阅读说明：本技术 分解酚类副产物的方法 (Method for decomposing phenolic by-products ) 是由 李相范 姜旻皙 申俊浩 于 2019-10-15 设计创作，主要内容包括：本发明涉及一种分解酚类副产物的方法,更具体地,涉及一种分解在苯酚制备工艺中产生的酚类副产物的方法,该方法包括：步骤(S10),将酚类副产物流、分解装置侧排出流和工艺用水加入到混合装置中,并且混合所述酚类副产物流、分解装置侧排出流和工艺用水；步骤(S20),将从混合装置排出的混合装置排出流加入到相分离装置中,并且将混合装置排出流相分离成油相和水相；步骤(S30),将通过步骤(S20)中的相分离得到并排出的油相流进料到分解装置中,并分解油相流；和步骤(S40),使通过步骤(S30)中的分解得到的分解装置侧排出流循环至步骤(S10)中的混合装置中。(The present invention relates to a method for decomposing a phenolic byproduct, and more particularly, to a method for decomposing a phenolic byproduct generated in a phenol preparation process, the method comprising: a step (S10) of feeding the phenolic byproduct stream, the decomposition device-side discharge stream and the process water into a mixing device, and mixing the phenolic byproduct stream, the decomposition device-side discharge stream and the process water; a step (S20) of feeding the mixing device discharge stream discharged from the mixing device to a phase separation device and phase-separating the mixing device discharge stream into an oil phase and a water phase; a step (S30) of feeding the oil phase stream, which is obtained and discharged by the phase separation in the step (S20), into a decomposition device and decomposing the oil phase stream; and a step (S40) of circulating the decomposition device-side discharge stream obtained by the decomposition in the step (S30) to the mixing device in the step (S10).)

1. A method of decomposing phenolic byproducts produced in a phenol production process, the method comprising:

a step S10 of feeding the phenolic byproduct stream, the decomposer side effluent stream and the process water to a mixing device and mixing the phenolic byproduct stream, the decomposer side effluent stream and the process water;

a step S20 of feeding the discharge stream of the mixing device discharged from the mixing device into a phase separation device and phase-separating the discharge stream of the mixing device into an oil phase and a water phase;

step S30 of feeding the oil phase stream obtained and discharged by the phase separation in step S20 to a decomposition device and decomposing the oil phase stream; and

in step S40, the decomposer-side effluent stream obtained by the decomposition in step S30 is circulated to the mixing apparatus in step S10.

2. The method of claim 1, wherein the phenolic byproduct stream comprises one or more selected from the group consisting of phenol, alpha-methylstyrene, acetophenone, cumylphenol, and alpha-methylstyrene dimer.

3. The process of claim 1, wherein the decomposer side effluent stream comprises one or more selected from phenol, acetophenone, alpha-methylstyrene and cumene.

4. The process of claim 1, wherein the decomposer side effluent stream comprises 50 wt% or more acetophenone.

5. The method of claim 1, wherein the process water has a pH of 3.5 to 7.

6. The method of claim 1, wherein the process water comprises process water from the aqueous phase solution separated in step S20.

7. The process of claim 1, wherein the decomposer overhead stream obtained by the decomposing in step S30 comprises one or more selected from the group consisting of phenol, α -methylstyrene and cumene.

8. The method of claim 1, further comprising:

prior to the step S10 of the above-mentioned step,

step S1, acid decomposition reaction is carried out on cumene hydroperoxide in the presence of an acid catalyst;

a step S2 of adding an alkaline aqueous solution to the acid decomposition reaction solution discharged in the step S1, neutralizing the acid decomposition reaction solution, and phase-separating the neutralized acid decomposition reaction solution into an oil phase and a water phase;

a step S3 of feeding the oil-phase acid decomposition reaction solution separated in the step S2 into a separation device and separating the oil-phase acid decomposition reaction solution into a separation device top effluent stream containing acetone and a separation device bottom effluent stream containing phenol; and

step S4, feeding the splitter bottom effluent stream separated in step S3 to a phenol column and separating the splitter bottom effluent stream into a phenol overhead effluent stream comprising phenol and a phenol bottom effluent stream comprising phenolic by-products.

9. The method of claim 8, wherein the process water comprises process water from the aqueous phase solution separated in step S2.

10. The process of claim 8, wherein the phenolic byproduct stream is a phenol bottoms vent stream.

11. The method according to claim 8, wherein a top effluent stream of the decomposition device obtained by the decomposition in step S30 is mixed with the oil-phase acid decomposition reaction solution before the oil-phase acid decomposition reaction solution separated in step S2 is fed into a separation device.

Technical Field

Cross Reference to Related Applications

This application claims the benefit of priority from korean patent application No.10-2018-0166127, filed on 20.12.2018, the entire contents of which are incorporated herein by reference.

Background

Typically, about 95% of the phenol used in the world is produced by the Hock process. The Hock process proceeds in three steps, including: a step (1) of forming cumene by alkylation of benzene with propylene, a step (2) of oxidizing cumene to Cumene Hydroperoxide (CHP) by combining the cumene and oxygen, and a step (3) of decomposing the cumene hydroperoxide into phenol and acetone by an acid decomposition reaction in the presence of an acid catalyst.

Here, in the cumene oxidation step as the step (2), by-products such as Acetophenone (AP), dimethylbenzyl alcohol (DMBA), dicumyl peroxide (DCP) and dicumyl benzene (DC) are generated in addition to cumene hydroperoxide.

In addition, in the acid decomposition reaction of cumene hydroperoxide in step (3), by-products such as Hydroxyacetone (HA), 2-methylbenzofuran (2-MBF), α -methylstyrene (AMS), isopropylidene acetone (MO), α -methylstyrene (AMS) dimer and Cumyl Phenol (CP) are generated in addition to phenol and acetone.

Therefore, since the product stream produced in such a reaction process exists in a state where phenol, acetone and various by-products are mixed, a separation process for separating phenol from the product stream is required.

The product stream is fed to a separate separation device, an acetone-like mixture containing unreacted cumene, acetone, alpha-methylstyrene, hydroxyacetone, etc. is separated off via the top of the separation device, and a phenolic mixture containing phenol, a portion of the alpha-methylstyrene, 2-methylbenzofuran and other by-products is separated off via the bottom of the separation device.

The phenolic mixture separated through the bottom of the separation device is fed to a phenol column, phenol is separated through the top of the phenol column, and phenolic by-products, such as dicumyl peroxide, cumyl phenol, alpha-methyl styrene dimer or tar, are separated through the bottom of the phenol column.

Meanwhile, in the related art, the phenolic by-products separated through the bottom of the phenol column are used as fuels or discharged without additional treatment. However, since the phenolic by-products separated through the bottom of the phenol column contain phenol as a product, some active components such as α -methylstyrene and the like, in addition to tar as an impurity, it is necessary to separate and recover the active components from the phenolic by-products. When the by-products contained in the phenolic by-products are decomposed, cumene or the like can be produced.

Therefore, studies have been made to obtain phenol and active components remaining in the phenolic by-products separated through the bottom of the phenol column, and phenol and active components produced by decomposition of the phenolic by-products.

Disclosure of Invention

Technical problem

In order to solve the problems mentioned in the background art, it is an object of the present invention to prevent the overload of a phenol production process while decomposing phenol by-products generated in the phenol production process to obtain active components.

That is, it is an object of the present invention to provide a method for decomposing a phenolic by-product, which is capable of effectively removing salts contained in the phenolic by-product before the decomposition of the phenolic by-product, thereby preventing an overload of a phenol production process and an increase in energy consumption, while effectively obtaining an active component by decomposing the phenolic by-product.

Technical scheme

In one general aspect, there is provided a method of decomposing phenolic byproducts produced in a phenol production process, the method comprising: a step (S10) of feeding the phenolic byproduct stream, the decomposition device-side discharge stream and the process water into a mixing device, and mixing the phenolic byproduct stream, the decomposition device-side discharge stream and the process water; a step (S20) of feeding the mixing device discharge stream discharged from the mixing device to a phase separation device and phase-separating the mixing device discharge stream into an oil phase and a water phase; a step (S30) of feeding the oil phase stream, which is obtained and discharged by the phase separation in the step (S20), into a decomposition device and decomposing the oil phase stream; and a step (S40) of circulating the decomposition device-side discharge stream obtained by the decomposition in the step (S30) to the mixing device in the step (S10).

Advantageous effects

According to the method for decomposing a phenolic byproduct of the present invention, in the case of decomposing a phenolic byproduct generated in a phenol production process, salts contained in the phenolic byproduct can be effectively removed before the decomposition of the phenolic byproduct, whereby the content of acetophenone in the active ingredient can be reduced while the active ingredient can be effectively obtained by decomposing the phenolic byproduct.

In addition, according to the method for decomposing a phenolic byproduct of the present invention, in the case of decomposing a phenolic byproduct generated in a phenol production process, it is possible to prevent an overload of the phenol production process and an increase in energy consumption.

Drawings

FIG. 1 is a process flow diagram illustrating a method of decomposing a phenolic byproduct according to an exemplary embodiment of the present invention;

FIG. 2 is a process flow diagram illustrating a method of decomposing a phenolic byproduct in accordance with another exemplary embodiment of the present invention;

FIG. 3 is a process flow diagram illustrating a method of decomposing a phenolic byproduct, including a phenol production process, according to an exemplary embodiment of the present invention;

FIG. 4 is a process flow diagram illustrating a method of decomposing a phenolic byproduct according to another exemplary embodiment of the present invention, including a phenol production process;

FIG. 5 is a process flow diagram showing the method of decomposing phenolic by-products according to comparative examples 1 and 2 of the present invention;

FIG. 6 is a process flow diagram showing a method of decomposing a phenolic byproduct according to comparative example 3 of the present invention;

fig. 7 is a process flow diagram showing a method for decomposing a phenolic byproduct according to comparative example 4 of the present invention.

Detailed Description