CN114456131A - Tetrahydrofuran production system and preparation method - Google Patents
Tetrahydrofuran production system and preparation method Download PDFInfo
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- CN114456131A CN114456131A CN202011132403.3A CN202011132403A CN114456131A CN 114456131 A CN114456131 A CN 114456131A CN 202011132403 A CN202011132403 A CN 202011132403A CN 114456131 A CN114456131 A CN 114456131A
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- Prior art keywords
- tetrahydrofuran
- fixed bed
- bed reactor
- rectifying tower
- butanediol
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title claims abstract description 102
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims abstract description 68
- 238000006243 chemical reaction Methods 0.000 claims abstract description 57
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 14
- 239000011347 resin Substances 0.000 claims description 9
- 229920005989 resin Polymers 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 8
- 238000005192 partition Methods 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 9
- 238000000926 separation method Methods 0.000 abstract description 6
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 4
- 230000007797 corrosion Effects 0.000 abstract description 3
- 238000005260 corrosion Methods 0.000 abstract description 3
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 14
- 239000002994 raw material Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000012535 impurity Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000571 coke Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D307/08—Preparation of tetrahydrofuran
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Abstract
A production system and a preparation method of tetrahydrofuran belong to the technical field of tetrahydrofuran preparation processes. In the prior art, the preparation of tetrahydrofuran mainly adopts concentrated sulfuric acid as a catalyst, and 1, 4-butanediol is cyclized at high temperature to generate tetrahydrofuran. On one hand, the high temperature and the strong acid cause serious corrosion to production equipment, and on the other hand, other products such as 2, 3-dihydrofuran and the like are easily produced, so that the separation is difficult. The invention adopts the combination of the fixed bed reactor, the rectifying tower and the reaction kettle, adopts two-stage reaction, greatly reduces the reaction intensity, simplifies the production process and saves the energy consumption.
Description
Technical Field
A production system and a preparation method of tetrahydrofuran belong to the technical field of tetrahydrofuran preparation processes.
Background
Tetrahydrofuran is an important organic synthetic raw material and is a solvent with excellent performance, and is particularly suitable for dissolving PVC, polyvinylidene chloride and butylaniline.
The existing process for producing tetrahydrofuran comprises the following steps: a22% aqueous solution of sulfuric acid was fed to the reactor, 1, 4-butanediol was fed at 100 ℃ at a rate of about 110kg/h, the overhead temperature was maintained at about 80 ℃ and an aqueous solution containing 80% tetrahydrofuran was obtained from the overhead at a rate of about 110 kg/h. After 50t of 1, 4-butanediol had been added, about 70kg of coke were removed from the reactor. The coke is filtered, the obtained sulfuric acid aqueous solution can be reused, and the yield of the tetrahydrofuran in the process can reach more than 99 percent. Sulfuric acid is the earliest catalyst used in the industrial production of tetrahydrofuran and is also the catalyst used more frequently in the production nowadays. Although the technology is mature, on one hand, the adopted catalyst sulfuric acid is extremely easy to corrode equipment and pollute the environment; on the other hand, the reactor has a cleaning process, production is necessarily interrupted when feeding materials each time, the efficiency is low, the whole process is complex, the operation requirement is high, and the loss of 1, 4-butanediol is serious. Meanwhile, under strong acid and high temperature, 1, 4-butanediol is incompletely cyclized to generate 2, 3-dihydrofuran impurities, and the boiling points of the 2, 3-dihydrofuran impurities and tetrahydrofuran are close, so that the impurities are extremely difficult to separate in a subsequent purification process, and the purity of the tetrahydrofuran is reduced.
Disclosure of Invention
The technical problem to be solved by the invention is as follows: overcomes the defects of the prior art, and provides a tetrahydrofuran production system and a preparation method thereof, which have the advantages of no corrosion, no interruption, simple process and low loss.
The technical scheme adopted by the invention for solving the technical problems is as follows:
a preparation method of tetrahydrofuran is characterized in that: heating 1, 4-butanediol to 80-100 ℃, feeding the heated 1, 4-butanediol into a fixed bed reactor filled with an acidic cation resin catalyst, azeotroping the product at the top of the tower, feeding the product into the middle part of a rectifying tower after the product flows out, and feeding the product into a reaction kettle, wherein the reaction kettle contains the acidic cation resin catalyst and has the pressure of 0-0.1 MPa, the temperature of the top of the rectifying tower is controlled to be 65-100 ℃, and the reflux ratio is 1-5 h-1(ii) a The product tetrahydrofuran is obtained from the top of the column.
The process utilizes two-stage reaction of fixed bed reaction and common reaction, the temperature at the top of the fixed bed reactor is about the cyclization azeotropic temperature of tetrahydrofuran and 1, 4-butanediol, so that the product tetrahydrofuran and a small part of 1, 4-butanediol flow into a rectifying tower from the top of the fixed bed reactor, the reaction in the fixed bed reactor is promoted to be carried out in the positive direction, and the conversion rate of the 1, 4-butanediol is improved; and the tetrahydrofuran is rectified and extracted in the mixture of the tetrahydrofuran and the 1, 4-butanediol falling into the reaction kettle through the rectifying tower, the cyclization reaction of the 1, 4-butanediol in the mixture is promoted to be carried out in the forward direction again, and 99-100% conversion of the 1, 4-butanediol can be finally realized under the circulation. In addition, only mild acidic cation resin catalyst is needed for the two reactions, so that the generation of 2, 3-dihydrofuran is avoided, and the obtained tetrahydrofuran has high purity.
Preferably, the space velocity of the fixed bed reactor is 0.5-4 h-1. The lower the temperature, the smaller the space velocity required, the more complete the reaction, the higher the temperature, the higher the space velocity required, and the lower the tetrahydrofuran content in the material entering the rectifying tower and the reaction kettle.
Preferably, the number of the plates of the rectifying tower is 30-60.
Preferably, the concentration by weight of the 1, 4-butanediol is greater than 70%.
Preferably, the acidic cation resin catalyst exchange equivalent is 5.2mmolH+/g。
A production system of tetrahydrofuran, characterized in that: comprises a fixed bed reactor, a rectifying tower and a reaction kettle; the top of the fixed bed reactor is connected with a rectifying tower; the bottom of the rectifying tower is communicated with the top of the reaction kettle.
The two-stage reaction of a fixed bed and a common reactor is adopted, and a system for separating products by a rectifying tower is combined, so that the 1, 4-butanediol adopts mild reaction conditions in the two-stage reaction, the complete conversion can be realized, and the byproduct 2, 3-dihydrofuran can not be generated. The reactions in each step of the whole production system are not influenced mutually, and the fixed bed reactor can continuously feed, so that the continuity of the whole reaction process is realized, and the production efficiency is greatly improved.
Preferably, the reaction kettle is internally provided with a partition plate, and the bottom of the reaction kettle is provided with a discharge hole. The baffle among the reation kettle can bear the weight of the catalyst, and with the separation of reation kettle bottom, along with the going on of reaction, can generate heavier components such as part coke matter in the reation kettle, open the drain hole of reation kettle bottom this moment and discharge some heavy components, can not influence the continuity of internal reaction to can utilize the mixture that comes from fixed bed reactor's 1, 4-butanediol and tetrahydrofuran to the abundant washing in reation kettle bottom, the internal environment of abundant protection cauldron.
Preferably, the fixed bed reactor is connected with the middle section of the rectifying tower. A part of tetrahydrofuran carrying temperature in the materials from the fixed bed reactor can be directly rectified and extracted from the middle section, and compared with the tetrahydrofuran falling into a reaction kettle and then rectified and separated from reaction raw materials, the rectification separation efficiency is higher.
Compared with the prior art, the invention has the beneficial effects that: the method has the advantages that the tetrahydrofuran is produced under mild catalyst and process conditions by utilizing two-stage reaction, no by-product is generated, the obtained tetrahydrofuran product only contains water due to the control of the temperature at the top of the rectifying tower, the product separation process is equivalent to two-stage separation, the product and raw material separation process is simplified by adopting the solid catalyst, and the product purity is high; the whole system and the preparation method only have strict requirements on temperature control, and the whole process is simple to operate; the corrosion of strong acid to the reactor is avoided; the largest heat change is only before the 1, 4-butanediol enters the fixed bed reactor, and the energy consumption is low; the whole production flow is continuous and efficient, the cleaning of impurities can be realized without interrupting the production, and the production efficiency is improved.
Drawings
FIG. 1 is a schematic view of a system for producing tetrahydrofuran according to example 1.
Wherein, 1 raw material tank, 2 raw material pumps, 3 fixed bed reactors, 4 rectifying columns and 5 reaction kettles.
Detailed Description
Example 13 is the best mode for carrying out the invention, and the invention is further described below with reference to examples.
The following examples were all completed in 1L production line of the laboratory of the Chinese petrochemical, Qilu division.
Examples 1 to 15
Referring to figure 1: a tetrahydrofuran production system, which comprises a raw material tank 1 and raw materialsPump 2, fixed bed reactor 3, rectifying column 4, reation kettle 5. The raw material tank 1 is connected with the bottom of the fixed bed reactor 3 through the raw material pump 2, the top of the fixed bed reactor 3 is connected with the middle section of the rectifying tower 4, and the bottom of the rectifying tower 4 is communicated with the top of the reaction kettle 5; a partition plate is arranged in the middle layer of the reaction kettle 5, a fixed catalyst is arranged on the partition plate, and a discharge hole is formed in the bottom of the reaction kettle 5; the exchange equivalent of the catalyst filled in the reaction kettle 5 and the fixed bed reactor 3 is 5.2mmolH+The catalyst loading of the fixed bed reactor 3 was 40ml and the catalyst loading in the reactor was 100ml per g of the acidic cationic resin catalyst.
A preparation method of tetrahydrofuran, utilize the above-mentioned production system of tetrahydrofuran, after heating up to 80-100 duC, 1, 4-butanediol enters from the inferior part of the fixed bed reactor 3 equipped with acid cation resin catalyst, the product cyclizes azeotropy at the top of the tower, enter the middle part of the rectifying column 4 and flow into the reactor 5 after flowing out, the pressure is 0-0.1 MPa in the reactor 5, and control temperature, reflux ratio of top of the rectifying column 4; the product tetrahydrofuran is obtained from the top of the column. The purity of the 1, 4-butanediol is 70-100%.
The process conditions and the total conversion of 1, 4-butanediol are shown in Table 1 below.
TABLE 1 reaction results at different temperatures and space velocities
Comparative example 1
Example 1 was repeated, the temperature set in the fixed-bed reactor 3 being 75 ℃.
Taking a mixture sample from the top end of the fixed bed reactor 3, detecting the contents of tetrahydrofuran and 1, 4-butanediol, and calculating the conversion rate of the 1, 4-butanediol to be 54.18%; the weight of the finally obtained tetrahydrofuran was measured, and the conversion of the finally obtained 1, 4-butanediol was calculated to be 86.27%.
Comparative example 2
Example 1 was repeated, the temperature set in the fixed-bed reactor 3 being 110 ℃.
Taking a mixture sample from the top end of the fixed bed reactor 3, detecting the contents of tetrahydrofuran and 1, 4-butanediol, and calculating the conversion rate of the 1, 4-butanediol to be 61.35 percent; the weight of the finally obtained tetrahydrofuran was measured, and the conversion of the finally obtained 1, 4-butanediol was calculated to be 88.14%.
Comparative example 3
Example 1 was repeated, with the top of the rectifying column 4 set at a controlled temperature of 60 ℃ and the temperature in the test reactor 5 at 96 ℃.
The weight of tetrahydrofuran finally obtained at the top of the rectifying tower 4 was measured, and the conversion rate of 1, 4-butanediol was calculated to be 91.53%.
Comparative example 4
Example 1 was repeated, the top of the rectifying column 4 was set at a controlled temperature of 110 ℃ and the temperature in the reaction vessel 5 was measured at 144 ℃.
The weight of tetrahydrofuran finally obtained at the top of the rectifying tower 4 was measured, and the conversion rate of 1, 4-butanediol was calculated to be 92.72%.
Comparative example 5
Example 1 was repeated, and the pressure in reaction vessel 5 was controlled to 0.15 MPa.
The weight of tetrahydrofuran finally obtained at the top of the rectifying tower 4 was measured, and the conversion rate of 1, 4-butanediol was calculated to be 91.56%.
According to the embodiments 3, 5, 9, 10 and 13, the system and the preparation method of the invention are proved to be capable of completely realizing 100% conversion of 1, 4-butanediol, after the system enters into circulation in large-scale industrial production, the 1, 4-butanediol which is not cyclized can be separated from the product and fall into the reaction kettle 5 for continuous reaction due to the limitation of the top azeotropic temperature of the fixed bed reactor 3 and the top temperature of the rectifying tower 4, and the conversion rate approaches to 100%; in addition, extra 1, 4-butanediol does not need to be introduced in the whole process to clean the reaction kettle 5; meanwhile, the fixed bed reactor 3 and the top of the rectifying tower 4 are stably controlled, so that the energy consumption requirement is low, almost no temperature rise and temperature reduction process is carried out, and the energy is saved.
The foregoing is directed to preferred embodiments of the present invention, other and further embodiments of the invention may be devised without departing from the basic scope thereof, and the scope thereof is determined by the claims that follow. However, any simple modification, equivalent change and modification of the above embodiments according to the technical essence of the present invention are within the protection scope of the technical solution of the present invention.
Claims (8)
1. A preparation method of tetrahydrofuran is characterized in that: 1, 4-butanediol is heated to 80-100 ℃ and then enters a fixed bed reactor (3) filled with an acidic cation resin catalyst from the lower part, the temperature in the fixed bed reactor (3) is controlled to be 80-100 ℃, a product flows out from the top of the tower, enters the middle part of a rectifying tower (4) and flows into a reaction kettle (5), the reaction kettle (5) contains the acidic cation resin catalyst, the pressure is 0-0.1 MPa, the temperature at the top of the rectifying tower (4) is controlled to be 65-100 ℃, and the reflux ratio is 1-5 h-1(ii) a The product tetrahydrofuran is obtained from the top of the column.
2. The process for producing tetrahydrofuran according to claim 1, wherein: the space velocity in the fixed bed reactor (3) is 0.5-4 h-1。
3. The process for producing tetrahydrofuran according to claim 1, wherein: the number of the tower plates of the rectifying tower (4) is 30-60.
4. The process for producing tetrahydrofuran according to claim 1, wherein: the weight concentration of the 1, 4-butanediol is more than 70 percent.
5. The process for producing tetrahydrofuran according to claim 1, wherein: the exchange equivalent of the acidic cation resin catalyst is 5.2mmol H+/g。
6. A production system of tetrahydrofuran, characterized in that: comprises a fixed bed reactor (3), a rectifying tower (4) and a reaction kettle (5); the top of the fixed bed reactor (3) is connected with a rectifying tower (4); the bottom of the rectifying tower (4) is communicated with the top of the reaction kettle (5).
7. The system for producing tetrahydrofuran according to claim 6, wherein: the reaction kettle (5) is internally provided with a partition plate, and the bottom of the reaction kettle is provided with a discharge hole.
8. The system for producing tetrahydrofuran according to claim 6, wherein: the fixed bed reactor (3) is connected with the middle section of the rectifying tower (4).
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| CN202011132403.3A CN114456131A (en) | 2020-10-21 | 2020-10-21 | Tetrahydrofuran production system and preparation method |
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| CN202011132403.3A CN114456131A (en) | 2020-10-21 | 2020-10-21 | Tetrahydrofuran production system and preparation method |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114751877A (en) * | 2022-05-13 | 2022-07-15 | 中化学科学技术研究有限公司 | Production method of tetrahydrofuran |
| CN114805250A (en) * | 2022-05-24 | 2022-07-29 | 中化学科学技术研究有限公司 | Preparation process and device of tetrahydrofuran |
| CN115043795A (en) * | 2022-07-28 | 2022-09-13 | 中化学科学技术研究有限公司 | Production process of tetrahydrofuran |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114751877A (en) * | 2022-05-13 | 2022-07-15 | 中化学科学技术研究有限公司 | Production method of tetrahydrofuran |
| CN114751877B (en) * | 2022-05-13 | 2023-12-29 | 中化学科学技术研究有限公司 | Tetrahydrofuran production method |
| CN114805250A (en) * | 2022-05-24 | 2022-07-29 | 中化学科学技术研究有限公司 | Preparation process and device of tetrahydrofuran |
| CN114805250B (en) * | 2022-05-24 | 2023-12-29 | 中化学科学技术研究有限公司 | Tetrahydrofuran preparation process and device |
| CN115043795A (en) * | 2022-07-28 | 2022-09-13 | 中化学科学技术研究有限公司 | Production process of tetrahydrofuran |
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