CN102951987A - Method for separation of C5 fraction and preparation of dicyclopentadiene - Google Patents
Method for separation of C5 fraction and preparation of dicyclopentadiene Download PDFInfo
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Abstract
The invention relates to a method for separation of C5 fraction and preparation of dicyclopentadiene. The method includes: rectifying raw material C5 fraction to remove light component impurities; subjecting the obtained material to a pre-thermal dimerization reaction to make part of cyclopentadiene converted into dicyclopentadiene; rectifying the material that undergoes the pre-thermal dimerization reaction to separate and extract part of isoprene, thus obtaining an isoprene concentrated material at a tower top; subjecting the material obtained from a tower bottom in the last step to a second thermal dimerization reaction so as to make the remaining cyclopentadiene converted into dicyclopentadiene; rectifying the material to separate and extract the remaining isoprene, thus obtaining an isoprene concentrated material at the tower top and a dicyclopentadiene and m-pentadiene concentrated material at the tower bottom; rectifying the material obtained in the tower bottom in the last step to separate dicyclopentadiene and m-pentadiene, thus obtaining an m-pentadiene concentrated material at the tower top and a dicyclopentadiene concentrated material at the tower bottom; and conducting rectification and purification on the material obtained from the tower bottom in the last step so as to obtain a dicyclopentadiene product. The invention has the advantage that in the separation process the co-thermal dimerization reaction of isoprene and cyclopentadiene can be effectively inhibited, so that the loss of isoprene and cyclopentadiene is reduced.
Description
Technical field
The present invention relates to the method for separating carbon 5 fraction, the C5 fraction that is particularly related to by petroleum cracking ethylene by-product processed obtains isoprene and m-pentadiene initial gross separation material by processes such as hot dimerization and rectifying separation, and obtains simultaneously the method for dicyclopentadiene purified product.
Background technology
Can go out a kind of C5 fraction by by-product in the petroleum cracking process of producing ethylene, C5 fraction occupies higher proportion in all cracking of ethylene by-product materials.Contain cyclopentadiene, isoprene and m-pentadiene that total amount is 40～60wt% in the C5 fraction, these three kinds of diolefin chemical property are active, can react with gas chromatography, all have been widely used at resin, rubber, medicine or agricultural chemicals and other field of fine chemical.At present, separate produce cyclopentadiene, isoprene and m-pentadiene be C5 fraction main also be the method for utilizing of tool economic worth.The C5 fraction complicated component, it is close to be permitted multi-component boiling point, or form easily azeotrope, and therefore three kinds of easier autohemagglutinations of diolefin or poly-and then generate dipolymer mutually can't each isolate highly purified product with them by simple rectifying in C5 fraction.In the prior art, almost all carbon five separating technologies all are first raw material to be carried out preliminary separation (industrial custom is called pre-separation or pre-treatment with this process), and then the initial gross separation material is carried out respectively the processes such as rectifying or extracting rectifying to obtain highly purified product.In three kinds of diolefins, the hot dimerization reaction of the easiest generation of cyclopentadiene generates the higher and good dicyclopentadiene of thermostability of boiling point, and then there is larger boiling-point difference in isoprene with m-pentadiene and dicyclopentadiene.Therefore in the initial gross separation stage, usually cyclopentadiene is converted into dicyclopentadiene through dimerization reaction, cooperating for several times, rectifying makes three kinds of diolefins realize preliminary separation from C5 fraction again.
Traditional C5 fraction separation process scheme all is the hot dimerization reaction that carries out first cyclopentadiene usually in the initial gross separation stage, cyclopentadiene is converted into dicyclopentadiene, realize separating of isoprene and m-pentadiene and dicyclopentadiene by rectifying again, some then increases rectifying again before hot dimerization takes off gently, to remove the light constituents such as carbon four components in the raw material and alkynes.Industrial front hot dimerization method, the technical scheme that typical visible US Patent No. 3,510,405, Chinese patent ZL96116289.9 and ZL96102485.2 describe of often this being called.Because the activation energy of the common hot dimerization reaction of isoprene and cyclopentadiene and the activation energy of the hot dimerization reaction of cyclopentadiene are comparatively approaching, in the time of the hot dimerization of cyclopentadiene, the very easy common hot dimerization reaction that isoprene and cyclopentadiene occur of following.Traditional front hot dimerization method flow process since in the hot dimerization reaction system isoprene concentration higher, require to finish cyclopentadiene to the conversion of dipolymer through hot dimerization reaction once in addition, the reaction conditions that adopts is comparatively violent, therefore has a considerable amount of isoprene and cyclopentadiene codimerization thing and generates.A large amount of losses that this not only causes isoprene and cyclopentadiene also can affect the dicyclopentadiene product purity, and very near because of the boiling point of isoprene and cyclopentadiene codimerization thing and dicyclopentadiene, both are difficult the separation.Chinese patent ZL200710043976.7 has proposed a kind of C5 fraction separation method of after heat dimerization, it is separated isoprene by rectifying first before the C5 fraction material carries out the hot dimerization reaction of cyclopentadiene from the C5 fraction material, to avoid the generation of isoprene and cyclopentadiene dipolymer in the hot dimerization reaction process.The defective of hot dimerization processes before the after heat dimerization processes has overcome to a certain extent, but its shortcoming be when the separation and Extraction isoprene in the material cyclopentadiene not yet be converted into dicyclopentadiene, it is higher through a rectifying isoprene to be separated operation easier, and rectifying tower cat head overhead product is carried cyclopentadiene easily secretly.Yet what is more important, the tower bottom of rectifying tower of separating isoprene and stripping section are all higher because of cyclopentadiene concentration and material temperature of living in, altogether hot dimerization reaction very easily occurs in the isoprene at these positions and cyclopentadiene, so still has a considerable amount of isoprene and cyclopentadiene dipolymer to generate in the system.Chinese patent application 200910176552.7 has proposed a kind of C5 fraction separation method of twice separation and Extraction isoprene for the defective of after heat dimerization processes, it arranges a rectifying tower again before the hot dipolymer reactor of traditional front hot dimerization processes flow process, the separation and Extraction isoprene at twice in the front and back of hot dimerization reaction.The method has solved the problem that after heat dimerization processes isoprene rectifying separation column overhead overhead product is easily carried cyclopentadiene secretly preferably.But at the common hot dimerization reaction that isoprene and cyclopentadiene still occur inevitably for tower reactor and the stripping section of the first isoprene rectifying separation tower, it almost follows the after heat dimerization processes track of an overturned cart in this.
This shows that existing C5 fraction separation method all can't solve well in the sepn process isoprene and cyclopentadiene and generate this technical problem of dipolymer because of hot dimerization altogether.
Summary of the invention
The invention provides a kind of separating carbon 5 fraction and produce the method for dicyclopentadiene, C5 fraction obtains enrichment isoprene and two kinds of initial gross separation materials of m-pentadiene and dicyclopentadiene purified product after separating.The present invention has done further improvement to separation process, the technical problem that solves is that rectifying tower ejects the defective that material is easily carried cyclopentadiene secretly when not only overcoming after heat dimerization processes separating isoprene, and substantially avoids the generation of isoprene and cyclopentadiene dipolymer in the sepn process.
Below be the technical scheme that the present invention solves the problems of the technologies described above:
A kind of separating carbon 5 fraction is also produced the method for dicyclopentadiene, may further comprise the steps:
1) the raw material C5 fraction is carried out rectifying with separation removal light constituent impurity through rectifying tower, and the tower reactor temperature is controlled to be 60～90 ℃, and tower top temperature is controlled to be 40～50 ℃, and working pressure is controlled to be 0.10～0.40MPaG, and control of reflux ratio is 20～40.Cat head is discharged light constituent impurity, and tower reactor gets the C5 fraction material;
2) by step 1) the C5 fraction material that obtains of tower reactor through the preheating dimerization reaction so that the part cyclopentadiene is converted into dicyclopentadiene, temperature of reaction is controlled to be 40～60 ℃, reaction pressure is controlled to be 0.40～0.80MPaG, and the reaction time of material is controlled to be 240～600min;
3) through step 2) C5 fraction material behind the preheating dimerization reaction carries out rectifying with separation and Extraction part isoprene through rectifying tower, the tower reactor temperature is controlled to be 60～80 ℃, tower top temperature is controlled to be 35～50 ℃, and working pressure is controlled to be 0.10～0.50MPaG, and control of reflux ratio is 2～10.Cat head gets the material of enrichment isoprene, and tower reactor gets remaining C5 fraction material;
4) by step 3) the C5 fraction material that obtains of tower reactor through hot dimerization reaction for the second time so that remaining cyclopentadiene is converted into dicyclopentadiene, temperature of reaction is controlled to be 100～150 ℃, reaction pressure is controlled to be 0.80～1.20MPaG, and the reaction time of material is controlled to be 60～120min;
5) through step 4) for the second time the C5 fraction material behind the hot dimerization reaction carry out rectifying with the remaining isoprene of separation and Extraction through rectifying tower, the tower reactor temperature is controlled to be 70～100 ℃, tower top temperature is controlled to be 50～80 ℃, working pressure is controlled to be 0.20～0.40MPaG, and control of reflux ratio is 10～20.Cat head gets the material of enrichment isoprene, and tower reactor gets the material of enrichment dicyclopentadiene and m-pentadiene;
6) by step 5) material that obtains of tower reactor carries out rectifying to separate dicyclopentadiene and m-pentadiene through rectifying tower, the tower reactor temperature is controlled to be 100～120 ℃, tower top temperature is controlled to be 35～50 ℃, and working pressure is controlled to be 0.010～0.040MPaG, and control of reflux ratio is 2～10.Cat head gets the material of enrichment m-pentadiene, and tower reactor gets the material of enrichment dicyclopentadiene;
7) by step 6) material that obtains of tower reactor carries out the refining of dicyclopentadiene through rectifying tower, and the tower reactor temperature is controlled to be 100～130 ℃, and tower top temperature is controlled to be 70～90 ℃, and working pressure is controlled to be-0.030～-0.005MPaG, control of reflux ratio is 10～30.The tower reactor side line must be made with extra care the dicyclopentadiene product, and cat head is discharged light constituent impurity, and tower reactor is discharged restructuring minute impurity.
Above-mentioned steps 1) described tower reactor temperature preferably is controlled to be 75～85 ℃; Tower top temperature preferably is controlled to be 42～48 ℃; Working pressure preferably is controlled to be 0.25～0.35MPaG; Reflux ratio preferably is controlled to be 25～35.
Above-mentioned steps 2) described temperature of reaction preferably is controlled to be 45～55 ℃; Reaction pressure preferably is controlled to be 0.50～0.70MPaG; The reaction time of material preferably is controlled to be 400～500min.
Above-mentioned steps 3) described tower reactor temperature preferably is controlled to be 65～75 ℃; Tower top temperature preferably is controlled to be 40～47 ℃; Working pressure preferably is controlled to be 0.25～0.35MPaG; Reflux ratio preferably is controlled to be 3～8.
On be set forth in step 4) described temperature of reaction preferably is controlled to be 120～140 ℃; Reaction pressure preferably is controlled to be 0.90～1.10MPaG; The reaction time of material preferably is controlled to be 70～90min.
Above-mentioned steps 5) described tower reactor temperature preferably is controlled to be 80～90 ℃; Tower top temperature preferably is controlled to be 55～70 ℃; Working pressure preferably is controlled to be 0.25～0.30MPaG; Reflux ratio preferably is controlled to be 12～18.
Above-mentioned steps 6) described tower reactor temperature preferably is controlled to be 105～115 ℃; Tower top temperature preferably is controlled to be 40～50 ℃; Working pressure preferably is controlled to be 0.025～0.035MPaG; Reflux ratio preferably is controlled to be 5～8.
Above-mentioned steps 7) described tower reactor temperature preferably is controlled to be 105～120 ℃; Tower top temperature preferably is controlled to be 75～85 ℃; Working pressure preferably is controlled to be-0.020～-0.010MPaG; Reflux ratio preferably is controlled to be 15～25.
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 hot dimerization reactions are in respectively for the first time front and back of separation and Extraction isoprene.The contriver found that by experiment the separation energy of carrying out C5 fraction by this flow process overcomes the defective that prior art exists well.
Press Kinetic analysis, isoprene and cyclopentadiene concentration are the important factors that affects its hot dimerization reaction speed, isoprene is directly proportional with isoprene, cyclopentadiene concentration product with the speed of reaction that cyclopentadiene is total to hot dimerization reaction, and the concentration that no matter reduces isoprene or cyclopentadiene all can suppress the speed of reaction of their hot dimerization.Prior art after heat dimerization processes or twice separation and Extraction isoprene technique all are to attempt to come the altogether generation of hot dimerization reaction of inhibition of isoprenyl and cyclopentadiene by reducing isoprene concentration, yet they have ignored the separation and Extraction of carrying out isoprene in the situation that does not reduce cyclopentadiene concentration jointly, isoprene and cyclopentadiene are total to hot dimerization reaction and are easy to generation under the temperature of tower reactor or stripping section, material residence time in rectifying tower often is difficult to uniformity in addition, and the part isoprene more increases chance with cyclopentadiene generation dimerization because of overstand.The strategy that the present invention takes is to allow the C5 fraction raw material that removes behind the light constituent impurity at first carry out the preheating dimerization one time, make the cyclopentadiene of quite a few finish dimerization, but process regulation can't satisfied altogether hot dimerization reaction of isoprene and cyclopentadiene generation.Because isoprene and cyclopentadiene altogether hot dimerization reaction have relatively high activation energy, as long as temperature and residence time control are suitably, hot dimerization reaction adopts tubular reactor usually in addition, and material can be guaranteed in the homogeneity of the reaction zone residence time, and above-mentioned target is to realize easily.Cyclopentadiene concentration obviously reduces after the preheating dimerization, this so that for the first time during the separation and Extraction isoprene isoprene effectively be inhibited with the common hot dimerization reaction of cyclopentadiene.Hot dimerization reaction carries out under relatively high temperature for the second time, and reaction conditions still is controlled in suitable scope certainly, to guarantee high as far as possible dicyclopentadiene selectivity.Experimental result shows that material is after these three steps, and the transformation efficiency of cyclopentadiene and the selectivity of dicyclopentadiene generally all can reach more than 95%.For the second time during the separation and Extraction isoprene in the system remaining cyclopentadiene amount considerably less, the common hot dimerization reaction of isoprene and cyclopentadiene can not occur basically.
Technical scheme provided by the invention belongs to the initial gross separation stage that C5 fraction separates in essence, or can be described as the pre-separation of C5 fraction.Add and remove light constituent impurity interior, the raw material C5 fraction obtains two kinds of initial gross separation materials and the dicyclopentadiene purified product of enrichment isoprene and m-pentadiene after the processing of seven steps, the initial gross separation material of enrichment isoprene or m-pentadiene can adopt respectively known method to carry out follow-up refinement treatment again and obtain highly purified product.
Compared with prior art, no matter the present invention is significant progressive is common hot dimerization reaction at the separation and Extraction process isoprene of hot dimerization or isoprene and cyclopentadiene all by establishment, thereby the yield of isoprene and dicyclopentadiene all is improved significantly.The separation that its another advantage is three kinds of diolefins is more thorough, the amount of carrying other diolefin in the material before the initial gross separation material of enrichment isoprene or m-pentadiene and dicyclopentadiene are refining secretly is controlled in very low degree, this has alleviated the burden of follow-up refinement treatment on the one hand, obtains highly purified product simultaneously also easilier.
Accompanying drawing is process flow diagram of the present invention.
Raw material C5 fraction W1 carries out rectifying with separation removal light constituent impurity through rectifying tower 1 (theoretical plate number is 85), and cat head is discharged light constituent impurity W3, and tower reactor gets C5 fraction material W2; W2 enters a tubular reactor 2 and carries out the preheating dimerization reaction so that the part cyclopentadiene is converted into dicyclopentadiene; W4 carries out rectifying with separation and Extraction part isoprene through rectifying tower 3 (theoretical plate number is 54), and cat head gets the material W6 of enrichment isoprene, and tower reactor gets remaining C5 fraction material W5; W5 enters a tubular reactor 4 and carries out the second time hot dimerization reaction so that remaining cyclopentadiene is converted into dicyclopentadiene.C5 fraction material W7 behind the hot dimerization reaction carries out rectifying with the remaining isoprene of separation and Extraction through rectifying tower 5 (theoretical plate number is 80) for the second time, cat head gets the material W8 of enrichment isoprene, W8 and W6 can send follow-up isoprene refining step after merging, and tower reactor gets the material W9 of enrichment dicyclopentadiene and m-pentadiene.
W9 carries out rectifying to separate dicyclopentadiene and m-pentadiene through rectifying tower 6 (theoretical plate number is 50), cat head gets the material W11 of enrichment m-pentadiene, W11 can send follow-up m-pentadiene refining step, or directly as the coarse piperyene product, tower reactor gets the material W10 of enrichment dicyclopentadiene.W10 enters rectifying tower 7 (theoretical plate number is 75) and carries out the refining of dicyclopentadiene, and tower reactor from lower to upper the 2nd column plate place side line must be made with extra care dicyclopentadiene product W12, and cat head is discharged light constituent impurity W13, and tower reactor is regularly discharged restructuring minute impurity W14.
The below will the invention will be further described by specific embodiment, in an embodiment, the definition of cyclopentadiene transformation efficiency, dicyclopentadiene selectivity (selectivity I), isoprene and dicyclopentadiene dipolymer selectivity (selectivity II), dicyclopentadiene purified product yield is respectively:
Wherein:
The flow of unit time cyclopentadiene mole of feed amount=W2 * cyclopentadiene molecular fraction;
The flow of unit time dicyclopentadiene mole load=W10 * dicyclopentadiene molecular fraction;
Flow * isoprene of unit time isoprene and cyclopentadiene dipolymer mole load=W10 and cyclopentadiene dipolymer molecular fraction;
The flow of unit time dicyclopentadiene molar product load=W12 * dicyclopentadiene molecular fraction.
Embodiment
[embodiment 1～10]
Accompanying drawing is seen in the technical process of embodiment 1～10, and raw material C5 fraction W1 is that petroleum cracking ethylene by-product processed obtains, and its chief component sees Table 1.
Each embodiment rectifying tower 1,3,5,6 and 7 process conditions, preheating dipolymer reactor and dipolymer reactor 2,4 process conditions see Table respectively 2,3,4 and 5.Adopt vapor-phase chromatography to analyze respectively the composition of material W6, W8, W10, W11 and W12, the content of enriched composition sees Table 6 in each material.In conjunction with flow rate calculation cyclopentadiene transformation efficiency, dicyclopentadiene selectivity (selectivity I), isoprene and the cyclopentadiene dipolymer selectivity (selectivity II) of each material, the yield of dicyclopentadiene purified product, the results are shown in Table 7 again.
Table 1.
Table 2.
Table 3.
Table 4.
Table 5.
Table 6.
Table 7.
Claims (8)
1. a separating carbon 5 fraction and produce the method for dicyclopentadiene may further comprise the steps:
1) the raw material C5 fraction is carried out rectifying with separation removal light constituent impurity through rectifying tower, the tower reactor temperature is controlled to be 60～90 ℃, tower top temperature is controlled to be 40～50 ℃, working pressure is controlled to be 0.10～0.40MPaG, control of reflux ratio is 20～40, cat head is discharged light constituent impurity, and tower reactor gets the C5 fraction material;
2) by step 1) the C5 fraction material that obtains of tower reactor through the preheating dimerization reaction so that the part cyclopentadiene is converted into dicyclopentadiene, temperature of reaction is controlled to be 40～60 ℃, reaction pressure is controlled to be 0.40～0.80MPaG, and the reaction time of material is controlled to be 240～600min;
3) through step 2) C5 fraction material behind the preheating dimerization reaction carries out rectifying with separation and Extraction part isoprene through rectifying tower, the tower reactor temperature is controlled to be 60～80 ℃, tower top temperature is controlled to be 35～50 ℃, working pressure is controlled to be 0.10～0.50MPaG, control of reflux ratio is 2～10, cat head gets the material of enrichment isoprene, and tower reactor gets remaining C5 fraction material;
4) by step 3) the C5 fraction material that obtains of tower reactor through hot dimerization reaction for the second time so that remaining cyclopentadiene is converted into dicyclopentadiene, temperature of reaction is controlled to be 100～150 ℃, reaction pressure is controlled to be 0.80～1.20MPaG, and the reaction time of material is controlled to be 60～120min;
5) through step 4) for the second time the C5 fraction material behind the hot dimerization reaction carry out rectifying with the remaining isoprene of separation and Extraction through rectifying tower, the tower reactor temperature is controlled to be 70～100 ℃, tower top temperature is controlled to be 50～80 ℃, working pressure is controlled to be 0.20～0.40MPaG, control of reflux ratio is 10～20, cat head gets the material of enrichment isoprene, and tower reactor gets the material of enrichment dicyclopentadiene and m-pentadiene;
6) by step 5) material that obtains of tower reactor carries out rectifying to separate dicyclopentadiene and m-pentadiene through rectifying tower, the tower reactor temperature is controlled to be 100～120 ℃, tower top temperature is controlled to be 35～50 ℃, working pressure is controlled to be 0.010～0.040MPaG, control of reflux ratio is 2～10, cat head gets the material of enrichment m-pentadiene, and tower reactor gets the material of enrichment dicyclopentadiene;
7) by step 6) material that obtains of tower reactor carries out the refining of dicyclopentadiene through rectifying tower, the tower reactor temperature is controlled to be 100～130 ℃, tower top temperature is controlled to be 70～90 ℃, working pressure is controlled to be-0.030～-0.005MPaG, control of reflux ratio is 10～30, the tower reactor side line must be made with extra care the dicyclopentadiene product, and cat head is discharged light constituent impurity, and tower reactor is discharged restructuring minute impurity.
2. separating carbon 5 fraction according to claim 1 and produce the method for dicyclopentadiene, it is characterized in that step 1) described tower reactor temperature is controlled to be 75～85 ℃, tower top temperature is controlled to be 42～48 ℃, and working pressure is controlled to be 0.25～0.35MPaG, and control of reflux ratio is 25～35.
3. separating carbon 5 fraction according to claim 1 and produce the method for dicyclopentadiene, it is characterized in that step 2) described temperature of reaction is controlled to be 45～55 ℃, reaction pressure is controlled to be 0.50～0.70MPaG, and the reaction time of material is controlled to be 400～500min.
4. separating carbon 5 fraction according to claim 1 and produce the method for dicyclopentadiene, it is characterized in that step 3) described tower reactor temperature is controlled to be 65～75 ℃, tower top temperature is controlled to be 40～47 ℃, and working pressure is controlled to be 0.25～0.35MPaG, and control of reflux ratio is 3～8.
5. separating carbon 5 fraction according to claim 1 and produce the method for dicyclopentadiene, it is characterized in that step 4) described temperature of reaction is controlled to be 120～140 ℃, reaction pressure is controlled to be 0.90～1.10MPaG, and the reaction time of material is controlled to be 70～90min.
6. separating carbon 5 fraction according to claim 1 and produce the method for dicyclopentadiene, it is characterized in that step 5) described tower reactor temperature is controlled to be 80～90 ℃, tower top temperature is controlled to be 55～70 ℃, and working pressure is controlled to be 0.25～0.30MPaG, and control of reflux ratio is 12～18.
7. separating carbon 5 fraction according to claim 1 and produce the method for dicyclopentadiene, it is characterized in that step 6) described tower reactor temperature is controlled to be 105～115 ℃, tower top temperature is controlled to be 40～50 ℃, and working pressure is controlled to be 0.025～0.035MPaG, and control of reflux ratio is 5～8.
8. separating carbon 5 fraction according to claim 1 and produce the method for dicyclopentadiene, it is characterized in that step 7) described tower reactor temperature is controlled to be 105～120 ℃, tower top temperature is controlled to be 75～85 ℃, working pressure is controlled to be-0.020～-0.010MPaG, control of reflux ratio is 15～25.
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| CN114276207A (en) * | 2021-12-23 | 2022-04-05 | 茂名鲁华新材料有限公司 | Negative pressure control method for pentadiene tower and carbon six tower |
| CN114276207B (en) * | 2021-12-23 | 2023-09-08 | 广东鲁众华新材料有限公司 | Negative pressure control method for piperylene tower and carbon six tower |
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