CN115521197B - Concentration method of 3-hydroxy propanal aqueous solution - Google Patents
Concentration method of 3-hydroxy propanal aqueous solution Download PDFInfo
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- CN115521197B CN115521197B CN202211336841.0A CN202211336841A CN115521197B CN 115521197 B CN115521197 B CN 115521197B CN 202211336841 A CN202211336841 A CN 202211336841A CN 115521197 B CN115521197 B CN 115521197B
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Abstract
The application provides a method for concentrating a 3-hydroxy-propionaldehyde aqueous solution. The concentration method comprises the following steps: carrying out first concentration on the 3-hydroxy-propanal aqueous solution through a first-stage reverse osmosis membrane to obtain first-stage reverse osmosis produced water and first-stage reverse osmosis concentrated water; the concentrated water of the first-stage reverse osmosis is used for hydrogenation reaction; carrying out second concentration on the water produced by the first-stage reverse osmosis through a second-stage reverse osmosis membrane to obtain water produced by the second-stage reverse osmosis and concentrated water of the second-stage reverse osmosis; the concentrated water of the second-stage reverse osmosis returns to the first-stage reverse osmosis membrane again to carry out first concentration; and so on until the produced water of the second-stage reverse osmosis is subjected to N concentration through the N-stage reverse osmosis membrane, obtaining the produced water of the N-stage reverse osmosis and the concentrated water of the N-stage reverse osmosis, and returning the concentrated water of the N-stage reverse osmosis to the N-1-stage reverse osmosis membrane for N-1-time concentration; n is more than or equal to 2; wherein the pore diameters of the first-level reverse osmosis membrane and the second-level reverse osmosis membrane up to the N-level reverse osmosis membrane are independently distributed at 0.1-1 nm.
Description
Technical Field
The application relates to the technical field of chemical separation, in particular to a concentration method of a 3-hydroxy-propanal aqueous solution.
Background
1, 3-propanediol (1, 3-PDO) is an important organic chemical raw material, can be applied to the industries of printing ink, paint, cosmetics, pharmacy, antifreezing agent and the like, and particularly has wide market prospect as a key polymerization monomer for producing polytrimethylene terephthalate (PTT) fibers with huge market potential. The Acrolein (ACR) hydration hydrogenation route is one of important routes for preparing 1, 3-propanediol, and has the characteristics of wide raw material sources, mild process conditions, controllable cost and the like.
Under the action of acid catalyst, acrolein and water are hydrated to produce 3-hydroxy propanal. Since the reaction is a reversible exothermic reaction and the acrolein as the raw material and the 3-hydroxypropanal (3-HPA) produced are relatively active and are susceptible to side reactions such as self-polymerization or polycondensation, the conversion rate of Acrolein (ACR) is controlled to about 50% by using a low concentration of acrolein-hydrated raw material (10 wt% to 16 wt%) and mild reaction conditions (hydration reaction temperature 40 to 50 ℃) in order to obtain a high product selectivity. The unreacted acrolein raw material in the hydration reaction liquid is recovered, the concentration of the remaining 3-hydroxy propanal aqueous solution (8-15 wt%) is lower, the productivity of the subsequent hydrogenation reaction is severely limited, and meanwhile, the concentration of 1,3-PDO in the hydrogenation liquid obtained by taking the low-concentration 3-hydroxy propanal aqueous solution as the raw material is lower, so that the energy consumption of the subsequent 1,3-PDO dehydration concentration process is high, and the retention time of the material in a high-temperature area is long.
Generally, the capacity can be increased by increasing the feeding speed, the reaction temperature and the reaction rate or increasing the concentration of reactants through an enlarged reaction device, but hydrogenation reaction belongs to gas-liquid-solid three-phase catalysis and requires high-temperature and high-pressure operation conditions, so that the material requirements on a reaction kettle are more severe due to the enlargement of the device, and the complexity of the device and the difficulty of an operation technology are greatly increased; the reaction temperature is increased, the 3-hydroxy-propionaldehyde and the 1, 3-propanediol are easy to generate side reaction at high temperature, and impurities which are difficult to separate are generated, so that the subsequent separation difficulty is increased; the concentration of the reactant is improved without modifying the device, side reactions are not increased, the concentration of the 1,3-PDO generated by the hydrogenation reaction is high, the dehydration concentration energy consumption is low, the residence time in a high-temperature area is short, the impurity generation is less, and the method is the most economical and reasonable technical scheme in view of combination.
In order to increase the concentration of the 3-HPA aqueous solution and thus enlarge the productivity, water in the 3-hydroxy-propionaldehyde aqueous solution is usually separated by adopting a rectification or flash evaporation method, but the heating temperature of a tower kettle is high, the 3-hydroxy-propionaldehyde has poor stability, reversible side reaction can occur to generate acrolein, further reaction is carried out to generate 4-hetero-oxo-heptanediol, the balance rate of the 3-hydroxy-propionaldehyde in the separation process is low, and alcohol impurities are generated in the subsequent hydrogenation reaction. Thus, the rectification or flash distillation process is not suitable for concentrating aqueous 3-hydroxypropanal solutions.
Disclosure of Invention
The application mainly aims to provide a concentration method of a 3-hydroxy-propionic aldehyde aqueous solution, which aims to solve the problems of low efficiency, long residence time and high energy consumption of the method for concentrating the 3-hydroxy-propionic aldehyde aqueous solution in the prior art.
In order to achieve the above object, according to one aspect of the present application, there is provided a method for concentrating an aqueous solution of 3-hydroxypropanal, the method comprising: step S1, carrying out first concentration on a 3-hydroxy-propionaldehyde aqueous solution through a first-stage reverse osmosis membrane to obtain first-stage reverse osmosis produced water and first-stage reverse osmosis concentrated water; the concentrated water of the first-stage reverse osmosis is used for hydrogenation reaction; s2, carrying out second concentration on the water produced by the first-stage reverse osmosis through a second-stage reverse osmosis membrane to obtain water produced by the second-stage reverse osmosis and concentrated water of the second-stage reverse osmosis; the concentrated water of the second-stage reverse osmosis returns to the first-stage reverse osmosis membrane again to carry out first concentration; step S3, analogizing is performed sequentially until the produced water of the second-stage reverse osmosis is subjected to N concentration through an N-stage reverse osmosis membrane to obtain the produced water of the N-stage reverse osmosis and the concentrated water of the N-stage reverse osmosis, and the concentrated water of the N-stage reverse osmosis is returned to the N-1-stage reverse osmosis membrane to be subjected to N-1 concentration; n is more than or equal to 2; the pore diameters of the first-level reverse osmosis membrane and the second-level reverse osmosis membrane up to the N-level reverse osmosis membrane are respectively and independently distributed at 0.1-1 nm.
Further, the structure types of the primary reverse osmosis membrane, the secondary reverse osmosis membrane and the N-stage reverse osmosis membrane are each independently selected from any one of hollow fiber type, roll type, plate frame type and tube type, and are preferably tube type.
Further, the materials of the first-stage reverse osmosis membrane and the second-stage reverse osmosis membrane up to the N-stage reverse osmosis membrane are polyamide and/or cellulose acetate independently, and polyamide is preferable.
Further, the temperature of the first concentration and the second concentration to the Nth concentration is 5-45 ℃ respectively and independently; preferably, the pressure of the first concentration up to the nth concentration is sequentially reduced, preferably the pressure of the first concentration is 5 to 10MPa, preferably the pressure of the second concentration is 1 to 6MPa, preferably the pressure of the nth concentration is 0.2 to 1MPa.
Further, in step S1, the mass concentration of the aqueous solution of 3-hydroxypropanal is 5 to 10%.
Further, in the step S1, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the first-stage reverse osmosis is 15-50%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the first-stage reverse osmosis is preferably 1-5%.
Further, in the step S2, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the second-stage reverse osmosis is 5-10%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the second-stage reverse osmosis is 0.5-1%.
Further, the mass concentration of 3-hydroxy-propionaldehyde in the water produced by N-level reverse osmosis is less than or equal to 0.1 percent.
Further, in the concentration method, the single pass interception rate of 3-hydroxy propanal is 60-90% when concentration is carried out through the first-stage reverse osmosis membrane.
Further, in the concentration method, after N-level reverse osmosis membrane is used for N concentration, the total retention rate of 3-hydroxy-propanal is more than or equal to 99 percent.
By applying the technical scheme of the application, the separation characteristic of the reverse osmosis membrane is utilized to intercept the 3-hydroxy-propionaldehyde with relatively large molecular weight in the 3-hydroxy-propionaldehyde solution, and the water molecules with small molecular weight are discharged, so that the 3-hydroxy-propionaldehyde concentrate is obtained, and the interception rate and the separation effect of the 3-HPA are improved. The 3-hydroxy propanal concentrate is used as the raw material for preparing the 1,3-PDO through hydrogenation reaction, so that the productivity can be increased, the concentration of the 1,3-PDO prepared through hydrogenation is high, the energy consumption for dehydration and concentration is reduced, impurities generated due to the fact that materials stay in a high-temperature area for a long time in the traditional rectification and concentration process are avoided, the purity of the dehydrated 1,3-PDO crude product is high, the subsequent 1,3-PDO purification cost is saved, and the separation difficulty of the 1,3-PDO is reduced.
Drawings
The accompanying drawings, which are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate embodiments of the application and together with the description serve to explain the application. In the drawings:
fig. 1 shows a schematic flow chart of the concentration method of the present application.
Detailed Description
It should be noted that, without conflict, the embodiments of the present application and features of the embodiments may be combined with each other. The application will be described in detail below with reference to the drawings in connection with embodiments.
As analyzed by the background art, the concentration of the 3-HPA solution synthesized by hydration reaction of acrolein and water in the prior art is low, which limits the productivity of the subsequent hydrogenation reaction; and the concentration of the 1,3-PDO obtained by taking the low-concentration 3-HPA aqueous solution as the raw material is lower, so that the energy consumption of the subsequent 1,3-PDO dehydration and concentration process is higher, and meanwhile, the retention time of the material in a high-temperature area is long.
In order to increase the concentration of the 3-HPA aqueous solution and thus the productivity, the reaction device can be enlarged, the reaction temperature can be increased to accelerate the reaction rate or the concentration of reactants can be increased, but the hydrogenation reaction belongs to gas-liquid-solid three-phase catalysis and requires high-temperature and high-pressure operation conditions, so that the material requirements on the reaction kettle can be more severe due to the enlargement of the device, and the complexity of the device and the difficulty of the operation technology are greatly increased; the reaction temperature is increased, and the 3-hydroxy propanal and the 1, 3-propanediol are easy to generate side reaction at high temperature, so that impurities which are difficult to separate are generated, and the subsequent separation difficulty is increased.
Or separating 3-hydroxy propanal from water by rectification or flash evaporation in the process, thereby expanding the productivity. However, the tower kettle has high heating temperature and poor stability of 3-hydroxy-propionaldehyde, can generate reversible side reaction to generate acrolein, further react to generate 4-hetero-oxo-heptanediol, so that the 3-hydroxy-propionaldehyde balance rate in the separation process is low, and alcohol impurities are generated in the subsequent hydrogenation reaction.
In summary, the method for concentrating the 3-hydroxy-propionic aldehyde aqueous solution in the prior art has the problems of low efficiency, long residence time and high energy consumption of the method for concentrating the 3-hydroxy-propionic aldehyde aqueous solution. In order to solve the problems, the application provides a method for concentrating a 3-hydroxy-propanal aqueous solution.
Membrane separation is currently the most widespread low concentration particle separation method. Mainly comprises a reverse osmosis membrane separation method, an ultrafiltration separation method and a nanofiltration separation method. When the stock solution flows through the surface of the membrane under a certain pressure, a plurality of tiny micropores densely distributed on the surface of the membrane only allow water and organic micromolecular substances to pass through to become permeate, and substances with the volume larger than the pore diameter of the micropores on the surface of the membrane in the stock solution are trapped on the liquid inlet side of the membrane to become concentrated solution, so that the separation and concentration of the stock solution are realized.
In an exemplary embodiment of the present application, there is provided a method for concentrating an aqueous solution of 3-hydroxypropanal, as shown in FIG. 1, comprising: step S1, carrying out first concentration on a 3-hydroxy-propionaldehyde aqueous solution through a first-stage reverse osmosis membrane to obtain first-stage reverse osmosis produced water and first-stage reverse osmosis concentrated water; the concentrated water of the first-stage reverse osmosis is used for hydrogenation reaction; s2, carrying out second concentration on the water produced by the first-stage reverse osmosis through a second-stage reverse osmosis membrane to obtain water produced by the second-stage reverse osmosis and concentrated water of the second-stage reverse osmosis; the concentrated water of the second-stage reverse osmosis returns to the first-stage reverse osmosis membrane again to carry out first concentration; step S3, analogizing in sequence until the produced water of the second-stage reverse osmosis is subjected to N concentration through an N-stage reverse osmosis membrane to obtain the produced water of the N-stage reverse osmosis and the concentrated water of the N-stage reverse osmosis, and returning the concentrated water of the N-stage reverse osmosis to the N-1-stage reverse osmosis membrane to perform N-1-time concentration; wherein N is more than or equal to 2; wherein the pore diameters of the first-level reverse osmosis membrane and the second-level reverse osmosis membrane up to the N-level reverse osmosis membrane are respectively and independently distributed at 0.1-1 nm.
According to the application, by utilizing the separation characteristic of the reverse osmosis membrane, relatively large molecular weight 3-hydroxy-propionaldehyde in the 3-hydroxy-propionaldehyde solution is intercepted, and small molecular weight water molecules are discharged, so that 3-hydroxy-propionaldehyde concentrate is obtained, and the 3-HPA interception rate and separation effect are improved. The 3-hydroxy propanal concentrate is used as the raw material for preparing the 1,3-PDO through hydrogenation reaction, so that the productivity can be increased, the concentration of the 1,3-PDO prepared through hydrogenation is high, the energy consumption for dehydration and concentration of the 1,3-PDO is reduced, impurities generated due to the fact that materials stay in a high-temperature area for a long time in the traditional rectification and concentration process are avoided, the purity of a dehydrated 1,3-PDO crude product is high, the subsequent 1,3-PDO concentration and purification cost is saved, and the separation difficulty of the 1,3-PDO is reduced.
The concentration method has higher retention rate of 3-HPA, reduces the residual content of 3-HPA in the reverse osmosis produced water, can directly use the reverse osmosis produced water as the raw material of ACR hydration reaction, reduces the discharge amount of waste water and saves the cost of three-waste treatment. The method has the advantages of high concentration efficiency, low energy consumption, stable and reliable treatment effect, convenient industrialized implementation and obvious economic benefit.
The application adopts a reverse osmosis membrane separation method to concentrate the 3-hydroxy-propionaldehyde aqueous solution, the separation process is unnecessary to heat, the separation of 3-hydroxy-propionaldehyde and water can be realized under the normal temperature condition, the side reaction impurities generated due to high temperature in the separation process are avoided, the active 3-HPA is prevented from polymerization or polycondensation, and the reaction balance rate in the separation process is more than 99.5 percent.
The application adopts the reverse osmosis membrane separation method to concentrate the 3-hydroxy propanal aqueous solution, and has the advantages of high efficiency, short time consumption and low energy consumption. Meanwhile, the device has the advantages of simple equipment, convenient operation, continuous operation, serial connection of devices, high automation degree and the like. Under the condition of not changing a hydrogenation device, the hydrogenation reaction productivity is greatly improved, and the equipment investment is saved.
In some embodiments, to maximize efficiency and reduce energy consumption, it is preferred that N be 2, 3, 4, 5 stages.
In order to discharge the water molecules of the 3-hydroxy-propionaldehyde aqueous solution as much as possible, the first-stage reverse osmosis membrane and the second-stage reverse osmosis membrane can be reverse osmosis membranes with the same structure type and material as the N-stage reverse osmosis membrane, and reverse osmosis membranes with different structure types and materials can also be adopted. In some embodiments, the structure types of the primary reverse osmosis membrane, the secondary reverse osmosis membrane and the N-stage reverse osmosis membrane comprise any one of hollow fiber type, coiled type, plate frame type and tubular type, preferably tubular type, and the materials of the primary reverse osmosis membrane, the secondary reverse osmosis membrane and the N-stage reverse osmosis membrane comprise polyamide and/or cellulose acetate, preferably polyamide.
Those skilled in the art will appreciate that the rejection capability of a reverse osmosis membrane for different substances depends on the nature (material, structure, configuration, etc.) of the membrane itself and the nature (molecular size, molecular configuration, molecular polarity, etc.) of the substance to be trapped, and the rejection effect of the reverse osmosis membrane for the target molecules under different conditions can be determined through experiments, so as to find a reverse osmosis membrane with higher rejection rate for the target molecules. The type of the reverse osmosis membrane is not particularly limited in the present application, as long as the purpose of separating water from 3-hydroxypropanal can be achieved. In some embodiments, the primary reverse osmosis membrane, the secondary reverse osmosis membrane, and up to the N-stage reverse osmosis membrane are each independently tubular membranes of a polyethylene amide material. The tubular membrane made of the polyethylene amide material has high chemical resistance, and the membrane material is not easy to damage in the separation process.
The temperature of concentration is not particularly limited in the present application. In some embodiments, the temperature of the first concentrate, the second concentrate, and the nth concentrate are each independently 5 to 45 ℃. And introducing condensed water in the reaction process to maintain the constant temperature condition.
The reverse osmosis membrane separation method is to apply a pressure higher than the natural osmotic pressure on one side of the treatment liquid, twist the natural osmotic direction, and separate the water pressure in the concentrated liquid to the other side of the semipermeable membrane. In order to separate water and 3-HPA in the aqueous 3-HPA solution as efficiently as possible, in some embodiments, the pressure of the first concentrate until the Nth concentrate is sequentially reduced, preferably the pressure of the first concentrate is 5 to 10MPa, preferably the pressure of the second concentrate is 1 to 6MPa, preferably the pressure of the Nth concentrate is 0.2 to 1MPa. The higher the concentration of 3-HPA in the aqueous solution, the higher the pressure required for concentration and the lower the rejection. The concentration of the 3-HPA aqueous solution in the produced water is reduced in sequence every time the 3-HPA aqueous solution is concentrated and separated by a first-stage reverse osmosis membrane. To increase the rejection, the pressure of each stage of concentration is correspondingly reduced.
In order to ensure the selectivity of the hydrogenation reaction and the conversion of the raw material and to simulate the actual production process, in some embodiments, the mass concentration of the aqueous solution of 3-hydroxypropanal in step S1 is 5 to 10% by weight.
In some embodiments, in step S1, the mass concentration of 3-hydroxypropanal in the concentrated water of the first stage reverse osmosis is 15 to 50 weight percent, preferably the mass concentration of 3-hydroxypropanal in the produced water of the first stage reverse osmosis is 1 to 5 weight percent. The mass concentration of the 3-hydroxy propanal in the concentrated water of the first-stage reverse osmosis reaches the concentration of directly carrying out hydrogenation reaction, so that the concentrated water of the first-stage reverse osmosis can be directly used for hydrogenation reaction.
After the second concentration, the 3-HPA in the water produced by the first-stage reverse osmosis is further concentrated. In some embodiments, in step S2, the mass concentration of 3-hydroxypropanal in the concentrated water of the second stage reverse osmosis is 5 to 10wt%, and the mass concentration of 3-hydroxypropanal in the produced water of the second stage reverse osmosis is 0.5 to 1wt%. The concentration of 3-HPA in the concentrated water of the second-stage reverse osmosis is low and does not reach the standard of directly carrying out hydrogenation reaction, so that the concentrated water of the second-stage reverse osmosis is used as the raw material of the first concentration to be continuously concentrated and concentrated.
Through N concentration, 3-HPA in the N-stage reverse osmosis produced water is further reduced. In some embodiments, the mass concentration of 3-hydroxypropanal in the produced water of the N-stage reverse osmosis is less than or equal to 0.1%.
In some embodiments, the single pass rejection of 3-hydroxypropanal is 60 to 90% per concentration by the first stage reverse osmosis membrane, preferably the total rejection of 3-hydroxypropanal is greater than or equal to 99% after the nth concentration by the N-stage reverse osmosis membrane. By adopting the concentration method, the single-pass retention rate of the 3-HPA is higher, and the retention rate of the 3-HPA after N-level concentration can reach more than 99 percent.
The application is described in further detail below in connection with specific examples which are not to be construed as limiting the scope of the application as claimed.
Example 1
(1) Carrying out first concentration on a 3-HPA water solution raw material (the mass concentration is 5%) through a first-stage reverse osmosis membrane (SW 30-4040) to obtain first-stage reverse osmosis produced water and first-stage reverse osmosis concentrated water; the operation temperature of the first concentration is 5 ℃, the operation pressure of the first concentration is 5MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the first-stage reverse osmosis is 15%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the first-stage reverse osmosis is 1%;
(2) Extracting the concentrated water of the first-stage reverse osmosis in the step (1) for subsequent hydrogenation reaction to produce 1,3-PDO; carrying out second concentration on the water produced by the first-stage reverse osmosis in the step (1) through a second-stage reverse osmosis membrane (SW 30-4040) to obtain water produced by the second-stage reverse osmosis and concentrated water of the second-stage reverse osmosis; the second concentration operation temperature is 5 ℃, the second concentration operation pressure is 1MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the second-stage reverse osmosis is 5%, and the mass concentration of 3-hydroxy-propionaldehyde in the product water of the second-stage reverse osmosis is 0.090wt%.
Example 2
(1) Carrying out first concentration on a 3-HPA aqueous solution raw material (the mass concentration is 7%) through a first-stage reverse osmosis membrane (SW 30-4040) to obtain first-stage reverse osmosis produced water and first-stage reverse osmosis concentrated water; the operation temperature of the first concentration is 25 ℃, the operation pressure of the first concentration is 8MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the first-stage reverse osmosis is 21%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the first-stage reverse osmosis is 2.5%;
(2) Extracting the concentrated water of the first-stage reverse osmosis in the step (1) for subsequent hydrogenation reaction to produce 1,3-PDO; carrying out second concentration on the water produced by the first-stage reverse osmosis in the step (1) through a second-stage reverse osmosis membrane to obtain water produced by the second-stage reverse osmosis and concentrated water of the second-stage reverse osmosis; the second concentration operation temperature is 25 ℃, the second concentration operation pressure is 4MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the second-stage reverse osmosis is 7%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the second-stage reverse osmosis is 0.6%;
(3) Extracting the concentrated water of the second-stage reverse osmosis in the step (2) to be used as a raw material for concentrating the first-stage reverse osmosis membrane; thirdly concentrating the water produced by the second-stage reverse osmosis in the step (2) through a third-stage reverse osmosis membrane (SW 30-4040) to obtain water produced by the third-stage reverse osmosis and concentrated water of the third-stage reverse osmosis; the third concentration operation temperature is 25 ℃, the third concentration operation pressure is 0.5MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the third-stage reverse osmosis is 2.5%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the third-stage reverse osmosis is 0.070%.
Example 3
(1) Carrying out first concentration on a 3-HPA water solution raw material (the mass concentration is 8 percent) through a first-stage reverse osmosis membrane (SW 30-4040) to obtain first-stage reverse osmosis produced water and first-stage reverse osmosis concentrated water; the operation temperature of the first concentration is 25 ℃, the operation pressure of the first concentration is 8MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the first-stage reverse osmosis is 22%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the first-stage reverse osmosis is 3%;
(2) Extracting the concentrated water of the first-stage reverse osmosis in the step (1) for subsequent hydrogenation reaction to produce 1,3-PDO; carrying out second concentration on the water produced by the first-stage reverse osmosis in the step (1) through a second-stage reverse osmosis membrane (SW 30-4040) to obtain water produced by the second-stage reverse osmosis and concentrated water of the second-stage reverse osmosis; the second concentration operation temperature is 25 ℃, the second concentration operation pressure is 4MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the second-stage reverse osmosis is 8%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the second-stage reverse osmosis is 0.7%;
(3) Extracting the concentrated water of the second-stage reverse osmosis in the step (2) to be used as a raw material for concentrating the first-stage reverse osmosis membrane; thirdly concentrating the water produced by the second-stage reverse osmosis in the step (1) through a third-stage reverse osmosis membrane (SW 30-4040) to obtain water produced by the third-stage reverse osmosis and concentrated water of the third-stage reverse osmosis; the operation temperature of the third concentration is 25 ℃, the operation pressure of the third concentration is 2MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the second-stage reverse osmosis is 3%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the second-stage reverse osmosis is 0.1%;
(4) Extracting the concentrated water of the third-stage reverse osmosis in the step (3) to be used as a raw material for concentrating the second-stage reverse osmosis membrane; carrying out fourth concentration on the water produced by the third-stage reverse osmosis in the step (3) through a fourth-stage reverse osmosis membrane (SW 30-4040) to obtain water produced by the fourth-stage reverse osmosis and concentrated water of the fourth-stage reverse osmosis; the fourth concentration operation temperature is 25 ℃, the fourth concentration operation pressure is 0.5MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the four-stage reverse osmosis is 0.7%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the four-stage reverse osmosis is 0.050%.
Example 4
(1) Carrying out first concentration on a 3-HPA aqueous solution raw material (the mass concentration is 10 percent) through a first-stage reverse osmosis membrane (SW 30-4040) to obtain first-stage reverse osmosis produced water and first-stage reverse osmosis concentrated water; the operation temperature of the first concentration is 45 ℃, the operation pressure of the first concentration is 10MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the first-stage reverse osmosis is 50%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the first-stage reverse osmosis is 5%;
(2) Extracting the concentrated water of the first-stage reverse osmosis in the step (1) for subsequent hydrogenation reaction to produce 1,3-PDO; carrying out second concentration on the water produced by the first-stage reverse osmosis in the step (1) through a second-stage reverse osmosis membrane (SW 30-4040) to obtain water produced by the second-stage reverse osmosis and concentrated water of the second-stage reverse osmosis; the second concentration operation temperature is 45 ℃, the second concentration operation pressure is 6MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the second-stage reverse osmosis is 10%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the second-stage reverse osmosis is 1%;
(3) Extracting the concentrated water of the second-stage reverse osmosis in the step (2) to be used as a raw material for concentrating the first-stage reverse osmosis membrane; thirdly concentrating the water produced by the second-stage reverse osmosis in the step (2) through a third-stage reverse osmosis membrane (SW 30-4040) to obtain water produced by the third-stage reverse osmosis and concentrated water of the third-stage reverse osmosis; the operation temperature of the third concentration is 25 ℃, the operation pressure of the third concentration is 2MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the third-stage permeation is 5%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the third-stage permeation is 0.1%;
(4) Extracting the concentrated water of the third-stage reverse osmosis in the step (3) to be used as a raw material for concentrating the second-stage reverse osmosis membrane; carrying out fourth concentration on the water produced by the third-stage reverse osmosis in the step (3) through a fourth-stage reverse osmosis membrane (SW 30-4040) to obtain water produced by the fourth-stage reverse osmosis and concentrated water of the fourth-stage reverse osmosis; the fourth concentration operation temperature is 25 ℃, the fourth concentration operation pressure is 0.5MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the fourth-stage reverse osmosis is 1wt%, and the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the fourth-stage reverse osmosis is 0.01wt%;
(5) Extracting the concentrated water of the four-stage reverse osmosis in the step (4) to be used as a raw material for concentrating the three-stage reverse osmosis membrane; carrying out fifth concentration on the water produced by the four-stage reverse osmosis in the step (3) through a five-stage reverse osmosis membrane (SW 30-4040) to obtain water produced by the five-stage reverse osmosis and concentrated water of the five-stage reverse osmosis; the operation temperature of the fifth concentration is 25 ℃, the operation pressure of the fifth concentration is 0.5MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the fifth-stage reverse osmosis is 0.1%, and the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the fifth-stage reverse osmosis is 0.005%.
Example 5
(1) Carrying out first concentration on a 3-HPA aqueous solution raw material (the mass concentration is 7%) through a first-stage reverse osmosis membrane (SW 30-2540) to obtain first-stage reverse osmosis produced water and first-stage reverse osmosis concentrated water; the operation temperature of the first concentration is 45 ℃, the operation pressure of the first concentration is 5MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the first-stage reverse osmosis is 18%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the first-stage reverse osmosis is 1.1%;
(2) Extracting the concentrated water of the first-stage reverse osmosis in the step (1) for subsequent hydrogenation reaction to produce 1,3-PDO; carrying out second concentration on the water produced by the first-stage reverse osmosis in the step (1) through a second-stage reverse osmosis membrane (SW 30-2540) to obtain water produced by the second-stage reverse osmosis and concentrated water of the second-stage reverse osmosis; the second concentration operation temperature is 25 ℃, the second concentration operation pressure is 1MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the second-stage reverse osmosis is 7.7%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the second-stage reverse osmosis is 0.18%;
(3) Extracting the concentrated water of the second-stage reverse osmosis in the step (2) to be used as a raw material for concentrating the first-stage reverse osmosis membrane; thirdly concentrating the water produced by the second-stage reverse osmosis in the step (2) through a third-stage reverse osmosis membrane (SW 30-2540) to obtain water produced by the third-stage reverse osmosis and concentrated water of the third-stage reverse osmosis; the third concentration operation temperature is 25 ℃, the third concentration operation pressure is 0.2MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the third-stage reverse osmosis is 1.1%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the third-stage reverse osmosis is 0.018%.
Example 6
(1) Carrying out first concentration on a 3-HPA aqueous solution raw material (the mass concentration is 7%) through a first-stage reverse osmosis membrane (SW 30-4040) to obtain first-stage reverse osmosis produced water and first-stage reverse osmosis concentrated water; the operation temperature of the first concentration is 5 ℃, the operation pressure of the first concentration is 10MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the first-stage reverse osmosis is 48%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the first-stage reverse osmosis is 2.8%;
(2) Extracting the concentrated water of the first-stage reverse osmosis in the step (1) for subsequent hydrogenation reaction to produce 1,3-PDO; carrying out second concentration on the water produced by the first-stage reverse osmosis in the step (1) through a second-stage reverse osmosis membrane (SW 30-4040) to obtain water produced by the second-stage reverse osmosis and concentrated water of the second-stage reverse osmosis; the second concentration operation temperature is 25 ℃, the second concentration operation pressure is 6MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the second-stage reverse osmosis is 7%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the second-stage reverse osmosis is 0.84%;
(3) Extracting the concentrated water of the second-stage reverse osmosis in the step (2) to be used as a raw material for concentrating the first-stage reverse osmosis membrane; thirdly concentrating the water produced by the second-stage reverse osmosis in the step (2) through a third-stage reverse osmosis membrane (SW 30-4040) to obtain water produced by the third-stage reverse osmosis and concentrated water of the third-stage reverse osmosis; the third concentration operation temperature is 25 ℃, the third concentration operation pressure is 1MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the third-stage reverse osmosis is 0.84%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the third-stage reverse osmosis is 0.093%.
Example 7
(1) Carrying out first concentration on a 3-HPA aqueous solution raw material (the mass concentration is 7%) through a first-stage reverse osmosis membrane (SW 30-4040) to obtain first-stage reverse osmosis produced water and first-stage reverse osmosis concentrated water; the operation temperature of the first concentration is 25 ℃, the operation pressure of the first concentration is 8MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the first-stage reverse osmosis is 21%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the first-stage reverse osmosis is 2.5%;
(2) Extracting the concentrated water of the first-stage reverse osmosis in the step (1) for subsequent hydrogenation reaction to produce 1,3-PDO; carrying out second concentration on the water produced by the first-stage reverse osmosis in the step (1) through a second-stage reverse osmosis membrane (SW 30-4040) to obtain water produced by the second-stage reverse osmosis and concentrated water of the second-stage reverse osmosis; the second concentration operation temperature is 25 ℃, the second concentration operation pressure is 8MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the second-stage reverse osmosis is 7%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the second-stage reverse osmosis is 0.90%;
(3) Extracting the concentrated water of the second-stage reverse osmosis in the step (2) to be used as a raw material for concentrating the first-stage reverse osmosis membrane; thirdly concentrating the water produced by the second-stage reverse osmosis in the step (2) through a third-stage reverse osmosis membrane (SW 30-4040) to obtain water produced by the third-stage reverse osmosis and concentrated water of the third-stage reverse osmosis; the third concentration operation temperature is 25 ℃, the third concentration operation pressure is 8MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the third-stage reverse osmosis is 2.5%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the third-stage reverse osmosis is 0.72%.
Example 8
(1) Carrying out first concentration on a 3-HPA aqueous solution raw material (the mass concentration is 7%) through a first-stage reverse osmosis membrane (SW 30-4040) to obtain first-stage reverse osmosis produced water and first-stage reverse osmosis concentrated water; the operation temperature of the first concentration is 25 ℃, the operation pressure of the first concentration is 12MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the first-stage reverse osmosis is 60%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the first-stage reverse osmosis is 3.5%;
(2) Extracting the concentrated water of the first-stage reverse osmosis in the step (1) for subsequent hydrogenation reaction to produce 1,3-PDO; carrying out second concentration on the water produced by the first-stage reverse osmosis in the step (1) through a second-stage reverse osmosis membrane (SW 30-4040) to obtain water produced by the second-stage reverse osmosis and concentrated water of the second-stage reverse osmosis; the second concentration operation temperature is 25 ℃, the second concentration operation pressure is 8MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the second-stage reverse osmosis is 7%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the second-stage reverse osmosis is 1.4%;
(3) Extracting the concentrated water of the second-stage reverse osmosis in the step (2) to be used as a raw material for concentrating the first-stage reverse osmosis membrane; thirdly concentrating the water produced by the second-stage reverse osmosis in the step (2) through a third-stage reverse osmosis membrane (SW 30-4040) to obtain water produced by the third-stage reverse osmosis and concentrated water of the third-stage reverse osmosis; the third concentration operation temperature is 25 ℃, the third concentration operation pressure is 2MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the third-stage reverse osmosis is 3.5%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the third-stage reverse osmosis is 1.05%.
Example 9
(1) Carrying out first concentration on a 3-HPA aqueous solution raw material (the mass concentration is 12%) through a first-stage reverse osmosis membrane (SW 30-4040) to obtain first-stage reverse osmosis produced water and first-stage reverse osmosis concentrated water; the operation temperature of the first concentration is 25 ℃, the operation pressure of the first concentration is 8MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the first-stage reverse osmosis is 21%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the first-stage reverse osmosis is 3.1%;
(2) Extracting the concentrated water of the first-stage reverse osmosis in the step (1) for subsequent hydrogenation reaction to produce 1,3-PDO; carrying out second concentration on the water produced by the first-stage reverse osmosis in the step (1) through a second-stage reverse osmosis membrane (SW 30-2540) to obtain water produced by the second-stage reverse osmosis and concentrated water of the second-stage reverse osmosis; the second concentration operation temperature is 25 ℃, the second concentration operation pressure is 4MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the second-stage reverse osmosis is 7%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the second-stage reverse osmosis is 0.720%;
(3) Extracting the concentrated water of the second-stage reverse osmosis in the step (2) to be used as a raw material for concentrating the first-stage reverse osmosis membrane; thirdly concentrating the water produced by the second-stage reverse osmosis in the step (2) through a third-stage reverse osmosis membrane to obtain water produced by the third-stage reverse osmosis and concentrated water of the third-stage reverse osmosis; the third concentration is operated at 25 ℃, the third concentration is operated at 0.5MPa, the mass concentration of 3-hydroxy-propionaldehyde in the concentrated water of the third-stage reverse osmosis is 3.1%, and the mass concentration of 3-hydroxy-propionaldehyde in the produced water of the third-stage reverse osmosis is 0.075%.
Comparative example 1
Unlike example 2, comparative example 1 uses a nanomembrane having the same material as example 2 but a pore size distribution of 1.1 to 2 nm.
(1) Carrying out first concentration on a 3-HPA aqueous solution raw material (the mass concentration is 7%) through a first-stage nano film to obtain first-stage produced water and first-stage concentrated water; the operation temperature of the first concentration is 25 ℃, the operation pressure of the first concentration is 8MPa, the mass concentration of 3-hydroxy-propionaldehyde in the first-stage concentrated water is 10%, and the mass concentration of 3-hydroxy-propionaldehyde in the first-stage produced water is 5.6%;
(2) Extracting the first-stage concentrated water in the step (1) for subsequent hydrogenation reaction to produce 1,3-PDO; carrying out second concentration on the primary produced water in the step (1) through a secondary nano membrane to obtain secondary produced water and secondary concentrated water; the second concentration operation temperature is 25 ℃, the second concentration operation pressure is 4MPa, the mass concentration of 3-hydroxy-propionaldehyde in the second-stage concentrated water is 7%, and the mass concentration of 3-hydroxy-propionaldehyde in the second-stage produced water is 4.8%;
(3) Extracting the concentrated water of the second-stage reverse osmosis in the step (2) to be used as a raw material for concentrating the first-stage nano membrane; thirdly concentrating the second-stage produced water in the step (2) through a third-stage nano membrane to obtain third-stage produced water and third-stage concentrated water; the third concentration is operated at 25 ℃, the third concentration is operated at 0.5MPa, the mass concentration of 3-hydroxy-propionaldehyde in the third-stage concentrated water is 5.2%, and the mass concentration of 3-hydroxy-propionaldehyde in the third-stage produced water is 4.3%.
Comparative example 2
The 3-hydroxy-propionaldehyde aqueous solution with the mass concentration of 10% is used as a raw material, a rectification column with the height of 1.0 meter and built-in glass spring filler (5 theoretical plates with the length of 1 meter) is used for carrying out reduced pressure rectification on the 3-HPA aqueous solution, the absolute pressure is 20Kpa, the kettle temperature is 60-70 ℃, the temperature is 50-60 ℃, the reflux ratio is 1:1, part of water is extracted from the top of the tower, and the 3-hydroxy-propionaldehyde concentrated solution after the concentration of the kettle is obtained.
The 3-hydroxy-propionaldehyde concentrated solution after the residue of comparative example 2 was concentrated and the concentrated water of the first reverse osmosis in each example was subjected to liquid chromatography quantitative analysis, and the data are shown in table 1.
TABLE 1
Note that retention = 1-concentration of 3-HPA in produced water/concentration of 3-HPA in raw material.
Comparative example 2 the aqueous 3-hydroxypropanal solution was concentrated by distillation, and the equilibrium rate was significantly lower than in examples 1-9 due to the side reactions of the 3-HPA solution at high temperature.
From the above description, it can be seen that the above embodiments of the present application achieve the following technical effects: according to the application, by utilizing the separation characteristic of the reverse osmosis membrane, relatively large molecular weight 3-hydroxy-propionaldehyde in the 3-hydroxy-propionaldehyde solution is intercepted, and small molecular weight water molecules are discharged, so that 3-hydroxy-propionaldehyde concentrate is obtained, and the 3-HPA interception rate and separation effect are improved. The 3-hydroxy propanal concentrate is used as the raw material for preparing the 1,3-PDO through hydrogenation reaction, so that the productivity can be increased, the concentration of the 1,3-PDO prepared through hydrogenation is high, the energy consumption for dehydration and concentration is reduced, impurities generated due to the fact that materials stay in a high-temperature area for a long time in the traditional rectification and concentration process are avoided, the purity of the dehydrated 1,3-PDO crude product is high, the subsequent 1,3-PDO purification cost is saved, and the separation difficulty of the 1,3-PDO is reduced.
The above description is only of the preferred embodiments of the present application and is not intended to limit the present application, but various modifications and variations can be made to the present application by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present application should be included in the protection scope of the present application.
Claims (13)
1. A method for concentrating an aqueous solution of 3-hydroxypropanal, the method comprising:
step S1, carrying out first concentration on a 3-hydroxy-propionaldehyde aqueous solution through a first-stage reverse osmosis membrane to obtain first-stage reverse osmosis produced water and first-stage reverse osmosis concentrated water; the concentrated water of the first-stage reverse osmosis is used for hydrogenation reaction;
s2, carrying out second concentration on the primary reverse osmosis produced water through a secondary reverse osmosis membrane to obtain secondary reverse osmosis produced water and secondary reverse osmosis concentrated water; the concentrated water of the second-stage reverse osmosis returns to the first-stage reverse osmosis membrane again to carry out first concentration;
step S3, analogizing until the produced water of the second-stage reverse osmosis is subjected to N concentration through an N-stage reverse osmosis membrane, obtaining the produced water of the N-stage reverse osmosis and the concentrated water of the N-stage reverse osmosis, and returning the concentrated water of the N-stage reverse osmosis to the N-1-stage reverse osmosis membrane to perform N-1 concentration; n is more than or equal to 2;
the pore diameters of the primary reverse osmosis membrane and the secondary reverse osmosis membrane up to the N-level reverse osmosis membrane are respectively and independently distributed at 0.1-1 nm;
the pressure of the first concentration is reduced in sequence until the N concentration is achieved, the pressure of the first concentration is 5-10 MPa, the pressure of the second concentration is 1-6 MPa, and the pressure of the N concentration is 0.2-1 MPa.
2. The concentrating method according to claim 1, wherein the structure types of the primary reverse osmosis membrane, the secondary reverse osmosis membrane, and up to the N-stage reverse osmosis membrane are each independently selected from any one of hollow fiber type, roll type, plate frame type, and tube type.
3. The method according to claim 2, wherein the structure types of the primary reverse osmosis membrane, the secondary reverse osmosis membrane, and up to the N-stage reverse osmosis membrane are each independently tubular.
4. The method according to claim 1, wherein the materials of the primary reverse osmosis membrane, the secondary reverse osmosis membrane and the N-stage reverse osmosis membrane are polyamide and/or cellulose acetate independently.
5. The method according to claim 4, wherein the materials of the primary reverse osmosis membrane, the secondary reverse osmosis membrane and the N-stage reverse osmosis membrane are each independently polyamide.
6. The method of claim 1, wherein the temperatures of the first concentration, the second concentration, and the nth concentration are each independently 5 to 45 ℃.
7. The concentration method according to any one of claims 1 to 6, wherein in step S1, the mass concentration of the aqueous 3-hydroxypropanal solution is 5 to 10%.
8. The method according to any one of claims 1 to 6, wherein in step S1, the mass concentration of 3-hydroxypropanal in the concentrated water of the first-stage reverse osmosis is 15 to 50%.
9. The method according to any one of claims 1 to 6, wherein in step S1, the mass concentration of 3-hydroxypropanal in the primary reverse osmosis product water is 1 to 5%.
10. The method according to any one of claims 1 to 6, wherein in step S2, the mass concentration of 3-hydroxypropanal in the concentrated water of the second-stage reverse osmosis is 5 to 10%, and the mass concentration of 3-hydroxypropanal in the produced water of the second-stage reverse osmosis is 0.5 to 1%.
11. The method according to any one of claims 1 to 6, wherein the mass concentration of 3-hydroxypropanal in the produced water of the N-stage reverse osmosis is 0.1% or less.
12. The concentrating process according to any one of claims 1 to 6, wherein in the concentrating process, the single pass rejection of 3-hydroxypropanal is 60 to 90% per concentration by a primary reverse osmosis membrane.
13. The method according to any one of claims 1 to 6, wherein the total rejection rate of 3-hydroxypropanal after the nth concentration by the N-stage reverse osmosis membrane is not less than 99%.
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