CN115974639B - Method for coproducing methylcyclopentane by cracking carbon nine hydrogenation device and pentane device - Google Patents
Method for coproducing methylcyclopentane by cracking carbon nine hydrogenation device and pentane device Download PDFInfo
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Abstract
The invention provides a method for coproducing methylcyclopentane by a pyrolysis carbon nine hydrogenation device and a pentane device, and relates to the field of methylcyclopentane preparation. The method comprises the following steps: (1) Sending the pyrolysis carbon nine into a colloid removal tower, and obtaining a pyrolysis carbon nine light component containing methyl cyclopentadiene at the tower top; (2) Hydrogenating the cracking carbon nine light component containing methyl cyclopentadiene through a cracking carbon nine first-stage hydrogenation reactor and a cracking carbon nine second-stage hydrogenation reactor to obtain a hydrogenated carbon nine component; (3) Stripping the hydrogenated carbon nine component by a stripping tower, and obtaining crude naphthenic oil at the top of the stripping tower; (4) Mixing crude naphthenic oil with the carbon five component, and then sending the mixture into a carbon five hydrofining reactor for hydrofining to obtain a saturated component; (5) Separating saturated components by a light component removing tower, an isopentane tower, a n-pentane tower, a cyclopentane tower and a methylcyclopentane tower, and obtaining methylcyclopentane from the top of the methylcyclopentane tower. The method is suitable for large-scale production, and the purity of the methylcyclopentane reaches more than 95%.
Description
Technical Field
The invention relates to the technical field of methylcyclopentane preparation, in particular to a method for coproducing methylcyclopentane by a pyrolysis carbon nine hydrogenation device and a pentane device.
Background
Methyl cyclopentane is a component of the naphthene in petroleum, is commonly used as a chemical solvent and chromatographic analysis standard substance, is also an important chemical intermediate, is used for organic synthesis, and can be used as an azeotropic distillation agent and an extraction agent.
At present, three main routes are available for producing methylcyclopentane, one is separated from solvent oil, the second is obtained by hydrofining methylcyclopentadiene, and the third is obtained by catalytic isomerization of cyclohexane. Wherein, the methyl cyclopentane is separated from the solvent oil mainly by common rectification, molecular sieve adsorption, extractive rectification, azeotropic rectification and other methods. Because the boiling points of normal hexane and methylcyclopentane are close, common rectification can only obtain industrial-grade methylcyclopentane with mass fraction below 90%; the molecular sieve adsorption can obtain methyl cyclopentane with higher purity, but the molecular sieve adsorption is easy to saturate and difficult to regenerate, so that the industrial production cost is higher; the extraction rectification is a better method for separating N-hexane and methylcyclopentane, the common extracting agents for the extraction rectification comprise dimethyl phthalate and N-methylpyrrolidone, the dimethyl phthalate and the N-methylpyrrolidone are respectively adopted as extracting agents in the patent CN1765857A and the patent CN103664446A, the N-hexane and the methylcyclopentane are separated, the purity of the methylcyclopentane extracted from the tower top is more than or equal to 84wt% and more than or equal to 90.8wt%, and the high-purity methylcyclopentane can be produced in the patent CN107935807B, but the extracting solvent has complex components, more theoretical plate numbers are needed, and the energy consumption is higher; the common entrainer for azeotropic distillation is methanol, but the process is longer, the investment of equipment and sites is large, and the energy consumption is high. For the second method, since the methylcyclopentadiene is similar to cyclopentadiene, the methylcyclopentadiene has special chemical property and inflammability and explosiveness, strict safety measures are required to be adopted when the methylcyclopentadiene is used, the production cost is high, the loss is large, the methylcyclopentadiene is directly hydrogenated to produce the methylcyclopentane, and the hydrogenation catalyst has short service life and high cost. In the third method, the cyclohexane catalytic isomerization proposed in the patent CN105439791A is used for producing methyl cyclopentane, and the cyclohexane conversion rate is low and the economy is poor.
Therefore, the research and development of the method for co-producing industrial methyl cyclopentane by adopting cheap raw materials and efficient process has more industrial application value.
Disclosure of Invention
The invention aims to overcome the defects of the separation method for preparing methylcyclopentane and the direct hydrogenation method for preparing methylcyclopentane by using methylcyclopentadiene in the prior art, and provides a method for co-producing methylcyclopentane by taking pyrolysis carbon nine and carbon five components as raw materials, namely a method for producing methylcyclopentane by combining a pyrolysis carbon nine hydrogenation device with a pentane device.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
a method for cracking a carbon nine hydrogenation unit and a pentane unit to co-produce methylcyclopentane, comprising:
(1) Sending the pyrolysis carbon nine from the ethylene device into a degelation tower, and partially decomposing methyl dicyclopentadiene and dimethyl dicyclopentadiene in the pyrolysis carbon nine in a degelation tower to obtain pyrolysis carbon nine light components containing methyl cyclopentadiene at the tower top;
(2) Hydrogenating the cracking carbon nine light component containing methyl cyclopentadiene through a cracking carbon nine first-stage hydrogenation reactor and a cracking carbon nine second-stage hydrogenation reactor to obtain a hydrogenated carbon nine component;
(3) Stripping the hydrogenated carbon nine component by a stripping tower, and obtaining crude naphthenic oil at the top of the stripping tower;
(4) Mixing crude naphthenic oil with the carbon five component from the pentane device, and then sending the mixture into a carbon five hydrofining reactor for hydrofining to obtain a saturated component;
(5) Separating saturated components by a light component removing tower, an isopentane tower, a n-pentane tower, a cyclopentane tower and a methylcyclopentane tower, and obtaining methylcyclopentane from the top of the methylcyclopentane tower.
Further, in the step (1), the pressure at the top of the degummed mass tower is minus 85 to minus 75 kPa, the temperature of a tower kettle is 180 to 200 ℃, and the yield of the nine light components of the cracking carbon containing the methylcyclopentadiene at the top of the tower is 85 to 90wt%.
Further, in the step (1), the total content of the methylcyclopentadiene in the pyrolysis carbon nine light components containing the methylcyclopentadiene is 2-8wt%.
Further, in the step (2), the reaction temperature of the pyrolysis carbon nine-stage hydrogenation reactor is 40-110 ℃, the reaction pressure is 3.0-4.5 MPa, and the space velocity of fresh materials is 0.4-0.8 h -1 Hydrogen oil volume ratio is 800-1200: 1.
further, in the step (2), the reaction temperature of the pyrolysis carbon nine-two-stage hydrogenation reactor is 230-310 ℃, the reaction pressure is 2.8-4.3 MPa, and the space velocity of fresh materials is 0.4-1.0 h -1 Hydrogen oil volume ratio 600-1300: 1.
further, in (2) and (4), the catalyst added in the cracking carbon nine-stage hydrogenation reactor is a nickel-based hydrogenation catalyst, and the catalysts added in the cracking carbon nine-stage hydrogenation reactor and the carbon five hydrofining reactor are cobalt-molybdenum-nickel-based catalysts.
Further, in (3), the top pressure of the stripping tower is 0-100 kPa, and the top temperature is 50-80 ℃.
Further, in the step (4), the reaction temperature of the carbon five hydrofining reactor is 150-240 ℃, the reaction pressure is 2.0-3.0 MPa, and the space velocity of fresh materials is 0.4-0.8 h -1 Hydrogen oil volume ratio is 1000-2000: 1.
further, in (4), the bromine index of the saturated component is less than 10 mg Br/100g oil, and the total sulfur is less than 5 mug/mL.
Further, in the step (5), the top pressure of the light component removing tower is 1.0-1.2 MPa, and the top temperature is 82-88 ℃.
Further, in the step (5), the top pressure of the isopentane tower is 100-150 kPa, and the top temperature is 49-58 ℃.
Further, in the step (5), the top pressure of the n-pentane tower is 80-120 kPa, and the top temperature is 55-59 ℃.
Further, in the step (5), the top pressure of the cyclopentane tower is 20-150 kPa, and the top temperature is 55-80 ℃.
In the step (5), the top pressure of the methylcyclopentane tower is 0-100 kPa, and the top temperature is 70-95 ℃.
Further, in the step (1), the upper part of the feeding port of the degummed tower is a filler, the lower part of the feeding port is a tray, the stripping tower and the light component removing tower are plate towers, and the isopentane tower, the n-pentane tower, the cyclopentane tower and the methylcyclopentane tower are all filler towers.
The operating pressures are gauge pressures in the invention.
Compared with the prior art, the invention has the beneficial technical effects that:
1. the method of the invention not only overcomes the problem of high energy consumption in extraction and separation of methylcyclopentane, but also overcomes the defects of high cost and short service life of the catalyst in direct hydrogenation of methylcyclopentadiene for preparing methylcyclopentane, and simultaneously overcomes the problem of low catalytic isomerism purity of cyclohexane, thereby realizing the comprehensive utilization of pyrolysis carbon nine more efficiently and at low cost, and having great significance in producing methylcyclopentane.
2. The methyl cyclopentane product produced by the method has high purity, low sulfur content, flexible process operation and long catalyst service period.
Drawings
FIG. 1 is a flow chart of a method for co-producing methylcyclopentane from a pyrolysis carbon nine hydrogenation unit and a pentane unit in accordance with the present invention;
wherein: the catalyst comprises a 1-degummed tower, a 2-cracking carbon nine-section hydrogenation reactor, a 3-cracking carbon nine-section hydrogenation reactor, a 4-stripping tower, a 5-carbon five hydrofining reactor, a 6-light component removing tower, a 7-isopentane tower, an 8-n-pentane tower, a 9-cyclopentane tower and a 10-methylcyclopentane tower.
Description of the embodiments
The invention is described in further detail below with reference to the accompanying drawings. The following description is not intended to limit the scope of the invention.
As shown in figure 1, in the method for co-producing methylcyclopentane by using the pyrolysis carbon nine hydrogenation device and the pentane device, raw material pyrolysis carbon nine S1 firstly enters a colloid removal tower 1 for colloid removal operation, a tower top product is pyrolysis carbon nine light component S2 containing methylcyclopentadiene, and a tower bottom is colloid heavy component S3. The cracking carbon nine light component S2 containing methyl cyclopentadiene of the tower top product of the degelation tower 1 is hydrogenated by a cracking carbon nine first-stage hydrogenation reactor 2 and a cracking carbon nine second-stage hydrogenation reactor 3 to obtain a hydrogenated carbon nine component S4. The hydrogenated carbon nine component S4 enters a stripping tower 4, crude naphthenic oil S5 is obtained at the top of the stripping tower 4, and hydrogenated solvent oil S6 is obtained at the bottom of the stripping tower 4. The carbon five component S7 from the pentane device is mixed with the crude naphthenic oil S5 obtained from the top of the stripping tower 4 and then enters a carbon five hydrofining reactor 5 for hydrofining to obtain a saturated component S8. The saturated component S8 enters a light component removing tower 6, a carbon four light component S9 is arranged at the top of the light component removing tower 6, a tower bottom material S10 of the light component removing tower 6 enters an isopentane tower 7, isopentane S11 is obtained at the top of the isopentane tower 7, a tower bottom material S12 of the isopentane tower 7 enters a normal pentane tower 8, normal pentane S13 is arranged at the top of the normal pentane tower 8, a tower bottom material S14 of the normal pentane tower 8 enters a cyclopentane tower 9, cyclopentane S15 is obtained at the top of the cyclopentane tower 9, a tower bottom material S16 of the cyclopentane tower 9 enters a methylcyclopentane tower 10, methyl cyclopentane S17 is arranged at the top of the methylcyclopentane tower 10, and a tower bottom of the methylcyclopentane tower 10 is a heavy component S18.
The following examples further illustrate the invention. The percentages in the examples are mass percentages unless noted and the pressures are gauge pressures.
Example 1
And (3) enabling the pyrolysis carbon nine S1 to enter a degelation tower 1, and partially decomposing methyl dicyclopentadiene and dimethyl dicyclopentadiene in the pyrolysis carbon nine S1 in the degelation tower 1 to obtain a pyrolysis carbon nine light component S2 containing the methyl cyclopentadiene at the tower top. The tower top pressure of the degelation tower 1 is-84.5 kPa, the tower bottom temperature is 185.4 ℃, and the yield of the pyrolysis carbon nine light components S2 of the methyl cyclopentadiene at the tower top is 88%. Table 1 shows the composition of the methylcyclopentadiene-containing cleavage carbon nine light component S2 of the present example.
TABLE 1 composition of nine light components S2 containing methylcyclopentadiene
The cracking carbon nine light component S2 containing methyl cyclopentadiene passes through a cracking carbon nine one-stage hydrogenation reactor 2, the cracking carbon nine one-stage hydrogenation reaction temperature is 71 ℃, the reaction pressure is 3.8 MPa, and the space velocity of fresh materials is 0.75 h -1 Hydrogen oil volume ratio 850: 1, bromine number 32 g Br/100 g.
The materials from the cracking carbon nine-first-stage hydrogenation reactor 2 enter a cracking carbon nine-second-stage hydrogenation reactor 3 for hydrogenation, the reaction temperature of the cracking carbon nine-second-stage hydrogenation reactor 3 is 270 ℃, the reaction pressure is 3.4 MPa, and the space velocity of fresh materials is 0.85h -1 Hydrogen oil volume ratio 900:1, hydrogenation to obtain hydrogenated carbon nine component S4, bromine value 4.3 g Br/100g oil.
And (3) feeding the hydrogenated carbon nine component S4 into a stripping tower 4 for stripping, and obtaining crude naphthenic oil S5 at the top of the stripping tower 4. The pressure at the top of the stripping column 4 is 80 kPa and the temperature at the top of the stripping column is 68 ℃.
The crude naphthenic oil S5 and the carbon five component S7 from the pentane device are mixed and then fed into a carbon five hydrofining reactor 5 to obtain a saturated component S8. The reaction temperature of the carbon five hydrofining reactor 5 is 182.5 ℃, the reaction pressure is 2.40 MPa, and the space velocity of fresh materials is 0.54. 0.54 h -1 Hydrogen oil volume ratio 1800: 1.
the bromine index of the saturated component S8 is less than 10 mg Br/100g oil, and the total sulfur is 4.8 mug/mL.
The saturated component S8 enters a light component removing tower 6, and a carbon four light component S9 is obtained at the top of the tower. The pressure at the top of the light component removing column 6 is 1.09 MPa, and the temperature at the top of the column is 85.4 ℃.
And (3) feeding a tower bottom material S10 of the light component removing tower 6 into an isopentane tower 7, and obtaining isopentane S11 at the tower top. The pressure at the top of the isopentane column 7 was 120 kPa and the temperature at the top of the column was 51.5 ℃.
And (3) feeding the material S12 at the tower bottom of the isopentane tower 7 into the n-pentane tower 8, and obtaining n-pentane S13 at the tower top. The pressure at the top of the n-pentane column 8 was 105 kPa and the temperature at the top of the column was 57.5 ℃.
And (3) feeding the tower bottom material S14 of the n-pentane tower 8 into a cyclopentane tower 9, and obtaining cyclopentane S15 at the tower top. The column top pressure of the cyclopentane column 9 was 149 kPa and the column top temperature was 78.8 ℃.
And feeding the material S16 at the bottom of the cyclopentane tower 9 into the methylcyclopentane tower 10, and obtaining a methylcyclopentane S17 product with the purity of more than 95% at the top of the tower. The methylcyclopentane column 10 had a head pressure of 50 kPa and a head temperature of 85 ℃.
Example two
The same procedure was used as in example one, except that the following conditions were changed:
the tower top pressure of the colloid removing tower 1 is-75 kPa, and the tower bottom temperature is 200 ℃.
Cracking carbon nine-stage hydrogenation reactor 2 reaction temperature 40 ℃, reaction pressure 3.0 MPa and fresh material space velocity 0.4 h -1 Hydrogen oil volume ratio 800: 1.
cracking carbon nine-two-stage hydrogenation reactor 3 reaction temperature 230 ℃, reaction pressure 2.8 MPa and fresh material space velocity 0.4 h -1 Hydrogen oil volume ratio 600:1.
the pressure at the top of the stripping column 4 is 0 kPa and the temperature at the top of the stripping column is 50 ℃.
The reaction temperature of the carbon five hydrofining reactor 5 is 150 ℃, the reaction pressure is 2.0 MPa, and the space velocity of fresh materials is 0.4 h -1 Hydrogen oil volume ratio 1000:1.
the bromine index of the saturated component S8 is less than 10 mg Br/100g oil, and the total sulfur is 3.8 mug/mL.
The pressure at the top of the light component removing tower 6 is 1.0 MPa, and the temperature at the top of the tower is 82 ℃.
The pressure at the top of the isopentane column 7 was 100 kPa and the temperature at the top was 49 ℃.
The pressure at the top of the n-pentane column 8 was 80 kPa and the temperature at the top was 55 ℃.
The column top pressure of the cyclopentane column 9 was 20 kPa and the column top temperature was 55 ℃.
The pressure at the top of the methylcyclopentane column 10 was 0 kPa, and the temperature at the top was 70 ℃.
Example III
This example uses the same method as example one, except that:
the tower top pressure of the colloid removing tower 1 is-85 kPa, and the tower bottom temperature is 180 ℃.
Cracking carbon nine-stage hydrogenation reactor 2 reaction temperature 110 ℃, reaction pressure 4.5 MPa and fresh material space velocity 0.8h -1 Hydrogen oil volume ratio 1200：1。
Cracking carbon nine-two-stage hydrogenation reactor 3 reaction temperature 310 ℃, reaction pressure 4.3MPa and fresh material space velocity 1 h -1 Hydrogen oil volume ratio 1300:1.
the pressure at the top of the stripping column 4 is 100 kPa, and the temperature at the top of the stripping column is 80 ℃.
The reaction temperature of the carbon five hydrofining reactor 5 is 240 ℃, the reaction pressure is 3.0 MPa, and the space velocity of fresh materials is 0.8h -1 Hydrogen oil volume ratio 2000:1.
the bromine index of the saturated component S8 is less than 10 mg Br/100g oil, and the total sulfur is 3.2 mug/mL.
The pressure at the top of the light component removing tower 6 is 1.2 MPa, and the temperature at the top of the tower is 88 ℃.
The pressure at the top of the isopentane column 7 was 150 kPa and the temperature at the top of the column was 58 ℃.
The pressure at the top of the n-pentane column 8 was 120 kPa and the temperature at the top was 59 ℃.
The column top pressure of the cyclopentane column 9 was 150 kPa and the column top temperature was 80 ℃.
The pressure at the top of the methylcyclopentane column 10 was 100 kPa, and the temperature at the top was 95 ℃.
The purity of the methylcyclopentane obtained by the method disclosed by the invention reaches more than 95%, and the yield reaches more than 95%.
Claims (1)
1. A method for co-producing methylcyclopentane by cracking a carbon nine hydrogenation device and a pentane device, comprising the steps of:
(1) Feeding the pyrolysis carbon nine raw material from the ethylene device into a degelation tower, and partially decomposing methyl dicyclopentadiene and dimethyl dicyclopentadiene in the pyrolysis carbon nine in a degelation tower to obtain pyrolysis carbon nine light components containing the methyl cyclopentadiene at the tower top; the tower top pressure of the degumming tower is-85 to-75 KPa, the tower bottom temperature is 180-200 ℃, and the yield of the cracked carbon nine light components at the tower top is 85-90 wt%; the total content of the methylcyclopentadiene in the pyrolysis carbon nine light components containing the methylcyclopentadiene is 2-8%;
(2) Hydrogenating the cracking carbon nine light component containing methyl cyclopentadiene through a cracking carbon nine first-stage hydrogenation reactor and a cracking carbon nine second-stage hydrogenation reactor to obtain a hydrogenated carbon nine component; cracking carbon nine one sectionThe catalyst added in the hydrogenation reactor is nickel hydrogenation catalyst, the reaction temperature of the pyrolysis carbon nine-stage hydrogenation reactor is 40-110 ℃, the reaction pressure is 3.0-4.5 MPa, and the space velocity of fresh materials is 0.4-0.8 h -1 Hydrogen oil volume ratio is 800-1200; the catalyst added in the cracking carbon nine-two-stage hydrogenation reactor is cobalt-molybdenum-nickel catalyst, the reaction temperature of the cracking carbon nine-two-stage hydrogenation reactor is 230-310 ℃, the reaction pressure is 2.8-4.3 MPa, and the space velocity of fresh materials is 0.4-1.0 h -1 Hydrogen oil volume ratio 600-1300
(3) Stripping the hydrogenated carbon nine component by a stripping tower, and obtaining crude naphthenic oil at the top of the stripping tower; the top pressure of the stripping tower is 0-100 KPa, and the top temperature of the stripping tower is 50-80 ℃;
(4) Mixing crude naphthenic oil with the carbon five component from the pentane device, and then sending the mixture into a carbon five hydrofining reactor for hydrofining to obtain a saturated component; the catalyst added in the carbon five hydrofining reactor is cobalt-molybdenum-nickel catalyst, the reaction temperature of the carbon five hydrofining reactor is 150-240 ℃, the reaction pressure is 2.0-3.0 MPa, and the space velocity of fresh materials is 0.4-0.8 h -1 The volume ratio of hydrogen to oil is 1000-2000, the bromine index of saturated component is less than 10 mg Br/100g oil, the total sulfur is less than 5 mug/mL,
(5) Separating saturated components by a light component removing tower, an isopentane tower, a n-pentane tower, a cyclopentane tower and a methylcyclopentane tower, and obtaining methylcyclopentane from the top of the methylcyclopentane tower; the pressure at the top of the light component tower is 1.0-1.2 MPa, and the temperature at the top of the tower is 82-88 ℃; the top pressure of the isopentane tower is 100-150 KPa, and the top temperature of the isopentane tower is 49-58 ℃; the tower top pressure of the n-pentane tower is 80-120 KPa, and the tower top temperature is 56-59 ℃; the top pressure of the cyclopentane tower is 20-150 KPa, and the top temperature is 55-80 ℃; the top pressure of the methylcyclopentane tower is 0-100 kPa, and the top temperature is 70-95 ℃.
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| CN1919809A (en) * | 2006-06-15 | 2007-02-28 | 天津天大天海化工新技术有限公司 | Energy-saving technique for producing high-purity pentane and pentane foaming agent |
| CN102399121A (en) * | 2010-09-17 | 2012-04-04 | 中国石油化工股份有限公司 | Preparation method of cyclopentane and methylcyclopentane |
| ITMI20112271A1 (en) * | 2011-12-15 | 2013-06-16 | Sime Srl | SEPARATION OF HYDROCARBURIC FAMILIES OR INDIVIDUAL COMPONENTS VIA CONSECUTIVE EXTRACTIVE DISTILLATIONS CARRIED OUT IN ONE COLUMN. |
| TWI568708B (en) * | 2015-09-16 | 2017-02-01 | Cpc Corp | A method for co-producing dicyclopentadiene and methyl cyclopentane |
| CN207062168U (en) * | 2017-07-26 | 2018-03-02 | 抚顺伊科思新材料有限公司 | Thick light dydrocarbon produces high alkene light dydrocarbon, pentane, isopentane and pentamethylene equipment |
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| CN114436752A (en) * | 2020-10-16 | 2022-05-06 | 中国石油化工股份有限公司 | Method for improving comprehensive utilization rate of ethylene cracking C9 fraction |
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| CN114436751A (en) * | 2020-10-16 | 2022-05-06 | 中国石油化工股份有限公司 | Preparation method of methylcyclopentene |
| CN114436738A (en) * | 2020-10-16 | 2022-05-06 | 中国石油化工股份有限公司 | Preparation method of high-purity methylcyclopentene |
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