CN116041162A - Method for separating and recovering acrolein from product system for preparing 3-hydroxy propanal by hydration of acrolein - Google Patents
Method for separating and recovering acrolein from product system for preparing 3-hydroxy propanal by hydration of acrolein Download PDFInfo
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- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 title claims abstract description 224
- AKXKFZDCRYJKTF-UHFFFAOYSA-N 3-Hydroxypropionaldehyde Chemical compound OCCC=O AKXKFZDCRYJKTF-UHFFFAOYSA-N 0.000 title claims abstract description 56
- 238000000034 method Methods 0.000 title claims abstract description 40
- 238000006703 hydration reaction Methods 0.000 title claims abstract description 34
- 230000036571 hydration Effects 0.000 title claims abstract description 30
- 239000007791 liquid phase Substances 0.000 claims abstract description 57
- 238000011084 recovery Methods 0.000 claims abstract description 55
- 239000012071 phase Substances 0.000 claims abstract description 43
- 238000009833 condensation Methods 0.000 claims abstract 2
- 230000005494 condensation Effects 0.000 claims abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 48
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 42
- 239000012535 impurity Substances 0.000 claims description 35
- 239000010409 thin film Substances 0.000 claims description 32
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 26
- 238000010992 reflux Methods 0.000 claims description 26
- 238000012856 packing Methods 0.000 claims description 20
- 230000008569 process Effects 0.000 claims description 18
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 15
- 229910001220 stainless steel Inorganic materials 0.000 claims description 10
- 239000010935 stainless steel Substances 0.000 claims description 10
- 238000004821 distillation Methods 0.000 claims description 7
- 239000010408 film Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000007789 gas Substances 0.000 description 32
- 239000000047 product Substances 0.000 description 26
- 238000001704 evaporation Methods 0.000 description 20
- 230000008020 evaporation Effects 0.000 description 20
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 11
- 229940035437 1,3-propanediol Drugs 0.000 description 11
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 11
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 11
- 238000000926 separation method Methods 0.000 description 11
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 6
- 238000005265 energy consumption Methods 0.000 description 6
- 238000004064 recycling Methods 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002918 waste heat Substances 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 238000004134 energy conservation Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- -1 polytrimethylene terephthalate Polymers 0.000 description 2
- 229920002215 polytrimethylene terephthalate Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000009044 synergistic interaction Effects 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 1
- 206010057040 Temperature intolerance Diseases 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000008543 heat sensitivity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000012886 linear function Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
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Abstract
The invention provides a method for separating and recovering acrolein from a product system for preparing 3-hydroxy-propanal by hydration of acrolein. The method comprises the following steps: step S1, carrying out first rectification on a product system for preparing 3-hydroxy-propanal by hydration of acrolein in a recovery rectifying tower to obtain a first tower top gas phase and a first tower bottom liquid phase; s2, condensing the gas phase at the first tower top to obtain a first condensate, and feeding a part of the first condensate into a light component removal rectifying tower to carry out second rectification to obtain a second tower top gas phase and a second tower bottom liquid phase; s3, a part of the second tower bottom liquid phase enters a heavy component removal rectifying tower to carry out third rectification, so as to obtain a third tower top gas phase and a third tower bottom liquid phase; the third condensate is obtained after the gas phase condensation of the third tower top, a part of the third condensate flows back into the heavy-removal rectifying tower, and the rest of the third condensate is stored as acrolein.
Description
Technical Field
The invention relates to the technical field of preparation of 3-hydroxy-propanal, in particular to a method for separating and recovering acrolein from a product system for preparing 3-hydroxy-propanal by hydration of acrolein.
Background
1, 3-propanediol (1, 3-PDO) is an important organic chemical raw material, can be used for producing polytrimethylene terephthalate (PTT) fibers with huge market potential, and has good market prospect. The preparation method of the 3-hydroxy-propanal (3 HPA) by hydration of Acrolein (ACR) and the preparation of the 1, 3-propanediol by hydrogenation is one of the current important industrial routes of the 1, 3-propanediol, and has the advantages of mild process conditions, high atom utilization rate and the like. Since acrolein and 3-hydroxypropanal are relatively active, the conversion of Acrolein (ACR) is generally controlled to about 50% in order to obtain higher product selectivity. However, if the unreacted acrolein in the hydration reaction is not separated and recovered, various impurities are generated in the subsequent hydrogenation reaction, and the unreacted acrolein is also a huge waste of ACR raw materials.
The traditional process generally adopts modes of flash evaporation, vacuum rectification and the like to recycle acrolein, and the method has the following two problems: 1. the operating temperature is higher and the residence time of the acrolein hydration solution in the high temperature zone is longer. Acrolein and 3-hydroxy propanal belong to aldehyde compounds, have heat sensitivity, and are easy to polymerize to form cyclic dimer or linear polymer compounds by heating. The yield of thermally denatured product in the system is a non-linear function of temperature and acrolein concentration/residence time in the distillation system, and it is an exponential function of temperature, and concentration/residence time in the system, with higher temperatures or longer residence times in the rectification system producing more by-products. The cyclic dimers are liquid at normal temperature and pressure, the boiling point is higher than that of the monomers, and the cyclic dimers are discharged from the tower bottom together with 3-hydroxy propanal in the rectification process. These dimers are converted to new impurities in subsequent hydrogenation reactions, and the boiling point of the impurities is close to that of the final product 1, 3-propanediol. The acrolein polymer is solid at normal temperature and normal pressure, so that pipelines and heat exchangers in the rectifying equipment are easy to be blocked, and maintenance cost is increased.
Aldehyde-ketone impurities (such as acetaldehyde, propionaldehyde, acetone, methacrolein, etc.) in the acrolein feed will be enriched in the system with increasing recovery of acrolein. As known from the literature, the conventional method for producing acrolein is propylene gas-solid phase catalytic oxidation, which produces various impurities simultaneously, and commercial acrolein obtained by distillation purification still contains small amounts of low boiling impurities such as acetaldehyde (about 1 to 1.5%), propionaldehyde (about 0.02 to 0.2%) and acetone (about 0.02 to 0.5%). The hydrophilicity of the acetaldehyde is extremely strong, the boiling point of the propanal (bp: 48 ℃), the boiling point of the acetone (bp: 56 ℃) and the boiling point of the acrolein (bp: 52 ℃) are close, and in the process of rectifying and recycling the acrolein by using the acrolein aqueous solution, the impurities can be distilled out of the top of the tower together with the acrolein as light component fractions, and the impurities can not be discharged after the acrolein is recycled. These impurities become progressively enriched as commercial acrolein feed is continually replenished. Acetaldehyde and propionaldehyde have aldehyde group structures, acetone has carbonyl structures, and unsaturated aldehyde impurities which can be formed by aldol condensation of acrolein and 3-hydroxy propionaldehyde in a hydration reaction. These impurities have higher boiling points, are discharged from the bottom of the tower together with 3-hydroxy-propionaldehyde in the rectification process, and are converted into corresponding alcohol compounds in the subsequent hydrogenation reaction.
The heat-sensitive monomer polymerization and the enrichment of aldehyde-ketone impurities in ACR raw materials caused by long high temperature/residence time can reduce the selectivity of the main reaction, generate various alcohol impurities, greatly increase the difficulty of subsequent separation and influence the quality of the final product 1, 3-propanediol (1, 3-PDO).
The prior art has the problems of long residence time, high temperature, low acrolein recovery rate, more impurities and the like caused by more side reactions of acrolein and 3-hydroxy-propionaldehyde in the recovery process with respect to separation of acrolein, and simultaneously does not consider the problem of trace impurity enrichment.
Disclosure of Invention
The invention mainly aims to provide a method for separating and recovering acrolein from a product system for preparing 3-hydroxy-propanal by acrolein hydration, which aims to solve the problems that the recovery rate of acrolein is low, the impurity of 3-hydroxy-propanal is more and the like in the separation and recovery of acrolein from a product system for preparing 3-hydroxy-propanal by acrolein hydration in the prior art.
In order to achieve the above object, according to one aspect of the present invention, there is provided a process for separating and recovering acrolein from a product system for producing 3-hydroxypropanal by hydration of acrolein, the process comprising: step S1, carrying out first rectification on a product system for preparing 3-hydroxy-propanal by hydration of acrolein in a recovery rectifying tower to obtain a first tower top gas phase and a first tower bottom liquid phase; a part of the first bottom liquid phase is boiled again through the first film evaporation and then flows back into the recovery rectifying tower, and the rest part of the first bottom liquid phase is stored as 3-hydroxy propanal; s2, condensing the gas phase of the first tower top to obtain a first condensate, refluxing a part of the first condensate into a recovery rectifying tower, and feeding the rest of the first condensate into a light component removal rectifying tower to carry out second rectification to obtain a second tower top gas phase and a second tower bottom liquid phase; condensing the gas phase at the second tower top to obtain second condensate, returning a part of the second condensate to the light component removing rectifying tower, and storing the rest of the second condensate as impurities of acetaldehyde and propionaldehyde; s3, a part of the second bottom liquid phase is subjected to second film evaporation and reboiling and then flows back into the light component removal rectifying tower, and the rest of the second bottom liquid phase enters the heavy component removal rectifying tower to carry out third rectification, so as to obtain a third top gas phase and a third bottom liquid phase; the third bottom liquid phase is boiled again through third film evaporation and then flows back into the heavy-duty rectification tower, and the rest third bottom liquid is stored as acetone impurity; and (3) condensing the gas phase at the top of the third tower to obtain a third condensate, wherein a part of the third condensate flows back into the heavy-duty stripping rectifying tower, and the rest of the third condensate is stored as acrolein.
Further, the time for the evaporation and reboiling of the first thin film is 70 to 120 seconds.
Further, the second thin film is evaporated and reboiled for 30 to 60 seconds.
Further, the third thin film is evaporated and reboiled for 90 to 150 seconds.
Further, the reflux ratio of the first rectification is 3:1-1:1, preferably the recovery rectification tower is a packed tower, preferably the packing of the packed tower is stainless steel corrugated plate packing, preferably the tray number of the recovery rectification tower is 10-50, preferably 15-30; preferably, the absolute pressure in the recovery rectifying tower is 10 to 30kPa, preferably 15 to 25kPa; preferably, the temperature of the top of the recovery rectifying tower is 5-28 ℃, preferably, the temperature of the bottom of the recovery rectifying tower is 50-70 ℃, and preferably, 55-65 ℃.
Further, the reflux ratio of the second rectification is 5:1-3:1.
Further, the light component removing rectifying tower is a plate tower, preferably the plate number of the light component removing rectifying tower is 15-50, preferably 20-40; preferably, the absolute pressure of the light component removal rectifying tower is 80-101 kPa, preferably 101kPa; the tower top temperature of the light component removal rectifying tower is preferably 20-40 ℃, the tower bottom temperature of the light component removal rectifying tower is preferably 50-70 ℃, and the tower bottom temperature of the light component removal rectifying tower is preferably 52-65 ℃.
Further, the reflux ratio of the third rectification is 3:1 to 1:1.
Further, the de-heavy rectifying tower is a packed tower, preferably the packing of the packed tower is stainless steel corrugated plate packing, preferably the tray number of the de-heavy rectifying tower is 15-50, preferably 20-40; preferably, the absolute pressure in the heavy-duty removal rectifying tower is 80-101 kPa, preferably 101kPa; the tower top temperature of the heavy-removal rectifying tower is preferably 40-60 ℃, and is preferably 50-55 ℃; preferably, the temperature of the tower bottom of the heavy-removal rectifying tower is 60-80 ℃.
Further, the product system for preparing 3-hydroxy-propanal by hydration of acrolein comprises the following components in percentage by weight: 5 to 10 weight percent of 3-hydroxy propanal; 5 to 10wt% of acrolein; 1-2 wt% of acetaldehyde; 0.5 to 1 weight percent of propionaldehyde, 0.5 to 1 weight percent of acetone and the balance of water.
By applying the technical scheme of the invention, the method adopts the coupling of vacuum rectification and thin film evaporation to separate the acrolein, wherein the residence time of a product system in a rectifying tower can be reduced through the advantage of thin film evaporation, so that the content of cyclic dimer or linear polymer byproducts is greatly reduced, the subsequent separation difficulty is further reduced, the acrolein and 3-hydroxy-propionaldehyde are separated from the product system for preparing 3-hydroxy-propionaldehyde by hydration of the acrolein with high stability, and impurities such as acetaldehyde, propionaldehyde, acetone and the like in the acrolein are thoroughly separated through a multi-tower rectifying scheme. On the one hand, the purity and the recovery rate of the acrolein can be greatly improved, the impurities in the solution of the 1, 3-propanediol generated by hydration and hydrogenation of the acrolein can be effectively reduced, the subsequent purification difficulty is reduced, and the quality of the final product 1, 3-propanediol is improved. On the other hand, the method can maintain the high balance rate of the thermosensitive intermediate 3-hydroxy-propionaldehyde and simultaneously avoid the enrichment of trace impurities in the process of recycling acrolein. The method has the advantages of simple equipment, low investment, low energy consumption and less generation of three wastes.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the description serve to explain the invention. In the drawings:
FIG. 1 is a schematic diagram showing an apparatus for separating and recovering acrolein from a product system for producing 3-hydroxypropanal by hydration of acrolein according to example 1.
Wherein the above figures include the following reference numerals:
1. recovering the rectifying tower; 2. a first condenser; 3. a light component removing rectifying tower; 4. a first thin film evaporator; 5. a 3-hydroxypropionaldehyde recovery tank; 6. a second condenser; 7. an acetaldehyde/propionaldehyde recovery tank; 8. a second thin film evaporator; 9. a heavy-removal rectifying tower; 10. a third condenser; 11. an acrolein recovery tank; 12. a third thin film evaporator; 13. acetone recovery tank.
Detailed Description
It should be noted that, in the case of no conflict, the embodiments and features in the embodiments may be combined with each other. The invention will be described in detail below with reference to the drawings in connection with embodiments.
As analyzed in the background art of the present application, in the prior art, the separation and recovery of acrolein from a product system for producing 3-hydroxypropanal by hydration of acrolein has problems of low recovery rate of acrolein, more impurities of 3-hydroxypropanal, and the like, and in order to solve the problems, the present application provides a method for separating and recovering acrolein from a product system for producing 3-hydroxypropanal by hydration of acrolein.
In one exemplary embodiment of the present application, a process for separating and recovering acrolein from a product system for the hydration of acrolein to 3-hydroxypropanal is provided, the process comprising: step S1, carrying out first rectification on a product system for preparing 3-hydroxy-propanal by hydration of acrolein in a recovery rectifying tower to obtain a first tower top gas phase and a first tower bottom liquid phase; a part of the first bottom liquid phase is boiled again through the first film evaporation and then flows back into the recovery rectifying tower, and the rest part of the first bottom liquid phase is stored as 3-hydroxy propanal; s2, condensing the gas phase of the first tower top to obtain a first condensate, refluxing a part of the first condensate into a recovery rectifying tower, and feeding the rest of the first condensate into a light component removal rectifying tower to carry out second rectification to obtain a second tower top gas phase and a second tower bottom liquid phase; condensing the gas phase at the second tower top to obtain second condensate, returning a part of the second condensate to the light component removing rectifying tower, and storing the rest of the second condensate as impurities of acetaldehyde and propionaldehyde; s3, a part of the second bottom liquid phase is subjected to second film evaporation and reboiling and then flows back into the light component removal rectifying tower, and the rest of the second bottom liquid phase enters the heavy component removal rectifying tower to carry out third rectification, so as to obtain a third top gas phase and a third bottom liquid phase; the third bottom liquid phase is boiled again through third film evaporation and then flows back into the heavy-duty rectification tower, and the rest third bottom liquid is stored as acetone impurity; and (3) condensing the gas phase at the top of the third tower to obtain a third condensate, wherein a part of the third condensate flows back into the heavy-duty stripping rectifying tower, and the rest of the third condensate is stored as acrolein.
According to the method, the acrolein is separated by adopting the coupling of vacuum rectification and thin film evaporation, wherein the residence time of a product system in a rectifying tower can be reduced by virtue of the thin film evaporation, so that the content of cyclic dimer or linear polymer byproducts is greatly reduced, the subsequent separation difficulty is further reduced, the acrolein and 3-hydroxy-propanal are separated from the product system for preparing 3-hydroxy-propanal by hydration of the acrolein with high stability, and impurities such as acetaldehyde, propanal, acetone and the like in the acrolein are thoroughly separated by virtue of a multi-tower rectifying scheme. On the one hand, the purity and the recovery rate of the acrolein can be greatly improved, the impurities in the solution of the 1, 3-propanediol generated by hydration and hydrogenation of the acrolein can be effectively reduced, the subsequent purification difficulty is reduced, and the quality of the final product 1, 3-propanediol is improved. On the other hand, the method can maintain the high balance rate of the thermosensitive intermediate 3-hydroxy-propionaldehyde and simultaneously avoid the enrichment of trace impurities in the process of recycling acrolein. The method has the advantages of simple equipment, low investment, low energy consumption and less generation of three wastes.
Preferably, the time for reboiling the first thin film evaporation is 70-120 s, on one hand, the waste heat of the first tower bottom liquid phase is utilized to maintain the temperature of the product system, thereby being beneficial to saving energy and reducing energy consumption, and on the other hand, the residence time of the whole product system in the recovery rectifying tower can be reduced through the first tower bottom liquid phase of the first thin film evaporation part, thereby reducing the probability of polymerization of acrolein and 3-hydroxy-propionaldehyde.
Preferably, the second thin film evaporation reboiling time is 30-60 s, on one hand, the temperature of the first condensate in the light removal rectifying tower is maintained by utilizing the waste heat of the second bottom liquid phase, so that energy conservation is facilitated, energy consumption is reduced, and on the other hand, the residence time of the first condensate in the light removal rectifying tower can be reduced by passing through the second thin film evaporation part of the second bottom liquid phase, so that the probability of polymerization of acrolein and 3-hydroxy-propanal is reduced.
Preferably, the third thin film evaporation reboiling time is 90-150 s, on one hand, the temperature of the second bottom liquid phase in the heavy removal rectifying tower is maintained by utilizing the waste heat of the third bottom liquid phase, so that energy conservation is facilitated, energy consumption is reduced, and on the other hand, the residence time of the second bottom liquid phase in the light removal rectifying tower can be reduced by passing through the third thin film evaporation part, so that the probability of polymerization of acrolein and 3-hydroxy-propanal is reduced.
In one embodiment of the present application, the reflux ratio of the first rectification is 3:1 to 1:1, preferably the recovery rectification column is a packed column, preferably the packing of the packed column is a stainless steel corrugated plate packing, preferably the tray number of the recovery rectification column is 10 to 50, preferably 15 to 30; preferably, the absolute pressure in the recovery rectifying tower is 10 to 30kPa, preferably 15 to 25kPa; preferably, the temperature of the top of the recovery rectifying tower is 5-28 ℃, preferably, the temperature of the bottom of the recovery rectifying tower is 50-70 ℃, and preferably, 55-65 ℃.
Preferably, the reflux ratio, the number of tower plates, the absolute pressure, the tower top temperature and the tower bottom temperature of the first rectification are controlled within the ranges, which is favorable for cooperatively controlling the effect and the efficiency of the whole first rectification, so that 3-hydroxy-propanal is separated from impurities such as acetaldehyde, propanal, acetone, acrolein and the like as much as possible.
Preferably, the reflux ratio of the second rectification is 5:1-3:1, so that the separation effect of the second rectification is improved.
In one embodiment of the present application, the light component removing rectifying tower is a plate tower, preferably the plate number of the light component removing rectifying tower is 15-50, preferably 20-40; preferably, the absolute pressure of the light component removal rectifying tower is 80-101 kPa, preferably 101kPa; the tower top temperature of the light component removal rectifying tower is preferably 20-40 ℃, the tower bottom temperature of the light component removal rectifying tower is preferably 50-70 ℃, and the tower bottom temperature of the light component removal rectifying tower is preferably 52-65 ℃.
The tray number, absolute pressure, overhead temperature and bottoms temperature of the second rectification are preferably controlled within the ranges described above to facilitate the synergistic interaction of these rectification parameters with the reflux ratio of the second rectification, thereby facilitating the separation of acetaldehyde and propionaldehyde impurities as far as possible from acetaldehyde, propionaldehyde, acetone, acrolein and other impurities.
Preferably, the reflux ratio of the third rectification is 3:1-1:1, so that the separation effect and the economy of the third rectification are improved.
In one embodiment of the present application, the heavy-duty removal rectifying tower is a packed tower, preferably a packed tower is a stainless steel corrugated plate packing, preferably the tray number of the heavy-duty removal rectifying tower is 15-50, preferably 20-40; preferably, the absolute pressure in the heavy-duty removal rectifying tower is 80-101 kPa, preferably 101kPa; the tower top temperature of the heavy-removal rectifying tower is preferably 40-60 ℃, and is preferably 50-55 ℃; preferably, the temperature of the tower bottom of the heavy-removal rectifying tower is 60-80 ℃.
The tray number, absolute pressure, overhead temperature and bottom temperature of the third distillation are preferably controlled within the above ranges, which is advantageous in the synergistic interaction of these distillation parameters with the reflux ratio of the third distillation, thereby facilitating the separation of acetone and acrolein as much as possible.
In some embodiments of the present application, the product system for the hydration of acrolein to 3-hydroxypropionaldehyde comprises, in weight percent: 5 to 10 weight percent of 3-hydroxy propanal; 5 to 10wt% of acrolein; 1-2 wt% of acetaldehyde; 0.5 to 1 weight percent of propionaldehyde, 0.5 to 1 weight percent of acetone and the balance of water. Thereby being beneficial to realizing the purpose of separating and recovering the acrolein from a product system for preparing 3-hydroxy propanal by hydration of the acrolein by using the method.
The advantageous effects of the present application will be further described below with reference to examples.
Example 1
The hydration reaction liquid system for preparing 3-hydroxy-propanal by hydration of acrolein comprises: 8wt% of 3-hydroxypropanal, 7wt% of acrolein, 1wt% of acetaldehyde, 1wt% of propionaldehyde, 1wt% of acetone and 82% of water.
According to the device shown in fig. 1, a product system enters a recovery rectifying tower 1 (a packed tower, wherein the packing is stainless steel corrugated plate packing) for first rectification to obtain a first tower top gas phase and a first tower bottom liquid phase; condensing the gas phase at the first tower top by a first condenser 2, and refluxing one strand of the gas phase at the first tower top into a recovery rectifying tower 1, and performing second rectification on the one strand of the gas phase at the first tower top into a light component removal rectifying tower 3 to obtain a second gas phase at the second tower top and a second liquid phase at the bottom; about 50% of the first bottom liquid phase is reboiled and refluxed into the recovery rectifying column 1 through the first thin film evaporator 4, reboiled for 80 seconds, and the remaining first bottom liquid phase is sent to the 3-hydroxypropanal recovery tank 5, wherein the reflux ratio is 2:1, the number of plates is 30, the absolute pressure is 15kPa, the column top temperature is 20 ℃, and the column bottom temperature is 65 ℃.
Condensing a second tower top gas phase of the light component removal rectifying tower 3 (plate tower) through a second condenser 6, refluxing into the light component removal rectifying tower 3, refluxing into an acetaldehyde/propionaldehyde recovery tank 7, reboiling and refluxing about 60% of a second tower bottom liquid phase through a second thin film evaporator 8, reboiling for 50s, and feeding the rest of the second tower bottom liquid phase into a heavy component removal rectifying tower 9 for third rectification to obtain a third tower top gas phase and a third tower bottom liquid phase; wherein, the reflux ratio is 5:1, the number of tower plates is 50, the absolute pressure is 101kPa, the tower top temperature is 33 ℃, and the tower bottom temperature is 54 ℃.
Condensing a third tower top gas phase of the heavy-duty removal rectifying tower 9 (a packing tower, the packing is stainless steel corrugated plate packing) through a third condenser 10, then feeding the condensed third tower top gas phase into the heavy-duty removal rectifying tower 9, refluxing one of the condensed third tower top gas phases into an acrolein recycling tank 11, reboiling about 50% of a third tower bottom liquid phase through a third thin film evaporator 12, reboiling for 80 seconds, and feeding the rest of the third tower bottom liquid phase into an acetone recycling tank 13, wherein the reflux ratio is 2:1, the number of plates is 50, the absolute pressure is 101kPa, the tower top temperature is 50 ℃, and the tower bottom temperature is 70 ℃.
Example 2
The difference from example 1 is that about 75% of the first bottom liquid phase is reboiled back to the recovery rectifying column 1 via the first thin film evaporator 4 and reboiled for 120s, to finally obtain acrolein.
Example 3
The difference from example 1 is that about 36% of the second bottom liquid phase is reboiled back through the second thin film evaporator 8 and reboiled for 30s, finally acrolein is obtained.
Example 4
The difference from example 1 is that about 94% of the third bottom liquid phase is reboiled back through the third thin film evaporator 12 and reboiled for 150s, to finally obtain acrolein.
Example 5
The difference from example 1 is that the product system is fed into a recovery rectifying tower 1 to carry out first rectification (a packed tower, the packing is stainless steel corrugated plate packing), and a first tower top gas phase and a first tower bottom liquid phase are obtained; condensing the gas phase at the first tower top by a first condenser 2, and refluxing one strand of the gas phase at the first tower top into a recovery rectifying tower 1, and performing second rectification on the one strand of the gas phase at the first tower top into a light component removal rectifying tower 3 to obtain a second gas phase at the second tower top and a second liquid phase at the bottom; about 50% of the first bottom liquid phase is reboiled and returned to the recovery rectifying tower 1 through the first thin film evaporator 4 and reboiled for 80 seconds, and the rest of the first bottom liquid phase is sent to the 3-hydroxy-propanal recovery tank 5, wherein the reflux ratio is 3:1, the tower plate number is 30, the absolute pressure is 20kPa, the tower top temperature is 28 ℃, and the tower bottom temperature is 59 ℃, so that acrolein is finally obtained.
Example 6
The difference from example 1 is that after the second top gas phase of the light ends removal rectifying column 3 (plate column) is condensed by the second condenser 6, one of the two streams is returned to the light ends removal rectifying column 3, one stream is returned to the acetaldehyde/propionaldehyde recovery tank 7, about 60% of the second bottom liquid phase is reboiled and returned by the second thin film evaporator 8, reboiled for 50s, and the remaining second bottom liquid phase is returned to the heavy ends removal rectifying column 9 to be subjected to third rectification, thereby obtaining a third top gas phase and a third bottom liquid phase; wherein, the reflux ratio is 3:1, the tower plate number is 40, the absolute pressure is 101kPa, the tower top temperature is 20 ℃, the tower bottom temperature is 52 ℃, and finally the acrolein is obtained.
Example 7
The difference from example 1 is that the third overhead gas phase of the heavy ends removal rectifying column 9 (packed column, packing is stainless steel corrugated plate packing) is condensed by the third condenser 10, then enters the heavy ends removal rectifying column 9, one of the gas phases is refluxed, the other gas phase enters the acrolein recovery tank 11, about 50% of the third bottom liquid phase is reboiled and refluxed by the third thin film evaporator 12, reboiled for 80 seconds, and the remaining third bottom liquid phase enters the acetone recovery tank 13, wherein the reflux ratio is 3:1, the number of plates is 40, the absolute pressure is 101kPa, the overhead temperature is 55 ℃, and the bottom temperature is 80 ℃, thereby finally obtaining acrolein.
Example 8
The difference from example 1 is that the hydration reaction liquid system for preparing 3-hydroxy-propanal by hydration of acrolein comprises: 10wt% of 3-hydroxy-propanal, 9.5wt% of acrolein, 1wt% of acetaldehyde, 0.5wt% of propanal, 1wt% of acetone and 78% of water, finally obtaining acrolein.
Recovery and purity of acrolein obtained in examples 1 to 8 above are shown in Table 1.
TABLE 1
Examples/comparative examples | Recovery/% | Purity/% |
Example 1 | 97.9 | 97.6 |
Example 2 | 98.6 | 98.9 |
Example 3 | 97.7 | 98.1 |
Example 4 | 97.0 | 97.1 |
Example 5 | 98.2 | 96.2 |
Example 6 | 98.3 | 92.2 |
Example 7 | 98.5 | 93.2 |
Example 8 | 97.8 | 98.1 |
From the above description, it can be seen that the above embodiments of the present invention achieve the following technical effects:
according to the method, the acrolein is separated by adopting the coupling of vacuum rectification and thin film evaporation, wherein the residence time of a product system in a rectifying tower can be reduced by virtue of the thin film evaporation, so that the content of cyclic dimer or linear polymer byproducts is greatly reduced, the subsequent separation difficulty is further reduced, the acrolein and 3-hydroxy-propanal are separated from the product system for preparing 3-hydroxy-propanal by hydration of the acrolein with high stability, and impurities such as acetaldehyde, propanal, acetone and the like in the acrolein are thoroughly separated by virtue of a multi-tower rectifying scheme. On the one hand, the purity and the recovery rate of the acrolein can be greatly improved, the impurities in the solution of the 1, 3-propanediol generated by hydration and hydrogenation of the acrolein can be effectively reduced, the subsequent purification difficulty is reduced, and the quality of the final product 1, 3-propanediol is improved. On the other hand, the method can maintain the high balance rate of the thermosensitive intermediate 3-hydroxy-propionaldehyde and simultaneously avoid the enrichment of trace impurities in the process of recycling acrolein. The method has the advantages of simple equipment, low investment, low energy consumption and less generation of three wastes.
The above description is only of the preferred embodiments of the present invention and is not intended to limit the present invention, but various modifications and variations can be made to the present invention by those skilled in the art. Any modification, equivalent replacement, improvement, etc. 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 process for separating and recovering acrolein from a product system for the hydration of acrolein to produce 3-hydroxypropanal, comprising:
step S1, carrying out first rectification on a product system for preparing 3-hydroxy-propanal by hydration of acrolein in a recovery rectifying tower to obtain a first tower top gas phase and a first tower bottom liquid phase;
a part of the first bottom liquid phase is vaporized and reboiled by a first thin film and then flows back into the recovery rectifying tower, and the rest part of the first bottom liquid phase is stored as 3-hydroxy propanal;
s2, condensing the gas phase of the first tower top to obtain a first condensate, returning a part of the first condensate to the recovery rectifying tower, and feeding the rest of the first condensate to the light component removal rectifying tower to perform second rectification to obtain a second tower top gas phase and a second tower bottom liquid phase;
the second condensate is obtained after the gas phase condensation of the second tower top, a part of the second condensate flows back into the light component removal rectifying tower, and the rest part of the second condensate is stored as acetaldehyde and propionaldehyde impurities;
s3, a part of the second bottom liquid phase is vaporized and reboiled through a second thin film and flows back into the light component removal rectifying tower, and the rest of the second bottom liquid phase enters the heavy component removal rectifying tower to carry out third rectification, so as to obtain a third top gas phase and a third bottom liquid phase;
the third bottom liquid phase is evaporated and reboiled through a third film and then flows back into the heavy-removal rectifying tower, and the rest part of the third bottom liquid phase is stored as acetone impurities;
and (3) condensing the gas phase at the top of the third tower to obtain third condensate, wherein a part of the third condensate flows back into the de-duplication rectifying tower, and the rest of the third condensate is stored as acrolein.
2. The method of claim 1, wherein the first thin film is vaporized and reboiled for a time period of from 70 to 120 seconds.
3. The method according to claim 1 or 2, wherein the second thin film is evaporated and reboiled for a period of 30 to 60 seconds.
4. A method according to any one of claims 1 to 3, wherein the third thin film is evaporated and reboiled for a time of 90 to 150s.
5. The process according to any one of claims 1 to 4, wherein the reflux ratio of the first rectification is 3:1 to 1:1, preferably the recovery rectification column is a packed column, preferably the packing of the packed column is a stainless steel corrugated plate packing, preferably the number of plates of the recovery rectification column is 10 to 50, preferably 15 to 30; preferably, the absolute pressure in the recovery rectifying tower is 10 to 30kPa, preferably 15 to 25kPa; preferably, the temperature of the top of the recovery rectifying tower is 5-28 ℃, preferably the temperature of the bottom of the recovery rectifying tower is 50-70 ℃, preferably 55-65 ℃.
6. The process according to any one of claims 1 to 5, wherein the reflux ratio of the second rectification is from 5:1 to 3:1.
7. The method according to any one of claims 1 to 6, wherein the light ends removal distillation column is a tray column, preferably the tray number of the light ends removal distillation column is 15-50, preferably 20-40; preferably, the absolute pressure of the light component removal rectifying tower is 80-101 kPa, preferably 101kPa; preferably, the tower top temperature of the light component removal rectifying tower is 20-40 ℃, preferably the tower bottom temperature of the light component removal rectifying tower is 50-70 ℃, and preferably 52-65 ℃.
8. The process according to any one of claims 1 to 7, wherein the reflux ratio of the third rectification is from 3:1 to 1:1.
9. The process according to any one of claims 1 to 8, wherein the de-duplication rectification column is a packed column, preferably the packing of the packed column is a stainless steel corrugated plate packing, preferably the tray number of the de-duplication rectification column is 15-50, preferably 20-40; preferably, the absolute pressure in the heavy-removal rectifying tower is 80-101 kPa, preferably 101kPa; preferably, the temperature of the top of the heavy removal rectifying tower is 40-60 ℃, preferably 50-55 ℃; preferably, the temperature of the tower bottom of the heavy-removal rectifying tower is 60-80 ℃.
10. The process according to any one of claims 1 to 9, characterized in that said product system for the hydration of acrolein to 3-hydroxypropanal comprises, in weight percent:
5 to 10 weight percent of 3-hydroxy propanal;
5 to 10wt% of acrolein;
1-2 wt% of acetaldehyde;
0.5 to 1wt% of propanal; and
0.5 to 1 weight percent of acetone and the balance of water.
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Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3518310A (en) * | 1968-02-09 | 1970-06-30 | Shell Oil Co | Preparation of beta-hydroxypropionaldehyde and beta-alkoxypropionaldehydes |
US5093537A (en) * | 1991-07-24 | 1992-03-03 | Hoechst Celanese Corporation | Method for the manufacture of 1,3-propanediol |
CN1398843A (en) * | 2002-08-20 | 2003-02-26 | 黑龙江省石油化学研究院 | Acraldehyde recovering method |
CN1572777A (en) * | 2001-10-30 | 2005-02-02 | 三菱化学株式会社 | Method for purifying (meth)acrylic acid |
CN101033180A (en) * | 2007-04-12 | 2007-09-12 | 上海华谊丙烯酸有限公司 | Fractionating tower for separating acrylic aldehyde from 3-hydroxypropionaldehyde solution |
CN102659541A (en) * | 2012-04-28 | 2012-09-12 | 重庆紫光天化蛋氨酸有限责任公司 | Method for purifying acrolein and treatment system for preparing acrolein |
CN111100095A (en) * | 2019-12-24 | 2020-05-05 | 山东联创产业发展集团股份有限公司 | Method for separating propylene oxide, acrolein and acetone which are propylene oxidation products |
CN112778111A (en) * | 2021-01-25 | 2021-05-11 | 浙江恒澜科技有限公司 | Method for separating and recovering acrolein from hydration product of preparing 3-hydroxypropionaldehyde by acrolein hydration |
CN112920031A (en) * | 2021-01-27 | 2021-06-08 | 浙江恒澜科技有限公司 | Method for separating and recycling acrolein in process of preparing 1, 3-propylene glycol |
CN113277933A (en) * | 2021-06-04 | 2021-08-20 | 江苏扬农化工集团有限公司 | Method and device for preparing 3-hydroxypropionaldehyde by continuous catalytic distillation |
CN113651777A (en) * | 2020-05-12 | 2021-11-16 | 中国石油化工股份有限公司 | Reaction rectification dealdehyding process |
-
2022
- 2022-10-28 CN CN202211336755.XA patent/CN116041162B/en active Active
Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3518310A (en) * | 1968-02-09 | 1970-06-30 | Shell Oil Co | Preparation of beta-hydroxypropionaldehyde and beta-alkoxypropionaldehydes |
US5093537A (en) * | 1991-07-24 | 1992-03-03 | Hoechst Celanese Corporation | Method for the manufacture of 1,3-propanediol |
CN1572777A (en) * | 2001-10-30 | 2005-02-02 | 三菱化学株式会社 | Method for purifying (meth)acrylic acid |
CN1398843A (en) * | 2002-08-20 | 2003-02-26 | 黑龙江省石油化学研究院 | Acraldehyde recovering method |
CN101033180A (en) * | 2007-04-12 | 2007-09-12 | 上海华谊丙烯酸有限公司 | Fractionating tower for separating acrylic aldehyde from 3-hydroxypropionaldehyde solution |
CN102659541A (en) * | 2012-04-28 | 2012-09-12 | 重庆紫光天化蛋氨酸有限责任公司 | Method for purifying acrolein and treatment system for preparing acrolein |
CN111100095A (en) * | 2019-12-24 | 2020-05-05 | 山东联创产业发展集团股份有限公司 | Method for separating propylene oxide, acrolein and acetone which are propylene oxidation products |
CN113651777A (en) * | 2020-05-12 | 2021-11-16 | 中国石油化工股份有限公司 | Reaction rectification dealdehyding process |
CN112778111A (en) * | 2021-01-25 | 2021-05-11 | 浙江恒澜科技有限公司 | Method for separating and recovering acrolein from hydration product of preparing 3-hydroxypropionaldehyde by acrolein hydration |
CN112920031A (en) * | 2021-01-27 | 2021-06-08 | 浙江恒澜科技有限公司 | Method for separating and recycling acrolein in process of preparing 1, 3-propylene glycol |
CN113277933A (en) * | 2021-06-04 | 2021-08-20 | 江苏扬农化工集团有限公司 | Method and device for preparing 3-hydroxypropionaldehyde by continuous catalytic distillation |
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