0083] The precise response characteristics of DMFCs make them irreplaceable in the coconut oil industry, demonstrating immense application value and potential. Commercially available coconut oil products often exhibit viscosity differences ranging from 62 cP to 88 cP due to variations in raw material origin, processing technology (cold pressing / refining), and purity grade (e.g., products from mainstream brands like Nutiva, Viva Naturals, and Kaxiangnian). DMFCs, however, require no complex sample pretreatment and can be directly embedded in the coconut oil system in situ, rapidly achieving viscosity grading and quality assessment through the quantification of differences in light signal intensity. Their bright green light emission characteristics reduce reliance on high-end testing equipment, making real-time monitoring on-site more convenient and efficient. The in-situ measurement mode completely preserves the original quality of the coconut oil, avoiding the damage to samples caused by traditional testing methods and ensuring data accuracy and reliability. This molecular tool is perfectly suited for the entire process of the coconut oil industry, including raw material selection, viscosity monitoring during production, and finished product quality grading, providing innovative technical support for standardized production, quality traceability, and process optimization of coconut oil products, with broad application prospects.

[0084] In summary, the DMFC (dimethylbenzaldehyde-based molecular gyroscope) and its preparation method and application provided by this invention are constructed from the natural product dimethylbenzaldehyde and 3,5-dimethylbenzaldehyde via a one-step conjugated coupling reaction. The preparation process is green and environmentally friendly, simple to operate, and uses only milligram-level quantities, resulting in low preparation and application costs. It possesses the core conditions for large-scale industrial production and promotion. Furthermore, due to its conjugated single and double bond internal rotation structure, it can exhibit differentiated rotational states in fluid systems with varying micro-region viscosities, converting viscosity differences into visible 481nm cyan-blue light. This technology utilizes optical signals to achieve rapid, efficient, and visualized in-situ detection of viscosity in fluid systems. It is particularly effective for commercially available coconut oil products containing a large amount of pseudoplastic components, eliminating the need for external interventions such as mechanical shearing and effectively avoiding detection distortion caused by shear thinning. The intensity of the optical signal precisely reflects the gelation degree and viscosity grade of the coconut oil. Further performance tests confirm its excellent compatibility with coconut oil systems—a micro-area viscosity sensitivity coefficient as high as 0.75 and a detection limit as low as 1.034 cP, enabling it to keenly capture micro-area viscosity fluctuations during coconut oil production and storage, and maintaining a high pH level. With stable optical signal output and excellent photostability within a wide range of 3.0 to 9.0, and good tolerance to solvents of different polarities, it can meet the needs of long-term continuous monitoring and detection of complex component systems in the coconut oil industry. These advantages enable it to perform efficiently in all processes, including coconut oil raw material screening, real-time control of the production process, finished product quality grading and quality traceability. It significantly reduces the dependence on high-end testing equipment, improves the efficiency and quality control of coconut oil production, and provides innovative molecular tool support for the standardization and refinement of the coconut oil industry. It demonstrates irreplaceable application value and huge potential in the coconut oil industry.

[0085] The above description is only a preferred embodiment of the present invention. It should be noted that for those skilled in the art, several improvements and modifications can be made without departing from the principle of the present invention, and these improvements and modifications should also be considered within the scope of protection of the present invention.

Claims

1. A molar amylin benzaldehyde-based molecular gyroscope, characterized in that, The structure of the dental amycin benzaldehyde-based molecular gyroscope is shown below: 。 2. The preparation method of the dental amycin benzaldehyde-based molecular gyroscope according to claim 1, characterized in that, Includes the following steps: (1) The organic base solution was added to the amycin solution and mixed to obtain a pre-activated system; (2) The pre-activated system and 3,5-dimethylbenzaldehyde solution were mixed and coupled together to obtain the damizobenzaldehyde-based molecular gyroscope.

3. The preparation method of the dinoflagellate benzaldehyde-based molecular gyroscope as described in claim 2, characterized in that, In step (1), the concentration of the amycin solution is 1~3M; Amifentanil solution contains amifentanil, alcohol solvents, and organic solvents; The alcohol solvent is one or more of methanol, ethanol, ethylene glycol, propanol and 1,2-propanediol; The organic solvent is one or more of acetonitrile, tetrahydrofuran, acetone, N,N-dimethylformamide, ethyl acetate, and dimethyl sulfoxide; The volume ratio of alcohol solvents to organic solvents is 1 to 6:

1.

4. The preparation method of the dinoflagellate benzaldehyde-based molecular gyroscope as described in claim 3, characterized in that, The organic base solution in step (1) contains artificial organic bases, natural organic bases, and solvents; The artificial organic base is one or more of triethylamine, 4-dimethylaminopyridine, N,N-diisopropylethylamine, pyridine, 4-diethylaminopyridine and N,N,N',N'-tetramethylethylenediamine; Natural organic bases are one or more of choline, betaine, and acetylcholine; The solvent is one or more of ethanol, methanol, propylene glycol, ethylene glycol, tetrahydrofuran, dioxane, N,N-dimethylformamide and ethyl acetate; The molar ratio of artificial organic bases to natural organic bases is 1:1~3; The molar ratio of artificial organic base to guanylic acid is 0.5~2:

1.

5. The preparation method of the dinoflagellate benzaldehyde-based molecular gyroscope as described in claim 4, characterized in that, In step (1), the additive is a spray additive; the spray rate of the spray additive is 5~10mL / min; In step (1), the mixing temperature is 20~30℃, the rotation speed is 1200~2000rpm, and the time is 0.5~1.5h; The mixture is subjected to ultrasound simultaneously, with an ultrasound power of 100~400W and a single session duration of 5~20min; the interval between two adjacent ultrasound sessions is 25~35min.

6. The preparation method of the dinoflagellate benzaldehyde-based molecular gyroscope as described in claim 5, characterized in that, In step (2), the solvent for the 3,5-dimethylbenzaldehyde solution is one or more of ethanol, methanol, propylene glycol, ethylene glycol, tetrahydrofuran, dioxane, N,N-dimethylformamide, and ethyl acetate. The concentration of 3,5-dimethylbenzaldehyde solution is 1~6M.

7. The preparation method of the dinoflagellate benzaldehyde-based molecular gyroscope as described in claim 6, characterized in that, The molar ratio of 3,5-dimethylbenzaldehyde to amyxin is 1~5:

1.

8. The preparation method of the dinoflagellate benzaldehyde-based molecular gyroscope as described in claim 7, characterized in that, The mixing drop rate in step (2) is 5~15 mL / min; In step (2), the target reaction temperature for the coupling condensation reaction is 60~100℃, the heating rate is 1~5℃ / min, the ultrasonic power is 250~400W, the time for a single ultrasonic treatment is 5~15min, and the interval between two ultrasonic treatments is 3~8min. The coupling condensation reaction takes 2 to 24 hours.

9. The application of the acetamiprid benzaldehyde-based molecular gyroscope of claim 1 in the physical micro-area viscosity measurement of industrial vegetable oils.

10. A method for measuring the physical micro-area viscosity of industrial vegetable oils, characterized in that, Includes the following steps: The benzaldehyde-based molecular gyroscope, solvent, and test sample of the damicin were mixed, and fluorescence excitation was performed to complete the determination. The ratio of the amount of the acetamiprid benzaldehyde-based molecular gyroscope, solvent, and test sample is 1~100 μmol: 1 L: 0.003 L; The solvent is one or more of ethyl acetate, apple ester, and triacetyl ester; The excitation wavelength for fluorescence excitation is 300~400nm.

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