CN114436751A - Preparation method of methylcyclopentene - Google Patents
Preparation method of methylcyclopentene Download PDFInfo
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- CN114436751A CN114436751A CN202011110285.6A CN202011110285A CN114436751A CN 114436751 A CN114436751 A CN 114436751A CN 202011110285 A CN202011110285 A CN 202011110285A CN 114436751 A CN114436751 A CN 114436751A
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- ATQUFXWBVZUTKO-UHFFFAOYSA-N 1-methylcyclopentene Chemical compound CC1=CCCC1 ATQUFXWBVZUTKO-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 39
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 25
- 239000002904 solvent Substances 0.000 claims abstract description 17
- 238000007670 refining Methods 0.000 claims abstract description 12
- 238000006471 dimerization reaction Methods 0.000 claims abstract description 11
- 239000002994 raw material Substances 0.000 claims abstract description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000005977 Ethylene Substances 0.000 claims abstract description 8
- 238000005336 cracking Methods 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000000463 material Substances 0.000 claims abstract description 8
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 239000003054 catalyst Substances 0.000 claims description 16
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- 238000012691 depolymerization reaction Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- QWJWPDHACGGABF-UHFFFAOYSA-N 5,5-dimethylcyclopenta-1,3-diene Chemical compound CC1(C)C=CC=C1 QWJWPDHACGGABF-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 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 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims 6
- 238000000926 separation method Methods 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 4
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 239000000047 product Substances 0.000 description 21
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000000066 reactive distillation Methods 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 150000005675 cyclic monoalkenes Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
- C07C5/05—Partial hydrogenation
Abstract
The invention discloses a method for preparing methylcyclopentene, which comprises the following steps: 1) depolymerizing and rectifying C9 fraction of raw material ethylene cracking to generate methyl cyclopentadiene; 2) mixing methyl cyclopentadiene, solvent and hydrogen, and then carrying out catalytic hydrogenation reaction; 3) removing trace methylcyclopentadiene in the hydrogenation product through dimerization reaction; 4) separating the material in a methyl cyclopentene refining tower to obtain methyl cyclopentene in the tower top. The preparation method of the invention takes the methylcyclopentene as the solvent of the hydrogenation reaction, adopts the method combining hydrogenation and dimerization reaction, can simplify the separation and refining process, reduce the energy consumption and obtain the high-purity methylcyclopentene with the content of more than 99 percent on the premise of ensuring good hydrogenation reaction effect.
Description
Technical Field
The invention belongs to the technical field of preparation of methylcyclopentene, and particularly relates to a method for preparing methylcyclopentene by using ethylene cracking C9 fraction as a raw material, in particular to a method for preparing high-purity methylcyclopentene by adopting a selective hydrogenation and dimerization reaction combined process.
Background
Methylcyclopentene (MCPE) is a branched cyclic mono-olefin, which is a very rare fine chemical raw material and can be used for producing various insecticides and synthesizing various high-grade tripolymer high polymer materials and the like. In the prior art, references for preparing methylcyclopentene are rare, a general chemically feasible synthesis method does not have economic feasibility, and the current method for selectively hydrogenating Methylcyclopentene (MCPD) has the most industrial application prospect.
Typical prior art, such as US 454760, produces methylcyclopentene by alkylation of Cyclopentadiene (CPD) to produce methylcyclopentadiene, and by selective hydrogenation. For the selective hydrogenation of methylcyclopentadiene to prepare methylcyclopentene, the selective hydrogenation is usually carried out in a solvent, for example, chinese patent CN200510028608.6 discloses a method for preparing methylcyclopentene by continuous hydrogenation of methylcyclopentadiene, the catalyst uses γ -Al2O3 as a carrier and Pd as an active component. The solvent is any one of benzene, toluene, cyclohexane, ethanol, methanol, tertiary amyl alcohol or tertiary butyl alcohol. The pressure of a reaction system is 0.9-1.5 MPa, and the reaction temperature is 60-100 ℃. Partial discharge of reaction liquid and partial external circulation. The heat of reaction is removed by externally circulating the reaction solution. The process method of the invention is a liquid phase reaction, and needs to recover the solvent, thus resulting in long flow and high cost. Therefore, the Chinese patent ZL201210160362.8 adopts a byproduct of hydrogenation reaction, namely methylcyclopentane, as a reaction solvent, and combines with a hydrogenation product material to form an improvement on the separation and refining process of methylcyclopentene, so that the solvent recovery is simplified on the premise of ensuring a good hydrogenation reaction effect. However, because the boiling points of methylcyclopentane and methylcyclopentene are close, a large reflux ratio is required to obtain a high-purity product. In addition, since methylcyclopentadiene and methylcyclopentene are difficult to separate, a side reaction of deep hydrogenation of MCPD to form Methylcyclopentane (MCPA) is generally unavoidable since a high purity methylcyclopentene product can only be obtained if the methylcyclopentene content is as low as possible with a conversion of methylcyclopentadiene of 99.5% or more.
In summary, the conventional methods for preparing methylcyclopentene by hydrogenation of methylcyclopentadiene all have the above disadvantages.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a method for preparing high-purity methylcyclopentene by using an ethylene cracking C9 fraction (namely, mainly dimethylcyclopentadiene) as a raw material. The method takes the methylcyclopentene as a solvent for the hydrogenation reaction, adopts a method combining rectification, hydrogenation and dimerization reaction, and can simplify the separation and refining process and reduce the energy consumption on the premise of ensuring a good hydrogenation reaction effect.
The following is a specific technical solution of the present invention.
The invention provides a preparation method of methylcyclopentene, which comprises the following steps:
(1) the raw material ethylene cracking C9 fraction passes through a depolymerization rectifying tower, dicyclopentadiene and dimethylcyclopentadiene in the fraction are depolymerized under normal pressure, a cyclopentadiene-rich fraction is obtained at the tower top, and a methylcyclopentadiene fraction is obtained at the lateral line; wherein, the depolymerization and rectification tower reaction conditions are that the depolymerization reaction temperature is 170-210 ℃, the tower top temperature is 39-45 ℃, the side line temperature is 70-75 ℃ and the reflux ratio is 1-10;
(2) mixing the methyl cyclopentadiene obtained in the step (1) with a solvent and hydrogen, and then continuously carrying out catalytic hydrogenation reaction on the mixture by a fixed bed catalyst bed, wherein the catalyst is a modified palladium-aluminum catalyst, and the content of the methyl cyclopentadiene in a hydrogenation product is controlled to be 0.5-1%; wherein, the catalytic hydrogenation reaction conditions are that the weight ratio of the solvent to the methyl cyclopentadiene is 5-10: 1, the molar ratio of the hydrogen to the methyl cyclopentadiene is 1.0-2.5: 1, the pressure of a reaction system is 0.5-3.0 MPa, and the liquid hourly volume space velocity LHSV is 3.0-10.0 hr < -1 >; the reaction temperature is 40-100 ℃;
(3) performing thermal dimerization reaction on the hydrogenation product obtained in the step (2) to remove trace methylcyclopentadiene in the hydrogenation product, wherein the reaction temperature is 60-110 ℃, the reaction time is 2-12 hr, and the reaction pressure is 0.5-2.0 MPa;
(4) separating the material obtained in the step (3) by a methylcyclopentene refining tower to obtain a refined methylcyclopentene product at the tower top, and returning the material at the tower bottom to the depolymerization rectifying tower; wherein the temperature of the top of the tower is controlled to be 74-80 ℃, the temperature of the bottom of the tower is controlled to be 80-120 ℃, and the reflux ratio is 5-20.
Further, the depolymerization and rectification tower in the step (1) has the reaction conditions that the depolymerization reaction temperature of a tower kettle is 180-190 ℃, the temperature of a tower top is 41-43 ℃, the temperature of a lateral line is 71-73 ℃ and the reflux ratio is 3-6.
Further, in the modified palladium-aluminum catalyst in the step (2), the weight percentage of palladium in the catalyst is 0.2-0.5%, the assistant is platinum, and the weight ratio of palladium to platinum is 1: 0.1-1: 0.5. (commercially available, e.g., QSH001 and QSH006 from the Qilu petrochemical institute)
Further, the weight ratio of the solvent to the methyl cyclopentadiene in the step (2) is 6-8: 1, the molar ratio of the hydrogen to the methyl cyclopentadiene is 1.2-1.8: 1, the pressure of a reaction system is 1.0-2.5 MPa, and the liquid hourly space velocity is 4.0-6.0 hr-1(ii) a The reaction temperature is 55-80 ℃.
Further, the solvent is methyl cyclopentene.
Further, the reaction temperature in the step (3) is 65-85 ℃, the reaction time is 4-6 hr, and the reaction pressure is 1.0-1.5 MPa.
Further, the temperature of the top of the tower in the step (4) is controlled to be 75-78 ℃, the temperature of the bottom of the tower is controlled to be 97-103 ℃, and the reflux ratio is 2-5.
For the selective hydrogenation process of methyl cyclopentadiene, the inventor finds out through a large number of experiments that the modified palladium-aluminum catalyst has better hydrogenation selectivity for the hydrogenation reaction of methyl cyclopentadiene, can completely inhibit the hydrogenation reaction of methyl cyclopentene under the condition of controlling a certain reaction depth, does not influence the hydrogenation of methyl cyclopentene, and basically keeps an effective equilibrium state. When the concentration of the methylcyclopentadiene is low (< 1%), the probability of the methylcyclopentene being adsorbed to different active sites is reduced, and the further hydrogenation of the methylcyclopentene can be difficult to control by appropriate hydrogenation conditions, and the residual methylcyclopentadiene can be removed by a mature dimerization technique. In addition, the invention also adopts the methyl cyclopentene as a reaction solvent, so that one component is reduced in a hydrogenation reaction system, and a foundation is laid for simplifying the refining and separation of the hydrogenation product.
Compared with the prior art, the invention adopts a rectifying tower to finish the separation and refining of the solvent and the hydrogenation product on the premise of ensuring good hydrogenation reaction effect, simplifies the separation and refining system, reduces the equipment investment and the operation cost, and obtains the high-purity methylcyclopentene with the content of more than 99 percent.
Drawings
FIG. 1 is a schematic diagram of the process for preparing high purity methylcyclopentene from a C9 fraction obtained by cracking ethylene according to the present invention.
Detailed Description
The present invention will be described in detail with reference to specific examples. The following examples will assist those skilled in the art in further understanding the invention, but are not intended to limit the invention in any way. It should be noted that it would be apparent to those skilled in the art that several modifications and improvements can be made without departing from the inventive concept. All falling within the scope of the present invention.
The catalysts used in the following examples are commercially available.
[ examples 1 to 10 ]
The process flow of the embodiment 1-10 is shown in fig. 1, a raw material W1 firstly enters a reactive distillation column for depolymerization reaction, a depolymerization product W2 rich in CPD is obtained at the top of the column, the number of theoretical plates of the reactive distillation column is 50, a depolymerization product W3 rich in MCPD can be obtained at the side line, and heavy component impurities are periodically discharged from the bottom of the column. W3 enters a fixed bed reactor for hydrogenation to obtain a hydrogenation product W4, and W4 is separated by a dimerization reactor and a methyl cyclopentene refining tower to obtain a MCPE finished product W5.
The reaction process is as follows:
(1) the raw material ethylene cracking C9 fraction passes through a depolymerization rectifying tower, dicyclopentadiene and dimethylcyclopentadiene in the fraction are depolymerized under normal pressure, a cyclopentadiene-rich fraction is obtained at the tower top, and a methylcyclopentadiene fraction is obtained at the lateral line;
(2) mixing the methyl cyclopentadiene obtained in the step (1) with a solvent and hydrogen, and then continuously carrying out catalytic hydrogenation reaction on the mixture by a fixed bed catalyst bed, wherein the catalyst is a modified palladium-aluminum catalyst, and the content of the methyl cyclopentadiene in a hydrogenation product is controlled to be 0.5-1%;
(3) carrying out thermal dimerization reaction on the hydrogenation product obtained in the step (2) to remove trace methylcyclopentadiene in the hydrogenation product;
(4) and (4) separating the material obtained in the step (3) by a methylcyclopentene refining tower, obtaining a refined methylcyclopentene product at the tower top, and returning the material at the tower bottom to the depolymerization and rectification tower.
The raw material W1 is ethylene cracking C9 fraction, the main composition is shown in Table 1, the process operating conditions of the raw material W1 sequentially passing through a reaction rectifying tower, a hydrogenation reactor, a dimerization reactor and a methyl cyclopentene refining tower in each example are respectively shown in tables 2, 3, 4 and 5, the composition analysis of the product is carried out by gas chromatography after the reaction is finished, and the yield and the purity of the methyl cyclopentene product are shown in Table 1
Table 6. The product yield of methylcyclopentene is defined as:
TABLE 1 Main Components of the raw materials (W1)
TABLE 2 Deploymerization rectification column separation conditions for each example
| Temperature at the top of column (. degree.C.) | Column bottom temperature (. degree. C.) | Side line temperature (. degree. C.) | Reflux ratio | |
| Example 1 | 39 | 170 | 70 | 1 |
| Example 2 | 40 | 175 | 71 | 2 |
| Example 3 | 40.5 | 177 | 71.5 | 2.2 |
| Example 4 | 40.6 | 180 | 71.6 | 2.6 |
| Example 5 | 40.8 | 179 | 71.8 | 3.5 |
| Example 6 | 41.0 | 181 | 72 | 4 |
| Example 7 | 41.2 | 182 | 72.4 | 3.0 |
| Example 8 | 41.6 | 183 | 72.7 | 5 |
| Example 9 | 42 | 185 | 73 | 8 |
| Example 10 | 43 | 210 | 75 | 10 |
TABLE 3 reaction conditions in the fixed bed reactor of each example
TABLE 4 reaction conditions in dimerization reactor of examples
TABLE 5 separation conditions of methylcyclopentene purification columns in examples
| Temperature at the top of column (. degree.C.) | Column bottom temperature (. degree. C.) | Reflux ratio | |
| Example 1 | 95 | 74 | 1 |
| Example 2 | 97 | 75 | 2 |
| Example 3 | 98 | 75.5 | 3.0 |
| Example 4 | 99 | 76 | 2.5 |
| Example 5 | 100 | 76.5 | 3.5 |
| Example 6 | 101 | 76.8 | 4.5 |
| Example 7 | 102 | 77 | 4.0 |
| Example 8 | 103 | 77.5 | 8 |
| Example 9 | 104 | 78 | 5 |
| Example 10 | 105 | 80 | 10 |
TABLE 6 methylcyclopentene yield and purity of the product obtained in each example
| Methylcyclopentene yield (%) | Methylcyclopentene purity (%) | |
| Example 1 | 80.1 | 99.0 |
| Example 2 | 81.3 | 99.2 |
| Example 3 | 83.2 | 99.4 |
| Example 4 | 84.9 | 99.5 |
| Example 5 | 85.8 | 99.4 |
| Example 6 | 85.1 | 99.3 |
| Example 7 | 84.8 | 99.4 |
| Example 8 | 83.1 | 99.5 |
| Example 9 | 81.6 | 98.9 |
| Example 10 | 80.3 | 98.5 |
While the preferred embodiments of the present invention have been described in detail, it will be understood by those skilled in the art that the invention is not limited thereto, and that various changes and modifications may be made without departing from the spirit of the invention, and the scope of the appended claims is to be accorded the full scope of the invention.
Claims (7)
1. A method for preparing methylcyclopentene, comprising:
(1) the raw material ethylene cracking C9 fraction passes through a depolymerization rectifying tower, dicyclopentadiene and dimethylcyclopentadiene in the fraction are depolymerized under normal pressure, a cyclopentadiene-rich fraction is obtained at the tower top, and a methylcyclopentadiene fraction is obtained at the lateral line; wherein, the depolymerization and rectification tower reaction conditions are that the depolymerization reaction temperature is 170-210 ℃, the tower top temperature is 39-45 ℃, the side line temperature is 70-75 ℃ and the reflux ratio is 1-10;
(2) mixing the methyl cyclopentadiene obtained in the step (1) with a solvent and hydrogen, and then continuously carrying out catalytic hydrogenation reaction on the mixture by a fixed bed catalyst bed, wherein the catalyst is a modified palladium-aluminum catalyst, and the content of the methyl cyclopentadiene in a hydrogenation product is controlled to be 0.5-1%; wherein, the catalytic hydrogenation reaction conditions are that the weight ratio of the solvent to the methyl cyclopentadiene is 5-10: 1, the molar ratio of the hydrogen to the methyl cyclopentadiene is 1.0-2.5: 1, the pressure of a reaction system is 0.5-3.0 MPa, and the liquid hourly volume space velocity LHSV is 3.0-10.0 hr < -1 >; the reaction temperature is 40-100 ℃;
(3) carrying out thermal dimerization reaction on the hydrogenation product obtained in the step (2), wherein the reaction temperature is 60-110 ℃, the reaction time is 2-12 hr, and the reaction pressure is 0.5-2.0 MPa;
(4) separating the material obtained in the step (3) by a methylcyclopentene refining tower to obtain a refined methylcyclopentene product at the tower top, and returning the material at the tower bottom to the depolymerization rectifying tower; wherein the temperature of the top of the tower is controlled to be 74-80 ℃, the temperature of the bottom of the tower is controlled to be 80-120 ℃, and the reflux ratio is 5-20.
2. The process according to claim 1, wherein the reaction mixture comprises: the depolymerization and rectification tower in the step (1) has the reaction conditions that the depolymerization reaction temperature of a tower kettle is 180-190 ℃, the top temperature is 41-43 ℃, the side temperature is 71-73 ℃ and the reflux ratio is 3-6.
3. The process according to claim 1, wherein the reaction mixture comprises: in the modified palladium-aluminum catalyst in the step (2), the weight percentage of palladium in the catalyst is 0.2-0.5%, the assistant is platinum, and the weight ratio of palladium to platinum is 1: 0.1-1: 0.5.
4. the process according to claim 1, wherein the reaction mixture comprises: the weight ratio of the solvent to the methyl cyclopentadiene in the step (2) is 6-8: 1, the molar ratio of the hydrogen to the methyl cyclopentadiene is 1.2-1.8: 1, the pressure of a reaction system is 1.0-2.5 MPa, and the liquid hourly space velocity is 4.0-6.0 hr-1(ii) a The reaction temperature is 55-80 ℃.
5. The process according to claim 1 or 4, wherein the reaction mixture comprises: the solvent is methyl cyclopentene.
6. The process according to claim 1, wherein the reaction mixture comprises: the reaction temperature in the step (3) is 65-85 ℃, the reaction time is 4-6 hr, and the reaction pressure is 1.0-1.5 MPa.
7. The process according to claim 1, wherein the reaction mixture comprises: the temperature of the top of the tower in the step (4) is controlled to be 75-78 ℃, the temperature of the bottom of the tower is controlled to be 97-103 ℃, and the reflux ratio is 2-5.
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| CN115974639A (en) * | 2023-03-21 | 2023-04-18 | 新疆天利石化股份有限公司 | Method for co-production of methylcyclopentane by cracking carbon nine hydrogenation device and pentane device |
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