CN114621052A - Method and device for industrially preparing cyclohexanol - Google Patents
Method and device for industrially preparing cyclohexanol Download PDFInfo
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- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
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- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
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Abstract
The application discloses a method and a device for industrially preparing cyclohexanol. The method comprises the following steps: a pretreatment stage, a reaction stage, a heat recovery stage and a separation stage; the pre-treatment stage comprises: performing pretreatment on the cyclohexyl acetate a, wherein the pretreatment comprises water removal treatment; the reaction stage comprises: respectively introducing a material I containing cyclohexyl acetate a and a material II containing hydrogen a into a hydrogenation reaction kettle, and contacting and reacting with a catalyst to obtain a hydrogenation reaction product containing cyclohexanol; the heat recovery stage comprises: respectively carrying out heat exchange treatment on the material I and the material II by using the hydrogenation reaction product; the separation stage comprises: and performing multistage rectification on the hydrogenation reaction product after heat exchange to obtain a cyclohexanol product and an ethanol byproduct. The method can realize the industrialized production of cyclohexanol, comprises an integral treatment process, and realizes the optimized utilization of energy of hydrogenation reaction products, hydrogen recovery and the separation of cyclohexanol and ethanol byproducts as main products.
Description
Technical Field
The application relates to a method and a device for industrially preparing cyclohexanol, belonging to the field of chemical raw material preparation.
Background
Cyclohexanol is a good organic chemical intermediate raw material with high boiling point and low volatility, is widely applied to the production and manufacture of industrial and daily chemical products such as paint solvents, dyes, disinfectants, insecticides and the like, and is an important chemical resource for producing chemical products such as hexamethylene diamine, adipic acid, nylon 66, caprolactam and the like. Currently, cyclohexanol is industrially prepared mainly by phenol hydrogenation, cyclohexane oxidation and cyclohexene hydration. Wherein, the phenol hydrogenation method adopts a nickel-based catalyst, phenol and hydrogen react at 150 ℃ and 2.5MPa to generate cyclohexanol, and the method is gradually eliminated along with the continuous rising of the cost of phenol; the cyclohexane method takes air or oxygen as an oxidant to oxidize cyclohexane to generate cyclohexanol, the process flow is complex, and the catalyst needs to be quickly recovered; the cyclohexene hydration method is divided into a direct hydration method and an indirect hydration method, wherein the direct hydration method directly obtains a cyclohexanol product through a carbon cation reaction on a catalyst, the reaction of the cyclohexene hydration method and carboxylic acid generates a carboxylic ester intermediate product, and the ester is hydrolyzed to obtain cyclohexanol. The preparation of cyclohexanol by esterification and hydrogenation of cyclohexene is a novel cyclohexanol preparation process, uses cheap acetic acid as an esterification raw material, has high cyclohexene conversion rate and cyclohexanol selectivity, has relatively mild reaction conditions, and is a new development direction of a cyclohexanol production process.
The preparation of cyclohexanol by esterification and hydrogenation of hexene is a new technology, uses cheap acetic acid as an esterification raw material, has high cyclohexene conversion rate and cyclohexanol selectivity, has relatively mild reaction conditions, and is a new development direction of cyclohexanol production technology.
In summary, at present, few reports exist on the whole flow research of preparing cyclohexanol by hydrogenating cyclohexyl acetate, and energy optimization, hydrogen recovery and impurity separation are not fully considered in the existing reported flow. For the reasons above, it is necessary to design the process for preparing cyclohexanol by hydrogenating cyclohexyl acetate into a systematic comprehensive design.
Disclosure of Invention
According to one aspect of the application, the method for industrially preparing cyclohexanol is provided, can realize industrial production of cyclohexanol, comprises an integral treatment process, and realizes energy optimized utilization, hydrogen recovery and separation of cyclohexanol and ethanol byproduct serving as main products of hydrogenation reaction products.
A method for the industrial preparation of cyclohexanol, the method comprising a pre-treatment stage, a reaction stage, a heat recovery stage and a separation stage;
the pre-treatment stage comprises: performing pretreatment on the cyclohexyl acetate a, wherein the pretreatment comprises water removal treatment;
the reaction stage comprises: respectively introducing a material I containing cyclohexyl acetate a and a material II containing hydrogen a into a hydrogenation reaction kettle, and contacting and reacting with a catalyst to obtain a hydrogenation reaction product containing cyclohexanol;
the heat recovery stage comprises: respectively carrying out heat exchange treatment on the material I and the material II by utilizing the hydrogenation reaction product;
the separation stage comprises: and performing multistage rectification on the hydrogenation reaction product after heat exchange to obtain a cyclohexanol product and an ethanol byproduct.
Specifically, the catalyst is a supported copper-based catalyst.
The catalyst is a supported copper-based catalyst;
the supported copper-based catalyst comprises a Cu element and a carrier;
the Cu element is supported on the carrier.
The support may be alumina.
Optionally, in the reaction stage, the reaction conditions are: the reaction temperature is 180-260 ℃; the reaction pressure is 2.5-3.6 MPaG.
Optionally, in the reaction stage, the material I also comprises recycle cyclohexyl acetate b;
the material II also comprises circulating hydrogen b.
Optionally, the hydrogenation reaction product comprises: hydrogen, methane, ethane, ethanol, cyclohexane, cyclohexyl acetate and dicyclohexyl dimer.
Optionally, the reaction stage comprises: exchanging heat between a material I containing cyclohexyl acetate a and cyclic cyclohexyl acetate b and part of the hydrogenation reaction product, heating to a reaction temperature, and introducing into the hydrogenation reaction kettle;
and (3) exchanging heat between a material II containing hydrogen a and circulating hydrogen b and the other part of the hydrogenation reaction product, heating to the reaction temperature, and introducing into the hydrogenation reaction kettle.
Optionally, before the multistage rectification treatment, the method further comprises cooling the hydrogenation reaction product after heat exchange, and then performing a first flash evaporation treatment to separate a hydrogen-rich gas and a condensate a.
Specifically, the cooling treatment comprises cooling the hydrogenation reaction product after heat exchange to 40-50 ℃.
The conditions of the first flash treatment were: flash evaporation is carried out under the pressure of 2.4-3.4 MPaG.
Optionally, carrying out second flash evaporation treatment on the hydrogen-rich gas, separating out circulating hydrogen b and condensate b, pressurizing the circulating hydrogen b for recycling, and introducing the condensate b into a light component removal tower;
the condensate a is also introduced into the lightness-removing column.
Specifically, the hydrogen-rich gas is cooled to-25-0 ℃, and then subjected to second flash evaporation under the pressure of 2.4-3.4 MPaG.
Optionally, the condensate a and the condensate b are subjected to rectification treatment a in the light component removal tower, a gas/liquid phase mixture is obtained at the tower top, and a light component removal mixture is obtained at the tower bottom;
the gas/liquid phase mixture at the top of the tower is subjected to fractional condensation treatment to separate a gas phase light component and a liquid phase, the gas phase light component is discharged as waste gas, and the liquid phase returns to the light component removal tower;
and introducing the light component removal mixture in the tower kettle into an ethanol recovery tower.
The operating conditions in the light component removal tower are as follows: the pressure of the tower top is 1-500 kPaG, and the temperature of the tower kettle is 100-150 ℃.
Optionally, the light component removal mixture in the tower bottom is fed into an ethanol recovery tower to be rectified b, an ethanol byproduct with the mass concentration of more than 99.5% is separated at the tower top, and an ester-alcohol mixture is obtained in the tower bottom.
Specifically, the operating conditions of the ethanol recovery column are: the pressure of the tower top is 1-500 kPaG, and the temperature of the tower kettle is 120-180 ℃.
Optionally, introducing the ester-alcohol mixture into an ester recovery tower for rectification treatment c, separating unreacted cyclic cyclohexyl acetate b at the tower top, and obtaining cyclohexanol containing heavy component impurities at the tower bottom.
Specifically, the operating conditions of the ester recovery column are: the pressure of the tower top is 1-500 kPaG, and the temperature of the tower kettle is 120-180 ℃.
Optionally, introducing the cyclohexanol containing heavy component impurities into a cyclohexanol de-weighting tower for rectification treatment d, so as to obtain a cyclohexanol product with a molar concentration of more than 99.0% at the tower top, and obtain heavy component impurities at the tower bottom.
Specifically, the operating conditions of the cyclohexanol de-weighting column are as follows: the pressure of the tower top is 1-500 kPaG, and the temperature of the tower kettle is 120-200 ℃.
According to a second aspect of the present application, there is also provided an apparatus for industrially preparing cyclohexanol, the apparatus including a pretreatment unit, a reaction unit, a heat recovery unit, and a separation unit;
the pretreatment unit comprises a dehydrator;
the reaction unit comprises a first mixer, a first preheater, a second mixer, a second preheater and a hydrogenation reaction kettle;
the first mixer and the first preheater are sequentially connected with the hydrogenation reaction kettle;
the second mixer and the second preheater are sequentially connected with the hydrogenation reaction kettle;
the dehydrator is connected with the first mixer;
the heat recovery unit comprises a first heat exchanger, a second heat exchanger and a third mixer;
the first heat exchanger is communicated with the first mixer and the first preheater, and is communicated with the hydrogenation reaction kettle, so that part of the hydrogenation reaction product exchanges heat with the material I;
the second heat exchanger is communicated with the second mixer and the second preheater, and is communicated with the hydrogenation reaction kettle, so that the other part of the hydrogenation reaction product exchanges heat with a material II;
the third mixer is respectively communicated with the first heat exchanger and the second heat exchanger so as to mix hydrogenation reaction products after heat exchange;
the separation unit comprises a light component removal tower, an ethanol recovery tower, an ester recovery tower and a cyclohexanol recovery tower which are connected in sequence;
and the third heat exchanger is connected with the light component removal tower.
Optionally, a condenser, a first flash tank and a second flash tank are further arranged between the third heat exchanger and the light component removal tower;
an inlet of the condenser is communicated with the third heat exchanger;
the outlet of the condenser is communicated with the first flash tank;
the bottom of the first flash tank is communicated with the lightness-removing tower;
the top of the first flash tank is communicated with the second flash tank;
the top of the second flash tank is communicated with a second mixer;
the bottom of the second flash tank is communicated with the light component removal tower.
The beneficial effect that this application can produce includes:
1) the method for industrially preparing cyclohexanol can realize industrial production of cyclohexanol, comprises an integral treatment process, realizes energy optimized utilization of hydrogenation reaction products, hydrogen recovery, separation of cyclohexanol and ethanol byproduct serving as main products, and can effectively separate impurities.
2) The device for industrially preparing cyclohexanol has the advantages of simple structure of the separation unit and low equipment cost.
3) The method for industrially preparing cyclohexanol provided by the application realizes the recycling of hydrogen and cyclohexyl acetate.
Drawings
FIG. 1 is a schematic diagram of a hydrogenation reaction and hydrogen separation and recovery process.
FIG. 2 is a schematic diagram of a product refining process.
Detailed Description
The present application will be described in detail with reference to examples, but the present application is not limited to these examples.
Unless otherwise specified, the raw materials and catalysts in the examples of the present application were all purchased commercially.
Some possible embodiments are described below
The invention aims to provide an energy-saving and environment-friendly process technology for preparing cyclohexanol by hydrogenating cyclohexyl acetate, namely, a methodology of process system engineering is adopted to realize mass-energy comprehensive integration. The aim of lowest thermal power energy consumption and raw material consumption in the process is to realize the comprehensive optimization of a rectification sequence and a heat exchange network, and finally, the energy-saving and environment-friendly process for preparing cyclohexanol by esterification-hydrogenation of cyclohexene is provided.
The technical scheme of the invention is as follows:
as shown in figure 1, after a small amount of water carried in fresh cyclohexyl acetate is removed in a dehydrator, the fresh cyclohexyl acetate is fully mixed with circulating cyclohexyl acetate in a liquid phase, exchanges heat with part of hydrogenation reaction products, is heated to the reaction temperature by a first preheater and enters a hydrogenation reactor;
fully mixing fresh hydrogen and circulating hydrogen in a gas phase, then exchanging heat with partial hydrogenation reaction products, heating to the reaction temperature by a second preheater, entering a hydrogenation reactor, and carrying out hydrogenation reaction with cyclohexyl acetate through a catalyst under the pressure of 2.5-3.6 MPaG and the temperature of 180-260 ℃;
respectively exchanging heat between the hydrogenation reaction product and hydrogen and cyclohexyl acetate, cooling to 40-50 ℃, flashing at the pressure of 2.4-3.4 MPaG, separating hydrogen-rich gas and condensate, and sending the condensate to lightness removal;
cooling the hydrogen-rich gas to-25-0 ℃, flashing under the pressure of 2.4-3.4 MPaG, separating out circulating hydrogen, pressurizing and recycling, and feeding the obtained liquid into a light component removal tower;
as shown in figure 2, the top pressure of the light component removal tower is 1-500 kPaG, the temperature of the tower kettle is 100-150 ℃, gas-phase light components are separated from the tower top, the gas-phase light components are sent to a torch pipe network, light component removal mixture is obtained from the tower bottom, and the mixture is sent to an ethanol recovery tower.
The pressure of the top of the ethanol recovery tower is 1-500 kPaG, the temperature of the bottom of the tower is 120-180 ℃, ethanol by-products with the mass concentration of more than 99.5% are separated from the top of the tower, and the ester-alcohol mixture obtained from the bottom of the tower is sent to an ester recovery tower.
The pressure of the tower top of the ester recovery tower is 1-500 kPaG, the temperature of a tower kettle is 120-180 ℃, unreacted cyclic cyclohexyl acetate raw materials are separated from the tower top, a small part of the unreacted cyclic cyclohexyl acetate raw materials are discharged as waste liquid, a large part of the unreacted cyclic cyclohexyl acetate raw materials are circularly returned to a hydrogenation reactor, cyclohexanol containing heavy component impurities is obtained from the tower kettle, and the cyclohexanol is sent to a cyclohexanol de-weighting tower.
The pressure of the top of the cyclohexanol de-weighting tower is 1-500 kPaG, the temperature of the tower kettle is 120-200 ℃, a cyclohexanol product with the molar concentration of more than 99.0% is obtained at the top of the tower, and the cyclohexanol product exchanges heat with an esterification reaction product to recover heat, and heavy component impurities are obtained at the tower kettle.
The invention has the advantages of energy-saving and environment-friendly new process for producing cyclohexanol, is suitable for industrial production and can generate obvious economic and social benefits.
Example 1
The following detailed description of the invention refers to the accompanying drawings. The technique of the present invention will be further described by taking 5 ten thousand tons of cyclohexanol per year of industrial equipment as an example.
The catalyst in this example was 35% copper supported on an alumina framework.
As shown in figure 1, the flow rate of the cyclohexyl acetate from the upstream device is 9021.5kg/h, wherein the flow rate contains 98.5 percent of cyclohexyl acetate a and 0.5 percent of water by mole fraction, after moisture is removed to be below 0.1ppmv by a dehydrator V101, the cyclohexyl acetate a and the recycle cyclohexyl acetate b are fully mixed in a first mixer Q1, and are sent to a hydrogenation reactor R101 by a first heat exchanger E105 and a first preheater E101 after being heated to a reaction temperature through hydrogenation reaction products and public works. The flow rate of the fresh hydrogen a flowing into the system is 260.5kg/h, the fresh hydrogen a and the circulating hydrogen b are fully mixed in the second mixer Q2, and then are heated to the reaction temperature through the hydrogenation reaction products and the public works through the second heat exchanger E106 and the second preheater E102, and then are sent into the hydrogenation reactor R101. The temperature of the raw material at the inlet of the hydrogenation reactor was 200 ℃ and the reaction pressure was 2.9MPaG, and the obtained hydrogenation reaction product had the composition shown in the following table:
| components | mol(％) |
| Hydrogen | 85.7657 |
| Methane | 0.4526 |
| Ethane (III) | 0.0554 |
| Ethanol | 4.3036 |
| Cyclohexanol derivatives | 9.3210 |
| Acetic acid cyclohexyl ester | 0.7908 |
| Dimeric cyclohexene | 0.0329 |
The hydrogenation reaction product is divided into two parts, the proportion is 55 percent and 45 percent, the two parts exchange heat with a hydrogen material II and a cyclohexyl acetate material I respectively, and the heat recovery rate is 2322 kW. Then, the mixture was mixed in a third mixer Q3, cooled to 43 ℃ by a cooler E107, and then introduced into a first flash tank V102. The first flash tank V102 was operated at 43 ℃ and 2.89 MPaG. The liquid phase (i.e. the condensate a) separated from the first flash tank V102 is sent to a lightness-removing column T101, the gas phase is cooled to-10 ℃ through a cooler E104, the gas phase is sent to a deep cooling second flash tank V103 for flash evaporation, the operating temperature of the second flash tank V103 is-10 ℃, the operating pressure is 2.88MPaG, the separated liquid phase (i.e. the condensate b) is sent to the lightness-removing column T101, the gas phase is hydrogen with the mole fraction of 99.4%, and the hydrogen is pressurized through a hydrogen compressor C101 and then recycled.
As shown in fig. 2, the operating conditions of the lightness-removing column T101 are as follows: the overhead pressure was 3kPaG and the bottom temperature was 110 ℃. The tower top adopts a dephlegmator, the extracted gas phase is light component waste gas and is sent to a torch pipe network, and the liquid phase is totally refluxed back to the tower. And (4) obtaining a light component removal mixture at the tower bottom, and sending the light component removal mixture to an ethanol recovery tower T102.
The operating conditions of the ethanol recovery column T102 were as follows: the pressure at the top of the column was 3kPaG and the operating temperature at the bottom of the column was 146 ℃. A full condenser is adopted at the top of the tower to obtain an ethanol byproduct with the mass fraction of 99.62 percent, and a mixture of cyclohexanol and cyclohexyl acetate is obtained at the bottom of the tower and sent to an ester recovery tower T103.
The operating conditions of the ester recovery column T103 were as follows: the overhead pressure was 3kPaG and the operating temperature of the column bottom was 148 ℃. And a full condenser is adopted at the tower top to obtain the cyclohexyl acetate with the mole fraction of 12.86%, wherein 99% is used as a circulating hydrogenation reaction raw material, and the rest is discharged as waste liquid. The crude cyclohexanol with a mole fraction of 98.8% obtained at the bottom of the column is sent to a cyclohexanol de-weighting column T104.
The operating conditions of the cyclohexanol recovery column T104 were as follows: the overhead pressure was 3kPaG and the operating temperature of the column bottom was 149 ℃. Heavy component waste liquid is separated from the bottom of the tower, a full condenser is adopted at the top of the tower, and cyclohexanol products with the mole fraction of 99.1% are obtained, and the mass flow rate is 6.84 t/h.
Although the present application has been described with reference to a few embodiments, it should be understood that various changes, substitutions and alterations can be made herein without departing from the spirit and scope of the application as defined by the appended claims.
Claims (8)
1. The method for industrially preparing cyclohexanol is characterized by comprising a pretreatment stage, a reaction stage, a heat recovery stage and a separation stage;
the pre-treatment stage comprises: performing pretreatment on the cyclohexyl acetate a, wherein the pretreatment comprises water removal treatment;
the reaction stage comprises: respectively introducing a material I containing cyclohexyl acetate a and a material II containing hydrogen a into a hydrogenation reaction kettle, and contacting and reacting with a catalyst to obtain a hydrogenation reaction product containing cyclohexanol;
the heat recovery stage comprises: respectively carrying out heat exchange treatment on the material I and the material II by using the hydrogenation reaction product;
the separation stage comprises: and performing multistage rectification on the hydrogenation reaction product after heat exchange to obtain a cyclohexanol product and an ethanol byproduct.
2. The process according to claim 1, characterized in that in the reaction stage the reaction conditions are: the reaction temperature is 180-260 ℃; the reaction pressure is 2.5-3.6 MPaG.
3. The process according to claim 1, characterized in that in the reaction stage, the feed I also contains recycled cyclohexyl acetate b;
the material II also comprises circulating hydrogen b.
4. The method of claim 1, wherein the hydrogenation reaction product comprises: hydrogen, methane, ethane, ethanol, cyclohexane, cyclohexyl acetate and dicyclohexyl dimer.
5. The method of claim 1, wherein the reaction stage comprises: exchanging heat between a material I containing cyclohexyl acetate a and cyclic cyclohexyl acetate b and part of the hydrogenation reaction product, heating to a reaction temperature, and introducing into the hydrogenation reaction kettle;
and (3) exchanging heat between a material II containing hydrogen a and circulating hydrogen b and the other part of the hydrogenation reaction product, heating to the reaction temperature, and introducing into the hydrogenation reaction kettle.
6. The method according to claim 1, characterized in that before the multistage rectification treatment, the method further comprises a step of cooling the hydrogenation reaction product after heat exchange, and then a step of first flash evaporation treatment, wherein hydrogen-rich gas and condensate a are separated;
preferably, the hydrogen-rich gas is subjected to second flash evaporation treatment, circulating hydrogen b and condensate b are separated, the circulating hydrogen b is recycled after pressurization, and the condensate b is introduced into the light component removal tower;
the condensate a is also introduced into the lightness-removing tower;
preferably, the condensate a and the condensate b are rectified in the lightness-removing column a to obtain a gas/liquid phase mixture at the top of the column and a lightness-removing mixture at the bottom of the column;
the gas/liquid phase mixture at the top of the tower is subjected to fractional condensation treatment to separate a gas phase light component and a liquid phase, the gas phase light component is discharged as waste gas, and the liquid phase returns to the light component removal tower;
introducing the light component removal mixture in the tower kettle into an ethanol recovery tower;
preferably, the light component removal mixture in the tower bottom is fed into an ethanol recovery tower for rectification treatment b, an ethanol byproduct with the mass concentration of more than 99.5% is separated from the tower top, and an ester-alcohol mixture is obtained in the tower bottom;
preferably, the ester-alcohol mixture is fed into an ester recovery tower to be rectified c, unreacted cyclic cyclohexyl acetate b is separated from the tower top, and cyclohexanol containing heavy component impurities is obtained at the tower bottom;
preferably, the cyclohexanol containing the heavy component impurities is introduced into a cyclohexanol de-weighting tower to be rectified d, a cyclohexanol product with the molar concentration of more than 99.0% is obtained at the tower top, and the heavy component impurities are obtained at the tower bottom.
7. The device for industrially preparing cyclohexanol is characterized by comprising a pretreatment unit, a reaction unit, a heat recovery unit and a separation unit;
the pretreatment unit comprises a dehydrator;
the reaction unit comprises a first mixer, a first preheater, a second mixer, a second preheater and a hydrogenation reaction kettle;
the first mixer, the first preheater and the hydrogenation reaction kettle are sequentially connected;
the second mixer and the second preheater are sequentially connected with the hydrogenation reaction kettle;
the dehydrator is connected with the first mixer;
the heat recovery unit comprises a first heat exchanger, a second heat exchanger and a third mixer;
the first heat exchanger is communicated with the first mixer and the first preheater, and is communicated with the hydrogenation reaction kettle, so that part of the hydrogenation reaction product exchanges heat with the material I;
the second heat exchanger is communicated with the second mixer and the second preheater, and is communicated with the hydrogenation reaction kettle, so that the other part of the hydrogenation reaction product exchanges heat with a material II;
the third mixer is respectively communicated with the first heat exchanger and the second heat exchanger so as to mix hydrogenation reaction products after heat exchange;
the separation unit comprises a light component removal tower, an ethanol recovery tower, an ester recovery tower and a cyclohexanol recovery tower which are connected in sequence;
and the third heat exchanger is connected with the light component removal tower.
8. The device according to claim 7, wherein a condenser, a first flash tank and a second flash tank are further arranged between the third heat exchanger and the lightness-removing column;
an inlet of the condenser is communicated with the third heat exchanger;
the outlet of the condenser is communicated with the first flash tank;
the bottom of the first flash tank is communicated with the lightness-removing tower;
the top of the first flash tank is communicated with the second flash tank;
the top of the second flash tank is communicated with a second mixer;
the bottom of the second flash tank is communicated with the light component removal tower.
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| CN111470941A (en) * | 2020-03-21 | 2020-07-31 | 河南神马尼龙化工有限责任公司 | High-quality cyclohexanol production device and process |
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