CN113248341B - Device and process for preparing methylcyclopentane from cyclohexene - Google Patents
Device and process for preparing methylcyclopentane from cyclohexene Download PDFInfo
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- CN113248341B CN113248341B CN202110559749.XA CN202110559749A CN113248341B CN 113248341 B CN113248341 B CN 113248341B CN 202110559749 A CN202110559749 A CN 202110559749A CN 113248341 B CN113248341 B CN 113248341B
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- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 title claims abstract description 162
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 title claims abstract description 90
- 238000004519 manufacturing process Methods 0.000 title description 7
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 64
- 238000010992 reflux Methods 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000000463 material Substances 0.000 claims abstract description 14
- 239000007791 liquid phase Substances 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 239000007792 gaseous phase Substances 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 39
- ATQUFXWBVZUTKO-UHFFFAOYSA-N 1-methylcyclopentene Chemical compound CC1=CCCC1 ATQUFXWBVZUTKO-UHFFFAOYSA-N 0.000 claims description 37
- 239000003054 catalyst Substances 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000002808 molecular sieve Substances 0.000 claims description 16
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 16
- 238000007599 discharging Methods 0.000 claims description 5
- 238000011144 upstream manufacturing Methods 0.000 claims description 4
- 238000011068 loading method Methods 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 description 10
- 239000013067 intermediate product Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 230000003139 buffering effect Effects 0.000 description 3
- 230000008707 rearrangement Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 208000012839 conversion disease Diseases 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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
-
- 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
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/29—Rearrangement of carbon atoms in the hydrocarbon skeleton changing the number of carbon atoms in a ring while maintaining the number of rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/74—Iron group metals
- C07C2523/755—Nickel
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The utility model provides a device of cyclohexene preparation methyl cyclopentane, includes at least one cyclohexene reactor, rectifying column, hydrogenation ware, sets up the agitator in the cyclohexene reactor, and the feed inlet of cyclohexene reactor is used for linking to each other with the cyclohexene source, and the bin outlet of cyclohexene reactor passes through the row material pipe and links to each other with the rectifying column, is equipped with first valve on this row material pipe, the top bin outlet of rectifying column is through condenser, the back flow with the back flow mouth of rectifying column links to each other, sets up the reflux pump on this back flow, sets up the second valve on the back flow, and is located the low reaches of reflux pump, and hydrogenation ware's liquid phase feed inlet passes through the inlet pipe and links to each other with the back flow, is located between reflux pump and the second valve, sets up the third valve on the inlet pipe, hydrogenation ware's gaseous phase feed inlet is located hydrogenation ware's top, hydrogenation ware's bin outlet is located hydrogenation ware's bottom. The invention has simple structure and operation method, and can effectively meet the actual demands of enterprises by preparing methylcyclopentane from cyclohexene with wide sources.
Description
Technical Field
The invention relates to the field of chemical industry, in particular to a device and a process for preparing methylcyclopentane from cyclohexene.
Background
Methylcyclopentane is an organic compound and is a colorless transparent liquid at normal temperature and pressure. The method is mainly used as a reagent and a chemical synthesis raw material.
At present, the industrial production of methylcyclopentane mainly comprises C in the refining industry 6 The catalyst is obtained through further catalytic reaction and rectification, and has the advantages of long process flow, expensive catalyst and complex reaction product.
Therefore, how to design a production method of methylcyclopentane with simple process and mild reaction is a problem to be solved by the person skilled in the art.
Disclosure of Invention
One of the purposes of the invention is to provide a device for preparing methylcyclopentane from cyclohexene, which has a simple structure and an operation method, can prepare methylcyclopentane from cyclohexene with wide sources, and effectively meets the actual demands of enterprises.
The second purpose of the invention is to provide a process for preparing methyl cyclopentane on the basis of the device, which has the advantages of simple reaction route, low price and easy obtainment of the used catalyst, mild reaction condition and easy separation of reaction products on the basis of ensuring the conversion rate, and no three wastes generated in the reaction process and high environmental friendliness.
The technical scheme for realizing one of the purposes of the invention is as follows: the utility model provides a device of cyclohexene preparation methyl cyclopentane, includes at least one cyclohexene reactor, at least one rectifying column, at least one hydrogenation reactor, set up the agitator in the cyclohexene reactor, the feed inlet of cyclohexene reactor is used for linking to each other with the cyclohexene source, the bin outlet of cyclohexene reactor passes through the row material pipe and links to each other with the rectifying column, is equipped with first valve on this row material pipe, the top bin outlet of rectifying column is through condenser, the back flow with the back flow of rectifying column links to each other, sets up the reflux pump on this back flow, sets up the second valve on the back flow, and is located the low reaches of reflux pump, the liquid phase feed inlet of hydrogenation reactor links to each other with the back flow through the inlet pipe, is located between reflux pump and the second valve, sets up the third valve on the inlet pipe, the gaseous phase feed inlet of hydrogenation reactor is located the top of hydrogenation reactor for link to each other with the hydrogen source, the bin outlet of hydrogenation reactor is located the bottom of hydrogenation reactor.
Furthermore, the rectifying towers are connected in parallel and/or in series.
Further, a material outlet at the bottom of the rectifying tower is connected with a material inlet of the cyclohexene reactor through a circulating pipeline, and a circulating pump is arranged on the circulating pipeline.
Further, a fourth valve is arranged on the circulating pipeline and is positioned at the downstream of the circulating pump.
Preferably, the reflux tube is provided with a reflux tank upstream of the reflux pump.
The second technical scheme for realizing the purpose of the invention is that the method for preparing methylcyclopentane by adopting any one of the devices comprises the following steps:
1) Cyclohexene and a molecular sieve catalyst are taken and reacted in a cyclohexene reactor to obtain a mixed material containing the molecular sieve catalyst, cyclohexene and methylcyclopentene, wherein the reaction temperature is 100-160 ℃, and the pressure is 0.3-0.8MPa;
2) Discharging the mixed material obtained in the step 1) to a rectifying tower, controlling the temperature of the top of the rectifying tower to be 35-55 ℃, controlling the temperature of the tower kettle to be 60-80 ℃, controlling the opening of a second valve and the opening of a third valve to enable the reflux ratio of the rectifying tower to be 10-20, and separating to obtain methylcyclopentene to enter a hydrogenation reactor through a feed pipe;
3) The methyl cyclopentene reacts with hydrogen under the action of a hydrogenation catalyst to obtain methyl cyclopentane, the methyl cyclopentane is discharged from the bottom of the hydrogenation reactor, the reaction temperature is 100-180 ℃, and the pressure is 1-2MPa.
7. The process of claim 6 wherein the molecular sieve catalyst of step 1) has a particle size of 1 to 5um, a Si/Al molar ratio of 20 to 40, and a loading factor of 0.25 to 0.4 in the reactor
8. The process according to claim 6, wherein the reaction temperature in step 1) is 110 to 130℃and the pressure is 0.4 to 0.6MPa
9. The method according to claim 6, wherein the top temperature of the rectifying tower in the step 2) is 40-50 ℃, the bottom temperature is 65-75 ℃, and the reflux ratio of the rectifying tower is 10-15.
10. The process of claim 6, wherein the hydrogenation catalyst of step 3) is Ni, the molar ratio of hydrogen to methylcyclopentene is 1-2, the reaction temperature is 120-160 ℃, and the pressure is 1.2-1.8MPa.
The technical scheme has the following beneficial effects:
1. the device for preparing methylcyclopentane from cyclohexene comprises at least one cyclohexene reactor, at least one rectifying tower and at least one hydrogenation reactor, wherein the cyclohexene reactor is used for enabling added cyclohexene to react and isomerize under the action of a molecular sieve catalyst to generate methylcyclopentene, the rectifying tower is used for separating and obtaining methylcyclopentene, and the hydrogenation reactor is used for enabling the added methylcyclopentene to react with hydrogen under the action of a hydrogenation catalyst to generate methylcyclopentane. The cyclohexene reactor is internally provided with a stirrer, and the feed inlet of the cyclohexene reactor is used for being connected with a cyclohexene source, so that the cyclohexene as a raw material and the molecular sieve catalyst are uniformly mixed. The discharge port of the cyclohexene reactor is connected with the rectifying tower through a discharge pipe, and a first valve is arranged on the discharge pipe and used for discharging the generated mixture into the rectifying tower. The top discharge port of the rectifying tower is connected with the reflux port of the rectifying tower through a condenser and a reflux pipe, the reflux pipe is provided with a reflux pump, the reflux pipe is provided with a second valve and is positioned at the downstream of the reflux pump, and after vapor-phase methylcyclopentane separated in the rectifying tower is condensed into a liquid state, a part of the vapor-phase methylcyclopentane is refluxed, so that the purity of the vapor-phase methylcyclopentane separated can be effectively improved. The liquid phase feed inlet of the hydrogenation reactor is connected with the return pipe through the feed pipe and is positioned between the return pump and the second valve, the third valve is arranged on the feed pipe, and the purpose of controlling the return ratio is realized by controlling the opening of the second valve and the opening of the third valve. The gas phase feed inlet of the hydrogenation reactor is positioned at the top of the hydrogenation reactor and is used for being connected with a hydrogen source, the discharge outlet of the hydrogenation reactor is positioned at the bottom of the hydrogenation reactor, liquid methylcyclopentane entering the hydrogenation reactor reacts with gaseous hydrogen under the action of a hydrogenation catalyst to generate a target product methylcyclopentane, the target product methylcyclopentane is discharged from the bottom of the hydrogenation reactor, the hydrogen is prevented from being discharged, and the production safety can be effectively ensured on the basis of obtaining the target product.
2. The bottom discharge port of the rectifying tower is connected with the feed inlet of the cyclohexene reactor through a circulating pipeline, a circulating pump is arranged on the circulating pipeline, the bottom of the rectifying tower is a mixture containing cyclohexene and a molecular sieve catalyst, and the mixture is injected into the cyclohexene reactor through the circulating pipeline to circularly generate methylcyclopentene, so that cyclohexene raw materials are fully utilized, and the cost of synthesizing methylcyclopentane by enterprises is effectively reduced.
3. The reflux pipe is provided with a reflux tank which is positioned at the upstream of the reflux pump and used for buffering, decelerating and collecting liquid-phase methylcyclopentene discharged by the condenser, so that the flow of the liquid-phase methylcyclopentene which flows back to the rectifying tower and is discharged to the hydrogenation reactor is stable, the separation precision of the rectifying tower and the feeding precision of the hydrogenation reactor are ensured, and the purity of the separated methylcyclopentene and the conversion rate of the hydrogenation reactor are further ensured.
4. According to the process for preparing the methylcyclopentane from the cyclohexene, the cyclohexene is subjected to isomerization reaction by using the molecular sieve catalyst to obtain the methylcyclopentene, and then the target product methylcyclopentane is synthesized by using the hydrogenation catalyst, so that the reaction route is simple, the catalyst is cheap and easy to obtain, and the cost for producing the methylcyclopentane by enterprises can be effectively reduced.
5. The preparation method of the invention utilizes cyclohexene to generate intermediate product methylcyclopentene, the reaction temperature is 100-160 ℃, the reaction pressure is 0.3-0.8MPa, and if the temperature is lower than 100 ℃, the reaction conversion rate is obviously reduced, even the reaction is not performed. If the temperature is higher than 160 ℃, the reaction will tend to double molecular self-polymerization of cyclohexene rather than molecular rearrangement. The molecular sieve catalyst is cheap and easy to obtain, the reaction condition is mild, the obtained mixture is discharged to a rectifying tower for reduced pressure distillation, the solid phase and the liquid phase are extremely easy to separate, unreacted cyclohexene in the liquid phase and intermediate product methylcyclopentene are easy to separate, and the high-purity methylcyclopentene intermediate product (the purity is more than or equal to 93%) can be obtained through separation, so that the purity of the downstream synthesis target product is ensured.
6. The preparation method of the invention utilizes the obtained methylcyclopentene to react with hydrogen under the action of a hydrogenation catalyst to obtain the target product methylcyclopentane, the reaction temperature is 100-180 ℃, the reaction pressure is 1-2MPa, and if the temperature is lower than 100 ℃, the reaction conversion rate is obviously reduced or even not reacted. If the temperature is higher than 180 ℃, the reaction tends to open-chain hydrogenation reaction of methylcyclopentene, and finally methylpentane is generated, and the methylpentane is not generated through in-loop hydrogenation. The hydrogenation catalyst is cheap and easy to obtain, the reaction condition is mild, and the product obtained by the reaction is directly discharged from the bottom of the hydrogenation reactor and is easy to separate. The three wastes are not generated in the whole reaction process, unreacted raw materials or intermediate products can be recycled for reaction, and the overall conversion rate is high.
The applicant tests prove that the conversion rate of the intermediate product (methylcyclopentene) prepared by cyclohexene is 10%, the conversion rate of the intermediate product (methylcyclopentene) prepared by methylcyclopentane can reach 100%, and the purity of the obtained methylcyclopentane reaches more than 95%.
Further description is provided below with reference to the drawings and detailed description.
Drawings
FIG. 1 is a schematic diagram of the structure of the present invention;
in the drawing, 1 is a cyclohexene reactor, 2 is a rectifying tower, 3 is a hydrogenation reactor, 4 is a stirrer, 5 is a discharge pipe, 6 is a condenser, 7 is a return pipe, 8 is a return pump, 9 is a feed pipe, 10 is a circulation pipeline, 11 is a circulation pump, 12 is a return tank, a is a first valve, b is a second valve, c is a third valve, and d is a fourth valve.
Detailed Description
In the invention, equipment and parts without specific structures or models are usually selected from equipment or parts conventional in the chemical industry, and specific connection modes are not marked, which are usually conventional in the chemical industry or suggested by manufacturers.
Example 1
Referring to fig. 1, the device for preparing methylcyclopentane from cyclohexene comprises a cyclohexene reactor 1, a rectifying tower 2 and a hydrogenation reactor 3, wherein the number of the cyclohexene reactors is multiple, usually in parallel connection, the number of the rectifying towers can be multiple, the rectifying towers can be connected in parallel and/or in series connection, and the number of the hydrogenation reactors can also be multiple, usually in parallel connection, according to actual requirements. The cyclohexene reactor 1 is provided with a stirrer 4, and a feed inlet of the cyclohexene reactor 1 is used for being connected with a cyclohexene source, and in the embodiment, the feed inlet of the cyclohexene reactor is arranged at the middle lower part of the side wall of the reactor. The discharge port of the cyclohexene reactor 1 is connected with the rectifying tower 2 through a discharge pipe 5, and a first valve a is arranged on the discharge pipe 5, in this embodiment, the discharge port of the cyclohexene reactor is arranged at the middle upper part of the side wall of the reactor, so that the loss of the molecular sieve catalyst can be reduced, and the reaction can be fully performed. The top discharge port of the rectifying tower 2 is connected with the reflux port of the rectifying tower 2 through a condenser 6 and a reflux pipe 7, a reflux pump 8 is arranged on the reflux pipe 7, a second valve b is arranged on the reflux pipe 7 and positioned at the downstream of the reflux pump 8, a reflux tank 12 is arranged on the reflux pipe 7 for stabilizing the liquid intermediate product obtained by separation, the reflux tank is positioned at the upstream of the reflux pump 8, the bottom discharge port of the rectifying tower 2 is connected with the feed port of the cyclohexene reactor 1 through a circulating pipeline 10 for fully utilizing unreacted cyclohexene raw material, a circulating pump 11 is arranged on the circulating pipeline 10, a fourth valve d is arranged on the circulating pipeline 10 and positioned at the downstream of the circulating pump 11. The liquid phase feed inlet of the hydrogenation reactor 3 is connected with the return pipe 7 through the feed pipe 9, and is positioned between the return pump 8 and the second valve b, and the feed pipe 9 is provided with a third valve c. The gas phase feed inlet of the hydrogenation reactor 3 is positioned at the top of the hydrogenation reactor 3 and is used for being connected with a hydrogen source, and the discharge outlet of the hydrogenation reactor 3 is positioned at the bottom of the hydrogenation reactor 3.
Example 2
The apparatus of example 1 was used to prepare methylcyclopentane, comprising the steps of:
1) Adding cyclohexene (cyclohexene purity 99% wt) and molecular sieve catalyst (controlled volume concentration 0.25) into cyclohexene reactor, wherein the internal empty volume of cyclohexene reactor is 200m 3 Controlling the reaction temperature to be 110-112 ℃, the pressure to be 0.4-0.42MPa, and the cyclohexene feeding flow to be 100-105m 3 And (h) carrying out molecular rearrangement on cyclohexene to obtain a mixed material containing a molecular sieve catalyst, cyclohexene and methylcyclopentene;
2) Discharging the mixed material obtained in the step 1) to a rectifying tower, controlling the temperature of the top of the rectifying tower to be 35-37 ℃, controlling the temperature of a tower kettle to be 60-63 ℃, controlling the opening of a second valve and the opening of a third valve, separating to obtain methylcyclopentene, condensing the methylcyclopentene into a liquid state through a condenser, then entering a buffer tank, buffering, decelerating and collecting, refluxing part of the liquid methylcyclopentene to the rectifying tower under the driving of a reflux pump, and feeding part of the liquid methylcyclopentene into a hydrogenation reactor through a feed pipe, wherein the flow rate is 9-9.5m 3 And/h, making the reflux ratio of the rectifying tower be 10;
3) Hydrogenation is carried out in a hydrogenation reactor through a gas phase feed inlet, the purity of hydrogen is more than or equal to 99.9%, and the flow is 2000Nm 3 And/h. Methyl cyclopentene reacts with hydrogen under the action of hydrogenation catalyst (Ni) to obtain methyl cyclopentane, which is discharged from the bottom of the hydrogenation reactor with the flow of 9.6-10m 3 And/h, the reaction temperature is 100-105 ℃, and the pressure is 1-1.2MPa.
The applicant verifies that the conversion rate of cyclohexene preparation intermediate product (methylcyclopentene) is 9%, the conversion rate of methylcyclopentane is 100%, and the purity of the obtained methylcyclopentane is 95-95.5%.
Example 3
The apparatus of example 1 was used to prepare methylcyclopentane, comprising the steps of:
1) Adding cyclohexene (cyclohexene purity 99% wt) and molecular sieve catalyst (controlled volume concentration 0.35) into cyclohexene reactor, wherein the internal empty volume of cyclohexene reactor is 200m 3 Controlling the reaction temperature to be 130-132 ℃, the pressure to be 0.58-0.6MPa, and the cyclohexene feeding flow to be 180-183m 3 And (h) carrying out molecular rearrangement on cyclohexene to obtain a mixed material containing a molecular sieve catalyst, cyclohexene and methylcyclopentene;
2) Discharging the mixed material obtained in the step 1) to a rectifying tower, controlling the temperature of the top of the rectifying tower to be 53-55 ℃, controlling the temperature of a tower kettle to be 79-81 ℃, controlling the opening of a second valve and the opening of a third valve, separating to obtain methylcyclopentene, condensing the methylcyclopentene into a liquid state through a condenser, then entering a buffer tank, buffering, decelerating and collecting, refluxing part of the liquid methylcyclopentene to the rectifying tower under the driving of a reflux pump, and feeding part of the liquid methylcyclopentene into a hydrogenation reactor through a feed pipe, wherein the flow rate is 18-18.2m 3 And/h, enabling the reflux ratio of the rectifying tower to be 20;
3) Hydrogenation is carried out in a hydrogenation reactor through a gas phase feed inlet, the purity of hydrogen is more than or equal to 99.9%, and the flow is 5000Nm 3 And/h. Methyl cyclopentene reacts with hydrogen under the action of hydrogenation catalyst (Ni) to obtain methyl cyclopentane, which is discharged from the bottom of the hydrogenation reactor with the flow of 19.2-19.6m 3 And/h, the reaction temperature is 175-180 ℃ and the pressure is 1.8-2MPa.
The applicant verifies that the conversion rate of cyclohexene preparation intermediate (methylcyclopentene) is 9.7%, the conversion rate of methylcyclopentane is 100%, and the purity of the obtained methylcyclopentane is 95-95.3%.
Claims (8)
1. The device for preparing methylcyclopentane from cyclohexene is characterized in that: comprises at least one cyclohexene reactor (1), at least one rectifying tower (2) and at least one hydrogenation reactor (3),
the stirrer (4) is arranged in the cyclohexene reactor (1), the feed inlet of the cyclohexene reactor (1) is connected with a cyclohexene source, the discharge outlet of the cyclohexene reactor (1) is connected with the rectifying tower (2) through a discharge pipe (5), a first valve (a) is arranged on the discharge pipe (5), the bottom discharge outlet of the rectifying tower (2) is connected with the feed inlet of the cyclohexene reactor (1) through a circulating pipeline (10), a circulating pump (11) is arranged on the circulating pipeline (10),
the top discharge port of the rectifying tower (2) is connected with the reflux port of the rectifying tower (2) through a condenser (6) and a reflux pipe (7), the reflux pipe (7) is provided with a reflux pump (8), the reflux pipe (7) is provided with a second valve (b) and positioned at the downstream of the reflux pump (8), the reflux pipe (7) is provided with a reflux tank (12) positioned at the upstream of the reflux pump (8),
the liquid phase feed inlet of hydrogenation reactor (3) is continuous with back flow (7) through inlet pipe (9), is located between reflux pump (8) and second valve (b), sets up third valve (c) on inlet pipe (9), the gaseous phase feed inlet of hydrogenation reactor (3) is located the top of hydrogenation reactor (3) for link to each other with the hydrogen source, the bin outlet of hydrogenation reactor (3) is located the bottom of hydrogenation reactor (3).
2. The apparatus for preparing methylcyclopentane from cyclohexene as claimed in claim 1, wherein: the rectifying towers (2) are connected in parallel and/or in series.
3. The apparatus for preparing methylcyclopentane from cyclohexene as claimed in claim 1, wherein: a fourth valve (d) is arranged on the circulating pipeline (10) and is positioned at the downstream of the circulating pump (11).
4. A process for the preparation of methylcyclopentane using the apparatus as claimed in any one of claims 1 to 3, comprising the steps of:
1) Cyclohexene and a molecular sieve catalyst are taken and reacted in a cyclohexene reactor to obtain a mixed material containing the molecular sieve catalyst, cyclohexene and methylcyclopentene, wherein the reaction temperature is 100-160 ℃, and the pressure is 0.3-0.8MPa;
2) Discharging the mixed material obtained in the step 1) to a rectifying tower, controlling the temperature of the top of the rectifying tower to be 35-55 ℃, controlling the temperature of the tower kettle to be 60-80 ℃, controlling the opening of a second valve and the opening of a third valve to enable the reflux ratio of the rectifying tower to be 10-20, and separating to obtain methylcyclopentene to enter a hydrogenation reactor through a feed pipe;
3) The methyl cyclopentene reacts with hydrogen under the action of a hydrogenation catalyst to obtain methyl cyclopentane, the methyl cyclopentane is discharged from the bottom of the hydrogenation reactor, the reaction temperature is 100-180 ℃, and the pressure is 1-2MPa.
5. The process of claim 4 wherein the molecular sieve catalyst in step 1) has a particle size of 1 to 5um, a molar Si/Al ratio of 20 to 40, and a loading factor of 0.25 to 0.4 in the reactor.
6. The method according to claim 4, wherein the reaction temperature in step 1) is 110 to 130℃and the pressure is 0.4 to 0.6MPa.
7. The method according to claim 4, wherein the top temperature of the rectifying tower in the step 2) is 40-50 ℃, the bottom temperature is 65-75 ℃, and the reflux ratio of the rectifying tower is 10-15.
8. The process of claim 4, wherein the hydrogenation catalyst in step 3) is Ni, the molar ratio of hydrogen to methylcyclopentene is 1-2, the reaction temperature is 120-160 ℃, and the pressure is 1.2-1.8MPa.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110559749.XA CN113248341B (en) | 2021-05-21 | 2021-05-21 | Device and process for preparing methylcyclopentane from cyclohexene |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110559749.XA CN113248341B (en) | 2021-05-21 | 2021-05-21 | Device and process for preparing methylcyclopentane from cyclohexene |
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| Publication Number | Publication Date |
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| CN113248341A CN113248341A (en) | 2021-08-13 |
| CN113248341B true CN113248341B (en) | 2023-11-24 |
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| CN202110559749.XA Active CN113248341B (en) | 2021-05-21 | 2021-05-21 | Device and process for preparing methylcyclopentane from cyclohexene |
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