A process for the preparation of decanol by hydrogenation of decanal

Abstract

The present application belongs to the field of catalytic hydrogenation, and particularly relates to a method for preparing decanol by hydrogenating decanal. The method comprises: using a ruthenium catalyst to hydrogenate decanal to be saturated into decanol under gas-liquid-solid three-phase conditions; the ruthenium catalyst comprises an alumina carrier and ruthenium oxide particles loaded thereon; the content of ruthenium element in the ruthenium catalyst is 0.1-10 wt% based on the total weight of the ruthenium catalyst, and the content of the alumina carrier is 90-99.9 wt%; wherein the CO chemisorption amount of the ruthenium catalyst is 10-100 umol / g cat., and preferably 20-60 umol / g cat. The present application further improves the reaction activity of preparing decanol by hydrogenating decanal by using a ruthenium catalyst with highly dispersed active components; and the present application uses Ru as the active component of the catalyst for hydrogenating decanal, and has the characteristics of low temperature and high activity.

Description

Technical Field

[0001] This invention belongs to the field of catalytic hydrogenation, specifically, it relates to a method for preparing decanal by hydrogenation. Background Technology

[0002] The synthesis of plasticizers mainly uses butanol and octanol. Due to environmental protection and safety requirements, the use of alcohols with higher carbon numbers to produce plasticizers has been proposed and started. Decanol is one of them and has been put into industrial production. Decanol has a higher boiling point than octanol, and the plasticizers made from it have lower volatility, which is beneficial to environmental protection and human health. In recent years, it has received attention at home and abroad. 2-Propylheptanol is one of the important representatives of decanol. The main routes for producing decanol are: (1) obtaining C9 olefins through the trimerization of propylene or the oligomerization of propylene and butene, and then generating isodecanol through carbonyl synthesis and hydrogenation; (2) synthesizing pentanal by hydroformylation of butene, then generating decenal through condensation, and then generating decanol through hydrogenation.

[0003] Aldehyde hydrogenation processes are divided into gas-phase and liquid-phase methods. Gas-phase aldehyde hydrogenation suffers from drawbacks such as poor product quality, large reactor volume, high energy consumption, and inability to meet design load requirements. Liquid-phase hydrogenation, employing low temperature and high pressure, overcomes these disadvantages. However, for the production of higher alcohols, incomplete liquid-phase hydrogenation can lead to residual alkenals that negatively impact product quality.

[0004] Patent application CN101185893A discloses a catalyst for the gas-phase hydrogenation of decenal to isodecanol and its preparation method. The catalyst is prepared by co-precipitation and contains copper oxide, zinc oxide, aluminum oxide and active additives. It is used for the gas-phase hydrogenation of decenal to isodecanol and has a high decenal conversion rate (≥99.1%) and isodecanol selectivity (≥96.4%).

[0005] Patent application CN102666455A discloses a method for preparing at least one decanol by hydrogenating at least one decenal. It uses at least two reactors, with the first reactor employing a copper-based and / or nickel-based catalyst, and the second reactor employing a palladium or ruthenium catalyst, both carried out in the liquid phase on a solid catalyst. In this method, decenal can be hydrogenated to decanol in high yield, with the unsaturated decenal content in the hydrogenation product being less than 1500 ppm. However, the hydrogenation method in this patent application is relatively complex, employing multiple reactors in series, and the second reactor uses an expensive precious metal catalyst.

[0006] Currently, there is a contradiction between the activity and selectivity of liquid-phase hydrogenation catalysts, especially the selectivity, which is difficult to maintain at a normal level, resulting in numerous byproducts and causing problems in production. Moreover, in order to ensure product quality, a large amount of steam is required for impurity separation.

[0007] The hydrogenation of decanal to decanol requires a hydrogenation catalyst with both high activity and high selectivity. Therefore, developing novel ruthenium-based catalysts for the hydrogenation of decanal to further improve reactivity is of great significance for expanding the hydrogenation saturation reactions and processes of aldehydes. Summary of the Invention

[0008] The purpose of this invention is to provide a method for preparing decanal by hydrogenation, wherein the method further improves the reactivity of the hydrogenation of decanal to prepare decanal by a specific ruthenium catalyst.

[0009] To achieve the above objectives, the present invention provides a method for preparing decanol by hydrogenation of decanal, the method comprising:

[0010] Using a ruthenium catalyst, decanal was hydrogenated to decanol under gas-liquid-solid three-phase conditions;

[0011] The ruthenium catalyst comprises an alumina support and ruthenium oxide particles supported thereon; based on the total weight of the ruthenium catalyst, the ruthenium content in the ruthenium catalyst is 0.1–10 wt%, preferably 0.5–5 wt%, and the alumina support content is 90–99.9 wt%, preferably 95–99.5 wt%; wherein, the CO chemisorption capacity of the ruthenium catalyst is 10–100 μmol / g cat., preferably 20–60 μmol / g cat.

[0012] Compared with the prior art, the present invention has the following beneficial effects:

[0013] 1. This invention utilizes a ruthenium catalyst with highly dispersed active components to further enhance the reactivity of the hydrogenation of decanal to prepare decanol.

[0014] 2. This invention uses Ru as the active component of the decanal hydrogenation catalyst, which has the characteristics of low temperature and high activity.

[0015] Other features and advantages of the present invention will be described in detail in the following detailed description section. Attached Figure Description

[0016] Figure 1 A schematic diagram of an impregnation device is shown;

[0017] Figure 2 A side view of the internal structure of an impregnation device is shown;

[0018] Explanation of reference numerals in the attached figures:

[0019] 1-1, First motor; 1-2, Second motor; 1-3, Rotary reinforced packing bed; 1-4, Liquid storage tank; 1-5, Liquid pump; 1-6, Liquid distributor; 1-7, Rotary packing; 1-8, Carrier ring; 1-9, Alumina carrier; 1-10, Impregnating solution inlet; 1-11, Impregnating solution outlet;

[0020] 2-1. Wire mesh carrier ring gear; 2-2. Rotary reinforced packing bed; 2-3. Wire mesh carrier ring; 2-4. Alumina carrier; 2-5. Rotary packing; 2-6. Liquid distributor; 2-7. Impregnation liquid outlet. Detailed Implementation

[0021] The following provides a detailed description of specific embodiments of the present invention. It should be understood that the specific embodiments described herein are for illustrative and explanatory purposes only and are not intended to limit the scope of the invention.

[0022] This invention provides a method for preparing decyl alcohol by hydrogenation of decanal, the method comprising:

[0023] Using a ruthenium catalyst, decanal was hydrogenated to decanol under gas-liquid-solid three-phase conditions;

[0024] The ruthenium catalyst comprises an alumina support and ruthenium oxide particles supported thereon; based on the total weight of the ruthenium catalyst, the ruthenium content in the ruthenium catalyst is 0.1–10 wt%, preferably 0.5–5 wt%, and the alumina support content is 90–99.9 wt%, preferably 95–99.5 wt%; wherein, the CO chemisorption capacity of the ruthenium catalyst is 10–100 μmol / g cat., preferably 20–60 μmol / g cat.

[0025] The ruthenium catalyst mentioned above can also be used for the hydrogenation saturation of other aldehydes.

[0026] In this invention, the alumina carrier is preferably selected with a specific surface area of ​​100-300 m². 2 / g, pore volume of 0.5~1.5cm 3 Alumina carrier with a specific surface area of ​​140–250 m² / g is preferred. 2 / g, pore volume 0.7~1.2cm 3 / g alumina carrier. The alumina carrier mentioned above can be a commercially available molded alumina carrier, or an alumina carrier obtained by processing commercially available alumina, as long as the obtained alumina carrier meets the above-mentioned specific surface area and pore volume requirements. The processing method for commercially available alumina can be drying at 100-120℃ for 2-10 hours and calcining at 400-600℃ for 2-10 hours. For example, a specific surface area of ​​100-300 m² produced by the Beijing Chemical Research Institute can be selected. 2 / g, pore volume of 0.5~1.5cm 3 / g of molded alumina carrier.

[0027] As a preferred embodiment, the ruthenium catalyst is prepared by the following method:

[0028] The preparation method uses an impregnation device containing a liquid distributor, with a rotating packing and a carrier ring arranged sequentially around the liquid distributor; the liquid distributor is used to distribute the ruthenium salt solution as the impregnation liquid, and an alumina carrier is installed in the carrier ring.

[0029] The preparation method includes: under the action of centrifugal force, the rotating packing material rotating at a first speed shears the ruthenium salt solution sprayed from the liquid distributor into tiny liquid micro-elements, which come into contact with the alumina support in the support ring rotating at a second speed, and impregnate to obtain a ruthenium catalyst precursor; then drying and calcining to obtain the ruthenium catalyst;

[0030] The ratio of the first rotational speed to the second rotational speed is 30 to 400, preferably 50 to 200.

[0031] This invention utilizes rotational intensification technology, employing a rotating packed bed as the catalyst preparation equipment. Under centrifugal force, the impregnating solution forms a mist and droplets, which are sprayed onto the support surface at extremely high speeds. The highly dispersed fine droplets, the extremely high initial velocity, and the constantly renewing phase interface effectively increase the diffusion and permeation rate of the impregnating solution within the support pores, promoting the uniform adsorption of active components on the support surface and significantly shortening the impregnation time. Finally, after drying and calcination, a ruthenium catalyst with high hydrogenation activity is prepared.

[0032] As a preferred embodiment, in the reaction of hydrogenating decanal to decanol, the reaction temperature is 80-200℃ and the pressure is 0.1-10.0 MPa. More preferably, the reaction temperature is 90-130℃ and the pressure is 2-4 MPa.

[0033] As a preferred option, in the reaction of hydrogenating decanal to decanol, the liquid hourly space velocity is 0.1-4 h⁻¹. -1 More preferably, the liquid space velocity is 0.2-1.0 h⁻¹. -1 .

[0034] As a preferred option, the first speed is 1000-2000 rpm.

[0035] As a preferred option, the second speed is 10 to 20 rpm.

[0036] As a preferred option, the immersion time is 3 to 40 minutes, more preferably 3 to 30 minutes; considering both time cost and immersion effect, the immersion time is further preferably 3 to 7 minutes.

[0037] As a preferred option, the drying conditions include a temperature of 100–120°C and a time of 2–10 hours.

[0038] As a preferred option, the calcination conditions include a temperature of 400–600℃ and a time of 2–10 hours.

[0039] As a preferred embodiment, the ruthenium salt in the ruthenium salt solution is ruthenium nitrate and / or ruthenium chloride.

[0040] As a preferred embodiment, the concentration of ruthenium in the ruthenium salt solution, calculated as element, is 0.001–0.1 g / mL, more preferably 0.01–0.05 g / mL.

[0041] As a preferred embodiment, the rotating packing is wire mesh packing and / or cylindrical packing; more preferably, the rotating packing is stainless steel wire mesh packing and / or stainless steel cylindrical packing.

[0042] As a preferred embodiment, before the reaction of hydrogenating decanal to saturate it into decanol, the method further includes: introducing hydrogen gas to reduce the ruthenium catalyst. The reduction conditions are preferably: 350-500°C for 2-8 hours, so as to reduce some or all of the ruthenium oxide in the ruthenium catalyst to active ruthenium.

[0043] As a preferred embodiment, the impregnation apparatus includes:

[0044] Rotary strengthening packed bed; The rotary strengthening packed bed includes a liquid distributor, rotating packing and a carrier ring; The liquid distributor is located at the center of the rotary strengthening packed bed, and the rotating packing and carrier ring are arranged in sequence around the liquid distributor. The carrier ring is used to install the alumina carrier; The liquid distributor is used to distribute the impregnation liquid; The lower end of the rotary strengthening packed bed is provided with an impregnation liquid outlet for discharging the unimpregnated impregnation liquid;

[0045] The rotating packing and carrier ring are driven by different motors. The purpose of using different motors is to allow the rotating packing and carrier ring to rotate at different speeds.

[0046] As a preferred embodiment, the impregnation device also includes: a liquid storage tank and a liquid pump;

[0047] The storage tank is used to store the impregnation solution, which is then pumped to the liquid distributor by a liquid pump.

[0048] As a preferred option, the rotary reinforced packing bed has a cylindrical structure.

[0049] The present invention will be further described below with reference to the embodiments, but the scope of the present invention is not limited to these embodiments.

[0050] The testing instruments and conditions used in this embodiment are as follows:

[0051] The ruthenium metal content in the catalyst was determined by X-ray fluorescence spectroscopy.

[0052] The CO chemisorption capacity of the catalyst was measured using an ASPS2920 chemisorption analyzer from Micron Instruments, Inc. at ambient pressure and 35°C.

[0053] The raw materials used in the examples are from the following sources:

[0054] The molded alumina carrier was produced by Beijing Research Institute of Chemical Industry;

[0055] All other reagents used were commercially available and of analytical grade.

[0056] In this embodiment of the invention, a schematic diagram of the impregnation device is shown below. Figure 1 ,include:

[0057] The system comprises a first motor 1-1, a second motor 1-2, a rotary strengthening packing bed 1-3, a liquid storage tank 1-4, and a liquid pump 1-5. The rotary strengthening packing bed 1-3 includes a liquid distributor 1-6, rotary packing 1-7, and a carrier ring 1-8. The rotary strengthening packing bed 1-3 has a cylindrical structure. The liquid distributor 1-6 is located at the center of the rotary strengthening packing bed 1-3. The liquid distributor 1-6 is used to distribute the impregnation liquid. One end of the liquid distributor 1-6 is closed, and the other end has a pipe opening connected to the liquid pump 1-5 via a pipe. The outer periphery of the liquid distributor 1-6 is successively equipped with… A rotating packing 1-7 and a carrier ring 1-8 are arranged. The rotating packing 1-7 is made of stainless steel wire mesh, and the carrier ring 1-8 is used to mount the alumina carrier 1-9. The lower end of the rotating reinforced packing bed 1-3 is provided with an impregnation liquid outlet 1-11 to discharge unimpregnated impregnation liquid and return it to the storage tank 1-4. The storage tank 1-4 stores the impregnation liquid and pumps it to the impregnation liquid inlet 1-10 of the liquid distributor 1-6 via a liquid pump 1-5. The rotating packing 1-7 and the carrier ring 1-8 are driven by a second motor 1-2 and a first motor 1-1, respectively. For details of the impregnation device, see [link to relevant documentation]. Figure 2 Specifically, the carrier ring is selected as wire mesh carrier ring 2-3, which has wire mesh carrier ring gear 2-1 on it.

[0058] The first motor 1-1 drives the carrier ring 1-8 to rotate at a low speed, and the second motor 1-2 drives the rotating packing 1-7 to rotate at a high speed. The impregnation liquid is pumped into the impregnation device by the liquid pump 1-5 and evenly sprayed into the inner side of the rotating packing 1-7 by the liquid distributor 1-6. Under the action of high-speed centrifugal force, the impregnation liquid is sheared into tiny liquid micro-elements by the rotating packing 1-7 and comes into contact with the alumina carrier 1-9 in the low-speed rotating carrier ring 1-8 with extremely high tangential initial velocity. After a period of enhanced impregnation, a nickel catalyst precursor is obtained.

[0059] Preparation Example 1

[0060] The rotation-strengthened impregnation method was used to impregnate 50g of molded alumina carrier (produced by Beijing Research Institute of Chemical Industry, with a BET specific surface area of ​​143m²). 2 / g, pore volume is 0.74cm 3 The ruthenium precursor (0.01 g / mL) was loaded into a wire mesh carrier ring. An impregnation solution containing ruthenium chloride (0.01 g / mL) was placed in a liquid tank. The rotating packed bed was started, with the stainless steel wire mesh rotor rotating at 2000 rpm and the wire mesh carrier ring rotating at 10 rpm. The impregnation solution was pumped into the rotating bed using a horizontal pump. After 5 minutes of intensive impregnation, the catalyst precursor was removed and then dried at 120°C for 4 hours and calcined at 600°C for 6 hours. This yielded the ruthenium catalyst, denoted as A-1.

[0061] Preparation Example 2

[0062] The rotation-strengthened impregnation method was used to impregnate 50g of molded alumina carrier (produced by Beijing Research Institute of Chemical Industry, with a BET specific surface area of ​​143m²). 2 / g, pore volume is 0.74cm 3 The ruthenium precursor (0.01 g / mL) was loaded into a wire mesh carrier ring. An impregnation solution containing ruthenium chloride (0.01 g / mL) was placed in a liquid tank. The rotating packed bed was started, with the stainless steel wire mesh rotor rotating at 2000 rpm and the wire mesh carrier ring rotating at 10 rpm. The impregnation solution was pumped into the rotating bed using a horizontal pump. After 10 minutes of intensive impregnation, the catalyst precursor was removed and then dried at 120°C for 4 hours and calcined at 600°C for 6 hours. This yielded the ruthenium catalyst, denoted as A-2.

[0063] Preparation Example 3

[0064] The rotation-strengthened impregnation method was used to impregnate 50g of molded alumina carrier (produced by Beijing Research Institute of Chemical Industry, with a BET specific surface area of ​​143m²). 2 / g, pore volume is 0.74cm 3 The ruthenium precursor (0.01 g / mL) was loaded into a wire mesh carrier ring. An impregnation solution containing ruthenium chloride (0.01 g / mL) was placed in a liquid tank. The rotating packed bed was started, with the stainless steel wire mesh rotor rotating at 2000 rpm and the wire mesh carrier ring rotating at 10 rpm. The impregnation solution was pumped into the rotating bed using a horizontal pump. After 30 minutes of intensive impregnation, the catalyst precursor was removed and then dried at 120°C for 4 hours and calcined at 600°C for 6 hours. This yielded the ruthenium catalyst, designated A-3.

[0065] Preparation Example 4

[0066] The rotation-strengthened impregnation method was used to impregnate 50g of molded alumina carrier (produced by Beijing Research Institute of Chemical Industry, with a BET specific surface area of ​​143m²). 2 / g, pore volume is 0.74cm 3The ruthenium precursor (0.02 g / mL) was loaded into a wire mesh carrier ring. An impregnation solution containing ruthenium chloride (ruthenium concentration 0.02 g / mL) was placed in a liquid tank. The rotating packed bed was started, with the stainless steel wire mesh rotor rotating at 2000 rpm and the wire mesh carrier ring rotating at 10 rpm. The impregnation solution was pumped into the rotating bed using a horizontal pump. After 5 minutes of intensive impregnation, the catalyst precursor was removed and then dried at 120℃ for 4 hours and calcined at 600℃ for 6 hours. This yielded the ruthenium catalyst, denoted as A-4.

[0067] Preparation Example 5

[0068] Using the traditional impregnation method, 50g of molded alumina carrier (produced by Beijing Chemical Research Institute, with a BET specific surface area of ​​143m²) was impregnated. 2 / g, pore volume is 0.74cm 3 The catalyst D-1 was obtained by impregnating a sample (g) with an impregnation solution containing 0.05 g / mL ruthenium for 5 min, followed by drying at 100 °C for 10 h and calcining at 400 °C for 10 h.

[0069] Preparation Example 6

[0070] Using the traditional impregnation method, 50g of molded alumina carrier (produced by Beijing Chemical Research Institute, with a BET specific surface area of ​​143m²) was impregnated. 2 / g, pore volume is 0.74cm 3 The catalyst D-2 was obtained by impregnating a sample with ruthenium concentration of 0.02 g / mL in a solution for 30 min, followed by drying at 100 °C for 10 h and calcining at 400 °C for 10 h.

[0071] Preparation Example 7

[0072] Using the traditional impregnation method, 50g of molded alumina carrier (produced by Beijing Chemical Research Institute, with a BET specific surface area of ​​143m²) was impregnated. 2 / g, pore volume is 0.74cm 3 The catalyst D-3 was obtained by impregnating a sample (g) with an impregnation solution containing 0.01 g / mL ruthenium for 30 min, followed by drying at 100 °C for 10 h and calcining at 400 °C for 10 h.

[0073] Test Example 1

[0074] XRF tests were performed on samples A1-4 and D1-3 to characterize the ruthenium oxide content in the catalyst. The results are shown in Table 1.

[0075] Table 1

[0076]

[0077] Comparing the data in Table 1, it can be seen that the rotationally enhanced impregnation method can significantly shorten the time required for impregnation saturation. Under the same material conditions, the rotationally enhanced impregnation method can saturate the support in 5 minutes, while the traditional impregnation method requires 30 minutes. Furthermore, the CO adsorption capacity of the ruthenium catalyst prepared by the rotationally enhanced impregnation method is higher than that prepared by the traditional impregnation method. This indicates that the rotationally enhanced impregnation method can improve the metal dispersion, thereby enhancing catalytic activity.

[0078] Examples and Comparative Examples

[0079] Using a ruthenium catalyst, decanal was hydrogenated to decanol under gas-liquid-solid three-phase conditions. The reaction conditions are shown in Table 2. Among them, the examples are when the ruthenium catalyst is A-1 or A-4, and the comparative examples are when the ruthenium catalyst is D-1 or D-3.

[0080] Specifically, 20 mL of the reduced catalyst (reduced at 400℃ for 5 h) was introduced into a stainless steel reactor with an inner diameter of 18 mm. The reaction gas, hydrogen, was introduced at a flow rate of 200 mL / min and a hydrogen pressure of 4.0 MPa. Octanol containing 10% decanal (2-propylheptenal) was used as the raw material, and a micro-pump was used for injection. The reaction products were detected by online gas chromatography. The reaction results are shown in Table 2 (space velocity is expressed as decanal).

[0081] Table 2

[0082]

[0083] By comparing the data in Table 2, it can be seen that the ruthenium catalyst prepared by the rotation-enhanced impregnation method exhibits higher reactivity in the decanal hydrogenation reaction compared with the ruthenium catalyst prepared by the traditional impregnation method.

[0084] The various embodiments of the present invention have been described above. These descriptions are exemplary and not exhaustive, nor are they limited to the disclosed embodiments. Many modifications and variations will be apparent to those skilled in the art without departing from the scope and spirit of the described embodiments.

[0085] The endpoints and any values ​​of the ranges disclosed herein are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of the various ranges, the endpoint values ​​of the various ranges and individual point values, and individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed herein.

Claims

1. A method for preparing decanal by hydrogenation, characterized in that, The method includes: Using a ruthenium catalyst, decanal was hydrogenated to decanol under gas-liquid-solid three-phase conditions. In this reaction, the liquid hourly space velocity (LHSV) of decanal was 1–4 h⁻¹. -1 ; The ruthenium catalyst comprises an alumina support and ruthenium oxide particles supported thereon; based on the total weight of the ruthenium catalyst, the ruthenium content in the ruthenium catalyst is 0.1~10 wt%, and the alumina support content is 90~99.9 wt%; wherein, the CO chemisorption capacity of the ruthenium catalyst is 10-100 μmol / g cat. The ruthenium catalyst was prepared by the following method: The preparation method uses an impregnation device containing a liquid distributor, with a rotating packing and a carrier ring arranged sequentially around the liquid distributor; the liquid distributor is used to distribute the ruthenium salt solution as the impregnation liquid, and an alumina carrier is installed in the carrier ring. The preparation method includes: under the action of centrifugal force, the rotating packing material rotating at a first speed shears the ruthenium salt solution sprayed from the liquid distributor into tiny liquid micro-elements, which come into contact with the alumina support in the support ring rotating at a second speed, and impregnate to obtain a ruthenium catalyst precursor; then drying and calcining to obtain the ruthenium catalyst; the impregnation time is 3~7 min; The ratio of the first rotational speed to the second rotational speed is 30 to 400.

2. The method for preparing decanal by hydrogenation according to claim 1, wherein, Based on the total weight of the ruthenium catalyst, the ruthenium content in the ruthenium catalyst is 0.5~5 wt%, and the alumina support content is 95~99.5 wt%.

3. The method for preparing decanal by hydrogenation according to claim 1, wherein, The CO chemisorption capacity of the ruthenium catalyst is 20-60 μmol / g cat.

4. The method for preparing decanal by hydrogenation according to claim 1, wherein, The specific surface area of ​​the alumina carrier is 100~300m². 2 / g, pore volume of 0.5~1.5cm 3 / g.

5. The method for preparing decanal by hydrogenation according to claim 4, wherein, The specific surface area of ​​the alumina carrier is 140~250m². 2 / g, pore volume 0.7~1.2cm 3 / g.

6. The method for preparing decanal by hydrogenation according to claim 1, wherein, The ratio of the first rotational speed to the second rotational speed is 50 to 200.

7. The method for preparing decanal by hydrogenation according to claim 1, wherein, In the reaction of hydrogenating decanal to form decanol: The reaction temperature is 60-180℃ and the pressure is 0.1-10.0MPa.

8. The method for preparing decanal by hydrogenation according to claim 7, wherein, The reaction temperature is 90-130℃ and the pressure is 2-4MPa.

9. The method for preparing decanal by hydrogenation according to claim 1, wherein, The first rotational speed is 1000~2000 rpm; The second rotational speed is 10~20 rpm.

10. The method for preparing decanal by hydrogenation according to claim 1, wherein, The drying conditions include: a temperature of 100~120℃ and a time of 2~10h; The roasting conditions include: a temperature of 400~600℃ and a time of 2~10h.

11. The method for preparing decanal by hydrogenation according to claim 1, wherein, In the ruthenium salt solution, the ruthenium salt is ruthenium nitrate and / or ruthenium chloride; The concentration of ruthenium in the ruthenium salt solution, calculated as an element, is 0.001~0.1 g / mL.

12. The method for preparing decanal by hydrogenation according to claim 11, wherein, The concentration of ruthenium in the ruthenium salt solution, calculated as an element, is 0.01~0.05 g / mL.

13. The method for preparing decanal by hydrogenation according to claim 1, wherein, The rotating packing is wire mesh packing and / or cylindrical packing.

14. The method for preparing decanal by hydrogenation according to claim 13, wherein, The rotating packing is stainless steel wire mesh packing and / or stainless steel cylindrical packing.

15. The method for preparing decanal by hydrogenation according to claim 1, wherein, Before the reaction of decanal being hydrogenated to saturate decanol, the process also includes: introducing hydrogen gas to reduce the ruthenium catalyst.

16. The method for preparing decanal by hydrogenation according to claim 15, wherein, The reduction conditions are: 350~500℃ for 2~8 hours.

17. The method for preparing decanal by hydrogenation according to claim 1, wherein, The impregnation apparatus includes: A rotating reinforced packing bed (1-3) includes a liquid distributor (1-6), rotating packing (1-7), and a carrier ring (1-8). The rotating reinforced packing bed (1-3) has a liquid distributor (1-6) at its center, and the rotating packing (1-7) and the carrier ring (1-8) are arranged sequentially around the liquid distributor (1-6). The carrier ring (1-8) is used to mount an alumina carrier (1-9). The liquid distributor (1-6) is used to distribute the impregnation liquid. An impregnation liquid outlet (1-11) is provided at the lower end of the rotating reinforced packing bed (1-3) for discharging unimpregnated impregnation liquid. The rotating packing (1-7) and the carrier ring (1-8) are driven by different motors.

18. The method for preparing decanal by hydrogenation according to claim 17, wherein, The impregnation device also includes: a liquid storage tank (1-4) and a liquid pump (1-5). The storage tank (1-4) is used to store the impregnation liquid, and the liquid is pumped to the liquid distributor (1-6) by the liquid pump (1-5). The rotary reinforced packing bed (1-3) has a cylindrical structure.

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