CN102180772B - Method for preparing cyclohexanol by hydrating cyclohexene - Google Patents
Method for preparing cyclohexanol by hydrating cyclohexene Download PDFInfo
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Abstract
The invention discloses a method for preparing cyclohexanol by hydrating cyclohexene. The method comprises the following steps of: a) performing phase separation on mixed liquid obtained through hydration reaction of the cyclohexene and water in an oil water phase splitter; b) allowing the oil phase obtained in the step a to enter a filter for separation; c) allowing the aqueous phase obtained in the step a to enter an extraction phase splitter, extracting by using a light component which enters the extraction phase splitter from the top of a first rectifying tower in the step d as an extractant, allowing the extracted aqueous phase to return to a reactor for recycling, and allowing the extracted oil phase to enter the filter in the step b for filtration; d) allowing the oil phase filtered by the filter in the step b to enter the first rectifying tower, allowing one part of the cyclohexene-containing light component obtained on the top of the tower to enter the extraction phase splitter in the step c, and allowing the other part of the light component to enter the reactor for recycling; and e) allowing a tower bottom material obtained at the bottom of the first rectifying tower in the step d to enter a second rectifying and separating tower, and withdrawing the cyclohexanol product from the middle part of the tower. By the method, the cyclohexanol with the purity of over 99.6 percent can be prepared.
Description
Technical field
The present invention relates to a kind of method for preparing hexalin, particularly relate to a kind of method of preparing cyclohexanol by cyclohexene hydration reaction.
Background technology
Hexalin is the main raw material of the various ethenoid resin paints of preparation, and is widely used as the solvent of many high molecular polymers,
The method of traditional mode of production hexalin is that benzene hydrogenation is made hexanaphthene, then through catalyzed oxidation hexalin processed and pimelinketone, the method exists one-pass yield low, and energy consumption is high, and the problem such as equipment corrosion.Along with benzene selective hydrogenation prepares deepening continuously of tetrahydrobenzene research, there has been certain application prospect significantly in the synthetic method for preparing hexalin take tetrahydrobenzene as raw material.Compare with traditional technique, the production technique for preparing hexalin by tetrahydrobenzene has the hydrogen source of saving, transformation efficiency is high, side reaction is few, reaction temperature and etc. characteristics.Japan's Asahi Kasei Corporation built up the production equipment of 60kt/a and goes into operation in nineteen ninety, and China god horse group introduces in recent years, the digestion foreign technology also puts into production.
As far back as 20 century 70s, the US3988379 report can make cyclohexene hydration make hexalin take sulfuric acid as catalyzer.Because sulfuric acid is corrosive to equipment, chemical company of Japanese Asahi Chemical Industry has proposed to adopt the cyclohexene hydrating process of solid acid molecular sieve catalytic in nineteen eighty-three, has opened the gate of solid acid catalysis cyclohexene hydration research.JP1998-218812 reports the corresponding cyclic alcohol technique of cycloolefin hydration continuous production, mainly comprises following step: (1) carries out the continuous hydration reaction of cyclenes under molecular sieve solid acid and the existence of high boiling point organic additive; (2) separate oil phase and water; (3) oil phase is delivered to the first rectifying tower rectifying after, tower top obtains unreacted cyclenes, obtains cyclic alcohol and organic additive at the bottom of tower; (4) two tower rectifying are delivered in the bottom of a tower after, a tower top part is circulated to hydration reactor, most of cyclic alcohol is as product, organic additive is recycled to hydration reactor.The method that the disclosed cyclenes hydration of JP1999-080056 prepares cyclic alcohol is the first preliminary rectifying of the mixture that contains cyclic alcohol A, unreacted cyclenes B and by product C, reclaim cyclic alcohol A, simultaneously cyclenes B and by product C are delivered in knockout tower, after removing by product C, cyclenes B is recycled.The disclosed preparation technology of JP1999-228456 is with after the phase-splitting of hydration reaction liquid, after oil phase is delivered to the first rectifying tower separation, tower top obtains unreacted cyclenes etc., obtain the hexalin product at the bottom of tower, after two tower rectifying are delivered at the top of one tower, at the bottom of tower, a part is circulated to hydration reactor, and the tower top light constituent is discharged as impurity.
Existing technique Shortcomings part shows as:
(1) the hydration reaction compound is after oily water separation, and water still is dissolved with a certain amount of hexalin, because hydration reaction is a reversible reaction, contains the direct Returning reacting system of water of hexalin, can reduce the per pass conversion of hydration reaction;
(2) the hydration reaction compound is after oily water separation, oil phase is still carried a certain amount of hydration catalyst secretly, because cyclohexene hydration process catalyzer also has dehydrating function, in follow-up tetrahydrobenzene-hexalin rectifying separation process, with steaming of tetrahydrobenzene, hexalin easily dehydration shifts to tetrahydrobenzene balance direction, and the hexalin product yield is reduced.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of method of preparing cyclohexanol by cyclohexene hydration reaction, can access high purity cyclohexanol, and the hexalin selectivity is high, and can make catalyzer obtain effective recycling, reduces catalyst attrition.
For solving the problems of the technologies described above, the invention provides a kind of method of preparing cyclohexanol by cyclohexene hydration reaction, comprise the steps:
A) tetrahydrobenzene and water are carried out the heterogeneous catalysis hydration reaction in hydration reactor under catalyst action, the reaction product mixed solution that obtains carries out phase-splitting in the profit phase splitter, make oil phase and aqueous phase separation, contain the materials such as hexalin, tetrahydrobenzene, hexanaphthene in oil phase, water is the outstanding slurry that contains catalyzer;
B) separate through the profit phase splitter oil phase that obtains in step a and enter strainer, isolate the solidss such as catalyzer;
C) separate through the profit phase splitter water that obtains in step a and enter the extraction phase splitter, enter into the light constituent that contains tetrahydrobenzene of extraction phase splitter as extraction agent by the first rectifying tower top in steps d, the hexalin of described aqueous phase dissolving is extracted, the reactor cycles that the water that obtains through the separation of extraction phase splitter turns back in step a is used, and the strainer that the oil phase that extraction obtains enters into step b filters;
D) oil phase that is filtered in step b enters the first rectifying separation tower and carries out rectifying separation, and the light constituent part that contains tetrahydrobenzene that tower top obtains enters into the extraction phase splitter of step c, and a part is returned in the reactor of described step a and recycled;
E) the tower reactor material that contains hexalin that obtains at the bottom of the first rectifying tower in steps d enters the second rectifying separation tower, the light constituent that contains tetrahydrobenzene that the second rectifying separation column overhead obtains returns to the first rectifying separation tower, and the product hexalin is from the second rectifying separation tower middle part extraction.
The method of above-mentioned preparing cyclohexanol by cyclohexene hydration reaction, wherein, the light constituent that contains tetrahydrobenzene from the first rectifying separation column overhead that enters the extraction phase splitter in described step c be 0.1-2 from the mass flux ratio of separating through the profit phase splitter water that obtains in step a.
The method of above-mentioned preparing cyclohexanol by cyclohexene hydration reaction wherein, separates through filter the reactor cycles use that the described solids that obtains returns to described step a in described step b.
The method of above-mentioned preparing cyclohexanol by cyclohexene hydration reaction, wherein, in described steps d, the first rectifying separation tower operates under normal pressure or reduced pressure, and working pressure is 0.03-0.1MPa, and tower top temperature is 45-85 ℃.
The method of above-mentioned preparing cyclohexanol by cyclohexene hydration reaction, wherein, in described step e, the second rectifying separation tower operates under normal pressure or reduced pressure, and working pressure is 0.04-0.1MPa, and tower top temperature is 55-85 ℃.
The method of above-mentioned preparing cyclohexanol by cyclohexene hydration reaction, wherein, in described step a, catalyzer is selected from mineral acid, Phenylsulfonic acid, strong-acid ion exchange resin or molecular sieve catalyst, is preferably aluminium silicon salt catalyst, for example ZSM-5 (SiO
2/ Al
2O
3>20), form is Powdered crystal grain.
The method of above-mentioned preparing cyclohexanol by cyclohexene hydration reaction, wherein, in described step a, the temperature of reactor is 70-150 ℃, is preferably 100-130 ℃.
The method of above-mentioned preparing cyclohexanol by cyclohexene hydration reaction, wherein, in described step a, the pressure of reactor is 0.1-1.0MPa (gauge pressure), is preferably 0.4-0.6MPa (gauge pressure).
The method of above-mentioned preparing cyclohexanol by cyclohexene hydration reaction, wherein, in described step a, hydration reaction is carried out under inert atmosphere, and gas is selected from nitrogen, helium, argon gas or carbonic acid gas.
The method of above-mentioned preparing cyclohexanol by cyclohexene hydration reaction, wherein, in described step a reactor, the content of oxygen is less than 100ppm, preferably less than 20ppm.
The method of preparing cyclohexanol by cyclohexene hydration reaction of the present invention, adopt the light constituent that contains tetrahydrobenzene of the first rectifying separation column overhead to extract as extraction agent in the extraction phase splitter water after the profit phase splitter separates, the hexalin of aqueous phase dissolving is extracted, afterwards again with the water Returning reacting system, because cyclohexene hydration reaction is reversible reaction, can avoid like this being dissolved with the direct Returning reacting system of water of hexalin and the per pass conversion that reduces hydration reaction.still can carry a certain amount of hydration catalyst secretly in oil phase after the profit phase splitter separates, because this hydration catalyst also has dehydrating function, in follow-up tetrahydrobenzene-hexalin rectifying separation process, along with steaming of tetrahydrobenzene, hexalin easily shifts and the yield of reduction hexalin to tetrahydrobenzene balance direction under the effect of catalyzer, in the present invention, oil phase after the profit phase splitter separates is filtered, can isolate granules of catalyst, can avoid dehydration of cyclohexanol to generate tetrahydrobenzene, improved the yield of hexalin, and can fully recycle catalyzer, reduce the loss of catalyzer, prevent the generation of equipment scaling problem in follow-up rectifying separation operation.Preparing cyclohexanol by cyclohexene hydration reaction can produce the by products such as two hexamethylene ethers, and hexalin of the present invention is from the second rectifying separation tower middle part extraction, can prevent that the by product such as heavy constituent two hexamethylene ethers is contained in the hexalin product, has improved the purity of hexalin product.
The method of preparing cyclohexanol by cyclohexene hydration reaction of the present invention, can make the high purity cyclohexanol product, more than purity reached 99.6% (weight), the selectivity of hexalin was more than 99%, the loss of catalyzer can be reduced by method of the present invention, and equipment scaling can be prevented.
Description of drawings
Fig. 1 is the process flow sheet of preparing cyclohexanol by cyclohexene hydration reaction of the present invention.
Embodiment
Describe the present invention in detail below in conjunction with drawings and Examples.
Embodiment 1
As shown in Figure 1, reaction mass tetrahydrobenzene stream thigh 1 is joined in hydration reactor R continuously with water stream 2, tetrahydrobenzene carries out the heterogeneous catalysis hydration reaction under catalyst action, catalyzer adopts strong-acid ion exchange resin to make catalyzer, in reactor, temperature of reaction is 100 ℃, and reaction pressure is 0.4MPa (gauge pressure), adopts nitrogen to keep inert atmosphere in reactor, the content of oxygen is 80ppm, obtains reaction product mixed solution stream thigh 3 through hydration reaction.
The stream thigh 8 that the light component stream thigh 6 of the first rectifying separation column overhead is told loops back recycle in reactor R, and the light constituent of rectifying tower T1 tower top discharging on a small quantity obtains stream thigh 16, to discharge a small amount of impurity.The working pressure of the first rectifying separation tower is 0.05MPa, and tower top temperature is 56 ℃.The tower reactor stream strands 13 that the tower reactor of the first rectifying separation tower T1 obtains containing hexalin enters into Second distillation column T2 and carries out rectifying separation, the working pressure of the second rectifying separation tower T2 is 0.06MPa, tower top temperature is 60 ℃, the stream thigh 14 that contains tetrahydrobenzene that the second rectifying separation tower T2 tower top obtains returns in the first rectifying tower T1, the tower reactor that obtains hexalin product flow thigh 15, the second rectifying separation tower T2 from the second rectifying separation tower T2 middle part extraction is discharged restructuring shunting thigh 17.
More than the hexalin product purity that the present embodiment makes can reach 99.6% (weight), the selectivity of hexalin reached 99.6%.
As shown in Figure 1, reaction mass tetrahydrobenzene stream thigh 1 is joined in hydration reactor R continuously with water stream 2, tetrahydrobenzene carries out the heterogeneous catalysis hydration reaction under catalyst action, catalyzer adopts the ZSM-5 molecular sieve catalyzer, in reactor, temperature of reaction is 130 ℃, and reaction pressure is 0.6MPa (gauge pressure), adopts helium to keep inert atmosphere in reactor, the content of oxygen is 20ppm, obtains reaction product mixed solution stream thigh 3 through hydration reaction.
The stream thigh 8 that the light component stream thigh 6 of the first rectifying separation column overhead is told loops back recycle in reactor R, and the light constituent of rectifying tower T1 tower top discharging on a small quantity obtains stream thigh 16, to discharge a small amount of impurity.The working pressure of the first rectifying separation tower is 0.03MPa, and tower top temperature is 45 ℃.The tower reactor stream strands 13 that the tower reactor of the first rectifying separation tower T1 obtains containing hexalin enters into Second distillation column T2 and carries out rectifying separation, the working pressure of the second rectifying separation tower T2 is 0.04MPa, tower top temperature is 55 ℃, the stream thigh 14 that contains tetrahydrobenzene that the second rectifying separation tower T2 tower top obtains returns in the first rectifying tower T1, the tower reactor that obtains hexalin product flow thigh 15, the second rectifying separation tower T2 from the second rectifying separation tower T2 middle part extraction is discharged restructuring shunting thigh 17.
More than the hexalin product purity that the present embodiment makes can reach 99.7% (weight), the selectivity of hexalin reached 99.2%.
As shown in Figure 1, reaction mass tetrahydrobenzene stream thigh 1 is joined in hydration reactor R continuously with water stream 2, tetrahydrobenzene carries out the heterogeneous catalysis hydration reaction under catalyst action, catalyzer adopts the ZSM-5 molecular sieve catalyzer, in reactor, temperature of reaction is 70 ℃, and reaction pressure is 0.1MPa (gauge pressure), adopts argon gas to keep inert atmosphere in reactor, the content of oxygen is 50ppm, obtains reaction product mixed solution stream thigh 3 through hydration reaction.
The stream thigh 8 that the light component stream thigh 6 of the first rectifying separation column overhead is told loops back recycle in reactor R, and the light constituent of rectifying tower T1 tower top discharging on a small quantity obtains stream thigh 16, to discharge a small amount of impurity.The working pressure of the first rectifying separation tower is 0.04MPa, and tower top temperature is 51 ℃.The tower reactor stream strands 13 that the tower reactor of the first rectifying separation tower T1 obtains containing hexalin enters into Second distillation column T2 and carries out rectifying separation, the working pressure of the second rectifying separation tower T2 is 0.05MPa, tower top temperature is 59 ℃, the stream thigh 14 that contains tetrahydrobenzene that the second rectifying separation tower T2 tower top obtains returns in the first rectifying tower T1, the tower reactor that obtains hexalin product flow thigh 15, the second rectifying separation tower T2 from the second rectifying separation tower T2 middle part extraction is discharged restructuring shunting thigh 17.
More than the hexalin product purity that the present embodiment makes can reach 99.7% (weight), the selectivity of hexalin reached 99.7%.
As shown in Figure 1, reaction mass tetrahydrobenzene stream thigh 1 is joined in hydration reactor R continuously with water stream 2, tetrahydrobenzene carries out the heterogeneous catalysis hydration reaction under catalyst action, catalyzer adopts the ZSM-5 molecular sieve catalyzer, in reactor, temperature of reaction is 150 ℃, and reaction pressure is 1.0MPa (gauge pressure), adopts carbonic acid gas to keep inert atmosphere in reactor, the content of oxygen is 20ppm, obtains reaction product mixed solution stream thigh 3 through hydration reaction.
The stream thigh 8 that the light component stream thigh 6 of the first rectifying separation column overhead is told loops back recycle in reactor R, and the light constituent of rectifying tower T1 tower top discharging on a small quantity obtains stream thigh 16, to discharge a small amount of impurity.The working pressure of the first rectifying separation tower is 0.1MPa, and tower top temperature is 85 ℃.The tower reactor stream strands 13 that the tower reactor of the first rectifying separation tower T1 obtains containing hexalin enters into Second distillation column T2 and carries out rectifying separation, the working pressure of the second rectifying separation tower T2 is 0.1MPa, tower top temperature is 85 ℃, the stream thigh 14 that contains tetrahydrobenzene that the second rectifying separation tower T2 tower top obtains returns in the first rectifying tower T1, the tower reactor that obtains hexalin product flow thigh 15, the second rectifying separation tower T2 from the second rectifying separation tower T2 middle part extraction is discharged restructuring shunting thigh 17.
More than the hexalin product purity that the present embodiment makes can reach 99.6% (weight), the selectivity of hexalin reached 99.7%.
As shown in Figure 1, reaction mass tetrahydrobenzene stream thigh 1 is joined in hydration reactor R continuously with water stream 2, tetrahydrobenzene carries out the heterogeneous catalysis hydration reaction under catalyst action, catalyzer adopts the ZSM-5 molecular sieve catalyzer, in reactor, temperature of reaction is 120 ℃, and reaction pressure is 0.5MPa (gauge pressure), adopts carbonic acid gas to keep inert atmosphere in reactor, the content of oxygen is 15ppm, obtains reaction product mixed solution stream thigh 3 through hydration reaction.
The stream thigh 8 that the light component stream thigh 6 of the first rectifying separation column overhead is told loops back recycle in reactor R, and the light constituent of rectifying tower T1 tower top discharging on a small quantity obtains stream thigh 16, to discharge a small amount of impurity.The working pressure of the first rectifying separation tower is 0.08MPa, and tower top temperature is 70 ℃.The tower reactor stream strands 13 that the tower reactor of the first rectifying separation tower T1 obtains containing hexalin enters into Second distillation column T2 and carries out rectifying separation, the working pressure of the second rectifying separation tower T2 is 0.09MPa, tower top temperature is 78 ℃, the stream thigh 14 that contains tetrahydrobenzene that the second rectifying separation tower T2 tower top obtains returns in the first rectifying tower T1, the tower reactor that obtains hexalin product flow thigh 15, the second rectifying separation tower T2 from the second rectifying separation tower T2 middle part extraction is discharged restructuring shunting thigh 17.
More than the hexalin product purity that the present embodiment makes can reach 99.7% (weight), the selectivity of hexalin reached 99.6%.
Comparative Examples 1
Adopt experimental installation and the method identical with embodiment 1, remove the filter F device in processing method, the hexalin yield is compared with embodiment 1 and is reduced by 2.0%.
Comparative Examples 2
Adopt experimental installation and the method identical with embodiment 1, remove extraction phase splitter S2 in processing method, the cyclohexene conversion rate is compared with embodiment 1 and is reduced by 1.5%.
Claims (13)
1. the method for a preparing cyclohexanol by cyclohexene hydration reaction, comprise the steps:
A) tetrahydrobenzene and water are carried out the heterogeneous catalysis hydration reaction in hydration reactor under catalyst action, the reaction product mixed solution that obtains carries out phase-splitting in the profit phase splitter, make oil phase and aqueous phase separation;
B) separate through the profit phase splitter oil phase that obtains in step a and enter strainer, isolate the solidss such as catalyzer;
C) separate through the profit phase splitter water that obtains in step a and enter the extraction phase splitter, enter into the light constituent that contains tetrahydrobenzene of extraction phase splitter as extraction agent by the first rectifying tower top in steps d, the hexalin of described aqueous phase dissolving is extracted, the reactor cycles that the water that obtains through the separation of extraction phase splitter turns back in step a is used, and the strainer that the oil phase that extraction obtains enters into step b filters;
D) oil phase that is filtered in step b enters the first rectifying separation tower and carries out rectifying separation, and the light constituent part that contains tetrahydrobenzene that tower top obtains enters into the extraction phase splitter of step c, and a part is returned in the reactor of described step a and recycled;
E) the tower reactor material that contains hexalin that obtains at the bottom of the first rectifying tower in steps d enters the second rectifying separation tower, the light constituent that contains tetrahydrobenzene that the second rectifying separation column overhead obtains returns to the first rectifying separation tower, and the product hexalin is from the second rectifying separation tower middle part extraction.
2. the light constituent that contains tetrahydrobenzene from the first rectifying separation column overhead that the method for claim 1, wherein enters the extraction phase splitter in described step c be 0.1-2 from the mass flux ratio of separating through the profit phase splitter water that obtains in step a.
3. method as claimed in claim 1 or 2, wherein, separate through filter the reactor cycles use that the described solids that obtains returns to described step a in described step b.
4. method as claimed in claim 1 or 2, wherein, in described steps d, the working pressure of the first rectifying separation tower is 0.03-0.1MPa, tower top temperature is 45-85 ℃.
5. method as claimed in claim 1 or 2, wherein, in described step e, the working pressure of the second rectifying separation tower is 0.04-0.1MPa, tower top temperature is 55-85 ℃.
6. method as claimed in claim 1 or 2, wherein, in described step a, catalyzer is selected from mineral acid, Phenylsulfonic acid, strong-acid ion exchange resin or molecular sieve catalyst.
7. method as claimed in claim 1 or 2, wherein, in described step a, the temperature of reactor is 70~150 ℃.
8. method as claimed in claim 7, wherein, in described step a, the temperature of reactor is 100~130 ℃.
9. method as claimed in claim 1 or 2, wherein, in described step a, the pressure of reactor is 0.1~1.0MPa gauge pressure.
10. method as claimed in claim 9, wherein, in described step a, the pressure of reactor is 0.4~0.6MPa gauge pressure.
11. method as claimed in claim 1 or 2, wherein, in described step a, hydration reaction is carried out under inert atmosphere, and gas is selected from nitrogen, helium, argon gas or carbonic acid gas.
12. method as claimed in claim 11, wherein, in described step a reactor, the content of oxygen is less than 100ppm.
13. method as claimed in claim 12, wherein, in described step a reactor, the content of oxygen is less than 20ppm.
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CN107118079B (en) * | 2017-07-03 | 2020-11-20 | 郑州大学 | Method for recovering cyclohexanol from cyclohexanol distillation tower residue |
CN108164396B (en) * | 2018-01-04 | 2021-03-16 | 中石化上海工程有限公司 | Method for efficiently separating and refining cyclopentanol |
CN108997081A (en) * | 2018-05-18 | 2018-12-14 | 河北科技大学 | A kind of reaction and rectification device and method of cyclohexene hydration cyclohexanol |
CN112010736B (en) * | 2020-09-27 | 2023-02-03 | 重庆华峰化工有限公司 | Separation and recovery process of cyclohexanol process raw material |
CN113694556A (en) * | 2021-09-30 | 2021-11-26 | 杭州浥能科技有限公司 | Energy-saving device and method for separating cyclohexanol in hydration method |
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CN1639090A (en) * | 2002-03-06 | 2005-07-13 | 巴斯福股份公司 | Method for the production of cyclohexanol from benzole |
CN101284767A (en) * | 2008-05-27 | 2008-10-15 | 浙江大学 | Process for preparing cyclohexanol by cyclohexene hydration reaction |
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CN1639090A (en) * | 2002-03-06 | 2005-07-13 | 巴斯福股份公司 | Method for the production of cyclohexanol from benzole |
CN101284767A (en) * | 2008-05-27 | 2008-10-15 | 浙江大学 | Process for preparing cyclohexanol by cyclohexene hydration reaction |
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