CN114456031A - Preparation method of polycyclopentadiene - Google Patents
Preparation method of polycyclopentadiene Download PDFInfo
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- CN114456031A CN114456031A CN202210186624.1A CN202210186624A CN114456031A CN 114456031 A CN114456031 A CN 114456031A CN 202210186624 A CN202210186624 A CN 202210186624A CN 114456031 A CN114456031 A CN 114456031A
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- 238000002360 preparation method Methods 0.000 title abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 16
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 94
- 238000000926 separation method Methods 0.000 claims description 36
- 239000000295 fuel oil Substances 0.000 claims description 32
- 239000002994 raw material Substances 0.000 claims description 20
- 238000006116 polymerization reaction Methods 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 7
- 238000012691 depolymerization reaction Methods 0.000 claims description 5
- 238000007599 discharging Methods 0.000 claims description 5
- 238000005086 pumping Methods 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 description 10
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 6
- 150000001993 dienes Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940116229 borneol Drugs 0.000 description 1
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
- C07C4/22—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by depolymerisation to the original monomer, e.g. dicyclopentadiene to cyclopentadiene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F132/00—Homopolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F132/02—Homopolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings
- C08F132/06—Homopolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings having two or more carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Analytical Chemistry (AREA)
- Water Supply & Treatment (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the field of methods for preparing polycyclopentadiene, in particular to a method for improving the preparation efficiency of polycyclopentadiene.
Description
Technical Field
The invention relates to the field of methods for preparing polycyclopentadiene, in particular to a method for improving the preparation efficiency of polycyclopentadiene.
Background
Coarse dicyclic, etc. and contains great amount of dicyclopentadiene, which may be used as material for extracting dicyclopentadiene. The by-product cracked diolefin of the ethylene plant contains a large amount of dicyclopentadiene, and the total amount of dicyclopentadiene can reach more than 40 percent of the total amount of cracked diolefin. Because dicyclopentadiene can be decomposed into cyclopentadiene at a certain temperature, cyclopentadiene can be easily separated from other diolefin fractions, so that the prior art for producing dicyclopentadiene by cracking diolefin adopts a technological route of depolymerization, separation and dimerization refining.
In the process of extracting dicyclopentadiene from the crude dicyclic product, the crude dicyclic product is mostly depolymerized by directly heating, when the temperature is too high in the depolymerization process, the depolymerized cyclopentadiene can be generated into dimers or trimers to be attached to a heating rod, and the heating rod is easy to ignite and even explode, so that the common depolymerization temperature is 120-180 ℃, the single-pass conversion rate of dicyclopentadiene is lower, and in order to improve the yield of the device, a reaction raw material circulating heating mode is usually adopted to improve the reaction time, but the problem of polymerization caused by too long retention time of other active components (such as methyl styrene and the like) in a high-temperature area is brought, and a large amount of diolefin active components are polymerized into heavy components.
At present, in the production process of the polycyclopentadiene, the depolymerization temperature is reduced in order to ensure the production safety, and further the production efficiency is low.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provide a preparation method of polycyclopentadiene with high purification efficiency.
The invention is realized by the following technical scheme: a method for preparing polycyclopentadiene comprises the following steps:
step 1: depolymerizing, namely putting the raw material containing cyclopentadiene into a depolymerization kettle for high-temperature depolymerization to obtain gas-phase cyclopentadiene and undeployed heavy oil, pumping the gas-phase cyclopentadiene from the top of the kettle, and discharging the heavy oil from the bottom of the kettle;
step 2: separating, namely conveying the gas-phase cyclopentadiene obtained in the step 1 into a separation tower for secondary separation, wherein the temperature in the separation tower is lower than that in the depolymerization kettle, obtaining further purified gas-phase cyclopentadiene and heavy oil after the secondary separation, and separating the heavy oil from the bottom of the separation tower;
and step 3: and (3) polymerizing, namely cooling and liquefying the gas-phase cyclopentadiene obtained in the step (2), and conveying the liquefied cyclopentadiene into a polymerization tank for gathering to form the polycyclopentadiene.
Further, the depolymerization kettle in the step 1 is operated at negative pressure, and the depolymerization temperature is 180-220 ℃.
Further, the temperature at the bottom of the separation column in the step 2 is 120-150 ℃, and the temperature at the top of the separation column is 100-110 ℃.
Further, the cooling temperature in the step 3 is 60-90 ℃, and the temperature in the polymerization tank is 80-90 ℃.
Further, the heavy oil obtained in the step 1 and the step 2 is collected and then conveyed to a depolymerization kettle through a pipeline for secondary depolymerization reaction.
The invention has the beneficial effects that: adopt the depolymerization cauldron to carry out high temperature heating to the raw materials when the depolymerization, promote the depolymerization efficiency and the speed of raw materials, and then promote the preparation efficiency of polycyclopentadiene, compare with prior art and can also avoid the raw materials to carry out manifold cycles heating depolymerization when promoting preparation efficiency.
Drawings
FIG. 1 is a flow chart of the present invention.
Detailed Description
In the description of the present invention, it should also be noted that, unless otherwise explicitly specified or limited, the terms "disposed," "mounted," "connected," and "connected" are to be construed broadly and may, for example, be fixedly connected, detachably connected, or integrally connected; can be mechanically or electrically connected; they may be connected directly or indirectly through intervening media, or they may be interconnected between two elements. The specific meanings of the above terms in the present invention can be understood in specific cases to those skilled in the art.
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
A method for preparing polycyclopentadiene comprises the following steps:
preparing raw materials, wherein the raw materials comprise the following components: 1.22%, X1: 1.31, dicyclopentadiene: 86.38%, mixing the borneol: 1.12% and other impurities about 10%,
step 1: depolymerizing, namely putting 1000g of raw material containing cyclopentadiene into a depolymerization kettle for high-temperature depolymerization to obtain 126g of gas-phase cyclopentadiene and undeployed heavy oil, pumping the gas-phase cyclopentadiene from the top of the kettle, and discharging the heavy oil from the bottom of the kettle, so that the mass of the gas-phase cyclopentadiene can be calculated to be 874g, the depolymerization kettle is operated at negative pressure, and the depolymerization temperature is 180-220 ℃;
step 2: separating, namely conveying 874g of the gas-phase cyclopentadiene obtained in the step 1 into a separation tower for secondary separation, wherein the temperature in the separation tower is lower than the temperature in a depolymerization kettle, and obtaining 36g of further purified gas-phase cyclopentadiene and heavy oil after secondary separation, so that the mass of the gas-phase cyclopentadiene is 838g, the heavy oil is separated from the bottom of the separation tower, the temperature at the bottom of the separation tower is 120-150 ℃, and the temperature at the top of the separation tower is 100-110 ℃;
and step 3: and (3) polymerization, namely cooling the gas-phase cyclopentadiene obtained in the step (2) to 30-90 ℃, liquefying, conveying the liquefied cyclopentadiene into a polymerization tank, and keeping the temperature in the polymerization tank at 80-90 ℃ to form 838g of polycyclopentadiene.
162g of the heavy oil obtained in the step 1 and the step 2 is collected and then conveyed to a depolymerization kettle through a pipeline for secondary depolymerization reaction to obtain 16g of polycyclopentadiene, the heavy oil produced in the production process in the step 1 and the step 2 still contains a small amount of cyclopentadiene, and the heavy oil is collected and then subjected to secondary depolymerization to avoid waste of raw materials.
In summary, the total amount of polycyclopentadiene obtained by the two preparations is: 838+16=854 g;
the purity of the product is detected by a high performance liquid chromatograph, and the initial degree is 98.5%;
yield of polycyclopentadiene = (854 × 98.5%)/(1000 × 86.38%) = 97.4%.
Example 2
The raw materials and the components used in the method are the same as those in the embodiment 1;
step 1: depolymerizing, namely putting 300Kg of raw material containing cyclopentadiene into a depolymerization kettle for high-temperature depolymerization to obtain 38.4Kg of gas-phase cyclopentadiene and undeployed heavy oil, pumping the gas-phase cyclopentadiene away from the top of the kettle, and discharging the heavy oil from the bottom of the kettle, so that the mass of the gas-phase cyclopentadiene can be calculated to be 261.6Kg, the depolymerization kettle is operated under negative pressure, and the depolymerization temperature is 180-220 ℃;
step 2: separating, namely conveying 261.6Kg of gas-phase cyclopentadiene obtained in the step 1 into a separation tower for secondary separation, wherein the temperature in the separation tower is lower than that in the depolymerization kettle, and obtaining 12.85Kg of further purified gas-phase cyclopentadiene and heavy oil after secondary separation, so that the mass of the gas-phase cyclopentadiene is calculated to be 248.75Kg, the heavy oil is separated from the bottom of the separation tower, the temperature at the bottom of the separation tower is 120-150 ℃, and the temperature at the top of the separation tower is 100-110 ℃;
and step 3: and (3) polymerization, namely cooling the gas-phase cyclopentadiene obtained in the step (2) to 30-90 ℃, liquefying, conveying the liquefied cyclopentadiene into a polymerization tank, and keeping the temperature in the polymerization tank at 80-90 ℃ to form 248.75Kg of polycyclopentadiene.
51.25Kg of heavy oil obtained in the step 1 and the step 2 is collected and then conveyed into a depolymerization kettle through a pipeline for secondary depolymerization reaction to obtain 1.4Kg of polycyclopentadiene, the heavy oil produced in the production process in the step 1 and the step 2 still contains a small amount of cyclopentadiene, and the heavy oil is collected and then subjected to secondary depolymerization to avoid waste of raw materials.
In summary, the total amount of polycyclopentadiene obtained by the two preparations is: 248.75+1.4=250.15 g;
the purity of the product is detected by a high performance liquid chromatograph, and the initial degree is 97.8%;
yield of polycyclopentadiene = (250.15 × 97.8%)/(300 × 86.38%) = 96.5%.
Example 3
The raw materials and the component compositions adopted by the method are the same as those adopted by the embodiments 1 and 2;
step 1: depolymerizing, namely putting 800Kg of raw material containing cyclopentadiene into a depolymerization kettle for high-temperature depolymerization to obtain 103.8Kg of gas-phase cyclopentadiene and undeployed heavy oil, pumping the gas-phase cyclopentadiene away from the kettle top, and discharging the heavy oil from the kettle bottom, so that the mass of the gas-phase cyclopentadiene can be calculated to be 696.2Kg, the depolymerization kettle is operated at negative pressure, and the depolymerization temperature is 180-220 ℃;
step 2: separating, namely conveying 696.2Kg of the gas-phase cyclopentadiene obtained in the step 1 to a separation tower for secondary separation, wherein the temperature in the separation tower is lower than the temperature in a depolymerization kettle, and obtaining 36.8Kg of further purified gas-phase cyclopentadiene and heavy oil after secondary separation, so that the mass of the gas-phase cyclopentadiene is calculated to be 659.4Kg, the heavy oil is separated from the bottom of the separation tower, the temperature at the bottom of the separation tower is 120-150 ℃, and the temperature at the top of the separation tower is 100-110 ℃;
and step 3: and (3) polymerization, namely cooling the gas-phase cyclopentadiene obtained in the step (2) to 30-90 ℃, liquefying, conveying the liquefied cyclopentadiene into a polymerization tank, and keeping the temperature in the polymerization tank at 80-90 ℃ to form 659.4Kg of polycyclopentadiene.
The total 140.6Kg of heavy oil obtained in the step 1 and the step 2 is collected and then conveyed to a depolymerization kettle through a pipeline for secondary depolymerization reaction to obtain 28.9Kg of polycyclopentadiene, the heavy oil produced in the production process in the step 1 and the step 2 still contains a small amount of cyclopentadiene, and the heavy oil is collected and then subjected to secondary depolymerization to avoid waste of raw materials.
In summary, the total amount of polycyclopentadiene obtained by the two preparations is: 659.4+28.9=688.3 g;
the purity of the product is detected by a high performance liquid chromatograph, and the initial degree is 98.1%;
yield of polycyclopentadiene = (688.3 × 98.1%)/(800 × 86.38%) = 97.7%.
In summary, the following table is obtained:
| sequence number entry | Raw material (KG) | Polycyclopentadiene (Kg) | Purity of | Yield of |
| Example 1 | 1 | 0.854 | 98.5% | 97.4% |
| Example 2 | 300 | 250.15 | 97.8% | 96.5% |
| Example 3 | 800 | 688.3 | 98.1% | 97.7% |
In conclusion, the purity of the embodiment 1 in the embodiments 1 to 3 is the highest, i.e. the embodiment 1 is the best embodiment of the technical scheme disclosed by the invention;
example 1 is an experimental case, a small amount of raw materials is used for purification experiment;
example 2 is the weight of raw materials put in the first mass production;
example 3 is the weight of raw material put in each time after mass production;
the purity of the polycyclopentadiene prepared in 3 embodiments is about 98%, the stirring range is not large, and the purity data of the polycyclopentadiene prepared by the preparation method disclosed by the invention is stable in experiments, first production and mass production.
Finally, it should be noted that: although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that modifications may be made to the embodiments or portions thereof without departing from the spirit and scope of the invention.
Claims (5)
1. A method for preparing polycyclopentadiene is characterized by comprising the following steps: the method comprises the following steps:
step 1: depolymerizing, namely putting the raw material containing cyclopentadiene into a depolymerization kettle for high-temperature depolymerization to obtain gas-phase cyclopentadiene and undeployed heavy oil, pumping the gas-phase cyclopentadiene from the top of the kettle, and discharging the heavy oil from the bottom of the kettle;
step 2: separating, namely conveying the gas-phase cyclopentadiene obtained in the step 1 into a separation tower for secondary separation, wherein the temperature in the separation tower is lower than that in the depolymerization kettle, obtaining further purified gas-phase cyclopentadiene and heavy oil after the secondary separation, and separating the heavy oil from the bottom of the separation tower;
and step 3: and (3) polymerizing, namely cooling and liquefying the gas-phase cyclopentadiene obtained in the step (2), and conveying the liquefied cyclopentadiene into a polymerization tank for gathering to form the polycyclopentadiene.
2. The method for preparing polycyclopentadiene as claimed in claim 1, wherein: in the step 1, the depolymerization kettle is operated at negative pressure, and the depolymerization temperature is 180-220 ℃.
3. The method for preparing polycyclopentadiene as claimed in claim 1, wherein: the temperature of the bottom of the separation tower in the step 2 is 120-150 ℃, and the temperature of the top of the separation tower is 100-110 ℃.
4. The method for preparing polycyclopentadiene as claimed in claim 1, wherein: the cooling temperature in the step 3 is 60-90 ℃, and the temperature in the polymerization tank is 80-90 ℃.
5. The method for preparing polycyclopentadiene as claimed in claim 1, wherein: and (3) collecting the heavy oil obtained in the step (1) and the step (2), and conveying the heavy oil to a depolymerization kettle through a pipeline for secondary depolymerization reaction.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101597205A (en) * | 2008-06-06 | 2009-12-09 | 上海宝钢化工有限公司 | A kind of method from coking byproduct production dicyclopentadiene |
| CN102010285A (en) * | 2010-11-02 | 2011-04-13 | 宁波职业技术学院 | Method for extracting methyl cyclopentadiene from ethylene cracked C9 heavy fractions |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101597205A (en) * | 2008-06-06 | 2009-12-09 | 上海宝钢化工有限公司 | A kind of method from coking byproduct production dicyclopentadiene |
| CN102010285A (en) * | 2010-11-02 | 2011-04-13 | 宁波职业技术学院 | Method for extracting methyl cyclopentadiene from ethylene cracked C9 heavy fractions |
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