CN105481631A - Rectification method for 1,3-piperlene - Google Patents
Rectification method for 1,3-piperlene Download PDFInfo
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- CN105481631A CN105481631A CN201410482519.8A CN201410482519A CN105481631A CN 105481631 A CN105481631 A CN 105481631A CN 201410482519 A CN201410482519 A CN 201410482519A CN 105481631 A CN105481631 A CN 105481631A
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Abstract
The present invention discloses a rectification method for 1,3-piperlene. The rectification method comprises the following steps: (1) allowing crude 1,3-piperlene to enter the middle part of a reactive distillation column, collecting distillation components containing 1,3-piperlene, cyclopentane and cyclopentene from the top of the reactive distillation column and distillation components containing dicyclopentadiene and heavier components from the bottom of the reactive distillation column through a reactive distillation process; (2) introducing the distillation components containing 1,3-piperlene, cyclopentane and cyclopentene collected from the top of the reactive distillation column obtained in step (1) into an extraction-distillation column, performing extraction-distillation in the presence of extraction solvents, extracting components containing cyclopentane and cyclopentene from the top of the extraction-distillation column, and extracting solvent materials rich in 1,3-piperlene from the column kettle of the extraction-distillation column; and (3) then delivering the solvent materials rich in 1,3-piperlene obtained in step (2) into a desorption column, thereby obtaining high-purity 1,3-piperlene products from the top of the desorption column. The rectification method solves the disadvantages of too many byproducts and inseparable heavier components of a dimerization reactor and insufficient separation efficiency of the ordinary distillation column. The finally obtained 1,3-piperlene products are high in purity and high in yield.
Description
Technical field
The present invention relates to carbon five separation field of petroleum cracking, say further, relate to a kind of process for purification of m-pentadiene.
Background technology
In a considerable amount of C5 fraction of the byproduct in process of petroleum cracking ethene, wherein isoprene, cyclopentadiene and m-pentadiene etc. are all the important source material of organic chemical industry and fine chemistry industry.At present, cracking c_5 separating technology mainly comprises complete-separation process based on separating isoprene and separating cyclopentadiene is main simple separation technique.Complete-separation process generally adopts solvent extraction and separation method separating isoprene, cyclopentadiene and m-pentadiene etc., and solvent conventional in technique has acetonitrile (ACN), dimethyl formamide (DMF), N-Methyl pyrrolidone (NMP) etc.Simple separation technique generally adopts hot dimerization method to isolate dicyclopentadiene.
Main component in the mixing carbon five (hereinafter referred to as coarse piperyene) of the enrichment m-pentadiene obtained by complete-separation process is m-pentadiene, cyclopentenes and pentamethylene, wherein the content of m-pentadiene is between 65 ~ 80wt%, the total content of cyclopentenes and pentamethylene is generally at about 18 ~ 25wt%, and other contain 2% right and left rings pentadiene and alkynes.Because m-pentadiene product purity is lower, usually less than 80%, usually can only be used for manufacturing pentadiene resin, comprehensive utilization value is single.If more than further purification to 99%, then can as elastomeric raw material, its value will improve greatly.
Because the boiling point of m-pentadiene and cyclopentenes, pentamethylene, cyclopentadiene is very close, and also have other impurity multiple, the refining purification of m-pentadiene cannot be realized with common distillation technology.Its refining purification can be realized in theory by precise distillation, but the exigent stage number of rectifying tower, require very large reflux ratio during operation, industrially application is very uneconomic.
CN101643379 proposes a kind of preparation method of high purity m-pentadiene, it with the by-product C5 fraction of petroleum cracking ethene for raw material, be polymerized through polymerization tank, enter extraction tower extracting and separating, tower reactor obtains finally entering desorption tower desorb rectifying based on the material of m-pentadiene and extraction agent, obtains highly purified m-pentadiene product.Adopt m-pentadiene >=95% that this technique obtains, but dipolymer reactor side reaction is many, affects m-pentadiene product yield, the heavy constituent simultaneously still containing about 2% in product.
CN1445206 discloses a kind of method of purifying and refining piperyene, m-pentadiene raw material removes carbon more than six heavy constituent through rectifying separation, rectifying tower top material carries out extracting rectifying and removes light constituent, after purifying, m-pentadiene purity is more than 95%, but cyclopentadiene cannot be separated by the method from product, and product yield is lower, be 60 ~ 75%.
In sum, there is the problems such as m-pentadiene purity is not high enough, product recovery rate is low in existing technique.
Summary of the invention
For Problems existing in m-pentadiene process for purification in solution prior art, the invention provides a kind of process for purification of m-pentadiene.Namely solve the more and heavy constituent shortcoming that cannot be separated produced of dipolymer reactor by product, solve again the shortcoming of common rectifying tower separating effect deficiency, the m-pentadiene product purity finally obtained is high, yield is high.
The object of this invention is to provide a kind of process for purification of m-pentadiene.
Comprise:
Coarse piperyene is obtained high purity m-pentadiene product after reactive distillation and extracting rectifying.
Comprise the following steps:
(1) coarse piperyene enters in the middle part of reactive distillation column, comprises the logistics of m-pentadiene, pentamethylene and cyclopentenes through reactive distillation processes from overhead extraction, and at the bottom of tower, extraction comprises the logistics of dicyclopentadiene and heavy constituent;
Described reactive distillation processes refers to, in rectifying, the process that cyclopentadiene becomes the reaction of dicyclopentadiene occurs;
(2) the reactive distillation column overhead fraction comprising m-pentadiene, pentamethylene and cyclopentenes step (1) obtained introduces extractive distillation column, extracting rectifying is carried out under the existence of extraction solvent, comprise pentamethylene, cyclopentenes component from overhead extraction, the solvent material being rich in m-pentadiene sends into desorption tower from tower reactor extraction;
The extraction agent adopted is dimethyl formamide, N-Methyl pyrrolidone or acetonitrile;
(3) extractive distillation column kettle material step (2) obtained sends into desorption tower, and tower top obtains highly purified m-pentadiene product, and the extraction agent of tower reactor extraction returns extractive distillation column recycle.
Wherein,
Described reactive distillation column theoretical plate number 50 ~ 140 pieces, working pressure is 0.1 ~ 0.5MPaG, and tower top temperature is 55 ~ 100 DEG C, and bottom temperature is 80 ~ 130 DEG C, and reflux ratio is 2 ~ 15; Preferred: the number of theoretical plate of described reactive distillation column is 60 ~ 120 pieces, and working pressure is 0.15 ~ 0.4MPaG, and tower top temperature is 65 ~ 85 DEG C, and bottom temperature is 95 ~ 120 DEG C, and reflux ratio is 4 ~ 10; The design residence time of every block column plate of described reactive distillation column is 20 ~ 40s; Described reactive distillation column is preferably plate distillation column;
Described extractive distillation column theoretical plate number 50 ~ 120 pieces, working pressure is 0 ~ 0.3MPaG, and tower top temperature is 40 ~ 80 DEG C, and bottom temperature is 100 ~ 170 DEG C, and reflux ratio is 1 ~ 10; Preferred: the number of theoretical plate of described extractive distillation column is 60 ~ 100 pieces, and working pressure is 0.02 ~ 0.15MPaG, tower top temperature 45 ~ 60 DEG C, bottom temperature 110 ~ 150 DEG C, and reflux ratio is 3 ~ 7;
Described desorption tower working pressure is 0.02 ~ 0.1MPaG, bottom temperature 150 ~ 170 DEG C, and reflux ratio is 1 ~ 5.
In step (2), extraction agent is 3:1 ~ 12:1 with the mass ratio of the material entering extractive distillation column, is preferably 5:1 ~ 10:1.
Concrete technical scheme is as follows:
A process for purification for high purity m-pentadiene, comprises the following steps:
(1) coarse piperyene enters in the middle part of reactive distillation column, comprise the logistics of m-pentadiene, pentamethylene and cyclopentenes from overhead extraction through reactive distillation processes, at the bottom of tower, extraction comprises the logistics of dicyclopentadiene and heavy constituent, described reactive distillation column is plate distillation column, there are 50 ~ 140 pieces of number of theoretical plates, working pressure is 0.1 ~ 0.5MPaG, tower top temperature is 55 ~ 100 DEG C, bottom temperature is 80 ~ 130 DEG C, reflux ratio is 2 ~ 15, and described reactive distillation processes refers to, in rectifying, the process that cyclopentadiene becomes the reaction of dicyclopentadiene occurs.
(2) the reactive distillation column overhead fraction comprising m-pentadiene, pentamethylene and cyclopentenes step (1) obtained introduces extractive distillation column, extracting rectifying is carried out under the existence of extraction solvent, comprise pentamethylene, cyclopentenes component from overhead extraction, the solvent material being rich in m-pentadiene sends into desorption tower from tower reactor extraction.Described extractive distillation column number of theoretical plate 50 ~ 120 pieces, working pressure is 0 ~ 0.3MPaG, and tower top temperature is 40 ~ 80 DEG C, and bottom temperature is 100 ~ 170 DEG C, and reflux ratio is 1 ~ 10.Extractant feed is 3:1 ~ 12:1 with the mass ratio of the material entering extractive distillation column, and the extraction agent adopted is dimethyl formamide, N-Methyl pyrrolidone or acetonitrile.
(3) extractive distillation column kettle material step (2) obtained sends into desorption tower, and tower top obtains highly purified m-pentadiene product, and the extraction agent of tower reactor extraction returns extractive distillation column recycle.
In the step (1) of method of the present invention, make full use of the principle of reactive distillation, in above-mentioned reactive distillation column, cyclopentadiene generation dimerization reaction generates dicyclopentadiene, utilize boiling-point difference dicyclopentadiene to be separated rapidly with other carbon five components simultaneously, thus realization response be separated the object of simultaneously carrying out.
C
5there are following 3 class reactions in the diolefin in cut: 1. from dimerization reaction: comprise the diolefins such as cyclopentadiene, m-pentadiene, isoprene and be polymerized to dimer from two, wherein cyclopentadiene generates dicyclopentadiene from dimerization reaction is main reaction, m-pentadiene and isoprene to generate dimer from dimerization reaction be side reaction; 2. dimerization reaction: it is side reaction that cyclopentadiene and m-pentadiene, dimerization reaction between cyclopentadiene and isoprene generate codimerization thing; 3. poly reaction: the dimer generated from dimerization, dimerization reaction and codimers generate plural polymer with diolefin reaction further, until generate the larger polymer of molecular weight.
The relative volatility that different solvents exists lower C5 hydrocarbon is as shown in table 1.Therefrom can find out, cyclopentadiene and m-pentadiene boiling point close, relative volatility difference is very little in the absence of solvent, conventional distillation is difficult to be separated, and cyclopentadiene is more soluble in solvent than m-pentadiene when there being solvent, adopt the method for one-time extractive rectification can remove the components such as the high isopentene of relative volatility, pentamethylene, cyclopentenes, but cyclopentadiene cannot remove from m-pentadiene product.Adopt dipolymer reactor to be stripped of most cyclopentadiene in CN101643379, but polymerization reaction time is long, need 24 ~ 36 hours, side reaction is more, and heavy constituent is not separated.CN1445206 adopts common rectifying tower separation removal carbon more than six heavy constituent, and cyclopentadiene is not separated, and as cyclopentadiene too high levels in coarse piperyene, then product purity declines.Above two kinds of techniques all restrict the refining further of m-pentadiene, cannot reach more than 99% purity.
There is the relative volatility of lower C5 hydrocarbon in table 1 different solvents
In the method for the invention, make full use of the effect of reactive distillation, the dicyclopentadiene that cyclopentadiene generation dimerization reaction generates moves toward reactive distillation column tower reactor, thus makes the concentration of tower top cyclopentadiene be tending towards very low.Because reactive distillation column rectifying section is lower relative to dimerization reaction actuator temperature, the residence time is shorter, and m-pentadiene, in the process toward tower top movement, effectively reduces the generation from dimerization side reaction, improves the yield of m-pentadiene product.The dipolymer that carbon more than six heavy constituent and reaction generate removes from tower reactor by simultaneous reactions rectifying tower, improves the purity of m-pentadiene product.
In the method for the invention, namely solve the more and heavy constituent shortcoming that cannot be separated produced of dipolymer reactor by product, solve again the shortcoming of common rectifying tower separating effect deficiency, the m-pentadiene product purity finally obtained is high, yield is high.
Two be polymerized to dicyclopentadiene and reduce the generation of other dipolymers in this tower to make cyclopentadiene as far as possible, need the plate distillation column selecting the residence time comparatively suitable, adopt the column plate being conducive to reactive distillation, such as, increase overflow weir or adopt vertical sieve plate column etc.
In sum, the present invention adopts the method for reactive distillation, combines the advantage of dipolymer reactor of the prior art and rectifying tower, and technical process is simple, and stable operation, is easy to industrialization.Coarse piperyene carries out purification through the flow process of first reactive distillation extracting rectifying again, and the purity of the high purity m-pentadiene after refining is more than 99%, and the yield of product is more than 90%.
Accompanying drawing explanation
Fig. 1 is the schematic flow sheet of m-pentadiene process for purification of the present invention;
Description of reference numerals:
1 reactive distillation column; 2 extractive distillation columns; 3 desorption towers; 4 coarse piperyenes;
5 dicyclopentadiene and heavy constituent; 6 pentamethylene and cyclopentenes; 7 extraction solvents;
8 high purity m-pentadiene products
Embodiment
Below in conjunction with embodiment, further illustrate the present invention.
Embodiment 1:
Coarse piperyene enters reactive distillation column, and reactive distillation column is 100 pieces of theoretical stages, and working pressure is 0.25MPaG, and tower top temperature is 78.3 DEG C, and bottom temperature is 115.3 DEG C, and reflux ratio is 8.At the bottom of tower, isolate dicyclopentadiene and heavy constituent, tower top light constituent enters in the middle part of extractive distillation column.
Extraction agent dimethyl formamide enters extractive distillation column from tower top, and extractant feed is 8:1 with the mass ratio of the material entering extractive distillation column, and extractive distillation column is 100 pieces of theoretical stages, working pressure is 0.02MPaG, tower top temperature is 50.3 DEG C, and bottom temperature is 123.3 DEG C, and reflux ratio is 6.Extracting rectifying tower top isolates the high material of the relative volatilities such as pentamethylene, cyclopentenes, 2-amylene, isopentene, isoprene, and the rich solvent absorbing m-pentadiene enters desorption tower desorb.
Desorption tower working pressure is 0.02MPaG, and bottom temperature is 161 DEG C, and reflux ratio is 2.The extraction agent that tower reactor obtains returns extractive distillation column recycle, and the high purity m-pentadiene product purity that tower top obtains is 99.5%, and yield is 90.5%.
Embodiment 2:
Coarse piperyene enters reactive distillation column, and reactive distillation column is 60 pieces of theoretical stages, and working pressure is 0.15MPaG, and tower top temperature is 73.2 DEG C, and bottom temperature is 103.3 DEG C, and reflux ratio is 5.At the bottom of tower, isolate dicyclopentadiene and heavy constituent, tower top light constituent enters in the middle part of extractive distillation column.
Extraction agent dimethyl formamide enters extractive distillation column from tower top, and extractant feed is 6:1 with the mass ratio of the material entering extractive distillation column, and extractive distillation column is 80 pieces of theoretical stages, working pressure is 0.1MPaG, tower top temperature is 58.5 DEG C, and bottom temperature is 140.3 DEG C, and reflux ratio is 6.Extracting rectifying tower top isolates the high material of the relative volatilities such as pentamethylene, cyclopentenes, 2-amylene, isopentene, isoprene, and the rich solvent absorbing m-pentadiene enters desorption tower desorb.
Desorption tower working pressure is 0.05MPaG, and bottom temperature is 168 DEG C, and reflux ratio is 1.The extraction agent that tower reactor obtains returns extractive distillation column recycle, and the high purity m-pentadiene product purity that tower top obtains is 99.1%, and yield is 93.2%.
Claims (8)
1. a process for purification for m-pentadiene, is characterized in that described method comprises:
Coarse piperyene is obtained high purity m-pentadiene product after reactive distillation and extracting rectifying.
2. the process for purification of m-pentadiene as claimed in claim 1, is characterized in that described method comprises:
(1) coarse piperyene enters in the middle part of reactive distillation column, comprises the logistics of m-pentadiene, pentamethylene and cyclopentenes through reactive distillation processes from overhead extraction, and at the bottom of tower, extraction comprises the logistics of dicyclopentadiene and heavy constituent;
Described reactive distillation processes refers to, in rectifying, the process that cyclopentadiene becomes the reaction of dicyclopentadiene occurs;
(2) the reactive distillation column overhead fraction comprising m-pentadiene, pentamethylene and cyclopentenes step (1) obtained introduces extractive distillation column, extracting rectifying is carried out under the existence of extraction solvent, comprise pentamethylene, cyclopentenes component from overhead extraction, the solvent material being rich in m-pentadiene sends into desorption tower from tower reactor extraction;
The extraction agent adopted is dimethyl formamide, N-Methyl pyrrolidone or acetonitrile;
(3) extractive distillation column kettle material step (2) obtained sends into desorption tower, and tower top obtains highly purified m-pentadiene product, and the extraction agent of tower reactor extraction returns extractive distillation column recycle.
3. the process for purification of m-pentadiene as claimed in claim 2, is characterized in that:
Described reactive distillation column theoretical plate number 50 ~ 140 pieces, working pressure is 0.1 ~ 0.5MPaG, and tower top temperature is 55 ~ 100 DEG C, and bottom temperature is 80 ~ 130 DEG C, and reflux ratio is 2 ~ 15;
Described extractive distillation column theoretical plate number 50 ~ 120 pieces, working pressure is 0 ~ 0.3MPaG, and tower top temperature is 40 ~ 80 DEG C, and bottom temperature is 100 ~ 170 DEG C, and reflux ratio is 1 ~ 10.
4. the process for purification of m-pentadiene as claimed in claim 3, is characterized in that:
Described reactive distillation column is plate distillation column.
5. the process for purification of m-pentadiene as claimed in claim 2, is characterized in that:
In step (2), extraction agent is 3:1 ~ 12:1 with the mass ratio of the material entering extractive distillation column.
6. the process for purification of m-pentadiene as claimed in claim 5, is characterized in that:
Extraction agent is 5:1 ~ 10:1 with the mass ratio of the material entering extractive distillation column.
7. the process for purification of m-pentadiene as claimed in claim 3, is characterized in that:
The number of theoretical plate of described reactive distillation column is 60 ~ 120 pieces, and working pressure is 0.15 ~ 0.4MPaG, and tower top temperature is 65 ~ 85 DEG C, and bottom temperature is 95 ~ 120 DEG C, and reflux ratio is 4 ~ 10;
The number of theoretical plate of described extractive distillation column is 60 ~ 100 pieces, and working pressure is 0.02 ~ 0.15MPaG, tower top temperature 45 ~ 60 DEG C, bottom temperature 110 ~ 150 DEG C, and reflux ratio is 3 ~ 7;
Described desorption tower working pressure is 0.02 ~ 0.1MPaG, bottom temperature 150 ~ 170 DEG C, and reflux ratio is 1 ~ 5.
8. the process for purification of m-pentadiene as claimed in claim 7, is characterized in that:
The design residence time of every block column plate of described reactive distillation column is 20 ~ 40s.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112368253A (en) * | 2018-09-05 | 2021-02-12 | 日本瑞翁株式会社 | Process for producing piperylene |
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| CN112368253A (en) * | 2018-09-05 | 2021-02-12 | 日本瑞翁株式会社 | Process for producing piperylene |
| US11905242B2 (en) | 2018-09-05 | 2024-02-20 | Zeon Corporation | Method of producing piperylene |
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