CN112573989A - Preparation method and preparation device of halogen-free cyclohexane - Google Patents
Preparation method and preparation device of halogen-free cyclohexane Download PDFInfo
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- CN112573989A CN112573989A CN201910937560.2A CN201910937560A CN112573989A CN 112573989 A CN112573989 A CN 112573989A CN 201910937560 A CN201910937560 A CN 201910937560A CN 112573989 A CN112573989 A CN 112573989A
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- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
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Abstract
The invention relates to a preparation method and a preparation device of cyclohexane, comprising the following steps: adding raw materials and a catalyst into a reactor, and heating the reactor; continuously or intermittently adding catalyst active components into the reactor for catalytic reaction to obtain a reaction mixture; the reaction mixture enters the elevated tank through a pipeline, the reaction mixture is layered in the elevated tank, the upper layer material flows out through an overflow port and a product pipeline to obtain cyclohexane without halogen, and the lower layer material enters the reactor through a bent pipeline to continue catalytic reaction. By utilizing the preparation method of the invention, the selectivity of the prepared cyclohexane is not lower than 99 percent, and the product does not contain halogen.
Description
Technical Field
The invention belongs to the technical field of comprehensive utilization of refining and chemical byproducts, and particularly relates to a preparation method and a preparation device of cyclohexane without halogen.
Background
Cyclohexane (CH) is the main raw material for producing cyclohexanol and cyclohexanone, and is also used for producing adipic acid and caprolactam, which are main raw materials for producing polyamide and nylon. Furthermore, cyclohexane is also used as an industrial solvent. The global demand for cyclohexane increased by 3% on average from 2005 to 2010.
Cyclohexane was originally obtained by direct separation by distillation of crude oil, but its purity was only around 85%. Then, people separate crude gasoline (containing about 5-15% of cyclohexane) to obtain 65.6-85.3 ℃ fractions (mainly containing cyclohexane and methylcyclopentane), isomerize the methylcyclopentane into cyclohexane at 80 ℃ by using anhydrous aluminum trichloride as a catalyst, and obtain the cyclohexane with the purity of more than 95% after a series of operations such as distillation, pyrolysis (paraffin removal), solvent treatment (aromatic hydrocarbon and olefin removal) and the like of the isomerized products. The Henbell oil company and Philips oil company in the United states report a method for isomerizing methyl cyclopentane into cyclohexane after a series of steps of reforming, rectifying, hydrogenating and isomerizing light distillate oil in oil fraction, and cyclohexane with purity of 99% can be obtained by using the method. With the development of polyamide production, the demand of cyclohexane is rapidly increased, and the method for obtaining cyclohexane cannot meet the requirements on quantity and quality, so that the method for producing cyclohexane by benzene hydrogenation is rapidly developed, wherein the method generally uses nickel as a catalyst, and benzene is hydrogenated to produce cyclohexane at 150-250 ℃ and 23-53 atmospheric pressure. The yield of the cyclohexane produced by the method is close to 100 percent, and the purity of the product is high, so the method is the main method for producing the cyclohexane at present. However, the price of benzene has been high in recent years, which increases the cost of producing cyclohexane by hydrogenation of benzene.
The ethylene preparation by steam cracking and the byproduct cracked gasoline are subjected to two-stage hydrogenation and aromatic extraction to produce a large amount of raffinate oil, wherein C is contained in the raffinate oil6The alkane accounts for more than 40 percent, the raffinate oil is mainly used for producing solvent oil at present, and part of raffinate oil is returned to the cracking furnace to be used as cracking raw materials, so that the added value utilization is not basically improved. Separating C from raffinate6And the fraction is distilled, methylcyclopentane is isomerized into cyclohexane, and the cyclohexane with higher purity is obtained by rectification, so that the utilization value of raffinate oil is greatly improved. In the prior art, although a dechlorination unit is arranged after separation in the process of producing cyclohexane, an adsorbent of the dechlorination unit is extremely easy to adsorb and saturate, the adsorption is irreversible and can not be regenerated, the adsorbent needs to be frequently replaced, the production cost is increased, and the environmental protection pressure is increased. If the adsorbent is saturated, chlorine-containing products can corrode equipment after passing through the dechlorination unit, the service cycle of the device is shortened, and great potential safety hazards exist.
Disclosure of Invention
The invention aims to solve the technical problems of high cost and halogen-containing products in the prior art of adopting a benzene hydrogenation technology for producing cyclohexane, and provides a method and a device for producing halogen-free cyclohexane by using C6 raffinate oil or methyl cyclopentane as a raw material.
In order to solve the above technical problems, a first aspect of the present invention provides an apparatus for preparing cyclohexane containing no halogen, comprising:
the reactor 3 is provided with a catalyst pipeline 5, a raw material pipeline 6, a stirring motor 4 and a heating steam pipeline 2, and the heating steam pipeline 2 is positioned on the outer wall of the reactor 3.
The elevated tank 11 is connected with the reactor 3 through a pipeline, the upper part of the elevated tank 11 is provided with an overflow port and a product pipeline 10, the overflow port is connected with the product pipeline 10, and the bottom of the elevated tank 11 is connected with the reactor 3 through a bent pipeline 8.
According to some embodiments of the invention, the curved line 8 is a U-shaped pipe, a polygonal line pipe or a wavy line pipe, the vertical height of the top and bottom of the curved line 8 is h1, the vertical height of the product line 10 and the bottom of the curved line 8 is h2, h 2: h1 is 1.1 to 2.0, and more specific height ratios within this ratio range are 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, and the like.
According to some embodiments of the present invention, after the mixture is layered in head tank 11, the interface between the two layers has a vertical height h from the bottom of curved pipeline 8.
According to some embodiments of the invention, a static mixer 14 is provided on the curved line 8.
According to some embodiments of the invention, a branch line is provided in the line between the head tank 11 and the reactor 3, connected upstream of the static mixer 14, and forms a material circulation with the reactor 3.
In the present invention, upstream and downstream of the static mixer 14 means that the pipeline through which the material flows into one end of the static mixer 14 is upstream, and the pipeline through which the material flows out of one end of the static mixer 14 is downstream.
According to some embodiments of the present invention, the material of the reactor 3 is carbon steel (lining polytetrafluoroethylene), hastelloy, 316L stainless steel, and the reactor 3 made of these materials has good corrosion resistance.
In the present invention, a reaction raw material and a catalyst are reacted in a reactor 3 to produce a mixture, and a part of the mixture is pumped out by a circulation pump 1 provided in a pipeline and then circulated to the reactor 3 through a branch pipeline and a static mixer 14; a portion of the mixture is delivered to head tank 11 via rotameter 12. The mixture is layered in the elevated tank 11, and since the density of the catalyst is higher than that of the product (the density of the catalyst is about 2 times of that of the product), the lower layer catalyst is mixed with the circulating material in the static mixer 14 through the bent pipeline 8 and enters the reactor 3, and the upper layer product overflows from the product pipeline 10 and enters the subsequent process.
In order to solve the above technical problems, a second aspect of the present invention provides a method for producing halogen-free cyclohexane, comprising the steps of:
(1) adding raw materials and a catalyst into a reactor, and heating the reactor;
(2) continuously or intermittently adding catalyst active components into the reactor for catalytic reaction to obtain a reaction mixture;
(3) the reaction mixture enters the elevated tank 11 through a pipeline, the reaction mixture is layered in the elevated tank 11, the upper layer material flows out through an overflow port and a product pipeline 10 to obtain cyclohexane without halogen, and the lower layer material catalyst enters the reactor 3 through a bent pipeline 8 to continue catalytic reaction.
According to some embodiments of the present invention, the raw material for producing cyclohexane is raffinate oil or methylcyclopentane, wherein the raffinate oil is a large amount of oil substances produced by two-stage hydrogenation and aromatic extraction of pyrolysis gasoline as a byproduct in the production of ethylene by steam cracking, C6 alkanes in the raffinate oil account for more than 40%, a C6 fraction, i.e., C6 raffinate oil, is separated from the raffinate oil, and then the halogen-free cyclohexane is prepared by using the method of the present invention.
According to some embodiments of the invention, in step (1), the catalyst is a liquid phase catalyst having a density of 0.8 to 1.4 g/ml, preferably 1.0 to 1.4 g/ml, such as, but not limited to, 1.0 g/ml, 1.1 g/ml, 1.2 g/ml, 1.3 g/ml, 1.4 g/ml, and the like.
According to some embodiments of the invention, in step (1), the catalyst comprises (R)1)3NHCl-xAlX3、[CnPy]-x AlCl3And [ Cnmin]-x AlX3One or more of (a) or (b),
R1is selected from C1-C6Alkyl, preferably selected from methyl, ethyl, isopropyl and n-propyl;
x is 0.5-10, preferably 0.5-5;
n is 1 to 6, preferably 1 to 4;
x is halogen, preferably selected from chlorine and bromine.
According to some embodiments of the invention, in step (1), the volume ratio of the feedstock to the catalyst is 1 to 10:1, preferably 1 to 6:1, within this ratio range, as more specific volume ratios are 1:1, 1.5:1, 2:1, 2.5:1, 3:1, 3.5:1, 4:1, 4.5:1, 5:1, 5.5:1, 6:1, and so forth.
According to some embodiments of the present invention, in the step (1), the reaction temperature is 40 to 100 ℃, preferably 60 to 75 ℃, the reaction pressure is 0 to 2bar, preferably 0.1 to 0.8bar, and the rotation speed of the stirring motor is 0 to 200 rpm, preferably 100 to 200 rpm.
According to some embodiments of the present invention, in step (2), the catalyst active component is halogenated aluminum, specifically aluminum trichloride, aluminum tribromide, aluminum trifluoride, or the like.
According to some embodiments of the present invention, in the step (1), a nozzle is provided in the reactor, and the raw material and the catalyst are injected into the reactor through the nozzle; in the step (2), the active components of the catalyst are replenished through a replenishing tank connected with the reactor 3, a sieve cage is arranged in the replenishing tank, and a stirring device is arranged in the sieve cage.
According to some embodiments of the present invention, in the step (2), the aperture of the screen cage is 50 to 100 mesh, preferably 50 to 80 mesh, and as non-limiting specific point values in the aperture range, the aperture value of the screen cage may be 50 mesh, 55 mesh, 60 mesh, 65 mesh, 70 mesh, 75 mesh, 80 mesh.
According to some embodiments of the invention, in step (2), the mass of the catalytically active component is between 1% and 10%, preferably between 1% and 5% of the mass of the catalyst.
According to some embodiments of the invention, the nozzle is solid and the nozzle material is selected from any one of teflon, hastelloy and 316L stainless steel.
In the invention, the catalytic efficiency of the catalyst is indirectly judged by judging the cyclohexane content in the product, when the catalytic efficiency of the catalyst is low, the active component of the catalyst is added online in real time by using the device disclosed by the invention, and the process conditions of the invention are utilized to reach the equilibrium conversion rate of the raw material (C6 raffinate oil or methylcyclopentane) by controlling the stirring speed of the stirring device in the replenishment tank.
The preparation process of cyclohexane in the invention is as follows: c6 raffinate oil or methyl cyclopentane is dissolved in a solvent and enters a reactor 3 from a raw material pipeline 6 through a second nozzle 16, a stirring motor 4 is started, a catalyst enters the reactor 3 from a catalyst pipeline 5 through a third nozzle 17, a heating steam pipeline 2 is started to heat the reactor, a ball valve 13 is closed, a circulating pump 1 is started to establish circulation, after reaction is carried out for a certain time, the ball valve 13 is started, the flow of the material entering a head tank 11 is controlled through a flowmeter 12, the mixed material is layered in the head tank 11, when the liquid level of the head tank reaches an overflow port, the catalyst enters a static mixer 14 from a bent pipeline 8 and is fully mixed with the circulated material, the mixed material is sprayed into the reactor 3 through the nozzle, and a product enters a subsequent process from a product pipeline 10. After the reaction is carried out for a period of time, continuously or intermittently adding the active components of the catalyst into the sieve cage in the catalyst replenishing tank.
The invention has the beneficial effects that:
1. the catalyst and the catalyst active component can effectively catalyze the C6 component in the raffinate oil into cyclohexane, the conversion rate can reach more than 70 percent, and the selectivity can reach 99 percent, while the conversion rate of methyl cyclopentane adopting other types of catalysts does not exceed 30 percent, and the selectivity of cyclohexane does not exceed 50 percent.
2. According to the invention, by arranging the elevated tank and controlling the height difference between the bent pipeline at the bottom of the elevated tank and the product pipeline at the upper part, the mixture is layered, and the product does not contain halide ions, so that the environment is not polluted.
Drawings
FIG. 1 is a schematic diagram of a halide-free cyclohexane production plant of the present invention;
wherein the reference numerals are:
1-a circulating pump; 2-heating the steam pipeline; 3-a reactor; 4-a stirring motor; 5-catalyst line; 6-feed line; 7-a feed flow meter; 8-bending the pipeline; 9-a product flow meter; 10-a product line; 11-elevated tank; 12-a flow meter; 13-a ball valve; 14-a static mixer; 15-first nozzle, 16-second nozzle, 17-third nozzle.
Detailed Description
The invention is further illustrated by the following examples.
Example 1
A process for the production of cyclohexane comprising the steps of:
c6 raffinate oil enters the reactor 3 from the raw material pipeline 6 through the second nozzle 16, the stirring motor 4 is turned on, and the Catalyst (CH)3)3NHCl-3AlCl3The catalyst enters the reactor 3 from the catalyst pipeline 5 through the third nozzle 17, the heating steam pipeline 2 is opened to heat the reactor 3, the ball valve 13 is closed, the circulating pump 1 is started to establish circulation, after 24 hours of reaction, the ball valve 13 is started, the material flow entering the head tank 11 is controlled through the flow meter 12, the mixed material is layered in the head tank 11, after the liquid level of the head tank 11 reaches an overflow port, the catalyst enters the static mixer 14 from the bent pipeline 8 to be fully mixed with the circulated material, the mixed material is sprayed into the reactor 3 through the first nozzle 15, and the product enters the subsequent process from the product pipeline 10.
In this embodiment, h 2: h1 is 1.9, the feed flow meter 7 of the raw material pipeline is set to be 100 liters/h, the flow meter 12 is set to be 130 liters/h, the product flow meter 9 is set to be 100 liters/h, the stirring speed is 200 revolutions per minute, the feeding oil agent ratio is 2:1, the active components of the catalyst in the replenishing tank account for 1.67 percent of the mass of the catalyst, the reaction temperature is 75 ℃, and the reaction pressure is 0.8bar for continuous reaction for 24 hours, and the result is shown in table 1. The product is free of chloride ions.
Example 2
Example 2 differs from example 1 in that:
h 2: h1 is 1.5, the feed flow meter 7 of the raw material pipeline is set to 150 liters/h, the flow meter 12 is set to 180 liters/h, the product flow meter 9 is set to 150 liters/h, the stirring speed is 200 r/min, the feeding oil agent ratio is 3:1, the active components of the catalyst in the replenishing tank account for 1.67 percent of the mass of the catalyst, the reaction temperature is 70 ℃, the reaction pressure is 0.6bar, and the result of continuous reaction for 24 hours is shown in table 1. The product is free of chloride ions.
Example 3
Example 3 differs from example 1 in that:
the active component of the catalyst is AlBr3，
h 2: h1 is 1.7, the feed flow meter 7 of the raw material pipeline is set to be 80 liters/h, the flow meter 12 is set to be 110 liters/h, the product flow meter 9 is set to be 80 liters/h, the stirring speed is 100 r/min, the feeding oil agent ratio is 4:1, the active components of the catalyst in the replenishing tank account for 3.33 percent of the mass of the catalyst, the reaction temperature is 65 ℃, the reaction pressure is 0.6bar, and the result of continuous reaction for 24 hours is shown in table 1. The product contains no chlorine and bromine ions.
Example 4
Example 4 differs from example 1 in that:
h 2: h1 is 1.6, the feed flow meter 7 of the raw material pipeline is set to be 50 liters/h, the flow meter 12 is set to be 80 liters/h, the product flow meter 9 is set to be 50 liters/h, the stirring speed is 100 r/min, the feeding oil agent ratio is 5:1, the active components of the catalyst in the replenishing tank account for 3.33 percent of the mass of the catalyst, the reaction temperature is 75 ℃, the reaction pressure is 0.6bar, and the result of continuous reaction for 24 hours is shown in table 1. The product is free of chloride ions.
Example 5
Example 5 differs from example 1 in that:
h 2: h1 is 1.9, the feed flow meter 7 of the raw material pipeline is set to be 50 liters/hour, the flow meter 12 is set to be 80 liters/hour, the product flow meter 9 is set to be 50 liters/hour, the stirring speed is 150 revolutions per minute, the feeding oil agent ratio is 6:1, the active components of the catalyst in the replenishing tank account for 5 percent of the mass of the catalyst, the reaction temperature is 60 ℃, the reaction pressure is 0.5bar, and the result of continuous reaction for 24 hours is shown in table 1. The product is free of chloride ions.
Example 6
Example 6 differs from example 1 in that:
h 2: h1 is 1.9, the feed flowmeter 7 of the raw material pipeline is set to be 50 liters/h, the flowmeter 12 is set to be 80 liters/h, the product flowmeter 9 is set to be 50 liters/h, the stirring speed is 100 r/min, the feeding oil ratio is 1:1, the active components are not supplemented, the reaction temperature is 75 ℃, the reaction pressure is 0.6bar, and the result of continuous reaction for 24 hours is shown in table 1. The product is free of chloride ions.
Example 7
Example 7 differs from example 1 in that:
h 2: h1 is 1.9, the feed flow meter 7 of the raw material pipeline is set to be 50 liters/hour, the flow meter 12 is set to be 80 liters/hour, the product flow meter 9 is set to be 50 liters/hour, the stirring speed is 100 revolutions per minute, the feeding oil agent ratio is 2:1, the active components of the catalyst in the replenishing tank account for 1.67 percent of the mass of the catalyst, the reaction temperature is 75 ℃, the reaction pressure is 0.8bar, and the result of continuous reaction for 24 hours is shown in table 1. The product is free of chloride ions.
Example 8
This comparative example differs from example 7 in that the catalyst was nickel isooctanoate-triethylaluminum and the results are detailed in Table 1.
Example 9
This comparative example differs from example 7 in that the catalyst was selected from anhydrous AlCl3The specific results are detailed in table 1. The catalyst is difficult to recover due to strong corrosivity, and the post-treatment is complex.
Example 10
This comparative example differs from example 7 in the choice of [ BMIM ] as catalyst]Cl-AlCl3The specific results are detailed in table 1.
Example 11
This example differs from example 2 in that: h 2: h1 is 1.0, the chloride ion content in the product is 800 ppm.
Example 12
This example differs from example 2 in that: h 2: h1 is 0.8 and catalyst does not enter reactor 8.
Example 13
This example differs from example 7 in that: h 2: h1 is 2.0, the content of chloride ion in the product is 0.
Example 14
This example differs from example 7 in that: h 2: h 1-2.2, the product does not flow out through the overflow, but is recycled with the catalyst into the reactor 8.
TABLE 1
It should be noted that the above-mentioned embodiments are only for explaining the present invention, and do not set any limit to the present invention. The present invention has been described with reference to exemplary embodiments, but the words which have been used herein are words of description and illustration, rather than words of limitation. The invention can be modified, as prescribed, within the scope of the claims and without departing from the scope and spirit of the invention. Although the invention has been described herein with reference to particular means, materials and embodiments, the invention is not intended to be limited to the particulars disclosed herein, but rather extends to all other methods and applications having the same functionality.
Claims (10)
1. An apparatus for preparing halogen-free cyclohexane comprising:
a reactor (3);
the elevated tank (11) is connected with the reactor (3) through a pipeline, the upper part of the elevated tank (11) is provided with an overflow port and a product pipeline (10), the overflow port is connected with the product pipeline (10), and the bottom of the elevated tank (11) is connected with the reactor (3) through a bent pipeline (8).
2. The apparatus for preparing halogen-free cyclohexane according to claim 1, wherein the bending line (8) is a U-shaped pipe, a folded line pipe or a wavy line pipe, the vertical height of the top and bottom of the bending line (8) is h1, and the vertical height of the product line (10) and the bottom of the bending line (8) is h2, h 2: h1 is 1.1-2.0.
3. The apparatus for preparing halogen-free cyclohexane according to claim 1 or 2, characterized in that a static mixer (14) is provided on the bending line (8).
4. Process for the preparation of halogen-free cyclohexane, characterized in that it is carried out in an apparatus according to any one of claims 1 to 4, preferably comprising the following steps:
(1) adding raw materials and a catalyst into a reactor (3), and heating the reactor (3);
(2) continuously or intermittently adding catalyst active components into the reactor (3) for catalytic reaction to obtain a reaction mixture;
(3) the reaction mixture enters the elevated tank (11) through a pipeline, the reaction mixture is layered in the elevated tank (11), the upper layer material flows out through an overflow port and a product pipeline (10) to obtain cyclohexane without halogen, and the lower layer material enters the reactor (3) through a bent pipeline (8) for continuous catalytic reaction.
5. The process according to claim 4, wherein in the step (1), the raw material is C6 raffinate or methylcyclopentane, preferably C6 raffinate.
6. The process according to claim 4 or 5, wherein in the step (1), the catalyst is a liquid phase catalyst having a density of 0.8 to 1.4 g/ml, preferably 1.0 to 1.4 g/ml.
7. The production method according to any one of claims 4 to 6, wherein the catalyst comprises (R)1)3NHCl-xAlX3、[CnPy]-x AlCl3And [ Cnmin]-x AlX3One or more of (a) or (b),
R1is selected from C1-C6Alkyl, preferably selected from methyl, ethyl, isopropyl and n-propyl;
x is 0.5-10, preferably 0.5-5;
n is 1 to 6, preferably 1 to 4;
x is a halogen, preferably selected from chlorine and bromine.
8. The preparation method according to any one of claims 4 to 7, wherein in the step (1), the volume ratio of the raw material to the solvent is 1-10: 1, preferably 1-6: 1; the reaction temperature is 40-100 ℃, preferably 60-75 ℃, and the reaction pressure is 0-2 bar, preferably 0.1-0.8 bar.
9. The process according to any one of claims 4 to 8, wherein the catalyst active component is present in an amount of 1 to 10%, preferably 1 to 5% by weight of the catalyst.
10. Use of cyclohexane obtained by the process according to any one of claims 4 to 9 for the preparation of cyclohexanol, cyclohexanone, adipic acid, caprolactam or any other product starting from cyclohexane.
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| US20140114100A1 (en) * | 2012-10-18 | 2014-04-24 | Basf Se | Novel process for preparing cyclohexane from methylcyclopentane and benzene |
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| CN105439801A (en) * | 2014-08-27 | 2016-03-30 | 中国石油化工股份有限公司 | A preparing method of cyclohexane |
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Application publication date: 20210330 |