CN102951987B - Separate C5 fraction the method producing dicyclopentadiene - Google Patents
Separate C5 fraction the method producing dicyclopentadiene Download PDFInfo
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Abstract
A kind of separate C5 fraction the method producing dicyclopentadiene, including: raw material C5 fraction removes light component through rectification；The preheated dimerization reaction of material is so that part cyclopentadiene is converted into dicyclopentadiene；Material after preheating dimerization reaction is through rectification separation and Extraction part isoprene, and tower top must be enriched with the material of isoprene；Front kettle material through second time hot dimerization reaction so that remaining cyclopentadiene is converted into dicyclopentadiene；Material is through the remaining isoprene of rectification separation and Extraction, and tower top must be enriched with the material of isoprene, and tower reactor must be enriched with the material of dicyclopentadiene and pentadiene；Front kettle material is through rectification separation dicyclopentadiene and pentadiene, and tower top must be enriched with the material of pentadiene, and tower reactor must be enriched with the material of dicyclopentadiene；Front kettle material must refine dicyclopentadiene product through rectification and purification。It is an advantage of the current invention that separation process isoprene and cyclopentadiene hot dimerization reaction altogether is effectively suppressed, decrease isoprene and cyclopentadiene loss。
Description
Technical field
The present invention relates to the method separating C5 fraction, particularly to by the C5 fraction of petroleum cracking ethylene by-product, by hot dimerization, process obtains isoprene and pentadiene initial gross separation material the method obtaining dicyclopentadiene purified product with rectification separates etc. simultaneously。
Background technology
Going out a kind of C5 fraction by by-product in petroleum cracking process of producing ethylene, in all of cracking of ethylene by-product material, C5 fraction occupies higher proportion。Containing total amount in C5 fraction is the cyclopentadiene of 40～60wt%, isoprene and pentadiene, these three diolefin chemical property is active, can react with gas chromatography, all have been widely used at resin, rubber, medicine or pesticide and other field of fine chemical。At present, separate produce cyclopentadiene, isoprene and pentadiene be C5 fraction main be also the Application way of most economic worth。C5 fraction complicated component, permitted multi-component boiling point close, or easily form azeotropic mixture, and three kinds of diolefins are easier to autohemagglutination or interpolymerized and then generate dimer, therefore by simple distillation process, each of which cannot be isolated from C5 fraction highly purified product。In prior art, almost all carbon five separating technology is all that raw material first carries out preliminary separation (this process is called pre-separation or pretreatment by industrial custom), and the process such as rectification or extracting rectifying that then again initial gross separation material carried out respectively is to obtain highly purified product。In three kinds of diolefins, cyclopentadiene the most easily occurs hot dimerization reaction generation boiling point higher and the good dicyclopentadiene of heat stability, and isoprene then exists bigger boiling-point difference with pentadiene and dicyclopentadiene。Therefore, in the initial gross separation stage, generally cyclopentadiene is converted into dicyclopentadiene through dimerization reaction, then coordinates distillation process for several times to make three kinds of diolefins realize preliminary separation from C5 fraction。
Traditional C5 fraction separation process scheme is generally all the hot dimerization reaction first carrying out cyclopentadiene in the initial gross separation stage, cyclopentadiene is converted into dicyclopentadiene, separating of isoprene and pentadiene and dicyclopentadiene is realized again through rectification, it is de-light that some is then further added by rectification before hot dimerization, to remove the light components such as carbon four component in raw material and alkynes。Industrial often this will be referred to as front hot dimerization method, the technical scheme that typical visible US Patent No. 3,510,405, Chinese patent ZL96116289.9 and ZL96102485.2 describe。Owing to isoprene and the cyclopentadiene activation energy of hot dimerization reaction altogether and the activation energy of the hot dimerization reaction of cyclopentadiene are closer to, while the hot dimerization of cyclopentadiene, very easily with the common hot dimerization reaction that isoprene and cyclopentadiene occur。Traditional front hot dimerization method flow process due in hot dimerization reaction system isoprene concentrations higher, in addition require to complete the cyclopentadiene conversion to dimer through once hot dimerization reaction, the reaction condition adopted is comparatively violent, therefore has a considerable amount of isoprene and generates with cyclopentadiene codimerization thing。This not only results in a large amount of losses of isoprene and cyclopentadiene, also can affect dicyclopentadiene product purity, because isoprene is close with the boiling point of cyclopentadiene codimerization thing and dicyclopentadiene, and both more difficult separation。Chinese patent ZL200710043976.7 proposes the C5 fraction separation method of a kind of after heat dimerization, it first passes through rectification before C5 fraction material carries out the hot dimerization reaction of cyclopentadiene and is separated from C5 fraction material by isoprene, to avoid the generation of isoprene and cyclopentadiene dimer in hot dimerization reaction process。After heat dimerization processes overcomes the defect of front hot dimerization processes to a certain extent, but its shortcoming is that in material, cyclopentadiene is not yet converted into dicyclopentadiene when separation and Extraction isoprene, through a rectification, isoprene being separated operation easier higher, rectifying column overhead easily carries cyclopentadiene secretly。But what is more important, the tower bottom of rectifying tower of separating isoprene and stripping section are all higher because of temperature residing for cyclopentadiene concentration and material, very easily there is hot dimerization reaction altogether in the isoprene at these positions and cyclopentadiene, therefore still has a considerable amount of isoprene to generate with cyclopentadiene dimer in system。Chinese patent application 200910176552.7 proposes the C5 fraction separation method of a kind of twice separation and Extraction isoprene for the defect of after heat dimerization processes, it arranges a rectifying column before the hot dipolymer reactor of hot dimerization processes flow process before traditional again, at the front and back of hot dimerization reaction separation and Extraction isoprene at twice。The method solves the problem that after heat dimerization processes isoprene rectification knockout tower overhead easily carries cyclopentadiene secretly preferably。But, the common hot dimerization reaction of isoprene and cyclopentadiene is still inevitably there is in the tower reactor of the first isoprene rectification knockout tower and stripping section, it almost follows the after heat dimerization processes track of an overturned cart in this。
As can be seen here, existing C5 fraction separation method all cannot solve in separation process isoprene and cyclopentadiene well and generate this technical problem of dimer because of hot dimerization altogether。
Summary of the invention
The invention provides and a kind of separate C5 fraction the method producing dicyclopentadiene, after C5 fraction is separated, obtain enrichment isoprene and two kinds of initial gross separation materials of pentadiene and dicyclopentadiene purified product。Separation process has been done further improvement by the present invention, solved the technical problem that when being not only against after heat dimerization processes separating isoprene that rectifying tower ejects material and easily carries the defect of cyclopentadiene secretly, and substantially avoided the generation of isoprene and cyclopentadiene dimer in separation process。
The following is the technical scheme that this invention address that above-mentioned technical problem:
A kind of separate C5 fraction the method producing dicyclopentadiene, comprise the following steps:
1) raw material C5 fraction carries out rectification with the light composition impurity of separation removal through rectifying column, and it is 60～90 DEG C that bottom temperature controls, and it is 40～50 DEG C that tower top temperature controls, and operation Stress control is 0.10～0.40MPaG, and control of reflux ratio is 20～40。Tower top discharges light composition impurity, and tower reactor obtains C5 fraction material；
2) by step 1) the preheated dimerization reaction of C5 fraction material that obtains of tower reactor is so that part cyclopentadiene is converted into dicyclopentadiene, it is 40～60 DEG C that reaction temperature controls, it is 0.40～0.80MPaG that reaction pressure controls, and it is 240～600min that the reaction time of material controls；
3) through step 2) preheating dimerization reaction after C5 fraction material carry out rectification with separation and Extraction part isoprene through rectifying column, it is 60～80 DEG C that bottom temperature controls, it is 35～50 DEG C that tower top temperature controls, and operation Stress control is 0.10～0.50MPaG, and control of reflux ratio is 2～10。Tower top must be enriched with the material of isoprene, and tower reactor obtains remaining C5 fraction material；
4) by step 3) the C5 fraction material that obtains of tower reactor through the hot dimerization reaction of second time so that remaining cyclopentadiene is converted into dicyclopentadiene, it is 100～150 DEG C that reaction temperature controls, it is 0.80～1.20MPaG that reaction pressure controls, and it is 60～120min that the reaction time of material controls；
5) through step 4) second time hot dimerization reaction after C5 fraction material carry out rectification with the remaining isoprene of separation and Extraction through rectifying column, it is 70～100 DEG C that bottom temperature controls, it is 50～80 DEG C that tower top temperature controls, operation Stress control is 0.20～0.40MPaG, and control of reflux ratio is 10～20。Tower top must be enriched with the material of isoprene, and tower reactor must be enriched with the material of dicyclopentadiene and pentadiene；
6) by step 5) material that obtains of tower reactor carries out rectification to separate dicyclopentadiene and pentadiene through rectifying column, it is 100～120 DEG C that bottom temperature controls, it is 35～50 DEG C that tower top temperature controls, and operation Stress control is 0.010～0.040MPaG, and control of reflux ratio is 2～10。Tower top must be enriched with the material of pentadiene, and tower reactor must be enriched with the material of dicyclopentadiene；
7) by step 6) material that obtains of tower reactor carries out the refining of dicyclopentadiene through rectifying column, it is 100～130 DEG C that bottom temperature controls, it is 70～90 DEG C that tower top temperature controls, and operation Stress control is-0.030～-0.005MPaG, and control of reflux ratio is 10～30。Tower reactor side line must refine dicyclopentadiene product, and tower top discharges light composition impurity, and tower reactor discharges heavy constituent impurity。
Above-mentioned steps 1) described in bottom temperature preferably control to be 75～85 DEG C；Tower top temperature preferably controls to be 42～48 DEG C；Operation pressure preferably controls to be 0.25～0.35MPaG；Reflux ratio preferably controls to be 25～35。
Above-mentioned steps 2) described in reaction temperature preferably control to be 45～55 DEG C；Reaction pressure preferably controls to be 0.50～0.70MPaG；The reaction time of material preferably controls to be 400～500min。
Above-mentioned steps 3) described in bottom temperature preferably control to be 65～75 DEG C；Tower top temperature preferably controls to be 40～47 DEG C；Operation pressure preferably controls to be 0.25～0.35MPaG；Reflux ratio preferably controls to be 3～8。
On be set forth in step 4) described in reaction temperature preferably control to be 120～140 DEG C；Reaction pressure preferably controls to be 0.90～1.10MPaG；The reaction time of material preferably controls to be 70～90min。
Above-mentioned steps 5) described in bottom temperature preferably control to be 80～90 DEG C；Tower top temperature preferably controls to be 55～70 DEG C；Operation pressure preferably controls to be 0.25～0.30MPaG；Reflux ratio preferably controls to be 12～18。
Above-mentioned steps 6) described in bottom temperature preferably control to be 105～115 DEG C；Tower top temperature preferably controls to be 40～50 DEG C；Operation pressure preferably controls to be 0.025～0.035MPaG；Reflux ratio preferably controls to be 5～8。
Above-mentioned steps 7) described in bottom temperature preferably control to be 105～120 DEG C；Tower top temperature preferably controls to be 75～85 DEG C；Operation pressure preferably controls as-0.020～-0.010MPaG；Reflux ratio preferably controls to be 15～25。
The essence of the present invention is to divide two sections to carry out the hot dimerization reaction of cyclopentadiene on the basis of twice separation and Extraction isoprene technique。First and second sections of hot dimerization reactions are respectively at the front and back of first time separation and Extraction isoprene。Inventor is by experiment it was found that carry out, by this flow process, the defect that the separation energy of C5 fraction overcomes prior art to exist well。
By Kinetic analysis, isoprene and cyclopentadiene concentration are the key factors affecting its hot dimerization reaction speed, isoprene is directly proportional to isoprene, cyclopentadiene concentration product to the reaction rate of cyclopentadiene hot dimerization reaction altogether, and the concentration no matter reducing isoprene or cyclopentadiene all can suppress the reaction rate of they hot dimerization。Prior art after heat dimerization processes or twice separation and Extraction isoprene technique are try to come the generation of inhibition of isoprenyl and cyclopentadiene hot dimerization reaction altogether by reducing isoprene concentrations, but they ignore the separation and Extraction carrying out isoprene when not reducing cyclopentadiene concentration jointly, at the temperature of tower reactor or stripping section, isoprene and cyclopentadiene hot dimerization reaction altogether is easy to occur, in addition material time of staying in rectifying column is often difficult to uniformity, part isoprene is because of the time of staying long chance more increased with cyclopentadiene generation dimerization。The strategy that the present invention takes is to allow the C5 fraction raw material after removing light composition impurity first once preheat dimerization, make significant component of cyclopentadiene complete dimerization, but process regulation cannot met isoprene and cyclopentadiene generation hot dimerization reaction altogether。Because isoprene and cyclopentadiene hot dimerization reaction altogether has of a relatively high activation energy, as long as temperature and the time of staying control suitably, in addition hot dimerization reaction generally adopts tubular reactor, and the material uniformity in the reaction zone time of staying can be guaranteed, and above-mentioned target is easily to realize。After preheated dimerization, cyclopentadiene concentration substantially reduces, and when this makes first time separation and Extraction isoprene, isoprene and cyclopentadiene hot dimerization reaction altogether is effectively inhibited。The hot dimerization reaction of second time carries out at a relatively high temperature, and certain reaction condition is still controlled in suitable scope, to ensure dicyclopentadiene selectivity high as far as possible。Test result indicate that, material is after these three steps, and the conversion ratio of cyclopentadiene and the selectivity of dicyclopentadiene are generally all up more than 95%。Cyclopentadiene amount remaining in system during second time separation and Extraction isoprene is considerably less, and isoprene and cyclopentadiene hot dimerization reaction altogether will not occur substantially。
Technical scheme provided by the invention substantially belongs to the initial gross separation stage that C5 fraction separates, or can be described as the pre-separation of C5 fraction。Plus removing light composition impurity interior, raw material C5 fraction obtains enrichment isoprene and two kinds of initial gross separation materials of pentadiene and dicyclopentadiene purified product after the process of seven steps, and the initial gross separation material of enrichment isoprene or pentadiene can adopt known method to carry out follow-up refinement treatment to obtain highly purified product respectively again。
Compared with prior art, no matter the present invention progressive being in that significantly is all effectively suppressed at the separation and Extraction process isoprene of hot dimerization or isoprene and the common hot dimerization reaction of cyclopentadiene, so that the yield of isoprene and dicyclopentadiene is all improved significantly。It another advantage is that the separation of three kinds of diolefins is more thorough, enrichment isoprene or the initial gross separation material of pentadiene and dicyclopentadiene refining before material in carry the amount of other diolefin secretly and be controlled in very low degree, this alleviates the burden of follow-up refinement treatment on the one hand, is also easier to obtain highly purified product simultaneously。
Accompanying drawing 1 is the process flow diagram of the present invention。
Raw material C5 fraction W1 carries out rectification with the light composition impurity of separation removal through rectifying column 1 (theoretical cam curve is 85), and tower top discharges light composition impurity W3, and tower reactor obtains C5 fraction material W2；W2 enters a tubular reactor 2 and carries out preheating dimerization reaction so that part cyclopentadiene is converted into dicyclopentadiene；W4 carries out rectification with separation and Extraction part isoprene through rectifying column 3 (theoretical cam curve is 54), and tower top must be enriched with the material W6 of isoprene, and tower reactor obtains remaining C5 fraction material W5；W5 enters a tubular reactor 4 and carries out the hot dimerization reaction of second time so that remaining cyclopentadiene is converted into dicyclopentadiene。C5 fraction material W7 after the hot dimerization reaction of second time carries out rectification with the remaining isoprene of separation and Extraction through rectifying column 5 (theoretical cam curve is 80), tower top must be enriched with the material W8 of isoprene, W8 and W6 can send follow-up isoprene refining step after merging, and tower reactor must be enriched with the material W9 of dicyclopentadiene and pentadiene。
W9 carries out rectification to separate dicyclopentadiene and pentadiene through rectifying column 6 (theoretical cam curve is 50), tower top must be enriched with the material W11 of pentadiene, W11 can send follow-up pentadiene refining step, or directly as coarse piperyene product, tower reactor must be enriched with the material W10 of dicyclopentadiene。W10 enters rectifying column 7 (theoretical cam curve is 75) and carries out the refining of dicyclopentadiene, and tower reactor the 2nd piece of column plate place side line from lower to upper must refine dicyclopentadiene product W12, and tower top discharges light composition impurity W13, and tower reactor regularly discharges heavy constituent impurity W14。
Following by specific embodiment, the invention will be further described, in an embodiment, the definition of cyclopentadiene conversion ratio, dicyclopentadiene selectivity (selectivity I), isoprene and dicyclopentadiene dimer selectivity (selectivity II), dicyclopentadiene purified product yield is respectively as follows:
Wherein:
Flow × cyclopentadiene the mole percent of unit interval cyclopentadiene mole of feed amount=W2；
The flow of unit interval dicyclopentadiene mole load=W10 × dicyclopentadiene mole percent；
Flow × the isoprene of unit interval isoprene and cyclopentadiene dimer mole load=W10 and cyclopentadiene dimer mole percent；
Flow × dicyclopentadiene the mole percent of unit interval dicyclopentadiene molar product load=W12。
Accompanying drawing explanation
Fig. 1 separates C5 fraction and produces the process flow diagram of double; two method changing pentadiene。
Detailed description of the invention
[embodiment 1～10]
The technological process of embodiment 1～10 is shown in that accompanying drawing 1, raw material C5 fraction W1 are that petroleum cracking ethylene by-product obtains, and it mainly comprises in Table 1。
The process condition of each embodiment rectifying column 1,3,5,6 and 7, the process condition of preheating dipolymer reactor and dipolymer reactor 2,4 is respectively in Table 2,3,4 and 5。Adopting gas chromatography to analyze the composition of material W6, W8, W10, W11 and W12 respectively, in each material, the content of enriched composition is in Table 6。In conjunction with the yield of the flow rate calculation cyclopentadiene conversion ratio of each material, dicyclopentadiene selectivity (selectivity I), isoprene and cyclopentadiene dimer selectivity (selectivity II), dicyclopentadiene purified product, result is in Table 7。
Table 1.
Table 2.
Table 3.
Table 4.
Table 5.
Table 6.
Table 7.
Claims (8)
1. separate C5 fraction the method producing dicyclopentadiene, comprise the following steps:
1) raw material C5 fraction carries out rectification with the light composition impurity of separation removal through rectifying column, it is 60～90 DEG C that bottom temperature controls, it is 40～50 DEG C that tower top temperature controls, operation Stress control is 0.10～0.40MPaG, control of reflux ratio is 20～40, tower top discharges light composition impurity, and tower reactor obtains C5 fraction material；
2) by step 1) the preheated dimerization reaction of C5 fraction material that obtains of tower reactor is so that part cyclopentadiene is converted into dicyclopentadiene, it is 40～60 DEG C that reaction temperature controls, it is 0.40～0.80MPaG that reaction pressure controls, and it is 240～600min that the reaction time of material controls；
3) through step 2) preheating dimerization reaction after C5 fraction material carry out rectification with separation and Extraction part isoprene through rectifying column, it is 60～80 DEG C that bottom temperature controls, it is 35～50 DEG C that tower top temperature controls, operation Stress control is 0.10～0.50MPaG, control of reflux ratio is 2～10, tower top must be enriched with the material of isoprene, and tower reactor obtains remaining C5 fraction material；
4) by step 3) the C5 fraction material that obtains of tower reactor through the hot dimerization reaction of second time so that remaining cyclopentadiene is converted into dicyclopentadiene, it is 100～150 DEG C that reaction temperature controls, it is 0.80～1.20MPaG that reaction pressure controls, and it is 60～120min that the reaction time of material controls；
5) through step 4) second time hot dimerization reaction after C5 fraction material carry out rectification with the remaining isoprene of separation and Extraction through rectifying column, it is 70～100 DEG C that bottom temperature controls, it is 50～80 DEG C that tower top temperature controls, operation Stress control is 0.20～0.40MPaG, control of reflux ratio is 10～20, tower top must be enriched with the material of isoprene, and tower reactor must be enriched with the material of dicyclopentadiene and pentadiene；
6) by step 5) material that obtains of tower reactor carries out rectification to separate dicyclopentadiene and pentadiene through rectifying column, it is 100～120 DEG C that bottom temperature controls, it is 35～50 DEG C that tower top temperature controls, operation Stress control is 0.010～0.040MPaG, control of reflux ratio is 2～10, tower top must be enriched with the material of pentadiene, and tower reactor must be enriched with the material of dicyclopentadiene；
7) by step 6) material that obtains of tower reactor carries out the refining of dicyclopentadiene through rectifying column, it is 100～130 DEG C that bottom temperature controls, it is 70～90 DEG C that tower top temperature controls, operation Stress control is-0.030～-0.005MPaG, control of reflux ratio is 10～30, tower reactor side line must refine dicyclopentadiene product, and tower top discharges light composition impurity, and tower reactor discharges heavy constituent impurity。
2. separation C5 fraction according to claim 1 the method for producing dicyclopentadiene, it is characterized in that step 1) described in bottom temperature control be 75～85 DEG C, it is 42～48 DEG C that tower top temperature controls, and operation Stress control is 0.25～0.35MPaG, and control of reflux ratio is 25～35。
3. separation C5 fraction according to claim 1 the method for producing dicyclopentadiene, it is characterized in that step 2) described in reaction temperature control be 45～55 DEG C, it is 0.50～0.70MPaG that reaction pressure controls, and it is 400～500min that the reaction time of material controls。
4. separation C5 fraction according to claim 1 the method for producing dicyclopentadiene, it is characterized in that step 3) described in bottom temperature control be 65～75 DEG C, it is 40～47 DEG C that tower top temperature controls, and operation Stress control is 0.25～0.35MPaG, and control of reflux ratio is 3～8。
5. separation C5 fraction according to claim 1 the method for producing dicyclopentadiene, it is characterized in that step 4) described in reaction temperature control be 120～140 DEG C, it is 0.90～1.10MPaG that reaction pressure controls, and it is 70～90min that the reaction time of material controls。
6. separation C5 fraction according to claim 1 the method for producing dicyclopentadiene, it is characterized in that step 5) described in bottom temperature control be 80～90 DEG C, it is 55～70 DEG C that tower top temperature controls, and operation Stress control is 0.25～0.30MPaG, and control of reflux ratio is 12～18。
7. separation C5 fraction according to claim 1 the method for producing dicyclopentadiene, it is characterized in that step 6) described in bottom temperature control be 105～115 DEG C, it is 40～50 DEG C that tower top temperature controls, and operation Stress control is 0.025～0.035MPaG, and control of reflux ratio is 5～8。
8. separation C5 fraction according to claim 1 the method for producing dicyclopentadiene, it is characterized in that step 7) described in bottom temperature control be 105～120 DEG C, it is 75～85 DEG C that tower top temperature controls, operation Stress control is-0.020～-0.010MPaG, and control of reflux ratio is 15～25。
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| CN101092319A (en) * | 2006-06-23 | 2007-12-26 | 天津天大天海化工新技术有限公司 | Method for separating cyclopentadiene |
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| CN101665400A (en) * | 2009-09-22 | 2010-03-10 | 宁波金海德旗化工有限公司 | Pre-separation method of C5 diene for distilling off methyl butane for two times |
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| CA854169A (en) * | 1970-10-20 | Monsanto Company | Treatment of hydrocarbon streams | |
| CN1160035A (en) * | 1996-03-20 | 1997-09-24 | 中国石油化工总公司 | Method for separation of petroleum cracking C5 fraction by liquid phase feeding extraction rectification |
| CN101092319A (en) * | 2006-06-23 | 2007-12-26 | 天津天大天海化工新技术有限公司 | Method for separating cyclopentadiene |
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