CN102399123A - Method for preparing dicyclopentadiene and dimethylcyclopentadiene - Google Patents
Method for preparing dicyclopentadiene and dimethylcyclopentadiene Download PDFInfo
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Abstract
The invention relates to a method for preparing dicyclopentadiene and dimethylcyclopentadiene. The method adopts C9-C19 fractions of byproducts of ethylene cracked from petroleum as raw materials. The method comprises the following processes: 1, the raw materials are subjected to reduced pressure rectification separation in a rectification tower, a concentrated dicyclopentadiene material is obtained from the tower top, and a concentrated dimethylcyclopentadiene material is obtained from the tower bottom; 2, the tower top material obtained in process 1 enters a depolymerization rectification tower for depolymerization rectification, and cyclopentadiene is obtained from the tower top; 3, the tower bottom material obtained in the process 1 enters the depolymerization rectification tower for depolymerization rectification, cyclopentadiene is obtained from the tower top, and methylcyclopentadiene is obtained from the lateral line; 4, cyclopentadiene obtained in process 2 and cyclopentadiene obtained in process 3 undergo a thermal dimerization reaction to obtain dicyclopentadiene; and 5, methylcyclopentadiene obtained in the process 3 undergoes the thermal dimerization reaction to obtain dimethylcyclopentadiene. The method of the invention has the following advantages: dimerization reactions in the depolymerization product rectification separation process are substantially reduced; and high purity methylcyclopentadiene can be directly obtained after the depolymerization product separation, so the refinement and the purification of above depolymerized products are avoided.
Description
Technical field
The present invention relates to the preparation method of NSC 7352 and two methyl cyclopentadienes, particularly prepare the method for NSC 7352 and two methyl cyclopentadienes through processes such as depolymerization, separation and hot dimerization by the C9～C10 cut of petroleum cracking system ethylene by-product.
Background technology
During petroleum cracking system ethene, cracking stock obtains a considerable amount of excess material of taking out, i.e. C9～C10 cut after isolating the light fraction of carbon below eight.Mainly contain the dipolymer of NSC 7352 (DCPD), two methyl cyclopentadiene (DMCPD) and more a spot of cyclopentadiene and methyl cyclopentadiene in this cut, the three adds up to content to be about about 40～65wt%.The depolymerization product cyclopentadiene (CPD) and the methyl cyclopentadiene (MCPD) of these three kinds of dipolymers have purposes widely at chemical industry or field of fine chemical, therefore, separate through depolymerization and to produce CPD and MCPD is the topmost approach that utilizes of present C9～C10 cut.Because CPD and MCPD are prone to autohemagglutination, carry out the preparation of subsequent product as directly not being used, and then must through hot dimerization reaction they be made for the stable state material under the normal temperature, i.e. DCPD and DMCPD again.The existing multiple method release that is used for extracting CPD and MCPD in the prior art from C9～C10 cut, like U.S. Pat 4,522,688, one Chinese patent application 200710115023.7.Although existing method flow process is difference to some extent, its common ground is to be CPD and MCPD with three kinds of dipolymer depolymerization in C9～C10 cut earlier, from depolymerization product, isolates the higher CPD of purity, MCPD through rectifying then.Separating collecting process generally carries out in the depolymerization rectifying tower; The depolymerization rectifying tower is the depolymerization reaction still that a kind of top has the rectifying separation device in essence; The bottom is the rectifying tower of depolymerizing reactor in other words conj.or perhaps, and the depolymerization reaction product carries out rectifying separation with the rectifying tower that gaseous state directly rises to top.The typical visible accompanying drawing 1 of prior art, it has showed U.S. Pat 4,522, the flow process of depolymerization and the CPD that carries out subsequently, MCPD rectifying separation part in 688.C9～C10 cut W1 carries out earlier depolymerization rectifying in depolymerization rectifying tower 1, overhead product material W2 is CPD and MCPD and the boiling point mixture of close material with it, and this mixture carries out rectifying separation through CPD rectifying tower 2 and MCPD rectifying tower 3 subsequently successively.The cat head of CPD rectifying tower 2 obtains CPD finished product W4, and its tower still material W5 obtains MCPD finished product W6 in cat head after 3 rectifying of MCPD rectifying tower.There is obvious defects in existing method, and in the rectifying separation process, along with the raising of CPD and MCPD concentration, the probability that dimerization reaction takes place sharply increases, and particularly MCPD experience flow process is longer, and dimerisation products is more.In order to reduce the loss of material, the way that solves usually is that the dipolymer of CPD rectifying tower and MCPD rectifying tower accumulation generation is returned the depolymerization rectifying tower with the tower still material W7 of MCPD rectifying tower 3.Yet this has caused the one-pass yield reduction; And the circulation repeatedly of material makes the further hot polymerization of dipolymer become polymer; Polymer can't be accomplished depolymerization under the processing condition of depolymerization rectifying tower 1, the most at last as the tower still material W3 discharge system of waste material with depolymerization rectifying tower 1.
In addition, also have C6, the C7 component of some amount in C9～C10 cut usually, like methylene radical cyclopentenes and toluene, generally the former content can reach 0.5～1.0wt.%, and latter's content can reach 3.0～5.0wt.%.The boiling point and the MCPD of these C6, C7 component are more approaching; And in order to reduce the generation of dimerization reaction, rectifying requires with lower reflux ratio operation, and rectifying tower also should not adopt more theoretical plate number; This makes MCPD to realize well separating with C6, C7 component; Existing method is difficult to obtain highly purified MCPD, and therefore the highest usually 95wt.% that is merely of its purity must utilize the boiling-point difference of DMCPD and C6, C7 component to carry out the purification of product again through rectifying after the MCPD dimerization.
Summary of the invention
The invention provides the preparation method of a kind of NSC 7352 and two methyl cyclopentadienes; It is a raw material with the C9～C10 cut of petroleum cracking system ethylene by-product; Obtain DCPD and DMCPD product through processes such as depolymerization, rectifying separation and hot dimerization; Technical problem to be solved is to reduce the generation of depolymerization and rectifying separation process dipolymer and directly obtain highly purified MCPD, purifies with yield that improves product and the product of removing DMCPD from.
Below be that the present invention solves the problems of the technologies described above concrete technical scheme:
The preparation method of a kind of NSC 7352 and two methyl cyclopentadienes, this method is a raw material with the C9～C10 cut of petroleum cracking system ethylene by-product, its process comprises:
1) raw material carries out the rectification under vacuum separation in rectifying tower, and cat head gets the material of enrichment NSC 7352, and the tower still gets the material of the two methyl cyclopentadienes of enrichment; Tower still temperature is 115～125 ℃; Tower top temperature is 80～90 ℃, tower top pressure is-90～-80KPaG, reflux ratio is 3～10;
2) process 1) the cat head material that obtains gets into the depolymerization rectifying tower and carries out depolymerization rectifying, and cat head gets cyclopentadiene, and the depolymerization reaction temperature of tower still is 180～230 ℃, and tower top temperature is 40～45 ℃, and tower top pressure is 0～10KPaG, and reflux ratio is 1～5;
3) process 1) the tower still material that obtains gets into the depolymerization rectifying tower and carries out depolymerization rectifying; Cat head gets cyclopentadiene; The rectifying section temperature is 70～75 ℃ to be located side line and gets methyl cyclopentadiene, and the depolymerization reaction temperature of tower still is 180～230 ℃, and tower top temperature is 40～45 ℃; Tower top pressure is 0～10KPaG, and reflux ratio is 1～5;
4) process 2) and 3) cyclopentadiene that obtains carries out hot dimerization reaction and get the NSC 7352 product;
5) process 3) methyl cyclopentadiene that obtains carries out hot dimerization reaction and gets two methyl cyclopentadiene products.
Said process 1) described tower still temperature is preferably 120～125 ℃, and tower top temperature is preferably 85～90 ℃; Reflux ratio is preferably 5～8.
Said process 2) described depolymerization reaction temperature is preferably 180～210 ℃, and tower top temperature is preferably 41～43 ℃; Reflux ratio is preferably 1～3.
Said process 3) described depolymerization reaction temperature is preferably 180～210 ℃, and tower top temperature is preferably 41～43 ℃; Being better than most the rectifying section temperature and being 71～73 ℃ locates side line and gets smart methyl cyclopentadiene; Reflux ratio is preferably 1～3.
Above-mentioned 4) and 5) described hot dimerization reaction can adopt method well known in the art to carry out; Can react the continuous or technology intermittently of (single hop temperature of reaction) or reaction of high order (multistage temperature of reaction) for single-stage; Below be that the present invention recommends, its operating procedure is the simplest:
Process 4) described hot dimerization reaction employing mode is intermittently carried out, and temperature of reaction is 55～100 ℃, is preferably 60～80 ℃, and the reaction times is 8～24hr, is preferably 16～21hr, and reaction pressure is 0.5～1.5MPaG, is preferably 0.8～1.2MPaG;
Process 5) described hot dimerization reaction employing mode is intermittently carried out, and temperature of reaction is 60～110 ℃, is preferably 65～85 ℃, and the reaction times is 8～24hr, is preferably 16～21hr, and reaction pressure is 0.5～1.5MPaG, is preferably 0.8～1.2MPaG.
Key problem in technology of the present invention is at first C9～C10 cut to be carried out rectification under vacuum; Make DCPD and DMCPD realize separating, the cat head material of the enrichment DCPD that then rectification under vacuum is obtained and the tower still material of enrichment DMCPD carry out depolymerization rectifying respectively in two depolymerization rectifying tower.The operating principle of rectification under vacuum is that the purity of guaranteeing DCPD makes the cat head material not contain DMCPD, and makes tower still material not contain C6 and C7 component.DCPD and DMCPD have the boiling point of higher boiling point difference and C6, C7 component to be lower than DCPD, and the realization of this operating principle is not difficult.In the depolymerization rectifying tower; The tower still carries out depolymerization reaction; Depolymerization product directly rises to rectifying section with gaseous state and carries out rectified purified; Rectifying does not need extra stripping section to realize the gasification of material, and this makes the probability of depolymerization product generation dimerization reaction greatly reduce, even and can directly return the depolymerization again of tower still in the dipolymer that rectifying section produces yet.Dipolymer in system to go through flow process extremely short, this obviously helps being avoided the generation of polymer.On the other hand, through process 1) rectification under vacuum, C6, C7 component are cut to the material of enrichment DCPD, realize that earlier C6, C7 component separate with DMCPD's.Therefore and after the DCPD depolymerization, the material of CPD and C6, C7 component has bigger boiling-point difference, in the depolymerization rectifying tower of DCPD, can realize separating of CPD and C6, C7 component easily.Realization C6, C7 component are separated with DMCPD's earlier to utilize C6, C7 component with DMCPD the higher boiling point difference to be arranged; Utilize C6, C7 component and CPD to have the higher boiling point difference to realize that again C6, C7 component separate with CPD's then, Here it is solves the key point that prior art can't directly obtain this technical problem of high purity MCPD.
Compared with prior art, the invention has the advantages that depolymerization product rectifying separation process dimerization reaction greatly reduces, there are not recycle stock basically in depolymerization and rectifying separation process, have avoided the generation of polymer, make product yield be improved; The flow scheme improvements of depolymerization and depolymerization product rectifying separation part has also solved the contradiction of C6, C7 component and MCPD separation difficulty, and depolymerization product directly obtains highly purified MCPD after separating, and has removed the refining purification of DMCPD product from.
Accompanying drawing 1 is typical depolymerization of prior art and depolymerization product rectifying separation part process flow diagram; Accompanying drawing 2 is depolymerization of the present invention and depolymerization product rectifying separation part process flow diagram.
To do further description to the present invention through concrete embodiment below; Because the hot dimerization reaction part of CPD of the present invention and MCPD is basic identical with prior art, so embodiment will pay attention to giving an example of depolymerization and depolymerization product rectifying separation process service data.
Embodiment
One, the rectifying separation of depolymerization and depolymerization product
[embodiment 1～10]
Accompanying drawing 2 is seen in the technical process of embodiment 1～10, and raw material C9～C10 cut W1 at first gets into rectifying tower 1 and carries out the rectification under vacuum separation, and the theoretical plate number of rectifying tower 1 is 25, and cat head gets the material W2 of enrichment DCPD, and the tower still gets the material W3 of enrichment DMCPD.The cat head material W2 of rectifying tower 1 gets into depolymerization rectifying tower 2 and carries out depolymerization rectifying, and the theoretical plate number of depolymerization rectifying tower 2 is 15, and cat head gets CPD finished product W4, and the tower still regularly discharges heavy constituent impurity W5.The tower still material W3 of rectifying tower 1 gets into depolymerization rectifying tower 3 and carries out depolymerization rectifying, and the theoretical plate number of depolymerization rectifying tower 3 is 20, and cat head gets CPD finished product W6, and the rectifying section temperature is 70～75 ℃ to be located side line and get MCPD finished product W7, and the tower still regularly discharges heavy constituent impurity W8.CPD that obtains and MCPD finished product cryopreservation under-20～-15 ℃ of temperature is subsequent use.
Raw material W1 is the C9～C10 cut of petroleum cracking system ethylene by-product, and see table 1 main the composition.
The process conditions of each embodiment rectifying tower 1, depolymerization rectifying tower 2 and depolymerization rectifying tower 3 is seen table 2,3 and 4 respectively, and once through yield, the purity of CPD and MCPD are seen table 5.Being defined as of depolymerization and depolymerization product rectifying separation process once through yield:
Table 1.
Table 2.
Table 3.
Table 4.
Table 5.
* the CPD quantum of output in the CPD once through yield is the total amount of depolymerization rectifying tower 2,3.
Two, the hot dimerization of CPD and MCPD
[embodiment 11～16]
Ana is got CPD and the MCPD that embodiment 1～10 obtains and is mixed respectively, obtains purity and be 99.0% CPD raw material and purity and be 98.6% MCPD raw material.Satisfying the batch technology that in useful volume is the batch reactor of 2L, adopts the single-stage reaction respectively carries out hot dimerization reaction and prepares DCPD and DMCPD.With respect to the reaction of high order that segmentation is heated step by step, the reaction times that the single-stage reaction needed is longer, but technology is comparatively simple.Raw material feeds intake by reaction kettle useful volume 80%, and the concrete hot dimerization processes operational condition of each embodiment is seen table 6.Reaction finishes afterwards to carry out with vapor-phase chromatography the compositional analysis of product, and hot dimerization product yield and product composition are seen table 7, table 8.
The product yield of DCPD or DMCPD is defined as:
Table 6.
Table 7.
Table 8.
Because the dimer of CPD or MCPD is in the equilibrium state of depolymerization, hot dimerization with monomer accordingly under normal temperature condition; All the time there is a certain amount of corresponding monomer in DCPD or the DMCPD product; General standard by industry; Allow the monomer of existence≤1wt% in the product, and can corresponding monomer be counted active principle calculating purity.Visible by table 7, table 8, DCPD that the present invention makes or DMCPD product have very and comprise that the impurity of C6, C7 is very low in the ideal quality index, particularly DMCPD, need not to carry out the refining purification of product.
Claims (12)
1. the preparation method of a NSC 7352 and two methyl cyclopentadienes, this method is a raw material with the C9～C10 cut of petroleum cracking system ethylene by-product, its process comprises:
1) raw material carries out the rectification under vacuum separation in rectifying tower, and cat head gets the material of enrichment NSC 7352, and the tower still gets the material of the two methyl cyclopentadienes of enrichment; Tower still temperature is 115～125 ℃; Tower top temperature is 80～90 ℃, tower top pressure is-90～-80KPaG, reflux ratio is 3～10;
2) process 1) the cat head material that obtains gets into the depolymerization rectifying tower and carries out depolymerization rectifying, and cat head gets cyclopentadiene, and the depolymerization reaction temperature of tower still is 180～230 ℃, and tower top temperature is 40～45 ℃, and tower top pressure is 0～10KPaG, and reflux ratio is 1～5;
3) process 1) the tower still material that obtains gets into the depolymerization rectifying tower and carries out depolymerization rectifying; Cat head gets cyclopentadiene; The rectifying section temperature is 70～75 ℃ to be located side line and gets methyl cyclopentadiene, and the depolymerization reaction temperature of tower still is 180～230 ℃, and tower top temperature is 40～45 ℃; Tower top pressure is 0～10KPaG, and reflux ratio is 1～5;
4) process 2) and 3) cyclopentadiene that obtains carries out hot dimerization reaction and get the NSC 7352 product;
5) process 3) methyl cyclopentadiene that obtains carries out hot dimerization reaction and gets two methyl cyclopentadiene products.
2. the preparation method of NSC 7352 according to claim 1 and two methyl cyclopentadienes is characterized in that process 1) described tower still temperature is 120～125 ℃, tower top temperature is 85～90 ℃.
3. the preparation method of NSC 7352 according to claim 1 and two methyl cyclopentadienes is characterized in that process 1) described reflux ratio is 5～8.
4. the preparation method of NSC 7352 according to claim 1 and two methyl cyclopentadienes is characterized in that process 2) described depolymerization reaction temperature is 180～210 ℃, tower top temperature is 41～43 ℃.
5. the preparation method of NSC 7352 according to claim 1 and two methyl cyclopentadienes is characterized in that process 2) described reflux ratio is 1～3.
6. the preparation method of NSC 7352 according to claim 1 and two methyl cyclopentadienes is characterized in that process 3) described depolymerization reaction temperature is 180～210 ℃, tower top temperature is 41～43 ℃.
7. the preparation method of NSC 7352 according to claim 1 and two methyl cyclopentadienes is characterized in that process 3) described rectifying section temperature is 71～73 ℃ and locates side line and get smart methyl cyclopentadiene.
8. the preparation method of NSC 7352 according to claim 1 and two methyl cyclopentadienes is characterized in that process 3) described reflux ratio is 1～3.
9. the preparation method of NSC 7352 according to claim 1 and two methyl cyclopentadienes; It is characterized in that process 4) described hot dimerization reaction adopts mode intermittently to carry out; Temperature of reaction is 55～100 ℃, and the reaction times is 8～24hr, and reaction pressure is 0.5～1.5MPaG.
10. the preparation method of NSC 7352 according to claim 9 and two methyl cyclopentadienes is characterized in that described temperature of reaction is 60～80 ℃, and the reaction times is 16～21hr, and reaction pressure is 0.8～1.2MPaG.
11. the preparation method of NSC 7352 according to claim 1 and two methyl cyclopentadienes; It is characterized in that process 5) described hot dimerization reaction adopts mode intermittently to carry out; Temperature of reaction is 60～110 ℃, and the reaction times is 8～24hr, and reaction pressure is 0.5～1.5MPaG.
12. the preparation method of NSC 7352 according to claim 11 and two methyl cyclopentadienes is characterized in that described temperature of reaction is 65～85 ℃, the reaction times is 16～21hr, and reaction pressure is 0.8～1.2MPaG.
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| CN104276913A (en) * | 2013-07-12 | 2015-01-14 | 中国石油化工股份有限公司 | Method for extracting dicyclopentadiene from ethylene byproduct C9-C10 fractions obtained by petroleum cracking |
| CN104276912A (en) * | 2013-07-12 | 2015-01-14 | 中国石油化工股份有限公司 | Method for separating byproducts C9-C10 fractions in ethylene preparation through petroleum cracking and increasing yield |
| CN104276915A (en) * | 2013-07-12 | 2015-01-14 | 中国石油化工股份有限公司 | Separation method for C9-C10 fractions |
| CN104276919A (en) * | 2013-07-12 | 2015-01-14 | 中国石油化工股份有限公司 | Separation method for ethylene byproducts, namely C9-C10 fractions produced by petroleum cracking |
| CN105585415A (en) * | 2014-10-22 | 2016-05-18 | 中国石油化工股份有限公司 | A method of preparing high-purity dicyclopentadiene through reactive distillation |
| CN111548246A (en) * | 2020-04-23 | 2020-08-18 | 广东新华粤石化集团股份公司 | Method for preparing high-purity dicyclopentadiene from cracking carbon nine fraction |
| CN113200808A (en) * | 2021-04-19 | 2021-08-03 | 山东科荣化工有限公司 | Production device and method for comprehensively utilizing carbon nine raw materials |
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| CN104276913A (en) * | 2013-07-12 | 2015-01-14 | 中国石油化工股份有限公司 | Method for extracting dicyclopentadiene from ethylene byproduct C9-C10 fractions obtained by petroleum cracking |
| CN104276912A (en) * | 2013-07-12 | 2015-01-14 | 中国石油化工股份有限公司 | Method for separating byproducts C9-C10 fractions in ethylene preparation through petroleum cracking and increasing yield |
| CN104276915A (en) * | 2013-07-12 | 2015-01-14 | 中国石油化工股份有限公司 | Separation method for C9-C10 fractions |
| CN104276919A (en) * | 2013-07-12 | 2015-01-14 | 中国石油化工股份有限公司 | Separation method for ethylene byproducts, namely C9-C10 fractions produced by petroleum cracking |
| CN104276919B (en) * | 2013-07-12 | 2018-02-09 | 中国石油化工股份有限公司 | By the separation method of petroleum cracking Crude products.deep process C9~C10 cuts |
| CN104276915B (en) * | 2013-07-12 | 2018-03-06 | 中国石油化工股份有限公司 | A kind of separation method of C9~C10 cuts |
| CN104276912B (en) * | 2013-07-12 | 2018-05-18 | 中国石油化工股份有限公司 | By petroleum cracking Crude products.deep process C9~C10 fraction seperations and the method for improving yield |
| CN105585415A (en) * | 2014-10-22 | 2016-05-18 | 中国石油化工股份有限公司 | A method of preparing high-purity dicyclopentadiene through reactive distillation |
| CN105585415B (en) * | 2014-10-22 | 2017-11-07 | 中国石油化工股份有限公司 | A kind of method that reactive distillation prepares high purity dicyclo pentylene |
| CN111548246A (en) * | 2020-04-23 | 2020-08-18 | 广东新华粤石化集团股份公司 | Method for preparing high-purity dicyclopentadiene from cracking carbon nine fraction |
| CN113200808A (en) * | 2021-04-19 | 2021-08-03 | 山东科荣化工有限公司 | Production device and method for comprehensively utilizing carbon nine raw materials |
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Application publication date: 20120404 |