Visual fatty aldehyde adsorbing material as well as preparation method and application thereof

Abstract

The invention discloses a visual fatty aldehyde adsorption material as well as a preparation method and application thereof, develops a monoquinone column [5] arene macrocyclic compound, and successfully applies the monoquinone column [5] arene macrocyclic compound to adsorption and capture of fatty aldehyde. The negative electron macrocyclic cavity of the monoquinone column [5] arene macrocyclic compound provided by the invention can capture fatty aldehyde molecules and form a host-guest complex with the stoichiometric ratio of 1: 1. The capture is accompanied with the obvious color change of the monoquinone column [5] arene macrocyclic compound from red to dark brown, and an intuitive and easy-to-monitor visual means is provided for the adsorption process of fatty aldehyde steam. The interaction force between the material and fatty aldehyde molecules is relatively strong, so that the fatty aldehyde molecules can be well stored without leakage. The method has the characteristics of low energy consumption and simplicity and convenience in operation, and conforms to the green chemistry concept. Meanwhile, the compound also realizes visual monitoring of the fatty aldehyde adsorption process, and a novel, energy-saving and environment-friendly technical scheme is provided for capture of fatty aldehyde.

Description

Technical Field

[0001] The present invention relates to the technical field of fatty aldehyde adsorbents, and more specifically, to a fatty aldehyde visual adsorption material and a preparation method and application thereof. Background Art

[0002] Fatty aldehydes are an important class of organic compounds that can be widely used in the production of dyes, spices, preservatives and organic solvents. The main sources of fatty aldehydes are organic synthesis, incomplete combustion of fuels and photochemical reactions of hydrocarbons in the atmosphere under sunlight. Long-term exposure to these vapors is harmful to human health, especially affecting the respiratory system and increasing the risk of cancer. Therefore, the detection of fatty aldehydes is crucial to human health and environmental protection. Catalytic oxidation and adsorption are common methods for removing fatty aldehydes from the air. Although fatty aldehydes can be efficiently oxidized to fatty acids by catalytic methods, most catalytic materials are loaded with precious metals (such as palladium, platinum, silver and gold), which are expensive. In addition, the adsorption capacity of some traditional adsorbents is quite limited. For example, activated carbon is not effective in removing fatty aldehydes, and metal-organic frameworks and zeolites lack target selectivity when removing aliphatic aldehydes. Chinese patent publication number CN117983314A discloses a photocatalyst, photocatalytic device and method for removing formaldehyde. The photocatalyst Pd-MnCeTiO is prepared under specific process parameters and a composition containing elements such as manganese, palladium and titanium. x Under the irradiation of ultraviolet light, the photocatalyst has a photocatalytic formaldehyde removal effect and can maintain a formaldehyde degradation efficiency of more than 90% within 90 minutes; by continuously introducing formaldehyde for 24 hours, the conversion rate is maintained at more than 79%, the formaldehyde removal stability is high, and the reproducibility is good. However, this method has a complex device and uses precious metal elements, which is expensive and has high cost, and the preparation process has high energy consumption. The Chinese patent with publication number CN118999091A discloses a drying device and method for formaldehyde adsorption particles. The device includes a bracket and a drying tank arranged on the bracket. The surface of the drying tank is respectively provided with a feed port and a discharge port with a valve, the surface of the bracket is provided with a controller, the interior of the drying tank is provided with a drying mechanism, and the surface of the bracket is respectively provided with a clamping mechanism and a shaking mechanism. This invention incorporates a drying mechanism that uses a spiral stirring shaft to stir the formaldehyde-absorbing particles within the drying can. Simultaneously, an air outlet mounted on the shaft drives hot air to dry out moisture from the formaldehyde-absorbing particles. Because the air outlet rotates with the shaft, the hot air quickly spreads throughout the drying can, improving drying efficiency. However, this solution is complex and expensive, and it cannot achieve visual adsorption of formaldehyde.

[0003] Therefore, in view of the technical bottlenecks in the adsorption separation technology of fatty aldehydes, such as high energy consumption, complex process, high cost, poor adsorption efficiency and inability to achieve visual adsorption of fatty aldehydes, there is an urgent need to develop a simple, efficient, energy-saving and visual method to monitor and capture fatty aldehydes. Summary of the Invention

[0004] The present invention addresses the technical bottlenecks of high energy consumption, high cost, and poor adsorption efficiency in the adsorption separation technology of fatty aldehydes. It provides a visual adsorption material for fatty aldehydes, its preparation method, and its application. It develops a monoquinone column [5] aromatic macrocyclic compound and successfully applies it to the adsorption and capture of fatty aldehydes. The method has the characteristics of low energy consumption and simple operation, which conforms to the concept of green chemistry. At the same time, the compound also realizes the visual monitoring of the fatty aldehyde adsorption process, providing a novel, energy-saving, and environmentally friendly technical solution for the capture of fatty aldehydes.

[0005] To achieve the above object, the technical solution of the present invention is as follows:

[0006] A visual adsorption material for fatty aldehydes, wherein the visual adsorption material for fatty aldehydes is a monoquinone column [5] aromatic hydrocarbon macrocyclic compound having a structure shown in the following formula:

[0007]

[0008] The present invention also discloses a method for preparing the above-mentioned fatty aldehyde visual adsorption material, comprising the following steps:

[0009] (1) 1,4-dimethoxybenzene and paraformaldehyde are dissolved in 1,2-dichloroethane, and then a boron trifluoride ether solution is added to react at room temperature for 20 to 30 minutes. After the reaction is complete, water is added to quench the reaction, and the liquids are separated by column chromatography to obtain a column [5] aromatic macrocyclic compound;

[0010] (2) dissolving the column [5] aromatic macrocyclic compound in tetrahydrofuran solution, adding an aqueous solution of cerium ammonium nitrate and reacting at 25° C. for 24 hours. After the reaction is completed, washing with water, separating the liquids and concentrating under reduced pressure to obtain a red mixture, which is separated by column chromatography to obtain a monoquinone column [5] aromatic macrocyclic compound 1;

[0011]

[0012] Optionally, step (1) specifically includes: placing 1,4-dimethoxybenzene and paraformaldehyde in a round-bottom flask, adding 1,2-dichloroethane and stirring for 10 to 20 minutes, then adding boron trifluoride ether solution dropwise at room temperature for 20 to 30 minutes until the solution turns dark green, monitoring the reaction completion, adding water to quench the reaction and stirring for 10 to 20 minutes, and then separating the liquids by column chromatography to obtain a column [5] aromatic macrocyclic compound.

[0013] Optionally, in step (1), the molar ratio of the 1,4-dimethoxybenzene, the paraformaldehyde and the boron trifluoride etherate is 1:1:1.

[0014] Optionally, in step (2), the mass volume ratio of the pillar [5] aromatic macrocyclic compound and the aqueous solution of ceric ammonium nitrate is 3:20.

[0015] Optionally, in step (1) and step (2), the eluent used in the column chromatography includes petroleum ether or dichloromethane.

[0016] The present invention also discloses an application of the above-mentioned fatty aldehyde visual adsorption material as a fatty aldehyde adsorbent.

[0017] Optionally, the application method includes: removing the solvent from the monoquinone column [5] aromatic macrocyclic compound by heating to activate it, wherein the activation temperature is 70°C to 80°C and the time is ≥10h; placing the activated monoquinone column [5] aromatic macrocyclic compound in a fatty aldehyde vapor atmosphere with a temperature of less than 80°C until the color of the monoquinone column [5] aromatic macrocyclic compound changes from red to dark brown, thereby achieving adsorption of fatty aldehyde molecules.

[0018] Optionally, the temperature of the fatty aldehyde vapor is 25°C to 35°C.

[0019] Implementing the embodiments of the present invention will have the following beneficial effects:

[0020] (1) The present invention utilizes a monoquinone column [5] aromatic macrocyclic compound to achieve a gaseous color change response to propionaldehyde, butyraldehyde, and valeraldehyde, and has high stability. Compared with existing detection technologies, the present invention has simple operation, low equipment requirements, low energy consumption, energy conservation, and reduces the production cost of detecting aldehyde vapors.

[0021] (2) The synthesis method of monoquinone column[5] aromatic macrocyclic compounds is simple and the preparation process is fast. They can be obtained in large quantities in a short time, which is of great significance for large-scale applications. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] Figure 1 This is the hydrogen nuclear magnetic resonance spectrum of the monoquinone column [5] aromatic macrocyclic compound of Example 1 of the present invention.

[0023] Figure 2 This is the thermogravimetric curve of the monoquinone column [5] aromatic macrocyclic compound of Example 1 of the present invention.

[0024] Figure 3 This is the powder X-ray diffraction pattern of the monoquinone column [5] aromatic macrocyclic compound of Example 1 of the present invention.

[0025] Figure 4 This is the powder X-ray diffraction pattern of the adsorption of propionaldehyde, butyraldehyde and valeraldehyde by the single quinone column [5] aromatic macrocyclic compound of Example 1 of the present invention.

[0026] Figure 5 This is the solid-state UV-visible absorption spectrum of the monoquinone column [5] aromatic macrocyclic compound and the adsorption of propionaldehyde, butyraldehyde and valeraldehyde in Example 1 of the present invention.

[0027] Figure 6 The powder X-ray diffraction pattern of the ground monoquinone column [5] aromatic macrocyclic compound of the present invention for adsorption of propionaldehyde, butyraldehyde and valeraldehyde.

[0028] Figure 7 The solid-state UV-visible absorption spectra of the ground monoquinone column [5] aromatic macrocyclic compound and the adsorption of propionaldehyde, butyraldehyde and valeraldehyde of the present invention are shown. DETAILED DESCRIPTION

[0029] The present invention will be further described below with reference to specific examples, but the present invention is not limited thereto in any way.

[0030] The present invention discloses a visual adsorption material for fatty aldehydes. The visual adsorption material for fatty aldehydes is a monoquinone column [5] aromatic hydrocarbon macrocyclic compound having a structure shown in the following formula:

[0031]

[0032] Specifically, because the fatty aldehyde molecules are electropositive, the electron-negative macrocyclic cavity of the monoquinone column [5] aromatic hydrocarbon macrocyclic compound provided by the present invention can capture the fatty aldehyde molecules and form a host-guest complex with a stoichiometric ratio of 1:1. This capture is accompanied by a significant color change of the monoquinone column [5] aromatic hydrocarbon macrocyclic compound from red to dark brown, providing an intuitive and easy-to-monitor visualization method for the adsorption process of the fatty aldehyde vapor. The material has a strong interaction with the fatty aldehyde molecules and can effectively store the fatty aldehyde molecules without leakage.

[0033] The present invention also discloses a method for preparing the above-mentioned fatty aldehyde visual adsorption material, comprising the following steps:

[0034] (1) 1,4-dimethoxybenzene and paraformaldehyde are dissolved in 1,2-dichloroethane, and then a boron trifluoride ether solution is added to react at room temperature for 20 to 30 minutes. After the reaction is complete, water is added to quench the reaction, and the liquids are separated by column chromatography to obtain a column [5] aromatic macrocyclic compound;

[0035] (2) The column [5] aromatic macrocyclic compound was dissolved in tetrahydrofuran solution, and an aqueous solution of cerium ammonium nitrate was added to react at 25°C for 24 hours. After the reaction was completed, the mixture was washed with water, separated, and concentrated under reduced pressure to obtain a red mixture, which was separated by column chromatography to obtain the monoquinone column [5] aromatic macrocyclic compound 1;

[0036]

[0037] In a specific embodiment, step (1) specifically includes: placing 1,4-dimethoxybenzene and paraformaldehyde in a round-bottom flask, adding 1,2-dichloroethane and stirring for 10 to 20 minutes, then adding boron trifluoride ether solution dropwise at room temperature for 20 to 30 minutes until the solution turns dark green, monitoring the reaction completion, adding water to quench the reaction and stirring for 10 to 20 minutes, separating the liquids and separating by column chromatography to obtain column [5] aromatic macrocyclic compounds.

[0038] In one specific embodiment, in step (1), the molar ratio of 1,4-dimethoxybenzene, paraformaldehyde and boron trifluoride etherate is 1:1:1.

[0039] In a specific embodiment, in step (2), the mass volume ratio of the column [5] aromatic macrocyclic compound and the aqueous solution of ceric ammonium nitrate is 3:20.

[0040] In a specific embodiment, in step (1) and step (2), the eluent used in column chromatography includes petroleum ether or dichloromethane.

[0041] The present invention also discloses an application of the above-mentioned fatty aldehyde visual adsorption material as a fatty aldehyde adsorbent.

[0042] In a specific embodiment, the application method includes: removing the solvent from the monoquinone column [5] aromatic macrocyclic compound by heating, wherein the activation temperature is 70°C to 80°C and the time is ≥10 hours; placing the activated monoquinone column [5] aromatic macrocyclic compound in a fatty aldehyde vapor atmosphere at a temperature of <80°C until the color of the monoquinone column [5] aromatic macrocyclic compound changes from red to dark brown, thereby achieving adsorption of fatty aldehyde molecules.

[0043] In one embodiment, the temperature of the fatty aldehyde vapor is 25°C to 35°C.

[0044] The following are specific embodiments

[0045] Example 1

[0046] Monoquinone column [5] aromatic macrocyclic compounds were prepared by the following method:

[0047]

[0048] The first step of the reaction: 1.38 g of 1,4-dimethoxybenzene was dissolved in 20 mL of 1,2-dichloroethane, and then 0.31 g of paraformaldehyde was added and stirred for 20 minutes until the paraformaldehyde was dispersed. Then, 1.25 mL of boron trifluoride ether was added dropwise to the solution and reacted at room temperature of 25°C for 20 minutes. After the reaction was complete, 200 mL of water was added to quench the reaction, and the mixture was stirred for 30 minutes to completely quench the reaction. After separation, the mixture was dried and separated by column chromatography to obtain the column [5] aromatic compound. The yield of the intermediate product of Example 1 was tested to be 65%.

[0049] Step 2: In a 250 mL round-bottom flask, 3.00 g of column [5] aromatic hydrocarbon was dissolved in 100 mL of tetrahydrofuran and stirred. 2.19 g of an aqueous solution prepared from cerium ammonium nitrate was added dropwise, and the mixture was stirred at room temperature for 24 h. After the reaction was completed, the organic phase was washed with 100 mL of water and 100 mL of saturated NaCl solution, and the liquids were separated and dried over anhydrous Na2SO4. The residue was filtered and evaporated under reduced pressure, and then purified by silica gel column chromatography (eluent: petroleum ether / dichloromethane) to obtain a red solid monoquinone column [5] aromatic hydrocarbon. The red powder was then heated at 80°C in a vacuum drying oven for about 10 h to obtain the activated monoquinone column [5] aromatic hydrocarbon macrocyclic compound 1. The final product yield of Example 1 was tested to be 20%.

[0050] The product characterization data prepared in this example are as follows:

[0051] 1, 1 H NMR (400MHz, CDCl3) δ (ppm): 6.84 (s, 2H), 6.81 (s, 2H), 6.79 (s, 2H), 6.67 (s, 4H), 3.79 (br, 6H), 3.75 (s, 6H), 3.71 (s, 12H), 3.63 (s, 6H), 3.59 (s, 4H). 13 CNMR (100 MHz, CDCl₃, 298 K) δ (ppm): 188.8, 151.2, 150.9, 150.9, 146.7, 133.5, 129.5, 128.5, 128.0, 123.7, 114.4, 114.4, 113.9, 113.9, 56.1, 56.0, 55.9, 55.9, 55.6, 53.4, 29.5, 28.2. High-resolution mass spectrometry m / z: 720.2950, ​​melting range: 148.6-149.9°C.

[0052] 1 The H NMR detection results confirmed the structural correctness of the synthesized monoquinone column[5] aromatic macrocyclic compound.

[0053] ( Figure 1 )

[0054] TG test results show that the obtained monoquinone column [5] aromatic macrocyclic compound has good stability ( Figure 2 ).

[0055] The PXRD results show that the obtained monoquinone column [5] aromatic macrocyclic compound has good crystallinity ( Figure 3 ).

[0056] Example 2

[0057] Adsorption of propionaldehyde, butyraldehyde, and valeraldehyde by the monoquinone column [5] aromatic macrocyclic compound 1 prepared in Example 1: Take three 20mL inoculum bottles and add 1mL of propionaldehyde, butyraldehyde, and valeraldehyde, respectively, and name them 1-C3, 1-C4, and 1-C5. Take 20mg of the monoquinone column [5] aromatic macrocyclic compound prepared in Example 1 and place it in three 5mL open inoculum bottles. The three open 5mL inoculum bottles are placed in three 20mL inoculum bottles. The 20mL inoculum bottles are sealed and placed in a 25℃ water bath for 2 hours. The resulting powder is placed in a 40℃ vacuum oven for 30 minutes.

[0058] The product characterization data prepared in this example are as follows:

[0059] 1-C3, 1 H NMR(600MHz, CDCl3)δ9.78(s,1H),6.84(s,2H),6.81(s,2H),6.79(s,2H),6.67(s,4H),3.79(br, 6H),3.75(s,6H),3.71(s,12H),3.63(s,6H),3.59(s,4H).2.47–2.42(m,2H),1.10(t,J=6Hz,3H).

[0060] 1-C4, 1H NMR (600MHz, CDCl3) δ9.73 (d, J = 6Hz, 1H), 6.84 (s, 2H), 6.81 (s, 2H), 6.79 (s, 2H), 6.67 (s, 4H), 3.79 (br, 6H), 3.75 ( s,6H),3.71(s,12H),3.63(s,6H),3.59(s,4H),2.35(td,J=12,6Hz,2H),1.62(q,J=12Hz,2H),0.94(t,J=6Hz,3H).

[0061] 1-C5, 1 H NMR (600MHz, CDCl3) δ9.72 (t, J = 6Hz, 1H), 6.84 (s, 2H), 6.81 (s, 2H), 6.79 (s, 2H), 6.67 (s, 4H), 3.79 (br, 6H), 3.75 (s, 6H), 3.71 (s,12H),3.63(s,6H),3.59(s,4H),2.35(td,J=12,6Hz,2H),1.56(dt,J=12,6Hz,2H),1.33–1.30(m,2H),0.90(t,J=12Hz,3H).

[0062] 1 H NMR results showed that the monoquinone column [5] adsorbed propionaldehyde, butyraldehyde, and valeraldehyde in a stoichiometric ratio of 1:1.

[0063] The PXRD test results are as follows Figure 4 As shown, compared with the PXRD spectrum of the initially activated monoquinone column [5] aromatic macrocyclic compound, after being placed in the vapor of propionaldehyde, butyraldehyde, and valeraldehyde for a period of time, the PXRD spectrum of the monoquinone column [5] aromatic macrocyclic compound changes, which indicates that its crystal structure has changed, meaning that propionaldehyde, butyraldehyde, and valeraldehyde have been adsorbed into the cavity of the monoquinone column [5] aromatic macrocyclic compound.

[0064] Solid-state UV-visible absorption spectroscopy results are as follows Figure 5 As shown in the figure, the adsorption curve of the monoquinone column [5] aromatic macrocyclic compound after adsorption of propanal, butyraldehyde, and valeraldehyde undergoes a red shift, indicating that the charge transfer interaction between the monoquinone column [5] aromatic macrocyclic compound and the fatty aldehyde molecules has changed. In addition, after about 2 hours of adsorption, the powder changes from red to dark brown, further verifying that the properties of the powder have changed.

[0065] Example 3

[0066] The monoquinone column [5] aromatic macrocyclic compound prepared in Example 1 was ground until the powder turned orange. The ground monoquinone column [5] aromatic macrocyclic compound (1-G) was subjected to adsorption of propanal, butyraldehyde, and valeraldehyde: about 60 mg of the monoquinone column [5] aromatic macrocyclic compound was placed in a mortar and ground until the red powder turned orange. Three 20 mL culture bottles were taken and 1 mL of propanal, butyraldehyde, and valeraldehyde were added respectively. The bottles were named 1-G-C3, 1-G-C4, and 1-G-C5. 20 mg of the above orange powder was placed in three 5 mL open culture bottles. The three open 5 mL culture bottles were placed in three 20 mL culture bottles respectively. The 20 mL culture bottles were sealed and placed in a 25°C water bath for 2 hours. The resulting powder was placed in a 40°C vacuum oven for 30 minutes.

[0067] The product characterization data prepared in this example are as follows:

[0068] 1-G-C3, 1 H NMR(600MHz, CDCl3)δ9.76(s,1H),6.84(s,2H),6.81(s,2H),6.79(s,2H),6.67(s,4H),3.79(br,6 H),3.75(s,6H),3.71(s,12H),3.63(s,6H),3.59(s,4H),2.46–2.37(m,2H),1.08(t,J=12Hz,3H).

[0069] 1-G-C4, 1 H NMR (600MHz, CDCl3) δ9.73(t,J=6Hz,1H),6.84(s,2H),6.81(s,2H),6.79(s,2H),6.67(s,4H),3.79(br,6H),3.75( s,6H),3.71(s,12H),3.63(s,6H),3.59(s,4H),2.35(td,J=12,6Hz,2H),1.63(q,J=12Hz,2H),0.94(t,J=12Hz,3H).

[0070] 1-G-C5, 1H NMR (600MHz, CDCl3) δ9.72 (t, J = 6Hz, 1H), 6.84 (s, 2H), 6.81 (s, 2H), 6.79 (s, 2H), 6.67 (s, 4H), 3.79 (br, 6H), 3.75 (s, 6H), 3.71 (s,12H),3.63(s,6H),3.59(s,4H),2.35(td,J=6,12Hz,2H),1.56(dt,J=6,12Hz,2H),1.33–1.30(m,2H),0.90(t,J=12Hz,3H).

[0071] 1 H NMR results showed that the ground monoquinone column [5] adsorbed propionaldehyde, butyraldehyde, and valeraldehyde in a stoichiometric ratio of 1:1.

[0072] The PXRD test results are as follows Figure 6 As shown, compared with the PXRD spectrum of the monoquinone column [5] aromatic macrocyclic compound after initial grinding, the PXRD spectrum of the monoquinone column [5] aromatic macrocyclic compound changes after being placed in the vapor of propionaldehyde, butyraldehyde and valeraldehyde for a period of time, which indicates that its crystal structure has changed, meaning that propionaldehyde, butyraldehyde and valeraldehyde have been adsorbed into the cavity of the monoquinone column [5] aromatic macrocyclic compound after grinding.

[0073] Solid-state UV-visible absorption spectroscopy results are as follows Figure 7 As shown in the figure, the adsorption curves of the ground monoquinone column [5] aromatic macrocyclic compound after adsorption of propanal, butyraldehyde, and valeraldehyde showed a red shift, indicating that the complexation of the ground monoquinone column [5] aromatic macrocyclic compound with the fatty aldehyde molecules also changed the charge transfer interaction. In addition, after about 2 hours of adsorption, the powder changed from orange to dark brown, further verifying that the properties of the powder had changed.

[0074] The above-described embodiments merely represent several implementation methods of the present invention. While the descriptions are relatively specific and detailed, they should not be construed as limiting the scope of the patent application. It should be noted that a person skilled in the art would be able to make various modifications and improvements without departing from the spirit of the present invention, all of which fall within the scope of protection of the present invention. Therefore, the scope of protection of the patent for this invention shall be determined by the appended claims.

Claims

1. A visual adsorption material for fatty aldehydes, characterized in that: The fatty aldehyde visualization adsorption material is a monoquinone column [5] aromatic hydrocarbon macrocyclic compound having the structure shown in the following formula:

2. A method for preparing the fatty aldehyde visual adsorption material according to claim 1, characterized in that: The following steps are involved: (1) 1,4-dimethoxybenzene and paraformaldehyde are dissolved in 1,2-dichloroethane, and then a boron trifluoride ether solution is added to react at room temperature for 20 to 30 minutes. After the reaction is complete, water is added to quench the reaction, and the liquids are separated by column chromatography to obtain a column [5] aromatic macrocyclic compound; (2) dissolving the column [5] aromatic macrocyclic compound in tetrahydrofuran solution, adding an aqueous solution of cerium ammonium nitrate and reacting at 25° C. for 24 hours. After the reaction is completed, washing with water, separating the liquids and concentrating under reduced pressure to obtain a red mixture, which is separated by column chromatography to obtain a monoquinone column [5] aromatic macrocyclic compound 1; 3. The preparation method according to claim 2, characterized in that The steps of step (1) specifically include: placing 1,4-dimethoxybenzene and polyformaldehyde in a round-bottom flask, adding 1,2-dichloroethane and stirring for 10 minutes to 20 minutes, then adding boron trifluoride ether solution dropwise at room temperature for 20 minutes to 30 minutes until the solution turns dark green, monitoring the reaction completion, adding water to quench the reaction and stirring for 10 minutes to 20 minutes, separating the liquids and separating by column chromatography to obtain a column [5] aromatic macrocyclic compound.

4. The preparation method according to claim 3, characterized in that In step (1), the molar ratio of the 1,4-dimethoxybenzene, the paraformaldehyde and the boron trifluoride etherate is 1:1:

1.

5. The preparation method according to claim 2, characterized in that In step (2), the mass volume ratio of the pillar [5] aromatic macrocyclic compound and the aqueous solution of ceric ammonium nitrate is 3:

20.

6. The preparation method according to claim 2, characterized in that In step (1) and step (2), the eluent used in the column chromatography includes petroleum ether or dichloromethane.

7. Use of the fatty aldehyde visual adsorption material according to claim 1 as a fatty aldehyde adsorbent.

8. The use according to claim 7, characterized in that The method of application includes: The monoquinone column [5] aromatic macrocyclic compound is activated by removing the solvent by heating, wherein the activation temperature is 70° C. to 80° C. and the activation time is ≥10 h; The activated monoquinone column [5] aromatic macrocyclic compound is placed in a fatty aldehyde vapor atmosphere at a temperature of less than 80° C. until the color of the monoquinone column [5] aromatic macrocyclic compound changes from red to dark brown, thereby achieving adsorption of fatty aldehyde molecules.

9. The use according to claim 7, characterized in that The temperature of the fatty aldehyde vapor is 25°C to 35°C.

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