Preparation method of solid-phase catalyst and application of solid-phase catalyst in catalytic synthesis of nitrophenoxy alcohol

Abstract

The invention discloses a preparation method of a solid-phase catalyst and application of the solid-phase catalyst in catalytic synthesis of nitrophenoxy alcohol, the solid-phase catalyst with high reaction activity is obtained by performing surface modification on silicon dioxide, and the solid-phase catalyst has high reaction activity and selectivity when being used for transesterification catalytic nitrophenoxy alcohol reaction; besides, when the catalyst is used for synthesizing nitrophenoxy alcohol, the solid-phase catalyst is filled in a fixed bed, and nitrophenol and carbonic ester serving as raw materials flow through the fixed bed reactor filled with the catalyst to react, so that a reaction solvent is not needed, the reaction selectivity is good, and almost no side reaction occurs; pure nitrophenoxy compounds can be obtained only by removing unreacted raw materials and byproducts, and the method has the advantages of milder reaction conditions, convenience and rapidness in separation, suitability for industrial continuous production and the like, and has remarkable industrial potential.

Description

Technical Field

[0001] This invention relates to the field of catalytic synthesis technology, specifically to a method for preparing solid-phase catalysts and their application in the catalytic synthesis of nitrophenoxy alcohols. Background Technology

[0002] Nitrophenoxy alcohols are an important class of chemical raw materials. These substances are widely used in many fields such as pigments, dyes, pharmaceuticals, pesticides, aluminum capacitors, and ionic liquids, and have broad market prospects.

[0003] For example, patent document CN1760170A reports a method for preparing p-nitrophenoxyethanol, which uses o-nitrophenol and ethylene oxide as main raw materials. An addition reaction is carried out under the action of an alkaline catalyst to obtain a crude product, which is then subjected to post-processing such as crystallization, separation, and drying to obtain p-nitrophenoxyethanol. This synthesis method requires high temperature and high pressure, resulting in significant energy consumption and certain safety risks. Furthermore, the ethylene oxide used in this method is a highly toxic, flammable, and explosive substance, requiring strict control over storage, transportation, and use, making it difficult to apply in conventional production.

[0004] Patent document CN106397212A uses ethylene glycol and 2,4-dinitrochlorobenzene as the main raw materials to prepare 2,4-dinitrophenoxyethanol under inorganic base catalysis. This method is simple, but the amount of inorganic bases used as catalysts, such as sodium hydroxide and sodium bicarbonate, is large and difficult to separate and recover, posing problems for recycling. The wastewater generated during the process is also difficult to treat, increasing production costs and environmental pressure.

[0005] Reports indicate that p-nitrophenoxyethanol can be prepared using o-nitrophenol and chloroethanol as raw materials under alkaline catalyst catalysis. However, chloroethanol is a highly toxic substance and is subject to control by public security departments. Furthermore, byproducts such as chlorine are difficult to completely remove, limiting its application and making it difficult to meet actual production requirements.

[0006] As can be seen from the above literature and reports, existing methods for preparing nitrophenoxy alcohols are difficult to simultaneously achieve both product purity and yield. Some methods require high-temperature reactions or solvent purification, which leads to high energy consumption and significant pressure on waste treatment. These methods are not very competitive when applied to industrial production. Therefore, it is necessary to develop a method for preparing nitrophenoxy alcohols that can obtain high-purity and high-yield nitrophenoxy alcohols with lower energy consumption and fewer purification steps, making it suitable for continuous industrial production. Summary of the Invention

[0007] This invention provides a solid-phase catalyst for catalyzing transesterification reactions to prepare nitrophenoxy alcohols, enabling efficient preparation of nitrophenoxy alcohols with lower energy consumption and reducing purification steps, thus making it suitable for industrial continuous production.

[0008] In view of this, the solution of the present invention is as follows: The first aspect of the present invention is to provide a method for preparing a solid-phase catalyst, comprising the steps of: Add silica particles to an alkaline alcohol-water mixed solvent system, add an organoamine silane coupling agent under a protective atmosphere, and then react fully with stirring at 15~40℃. The reaction product was desolventized and filtered to obtain a solid. The solid was then washed and dried to obtain a solid-phase catalyst.

[0009] Furthermore, in the above preparation method: In the alcohol-water mixed solvent system, the volume ratio of water is 30-70%. And / or, the alcohol is selected from methanol, ethanol, isobutanol, and ethylene glycol; And / or, the particle size of the silica particles is 100~1000 mesh; And / or, the reaction process is carried out under a protective gas.

[0010] Furthermore, the organoamine silane coupling agent is selected from at least one of 3-aminopropyltrimethoxysilane, 3-aminoethyltrimethoxysilane, 3-aminomethyltrimethoxysilane, N,N-dimethylamino-3-aminopropyltriethylsilane, N,N-diethylamino-3-aminopropyltriethoxysilane, N-pyrrole-3-aminopropyltriethoxysilane, N-morpholino-3-aminopropyltriethoxysilane, and N-(2-methylimidazolium)-3-aminopropyltriethoxysilane.

[0011] Furthermore, the drying process temperature is 100~180℃; And / or, the filtration, washing, and drying processes are carried out under a protective gas.

[0012] A second aspect of the present invention is to provide a solid-phase catalyst prepared by the method described in the first aspect.

[0013] A third aspect of the invention is to provide the application of the solid-phase catalyst described in the second aspect in the preparation of nitrophenoxy alcohol, wherein nitrophenoxy alcohol is obtained by catalyzing the transesterification reaction of nitrophenol with carbonate.

[0014] A fourth aspect of the present invention is to provide a method for preparing nitrophenoxy alcohol, comprising: A solid catalyst is packed into the reactor to form a catalyst packing layer; Nitrophenol and carbonate are reacted by flowing through a catalyst-filled layer to obtain the reaction product; The reaction product was purified to obtain nitrophenoxy alcohol; The solid-phase catalyst is the solid-phase catalyst described in the second aspect, or is prepared by the preparation method described in the first aspect.

[0015] Furthermore, in the above preparation method: The nitrophenol is selected from o-nitrophenol, m-nitrophenol, o-nitrophenol, nitrocatechol, or nitroresorcinol; And / or, the carbonate is selected from ethylene carbonate, propylene carbonate or glycerol carbonate; And / or, the molar ratio of the nitrophenol to the carbonate is 1:(1~3).

[0016] Furthermore, the temperature of the catalyst filling layer is 100~200℃.

[0017] Furthermore, the reactor is a fixed-bed reactor, and the catalyst is filled into the bed to form a catalyst packing layer.

[0018] Compared with the prior art, the present invention has the following beneficial effects: The method for preparing the solid-phase catalyst described in this invention involves surface modification of silica to obtain a solid-phase catalyst with high reactivity. This catalyst exhibits high reactivity in the transesterification catalysis of nitrophenoxy alcohols and is of great significance for promoting the low-energy consumption, continuous and efficient industrial production of nitrophenoxy alcohols.

[0019] The method for preparing nitrophenoxy alcohols provided by this invention uses a fixed-bed packed reactor with a highly selective solid-phase catalyst. The reaction is carried out by passing nitrophenol and carbonate feedstocks through a catalyst-packed fixed-bed reactor. This reaction exhibits high selectivity and almost no side reactions; therefore, only unreacted feedstocks and byproducts need to be removed to obtain pure nitrophenoxy compounds. Compared to existing synthesis methods, this method offers milder reaction conditions, eliminates the need for reaction solvents, and allows for convenient and rapid product separation. It is suitable for continuous industrial production and possesses significant industrial potential. Attached Figure Description

[0020] Figure 1 The results are obtained by HPLC detection of o-nitrophenoxyethoxyethanol in the reaction solution described in Example 1 of this invention.

[0021] Figure 2 The result of HPLC analysis of o-nitrophenoxyethoxyethanol after washing the reaction solution described in Example 1 of this invention with alkaline water.

[0022] Figure 3 The results are obtained by HPLC analysis of o-nitrophenoxyethoxyethanol after the reaction solution described in Example 1 of this invention was washed with alkaline water and then simply distilled.

[0023] Figure 4 The product described in Embodiment 1 of the present invention 1 H-NMR characterization results.

[0024] Figure 5 The product described in Embodiment 1 of the present invention 13 C-NMR characterization results. Detailed Implementation

[0025] The technical solution of the present invention will now be clearly and completely described in conjunction with preferred embodiments. Obviously, the described embodiments are only a part of the embodiments of the present invention, and not all of them. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0026] In one embodiment, a method for preparing a fixed-bed reactor catalyst suitable for the synthesis of nitrophenoxy alcohols is provided, comprising the following steps: (1) Add an appropriate amount of mixed solvent to the reactor in advance to disperse the solid material, and then add an appropriate amount of alkali (potassium hydroxide, sodium hydroxide, etc.) to adjust the pH to 11~12; (2) Add silica particles to the solution, and then add organic amine silane coupling agent to the solution under inert gas protection and stir for 24 hours. The reaction temperature is 15~40℃. (3) The modified silica system is distilled under negative pressure to remove the solvent and dry the solid at a temperature of 100~180℃.

[0027] (4) The modified silica was washed with pure water and ethanol under inert gas protection. After washing, it was filtered to obtain modified silica, which was then dried under negative pressure at 100~180℃ to obtain the catalyst product.

[0028] In the above embodiments, amine modification can be achieved by modifying the surface of silica with an organic amine silane coupling agent. The solid catalyst has the surface modification structure shown in the following schematic diagram:

[0029] In the above structure, R1 and R2 can be one or more of the following: hydrogen atom, chain alkane, cyclic alkane, aliphatic amine, nitrogen heterocycle, nitrogen-oxygen heterocycle, etc., specifically introduced through organic amine silane coupling agents.

[0030] In a preferred embodiment, the amine-based silane coupling agent is selected from one or more of the following organic amine silane coupling agents: 3-aminopropyltrimethoxysilane, 3-aminoethyltrimethoxysilane, 3-aminomethyltrimethoxysilane, N,N-dimethylamino-3-aminopropyltriethylsilane, N,N-diethylamino-3-aminopropyltriethoxysilane, N-pyrrole-3-aminopropyltriethoxysilane, N-morpholino-3-aminopropyltriethoxysilane, and N-(2-methylimidazolium)-3-aminopropyltriethoxysilane.

[0031] In a preferred embodiment, the mixed solvent is a mixture of water and alcohol, wherein the alcohol is one of methanol, ethanol, isobutanol, and ethylene glycol, and the water content in the mixture is 30% to 70%.

[0032] In a preferred embodiment, the silica particles have a particle size of 100-1000 mesh, the reaction temperature is 15-40°C, and the surface modification is achieved by hydrolysis of an organic amine silane coupling agent and condensation reaction with hydroxyl groups on the silica surface.

[0033] In a preferred embodiment, the entire process of catalyst preparation must be protected by an inert gas, and the storage and use of the catalyst after preparation must also be isolated from air to avoid oxidation or absorption of gases such as carbon dioxide that could affect its quality.

[0034] In another embodiment, a method for preparing nitrophenoxy alcohol is provided, comprising the following steps: (1) The solid catalyst in the above-mentioned embodiments is filled into the bed of the fixed-bed reactor; (2) Nitrophenol and carbonate are passed through the bed in a fixed-bed reactor to carry out a catalytic transesterification reaction; (3) After the reaction is complete, the unreacted raw materials and by-products are removed from the solution, and the remaining substance is pure nitrophenoxy alcohol.

[0035] In the above embodiments, a fixed-bed reactor packed with a highly selective solid-phase catalyst is used. The nitrophenol and carbonate feedstocks are reacted by passing through the catalyst-filled fixed-bed reactor. This reaction exhibits high selectivity and almost no side reactions; therefore, only unreacted feedstocks and byproducts need to be removed to obtain pure nitrophenyloxy compounds. The single-pass conversion rate of the nitrophenol feedstock is detected by liquid chromatography. The single-pass conversion rate refers to the conversion rate of the total feed (including fresh feedstock and recycled feedstock) passing through the reactor in one pass. Simply put, the single-pass conversion rate is the conversion rate of the reaction without recycling; for the cyclic reaction of this invention, the total conversion rate is necessarily higher than the single-pass conversion rate. The number of cycles is a multiple of the total recycled feed amount relative to the total single-pass feed amount.

[0036] In a preferred embodiment, the single-pass conversion rate of the transesterification reaction is above 85%, and the purity of the reaction product after 3 to 5 material cycles can reach above 98%. The product purity of above 99% can be obtained through simple post-processing, and the yield is above 93%.

[0037] In a preferred embodiment, the mass hourly space velocity is 0.5-3 h. -1 The mass hourly space velocity (MHSV) represents the amount of feedstock passing through a unit volume of catalyst per unit time. MHSV is the ratio of feedstock mass flow rate to catalyst mass. The single-pass time is 15-60 min, preferably 20-30 min.

[0038] In a preferred embodiment, the nitrophenol may be selected from nitrophenol compounds such as o-nitrophenol, m-nitrophenol, o-nitrophenol, nitrocatechol, and nitroresorcinol; the carbonate may be selected from cyclic carbonates such as ethylene carbonate, propylene carbonate, and glycerol carbonate; and the molar ratio of nitrophenol to carbonate is 1:1.0 to 1:3.0.

[0039] In a preferred embodiment, the temperature of the catalyst bed in the fixed-bed reactor should be maintained within 100~200℃. The contact residence time between the raw material and the catalyst can be controlled by controlling the thickness of the catalyst-filled bed and the raw material flow rate to achieve a full reaction. Preferably, the material circulation number is 3~5 times, which can reduce the residual o-nitrophenol in the reaction solution to below 5%.

[0040] Preparation Example 1

[0041] The catalyst is prepared by the following steps: 1) In a 5L three-necked flask, add 1200g of pure water and 1800g of ethanol and stir to prepare a water-ethanol mixed solution. Add an appropriate amount of sodium hydroxide to adjust the pH to 12. Then add 100g of silica particles with a particle size of 300 mesh, introduce inert gas, and while stirring, add 400g of N,N-diethylamino-3-aminopropyltriethoxysilane under inert gas protection and react for 48 hours. 2) After the reaction was completed, the solvent and unreacted silane coupling agent were removed by vacuum distillation. The distillation temperature was gradually increased to 150°C and kept at that temperature for 5 hours. After cooling, the negative pressure was removed, and the system was replaced with an inert gas. Then, 2L of pure water was added and stirred and washed. After filtration to remove water, the solid silica was poured into a 5L three-necked flask. 1.5L of ethanol was added to the flask and stirred and washed. After washing, the flask was filtered again, and the filter cake was dried at 150°C under negative pressure to obtain 339g of catalyst product.

[0042] Preparation Example 2

[0043] In a 3L three-necked flask, 600g of pure water and 900g of ethanol were added and stirred to prepare a water-ethanol mixture. An appropriate amount of sodium hydroxide was added to adjust the pH to 11. Then, 100g of silica particles with a particle size of 300 mesh were added. An inert gas was introduced, and while stirring, 200g of 3-aminopropyltrimethoxysilane was added under the protection of the inert gas and the reaction was carried out for 48 hours.

[0044] After the reaction was completed, the solvent and unreacted silane coupling agent were removed by vacuum distillation. The distillation temperature was gradually increased to 150°C and held for 5 hours. After cooling, the negative pressure was removed, and the system was replaced with an inert gas. Then, 1L of pure water was added and stirred and washed. After filtration to remove water, the solid silica was poured into a 3L three-necked flask. 1L of ethanol was added to the flask and stirred and washed. After washing, the flask was filtered again, and the filter cake was dried at 150°C under negative pressure to obtain 355g of catalyst product.

[0045] Preparation Example 3

[0046] In a 3L three-necked flask, 600g of pure water and 900g of ethanol were added and stirred to prepare a water-ethanol mixture. An appropriate amount of sodium hydroxide was added to adjust the pH to 11. Then, 100g of silica particles with a particle size of 300 mesh were added. An inert gas was introduced, and while stirring, 200g of N-(2-methylimidazolium)-3-aminopropyltriethoxysilane was added under the protection of an inert gas and the reaction was carried out for 48 hours.

[0047] After the reaction was completed, the solvent and unreacted silane coupling agent were removed by vacuum distillation. The distillation temperature was gradually increased to 150°C and held for 5 hours. After cooling, the negative pressure was removed, and the system was replaced with an inert gas. Then, 1L of pure water was added and stirred to wash the mixture. After filtration to remove water, the solid silica was poured into a 3L three-necked flask. 1L of ethanol was added to the flask and the mixture was stirred and washed. After washing, the mixture was filtered again, and the filter cake was dried at 150°C under negative pressure to obtain 359g of the catalyst product.

[0048] Example 1

[0049] After multiple preparations in Preparation Example 1, 3 kg of the catalyst product was obtained and loaded into a fixed-bed reactor. The fixed-bed reactor system was purged with inert gas, sealed and stored, and protected by inert gas during the reaction.

[0050] 500g of molten o-nitrophenol and 733.42g of molten ethylene carbonate (molar ratio of o-nitrophenol to ethylene carbonate is 1:2.1) were mixed in a specific ratio and pumped through a fixed-bed reactor packed with 3kg of catalyst. The bed temperature was 110℃ and the reaction space velocity was 1.23h⁻¹. 1 The feed (including fresh and recycled feed) circulates three times between the storage tank and the fixed bed, with each circulation lasting 20 minutes. The single-pass conversion rate is 86.3%, and the conversion rate after three circulations is 98.4%. After the reaction, the liquid is mainly o-nitrophenoxyethoxyethanol, containing a small amount of unreacted o-nitrophenol and ethylene carbonate, as well as trace impurities, with a purity of 98.09% (detected by liquid chromatography). Figure 1 After washing away unreacted o-nitrophenol and ethylene carbonate with alkaline water, o-nitrophenoxyethoxyethanol was 98.80% (detected by liquid chromatography). Figure 2The yield was 96.35%, and the purity of the product met the requirements of industrial production in most industries. For a few industries with high quality requirements, o-nitrophenoxyethoxyethanol could be redistilled under high vacuum to obtain pure o-nitrophenoxyethoxyethanol, with a purity of 99.34% after distillation (detected by liquid chromatography). Figure 3 The yield was 94.12%. NMR characterization of o-nitrophenoxyethoxyethanol. 1 H-NMR ( Figure 4 )and 13 C-NMR ( Figure 5 (See attached image.)

[0051] Multiple syntheses were performed using this batch of catalyst, which could be reused multiple times. The purity and yield of the obtained o-nitrophenoxyethoxyethanol were not significantly different from those of the first synthesis.

[0052] Example 2

[0053] 1000g of molten o-nitrophenol and 838.20g of molten ethylene carbonate (molar ratio of o-nitrophenol to ethylene carbonate is 1:1.2) were mixed in a certain proportion using a pump and flowed through a fixed-bed reactor packed with 3kg of catalyst (Preparation Example 1). The bed temperature was 110℃ and the reaction space velocity was 1.22h⁻¹. 1 The feed (including fresh and recycled feed) circulated three times between the storage tank and the fixed bed, with each circulation lasting 30 minutes. The single-pass conversion rate was 87.7%, and the conversion rate after three circulations was 98.5%. After the reaction, the liquid mainly consisted of o-nitrophenoxyethanol, containing a small amount of unreacted o-nitrophenol, ethylene carbonate, and trace impurities. After washing away the unreacted o-nitrophenol and ethylene carbonate with alkaline water, the purity of o-nitrophenoxyethanol was 99.45%, and the yield was 95.28%.

[0054] Example 3

[0055] 1000g of molten o-nitrophenol and 733.87g of molten propylene carbonate (molar ratio of o-nitrophenol to propylene carbonate is 1:1) were mixed in a certain proportion using a pump and flowed through a fixed-bed reactor packed with 3kg of catalyst (Preparation Example 1). The bed temperature was 120℃ and the reaction space velocity was 1.14h⁻¹. 1 The feed (including fresh and recycled feed) circulated three times between the storage tank and the fixed bed, with each circulation lasting 30 minutes. The single-pass conversion rate was 85.9%, and the conversion rate after three circulations was 98.0%. The liquid after the reaction was mainly p-nitrophenoxyisopropanol, containing small amounts of unreacted o-nitrophenol, propylene carbonate, and trace impurities. After washing away the unreacted o-nitrophenol and propylene carbonate with alkaline water, the purity of p-nitrophenoxyisopropanol was 99.38%, and the yield was 94.26%.

[0056] Example 4

[0057] 500g of molten p-nitrophenol and 440.32g of molten propylene carbonate (molar ratio of p-nitrophenol to propylene carbonate is 1:1.2) were mixed in a specific ratio and pumped through a fixed-bed reactor packed with 3kg of catalyst. The bed temperature was 120℃ and the reaction space velocity was 0.93h⁻¹. 1 The feed (including fresh and recycled feed) circulated three times between the storage tank and the fixed bed, with each circulation lasting 20 minutes. The single-pass conversion rate was 86.2%, and the conversion rate after three circulations was 97.9%. After the reaction, the liquid mainly consisted of p-nitrophenoxyisopropanol, containing small amounts of unreacted p-nitrophenol, propylene carbonate, and trace impurities. After washing away the unreacted p-nitrophenol and propylene carbonate with alkaline water, the purity of p-nitrophenoxyisopropanol was 99.57%, and the yield was 94.26%.

[0058] Example 5

[0059] After multiple preparations in Preparation Example 2, 1 kg of the catalyst product was obtained and loaded into a fixed-bed reactor. The fixed-bed reactor system was purged with inert gas, sealed and stored, and protected by inert gas during the reaction.

[0060] 500g of molten p-nitrophenol and 366.94g of molten propylene carbonate (molar ratio of p-nitrophenol to propylene carbonate is 1:1) were mixed in a specific ratio and pumped through a fixed-bed reactor packed with 1kg of catalyst. The bed temperature was 120℃ and the reaction space velocity was 1.73h⁻¹. 1 The feed (including fresh and recycled feed) circulated three times between the storage tank and the fixed bed, with each circulation lasting 30 minutes. The single-pass conversion rate was 85.4%, and the conversion rate after three circulations was 98.6%. After the reaction, the liquid mainly consisted of p-nitrophenoxyisopropanol, containing small amounts of unreacted p-nitrophenol, propylene carbonate, and trace impurities. After washing away the unreacted p-nitrophenol and propylene carbonate with alkaline water, the p-nitrophenoxyisopropanol content was 99.46%, with a yield of 93.56%.

[0061] Example 6

[0062] After multiple preparations in Preparation Example 3, 1 kg of the catalyst product was obtained and loaded into a fixed-bed reactor. The fixed-bed reactor system was purged with inert gas, sealed and stored, and protected by inert gas during the reaction.

[0063] 500g of molten p-nitrophenol and 440.32g of molten propylene carbonate (molar ratio of p-nitrophenol to propylene carbonate is 1:1.2) were mixed in a specific ratio and pumped through a fixed-bed reactor packed with 1kg of catalyst. The bed temperature was 120℃ and the reaction space velocity was 1.88h⁻¹. 1 The feed (including fresh and recycled feed) circulated three times between the storage tank and the fixed bed, with each circulation lasting 30 minutes. The single-pass conversion rate was 86.0%, and the conversion rate after three circulations was 97.4%. After the reaction, the liquid mainly consisted of p-nitrophenoxyisopropanol, containing small amounts of unreacted p-nitrophenol, propylene carbonate, and trace impurities. After washing away the unreacted p-nitrophenol and propylene carbonate with alkaline water, the p-nitrophenoxyisopropanol content was 99.28%, with a yield of 93.45%.

[0064] Although embodiments of the invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made to these embodiments without departing from the principles and spirit of the invention, the scope of which is defined by the appended claims and their equivalents.

Claims

1. A method for preparing a solid-phase catalyst, characterized in that the steps include... include: Add silica particles to an alkaline alcohol-water mixed solvent system, add an organoamine silane coupling agent under a protective atmosphere, and then react fully with stirring at 15~40℃. The reaction product was desolventized and filtered to obtain a solid. The solid was then washed and dried to obtain a solid-phase catalyst.

2. The preparation method according to claim 1, characterized in that, In the alcohol-water mixed solvent system, the volume ratio of water is 30-70%. And / or, the alcohol is selected from methanol, ethanol, isobutanol, and ethylene glycol; And / or, the particle size of the silica particles is 100~1000 mesh; And / or, the reaction process is carried out under a protective gas.

3. The preparation method according to claim 1, characterized in that, The organoamine silane coupling agent is selected from at least one of 3-aminopropyltrimethoxysilane, 3-aminoethyltrimethoxysilane, 3-aminomethyltrimethoxysilane, N,N-dimethylamino-3-aminopropyltriethylsilane, N,N-diethylamino-3-aminopropyltriethoxysilane, N-pyrrole-3-aminopropyltriethoxysilane, N-morpholino-3-aminopropyltriethoxysilane, and N-(2-methylimidazolium)-3-aminopropyltriethoxysilane.

4. The preparation method according to claim 1, characterized in that, The drying process temperature is 100~180℃; And / or, the filtration, washing, and drying processes are carried out under a protective gas.

5. A solid-phase catalyst, characterized in that, It is prepared by the preparation method described in any one of claims 1 to 4.

6. The application of the solid-phase catalyst according to claim 5, characterized in that, The application is for the preparation of nitrophenoxy alcohols, and the preparation process uses nitrophenol and carbonate as reaction raw materials.

7. A method for preparing a nitrophenoxy alcohol, characterized in that, include: A solid catalyst is packed into the reactor to form a catalyst packing layer; Nitrophenol and carbonate are reacted by flowing through a catalyst-filled layer to obtain the reaction product; The reaction product was purified to obtain nitrophenoxy alcohol; The solid-phase catalyst is the solid-phase catalyst according to claim 5, or is prepared by any one of the preparation methods according to claims 1 to 4.

8. The preparation method according to claim 7, characterized in that, The nitrophenol is selected from o-nitrophenol, m-nitrophenol, o-nitrophenol, nitrocatechol, or nitroresorcinol; And / or, the carbonate is selected from ethylene carbonate, propylene carbonate or glycerol carbonate; And / or, the molar ratio of the nitrophenol to the carbonate is 1:(1~3).

9. The preparation method according to claim 7, characterized in that, The temperature of the catalyst filling layer is 100~200℃.

10. The preparation method according to claim 7, characterized in that, The reactor is a fixed-bed reactor, and the catalyst is filled into the bed to form a catalyst packing layer.

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