CN102134177A - Method for separating cyclohexane and cyclohexene by extraction and rectification - Google Patents
Method for separating cyclohexane and cyclohexene by extraction and rectification Download PDFInfo
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Abstract
The invention discloses a method for separating cyclohexane and cyclohexene by extraction and rectification, which comprises the following steps of: a) performing extraction and rectification on the mixed solution of the cyclohexane and the cyclohexene in an extraction and rectification tower, wherein the extraction agent is sulfolane, the cyclohexane is obtained at the top of the tower, and rich solvent solution of the cyclohexene and the sulfolane extraction agent is obtained at the bottom of the tower; and b) delivering the rich solvent solution obtained at the bottom of the extraction and rectification tower to a solvent recovery tower, wherein the cyclohexene is obtained at the top of the solvent recovery tower, and the reclaimed sulfolane extraction agent obtained at the bottom of the tower is returned to the step a) to recycle. By the separation method, high-purity cyclohexane and cyclohexene products can be obtained, the extraction agent can be recycled by reclaiming, the separation efficiency can be improved, and equipment investment and process energy consumption are remarkably reduced.
Description
Technical field
The present invention relates to a kind of extraction and rectification separation method, particularly relate to the method for a kind of extracting rectifying separating benzene-cyclohexane and tetrahydrobenzene.
Background technology
Along with current synthon and polymeric amide industrial expansion, the benzene partial hydrogenation prepares tetrahydrobenzene becomes an important research direction in the chemical field in recent years, hexanaphthene that relates in the technology and tetrahydrobenzene are very important organic compound, its boiling point is respectively 80.7 ℃ and 83 ℃, relative volatility is about 1.15, belongs to nearly boiling point system.Processing requirement is separated to product more than the 99.0%wt respectively with it, if its theoretical number of plates of rectifying tower surpasses more than 150 when adopting conventional distillation to separate, operating reflux ratio is up to 20, so that the energy consumption of whole sepn process is very high and investment is bigger.
It is the method for raw material production pimelinketone with the coking benzene that Chinese patent CN200910075129.9 discloses a kind of, process using N, the N-N,N-DIMETHYLACETAMIDE is as extraction agent separating benzene-cyclohexane and tetrahydrobenzene, extraction agent and raw material ratio are 6: 1, operating reflux ratio was up to 10: 1, can obtain above hexanaphthene of 99.5wt% and the above tetrahydrobenzene of 99.0wt%, obvious reflux ratio of this technology and extractant feed are bigger, and the energy consumption of whole process is the bottleneck of its technology.
U.S. Pat 4734536 discloses company of a kind of Japanese Asahi Chemical Industry and has carried out partial hydrogenation and prepare in the technology of tetrahydrobenzene, also be to adopt N, the N-N,N-DIMETHYLACETAMIDE is as extraction agent separating benzene-cyclohexane and tetrahydrobenzene, pass through operation conditions optimization, its extraction agent and raw material charge ratio are 8: 1, operating reflux ratio obtained above hexanaphthene of 99.8wt% and the above tetrahydrobenzene of 99.8%wt up to 9: 1, and the unit consumption cost of this technology operation is still bigger.
Document (petrochemical complex, 2001,30 (4): disclose the novel solvent selection scheme that hexanaphthene-tetrahydrobenzene-benzene system carries out extracting rectifying 285-290), intend determining N by research, the N-pyrrolidone separates above system with gamma-butyrolactone as extraction agent and has higher separation efficiency, but its technology still is in the laboratory study stage.
Along with the development of current energy-saving and emission-reduction and low-carbon economy, the energy consumption index in the chemical process has become the economic target of any one chemical enterprise first concern.Separates in view of hexanaphthene and tetrahydrobenzene are difficult, the present situation of high energy consumption, the separating technology of being badly in need of developing a kind of high-efficiency low energy consumption makes hexanaphthene can separate effectively with tetrahydrobenzene.
Summary of the invention
The technical problem to be solved in the present invention provides the method for a kind of extracting rectifying separating benzene-cyclohexane and tetrahydrobenzene system, to obtain highly purified hexanaphthene and tetrahydrobenzene product, extraction agent can recycle through reclaiming, this processing method can improve separation efficiency, significantly reduces facility investment and process energy consumption.
For solving the problems of the technologies described above, the invention provides the method for a kind of extracting rectifying separating benzene-cyclohexane and tetrahydrobenzene, comprise the steps:
A) hexanaphthene and tetrahydrobenzene mixed solution are carried out extracting rectifying in extractive distillation column, extraction agent is a tetramethylene sulfone, and cat head obtains hexanaphthene, obtains the rich solvent solution of tetrahydrobenzene and extraction agent tetramethylene sulfone at the bottom of the tower;
B) the rich solvent solution that obtains at the bottom of the extracting rectifying Tata in the described step a) enters solvent recovery tower, and the solvent recuperation column overhead obtains tetrahydrobenzene, and the extraction agent tetramethylene sulfone that recovery obtains at the bottom of the tower returns among the described step a and recycles.
The method of above-mentioned extracting rectifying separating benzene-cyclohexane and tetrahydrobenzene, wherein, to enter the temperature of extractive distillation column be 75.0-85.0 ℃ to the extraction agent tetramethylene sulfone among the described step a, is preferably 80.0 ℃.
The method of above-mentioned extracting rectifying separating benzene-cyclohexane and tetrahydrobenzene, wherein, hexanaphthene and tetrahydrobenzene mixed solution add the tower from the extractive distillation column middle part among the described step a, and the extraction agent tetramethylene sulfone adds the tower near top of tower from extractive distillation column; Rich solvent solution adds the tower from the solvent recovery tower middle part among the described step b.
The method of above-mentioned extracting rectifying separating benzene-cyclohexane and tetrahydrobenzene, wherein, the solvent ratio of extraction agent tetramethylene sulfone and hexanaphthene and tetrahydrobenzene mixed solution is 2.5～3.0: 1 among the described step a, be preferably 3.0: 1, indication solvent ratio of the present invention is the volume ratio of extraction agent tetramethylene sulfone and hexanaphthene and tetrahydrobenzene mixed solution.
The method of above-mentioned extracting rectifying separating benzene-cyclohexane and tetrahydrobenzene, wherein, the theoretical plate number of extractive distillation column is 65～75 among the described step a, is preferably 70, the cat head working pressure is 30.0～40.0KPa, be preferably 30.0KPa, reflux ratio is 4.0～5.0: 1, is preferably 4.0: 1, tower top temperature is 75.0～85.0 ℃, be preferably 80.0 ℃, tower still temperature is 190.0～200.0 ℃, is preferably 195.0 ℃.
The method of above-mentioned extracting rectifying separating benzene-cyclohexane and tetrahydrobenzene, wherein, the theoretical plate number of solvent recovery tower is 30～35 among the described step b, is preferably 30, the cat head working pressure is 15.0～20.0KPa, be preferably 20.0KPa, reflux ratio is 0.5～1: 1, is preferably 1: 1, tower top temperature is 74.0～78.0 ℃, be preferably 75.0 ℃, tower still temperature is 195.0～205.0 ℃, is preferably 198.0 ℃.
The method of above-mentioned extracting rectifying separating benzene-cyclohexane and tetrahydrobenzene, wherein, the purity of extraction agent tetramethylene sulfone is more than the 99.0wt% among the described step a.
The method of above-mentioned extracting rectifying separating benzene-cyclohexane and tetrahydrobenzene, wherein, the cyclohexane purity that the extracting rectifying column overhead obtains among the described step a is more than the 99.5wt%; The tetrahydrobenzene purity that the solvent recuperation column overhead obtains among the described step b is more than the 99.5wt%.
The method of extracting rectifying separating benzene-cyclohexane of the present invention and tetrahydrobenzene has following beneficial effect:
(1) compare with the process that adopts other extraction agent to carry out extracting rectifying separating benzene-cyclohexane and tetrahydrobenzene with the conventional distillation process, adopt tetramethylene sulfone significantly to reduce as the extracting rectifying separating technology theoretical plate number of extraction agent, facility investment reduces greatly;
(2) operating reflux ratio of extraction rectification technique process and solvent feed make the energy consumption of entire operation process lower than reducing significantly;
(3) separation method technical process of the present invention is simple, can obtain purity at hexanaphthene more than the 99.5wt% and the tetrahydrobenzene product more than the 99.5wt%, has favorable economic benefit and social benefit.
Description of drawings
Fig. 1 is the process flow sheet of extracting rectifying separating benzene-cyclohexane of the present invention and tetrahydrobenzene.
Embodiment
Describe the present invention in detail below in conjunction with drawings and Examples.
The hexanaphthene and the tetrahydrobenzene mixing raw material liquid that adopt certain enterprise to provide among the following embodiment, stock liquid consists of hexanaphthene: 25.0wt%, tetrahydrobenzene: 75.0wt%.
As shown in Figure 1, the hexanaphthene of 1 parts by volume and tetrahydrobenzene mixing raw material liquid F2 are joined the tower from the middle and upper part of extractive distillation column 1, the purity of 3 parts by volume ℃ is joined the tower near the cat head position from extractive distillation column 1 through interchanger 3 heat exchange to 80 at the extraction agent tetramethylene sulfone F1 more than the 99.0wt%, the theoretical plate number of this extractive distillation column 1 is 70, the cat head working pressure is 30.0KPa, tower top temperature is 80 ℃, tower still temperature is 195 ℃, overhead vapours is through condenser 4 condensing refluxes, operating reflux ratio is 4.0: 1, from cat head extraction purity is the hexanaphthene product D1 of 99.8wt%, reboiler 5 provides heat power for extractive distillation column 1, the rich solvent D2 that contains tetramethylene sulfone and tetrahydrobenzene at the bottom of extractive distillation column 1 tower enters into the middle part of solvent recovery tower 2, the theoretical plate number of solvent recovery tower 2 is 30, the cat head working pressure is 20.0KPa, tower top temperature is 75 ℃, tower still temperature is 198 ℃, overhead vapours is through condenser 6 condensing refluxes, operating reflux ratio is 1: 1, from cat head extraction purity is the tetrahydrobenzene product D3 of 99.5wt%, reboiler 7 provides heat power for solvent recovery tower 2, and the extraction agent tetramethylene sulfone D4 that recovery obtains at the bottom of solvent recovery tower 2 towers can turn back among the extractant feed stream F1 and recycle.
In the sepn process of present embodiment, the feed rate of hexanaphthene and tetrahydrobenzene mixing raw material liquid F2 is 1000kg/hr, the thermal load that extractive distillation column reboiler 5 and solvent recovery tower reboiler 7 consume is total up to 2.10MCAL/hr, and the middle pressure steam consumption is total up to 4.8t/h; The refrigeration duty of interchanger 3, condenser 4 and condenser 6 is total up to 1.95MCAL/hr, and cooling water consumption is total up to 160.0t/hr.
As shown in Figure 1, the hexanaphthene of 1 parts by volume and tetrahydrobenzene mixing raw material liquid F2 are joined the tower from the middle and upper part of extractive distillation column 1, the purity of 2.5 parts by volume ℃ is joined the tower near the cat head position from extractive distillation column 1 through interchanger 3 heat exchange to 85 at the extraction agent tetramethylene sulfone F1 more than the 99.0wt%, the theoretical plate number of this extractive distillation column 1 is 75, the cat head working pressure is 35.0KPa, tower top temperature is 84 ℃, tower still temperature is 199 ℃, overhead vapours is through condenser 4 condensing refluxes, operating reflux ratio is 5.0: 1, from cat head extraction purity is the hexanaphthene product D1 of 99.7wt%, reboiler 5 provides heat power for extractive distillation column 1, the rich solvent D2 that contains tetramethylene sulfone and tetrahydrobenzene at the bottom of extractive distillation column 1 tower enters into the middle part of solvent recovery tower 2, the theoretical plate number of solvent recovery tower 2 is 35, the cat head working pressure is 15.0KPa, tower top temperature is 76 ℃, tower still temperature is 202 ℃, overhead vapours is through condenser 6 condensing refluxes, operating reflux ratio is 1: 1, from cat head extraction purity is the tetrahydrobenzene product D3 of 99.6wt%, reboiler 7 provides heat power for solvent recovery tower 2, and the extraction agent tetramethylene sulfone D4 that recovery obtains at the bottom of solvent recovery tower 2 towers can turn back among the extractant feed stream F1 and recycle.
In the separating process of present embodiment, the feed rate of hexanaphthene and tetrahydrobenzene mixing raw material liquid F2 is 2000kg/hr, the thermal load that extractive distillation column reboiler 5 and solvent recovery tower reboiler 7 consume is total up to 4.02MCAL/hr, and the middle pressure steam consumption is total up to 8.78t/h; The refrigeration duty of interchanger 3, condenser 4 and condenser 6 is total up to 3.79MCAL/hr, and cooling water consumption is total up to 310.0t/hr.
As shown in Figure 1, the hexanaphthene of 1 parts by volume and tetrahydrobenzene mixing raw material liquid F2 are joined the tower from the middle and upper part of extractive distillation column 1, the purity of 2.7 parts by volume ℃ is joined the tower near the cat head position from extractive distillation column 1 through interchanger 3 heat exchange to 75 at the extraction agent tetramethylene sulfone F1 more than the 99.0wt%, the theoretical plate number of this extractive distillation column 1 is 65, the cat head working pressure is 30.0KPa, tower top temperature is 75 ℃, tower still temperature is 190 ℃, overhead vapours is through condenser 4 condensing refluxes, operating reflux ratio is 5.0: 1, from cat head extraction purity is the hexanaphthene product D1 of 99.6wt%, reboiler 5 provides heat power for extractive distillation column 1, the rich solvent D2 that contains tetramethylene sulfone and tetrahydrobenzene at the bottom of extractive distillation column 1 tower enters into the middle part of solvent recovery tower 2, the theoretical plate number of solvent recovery tower 2 is 31, the cat head working pressure is 15.0KPa, tower top temperature is 74 ℃, tower still temperature is 195 ℃, overhead vapours is through condenser 6 condensing refluxes, operating reflux ratio is 0.5: 1, from cat head extraction purity is the tetrahydrobenzene product D3 of 99.5wt%, reboiler 7 provides heat power for solvent recovery tower 2, and the extraction agent tetramethylene sulfone D4 that recovery obtains at the bottom of solvent recovery tower 2 towers can turn back among the extractant feed stream F1 and recycle.
In the separating process of present embodiment, the feed rate of hexanaphthene and tetrahydrobenzene mixing raw material liquid F2 is 1000kg/hr, the thermal load that extractive distillation column reboiler 5 and solvent recovery tower reboiler 7 consume is total up to 2.03MCAL/hr, and the middle pressure steam consumption is total up to 4.76t/h; The refrigeration duty of interchanger 3, condenser 4 and condenser 6 is total up to 1.92MCAL/hr, and cooling water consumption is total up to 156.0t/hr.
As shown in Figure 1, the hexanaphthene of 1 parts by volume and tetrahydrobenzene mixing raw material liquid F2 are joined the tower from the middle and upper part of extractive distillation column 1, the purity of 3 parts by volume ℃ is joined the tower near the cat head position from extractive distillation column 1 through interchanger 3 heat exchange to 85 at the extraction agent tetramethylene sulfone F1 more than the 99.0wt%, the theoretical plate number of this extractive distillation column 1 is 75, the cat head working pressure is 40.0KPa, tower top temperature is 85 ℃, tower still temperature is 200 ℃, overhead vapours is through condenser 4 condensing refluxes, operating reflux ratio is 4.0: 1, from cat head extraction purity is the hexanaphthene product D1 of 99.8wt%, reboiler 5 provides heat power for extractive distillation column 1, the rich solvent D2 that contains tetramethylene sulfone and tetrahydrobenzene at the bottom of extractive distillation column 1 tower enters into the middle part of solvent recovery tower 2, the theoretical plate number of solvent recovery tower 2 is 35, the cat head working pressure is 20.0KPa, tower top temperature is 78 ℃, tower still temperature is 205 ℃, overhead vapours is through condenser 6 condensing refluxes, operating reflux ratio is 0.8: 1, from cat head extraction purity is the tetrahydrobenzene product D3 of 99.6wt%, reboiler 7 provides heat power for solvent recovery tower 2, and the extraction agent tetramethylene sulfone D4 that recovery obtains at the bottom of solvent recovery tower 2 towers can turn back among the extractant feed stream F1 and recycle.
In the separating process of present embodiment, the feed rate of hexanaphthene and tetrahydrobenzene mixing raw material liquid F2 is 2000kg/hr, the thermal load that extractive distillation column reboiler 5 and solvent recovery tower reboiler 7 consume is total up to 4.09MCAL/hr, and the middle pressure steam consumption is total up to 8.89t/h; The refrigeration duty of interchanger 3, condenser 4 and condenser 6 is total up to 3.81MCAL/hr, and cooling water consumption is total up to 315.0t/hr.
Claims (10)
1. the method for extracting rectifying separating benzene-cyclohexane and tetrahydrobenzene comprises the steps:
A) hexanaphthene and tetrahydrobenzene mixed solution are carried out extracting rectifying in extractive distillation column, extraction agent is a tetramethylene sulfone, and cat head obtains hexanaphthene, obtains the rich solvent solution of tetrahydrobenzene and extraction agent tetramethylene sulfone at the bottom of the tower;
B) the rich solvent solution that obtains at the bottom of the extracting rectifying Tata in the described step a) enters solvent recovery tower, and the solvent recuperation column overhead obtains tetrahydrobenzene, and the extraction agent tetramethylene sulfone that recovery obtains at the bottom of the tower returns among the described step a and recycles.
2. to enter the temperature of extractive distillation column be 75.0-85.0 ℃ to the extraction agent tetramethylene sulfone among the method for claim 1, wherein described step a.
3. method as claimed in claim 2, wherein, to enter the temperature of extractive distillation column be 80.0 ℃ to the extraction agent tetramethylene sulfone among the described step a.
4. method as claimed in claim 1 or 2, wherein, hexanaphthene and tetrahydrobenzene mixed solution add the tower from the extractive distillation column middle part among the described step a, and the extraction agent tetramethylene sulfone adds the tower near top of tower from extractive distillation column; Rich solvent solution adds the tower from the solvent recovery tower middle part among the described step b.
5. method as claimed in claim 1 or 2, wherein, the solvent ratio of extraction agent tetramethylene sulfone and hexanaphthene and tetrahydrobenzene mixed solution is 2.5～3.0: 1 among the described step a.
6. method as claimed in claim 5, wherein, the solvent ratio of extraction agent tetramethylene sulfone and hexanaphthene and tetrahydrobenzene mixed solution is 3.0: 1 among the described step a.
7. method as claimed in claim 1 or 2, wherein, the theoretical plate number of extractive distillation column is 65～75 among the described step a, is preferably 70, the cat head working pressure is 30.0～40.0KPa, be preferably 30.0KPa, reflux ratio is 4.0～5.0: 1, is preferably 4.0: 1, tower top temperature is 75.0～85.0 ℃, be preferably 80.0 ℃, tower still temperature is 190.0～200.0 ℃, is preferably 195.0 ℃.
8. method as claimed in claim 1 or 2, wherein, the theoretical plate number of solvent recovery tower is 30～35 among the described step b, is preferably 30, the cat head working pressure is 15.0～20.0KPa, be preferably 20.0KPa, reflux ratio is 0.5～1: 1, is preferably 1: 1, tower top temperature is 74.0～78.0 ℃, be preferably 75.0 ℃, tower still temperature is 195.0～205.0 ℃, is preferably 198.0 ℃.
9. method as claimed in claim 1 or 2, wherein, the purity of extraction agent tetramethylene sulfone is more than the 99.0wt% among the described step a.
10. method as claimed in claim 1 or 2, wherein, the cyclohexane purity that the extracting rectifying column overhead obtains among the described step a is more than the 99.5wt%; The tetrahydrobenzene purity that the solvent recuperation column overhead obtains among the described step b is more than the 99.5wt%.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102911139A (en) * | 2012-11-13 | 2013-02-06 | 漆志文 | Recovery and separation method for solvent containing tetrahydrofuran-carbinol system |
| CN106966852A (en) * | 2016-01-14 | 2017-07-21 | 天津大学 | The method that continuous extraction rectifying separates high-carbon n-alkane and normal olefine |
| CN108046974A (en) * | 2017-12-29 | 2018-05-18 | 北京华和拓科技开发有限责任公司 | A kind of Separation of Benzene, hexamethylene, the system and method for cyclohexene |
| CN108083966A (en) * | 2017-12-27 | 2018-05-29 | 中国天辰工程有限公司 | A kind of method of azeotropic distillation separating cyclohexene and 1,3- cyclohexadiene |
| CN114870806A (en) * | 2022-04-19 | 2022-08-09 | 浙江大学 | Application of ion hybrid porous material in separation of cyclohexene and cyclohexane and preparation method thereof |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102911139A (en) * | 2012-11-13 | 2013-02-06 | 漆志文 | Recovery and separation method for solvent containing tetrahydrofuran-carbinol system |
| CN106966852A (en) * | 2016-01-14 | 2017-07-21 | 天津大学 | The method that continuous extraction rectifying separates high-carbon n-alkane and normal olefine |
| CN106966852B (en) * | 2016-01-14 | 2019-10-25 | 天津大学 | The method of continuous extraction rectifying separation high-carbon n-alkane and normal olefine |
| CN108083966A (en) * | 2017-12-27 | 2018-05-29 | 中国天辰工程有限公司 | A kind of method of azeotropic distillation separating cyclohexene and 1,3- cyclohexadiene |
| CN108083966B (en) * | 2017-12-27 | 2021-01-12 | 中国天辰工程有限公司 | Method for separating cyclohexene and 1, 3-cyclohexadiene by azeotropic distillation |
| CN108046974A (en) * | 2017-12-29 | 2018-05-18 | 北京华和拓科技开发有限责任公司 | A kind of Separation of Benzene, hexamethylene, the system and method for cyclohexene |
| CN108046974B (en) * | 2017-12-29 | 2020-10-30 | 烟台中科恩吉科创新产业园管理有限公司 | System and method for separating benzene, cyclohexane and cyclohexene |
| CN114870806A (en) * | 2022-04-19 | 2022-08-09 | 浙江大学 | Application of ion hybrid porous material in separation of cyclohexene and cyclohexane and preparation method thereof |
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Application publication date: 20110727 |