Method for decomposing phenolic by-product

Patent metadata

Field	Value
Publication number	US-11370735-B2
Application number	US-201916765104-A
Country	US
Kind code	B2
Filing date	Oct 15, 2019
Priority date	Dec 20, 2018
Publication date	Jun 28, 2022
Grant date	Jun 28, 2022

Abstract

A method for decomposing a phenolic by-product generated in a phenol preparation process, the method including: adding a phenolic by-product stream, a decomposition apparatus side discharge stream, and process water to a mixing apparatus and mixing the phenolic by-product stream, the decomposition apparatus side discharge stream, and the process water; adding a mixing apparatus discharge stream discharged from the mixing apparatus to a phase separation apparatus and phase-separating the mixing apparatus discharge stream into an oil phase and an aqueous phase; feeding an oil phase stream discharged from the phase-separation apparatus and discharged to a decomposition apparatus and decomposing the oil phase stream; and circulating the decomposition apparatus side discharge stream discharged from the decomposition apparatus to the mixing apparatus.

First claim

The invention claimed is:

1. A method for decomposing a phenolic by-product generated in a phenol preparation process, the method comprising:
adding a phenolic by-product stream, a decomposition apparatus side discharge stream, and process water to a mixing apparatus and mixing the phenolic by-product stream, the decomposition apparatus side discharge stream, and the process water;
adding a mixing apparatus discharge stream discharged from the mixing apparatus to a phase separation apparatus and phase-separating the mixing apparatus discharge stream into an oil phase and an aqueous phase;
feeding an oil phase stream discharged from the phase-separation apparatus to a decomposition apparatus and decomposing the oil phase stream; and
circulating the decomposition apparatus side discharge stream discharged from the decomposition apparatus to the mixing apparatus.

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

3. The method of claim 1 , wherein the decomposition apparatus side discharge stream comprises one or more selected from the group consisting of phenol, acetophenone, alpha-methyl styrene, and cumene.

4. The method of claim 1 , wherein the decomposition apparatus side discharge stream comprises 50 wt % or more of acetophenone.

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

6. The method of claim 1 , wherein the process water includes process water derived from the aqueous phase solution.

7. The method of claim 1 , wherein a decomposition apparatus upper discharge stream discharged from the decomposition apparatus contains one or more selected from the group consisting of phenol, alpha-methyl styrene, and cumene.

8. The method of claim 1 , further comprising:
prior to adding the phenolic by-product stream,
performing an acid decomposition reaction on cumene hydroperoxide in the presence of an acid catalyst;
adding a basic aqueous solution to an acid decomposition reaction solution discharged from the acid decomposition reaction neutralizing the acid decomposition reaction solution, and phase-separating the neutralized acid decomposition reaction solution into an oil phase and an aqueous phase;
feeding an oil phase acid decomposition reaction solution to a separation apparatus and separating the oil phase acid decomposition reaction solution into a separation apparatus upper discharge stream containing acetone and a separation apparatus bottom discharge stream containing phenol; and
feeding the separation apparatus bottom discharge stream discharged from the separation apparatus to a phenol column and separating the separation apparatus bottom discharge stream into a phenol column upper discharge stream containing phenol and a phenol column bottom discharge stream containing a phenolic by-product.

9. The method of claim 8 , wherein the process water includes process water derived from the aqueous phase.

10. The method of claim 8 , wherein the phenolic by-product stream is the phenol column bottom discharge stream.

11. The method of claim 8 , wherein a decomposition apparatus upper discharge stream discharged from the decomposition apparatus is mixed with the oil phase before the oil phase is added to the separation apparatus.

12. The method of claim 1 , wherein the phenolic by-product stream and the decomposition apparatus side discharge stream are added to the mixing apparatus at a ratio of 1:0.1 to 1:1 based on a weight or a flow rate.

13. The method of claim 12 , wherein the phenolic by-product stream and the decomposition apparatus side discharge stream are added to the mixing apparatus at a ratio of 1:0.2 to 1:0.5.

14. The method of claim 13 , wherein the phenolic by-product stream and the decomposition apparatus side discharge stream are added to the mixing apparatus at a ratio of 1:0.25 to 1:0.33.

15. The method of claim 1 , wherein the phenolic by-product stream and the process water are added to the mixing apparatus at a ratio of 1:1 to 1:5 based on a weight or flow rate.

16. The method of claim 15 , wherein the phenolic by-product stream and the process water are added to the mixing apparatus at a ratio of 1:1 to 1:3.

17. The method of claim 16 , wherein the phenolic by-product stream and the process water are added to the mixing apparatus at a ratio of 1:1.25 to 1:1.4.

Assignees

• Lg Chemical Ltd

Inventors

• Lee Sang Beom
• Kang Min Suk
• Shin Joon Ho

Classifications

• C07C4/24

  by splitting polyarylsubstituted aliphatic compounds at an aliphatic-aliphatic bond, e.g. 1,4-diphenylbutane to styrene · CPC title

• C07C37/52

  by splitting polyaromatic compounds, e.g. polyphenolalkanes · CPC title

• C07C37/86 Primary

  by treatment giving rise to a chemical modification (chemisorption C07C37/82) · CPC title

• C07C45/82

  by distillation · CPC title

• C07C1/20 Primary

  starting from organic compounds containing only oxygen atoms as heteroatoms · CPC title