Cumene hydroperoxide production equipment and production method

Abstract

Production equipment for oxidizing cumene to produce cumene hydroperoxide, said equipment comprising: a device A that oxidizes cumene to obtain cumene hydroperoxide; and a heat exchange system X, wherein the heat exchange system X comprises a medium capable of both heating and cooling the oxidation reaction system, a medium cooling unit capable of cooling the medium, and a medium heating unit capable of heating the medium.

Description

[Technical Field]

[0001] The present invention relates to a facility and a method for producing cumene hydroperoxide, and more particularly to a facility and a method for producing cumene hydroperoxide, for efficiently starting up a step of obtaining cumene hydroperoxide by oxidizing cumene in a continuous propylene oxide production system. [Background technology]

[0002] A method for obtaining propylene oxide by reacting cumene hydroperoxide with propylene is known, and the obtained propylene oxide is purified by a purification step. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Laid-Open No. 2007-284419 Summary of the Invention [Problem to be solved by the invention]

[0004] The reaction of oxidizing cumene to produce cumene hydroperoxide is an exothermic reaction. Therefore, during steady-state operation (steady state) in a continuous process, it is preferable to cool the reaction system using a medium to prevent the temperature of the reaction system from rising too much. On the other hand, before the reaction reaches steady-state operation, i.e., at start-up, it is preferable to heat the reaction system in order to quickly reach a steady state.

[0005] An object of the present invention is to provide a production facility and a production method for cumene hydroperoxide that enable both efficient start-up and safe steady-state operation of a process for obtaining cumene hydroperoxide by oxidizing cumene. [Means for solving the problem]

[0006] The present invention relates to, but is not limited to, the following: [Invention 1] 1. A manufacturing facility for producing cumene hydroperoxide by oxidizing cumene, said facility comprising: A: an apparatus for oxidizing cumene to obtain cumene hydroperoxide; and X: Heat exchange system, Equipped with The heat exchange system X includes a medium capable of both heating and cooling the oxidation reaction system, a medium cooling unit capable of cooling the medium, and a medium heating unit capable of heating the medium. Manufacturing equipment. [Invention 2] The manufacturing facility according to claim 1, wherein the medium is a fluid containing water. [Invention 3] B: an apparatus for reacting cumene hydroperoxide with propylene to obtain propylene oxide and cumyl alcohol; and E: A device for converting cumyl alcohol into cumene, The manufacturing facility according to claim 1 or 2, [Invention 4] 4. The manufacturing facility according to any one of inventions 1 to 3, wherein the medium is cooled with a fluid containing at least one selected from water, the process fluid of device B, and the process fluid of device E. [Invention 5] C: Propylene separation equipment; D: a device for separating propylene oxide; and F: Cumene refining equipment, 5. The manufacturing facility according to any one of the first to fourth aspects, comprising at least one selected from the following: [Invention 6] The manufacturing facility according to invention 5, wherein the cooling medium is performed with a fluid including at least one selected from water, the process fluid of device C, the process fluid of device D, and the process fluid of device F. [Invention 7] The manufacturing facility according to invention 6, wherein the cooling medium is performed with a fluid including at least one selected from water, the process fluid of device C, and the process fluid of device D. [Invention 8] A production facility according to invention 7, wherein the device C includes a device C' for separating propane, and the medium is cooled by a fluid including the process fluid of the device C'. [Invention 9] The production facility according to invention 7 or 8, wherein the unit D is provided with a unit D' for separating heavy components, and the medium is cooled by a fluid including the process fluid of the unit D'. [Invention 10] A production facility according to any one of Inventions 7 to 9, wherein the unit D is provided with a unit D″ for separating light components, and the medium is cooled by a fluid including the process fluid of the unit D″. [Invention 11] 11. The production facility according to any one of Inventions 1 to 10, wherein the medium is heated with a fluid containing at least one selected from water (liquid) and water vapor. [Invention 12] 12. The production facility according to any one of Inventions 1 to 11, further comprising a cooling means other than the heat exchange system X as a cooling means for the oxidation reaction system. [Invention 13] 13. The manufacturing facility according to claim 12, wherein the cooling means is an air fin cooler. [Invention 14] 1. A method for producing cumene hydroperoxide, comprising the steps of: oxidizing cumene to obtain cumene hydroperoxide; and heating the oxidation reaction system in a medium x; heating the medium x cooled by the heating in a heat exchange system X; cooling the oxidation reaction system with a medium x; and A step of cooling the medium x heated by the cooling in a heat exchange system X. [Effects of the Invention]

[0007] According to the present invention, the reaction system can be heated when starting up the process for oxidizing cumene to obtain cumene hydroperoxide, and after the reaction system has been sufficiently heated, the reaction system can be cooled to prevent overheating. As a result, the process can be started up efficiently, and the temperature of the reaction system can be maintained at a predetermined temperature, enabling continuous operation. [Brief explanation of the drawings]

[0008] [Figure 1] An example of a cumene hydroperoxide production facility according to the present invention is shown below. [Figure 2] An example of a heat exchange system provided in the cumene hydroperoxide production facility of the present invention is shown. DETAILED DESCRIPTION OF THE INVENTION

[0009] definition All numbers disclosed herein are approximations, whether or not the word "about" or "approximately" is used in conjunction with them. They may vary by 1 percent, 2 percent, 5 percent, or sometimes 10-20 percent. The lower limit R L and upper limit R U Whenever a range of values ​​involving R = R is disclosed, any number falling within the range is specifically disclosed. Specifically, the following numbers within the range are specifically disclosed: R = R L +k * (R U -R L ) where k is a variable ranging from 1 percent to 100 percent in 1 percent increments, i.e., k is 1 percent, 2 percent, 3 percent, 4 percent, 5 percent, ..., 50 percent, 51 percent, 52 percent, ..., 95 percent, 96 percent, 97 percent, 98 percent, 99 percent, or 100 percent. Additionally, any numerical range defined by two R numbers as set forth above is also specifically disclosed.

[0010] The expression "lower limit to upper limit" expressing a numerical range means "greater than or equal to the lower limit, less than or equal to the upper limit," and the expression "upper limit to lower limit" means "less than or equal to the upper limit, greater than or equal to the lower limit." In other words, these expressions express a numerical range including the lower limit and the upper limit, but in one embodiment, one or both of the upper limit and the lower limit may be excluded, that is, "lower limit to upper limit" may express "more than the lower limit and less than the upper limit," "greater than or equal to the lower limit and less than the upper limit," or "more than the lower limit and less than the upper limit." Furthermore, "more than or equal to" and "less than" may express "more than" and "less than," respectively.

[0011] Hereinafter, several embodiments of the present invention will be described in detail with reference to Fig. 1. However, the present invention is not limited to the following embodiments.

[0012] Cumene hydroperoxide manufacturing facility Oxidation of cumene (1) is usually carried out by autoxidation using an oxygen-containing gas (2) such as air or oxygen-enriched air. In particular, an emulsion oxidation method in a water / alkaline emulsion is preferred from the viewpoint of improving the yield of cumene hydroperoxide. The reaction temperature is usually 50 to 200°C, and the reaction pressure is between atmospheric pressure and 5 MPa. In the emulsion oxidation method, the alkaline reagent (3) used may be an alkali metal compound such as NaOH or KOH, an alkaline earth metal compound, an alkali metal carbonate such as NaCO or NaHCO, or ammonia, NHCO, or an alkali metal ammonium carbonate.

[0013] The cumene hydroperoxide production facility of the present invention comprises: A: an apparatus for oxidizing cumene to produce cumene hydroperoxide; and X: Heat exchange system.

[0014] The heat exchange system X comprises a medium (Xm), a medium heating section (Xh), and a medium cooling section (Xc). The medium is capable of both heating and cooling the oxidation reaction system. The medium heating section can heat the medium to a temperature higher than that of the reaction system, and the heated medium can heat the reaction system. Furthermore, the medium cooling section can cool the medium to a temperature lower than that of the reaction system, and the cooled medium can cool the reaction system. The "reaction system" may also be referred to as a "reaction mixture," "reactor contents," "production apparatus contents," "reactor interior," or "production apparatus interior."

[0015] In one embodiment, the medium is a fluid comprising water, wherein the "water" is selected from liquid water, water vapor, and mixtures thereof.

[0016] In one embodiment, the cumene hydroperoxide production facility of the present invention comprises the following equipment: B: an apparatus for reacting cumene hydroperoxide with propylene to obtain propylene oxide and cumyl alcohol; and E: Equipment for converting cumyl alcohol to cumene. Here, cumyl alcohol refers to 2-phenyl-2-propanol.

[0017] In one embodiment, the cumene hydroperoxide obtained in the apparatus A (more precisely, the fluid (4) containing cumene hydroperoxide) may be used in the apparatus B, and the cumyl alcohol obtained in the apparatus B may be used in the apparatus E. In this specification, for example, "using the cumene hydroperoxide obtained in the apparatus A in the apparatus B" does not only mean that the cumene hydroperoxide obtained in the apparatus A is directly introduced into the apparatus B, but also means that the cumene hydroperoxide obtained in the apparatus A is subjected to treatments such as separation and purification in one or more apparatuses, and then the cumene hydroperoxide after the treatments is introduced into the apparatus B. The same applies to the other steps.

[0018] Preferably, the manufacturing facility further comprises at least one of the following devices: C: Propylene separation equipment; D: a device for separating propylene oxide; and F: Equipment for refining cumene.

[0019] When the production facility of the present invention is equipped with the unit C, the unreacted propylene in the unit B is separated in the unit C, and cumyl alcohol with improved purity is obtained. The cumyl alcohol obtained in the unit C may be used in the unit E. The propylene separated in the unit C may be used in the unit B.

[0020] The production facility of the present invention may be provided with an apparatus for further purifying the separated propylene, in addition to the apparatus C, and the purified propylene may be used in the apparatus B.

[0021] When the production facility of the present invention is equipped with Unit D, the propylene oxide obtained in Unit B may be separated in Unit D. Preferably, Unit D is provided in the production facility of the present invention together with Unit C, and the mixture containing cumyl alcohol obtained in Unit C, which also contains propylene oxide, is sent to Unit D, where the propylene oxide is separated, thereby obtaining cumyl alcohol with an improved purity. The cumyl alcohol obtained in Unit D may be used in Unit E.

[0022] The production facility of the present invention may be provided with an apparatus for further purifying the separated propylene oxide in addition to the apparatus D.

[0023] When the production facility of the present invention is equipped with the unit F, the cumene is purified by separating the by-products obtained together with the cumene in the unit E. The cumene obtained in the unit F, i.e., the cumene with improved purity, may be used in the unit A.

[0024] In one embodiment, the cooling of the medium is performed by a fluid comprising at least one selected from water, the process fluid of apparatus B, and the process fluid of apparatus E. In another embodiment, the cooling is performed by a fluid comprising at least one selected from water, the process fluid of apparatus C, the process fluid of apparatus D, and the process fluid of apparatus F. Preferably, the cooling is performed by a fluid comprising at least one selected from water, the process fluid of apparatus C, and the process fluid of apparatus D. Here, "the process fluid of apparatus Y" refers to a part or all of the fluid extracted from apparatus Y. When the process fluid is used as a medium in a heat exchange system, it may be advanced to the next apparatus (column) after use or returned to the same apparatus (column). In one embodiment, the cooling of the medium is performed in a further heat exchange system.

[0025] When cooling the medium, the cooling start temperature (medium temperature before cooling) and the cooling end temperature (medium temperature after cooling) are not limited, but the cooling start temperature is preferably 30 to 180°C, and the cooling end temperature is preferably 25 to 175°C.

[0026] In one embodiment, the propylene separation unit C comprises a plurality of units (columns), preferably each of which has different separation or purification conditions. In one embodiment, the unit C comprises a unit (column) C' for separating propane, which may be referred to as a "propane separation unit (column)."

[0027] In one embodiment, the medium is cooled by a fluid including a process fluid from one of the columns of the apparatus C, preferably the propane separation apparatus (column) C'.

[0028] In one embodiment, the unit D for separating propylene oxide comprises a plurality of units (towers), and preferably, each of the towers has different separation or purification conditions. In one embodiment, the unit D comprises a plurality of units (towers) for separating a plurality of components having different boiling points, and preferably comprises a unit (tower) D' for separating heavy components and a unit (tower) D" for separating light components. These may be referred to as a "heavy components separation unit (tower)" and a "light components separation unit (tower)", respectively. Here, the components with a relatively high boiling point are referred to as "heavy components", and the components with a relatively low boiling point are referred to as "light components". The "light components separation unit (tower)" may also be referred to as a "light boiling cut unit (tower)".

[0029] In one embodiment, the medium is cooled by a fluid that includes process fluid from any of the columns included in unit D, such as heavy separation unit (column) D' and / or light separation unit (column) D''.

[0030] In one embodiment, the heating of the medium is performed by a further heat exchange system. Preferably, the heating is performed by a fluid comprising at least one selected from water (liquid) and water vapor.

[0031] When heating the medium, the heating start temperature (medium temperature before heating) and heating end temperature (medium temperature after heating) are not limited, but the heating start temperature is preferably 20 to 150°C, and the heating end temperature is preferably 25 to 155°C.

[0032] In one embodiment, the cumene hydroperoxide production facility of the present invention further includes another means for cooling the reaction system of the cumene oxidation reaction. Examples of the other cooling means include an air fin cooler. Examples of the air fin cooler include a natural draft air fin cooler.

[0033] The present application also provides an invention relating to a method for producing cumene hydroperoxide in accordance with the above description of the cumene hydroperoxide production facility of the present invention.

[0034] The above-mentioned cumene hydroperoxide production facility can be suitably employed in the propylene oxide production method described below.

[0035] In one embodiment, a method for producing propylene oxide comprises the steps of: Step a: A step of oxidizing cumene to produce cumene hydroperoxide Step b: A step of reacting the cumene hydroperoxide obtained in step a with propylene to obtain a fluid b' containing propylene oxide and cumyl alcohol.

[0036] Step b is carried out using the above-mentioned apparatus B. Hereinafter, the reaction of cumene hydroperoxide with propylene in step b may be referred to as an "epoxidation reaction."

[0037] In step b, from the viewpoint of obtaining propylene oxide in high yield and with high selectivity, it is preferable to react cumene hydroperoxide with propylene in the presence of a catalyst containing a titanium-containing silicon oxide. The catalyst is preferably a so-called Ti-silica catalyst, which contains Ti chemically bonded to a silicon oxide. Examples of the catalyst include a Ti compound supported on a silica carrier, a compound with a silicon oxide prepared by a coprecipitation method or a sol-gel method, and a Ti-containing zeolite compound.

[0038] The epoxidation reaction can be carried out in the liquid phase using a solvent. The solvent should be liquid under the temperature and pressure of the reaction and substantially inert to the reactants and products. An example of a solvent is cumene.

[0039] The epoxidation reaction temperature is generally 0 to 200°C, preferably 25 to 200°C. The reaction pressure may be sufficient to maintain the reaction mixture in a liquid state. Generally, a pressure of 100 to 10,000 kPa-G (gauge pressure) is advantageous.

[0040] The epoxidation reaction can be advantageously carried out using the catalyst in slurry or fixed bed form, with fixed beds being preferred for large scale commercial operations, and can be carried out batchwise, semi-continuously, or continuously.

[0041] The fluid b' obtained in step b usually contains unreacted propylene.

[0042] In one embodiment, the method for producing propylene oxide comprises the following steps in addition to steps a and b: Step c: A step of separating propylene from the fluid b' obtained in step b to obtain a fluid c' containing propylene oxide and cumyl alcohol. Step c is carried out using the aforementioned apparatus C. Fluid c' may contain a small amount of propylene, the concentration of propylene in fluid c' being less than the concentration of propylene in fluid b'.

[0043] In one embodiment, the method for producing propylene oxide comprises, in addition to steps a, b, and c, the following steps: Step d: separating propylene oxide from the fluid c' obtained in step c to obtain a fluid d' containing cumyl alcohol; and / or Step e: A step of converting cumyl alcohol in the fluid c' obtained in step c or the fluid d' obtained in step d into cumene to obtain a cumene-containing stream e'. Step d is carried out using the aforementioned apparatus D. The concentration of cumyl alcohol in fluid d' is greater than the concentration of cumyl alcohol in fluid c'. Step e is carried out using the above-mentioned apparatus E. Examples of methods for converting cumyl alcohol to cumene include (e1) a method of obtaining cumene by hydrogenolysis of cumyl alcohol, and (e2) a method of dehydrating cumyl alcohol and then hydrogenating it to obtain cumene.

[0044] In the case of (e1), the raw material fluid (fluid c' or fluid d') and hydrogen are brought into contact with a catalyst in a reactor, and the cumyl alcohol in the raw material fluid is reacted with the hydrogen to obtain a fluid e' containing cumene.

[0045] Examples of catalysts used in hydrocracking reactions (hereinafter sometimes referred to as "hydrocracking catalysts") include catalysts containing metals from Groups 9, 10, 11, or 12 of the periodic table. Specific examples include cobalt-containing catalysts, nickel-containing catalysts, palladium-containing catalysts, copper-containing catalysts, and zinc-containing catalysts. From the viewpoint of suppressing the generation of by-products, nickel-containing catalysts, and copper-containing catalysts are preferred. Nickel-containing catalysts include nickel, nickel-alumina, nickel-silica, and nickel-carbon. Palladium-containing catalysts include palladium-alumina, palladium-silica, and palladium-carbon. Copper-containing catalysts include copper, Raney copper, copper-chromium, copper-zinc, copper-chromium-zinc, copper-silica, and copper-alumina.

[0046] The reactor used in the hydrocracking reaction contains any one or a combination of the above catalysts. The reactor can be in the form of a slurry bed or a fixed bed. For large-scale commercial operations, a fixed bed is preferred. The reaction is preferably carried out in a continuous manner.

[0047] The amount of hydrogen consumed in the hydrogenolysis reaction is equimolar to the amount of cumyl alcohol. However, since the raw material liquid usually contains components other than cumyl alcohol that consume hydrogen, it is preferable to supply hydrogen in excess of the stoichiometric amount in order to ensure the conversion rate of cumyl alcohol. Furthermore, the higher the partial pressure of hydrogen, the more rapidly the reaction proceeds. Therefore, the hydrogen / cumyl alcohol molar ratio is usually adjusted to 1 / 1 to 20 / 1, preferably 1 / 1 to 10 / 1, and more preferably 1 / 1 to 5 / 1. Furthermore, the hydrogen / (cumene + cumyl alcohol) molar ratio is usually 1 / 25 or more.

[0048] The excess hydrogen remaining after the hydrocracking reaction can be separated from the reaction liquid and then recycled for reuse. The hydrocracking reaction temperature is usually 0 to 500°C, preferably 50 to 450°C, and more preferably 150 to 300°C. The hydrocracking reaction pressure is usually 100 to 10,000 kPa-G, preferably 500 to 4,000 kPa-G, and more preferably 1,000 to 2,000 kPa-G.

[0049] When hydrogenolysis is applied, the conversion of cumyl alcohol is usually 90% or more.

[0050] In the case of (e2), the raw material fluid (fluid c' or fluid d') is brought into contact with a catalyst in a reactor to obtain a fluid containing α-methylstyrene by a dehydration reaction of cumyl alcohol in the raw material fluid, and then the fluid containing α-methylstyrene and hydrogen are brought into contact with the catalyst in the reactor to hydrogenate the α-methylstyrene and hydrogen, thereby obtaining a fluid e' containing cumene.

[0051] In this embodiment, the step (reaction) of dehydrating cumyl alcohol to obtain a fluid containing α-methylstyrene may be referred to as a "dehydration step (dehydration reaction)", and the step (reaction) of subjecting a fluid containing α-methylstyrene to a hydrogenation reaction with hydrogen to obtain a fluid e' containing cumene may be referred to as a "hydrogenation step (hydrogenation reaction)".

[0052] Examples of the catalyst used in the dehydration step (hereinafter sometimes referred to as "dehydration catalyst") include homogeneous acid catalysts such as sulfuric acid, phosphoric acid, and p-toluenesulfonic acid; and solid acid catalysts such as activated alumina, titania, zirconia, silica alumina, and zeolite. From the viewpoint of improving the reaction efficiency, the dehydration step is preferably carried out in the presence of a solid acid catalyst, and more preferably activated alumina.

[0053] The dehydration reaction in the dehydration step is usually carried out by contacting a fluid containing cumyl alcohol with a dehydration catalyst in a reactor. Since the hydrogenation reaction is carried out in the hydrogenation step following the dehydration reaction, the fluid containing cumyl alcohol may be contacted with the dehydration catalyst in the presence of hydrogen. The dehydration reaction temperature is usually 50 to 450°C, preferably 150 to 300°C. The dehydration reaction pressure is usually 10 to 10,000 kPa-G.

[0054] Examples of catalysts used in the hydrogenation step (hereinafter sometimes referred to as "hydrogenation catalysts") include catalysts containing metals from Group 10 or 11 of the periodic table. Specific examples include nickel-containing catalysts, palladium-containing catalysts, platinum-containing catalysts, and copper-containing catalysts. From the viewpoints of suppressing the nuclear hydrogenation reaction of aromatic rings and achieving high yields, nickel-containing catalysts, palladium-containing catalysts, and copper-containing catalysts are preferred. Preferred nickel-containing catalysts include nickel, nickel-alumina, nickel-silica, and nickel-carbon. Preferred palladium-containing catalysts include palladium-alumina, palladium-silica, and palladium-carbon. Preferred copper-containing catalysts include copper, Raney copper, copper-chromium, copper-zinc, copper-chromium-zinc, copper-silica, and copper-alumina. These catalysts can be used alone or in combination.

[0055] The hydrogenation step is carried out by bringing a fluid containing α-methylstyrene and hydrogen into contact with a hydrogenation catalyst in a reactor. The hydrogenation reaction is carried out subsequent to the above-mentioned dehydration reaction. In this embodiment, a part of the water generated in the dehydration reaction may be separated by oil-water separation or the like, or the water may be brought into contact with the hydrogenation catalyst together with α-methylstyrene without being separated.

[0056] The amount of hydrogen consumed in the hydrogenation reaction is equimolar to the amount of α-methylstyrene. However, since the raw material liquid usually contains components other than α-methylstyrene that consume hydrogen, it is preferable to supply hydrogen in excess of the stoichiometric amount in order to ensure the conversion rate of α-methylstyrene. Furthermore, the higher the hydrogen partial pressure, the more rapidly the reaction proceeds. Therefore, the hydrogen / α-methylstyrene molar ratio is usually adjusted to 1 / 1 to 20 / 1, preferably 1 / 1 to 10 / 1, and more preferably 1 / 1 to 5 / 1. The excess hydrogen remaining after the hydrogenation reaction can be separated from the reaction liquid and recycled for reuse. Furthermore, the hydrogen / (cumene + cumyl alcohol) molar ratio is usually 1 / 25 or more. In the case of (b), the amount of "hydrogen" in the molar ratio is the amount of hydrogen used in the hydrogenation reaction, and the amount of "cumene + cumyl alcohol" is the total amount of cumene and cumyl alcohol in the liquid used in the dehydration reaction.

[0057] The hydrogenation reaction temperature is usually 0 to 500° C., preferably 30 to 400° C., and more preferably 50 to 300° C. The hydrogenation reaction pressure is usually 100 to 10,000 kPa-G.

[0058] The dehydration reaction and the subsequent hydrogenation reaction may be carried out in a reactor containing a dehydration catalyst and a hydrogenation catalyst in this order from the upstream side within a single vessel, or in a reactor containing a catalyst in which the dehydration catalyst and the hydrogenation catalyst are physically mixed within a single vessel, or in a reactor containing a hydrogenation catalyst supported on a dehydration catalyst within a single vessel, or in a reactor in which a vessel containing a dehydration catalyst and a vessel containing a hydrogenation catalyst are connected in series in this order from the upstream side via a line.

[0059] The contact between the catalyst and the fluid in the vessel can be in the form of a slurry bed or a fixed bed, with the use of a fixed bed being preferred for large scale commercial operations.

[0060] In one embodiment, the method for producing propylene oxide comprises, in addition to steps a, b, c and / or d, and e, the following steps: Step f: A step of purifying the cumene in the fluid e' obtained in step e to obtain a fluid f' containing purified cumene. Step f is carried out using the aforementioned apparatus F. The cumene concentration in fluid f' is greater than the cumene concentration in fluid e'. In step f, impurities by-produced in at least one step selected from the group consisting of steps a, b, c, d, and e can be removed from fluid e'. Examples of impurities include acetophenone, cumene dimer, ethylbenzene, phenols, etc. Here, cumene dimer refers to compounds typified by 2,3-dimethyl-2,3-diphenylbutane, dicumyl ether, dicumyl peroxide, etc. Cumene is purified by distillation, washing with water, etc. The purified cumene may be recycled to step a.

[0061] <Startup process a> At start-up, step a may comprise the following steps: Step a1: charging a fluid containing cumene into an apparatus A; Step a2: heating the cumene-containing fluid charged in step a1 by the heat exchange system X to raise the temperature of the reaction system in the apparatus A to a predetermined temperature; Step a3: supplying an oxygen-containing fluid to the device A to initiate the oxidation reaction of cumene and increase the concentration of cumene hydroperoxide in the reaction system to a predetermined concentration; and Step a4: A step of discharging a fluid a′ containing cumene hydroperoxide from the device A and supplying the fluid a′ to the device B.

[0062] In steps a1, a2, and a3, it is preferable not to discharge the reaction liquid from the apparatus A until the concentration of cumene hydroperoxide in the reaction system increases to a predetermined concentration. In step a1, the cumene-containing fluid may contain 0.001 to 20% by weight of cumene hydroperoxide. In step a2, the temperature of the reaction system in the apparatus A is preferably increased to 80 to 95°C.

[0063] In step a3, the concentration of cumene hydroperoxide in the reaction system is preferably increased to 5 to 80% by weight, more preferably to 5 to 60% by weight, and even more preferably to 5 to 40% by weight, relative to 100% by weight of the fluid containing cumene hydroperoxide.

[0064] In step a4, together with discharging the fluid a', a fluid containing cumene may be introduced into the apparatus A. The amount of the fluid containing cumene to be introduced into the apparatus A is not particularly limited, but it is preferable to adjust the amount so that the liquid amount is constant.

[0065] After the start of step a4, it is preferable to cool the reaction system using a heat exchange system X so that the temperature of the reaction system is maintained at a predetermined temperature. The temperature of the reaction system is not particularly limited, but is usually 50 to 200°C, preferably 60 to 180°C, and more preferably 70 to 150°C. The pressure is usually between atmospheric pressure and 5 MPa-G, preferably 0.01 to 2 MPa-G, and more preferably 0.02 to 1 MPa-G. [Example]

[0066] The present invention will be specifically described below with reference to examples, although the present invention is not limited to the examples shown below.

[0067] Example 1 A simulation was carried out using the apparatus described in Invention 1. The simulation software used was DYNSIM Dynamic Simulation (AVEVA), and the amount of cumene hydroperoxide produced was calculated with reference to Journal of Chemical Engineering of Japan, 1970, 72.

[0068] A simulation model was created in the simulation software, which included one heat exchange system equipped with a medium capable of both heating and cooling the oxidation reaction system, a medium cooling section capable of cooling the medium, and a medium heating section capable of heating the medium, and one oxidation reactor. The reactor was filled with 100mℓ of 15% cumene hydroperoxide / cumene solution at 0.6MPa-G. 3 The medium was heated using the medium heating section of the heat exchange system, and the heated medium was used to heat the oxidation reaction system, raising the internal temperature of the oxidation reactor to 90°C. After that, 500 Nm of air heated to 90°C was introduced. 3 100 m3 / h, and cumene heated to 90°C was introduced at 4.8 tons / h. At the same time, unreacted gas was extracted from the reactor, and the liquid volume in the reactor was reduced to 100 m3. 3 The time when air introduction started was set as 0 hours, and the O2 concentration in the gas at the outlet of the reactor was checked every 6 hours. If the O2 concentration was 5% or less, air was introduced at 500 Nm 3 / h, and the feedstock cumene heated to 90°C was increased by 4.8 tons / h. In response to the rise in internal temperature due to the heat of reaction, the medium heating section used in the heat exchange system was switched to the medium cooling section to cool the medium. The cooled medium was used to cool the oxidation reactor, and the internal temperature was adjusted to approximately 108°C. After that, the liquid volume in the reactor was increased to 100 m 3 While maintaining air pressure of 2500Nm 3 The simulation continued until the reactor temperature reached 108°C, with a flow rate of 24 tons / h and cumene heated to 90°C. The cumene hydroperoxide concentration in the reactor reached approximately 13% by weight and the O2 concentration in the reactor outlet gas reached 2%. At this point, the time required from the start of air introduction to steady state was 30 hours.

[0069] Example 2 A simulation was carried out in the same manner as in Example 1, except that the reactor outlet gas O2 concentration was checked every three hours. As a result, the time required for stabilization was 15 hours.

[0070] Example 3 The feed rates of air heated to 90°C and raw cumene heated to 90°C were 1000 Nm 3 / h and 9.6 tonnes / h, with the final increase in intake volume being 500 Nm 3 A simulation was carried out in the same manner as in Example 1, except that the flow rates were set to 4.8 tons / h and 4.8 ton / h. As a result, the time required for stabilization was 16 hours.

[0071] Example 4 A simulation was carried out in the same manner as in Example 3, except that the temperatures of the heated air and the heated raw cumene were set to 100° C. As a result, the time required to reach a steady state was 16 hours.

[0072] Example 5 A simulation model was created in the simulation software, which included one heat exchange system equipped with a medium capable of both heating and cooling the oxidation reaction system, a medium cooling section capable of cooling the medium, and a medium heating section capable of heating the medium, and one oxidation reactor. The reactor was filled with 100mℓ of 10% cumene hydroperoxide / cumene solution at 0.6MPa-G. 3 The medium was heated using the medium heating section of the heat exchange system, and the heated medium was used to heat the oxidation reaction system, raising the internal temperature of the oxidation reactor to 90°C. After that, 370 Nm of air heated to 90°C was introduced. 3 100 m3 / h, and cumene heated to 90°C was introduced at 4.8 tons / h. At the same time, unreacted gas was extracted from the reactor, and the liquid volume in the reactor was reduced to 100 m3. 3 The time when air introduction started was set as 0 hours, and the O2 concentration in the gas at the outlet of the reactor was checked every 3 hours. If the O2 concentration was 5% or less, air was introduced at 370 Nm 3 / h, and the feedstock cumene heated to 90°C was increased by 4.8 tons / h. In response to the rise in internal temperature due to the heat of reaction, the medium heating section used in the heat exchange system was switched to the medium cooling section to cool the medium. The cooled medium was used to cool the oxidation reactor, and the internal temperature was adjusted to approximately 108-113°C. After that, the liquid volume in the reactor was increased by 100 m 3 2950Nm of air while maintaining 3 The simulation continued until the reactor temperature reached 113°C, with a flow rate of 38.4 tonnes / h and cumene heated to 90°C. The cumene hydroperoxide concentration in the reactor reached approximately 10% by weight and the O2 concentration in the reactor outlet gas was 2%, reaching a steady state. At this point, the time required from the start of air introduction to steady state was 24 hours.

[0073] Comparative Example 1 A simulation was performed in the same manner as in Example 1, assuming an oxidation reactor using a heat exchange system without heating the medium, except that the temperature inside the reactor before air introduction was set to 25°C. As a result, the O2 concentration did not fall below 5% within 30 hours, and the amount of air could not be increased. After 30 hours, the concentration of cumene hydroperoxide at the reactor outlet was 2.5 wt%.

[0074] From the above, it can be seen that by using an oxidation reaction facility having a heat exchange system equipped with a medium capable of both heating and cooling the oxidation reaction system, a medium cooling section capable of cooling the medium, and a medium heating section capable of heating the medium, it is possible to easily increase the cumene hydroperoxide concentration in the reactor to the target concentration. [Industrial Applicability]

[0075] The present invention is useful for the production of cumene hydroperoxide. The present invention is also useful for the production of propylene oxide. [Explanation of symbols]

[0076] 1: Kumen 2: Oxygen-containing gas 3: Fluids containing cumene hydroperoxide 4: Alkaline reagent 5: Exhaust gas containing unreacted oxygen-containing gas A: Oxidation reactor Xm: Medium Xh: Medium heating section (heat exchanger) Xc: Medium cooling section (heat exchanger) P: Pump V: Valve

Claims

1. A production facility for producing cumene hydroperoxide by oxidizing cumene, the facility comprising: A: An apparatus for oxidizing cumene to obtain cumene hydroperoxide; X: heat exchange system; E: an apparatus for converting cumyl alcohol to cumene; and F: A device for purifying the cumene converted in the device E; Equipped with a heat exchange system X is arranged so as to be able to both heat and cool the oxidation reaction system; The heat exchange system X includes a medium capable of both heating and cooling the oxidation reaction system, a medium cooling section arranged to be able to cool the medium, and a medium heating section arranged to be able to heat the medium. Manufacturing equipment.

2. The manufacturing facility according to claim 1 , wherein the medium is a fluid containing water.

3. B: An apparatus for reacting cumene hydroperoxide with propylene to obtain propylene oxide and cumyl alcohol; The manufacturing facility according to claim 1 or 2, comprising:

4. 4. The manufacturing facility according to claim 3, wherein the cooling medium is performed by a fluid including the process fluid of device B.

5. The manufacturing facility according to any one of claims 1 to 4, wherein the medium is cooled by a fluid containing at least one selected from water and the process fluid of the device E.

6. C: a device for separating propylene; and D: A device for separating propylene oxide, The manufacturing facility according to any one of claims 1 to 5, comprising at least one selected from the following:

7. The manufacturing facility according to claim 6, wherein the medium is cooled by a fluid including at least one selected from the process fluid of the device C and the process fluid of the device D.

8. The manufacturing facility according to any one of claims 1 to 7, wherein the medium is cooled by a fluid containing at least one selected from water and a process fluid of the device F.

9. The production facility according to claim 6, claim 7, or claim 8 which relies on claim 6 or 7, wherein the device C includes a device C' for separating propane, and the medium is cooled by a fluid including the process fluid of the device C'.

10. The manufacturing facility according to claim 6, claim 7, claim 8 or claim 9 which relies on claim 6 or 7, wherein the unit D is provided with a unit D' for separating heavy components, and the medium is cooled by a fluid including the process fluid of the unit D'.

11. The production facility according to claim 6, claim 7, claim 8, claim 9, or claim 10, which is dependent on claim 6 or claim 7, wherein the unit D comprises a unit D" for separating light components, and the medium is cooled by a fluid including the process fluid of the unit D".

12. The manufacturing facility according to any one of claims 1 to 11, wherein the medium is heated by a fluid containing at least one selected from water (liquid) and water vapor.

13. The production facility according to any one of claims 1 to 12, further comprising a cooling means separate from the heat exchange system X as a cooling means for the oxidation reaction system.

14. The manufacturing facility of claim 13, wherein the cooling means is an air fin cooler.

15. 1. A method for producing cumene hydroperoxide, comprising the steps of: a step of oxidizing cumene to obtain cumene hydroperoxide; converting the cumyl alcohol to cumene; purifying the cumene converted in the previous step; heating the oxidation reaction system in a medium x; heating the cooled medium x in a heat exchange system X; cooling the oxidation reaction system with a medium x; and Cooling the heated medium x in a heat exchange system X.

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