Integrated process for production of bisphenol A

Abstract

An integrated process for the production of bisphenol A, the process comprising separating a first stream comprising acetone and phenol to provide a second stream comprising acetone and a third stream comprising phenol; and reacting acetone present in the second stream and phenol present in the third stream to produce a product stream comprising bisphenol A and a recycle stream.

Description

BACKGROUND

[0001] Polycarbonates are widely used in various applications due to their good balance of properties including moldability, impact resistance, and transparency. Polycarbonates can be obtained by reacting a carbonate source with bisphenol A (BPA).

[0002] There is interest in improved methods and systems for producing BPA.

[0003] The processes, methods, and systems of the present disclosure address opportunities for improvement. SUMMARY

[0004] The present disclosure provides advantageous integrated methods and systems for producing BPA.

[0005] Disclosed herein is an integrated method for producing bisphenol A, the method comprising: separating a first stream comprising acetone and phenol to provide a second stream comprising acetone and a third stream comprising phenol; and reacting acetone present in the second stream and phenol present in the third stream to produce a product stream comprising bisphenol A and a recycle stream.

[0006] Also disclosed herein is an integrated method for producing bisphenol A, the method comprising: reacting benzene and acetone to produce cumene; oxidizing cumene to produce cumene hydroperoxide; cleaving cumene hydroperoxide to produce a first stream comprising acetone, phenol, and a-methylstyrene; separating the first stream to provide a second stream comprising acetone and a third stream comprising phenol; cracking hydrocarbon compounds present in the third stream to produce a cracked hydrocarbon stream comprising phenol; purifying the second stream to provide a purified second stream comprising a greater proportion of acetone than the second stream; purifying the third stream to provide a purified third stream comprising a greater proportion of phenol than the third stream; and reacting acetone present in the purified second stream and phenol present in the purified third stream to produce a product stream comprising bisphenol A and a recycle stream; wherein the recycle stream comprises acetone; wherein separating the first stream to provide the second stream and the third stream comprises: separating the cracked hydrocarbon stream to provide the second stream and the third stream; and wherein reacting acetone present in the purified second stream and phenol present in the purified third stream to produce the product stream comprises: reacting at least a portion of the acetone present in the recycle stream to produce the product stream.

[0007] Further disclosed herein is an integrated system for producing bisphenol A, the system comprising: a first column for separating a first stream to provide a second stream comprising acetone and a third stream comprising phenol; a reactor for reacting acetone present in the second stream and phenol present in the third stream to produce a product stream comprising bisphenol A and a recycle stream; and a recycle line for recycling the recycle stream to the first column.

[0008] The above-described and other features are exemplified by the following figures and detailed description.

[0009] Embodiments in any combination or permutation are contemplated. Additional advantageous features, functions, and applications of the disclosed processes, methods, and systems of the present disclosure will be apparent from the description that follows, particularly when read in conjunction with the drawings. All references listed in the present disclosure are incorporated by reference in their entirety. BRIEF DESCRIPTION OF DRAWINGS

[0010] The following drawings are of example embodiments in which like numerals designate like elements.

[0011] Figure 1 is a block flow diagram of an embodiment;

[0012] Figure 2 is a process flow diagram of an embodiment;

[0013] Figure 3 is a process flow diagram of an embodiment;

[0014] Figure 4 is a process flow diagram of an embodiment;

[0015] Figure 5 is a process flow diagram of an embodiment;

[0016] Figure 6 is a process flow diagram of an embodiment;

[0017] Figure 7 is a process flow diagram of an embodiment;

[0018] Figure 8 is a process flow diagram of an embodiment;

[0019] Figure 9 is a process flow diagram of an embodiment; and

[0020] Figure 10 is a process flow diagram of an embodiment. DETAILED DESCRIPTION

[0021] The exemplary embodiments disclosed herein illustrate advantageous integrated processes and systems for producing bisphenol A. However, it is to be understood that the disclosed embodiments are merely examples of the present disclosure, which can be embodied in various forms. Accordingly, the details disclosed herein in connection with exemplary processes and related systems for producing bisphenol A are not intended to limit, but rather to provide an appreciation of the advantageous processes for producing bisphenol A that would be taught to one skilled in the art.

[0022] The present disclosure provides advantageous integrated processes for producing bisphenol A, and improved systems for utilizing these processes.

[0023] More particularly, the present disclosure provides advantageous integrated processes for producing bisphenol A that provide cost efficiency compared to producing BPA and phenol separately.

[0024] For example, an integrated process for producing BPA is provided. Phenol from phenol production can be used in BPA production, and unreacted phenol from BPA production can be recycled to phenol production. More specifically, phenol separated in a distillation column of phenol production can be used in BPA production, and unreacted phenol from BPA production can be recycled to the distillation column of phenol production.

[0025] The integrated process avoids the need for separate systems for purifying phenol in each of phenol production and BPA production. In one embodiment, phenol from phenol production can be used in more than one BPA production reactor.

[0026] Figure 1 is a block flow diagram of an embodiment. Energy integration (e.g., in the form of steam) can be provided between cumene production 1000 and phenol production 2000. A stream 3000 comprising purified phenol and a stream 4000 comprising purified acetone can be provided from phenol production 2000 to BPA production 5000. A stream 6000 comprising unreacted phenol and a stream 7000 comprising byproducts (e.g., heavies) from BPA production 5000 can be recycled to phenol production 2000. A product stream 8000 comprising BPA 8000 from BPA production 5000 can be used in polycarbonate production 9000.

[0027] Recycling a stream comprising unreacted phenol from BPA production to phenol production can provide a high purity BPA product, increased process yield, efficient disposal of unreacted phenol, or a combination thereof. While greater recycling can provide a higher purity BPA product, increasing the amount of recycling can not be financially desirable. For example, additional energy (steam) can be used for distillation (purification) of the recycled stream to provide a higher purity BPA product.

[0028] The stream recovered from BPA production comprising unreacted phenol can have a lower quality than the stream comprising phenol introduced into the BPA production, e.g., have a lower purity of BPA. The feedstock, e.g., phenol used in the BPA production, can be used efficiently because the unreacted phenol recovered from the BPA production can be used in the BPA production. The separation of phenol and byproducts from the BPA production in the phenol production and for use in the BPA production can be achieved in a single step or unit, e.g., a distillation column.

[0029] Reference Figure 2 In one embodiment, the first stream 10 can comprise 8-12 wt% water, 25-28.5 wt% acetone, 8-12 wt% cumene, 46-49 wt% phenol, and 0.35-0.65 wt% alkylated heavies, e.g., 9.5-10.5 wt% water, 26-26.5 wt% acetone, 9-9.5 wt% cumene, 46.7-47.4 wt% phenol, and 0.45-0.55 wt% alkylated heavies. The amount of water can be set by equilibrium; when the amount of cumene is higher, the amount of water can be lower, and vice versa, when the amount of cumene is lower, the amount of water can be higher. As used herein, “alkylated heavies” refers to the products of side reactions with phenol and can include, for example, p-cumyl phenol, o-cumyl phenol, 2-methylbenzofuran, a-methyl styrene dimer 1, a-methyl styrene dimer 2, cyclic a-methyl styrene dimer, and p,p-bisphenol A.

[0030] In one embodiment, the first stream 10 can comprise 8-12 wt% water, 25-28.5 wt% acetone, 8-12 wt% cumene, 46-49 wt% phenol, and 0.35-0.65 wt% alkylated heavies, e.g., 9.5-10.5 wt% water, 26-26.5 wt% acetone, 9-9.5 wt% cumene, 46.7-47.4 wt% phenol, and 0.45-0.55 wt% alkylated heavies. The amount of water can be set by equilibrium; when the amount of cumene is higher, the amount of water can be lower, and vice versa, when the amount of cumene is lower, the amount of water can be higher. As used herein, “alkylated heavies” refers to the products of side reactions with phenol and can include, for example, p-cumyl phenol, o-cumyl phenol, 2-methylbenzofuran, a-methyl styrene dimer 1, a-methyl styrene dimer 2, cyclic a-methyl styrene dimer, and p,p-bisphenol A.

[0031] The processing conditions for Tower 100 can include temperatures of 180 to 410°F (82 to 210°C), gauge pressures of 2 to 12.5 pounds per square inch (psi) (13,790 to 86,184 Pascals (Pa)) and flow rates of 350 to 470 gallons per minute (GPM) (1,325 to 1,779 liters per minute (LPM)), such as 190 to 397°F (88 to 203°C), 3 to 11.5 psi (20,684 to 79,290 Pa), and 380 to 420 GPM (1,438 to 1,590 LPM).

[0032] In one embodiment, the second stream 20 may include 0.25 to 0.50 wt% water, 99.5 to 99.75 wt% acetone, 0 to 10 parts per million (ppm) cumene, 0 ppm phenol, and 0 ppm alkylated heavy material, such as 0.35 to 0.40 wt% water, 99.55 to 99.65 wt% acetone, 0 to 2 ppm cumene, 0 ppm phenol, and 0 ppm alkylated heavy material.

[0033] In one embodiment, the third stream 30 may include 0 to 300 ppm water, 0 to 0.35 ppm acetone, 0 to 0.2 ppm cumene, 99.5 to 99.95 wt% phenol, and 0 to 0.1 ppm alkylated heavy material, such as 50 to 150 ppm water, 0.20 to 0.25 wt% acetone, 0.15 to 0.20 wt% cumene, 99.6 to 99.65 wt% phenol, and 0 ppm alkylated heavy material.

[0034] In one embodiment, the recycled stream 50 may include 0 to 0.5 wt% water, 0 to 0.4 wt% acetone, 0 to 10 ppm cumene, 75 to 90 wt% phenol, and 10 to 25 wt% alkylated heavy material, such as 0 to 0.3 wt% water, 0 to 0.3 wt% acetone, 3 to 5 ppm cumene, 80 to 90 wt% phenol, and 15 to 20 wt% alkylated heavy material.

[0035] The processing conditions of the BPA production reactor 200 may include a temperature of 130 to 185°F (54 to 85°C), a gauge pressure of 0 to 25 psi (0 to 172,369 Pa), and a flow rate of 100 to 200 GPM (379 to 757 LPM), such as 135 to 175°F (57 to 79°C), 0 to 10 psi (0 to 68,948 Pa), and 110 to 140 GPM (416 to 530 LPM).

[0036] In one embodiment, product stream 40 may include 99.5 to 99.98 wt% BPA, for example, 99.8 wt% to wt% BPA. In one embodiment, product stream 40 may have an American Public Health Association (APHA) solution color of less than 20 to less than 2 parts per million platinum-cobalt ratio to water. The purity of product stream 40 may be affected by factors such as the number of trays in column 100, flow rate and reflux in column 100, catalyst freshness, and reflux in BPA production reactor 200.

[0037] refer to Figure 3 The method may further include combining the first stream 10 and the recycled stream 50 to provide a combined stream 60, and separating the first stream 10 to provide a second stream 20 and a third stream 30 may include separating the combined stream 60 to provide the second stream 20 and the third stream 30. In one embodiment, the combined stream 60 may be fed into a tank before being fed into the tower 100. Water may be decanted from the combined stream 50 in the tank. In one embodiment, the first stream 10 may be fed into a tank, from which water may be decanted, and the recycled stream 50 may be combined with the stream leaving the tank to provide the combined stream 60 fed into the tower 100.

[0038] In one embodiment, the combined stream 60 may include 8 to 12 wt% water, 26 to 28.5 wt% acetone, 8 to 12 wt% cumene, 26 to 48 wt% phenol, and 0.45 to 0.66 wt% alkylated heavy material, such as 9.5 to 10.5 wt% water, 26 to 26.5 wt% acetone, 9 to 9.5 wt% cumene, 46.7 to 47.4 wt% phenol, and 0.45 to 0.65 wt% alkylated heavy material.

[0039] This method may include adjusting the composition of the combined stream 60 before separating it to provide the second stream 20 and the third stream 30. Adjusting the composition of the combined stream 60 may include, for example, adjusting the amount, such as the flow rate, of the recycle stream 50. As the flow rate of the recycle stream 50 increases, the purity of the product stream 40 may increase. Increasing the flow rate of the recycle stream will result in an increased cost of more steam for distillation of the combined stream.

[0040] refer to Figure 4 The method may also include mixing the recycled stream 50 with the second stream 20. (See reference) Figure 5 The method may further include purifying the second stream 20 in a first purifier 300 to produce purified second stream 25 before reacting acetone present in the second stream 20 and phenol present in the third stream 30 to produce product stream 40 including bisphenol A.

[0041] The processing conditions of the first purifier 300 may include a temperature of 130 to 170°F (54 to 77°C), a gauge pressure of 0 to 21.2 psi (0 to 146,169 Pa), and a flow rate of 150 to 300 GPM (568 to 1,136 LPM), for example, 130 to 170°F (54 to 77°C), 0 to 21.2 psi (0 to 146,169 Pa), and 250 to 275 GPM (946 to 1,041 LPM).

[0042] In one embodiment, the purified second stream 25 may include 15 to 20 wt% water, 53 to 56 wt% acetone, 22 to 25 wt% cumene, 0.1 to 1.5 wt% phenol, and 0 to 0.01 wt% alkylated heavy material, such as 17 to 15.2 wt% water, 54 to 55.2 wt% acetone, 23 to 24 wt% cumene, 0.2 to 0.5 wt% phenol, and 0 to 0.1 wt% alkylated heavy material.

[0043] refer to Figure 6 The method may further include purifying the third stream 30 in a second purifier 400 to produce purified third stream 35 before reacting acetone present in the second stream 20 and phenol present in the third stream 30 to produce product stream 40 including bisphenol A.

[0044] The processing conditions of the second purifier 400 may include a temperature of 290 to 425°F (143 to 218°C), a gauge pressure of 0 to 1,260 mmHg (0 to 167,986 Pa), and a flow rate of 130 to 250 GPM (492 to 946 LPM), for example, 290 to 425°F (143 to 218°C), 0 to 1,260 mmHg (0 to 167,986 Pa), and 200 to 225 GPM (757 to 852 LPM).

[0045] The purified third-party product specification 35 may include, for example, up to 30 ppm 2-methylbenzofuran, 5 ppm hydroxyacetone, 0.1 ppm iron, 5 ppm isopropyl acetone, 20 ppm carbonyl compounds, >80 ppm organic impurities such as cresol, 0.03 wt% water, 5 ppm 10α-methylstyrene, 20 ppm m-cresol and p-cresol, 75 ppm o-cresol, or combinations thereof.

[0046] The purity of the purified third stream 35 can be affected by factors such as the number of trays in column 100, flow rate, reflux and flow rate in column 100, catalyst freshness, and reflux in the second purifier 400.

[0047] The method may further include reacting benzene and acetone to produce cumene; oxidizing the cumene to produce cumene hydrogen peroxide; and breaking the cumene hydrogen peroxide to produce a first stream 10, wherein the first stream 10 may further contain α-methylstyrene.

[0048] refer to Figure 7 The method may further include pyrolyzing hydrocarbon compounds present in the third stream 30 in a pyrolyzer 500 to produce a pyrolyzed hydrocarbon stream, at least a portion of which is recycled back to the method as stream 70. The pyrolyzed hydrocarbon stream 70 may contain phenol. Separating the first stream 10 to provide the second stream 20 and the third stream 30 may include separating stream 70 to provide the second stream 20 and the third stream 30.

[0049] Third stream 30 may contain impurities related to both BPA and phenol production. Purification of third stream 30 can produce not only purified third stream 35, but also streams containing impurities such as hydrocarbon compounds. Cracking such hydrocarbon compounds can improve yields at high purity.

[0050] Processing conditions for the pyrolyzer 500 may include a temperature of 400 to 630°F (204 to 332°C), a gauge pressure of 0 to 15 psi (0 to 103,421 Pa), and a flow rate of 5 to 25 GPM (19 to 95 LPM), for example, 500 to 600°F (260 to 316°C), 7.5 to 15 psi (51,711 to 103,421 Pa), and 18 to 23 GPM (68 to 87 LPM).

[0051] In one embodiment, the stream 70 may include 0 wt% water, 0 wt% acetone, 20 to 25 wt% cumene, 30 to 36 wt% phenol, and 0 to 0.1 wt% alkylated heavy material, such as 0 wt% water, 0 wt% acetone, 22.5 to 23 wt% cumene, 33.2 to 34.2 wt% phenol, and 0 to 0.1 wt% alkylated heavy material.

[0052] In one embodiment, the stream fed into the pyrolyzer 500 may include 0 wt% water, 0 wt% acetone, 0 wt% cumene, 0.5 to 3.0 wt% phenol, and 60 to 70 wt% alkylated heavy material, such as 0 wt% water, 0 wt% acetone, 0 wt% cumene, 0.8 to 1.2 wt% phenol, and 63 to 67 wt% alkylated heavy material.

[0053] refer to Figure 8In one embodiment, the method may include purifying the second stream 20 in a first purifier 300 to produce purified second stream 25 before reacting acetone present in the second stream 20 and phenol present in the third stream 30 to produce product stream 40 containing bisphenol A, and purifying the third stream 30 in a second purifier 400 to produce purified third stream 35 before reacting acetone present in the second stream 20 and phenol present in the third stream 30 to produce product stream 40 containing bisphenol A.

[0054] refer to Figure 9 In one embodiment, an integrated method for producing bisphenol A includes reacting benzene and acetone in an isopropylbenzene production reactor 800 to produce isopropylbenzene; oxidizing the isopropylbenzene in an isopropylbenzene oxidation reactor 900 to produce isopropylbenzene hydrogen peroxide; breaking the isopropylbenzene hydrogen peroxide in a cleavage reactor 950 to produce a first stream 10 comprising acetone, phenol, and α-methylstyrene; separating the first stream 10 to provide a second stream 20 comprising acetone and a third stream 30 comprising phenol; cleaving the hydrocarbon compound present in the third stream 30 in a cleavage reactor 500 to produce a cleaved hydrocarbon stream 70 comprising phenol; purifying the second stream 20 to provide a purified second stream 25 comprising a larger proportion of acetone than the second stream 20; providing a purified third stream 35 comprising a larger proportion of phenol than the third stream 30 after purifying the third stream 30; and reacting the acetone present in the purified second stream 25 and the phenol present in the purified third stream 35 to produce a product stream 40 comprising bisphenol A and a recycled stream 50 comprising acetone. Separating the first stream 10 to provide the second stream 20 and the third stream 30 may include separating the cracked hydrocarbon stream 70 to provide the second stream 20 and the third stream 30. Reacting acetone present in the purified second stream 25 and phenol present in the purified third stream 35 to produce the product stream 40 may include reacting at least a portion of the acetone present in the recycled stream 50 to produce the product stream.

[0055] The purification of the third stream 30 can produce not only purified third stream 35, but also streams containing hydrocarbon compound impurities. Such hydrocarbon compounds are cracked in cracker 500 to produce cracked hydrocarbon stream 70 containing phenol.

[0056] Processing conditions for the cumene oxidation reactor 900 may include a temperature of 175 to 220°F (79 to 104°C), a gauge pressure of 70 to 85 psi (482,633 to 586,054 Pa), and a flow rate of 1,000 to 1,400 GPM (3,785 to 5,300 LPM), for example, 175 to 220°F (79 to 104°C), 70 to 85 psi (482,633 to 586,054 Pa), and 1,100 to 1,200 GPM (4,164 to 4,542 LPM).

[0057] Processing conditions for the fracture reactor 950 may include a temperature of 80 to 110°F (27 to 43°C), a gauge pressure of 0 to 19.7 psi (0 to 135,827 Pa), and a flow rate of 225 to 400 GPM (852 to 1,514 LPM), for example, 85 to 105°F (29 to 41°C), 0 to 19.7 psi (0 to 135,827 Pa), and 350 to 380 GPM (1,325 to 1,438 LPM).

[0058] refer to Figure 10 Reacting acetone present in the second stream 20 and phenol present in the third stream 30 to produce product stream 40 may include: reacting acetone present in the second stream 20 and phenol present in the third stream 30 in a first BPA production reactor 600 to produce a first product stream 80 and a first recycle stream 85 containing bisphenol A; and reacting acetone present in the second stream 20 and phenol present in the third stream 30 in a second BPA production reactor 700 to produce a second product stream 90 and a second recycle stream 95 containing bisphenol A. Reacting at least a portion of acetone present in the recycle stream 50 to produce product stream 40 may include: reacting acetone present in the first recycle stream 85 to produce a product stream, and reacting acetone present in the second recycle stream 95 to produce a product stream.

[0059] Processing conditions for the first BPA production reactor 600 may include a temperature of 130 to 185°F (54 to 85°C), a gauge pressure of 0 to 25 psi (0 to 172,369 Pa), and a flow rate of 100 to 200 GPM (379 to 757 LPM), such as 135 to 175°F (57 to 79°C), 0 to 10 psi (0 to 68,948 Pa), and 110 to 140 GPM (416 to 530 LPM).

[0060] Processing conditions for the second BPA production reactor 700 may include a temperature of 130 to 185°F (54 to 85°C), a gauge pressure of 0 to 25 psi (0 to 172,369 Pa), and a flow rate of 100 to 200 GPM (379 to 757 LPM), such as 135-175°F (57-79°C), 0-10 psi (0-68,948 Pa), and 110-140 GPM (416-530 LPM).

[0061] In one embodiment, the first product stream 80 may include 99.7-99.98 wt% BPA, 0-250 ppm phenol and 0.02-0.3 wt% heavy matter, such as 99.8-99.9 wt% BPA, 100-200 ppm phenol and 0.09-0.18 wt% heavy matter.

[0062] In one embodiment, the first recycle stream 85 may include 0-0.5 wt% water, 0-0.4 wt% acetone, 0-10 ppm cumene, 75-90 wt% phenol, and 5-20 wt% alkylated heavy material, for example, 0-0.3 wt% water, 0-0.3 wt% acetone, 3-5 ppm cumene, 80-90 wt% phenol, and 10-15 wt% alkylated heavy material. In one embodiment, the first recycle stream 85 has less heavy material than recycle stream 50.

[0063] In one embodiment, the second product stream 90 may include 99.5 wt% to 99.98 wt% BPA, for example, 99.8 wt% BPA.

[0064] In one embodiment, the second recycle stream 95 may include 0-0.5 wt% water, 0-0.4 wt% acetone, 0-10 ppm cumene, 75-90 wt% phenol, and 10-25 wt% alkylated heavy material, for example, 0-0.3 wt% water, 0-0.3 wt% acetone, 3-5 ppm cumene, 80-90 wt% phenol, and 15-20 wt% alkylated heavy material. In one embodiment, the second recycle stream 95 may have the same composition as recycle stream 50.

[0065] Reacting acetone present in second stream 20 and phenol present in third stream 30 to produce product stream 40 may include: reacting acetone present in second stream 20 and phenol present in third stream 30 in a first BPA production reactor 600 to produce a first product stream 80 and a first recycling stream 85 containing bisphenol A; and reacting acetone present in second stream 20 and phenol present in third stream 30 in a second BPA production reactor 700 to produce a second product stream 90 and a second recycling stream 95 containing bisphenol A. The method may further include reacting phenol present in the first recycling stream 85 (indicated by dashed lines) with acetone present in second stream 20 and phenol present in third stream 30 in the second BPA production reactor 700 to produce a second product stream 90 and a second recycling stream 95 containing bisphenol A. The weight percentage of bisphenol A present in the first product stream 80 based on the total weight of the first product stream 80 may be greater than the weight percentage of bisphenol A present in the second product stream 90 based on the total weight of the second product stream 90.

[0066] In one embodiment, the integrated system for producing bisphenol A includes: a tower 100 for separating a first stream 10 to provide a second stream 20 containing acetone and a third stream 30 containing phenol; a reactor 200 for reacting the acetone present in the second stream 20 and the phenol present in the third stream 30 to produce a product stream 40 containing bisphenol A and a recirculation stream 50; and a recirculation line for recirculating the recirculation stream 50 back to the tower 100.

[0067] Reactor 200 for reacting acetone present in second stream 20 and phenol present in third stream 30 to produce product stream 40 may include: a first reactor 600 for reacting acetone present in second stream 20 and phenol present in third stream 30 to produce a first product stream 80 containing bisphenol A and a first recycle stream 85; and a second reactor 700 for reacting acetone present in second stream 20 and phenol present in third stream 30 to produce a second product stream 90 containing bisphenol A and a second recycle stream 95.

[0068] This disclosure is further illustrated by the following non-limiting embodiments.

[0069] Example

[0070] according to Figure 9 The method shown was performed using Aspen V10 simulation software to simulate the BPA unit. The recirculated stream 50 was set to 5% of the total dry mother liquor flow rate. Details are provided in Tables 1 and 2.

[0071] Table 1

[0072]

[0073] Table 2

[0074]

[0075] This disclosure also covers the following aspects.

[0076] Aspect 1. An integrated method for producing bisphenol A, the method comprising: separating a first stream containing acetone and phenol to provide a second stream containing acetone and a third stream containing phenol; and reacting the acetone present in the second stream and the phenol present in the third stream to produce a product stream containing bisphenol A and a recycling stream.

[0077] Aspect 2. The method of Aspect 1, wherein: the recycled stream contains acetone; and reacting the acetone present in the second stream and the phenol present in the third stream to produce the product stream comprises: reacting at least a portion of the acetone present in the recycled stream to produce the product stream.

[0078] Aspect 3. The method of aspect 1 or 2 further includes merging the first logistics and the recycling flow to provide a merged logistics, wherein separating the first logistics to provide the second and third logistics includes: separating the merged logistics to provide the second and third logistics.

[0079] Aspect 4. The method of aspect 3 also includes adjusting the composition of the combined logistics before separating and merging the logistics to provide the second and third logistics.

[0080] Aspect 5. The method of any of the preceding aspects further includes purifying the second stream before reacting acetone present in the second stream with phenol present in the third stream to produce a product stream containing bisphenol A.

[0081] Aspect 6. The method of any of the preceding aspects further includes purifying the third stream before reacting acetone present in the second stream with phenol present in the third stream to produce a product stream containing bisphenol A.

[0082] Aspect 7. The method of any of the preceding aspects further includes: reacting benzene and acetone to produce cumene; oxidizing cumene to produce cumene hydrogen peroxide; and cleaving cumene hydrogen peroxide to produce a first stream, wherein the first stream further comprises α-methylstyrene.

[0083] Aspect 8. The method of any of the preceding aspects further includes cracking hydrocarbon compounds present in the third stream.

[0084] Aspect 9. The method of aspect 8, wherein the hydrocarbon compounds present in the cracked third stream produce a cracked hydrocarbon stream containing phenol.

[0085] Aspect 10. The method of aspect 9, wherein separating the first stream to provide the second and third streams comprises: separating the cracked hydrocarbon stream to provide the second and third streams.

[0086] Aspect 11. The method of Aspect 2, wherein: reacting acetone present in the second stream and phenol present in the third stream to produce a product stream comprises: reacting acetone present in the second stream and phenol present in the third stream in a first reactor to produce a first product stream and a first recycled stream containing bisphenol A, and reacting acetone present in the second stream and phenol present in the third stream in a second reactor to produce a second product stream and a second recycled stream containing bisphenol A; and reacting acetone present in the recycled stream to produce a product stream comprises: reacting acetone present in the first recycled stream to produce a product stream, and reacting acetone present in the second recycled stream to produce a product stream.

[0087] Aspect 12. The method of any one of Aspects 1 to 10, wherein reacting acetone present in the second stream and phenol present in the third stream to produce a product stream comprises: reacting acetone present in the second stream and phenol present in the third stream in a first reactor to produce a first product stream and a first recycle stream containing bisphenol A; and reacting acetone present in the second stream and phenol present in the third stream in a second reactor to produce a second product stream and a second recycle stream containing bisphenol A; and the method further comprises reacting phenol present in the first recycle stream with acetone present in the second stream and phenol present in the third stream in the second reactor to produce a second product stream and a second recycle stream containing bisphenol A, wherein the weight percentage of bisphenol A present in the first product stream based on the total weight of the first product stream is greater than the weight percentage of bisphenol A present in the second product stream based on the total weight of the second product stream.

[0088] Aspect 13. An integrated method for producing bisphenol A, the method comprising: reacting benzene and acetone to produce cumene; oxidizing the cumene to produce cumene hydrogen peroxide; cleaving the cumene hydrogen peroxide to produce a first stream comprising acetone, phenol, and α-methylstyrene; separating the first stream to provide a second stream comprising acetone and a third stream comprising phenol; cleaving a hydrocarbon compound present in the third stream to produce a cleaved hydrocarbon stream comprising phenol; purifying the second stream to provide a purified second stream comprising a greater proportion of acetone than the second stream; and providing a purified second stream comprising a greater proportion of acetone than the third stream after purifying the third stream. Example: a purified third stream of phenol; and reacting acetone present in a purified second stream and phenol present in a purified third stream to produce a product stream containing bisphenol A and a recycled stream; wherein the recycled stream contains acetone; wherein separating the first stream to provide the second and third streams includes: separating a cracked hydrocarbon stream to provide the second and third streams; and wherein reacting acetone present in a purified second stream and phenol present in a purified third stream to produce the product stream includes: reacting at least a portion of the acetone present in the recycled stream to produce the product stream.

[0089] Aspect 14. An integrated system for producing bisphenol A, comprising: a first column for separating a first stream to provide a second stream containing acetone and a third stream containing phenol; a reactor for reacting acetone present in the second stream and phenol present in the third stream to produce a product stream containing bisphenol A and a recirculation stream; and a recirculation line for recirculating the recirculation stream back to the first column.

[0090] Aspect 15. An integrated system of aspect 14, wherein the reactor for reacting acetone present in a second stream and phenol present in a third stream to produce a product stream comprises: a first reactor for reacting acetone present in the second stream and phenol present in the third stream to produce a first product stream and a first recycle stream containing bisphenol A; and a second reactor for reacting acetone present in the second stream and phenol present in the third stream to produce a second product stream and a second recycle stream containing bisphenol A.

[0091] Methods and systems may alternatively include, consist of, or substantially consist of any suitable materials, steps, or components disclosed herein. Methods and systems may also be formulated to be free of or substantially free of any materials (or classes of things), steps, or components that are not essential for achieving the function or purpose of the methods and systems.

[0092] All scopes disclosed herein include endpoints, and endpoints are combined independently of each other (e.g., the scope of "up to 25 wt%, or more specifically 5 wt% to 20 wt%" includes the endpoints of the scope of "5 wt% to 25 wt%" and all intermediate values, etc.). "Combination" includes blends, mixtures, alloys, reaction products, etc. The terms "first," "second," etc., do not indicate any order, quantity, or importance, but are used to distinguish one element from another. The terms "an," "a," and "the / described" do not exclude quantity limitations and should be understood to cover both singular and plural forms unless otherwise stated herein or the context clearly contradicts. "Or" means "and / or," unless otherwise explicitly indicated. References throughout to "some embodiments," "implementations," etc., mean that a particular element described in connection with an embodiment is included in at least one embodiment described herein and may or may not exist in other embodiments. Furthermore, it should be understood that the described elements can be combined in any suitable manner in various embodiments. "Combinations of these" is open and includes any combination containing at least one of the listed components or properties, optionally together with similar or equivalent components or properties not listed.

[0093] Unless otherwise defined, the technical and scientific terms used herein have the same meaning as commonly understood by one of those skilled in the art to which this application pertains. All cited patents, patent applications, and other references are incorporated herein by reference in their entirety. However, if any terminology in this application contradicts or conflicts with terminology in the incorporated references, the terminology in this application shall prevail over the conflicting terminology in the incorporated references.

[0094] Although specific embodiments have been described, alternatives, modifications, variations, improvements, and substantial equivalents that may not yet be foreseen by the applicant or a person skilled in the art can be conceived. Therefore, the appended claims, as filed and as they may be modified, are intended to cover all such alternatives, modifications, variations, improvements, and substantial equivalents.

[0095] Although the processes, methods, and systems of this disclosure have been described with reference to exemplary embodiments thereof, this disclosure is not limited to such exemplary embodiments and / or implementations. Rather, the processes, methods, and systems of this disclosure are susceptible to many implementations and applications, which will be apparent to those skilled in the art from the disclosure herein. This disclosure expressly includes such modifications, enhancements, and / or variations to the disclosed embodiments. Because many changes can be made to the foregoing construction, and many different embodiments of this disclosure can be made without departing from the scope of this disclosure, all content contained in the drawings and specification is intended to be illustrative rather than restrictive. Additional modifications, alterations, and substitutions are contemplated in the foregoing disclosure. Therefore, it is appropriate that the appended claims be interpreted broadly and in a manner consistent with the scope of this disclosure.

Claims

1. An integrated process for producing bisphenol A, the process comprising: separating a first stream comprising acetone and phenol to provide a second stream comprising acetone and a third stream comprising phenol; and reacting acetone present in the second stream and phenol present in the third stream to produce a product stream comprising bisphenol A and a recycle stream.

2. The process of claim 1, wherein: the recycle stream comprises acetone; and reacting acetone present in the second stream and phenol present in the third stream to produce the product stream comprises reacting at least a portion of the acetone present in the recycle stream to produce the product stream.

3. The method of claim 1 or 2, further comprising combining the first stream and the recycle stream to provide a combined stream, wherein separating the first stream to provide the second stream and the third stream comprises: separating the combined stream to provide the second stream and the third stream.

4. The process of claim 3, further comprising adjusting the composition of the combined stream prior to separating the combined stream to provide the second stream and the third stream.

5. The process of any one of the preceding claims, further comprising purifying the second stream prior to reacting acetone present in the second stream and phenol present in the third stream to produce the product stream comprising bisphenol A.

6. The process of any one of the preceding claims, further comprising purifying the third stream prior to reacting acetone present in the second stream and phenol present in the third stream to produce the product stream comprising bisphenol A.

7. The process of any one of the preceding claims, further comprising: reacting benzene and acetone to produce cumene; oxidizing the cumene to produce cumene hydroperoxide; and cleaving the cumene hydroperoxide to produce the first stream, wherein the first stream further comprises a-methylstyrene.

8. The process of any one of the preceding claims, further comprising cleaving hydrocarbon compounds present in the third stream.

9. The process of claim 8, wherein cleaving hydrocarbon compounds present in the third stream produces a cleaved hydrocarbon stream comprising phenol.

10. The method of claim 9, wherein separating the first stream to provide the second stream and the third stream comprises: separating the cleaved hydrocarbon stream to provide the second stream and the third stream.

11. The process of claim 2, wherein: reacting acetone present in the second stream and phenol present in the third stream to produce the product stream comprises: reacting acetone present in the second stream and phenol present in the third stream in a first reactor to produce a first product stream comprising bisphenol A and a first recycle stream, and reacting acetone present in the second stream and phenol present in the third stream in a second reactor to produce a second product stream comprising bisphenol A and a second recycle stream; and reacting acetone present in the recycle stream to produce the product stream comprises: reacting acetone present in the first recycle stream to produce the product stream, and reacting acetone present in the second recycle stream to produce the product stream.

12. The process of any one of claims 1 to 10, wherein reacting acetone present in the second stream and phenol present in the third stream to produce the product stream comprises: reacting acetone present in the second stream and phenol present in the third stream in a first reactor to produce a first product stream comprising bisphenol A and a first recycle stream, and reacting acetone present in the second stream and phenol present in the third stream in a second reactor to produce a second product stream comprising bisphenol A and a second recycle stream; and The method further includes reacting phenol present in the first recycle stream with acetone present in the second stream and phenol present in the third stream in the second reactor to produce the second product stream comprising bisphenol A and the second recycle stream, wherein the weight percent of bisphenol A present in the first product stream based on the total weight of the first product stream is greater than the weight percent of bisphenol A present in the second product stream based on the total weight of the second product stream.

13. An integrated method for producing bisphenol A, the method comprising: reacting benzene and acetone to produce cumene; oxidizing the cumene to produce cumene hydroperoxide; cracking the cumene hydroperoxide to produce a first stream comprising acetone, phenol, and a-methylstyrene; separating the first stream to provide a second stream comprising acetone and a third stream comprising phenol; cracking hydrocarbon compounds present in the third stream to produce a cracked hydrocarbon stream comprising phenol; purifying the second stream to provide a purified second stream comprising a greater proportion of acetone than the second stream; providing a purified third stream comprising a greater proportion of phenol than the third stream after purifying the third stream; and reacting acetone present in the purified second stream and phenol present in the purified third stream to produce a product stream comprising bisphenol A and a recycle stream; wherein the recycle stream comprises acetone, wherein separating the first stream to provide the second stream and the third stream comprises separating the cracked hydrocarbon stream to provide the second stream and the third stream, and wherein reacting acetone present in the purified second stream and phenol present in the purified third stream to produce the product stream comprises reacting at least a portion of the acetone present in the recycle stream to produce the product stream.

14. An integrated system for producing bisphenol A, comprising: a first column for separating a first stream to provide a second stream comprising acetone and a third stream comprising phenol; a reactor for reacting acetone present in the second stream and phenol present in the third stream to produce a product stream comprising bisphenol A and a recycle stream; and a recycle line for recycling the recycle stream back to the first column.

15. The integrated system of claim 14, wherein the reactor for reacting acetone present in the second stream and phenol present in the third stream to produce the product stream comprises: a first reactor for reacting acetone present in the second stream and phenol present in the third stream to produce a first product stream comprising bisphenol A and a first recycle stream; and a second reactor for reacting acetone present in the second stream and phenol present in the third stream to produce a second product stream comprising bisphenol A and a second recycle stream.

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