Method and system for oxidizing cumene and hydrocarbons

Abstract

The invention relates to a method and a system for oxidizing cumene and hydrocarbons. A process for oxidizing hydrocarbons, the process comprising: feeding an oxidizing agent to the top of a reactor; reacting the hydrocarbon with an oxidizing agent in the reactor to obtain a reaction product stream exiting a reactor outlet at the bottom of the reactor; and recycling a portion of the reaction product stream to the top of the reactor; and introducing an oxidant into an oxidation liquid comprising a portion of the reaction product stream recycled to the top of the reactor to form a reaction medium stream entering the reactor inlet at the top of the reactor. The pressure at the reactor outlet exceeds the pressure at the reactor inlet by at least 5%. The flow of reaction medium moves vertically downward in the reactor.

Description

[0001] This application is a divisional application of Chinese Patent Application No. 202180018291.5, titled "Methods and Systems for the Oxidation of Cumene and Hydrocarbons", with a filing date of March 2, 2021.

[0002] Citation of Related Applications

[0003] This application claims the priority and benefit of Russian Application No. 2020109437, filed on March 3, 2020, the content of which is incorporated herein by reference in its entirety. Technical Field

[0004] The present invention relates to methods and systems for the oxidation of cumene and hydrocarbons. Background Art

[0005] The cumene process synthesizes phenol and acetone from benzene and propylene. Other reactants in this process are oxygen and a free radical initiator.

[0006] More specifically, cumene can be formed by alkylating benzene with propylene. Benzene and propylene are compressed together in the presence of a catalyst, and cumene is oxidized in air, which removes the tertiary benzylic hydrogen from cumene and forms a cumene radical. The cumene radical bonds with an oxygen molecule to obtain a cumene hydroperoxide radical, which in turn forms cumene hydroperoxide (C6H5C(CH3)2 - O - O - H) (CHP) by extracting a benzylic hydrogen from another cumene molecule. This cumene is converted to a cumene radical and fed back into the subsequent chain formation of cumene hydroperoxide. CHP is then decomposed in an acidic medium to obtain phenol and acetone. First, the terminal hydroperoxide oxygen atom is protonated. This is followed by water molecule elimination, and the phenyl group migrates from the benzylic carbon to the adjacent oxygen, generating a stable tertiary carbocation. Then, the resulting carbocation is attacked by water, a proton is transferred from the hydroxyl oxygen to the ether oxygen, and the ion splits into phenol and acetone. Summary of the Invention

[0007] In various embodiments, improved methods and systems for the oxidation of hydrocarbons and improved methods for the oxidation of cumene are disclosed.

[0008] The present disclosure provides a method for oxidizing hydrocarbons, the method comprising feeding an oxidizing agent to the top of a reactor; reacting the hydrocarbons with the oxidizing agent in the reactor to obtain a reaction product stream that exits the reactor at an outlet at the bottom of the reactor; recycling a portion of the reaction product stream to the top of the reactor; and introducing the oxidizing agent into an oxidation liquid comprising the portion of the reaction product stream recycled to the top of the reactor to form a reaction medium stream that enters the reactor at an inlet at the top of the reactor. The pressure at the reactor outlet exceeds the pressure at the reactor inlet by at least 5%. The reaction medium stream moves vertically downward in the reactor, and the downward linear velocity of the oxidation liquid exceeds the floating linear velocity of the oxidizing agent in the oxidation liquid, thereby providing a downward movement of the oxidizing agent in the reactor.

[0009] The present disclosure provides a system for oxidizing cumene, the system comprising a reactor for reacting cumene and an oxidizing agent to obtain a reaction product stream, the reactor comprising an oxidizing agent inlet at the top of the reactor; and a pump in fluid communication with the top and the bottom of the reactor for recycling a portion of the reaction product stream from the bottom of the reactor to the top of the reactor.

[0010] The present disclosure provides a method for oxidizing cumene, the method comprising feeding an oxidizing agent to the top of a reactor; reacting cumene with the oxidizing agent in the reactor to obtain a reaction product stream comprising cumene hydroperoxide that exits the reactor at an outlet at the bottom of the reactor; recycling a portion of the reaction product stream to the top of the reactor; and introducing the oxidizing agent into an oxidation liquid comprising the portion of the reaction product stream recycled to the top of the reactor to form a reaction medium stream that enters the reactor at an inlet at the top of the reactor. The pressure at the reactor outlet exceeds the pressure at the reactor inlet by at least 5%. The reaction medium stream moves downward in the reactor.

[0011] These and other features and characteristics are described in more detail below. Brief Description of the Drawings

[0012] The following is a brief description of the drawings, in which like elements are numbered similarly and presented for the purpose of illustrating the exemplary embodiments disclosed herein and not for the purpose of limiting the same.

[0013] Figure 1A is a view of an oxidation reactor with downward flow.

[0014] Figure 1B is Figure 1A a detailed view of a section of

[0015] Figure 2 It is an overview diagram of a system and method for producing hydrocarbons or cumene. Detailed Description

[0016] In the production of phenol and acetone, the oxidation of cumene can consume more power than any other stage. Although the oxidation reaction can be exothermic, this relatively low-potential heat may not be easily utilized, and relatively high power may be required for air compression (e.g., compressing the air input to the process), which can account for approximately two-thirds of the total electrical power consumption of the process. Improved methods for oxidizing hydrocarbons are desired, and more specifically, improved methods for oxidizing cumene.

[0017] The present disclosure provides improved methods and systems for oxidizing hydrocarbons (e.g., improved methods for oxidizing cumene). More specifically, the present disclosure provides that the oxidation reaction gas pumped from the top of the reactor to the bottom of the reactor can provide improved pressure utilization, since an oxygen-rich gas at a lower pressure can be introduced into the top of the reactor, and the pressure of this introduced gas gradually increases while moving to the bottom of the reactor, while the oxygen concentration decreases. This feature provides a lower oxygen partial pressure drop for the reactor compared to conventional reactors that utilize upward gas movement. This advantageous method of the present disclosure can provide improved oxidation conditions for the reactor at a lower pressure of the introduced oxygen-rich gas, and save power consumption due to the reduced air compression of the oxygen-rich gas introduced at a lower pressure. The reactor can be, for example, a tubular reactor or a vessel equipped with a heat exchanger, providing a vertical free movement of the reaction mixture flow from the top to the bottom and a linear velocity faster than that of upward floating bubbles.

[0018] Current practice dictates that a compressor provides compressed air for the oxidation process, and the hydrostatic pressure at the bottom of the oxidation reactor can be close to 3 bar (300 kPa). This feature combined with the movement of the oxygen-containing (e.g., oxidation) gas from the bottom to the top of a conventional reactor can result in a higher pressure and a higher oxygen concentration at the bottom of the reactor compared to the pressure and oxygen concentration at the top of the reactor. In other words, current practice dictates that there may be an oxygen deficiency at the top of the reactor, while there may be an excess of oxygen at the bottom of the reactor. This may lead to the need to over-compress the oxygen feed (e.g., air input) fed to the bottom of the reactor in order to subsequently provide satisfactory oxidation conditions in the process at the top of the reactor. Using the advantageous method disclosed herein, by providing gas input and gas movement from the top of the reactor to the bottom of the reactor, excessive air compression and / or energy consumption can be significantly reduced or avoided.

[0019] Cumene oxidation usually occurs in a series of reactors, where the cumene oxidation product passes through each reactor individually, and the concentration of cumene hydroperoxide in the reactor effluent gradually increases, reaching a 25 to 30% CHP concentration after the final reactor. The same is true for hydrocarbon oxidation. The reactor operating pressure can vary from 2 bar to 6 bar (200 kPa to 600 kPa) at the top reactor outlet. Additional hydrostatic pressure is added to these values at the bottom of the reactor, such that the air inlet pressure is 3 - 9 bar (300 - 900 kPa). The inlet air pressure is provided by an air compressor, which consumes 50% to 70% of the total electrical power of the entire process. The air compressor operates under adiabatic or near-adiabatic conditions, resulting in excessive power consumption and thus high energy consumption for the heating of the compressed air. Since the air temperature after the compressor is much higher than the oxidation reactor temperature, an additional heat exchanger is required to provide the required compressed air temperature, so excessive heat must be removed before the air is fed into the oxidation reactor.

[0020] Cumene oxidation selectivity has a maximum at moderate oxygen partial pressures where cumene oxidation occurs using air under different oxygen concentration conditions. Fresh air as referred to herein generally means air having an O2 concentration of 20.9 volume percent (vol%) based on the total volume of air. The reactor exhaust gas can contain 2 to 5 vol% O2. The total pressure in the reactor can be reduced from 3 bar to 9 bar to 2 bar to 6 bar (300 kPa to 900 kPa to 200 kPa to 600 kPa), which also increases the oxygen partial pressure difference between the reactor inlet and the reactor outlet. Overall higher pressures can lead to higher productivity, while overall lower pressures can lead to higher selectivity. Difficulties arise in achieving a balance between the two.

[0021] The present disclosure advantageously provides that by making the reactor outlet pressure higher than the reactor inlet pressure, this can help to achieve the desired, for example, optimal values of pressure and selectivity within the reactor. For example, the present disclosure provides that the reactor outlet pressure can exceed the reactor inlet pressure by at least 5%, such as at least 10%, such as at least 25%, at least 50%, or at least 100%.

[0022] A more complete understanding of the components, processes, and devices disclosed herein can be obtained by reference to the accompanying drawings. These drawings (also referred to herein as "figures") are merely schematic representations for convenience and ease of illustration of the present disclosure and are therefore not intended to represent the relative sizes and dimensions of the device or its components and / or to define or limit the scope of the exemplary embodiments. Although specific terms are used in the following description for clarity, these terms are intended to refer only to the specific structures of the embodiments chosen for illustration in the drawings and are not intended to define or limit the scope of the present disclosure. In the drawings and the following description, it should be understood that like numeral markings refer to components having the same function.

[0023] Figure 1A An oxidation reactor 10 with downward flow is shown. Figure 1B is Figure 1A an exploded view of a cross-section. The oxidation reactor 10 can be used to oxidize materials including but not limited to hydrocarbons (e.g., cumene). As Figure 1A shown, an oxidant (e.g., an oxidation gas; an oxygen-containing gas such as air) can be fed into the oxidation reactor 10 via an oxidant line 14 at the top 34 of the oxidation reactor 10. A feed stream 12 comprising hydrocarbons (e.g., cumene and / or CHP) can react with the oxidant in the reactor 10 to obtain a reaction product stream 24. Water can be fed into the reactor 10 at a water line 18 and removed from the reactor 10 at a water line 16.

[0024] The reaction product stream 24 exits at the bottom 36 of the reactor 10. A portion of the reaction product stream 24 can be separated to obtain an off-gas stream 20 and a liquid product stream 22. The liquid product stream 22 can include ethylbenzene, cumene, cumene hydroperoxide, ethylbenzene hydroperoxide, or a combination comprising at least one of the foregoing.

[0025] A portion of the reaction product stream 24 can be recycled to the top 34 of the oxidation reactor 10 via a recycle stream 26. The oxidant fed from the oxidant line 14 can be introduced into an oxidation liquid 28 comprising the recycle stream 26 at the top 34 of the oxidation reactor 10, thereby forming a reaction medium stream 38. As Figure 1B shown, the reaction medium stream 38 comprises the oxidation liquid 28 comprising the recycle stream 26 and / or the feed stream 12, and the reaction medium stream 38 contains an oxidation gas 30 from the oxidant line 14.

[0026] In Figure 1B it, the oxidation liquid 28 and the oxidation gas 30 of the reaction medium stream 38 are shown, wherein the oxidation liquid 28 and the oxidation gas 30 of the reaction medium stream 38 move downward in the reactor 10, as indicated by line 32.

[0027] According to the method disclosed herein, the oxidant / air compression inside the reactor 10 can be isothermal instead of adiabatic (adiabatic compression can occur in a conventional air compressor). This can be achieved by moving the reaction medium stream 38 downward in the reactor 10. By moving the oxidizing liquid 28 of the reaction medium stream 38 downward in the reactor, the linear velocity of the oxidizing liquid 28 of the reaction medium stream 38 can exceed the floating linear velocity of the oxidizing gas 30 relative to, for example, the oxidizing liquid 28 (such as floating bubbles), thereby providing a downward movement of the oxidizing gas 30. At the same time, the hydrostatic pressure of the oxidizing liquid 28 of the reaction medium stream 38 can compress the oxidizing gas 30, thereby making the oxygen pressure higher. Advantageously, the movement of the bubbles of the oxidizing gas 30 and the oxidizing liquid 28 can provide more efficient gas compression. Since the bubbles of the oxidizing gas 30 are in close contact with the oxidizing liquid 28 during this method, the compression becomes isothermal instead of adiabatic, thus significantly reducing the energy consumption. For example, the energy consumption can be reduced by about 50% using the method described herein. In this way, an additional heat exchanger may not be required to maintain the gas at an appropriate temperature. The air compressor can maintain a temperature of 1 bar to 5 bar (100 to 500 kPa) or 2 bar to 6 bar (200 to 600 kPa), which is lower than the temperature of a conventional oxidation reactor. The discharged gas (e.g., oxygen-depleted gas) increases in pressure higher than the inlet, so more energy can be recovered from the discharged gas, contributing to the reduction of energy consumption.

[0028] Therefore, the method for oxidizing hydrocarbons can include feeding an oxidant to the top 34 of the reactor 10. The hydrocarbon can react with the oxidant in the reactor 10 to obtain a reaction product stream 24. The reaction product stream 24 can leave at the bottom 36 of the reactor 10. The outlet pressure of the reactor 10 can exceed the inlet pressure of the reactor 10 by at least 5%.

[0029] A portion of the reaction product stream 24 can be recycled via the recycle stream 26 to the top 34 of the oxidation reactor 10, and the oxidant fed from the oxidant line 14 at the top 34 of the reactor 10 can be introduced into the oxidizing liquid 28 containing the recycle stream 26, thereby forming a reaction medium stream 38. The reaction medium stream 38 can move vertically downward in the reactor 10. The downward linear velocity of the oxidizing liquid 28 can exceed the floating linear velocity of the oxidizing gas 30 relative to, for example, the oxidizing liquid 28 of the reaction medium stream 38. This can provide a downward movement of the oxidant in the reactor 10.

[0030] The present disclosure also provides a method for oxidizing cumene, the method comprising feeding an oxidant to the top 34 of a reactor 10. Cumene may react with the oxidant in the reactor 10 to obtain a reaction product stream 24. The reaction product stream 24 may contain CHP. The reaction product stream 24 may exit at the bottom 36 of the reactor 10. The outlet pressure of the reactor 10 may exceed the inlet pressure of the reactor 10 by at least 5%. The outlet pressure of the reactor 10 may be the pressure at the reactor 10 outlet where the reaction product stream 24 exits the reactor 10 at the bottom 36 of the reactor 10. The inlet pressure of the reactor 10 may be the pressure at the reactor 10 inlet where the reaction medium stream 38 enters the reactor 10 at the top 34 of the reactor 10.

[0031] A portion of the reaction product stream 24 may be recycled via a recycle stream 26 to the top 34 of the reactor 10 to form a reaction medium stream 38. The reaction medium stream 38 may move vertically downward in the reactor 10. The downward linear velocity of the oxidation liquid 28 may exceed the floating linear velocity of the oxidation gas 30 relative to, for example, the oxidation liquid 28, thereby providing a downward movement of the oxidant in the reactor 10.

[0032] The oxidant may include air. The oxidant may be compressed before being fed to the top 34 of the reactor 10. The downward linear velocity of the oxidation liquid 28 of the reaction medium stream 38 may be from 0.2 m / s to 2 m / s, such as from 0.3 m / s to 1 m / s, such as from 0.4 m / s to 0.8 m / s. Still in cumene / CHP, the floating linear velocity of the oxidation gas 30 (e.g., air bubbles) may be from 0.1 m / s to 0.15 m / s.

[0033] The oxidant may be fed to the reactor 10 at an oxidant pressure of less than or equal to 200 kPa (kilopascals), such as less than or equal to 185 kPa, such as less than or equal to 170 kPa. The present disclosure provides that the oxidant (e.g., oxidation gas) may be compressed using a circulating pump power and the operating conditions are close to isothermal. In contrast, it should be noted that using a conventional compressor to compress air, providing an adiabatic efficiency of 75% at 170 kPa requires heating the air to 90 °C; at 185 kPa, the air must be heated to 100 °C; and at 200 kPa, the air must be heated to 110 °C. This requires air cooling before the reactor, which is not desirable. In addition, using a conventional method without downward flow, an air compressor operating under near-adiabatic conditions is used to compress the oxidation gas, thus consuming additional energy.

[0034] The reaction product stream 24 can be separated into a liquid product stream 22 (e.g., containing the reaction medium) and an off-gas stream 20. During the hydrocarbon oxidation process, the liquid product stream 22 can contain ethylbenzene. During the cumene oxidation process, the liquid product stream 22 can contain cumene hydroperoxide, cumene, or a combination containing at least one of the foregoing. The oxidant can include an oxygen-containing gas. The process can include adding hydrogen peroxide, molecular oxygen (dioxygen), ozone, anthraquinone, C 2-32 alkyl peroxides, C 2-32 alkyl hydroperoxides, C 2-32 ketone peroxides, C 2-32 diacyl peroxides, C 3-22 dipers (C 3-22 diperoxy, C 3-22 dioxo, C 3-22 dioxy), ketals, C 2-32 peroxyesters, C 2-32 peroxydicarbonates, C 2-32 peroxyacids, C 6-32 perbenzoic acid, C 2-32 peracids, periodinane, periodates, or a combination containing at least one of the foregoing.

[0035] The reaction of the hydrocarbon with the oxidant in the reactor 10 can be carried out at a temperature of 75 °C to 135 °C, such as 80 °C to 120 °C, such as 85 °C to 115 °C.

[0036] A reaction product can be produced. The reaction product can include phenol, acetone, ethylene, or a combination containing at least one of the foregoing.

[0037] A system for oxidizing a hydrocarbon (e.g., cumene) can include a reactor 10 for reacting the hydrocarbon (e.g., cumene). The reactor 10 can include an oxidant inlet 14 at the top 34 of the reactor 10. The reactor 10 can include a pump fluidly connected to the top 34 and the bottom 36 of the reactor 10 for recirculating a portion of the reaction product stream 24 from the bottom 36 of the reactor 10 to the top 34 of the reactor 10. The reactor 10 can also include a compressor fluidly connected to the oxidant for compressing the oxidant before feeding it to the oxidant inlet 14.

[0038] The reaction product stream 24 exits at the bottom 36 of the reactor 10. A portion of the reaction product stream 24 can be separated to obtain an off-gas stream 20 and a liquid product stream 22. The liquid product stream 22 can include ethylbenzene, cumene, cumene hydroperoxide, ethylbenzene hydroperoxide, or a combination containing at least one of the foregoing.

[0039] The following examples are merely illustrative of the methods and systems disclosed herein and are not intended to limit their scope. Unless otherwise stated, all examples are based on simulations.

[0040] Example

[0041] In the following examples and comparative examples, the energy savings using the methods disclosed herein were calculated assuming the conditions summarized in Table 1. Based on Figure 2 the flow system shown. The production is measured in kilograms per hour (kg / h), the pressure in kilopascals (kPa), the air flow in kg / h, the density in kilograms per cubic meter (kg / m 3 ), the volume in cubic meters per hour (m 3 / h), and the power in kilowatts (kW).

[0042] Figure 2 An example flow system 60 used in the oxidation gas treatment is shown. In Figure 2 it, the fresh air stream 62 is compressed in the compressor 64 and then passes through the intercooler 66 to remove some heat. The fresh air stream 62 consumes electrical power at line 68 and provides compressed air 70 for oxidation. The waste air stream 72 is mixed with the oxidized cumene stream 74 to prepare the oxidized material stream 76. The oxidized material stream 76 is separated into two streams in the tower 78, a first stream 80 and a second stream 82. The first stream 80 may contain waste air saturated with the oxidation product, and the second stream 82 may contain the oxidized material liquid. The first stream 80 may pass through an expander 84 that returns power from the first stream 80 (e.g., the compressed stream) via line 86 providing the waste air stream 88. The waste air stream 88 passes through the cooler 90 to remove some heat from the waste air stream 88. The cold discharge air stream 92 is separated in the separator 94 into a discharge gas stream 96 and a discharge air condensate stream 98. This flow system 60 may allow the estimation of the energy flow in the oxidation system.

[0043]

[0044] * The liquid / gas volume ratio increases as the reaction mixture moves from the top to the bottom of the reactor due to gas compression (the gas volume decreases at the bottom).

[0045] Table 2 shows the material flow data in the cumene oxidation system simulation, while Table 3 shows the energy flow data in the cumene oxidation system simulation. The temperature is measured in degrees Celsius (°C), the pressure in kPa, the molar flow in kilograms - moles per hour (kg·mol / h), the mass flow in kg / h, the cubic meters per hour (m 3The volumetric flow rate (liquid) in units of / h) and the heat flow rate in units of kilojoules per hour (kJ / h). In Table 3, the power is measured in kJ / h, kW, and horsepower (hp). DMBA in Table 2 refers to dimethylbenzyl alcohol.

[0046]

[0047] * In this simulation, 150 hp of power was recovered in the expander 84

[0048] The energy flow of the traditional process without downward flow was calculated with the following operating conditions as a reference: Air to the oxidant was operated at 80,739 kg / h, a temperature of 93 °C, and a pressure of 862 kPa. The oxidation reactor off-gas was operated at 75,378 kg / h, a temperature of 97 °C, and a pressure of 552 kPa. The results are shown in Table 4.

[0049]

[0050] The data in Tables 3 and 4 assume the same off-gas conditions. However, Table 3 provides the results of the method with favorable downward flow described herein, and Table 4 provides the results of the comparative example without downward flow.

[0051] The method with downward flow of the present disclosure operates at a lower reactor pressure because the gas outlet is at the bottom pressure of the reactor. A recycle pump power is used to compress the oxidation gas, and the operating conditions are near isothermal.

[0052] In contrast, in the comparative method without downward flow, an air compressor operating under near adiabatic conditions is used to compress the oxidation gas, thus consuming additional energy. This can be seen in the energy consumed (10,474 hp for the comparative method without downward flow and 5,536 hp for the method of the present disclosure with downward flow), the energy recovered (1,750 hp vs. 2,739 hp), and the total electric power (8,724 hp vs. 3,991 hp), as shown in Tables 3 and 4. As can be seen from Tables 3 and 4, the total electric power (3,991 hp) of the cumene oxidation system including the downward flow reactor design is at least 50% lower than the total electric power (8,724 hp) of the cumene oxidation system including the traditional oxidation reactor design without downward flow. The comparative reactor can be operated at 200 kPa to 500 kPa at the top (reactor outlet) of the reactor and at 400 kPa to 800 kPa, for example 400 kPa to 600 kPa, at the bottom (reactor inlet) of the reactor.

[0053] The methods and systems disclosed herein include at least the following aspects:

[0054] Aspect 1: A method for oxidizing hydrocarbons, the method comprising feeding an oxidant to the top of a reactor; reacting the hydrocarbons with the oxidant in the reactor to obtain a reaction product stream that exits the reactor at a reactor outlet at the bottom of the reactor; recycling a portion of the reaction product stream to the top of the reactor; and introducing the oxidant into an oxidation liquid containing the portion of the reaction product stream recycled to the top of the reactor to form a reaction medium stream entering a reactor inlet at the top of the reactor; wherein the pressure at the reactor outlet exceeds the pressure at the reactor inlet by at least 5%; wherein the reaction medium stream moves vertically downward in the reactor, and wherein the downward linear velocity of the oxidation liquid exceeds the floating linear velocity of the oxidant in the oxidation liquid, thereby providing a downward movement of the oxidant in the reactor.

[0055] Aspect 2: The method according to Aspect 1, wherein the downward linear velocity of the oxidation liquid is from 0.2 m / s to 2 m / s, such as from 0.3 m / s to 1 m / s or from 0.4 m / s to 0.8 m / s.

[0056] Aspect 3: The method according to any one of the preceding aspects, wherein the oxidant is fed to the reactor at an oxidant pressure of less than or equal to 200 kPa, such as less than or equal to 185 kPa or less than or equal to 170 kPa.

[0057] Aspect 4: The method according to any one of the preceding aspects, further comprising compressing the oxidant before feeding the oxidant to the top of the reactor.

[0058] Aspect 5: The method according to any one of the preceding aspects, further comprising separating the reaction product stream to obtain a liquid product stream and an off-gas stream.

[0059] Aspect 6: The method according to Aspect 5, wherein the liquid product stream contains hydrocarbon oxidation products.

[0060] Aspect 7: The method according to Aspect 5, wherein the liquid product stream contains ethylbenzene.

[0061] Aspect 8: The method according to any one of the preceding aspects, wherein the oxidant comprises an oxygen-containing gas.

[0062] Aspect 9: A reaction product produced by the method according to any one of Aspects 1 to 8.

[0063] Aspect 10: A system for oxidizing cumene, the system comprising: a reactor for reacting cumene and an oxidant to obtain a reaction product stream, the reactor including an oxidant inlet at the top of the reactor; and a pump in fluid communication with the top and the bottom of the reactor for recycling a portion of the reaction product stream from the bottom of the reactor to the top of the reactor.

[0064] Aspect 11: The system according to aspect 10 further includes a compressor fluidly connected to the oxidant inlet, which is used to compress the oxidant before feeding the oxidant to the oxidant inlet.

[0065] Aspect 12: A method for oxidizing cumene, the method includes: feeding an oxidant to the top of a reactor; reacting cumene with the oxidant in the reactor to obtain a reaction product stream containing cumene hydroperoxide, the reaction product stream leaving the reactor outlet at the bottom of the reactor; recycling a portion of the reaction product stream to the top of the reactor; and introducing the oxidant into an oxidation liquid containing the portion of the reaction product stream recycled to the top of the reactor to form a reaction medium stream entering the reactor inlet at the top of the reactor; wherein the pressure at the reactor outlet exceeds the pressure at the reactor inlet by at least 5%, and wherein the reaction medium stream moves downward in the reactor.

[0066] Aspect 13: The method according to aspect 12, wherein the oxidant includes air.

[0067] Aspect 14: The method according to aspect 12 or aspect 13, wherein the downward linear velocity of the oxidation liquid exceeds the floating linear velocity of the oxidant in the oxidation liquid, thereby providing a downward movement of the oxidant in the reactor.

[0068] Aspect 15: The method according to aspect 14, wherein the downward linear velocity of the oxidation liquid is from 0.2 m / s to 2 m / s, such as from 0.3 m / s to 1 m / s or from 0.4 m / s to 0.8 m / s.

[0069] Aspect 16: The method according to any one of aspects 12 to 15, wherein the oxidant is fed to the reactor at an oxidant pressure less than or equal to 200 kPa, such as less than or equal to 185 kPa or less than or equal to 170 kPa.

[0070] Aspect 17: The method according to any one of aspects 12 to 16 further includes compressing the oxidant before feeding the oxidant to the top of the reactor.

[0071] Aspect 18: The method according to any one of aspects 12 to 17 further includes separating the reaction product stream to obtain a liquid product stream and an exhaust gas stream.

[0072] Aspect 19: The method according to aspect 18, wherein the liquid product stream contains cumene hydroperoxide, cumene, or a combination containing at least one of the foregoing.

[0073] Aspect 20: The method according to any one of aspects 12 to 19, wherein the reaction is carried out at a temperature of 75 °C to 135 °C, such as 80 °C to 120 °C or 85 °C to 115 °C.

[0074] Generally, the present invention may alternatively comprise, consist of, or consist essentially of any suitable components disclosed herein. The present invention may additionally or alternatively be formulated so as to be free or substantially free of any components, materials, ingredients, adjuvants or substances used in the prior art compositions or otherwise not necessary to achieve the functions and / or objectives of the present invention. All endpoints of ranges for the same component or property are included and can be combined independently (e.g., a range of "less than or equal to 25 wt%, or 5 wt% to 20 wt%" includes the endpoints and all intermediate values of the range of "5 wt% to 25 wt%", etc.). Disclosure of a narrower range or a more specific group in addition to a broader range does not disclaim the broader range or larger group. "Combination" includes blends, mixtures, alloys, reaction products, etc. Further, the terms "first", "second", etc. herein do not denote any order, quantity or importance, but are used to denote one element from another. Unless otherwise stated herein or clearly contradicted by the context, the terms "a", "an" and "the" herein do not denote a limitation of quantity, but are to be construed as covering both the singular and the plural. "Or" means "and / or". As used herein, the suffix "(s)" is intended to include both the singular and the plural of the term it modifies, thus including one or more of that term (e.g., film(s) includes one or more films). Reference throughout the specification to "one embodiment", "another embodiment", "an embodiment", etc. means that a particular element (e.g., a feature, structure, and / or characteristic) described in connection with the embodiment is included in at least one embodiment described herein, and may or may not be present in other embodiments. Further, it should be understood that the described elements may be combined in any suitable manner in various embodiments.

[0075] The modifier "about" used in connection with a quantity includes the recited value and has the meaning specified by the context (e.g., it includes the degree of error associated with a particular quantity of measurement). The symbol " + 10%" means that the indicated measurement can be a quantity that is 10% less to 10% more than the specified value. Unless otherwise indicated, the terms "front", "rear", "bottom" and / or "top" as used herein are for descriptive convenience only and are not limited to any one position or spatial orientation. "Optional" or "optionally" means that the subsequent described event or circumstance may or may not occur, and the description includes both the instance where the event occurs and the instance where it does not. Unless otherwise defined, the technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. "Combination" includes blends, mixtures, alloys, reaction products, etc.

[0076] All cited patents, patent applications, and other references are incorporated herein by reference in their entirety. However, if a term in the present application contradicts or conflicts with a term in the incorporated reference, the term from the present application takes precedence over the conflicting term from the incorporated reference.

[0077] Although specific embodiments have been described, the applicant or other persons skilled in the art may conceive of substitutions, modifications, variations, improvements, and substantial equivalents that are not currently foreseeable or may not be foreseeable. Therefore, the appended claims as filed and as they may be amended are intended to cover all such substitutions, modifications, variations, improvements, and substantial equivalents.

Claims

1. A method for oxidizing cumene, comprising: Feeding an oxidant to the top of a reactor; Reacting the cumene with the oxidant in the reactor to obtain a reaction product stream, the reaction product stream exiting the reactor at a reactor outlet at the bottom of the reactor; Separating the reaction product stream to obtain an off-gas stream and a liquid product stream; Recycling a portion of the liquid product stream to the top of the reactor; And Introducing the oxidant into an oxidation liquid containing the portion of the liquid product stream recycled to the top of the reactor to form a reaction medium stream entering a reactor inlet at the top of the reactor; Wherein the pressure at the reactor outlet exceeds the pressure at the reactor inlet by at least 5%; Wherein the reaction medium stream freely moves vertically downward from the top of the reactor to the bottom of the reactor in the reactor; and Wherein the downward linear velocity of the oxidation liquid exceeds the floating linear velocity of the oxidant in the oxidation liquid, thereby providing a downward movement of the oxidant and providing compression of the oxidant using the hydrostatic pressure of the oxidation liquid.

2. The method according to claim 1, wherein The reaction product stream contains cumene hydroperoxide.

3. The method according to claim 1, wherein The downward linear velocity of the oxidation liquid is from 0.2 m / s to 2 m / s.

4. The method according to claim 1, wherein The oxidant is fed to the reactor at an oxidant pressure less than or equal to 200 kPa.

5. The method according to claim 1, further comprising compressing the oxidant before feeding the oxidant to the top of the reactor.

6. The method according to claim 1, wherein The liquid product stream contains cumene oxidation products.

7. The method according to claim 1, wherein, The liquid product stream contains cumene hydroperoxide, cumene, or a combination containing at least one of the foregoing.

8. The method according to claim 1, wherein The oxidant includes an oxygen-containing gas.

9. The method according to claim 8, wherein The oxidant includes air.

10. The method according to claim 1, wherein The reaction is carried out at a temperature of 75°C to 135°C.

11. A system for oxidizing cumene, comprising: A reactor for reacting the cumene with an oxidant to obtain a reaction product stream, the reactor including an oxidant inlet at the top of the reactor; And A pump in fluid communication with the top and the bottom of the reactor for recycling a portion of the reaction product stream from the bottom of the reactor to the top of the reactor; Wherein the system is configured to (i) introduce the oxidant into an oxidation liquid containing the portion of the reaction product stream recycled to the top of the reactor to form a reaction medium stream entering a reactor inlet at the top of the reactor, and (ii) cause the oxidation liquid of the reaction medium stream to freely move downward in the reactor at a linear velocity that exceeds the floating linear velocity of the oxidant relative to the oxidation liquid, thereby providing a downward movement of the oxidant and providing compression of the oxidant using the hydrostatic pressure of the oxidation liquid.

12. The system according to claim 11, further comprising a compressor in fluid communication with the oxidant inlet, the compressor being configured to compress the oxidant before feeding the oxidant to the oxidant inlet.

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