CN113683545A - A system and method for preparing cyclohexyl hydrogen peroxide by oxidation of cyclohexane - Google Patents
A system and method for preparing cyclohexyl hydrogen peroxide by oxidation of cyclohexane Download PDFInfo
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Abstract
本发明提供了一种环己烷氧化制环己基过氧化氢的系统及方法，包括：反应器；所述反应器内设置有分隔板；所述反应器内位于所述分隔板上方的部位为反应段，位于所述分隔板下方的部分为分离段；所述反应段内设置有微界面发生器，所述微界面发生器浸没在液面以下；所述反应段内液面的上方设置有多层筛板；所述反应段的侧壁上设置有环己烷进口和空气进口；所述环己烷进口沿竖直方向设置在所述筛板的上方；所述空气进口与所述微界面发生器相连，空气经所述微界面发生器分散破碎成微米级别的微气泡后，进入所述反应段中。本发明的系统能耗低、成本低、安全性高、所需反应温度和压力低、副反应少、产物收率高，值得广泛推广应用。
The present invention provides a system and method for producing cyclohexyl hydrogen peroxide by oxidizing cyclohexane, comprising: a reactor; a dividing plate is arranged in the reactor; The part is the reaction section, and the part below the separating plate is the separation section; the reaction section is provided with a micro-interface generator, and the micro-interface generator is immersed below the liquid level; the liquid level in the reaction section is A multi-layer sieve plate is arranged above; a cyclohexane inlet and an air inlet are arranged on the side wall of the reaction section; the cyclohexane inlet is arranged above the sieve plate along the vertical direction; the air inlet and the The micro-interface generators are connected, and the air enters the reaction section after being dispersed and broken into micro-level micro-bubbles by the micro-interface generator. The system of the invention has low energy consumption, low cost, high safety, low required reaction temperature and pressure, few side reactions and high product yield, and is worthy of wide popularization and application.
Description
Technical Field
The invention relates to the field of cyclohexane oxidation reaction preparation, and particularly relates to a system and a method for preparing cyclohexyl hydroperoxide by cyclohexane oxidation.
Background
The oxidation of cyclohexane to prepare cyclohexyl hydroperoxide is an important intermediate for preparing cyclohexane or cyclohexanone; the cyclohexane air oxidation process is a mainstream process at home and abroad and comprises a non-catalytic oxidation process and a catalytic oxidation process; it is generally believed that the cyclohexane oxidation reaction is a free radical reaction during the cyclohexane oxidation. The cyclohexane oxidation reaction process is as follows: firstly, raw material benzene generates cyclohexane through benzene hydrogenation reaction, then the cyclohexane is oxidized into cyclohexyl hydrogen peroxide by air, the cyclohexyl hydrogen peroxide flows into the next device and is hydrolyzed under alkaline condition to generate cyclohexanol and cyclohexanone, and after saponification and separation, the cyclohexanol enters a dehydrogenation device to generate the cyclohexanone through dehydrogenation.
The prior cyclohexane oxidation reaction system mainly has the following problems:
(1) the oxidation reaction adopts a five-kettle series connection mode, the conversion rate of each kettle is gradually increased, but the total single-pass conversion rate is only 3.5%, a large amount of cyclohexane at the outlet of the No. 5 oxidation kettle enters a subsequent separation system, and is purified and then circulated back to the inlet of the No. 1 oxidation kettle, so that the separation energy consumption and the power consumption of the whole device are increased;
(2) the reaction temperature (165 ℃) and the reaction pressure (1.2MPa) are higher, and the increase of the temperature can cause the increase of byproducts, which is not favorable for improving the yield of the cyclohexyl hydroperoxide;
(3) compressed air is fed in a bubbling mode, so that the problems of uneven gas-liquid distribution and low mass transfer efficiency in a reaction kettle cause low reaction rate, low equipment utilization rate and uneven oxidation depth, and meanwhile, the oxygen content of tail gas discharged from the top of the reactor is higher, so that the effective utilization rate of oxygen in the compressed air is reduced;
(4) a large amount of cyclohexane and cyclohexyl hydrogen peroxide oxidation liquid enters a decomposition and alkali separation system, so that the investment on pipelines, instruments, valves and equipment for oxidizing reaction to a decomposition reaction section is large.
In view of the above, the present invention is particularly proposed.
Disclosure of Invention
The first purpose of the invention is to provide a system for preparing cyclohexyl hydroperoxide by cyclohexane oxidation, which integrates a reaction section and a separation section in a reactor by adopting a scheme of one tower and two kettles, thereby reducing the occupied area of the system and improving the integration degree of the system; through setting up little interfacial generator, can break into micron level's microbubble with the air dispersion, increased with the gas-liquid mass transfer area between cyclohexane, improved the oxidation efficiency of cyclohexane.
The second purpose of the invention is to provide a preparation method, which is simple and convenient to operate, and the obtained cyclohexyl hydroperoxide product has high quality, is beneficial to reducing energy consumption, and achieves better reaction effect than the prior art.
In order to achieve the above purpose of the present invention, the following technical solutions are adopted:
the invention provides a system for preparing cyclohexyl hydroperoxide by cyclohexane oxidation, which comprises: a reactor; a partition plate is arranged in the reactor; the part of the reactor above the partition plate is a reaction section, and the part of the reactor below the partition plate is a separation section; a micro-interface generator is arranged in the reaction section and is immersed below the liquid level;
a plurality of layers of sieve plates are arranged above the liquid level in the reaction section; a cyclohexane inlet and an air inlet are formed in the side wall of the reaction section; the cyclohexane inlet is arranged above the sieve plate along the vertical direction; the air inlet is connected with the micro-interface generator, and air is dispersed and crushed into micro-bubbles at the micron level by the micro-interface generator and then enters the reaction section;
a material outlet is formed in the side wall of the reaction section; the material outlet is arranged below the liquid level in the reaction section along the vertical direction; the material outlet is connected with the separation section.
In the prior art, the reaction temperature and pressure for preparing the cyclohexyl hydroperoxide by the cyclohexane oxidation reaction are high, a plurality of byproducts are generated, and the product yield is low; in addition, compressed air is generally fed in a bubbling mode in the prior art, but the problems of uneven gas-liquid distribution and low mass transfer efficiency in a reaction kettle still exist, so that the reaction rate is low, the equipment utilization rate is low, the oxidation depth is uneven, the oxygen content of tail gas discharged from the top of the reactor is higher, and the effective utilization rate of oxygen in the compressed air is reduced.
In order to solve the technical problems, the invention provides a system for preparing cyclohexyl hydroperoxide by cyclohexane oxidation, which integrates a reaction section and a separation section in a reactor by adopting a scheme of one tower and two kettles, thereby reducing the occupied area of the system and improving the integration degree of the system; through setting up little interfacial generator, can break into micron level's microbubble with the air dispersion, increased with the gas-liquid mass transfer area between cyclohexane, improved the oxidation efficiency of cyclohexane.
Preferably, the number of the micro-interface generators is two, the type of the micro-interface generator is a pneumatic micro-interface generator, and outlets of the two micro-interface generators are arranged oppositely. Two micro-interface generators are arranged to disperse and crush air at the same time, so that the micro-interface dispersion efficiency is improved; the outlets of the two micro-interface generators are oppositely arranged, so that the micro-bubbles of the two air streams are oppositely flushed, coalescence between the micro-bubbles is prevented, and the micro-bubbles are uniformly distributed.
Preferably, a gas distribution header is arranged at the outlet of the micro-interface generator, and the gas distribution header is communicated with the two micro-interface generators; the surface of the gas distribution pipe is provided with a plurality of gas holes. The gas distribution header is arranged to enable two micro-bubbles to do turbulent motion in the gas distribution header, and the micro-bubbles flow out from the air holes, so that the micro-bubbles are uniformly distributed.
Preferably, a liquid distributor is arranged above the sieve plate.
The reactor is divided into the reaction section at the upper part and the separation section at the lower part, so that the integration degree is high, and the occupied area is small; wherein, a micro-interface generator connected with an air inlet is arranged in the reaction section, when in reaction, air enters the micro-interface generator, is dispersed and crushed into micro-bubbles at the micron level and then is mixed with cyclohexane liquid to form gas-liquid emulsion, the gas-liquid mass transfer area of the cyclohexane and the air is increased, the reaction efficiency is improved, and simultaneously the required reaction temperature and pressure are greatly reduced,
in the invention, the number of the micro-interface generators is two, and the outlets of the two micro-interface generators are opposite and are connected through the gas distribution header. On one hand, micro-bubbles do turbulent motion in the gas distribution and collection pipe and enter the reaction section along the air holes on the pipe wall of the gas distribution and collection pipe, so that the uniform distribution of the micro-bubbles is promoted; on the other hand, two paths of micro bubbles form colliding flow, and are further dispersed and crushed through collision, so that the mass transfer efficiency of the micro interface is improved.
In addition, the positions of the cyclohexane inlet and the air inlet are not randomly arranged. The air inlet is arranged below the cyclohexane inlet because air is gas and is easy to overflow and scatter from the outlet, the reaction path of the air in the reaction section can be prolonged by arranging the air inlet below the cyclohexane inlet, oxygen in the air further reacts with cyclohexane, and the utilization rate and the conversion rate of raw materials are improved. The cyclohexane inlet is arranged above to shower from the upper part, and the liquid distributor is also arranged to promote the cyclohexane liquid to shower uniformly from the upper part to further react with the air overflowed from the upper part of the reaction section, so that the utilization rate of the raw materials is improved. The upper part of the liquid level in the reaction section is also provided with a plurality of layers of sieve plates, and the sieve plates can reduce the flow rate of gas at the top, thereby leading the cyclohexane which is dripped down to fully react with the cyclohexane. Therefore, the invention improves the conversion rate of raw materials and reduces the energy consumption required by the reaction by combining and applying the micro-interface generator and the sieve plate and specially setting the positions and the like of the micro-interface generator and the sieve plate.
It will be appreciated by those skilled in the art that the micro-interface generator used in the present invention is described in the prior patents of the present inventor, such as the patents of application numbers CN201610641119.6, CN201610641251.7, CN201710766435.0, CN106187660, CN105903425A, CN109437390A, CN205833127U and CN 207581700U. The detailed structure and operation principle of the micro bubble generator (i.e. micro interface generator) is described in detail in the prior patent CN201610641119.6, which describes that "the micro bubble generator comprises a body and a secondary crushing member, wherein the body is provided with a cavity, the body is provided with an inlet communicated with the cavity, the opposite first end and second end of the cavity are both open, and the cross-sectional area of the cavity decreases from the middle of the cavity to the first end and second end of the cavity; the secondary crushing member is disposed at least one of the first end and the second end of the cavity, a portion of the secondary crushing member is disposed within the cavity, and an annular passage is formed between the secondary crushing member and the through holes open at both ends of the cavity. The micron bubble generator also comprises an air inlet pipe and a liquid inlet pipe. "the specific working principle of the structure disclosed in the application document is as follows: liquid enters the micro-bubble generator tangentially through the liquid inlet pipe, and gas is rotated at a super high speed and cut to break gas bubbles into micro-bubbles at a micron level, so that the mass transfer area between a liquid phase and a gas phase is increased, and the micro-bubble generator in the patent belongs to a pneumatic micro-interface generator.
In addition, the first patent 201610641251.7 describes that the primary bubble breaker has a circulation liquid inlet, a circulation gas inlet and a gas-liquid mixture outlet, and the secondary bubble breaker communicates the feed inlet with the gas-liquid mixture outlet, which indicates that the bubble breakers all need to be mixed with gas and liquid, and in addition, as can be seen from the following drawings, the primary bubble breaker mainly uses the circulation liquid as power, so that the primary bubble breaker belongs to a hydraulic micro-interface generator, and the secondary bubble breaker simultaneously introduces the gas-liquid mixture into an elliptical rotating ball for rotation, thereby realizing bubble breaking in the rotating process, so that the secondary bubble breaker actually belongs to a gas-liquid linkage micro-interface generator. In fact, the micro-interface generator is a specific form of the micro-interface generator, whether it is a hydraulic micro-interface generator or a gas-liquid linkage micro-interface generator, however, the micro-interface generator adopted in the present invention is not limited to the above forms, and the specific structure of the bubble breaker described in the prior patent is only one of the forms that the micro-interface generator of the present invention can adopt.
Furthermore, the prior patent 201710766435.0 states that the principle of the bubble breaker is that high-speed jet flows are used to achieve mutual collision of gases, and also states that the bubble breaker can be used in a micro-interface strengthening reactor to verify the correlation between the bubble breaker and the micro-interface generator; moreover, in the prior patent CN106187660, there is a related description on the specific structure of the bubble breaker, see paragraphs [0031] to [0041] in the specification, and the accompanying drawings, which illustrate the specific working principle of the bubble breaker S-2 in detail, the top of the bubble breaker is a liquid phase inlet, and the side of the bubble breaker is a gas phase inlet, and the liquid phase coming from the top provides the entrainment power, so as to achieve the effect of breaking into ultra-fine bubbles, and in the accompanying drawings, the bubble breaker is also seen to be of a tapered structure, and the diameter of the upper part is larger than that of the lower part, and also for better providing the entrainment power for the liquid phase.
Since the micro-interface generator was just developed in the early stage of the prior patent application, the micro-interface generator was named as a micro-bubble generator (CN201610641119.6), a bubble breaker (201710766435.0) and the like in the early stage, and is named as a micro-interface generator in the later stage along with the continuous technical improvement, and the micro-interface generator in the present invention is equivalent to the micro-bubble generator, the bubble breaker and the like in the prior art, and has different names. In summary, the micro-interface generator of the present invention belongs to the prior art.
Preferably, the air inlet is connected with an air pipeline, the air pipeline is provided with a gas filter, and air flows into the reaction section after being filtered by the gas filter. The air is filtered and then sent to the reaction section, so that the micro-interface generator is effectively prevented from being blocked by impurities in the air.
Preferably, the material outlet is connected with a circulating external cooler, and the circulating external cooler is connected with the micro-interface generator; and one part of the material generated in the reaction section enters the separation section, and the other part of the material flows back to the micro-interface generator after being cooled by the circulating external cooler.
Preferably, the cyclohexane inlet is connected with a cyclohexane pipeline; the top of the separation section is connected with a reflux tank, the reflux tank is connected with the cyclohexane pipeline, and cyclohexane separated by the reflux tank returns to the reaction section for continuous reaction.
Preferably, the bottom of the separation section is connected with a condenser, and a product separated from the separation section is collected after being condensed by the condenser.
The invention also provides a preparation method of the system for preparing the cyclohexyl hydrogen peroxide by oxidizing the cyclohexane, which comprises the following steps:
air is dispersed and crushed into micro bubbles in micron level through a micro interface, and then the micro bubbles are mixed with cyclohexane for oxidation reaction, and cyclohexyl hydrogen peroxide is obtained after separation.
Preferably, the oxidation reaction temperature is 150-160 ℃, and the pressure is 0.6-1.0 MPa.
The cyclohexyl hydroperoxide product obtained by the reaction method of the invention has good quality and high yield. And the preparation method has the advantages of low reaction temperature, greatly reduced pressure and remarkably reduced cost.
Compared with the prior art, the invention has the beneficial effects that:
(1) according to the system for preparing the cyclohexyl hydrogen peroxide by cyclohexane oxidation, the reaction section and the separation section are integrated in one reactor by adopting a scheme of one tower and two kettles, so that the occupied area of the system is reduced, and the integration degree of the system is improved;
(2) the micro-interface generator is arranged, so that air can be dispersed and crushed into micro-bubbles at the micron level, the gas-liquid mass transfer area between the micro-interface generator and cyclohexane is increased, and the oxidation efficiency of the cyclohexane is improved;
(3) the outlets of the two micro-interface generators are opposite and connected through the gas distribution header, so that on one hand, micro-bubbles do turbulent motion in the gas distribution header and enter the reaction section along the gas holes on the pipe wall of the gas distribution header, and the uniform distribution of the micro-bubbles is promoted; on the other hand, two paths of micro bubbles form colliding flow, and are further dispersed and crushed through collision, so that the mass transfer efficiency of the micro interface is improved.
Drawings
Various other advantages and benefits will become apparent to those of ordinary skill in the art upon reading the following detailed description of the preferred embodiments. The drawings are only for purposes of illustrating the preferred embodiments and are not to be construed as limiting the invention. Also, like reference numerals are used to refer to like parts throughout the drawings. In the drawings:
FIG. 1 is a schematic structural diagram of a system for preparing cyclohexylhydroperoxide by cyclohexane oxidation according to an embodiment of the present invention;
FIG. 2 is a schematic structural diagram of a reactor provided in an embodiment of the present invention;
FIG. 3 is a schematic structural view of a gas distributor according to an embodiment of the present invention;
FIG. 4 is a schematic diagram of a system for preparing cyclohexyl hydroperoxide by cyclohexane oxidation in the prior art.
Description of the drawings:
a 10-cyclohexane line; 20-an air line;
30-a gas filter; 40-a reactor;
50-a reaction section; 501-air inlet;
502-cyclohexane inlet; 503-sieve plate;
504-a micro-interface generator; 505-gas distribution manifold;
506-material outlet; 507-pores;
508-a liquid distributor; 60-a separation section;
70-a reflux tank; 80-a condenser;
90-circulating external cooler; 100-partition plate.
Detailed Description
The technical solutions of the present invention will be clearly and completely described below with reference to the accompanying drawings and the detailed description, but those skilled in the art will understand that the following described embodiments are some, not all, of the embodiments of the present invention, and are only used for illustrating the present invention, and should not be construed as limiting the scope of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
In the description of the present invention, it should be noted that the terms "center", "upper", "lower", "left", "right", "vertical", "horizontal", "inner", "outer", etc., indicate orientations or positional relationships based on the orientations or positional relationships shown in the drawings, and are only for convenience of description and simplicity of description, but do not indicate or imply that the device or element being referred to must have a particular orientation, be constructed and operated in a particular orientation, and thus, should not be construed as limiting the present invention. Furthermore, the terms "first," "second," and "third" are used for descriptive purposes only and are not to be construed as indicating or implying relative importance.
In the description of the present invention, it should be noted that, unless otherwise explicitly specified or limited, the terms "mounted," "connected," and "connected" are to be construed broadly, e.g., as meaning either a fixed connection, a removable connection, or an integral connection; can be mechanically or electrically connected; they may be connected directly or indirectly through intervening media, or they may be interconnected between two elements. The specific meanings of the above terms in the present invention can be understood in specific cases to those skilled in the art.
In order to more clearly illustrate the technical solution of the present invention, the following description is made in the form of specific embodiments.
Examples
Referring to fig. 1-3, the present embodiment provides a system for preparing cyclohexyl hydroperoxide by cyclohexane oxidation, comprising: a reactor 40; a partition plate 100 is arranged in the reactor 40; the part of the reactor 40 above the partition plate 100 is a reaction section 50, and the part below the partition plate 100 is a separation section 60; a micro-interface generator 504 is arranged in the reaction section, and the micro-interface generator 504 is immersed below the liquid level;
a multilayer sieve plate 503 is arranged above the liquid level in the reaction section 50; a cyclohexane inlet 502 and an air inlet 501 are arranged on the side wall of the reaction section 50; the cyclohexane inlet 502 is arranged above the sieve plate 503 along the vertical direction; the air inlet 501 is connected with the micro-interface generator 504, and air is dispersed and crushed into micro-bubbles at a micron level by the micro-interface generator 504 and then enters the reaction section 50; the side wall of the reaction section 50 is provided with a material outlet 506; the material outlet 506 is arranged below the liquid level in the reaction section 50 along the vertical direction; the material outlet 506 is connected to the separation section 60.
In order to promote the liquid to uniformly drop, a liquid distributor 508 is disposed above the sieve plate 503.
In this embodiment, the number of the micro-interface generators 504 is two, and the outlets of the two micro-interface generators 504 are arranged oppositely. A gas distribution header 505 is arranged at the outlet of the micro-interface generator 504, and the gas distribution header 505 is communicated with the two micro-interface generators 504; the gas distribution header 505 is provided with a plurality of gas holes 507 on its surface. Two micro-bubbles make turbulent motion in the gas distribution pipe 505, and the micro-bubbles flow out from the air holes 507, so that the micro-bubbles are uniformly distributed.
The micro-interface generator 504 may be a pneumatic micro-interface generator, a hydraulic micro-interface generator, or a gas-liquid linkage micro-interface generator. In this embodiment, both of the micro-interface generators 504 are pneumatic micro-interface generators.
As shown in fig. 1, in the present embodiment, the air inlet 501 is connected to an air pipe 20, the air pipe 20 is provided with a gas filter 30, and the air flows into the reaction section 50 after being filtered by the gas filter 30. The material outlet 506 is connected with a circulating external cooler 90, and the circulating external cooler 90 is connected with the micro-interface generator 504; a portion of the material produced in the reaction section 50 enters the separation section 60 and another portion is cooled in the recycle intercooler 90 and flows back to the micro-interfacial generator 504. The cyclohexane inlet 502 is connected with a cyclohexane pipeline 10; the top of the separation section 60 is connected with a reflux tank 70, the reflux tank 70 is connected with a cyclohexane pipeline 10, and cyclohexane separated by the reflux tank 70 returns to the reaction section 50 for continuous reaction. The bottom of the separation section 60 is connected with a condenser 80, and the product separated from the separation section 60 is collected after being condensed by the condenser 80.
In fact, the return tank 70 is also provided with a waste water outlet and an exhaust gas outlet for discharging the separated waste water and exhaust gas. The top of the reaction section 50 is provided with a gas outlet, and tail gas generated by the reaction is discharged from the gas outlet.
During the reaction, air and cyclohexane are fed into the reaction zone 50. Air is dispersed and crushed into micro bubbles in micron level through a micro interface, and then the micro bubbles are mixed with cyclohexane for oxidation reaction, and the cyclohexyl hydroperoxide is obtained after separation through a separation section 60.
The specific reaction conditions are as follows: controlling the total air feed flow to 21.3m3H, cyclohexane feed 5.0m3H, at 150 ℃ and 0.6 Mpa; 155 ℃, 0.8 Mpa; the reaction was carried out at 160 ℃ and 1.0MPa, respectively. The specific experimental parameters were as follows:
TABLE 1
Experimental example 4
This example differs from experimental example 2 in that no micro-interface generator and no gas distribution manifold were used. The reaction parameters were as follows: the liquid phase residence time was 55min and the space-time yield was 0.0298 t/(m)3H) the single pass conversion of cyclohexane was 3.6%.
Experimental example 5
This example differs from experimental example 2 in that only one micro-interface generator was used and no gas distribution manifold was used. The reaction parameters were as follows: liquid phase residence time of 43min, space-time yield 0.0323 t/(m)3H) the single pass conversion of cyclohexane was 4.3%.
Comparative example
Fig. 4 is a schematic diagram of an oxidation system in the prior art. Controlling the total air feed flow to 21.3m3H, cyclohexane feed 5.0m3The reaction is carried out at 165 ℃ and 1.2Mpa, and the specific parameters are as follows: wherein the liquid phase residence time is 54.8min, and the space-time yield is 0.0293 t/(m)3H) the single pass conversion of cyclohexane was 3.5%.
Compared with the prior art, the system of the invention has the advantages of obviously reduced energy consumption and greatly improved raw material conversion rate.
In a word, compared with the prior art, the system has the advantages of low energy consumption, low cost, high safety, low required reaction temperature and pressure, less side reaction and high product yield, and is worthy of wide popularization and application.
Finally, it should be noted that: the above embodiments are only used to illustrate the technical solution of the present invention, and not to limit the same; while the invention has been described in detail and with reference to the foregoing embodiments, it will be understood by those skilled in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; and the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the scope of the technical solutions of the embodiments of the present invention.
Claims (10)
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| CN113041962A (en) * | 2021-04-01 | 2021-06-29 | 南京延长反应技术研究院有限公司 | Reaction system and method for preparing butyraldehyde by propylene carbonylation |
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