CN114315518A - Chlorohydrination reaction device and application thereof - Google Patents
Chlorohydrination reaction device and application thereof Download PDFInfo
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- CN114315518A CN114315518A CN202011053198.1A CN202011053198A CN114315518A CN 114315518 A CN114315518 A CN 114315518A CN 202011053198 A CN202011053198 A CN 202011053198A CN 114315518 A CN114315518 A CN 114315518A
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Abstract
The invention discloses a chlorohydrination reaction device and application thereof. The reaction device comprises a hypochlorous acid reaction area and a chlorohydrination reaction area, wherein the two reaction areas comprise gas phase areas, and the gas phase areas are independent from each other and are used for accommodating unreacted reaction gas in the reaction areas; wherein "independent from each other" means that the gases in the two gas phase zones are each independently present and do not contact each other. By arranging two independent gas phase spaces, the side reaction caused by direct gas phase contact of chlorine and olefin is avoided, the generation of low-value chlorination byproducts is greatly reduced, and the unit consumption of raw materials of chlorohydrin is reduced.
Description
Technical Field
The invention belongs to the field of chlorohydrination reaction, and particularly relates to a chlorohydrination reaction device and application thereof.
Background
Chlorohydrination is one of the important industrial processes for producing alkylene oxide, such as contacting chlorine gas with propylene in water, reacting hypochlorous acid generated from chlorine gas and water with propylene to generate chloropropanol, and contacting chloropropanol with calcium hydroxide to generate Propylene Oxide (PO). The method for preparing the alkylene oxide by chlorohydrination has the advantages of short flow, mature process, safe production, small capital investment and the like.
In the chlorohydrination reaction process of the propylene, side reactions exist simultaneously in the main reaction, and byproducts such as chloropropanol and dichloropropane are generated.
Main reaction:
side reaction:
the reaction of propylene with hypochlorous acid (equation (2)) is rapid, and propylene reacts rapidly with free chlorine (equation (3)) to form dichloropropane as a by-product. The chlorohydrination reactors used in industry include single-tower chlorohydrination reactor, tubular chlorohydrination reactor, three-tower series chlorohydrination reactor and tube-tower combined chlorohydrination reactor, and the reactors all have the same defects: undissolved chlorine and unreacted olefin diffuse into the same gas phase space to react rapidly to generate byproducts, such as a chlorohydrination method propylene oxide preparation device, wherein the byproduct of propylene oxide is 180kg of dichloropropane which is a low-value solvent and is 150-180kg per ton of propylene oxide.
Disclosure of Invention
In order to improve the disadvantages of the prior art, the present invention provides a chlorohydrination reaction apparatus comprising a hypochlorous acid reaction zone and a chlorohydrination reaction zone, both of which comprise gas phase zones, each of which is independent of the other, for accommodating unreacted reaction gas in each reaction zone.
Wherein "independent from each other" means that the gases in the two gas phase zones are each independently present and do not contact each other.
According to an embodiment of the present invention, the hypochlorous acid reaction zone and the chlorohydrination reaction zone each further comprise a solution zone, and the solution zone of the hypochlorous acid reaction zone is denoted as a first solution zone, and the solution zone of the chlorohydrination reaction zone is denoted as a second solution zone.
According to an embodiment of the present invention, in each reaction zone, the gas phase zone is located above the solution zone.
According to an embodiment of the invention, the first solution zone and the second solution zone are in communication or not, preferably in communication. It will be understood by those skilled in the art that the manner of achieving communication is not particularly limited, and for example, the hypochlorous acid reaction zone and the chlorohydrination reaction zone are connected by a line to achieve communication of the solution zone.
For example, a first communication line may be provided at the bottom of the hypochlorous acid reaction zone and the chlorohydrination reaction zone to allow communication between the first solution zone and the second solution zone.
Preferably, a second communication line may be further provided at an upper middle portion of the hypochlorous acid reaction zone and an upper middle portion of the chlorohydrination reaction zone to achieve circulation of the liquid in the first solution zone and the second solution zone.
Preferably, a liquid delivery device may be provided on any one of the communication lines, such as on the second communication line. Preferably, the liquid delivery device may be a pump.
According to an embodiment of the present invention, the gas phase zone of the hypochlorous acid reaction zone is denoted as a first gas phase zone for containing unreacted chlorine gas, and the gas phase zone of the chlorohydrination reaction zone is denoted as a second gas phase zone for containing unreacted olefin.
According to an embodiment of the present invention, the first gas phase zone is connected to the first solution zone, and the second gas phase zone is connected to the second solution zone at the solution level.
According to an embodiment of the present invention, the reaction apparatus includes a line for introducing chlorine gas, and a gas outlet of the line for introducing chlorine gas is provided in the first solution zone.
According to an embodiment of the invention, the reaction apparatus further comprises a first gas phase line connected to the first gas phase zone for the discharge of unreacted chlorine gas.
According to an embodiment of the present invention, the first gas phase line may be connected to a chlorine gas introduction line, and the chlorine gas withdrawn from the first gas phase zone may be recycled as a raw material gas. Preferably, a pressure-increasing device is provided in the connecting line between the first gas phase line and the chlorine gas introduction line. For example, the pressure boosting device may be a compressor or a fan.
According to an embodiment of the present invention, the reaction apparatus further comprises at least one line for introducing olefin, and the gas outlet of the line for introducing olefin is provided at least in the second solution zone, preferably in the middle-lower part of the second solution zone. Further, when the olefin introducing line is two, the gas outlet of one olefin introducing line is provided in the second solution zone (preferably, in the middle-lower part of the second solution zone), and the other olefin introducing line is provided in the middle-lower part of the first solution zone (preferably, opposite to the chlorine introducing line).
According to an embodiment of the invention, the olefin may be selected from ethylene, propylene, chloropropene or butene, etc.
According to an embodiment of the present invention, the reaction apparatus further comprises a second gas phase line connected to the second gas phase zone for discharging unreacted olefins.
According to an embodiment of the present invention, the second gas phase line is connected to an olefin introduction line communicating with the second solution zone, and the gas phase withdrawn from the second gas phase zone is recycled as a raw material gas. Preferably, a pressurizing means is provided on a connecting line of the second gas phase line and the olefin introducing line communicating with the second solution zone. For example, the pressure boosting device may be a compressor or a fan.
According to an embodiment of the present invention, the reaction apparatus may further comprise a process water line for supplementing water required for the reaction in each reaction zone. Preferably, the process water lines are connected to the respective gas phase zones.
According to an embodiment of the present invention, the hypochlorous acid reaction area and the chlorohydrination reaction area further comprise an insulation layer. Preferably, the insulating layer covers at least the solution zone.
According to an embodiment of the present invention, the reaction apparatus may further include a reaction liquid outflow line connected to the second solution zone, preferably located at an upper portion of the second solution zone.
According to an embodiment of the invention, the reaction apparatus further comprises an agitator for agitation of the contents of the solution zone in each reaction zone.
The invention also provides the application of the chlorohydrination reaction device in chlorohydrin preparation and/or propylene oxide preparation.
The invention also provides a preparation method of the chlorohydrin, which comprises the following steps: chlorine and olefin react in the chlorohydrination reaction device to prepare chlorohydrin.
According to the embodiment of the invention, chlorine gas is introduced into the first solution zone, the chlorine gas is contacted with water and then is subjected to dissolution reaction to generate hypochlorous acid and HCl, and the undissolved chlorine gas enters the first gas phase zone; the second solution zone is fed with an olefin, the olefin is reacted with the aqueous hypochlorous acid solution from the first solution zone in the second solution zone to produce a chlorohydrin, and the unreacted olefin is introduced into the second vapor phase zone.
According to an embodiment of the invention, the olefin is ethylene, propylene, chloropropene or butene, etc.
According to an embodiment of the invention, the ratio of the total molar amount of olefin to the molar amount of chlorine is (1.01-1.3):1, e.g. (1.05-1.16): 1.
According to the embodiment of the present invention, the ratio of the molar amount of the olefin fed through the olefin feeding line to the molar amount of the chlorine fed through the chlorine feeding line, which is disposed in the lower portion in the first solution zone, is (0-0.99): 1.
According to an embodiment of the present invention, the reaction temperature is 10 to 100 ℃, preferably 30 to 80 ℃, and more preferably 40 to 60 ℃.
The invention has the beneficial effects that:
according to the chlorohydrination reaction device provided by the invention, chlorine gas is introduced into the middle lower part of the first solution zone, and is dissolved and reacted after being contacted with water to generate hypochlorous acid and HCl, and undissolved chlorine gas enters the first gas phase zone; olefin is introduced into the middle lower part of the second solution zone, the olefin reacts with the hypochlorous acid aqueous solution from the first solution zone in the second solution zone, and unreacted olefin enters the second gas phase zone. Undissolved chlorine and unreacted olefin enter different gas phase regions respectively, and the chlorination byproducts generated by direct meeting and rapid reaction are avoided. The device reduces or even avoids the contact reaction of undissolved chlorine and olefin in a gas phase space by arranging two independent gas phase areas, and effectively reduces the generation of byproducts.
Drawings
Fig. 1 is a schematic structural diagram of a chlorohydrination reaction apparatus provided in example 1.
FIG. 2 is a schematic diagram of the chloropropanol production apparatus provided in example 2 and having a double-glass round-bottom flask as the reaction zone.
FIG. 3 is a schematic diagram showing the structure of an apparatus for preparing chloropropanol using a single round bottom glass flask as a reaction zone, which is used in a comparative example.
V11, a first gas phase zone, V12, a first solution zone, V21, a second gas phase zone, V22, a second solution zone, 1, a pipeline for chlorine gas introduction, 2, a pipeline for olefin introduction, 3, a first gas phase pipeline, 4, a second gas phase pipeline, 5, a first communicating pipeline, 6, a second communicating pipeline, 7, a process water pipeline, 8, a chlorohydrin product outlet line, 9, a delivery pump, 10, a first solution zone stirrer, 11, and a second solution zone stirrer.
Detailed Description
The technical solution of the present invention will be further described in detail with reference to specific embodiments. It is to be understood that the following examples are only illustrative and explanatory of the present invention and should not be construed as limiting the scope of the present invention. All the technologies realized based on the above-mentioned contents of the present invention are covered in the protection scope of the present invention.
Unless otherwise indicated, the raw materials and reagents used in the following examples are all commercially available products or can be prepared by known methods.
The product analysis conditions for the following examples and comparative examples are as follows:
an analytical instrument: agilent GC 7820; a chromatographic column: 30 m.times.530 μm.times.0.25 μm DB-FFAP; a detector: FID; sample inlet temperature: 225 ℃, detector temperature: and (3) temperature programming at 240 ℃: keeping at 40 deg.C for 5min, 30 deg.C/min to 230 deg.C for 5 min; h2：0.1Mpa，AIR：0.1Mpa，N2: 0.075Mpa, tail-blown: 0.1 MPa.
Example 1
The chlorohydrination reaction apparatus shown in figure 1 comprises: a hypochlorous acid reaction zone and a chlorohydrination reaction zone, a chlorine gas introducing line 1, an olefin introducing line 2, a first gas phase line 3, a second gas phase line 4, a process water line 7 and a chlorohydrin product outlet line 8. The hypochlorous acid reaction zone comprises a first gas phase zone V11 and a first solution zone V12, the chlorohydrination reaction zone comprises a second gas phase zone V21 and a second solution zone V22, the first gas phase zone V11 and the second gas phase zone V21 are independent from each other, and the gas phase zones are located above the solution zones in each reaction zone.
A chlorine gas introducing line 1 leads to a lower middle portion of the first solution zone V12, an olefin introducing line 2 leads to a lower middle portion of the second solution zone V22, and the opposite side of the first solution zone from the chlorine gas introducing line 1. The bottom of first solution zone V12 and the bottom of second solution zone V22 are connected through first communicating pipe 5, the middle upper part of first solution zone V12 and the middle upper part of second solution zone V22 are connected through second communicating pipe 6, the material flow directions in the first communicating pipe and the second communicating pipe are opposite, and any pipe is provided with conveying equipment (not shown in the figure) such as a pump.
The upper part of the second solution zone V22 is connected with the chlorohydrin product outlet line 8 to extract a chlorohydrin reaction product. The first gas phase zone V11 is connected to the first solution zone V12 at a liquid phase interface, the top of the first gas phase zone is connected to a first gas phase line 3, and the upper part of the first gas phase zone is connected to a process water line 7. The second vapor space V21 is connected to the second solution zone V22 at a liquid phase interface, the top of the second vapor zone is connected to a second vapor line 4, and the upper part of the second vapor zone is connected to a process water line 7.
In one embodiment, the first gas phase pipeline is connected with a pipeline for introducing chlorine gas, a pressurizing device is arranged on the connecting pipeline, and the gas phase extracted from the first gas phase area is recycled as raw material gas. The second gas phase pipeline is connected with an olefin inlet pipeline, a supercharging device is arranged on the connecting pipeline, and the gas phase extracted from the second gas phase area is used as the raw material gas for recycling.
Example 2
Chlorohydrination of propene to prepare chloropropanol:
as shown in FIG. 2, the reaction apparatus comprises a hypochlorous acid reaction zone and a chlorohydrination reaction zone, the two reaction zones are two 500ml four-neck round bottom glass flasks, the bottoms of the flasks are communicated through a first communication pipe 5 (in this example, a glass tube), the total volume of the reaction solution is 800ml, and hot water is introduced into a jacket to control the reaction temperature to 50 ℃. The reaction flask was equipped with a mechanical stirrer: the first solution zone stirrer 10 and the second solution zone stirrer 11 were stirred at a speed of 100 rpm. A metering pump 9 is provided on the second communication line 6, and the flow rate of the delivery pump 9 is 26.5L/h.
Chlorine gas was passed into the first solution zone V12 at a rate of 52ml/min (2.3mmol/min) via line 1 for chlorine gas introduction and propylene was passed into the second solution zone V22 at a rate of 62ml/min (2.7mmol/h) via line 2 for olefin introduction. Solution is withdrawn from the second solution zone by transfer pump 9 and passed into first solution zone V12 from first solution zone V12 via first communication line 5 to second solution zone V22 and from second solution zone V22 via second communication line 6 to first solution zone V12.
Undissolved chlorine is discharged from the first gas phase pipeline 3, absorbed by alkali liquor, and metered and analyzed. Unreacted propylene and the like were taken out from the second gas phase line 4, absorbed by ethyl acetate at-20 ℃ and quantitatively analyzed.
After the gas is ventilated for 190min, the mass fraction of chloropropanol in the reaction liquid reaches about 3.5 wt%.
The chloropropanol and impurity contents in the reaction materials are analyzed, the chlorine and impurity contents in the gas discharged from the first gas phase pipeline 3 are analyzed, and the propylene and impurity contents (main impurities are Dichloropropane (DCP)) in the gas discharged from the second gas phase pipeline 4 are analyzed. The comprehensive analysis result shows that the chloropropanol content in the reaction liquid is 3.52 wt%, the DCP content is 0.022 wt%, the PCE content is 0.010 wt% and the chloropropanone content is 0.010 wt%.
Examples 3 to 6
The procedure was as in example 2, and the aeration time was as shown in Table 1. The results of the analysis of the reaction mass are shown in Table 1. Controlling the gas introduction time.
TABLE 1
Note: the impurity/chloropropanol (mass percent of dichloropropane in the reaction liquid, mass percent of dichlorodiisopropyl ether and mass percent of chloropropanone) in the reaction liquid.
Comparative examples 1 to 3
As shown in FIG. 3, the reaction apparatus was a 1000ml four-necked round-bottomed glass flask, the total volume of the reaction solution was 800ml, and hot water was introduced to control the reaction temperature to 50 ℃. The reaction flask was equipped with mechanical stirring at 100 rpm.
Chlorine gas was fed to the reaction solution through a pipe at a rate of 52ml/min (2.3mmol/min), and propylene was fed to the reaction solution through a pipe at a rate of 62ml/min (2.7 mmol/h).
The gas phase is removed from the gas phase space of the reaction bottle and is absorbed by alkali liquor and ethyl acetate.
The chloropropanol and impurity contents in the reaction material are analyzed, and the chlorine, propylene and impurity contents (main impurity is Dichloropropane (DCP)) in the gas phase removed from the reaction bottle are analyzed. The analytical results are shown in Table 2.
TABLE 2
Note: the impurity/chloropropanol (mass percent of dichloropropane in the reaction liquid, mass percent of dichlorodiisopropyl ether and mass percent of chloropropanone) in the reaction liquid.
As can be seen from the comparative example, with the reaction apparatus of the present invention, by providing two separate gas phase spaces, the contact reaction of the undissolved chlorine and olefin in the gas phase space is reduced or even avoided, and the reaction by-products are reduced by about 7 times.
The embodiments of the present invention have been described above. However, the present invention is not limited to the above embodiment. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A chlorohydrination reaction device is characterized by comprising a hypochlorous acid reaction area and a chlorohydrination reaction area, wherein the two reaction areas comprise gas-phase areas, and the gas-phase areas are independent from each other and are used for containing unreacted reaction gas in the reaction areas;
wherein "independent from each other" means that the gases in the two gas phase zones are each independently present and do not contact each other.
2. The chlorohydrination reaction apparatus of claim 1, wherein the hypochlorous acid reaction zone and the chlorohydrination reaction zone each further comprise a solution zone, and the solution zone of the hypochlorous acid reaction zone is designated as a first solution zone and the solution zone of the chlorohydrination reaction zone is designated as a second solution zone.
Preferably, the gas phase zone is located above the solution zone in each reaction zone.
3. The chlorohydrination reaction apparatus of claim 1 or 2, wherein the first solution zone and the second solution zone are in communication or not, preferably are in communication. For example, the hypochlorous acid reaction zone and the chlorohydrination reaction zone are connected by a pipeline to communicate the solution zone.
Preferably, a first communicating line is provided at the bottom of the hypochlorous acid reaction zone and the chlorohydrination reaction zone to communicate the first solution zone and the second solution zone.
Preferably, a second communication line is provided in the middle upper part of the hypochlorous acid reaction zone and the middle upper part of the chlorohydrination reaction zone to realize circulation of the liquid in the first solution zone and the second solution zone.
Preferably, a liquid delivery device is provided on any of the communication lines described above. Preferably, the liquid delivery device is a pump.
4. The chlorohydrination reaction apparatus of any one of claims 1-3, wherein the gas phase zone of the hypochlorous acid reaction zone is designated as a first gas phase zone for containing unreacted chlorine gas, and the gas phase zone of the chlorohydrination reaction zone is designated as a second gas phase zone for containing unreacted olefin.
Preferably, the first gas phase area and the first solution area are connected, and the second gas phase area and the second solution area are connected, and the connection position is the solution liquid level.
5. The chlorohydrination reaction apparatus of any one of claims 1-4, wherein the reaction apparatus includes a line for introducing chlorine gas, the gas outlet of the line for introducing chlorine gas being disposed in the first solution zone.
Preferably, the reaction apparatus further comprises a first gas phase line connected to the first gas phase zone for discharge of unreacted chlorine gas.
Preferably, the first gas phase pipeline is connected with a pipeline for introducing chlorine gas, and the chlorine gas extracted from the first gas phase zone is recycled as raw gas. Preferably, a pressure-increasing device is provided in the connecting line between the first gas phase line and the chlorine gas introduction line. For example, the pressure boosting device is a compressor or a fan.
6. The chlorohydrination reaction apparatus according to any one of claims 1 to 5, further comprising at least one line for introducing olefin, the gas outlet of the line for introducing olefin being located at least in the second solution zone, preferably in the middle-lower part of the second solution zone.
Preferably, when the olefin introducing line is two, the gas outlet of one olefin introducing line is disposed in the second solution zone (preferably, in the middle-lower portion of the second solution zone), and the other olefin introducing line is disposed in the middle-lower portion of the first solution zone (preferably, opposite to the chlorine introducing line).
Preferably, the reaction apparatus further comprises a second gas phase line connected to the second gas phase zone for discharging unreacted olefins.
Preferably, the second gas phase line is connected to an olefin introduction line communicating with the second solution zone, and the gas phase withdrawn from the second gas phase zone is recycled as a raw material gas. Preferably, a pressurizing means is provided on a connecting line of the second gas phase line and the olefin introducing line communicating with the second solution zone. For example, the pressure boosting device is a compressor or a fan.
7. The chlorohydrination reaction apparatus of any one of claims 1-6, further comprising a process water line for supplementing water required for the reaction in each reaction zone. Preferably, the process water lines are connected to the respective gas phase zones.
Preferably, the hypochlorous acid reaction area and the chlorohydrination reaction area further comprise an insulating layer. Preferably, the insulating layer covers at least the solution zone.
Preferably, the reaction device further comprises a reaction liquid outflow line, and the reaction liquid outflow line is connected with the second solution zone, and is preferably positioned at the upper part of the second solution zone.
Preferably, the reaction device further comprises a stirrer, and the stirrer is used for stirring the materials in the solution area of each reaction area.
8. Use of a chlorohydrination reaction apparatus as claimed in any one of claims 1 to 7 in the production of chlorohydrin and/or in the production of propylene oxide.
9. A method for preparing chlorohydrin, comprising the steps of: chlorine and an olefin are reacted in a chlorohydrination reaction apparatus as described in any one of claims 1 to 7 to produce a chlorohydrin.
10. The method of claim 9, comprising the steps of: introducing chlorine into the first solution zone, contacting chlorine with water, then carrying out dissolution reaction to generate hypochlorous acid and HCl, and allowing undissolved chlorine to enter the first gas phase zone; the second solution zone is fed with an olefin, the olefin is reacted with the aqueous hypochlorous acid solution from the first solution zone in the second solution zone to produce a chlorohydrin, and the unreacted olefin is introduced into the second vapor phase zone.
Preferably, the olefin is ethylene, propylene, chloropropene or butene.
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