WO2017111357A1 - Procédé de récupération de phénol et d'acétone à partir d'un produit de la réaction de décomposition d'un résidu de bisphénol a - Google Patents

Procédé de récupération de phénol et d'acétone à partir d'un produit de la réaction de décomposition d'un résidu de bisphénol a Download PDF

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Publication number
WO2017111357A1
WO2017111357A1 PCT/KR2016/014334 KR2016014334W WO2017111357A1 WO 2017111357 A1 WO2017111357 A1 WO 2017111357A1 KR 2016014334 W KR2016014334 W KR 2016014334W WO 2017111357 A1 WO2017111357 A1 WO 2017111357A1
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WIPO (PCT)
Prior art keywords
acetone
phenol
bisphenol
decomposition reaction
reaction product
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PCT/KR2016/014334
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English (en)
Korean (ko)
Inventor
이상범
신준호
정인용
박종휘
금명연
김정호
김태호
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주식회사 엘지화학
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Priority claimed from KR1020160143198A external-priority patent/KR101953801B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to EP16879224.0A priority Critical patent/EP3395791B1/fr
Priority to JP2018506969A priority patent/JP6571270B2/ja
Priority to US15/751,360 priority patent/US10358403B2/en
Priority to CN201680055797.2A priority patent/CN108026009B/zh
Publication of WO2017111357A1 publication Critical patent/WO2017111357A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
    • C07C37/52—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms by splitting polyaromatic compounds, e.g. polyphenolalkanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
    • C07C37/72—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/86—Purification; separation; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/517—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of peroxy-compounds to >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/08—Acetone

Definitions

  • the present invention relates to a method for recovering phenol and acetone from a bisphenol-A residue decomposition product, and more particularly, to improve the economics and efficiency by utilizing the phenol / acetone purification process used in the production of bisphenol-A. And a process for recovering phenol and acetone from bisphenol-A residue decomposition reaction products.
  • the bisphenol-A residue decomposition product was fed to a purification tower, followed by distillation of acetone, and the phenol-containing stream (stream) Along with the extractant, it is sent to the neutralization tank, and the phenol-containing stream and extractant are layered into the upper organic layer and the lower receiving layer. Subsequently, the extractant and phenol of the upper organic layer are respectively recovered by distillation, and the phenol remaining in the lower aqueous layer is removed by extraction and then discharged into a wastewater treatment process.
  • Another object of the present invention is to recycle the wastewater generated during the process as water used in the bisphenol-A residue decomposition reaction, thereby reducing costs and reducing environmental pollution, resulting in phenol from bisphenol-A residue decomposition products. And a method for recovering acetone.
  • the present invention (a) decomposition and purification of cumene hydro peroxide prepared by the oxidation reaction of cumene, separating the phenol and acetone; (b) purging the bisphenol-A prepared by reacting the separated phenol and acetone, and purging streams further enriched by venting and withdrawing some or all of the purge stream or phenol containing unisolated bisphenol-A. Cracking the stream under an aqueous alkaline solution; And (C) supplying the reaction product of the decomposition reaction to a process for separating the phenol and acetone to separate the phenol and acetone, wherein steps (a) and (C) are performed simultaneously.
  • a process for the recovery of phenol and acetone from bisphenol-A residue decomposition reaction products is provided.
  • the process equipment is simplified and the required cost Can reduce the cost.
  • the waste water generated during the process to use the water used in the decomposition reaction, it is possible to reduce the cost and reduce the environmental pollution.
  • FIG. 1 is a process schematic diagram illustrating a method for recovering phenol and acetone from a bisphenol-A residue decomposition product according to an embodiment of the present invention.
  • FIG. 1 is a process schematic diagram illustrating a method for recovering phenol and acetone from a bisphenol-A residue decomposition reaction product according to an embodiment of the present invention.
  • the method for recovering phenol and acetone from the bisphenol-A residue decomposition reaction product according to (a) decomposing and purifying cumene hydroperoxide prepared by the oxidation reaction of cumene, isolating phenol and acetone, ( b) purging the bisphenol-A prepared by reacting the separated phenol and acetone and purging stream further enriched by venting and withdrawing some or all of the unisolated bisphenol-A.
  • C supplying the reaction product by the decomposition reaction to a process for separating the phenol and acetone.
  • step (a) and (C) is characterized in that it is carried out at the same time.
  • Step (a) is a step of using a cumene purification process and a phenol / acetone purification process.
  • a cumene is prepared by alkylating propylene and benzene, and then, through a purification process, heavy ( Heavy / light by-products are discharged and cumene is purified and separated.
  • the purified cumene is oxidized to produce cumene hydro peroxide (CHP), and the cumene hydroperoxide (CHP) is decomposed and reacted under a conventional acid catalyst such as sulfuric acid (H 2 SO 4 ).
  • a conventional acid catalyst such as sulfuric acid (H 2 SO 4 ).
  • Phenol, acetone, alpha-methyl stylene (AMS) and heavy by-products are produced, and the purification process releases alpha-methyl styrene (AMS) and heavy by-products, while phenol and acetone Purify and isolate.
  • the step (b) is to use a bisphenol-A purification process, first, by reacting the purified separated phenol and acetone, bisphenol-A (BPA), more specifically crude bisphenol After -A is prepared, bisphenol-A with improved purity is obtained through a crystallization process.
  • BPA bisphenol-A
  • Bisphenol-A prepared as described above proceeds in two ways, one route is to separate and commercialize bisphenol-A in the form of para, para (para, para) having a purity of 99% or more through a BPA purification process. Another route is recycled to the reactor with heavy by-products and phenols produced in the production of the bisphenol-A, or it is a purge stream which is decomposed under alkaline aqueous solution.
  • the phenol constituting the purge stream may be unreacted phenol and phenol used for washing in the BPA crystallization process, that is, washing phenol.
  • the concentrated purge stream is excluded because some or all of the phenol is discharged and recovered by distillation, and phenol may be included in the purge stream to function as a solvent. This can also be referred to as a concentrated purge stream.
  • the purge stream comprising bisphenol-A may comprise 5 to 20 wt% bisphenol-A, 60 to 90 wt% phenol and 3 to 15 wt% isomers and heavy by-products
  • the concentrated purge The stream contains 40 to 60% by weight of bisphenol-A, 0 to 15% by weight of phenol, 35 to 60% by weight of isomers and heavy by-products, with excess alkali having properties of bases such as NaOH, KOH and LiOH. It is decomposed under an aqueous solution, and the supply amount of alkali may be 2 to 40 parts by weight, preferably 5 to 30 parts by weight, based on 100 parts by weight of the purge stream.
  • reaction of phenol and acetone in the step (b) is carried out at 40 to 150 °C, preferably 50 to 100 °C
  • the decomposition reaction may be carried out at 150 to 300 °C, preferably 200 to 280 °C have.
  • step (C) is a step for recovering phenol and acetone by reusing the phenol / acetone purification process used in step (a), and the product of the decomposition reaction of step (b) is an excess of alkali. Since it contains an aqueous solution, liquid-liquid separation by neutralization is easy separation method, as described above, since (C) step is to reuse the phenol / acetone purification process used in step (a), neutralization In the neutralization tank in which the neutralization reaction is performed, not only the bisphenol-A residue decomposition product of step (b) but also cumene hydroperoxide decomposition product of step (a) may be supplied together.
  • the cumene hydro peroxide decomposition product and the bisphenol-A residue decomposition reaction product may be adjusted in various ratios according to the needs of the user, but is preferably supplied to the neutralization tank at a ratio of 75:25 to 99: 1%.
  • the bisphenol-A residue decomposition reaction product includes 5 to 50% by weight of phenol and acetone, 2 to 15% by weight of alkali metal hydroxide, 30 to 90% by weight of water, and 3 to 15% by weight of remaining byproducts. Included.
  • the neutralization reaction may be carried out at 20 to 100 °C, preferably 30 to 70 °C.
  • Steps (a) and (C) are performed simultaneously, wherein the phenol / acetone separation comprises: (i) dissolving the cumene hydroperoxide decomposition product and bisphenol-A residue decomposition product into sulfuric acid (H 2 SO 4 ) neutralizing by inputting a common acid and the like, and separating the crude layer into a stream containing crude acetone and phenol and an aqueous layer comprising some acetone, and (ii) the stream comprising crude acetone and phenol.
  • sulfuric acid H 2 SO 4
  • step (i) When the stream comprising crude acetone and phenol separated in step (i) is fed to the crude Acetone Column, the phenol and heavy byproducts having relatively high boiling point are After being separated into phenol, phenol is recovered through a phenol purification process, and the crude acetone having a lower boiling point than phenol is transferred to an acetone recovery column.
  • the neutralization tank is a layer separator in which liquid-liquid separation is performed by neutralization, and components such as water and by-products included in the receiving layer are discharged to the wastewater.
  • Acetone is recovered by transporting and distilling to the Acetone Product Column, whereby light by-products are also separated and discharged.
  • the amount of acetone recovered from the bisphenol-A residue decomposition reaction product is 1 to 7% relative to the amount of acetone used to prepare the bisphenol-A.
  • the remaining hydrocarbons having a higher boiling point than acetone, which contain phenol are separated by a conventional basic substance such as caustic soda, and separated into a wastewater containing some hydrocarbons and a stream containing alpha-methylstyrene (AMS).
  • AMS alpha-methylstyrene
  • the hydrocarbon containing water located in the lower portion of the acetone product column (alpha) has a phenyl group, such as alpha-methylstyrene and unreacted cumene generated by decomposition of the cumene hydroperoxide (CHP)
  • a phenyl group such as alpha-methylstyrene and unreacted cumene generated by decomposition of the cumene hydroperoxide (CHP)
  • CHP cumene hydroperoxide
  • the aqueous alkali solution used here is also an aqueous solution containing an alkali metal hydroxide selected from the group consisting of NaOH, KOH and LiOH, wherein the phenol in the MOH (where M stands for alkali metal) solution is ionized to phenolate, The rate becomes phenol by exchanging metal ions with hydrogen ions of an acid such as sulfuric acid.
  • the phenol in the hydrocarbon of step (iii) is ionized under an aqueous alkaline solution to form phenolate, and is then recycled back to the bisphenol-A residue decomposition step or neutralization step in the form of waste water.
  • the waste water thus reused that is, the waste water discharged from the separation of phenol and acetone in the steps (a) and (c)) is supplied to the bisphenol-A residue decomposition step (b) or the neutralization step for reuse.
  • the phenol-containing wastewater is preferably supplied in a neutralization step so that the phenol can be easily recovered in the phenol / acetone refining process.
  • a small amount of hydrocarbons may be used in the wastewater reused in the bisphenol-A residue decomposition reaction. Phenol, alphamethyl styrene, and unreacted cumene).
  • the amount of wastewater used in the bisphenol-A residue decomposition step and the amount of wastewater used in the neutralization step may be adjusted at various ratios according to the needs of the user, but it is supplied at a ratio of 20 to 100%: 80 to 0%. desirable.
  • alpha-methylstyrene may be included in the trace wastewater
  • most of the alpha-methylstyrene may be included in the wastewater, which is transferred to the APC product column bottom separator through the lower portion of the acetone product column. It is transported to and discharged separately from heavy by-products.
  • the method for recovering phenol and acetone from the bisphenol-A residue decomposition reaction product according to the present invention is prepared in order to recover phenol and acetone from the bisphenol-A residue decomposition reaction product.
  • the recovery rate of phenol and acetone is described in US Pat. No. 8,431,749 (phenol and acetone from the bisphenol-A stream, which requires a separate separation process to recover phenol and acetone.
  • the total content is less than 100% by weight is due to the error that can appear in the actual device analysis, in the case of the BPA heavies composition shown in Table 1 may increase the heavy value, In the case of the BPA heavies composition shown in Table 2, water (H 2 O) and sodium hydroxide (NaOH) may be further included.
  • Example 1 except that 1.97 g of sodium hydroxide (NaOH) was used instead of 1.90 g, 17.54 g of distilled water was used instead of waste water, and 12.99 g of BPA heavies was used instead of 12.50 g.
  • NaOH sodium hydroxide
  • Example 2 Example 2 except that 1.97 g of sodium hydroxide (NaOH) was used instead of 1.90 g, 17.54 g of distilled water was used instead of waste water, and 12.99 g of BPA heavies was used instead of 12.50 g.
  • the same process was performed twice, and the BPA heavies composition after the reaction was terminated is shown in Table 2 below.
  • Example 1 In Comparative Example 1 using distilled water, the recovery of phenol and acetone ((phenol + acetone) weight / BPA heavies weight) per unit mass of BPA heavies was 78% (1st round) and 75% (2nd round). Although some of the distilled water has been consumed in the reaction, most of the distilled water has to be treated as waste water. Meanwhile, in Example 1 in which wastewater was recycled, recovery of phenol and acetone per unit mass of BPA heavies equivalent to that of Comparative Example 1 ((phenol + acetone) weight / BPA heavies weight) even when wastewater generated in the process was used. Indicated. In addition, since the wastewater generated during the existing process was recycled, no additional wastewater was generated, but rather, some of the wastewater was used for the conversion of phenol and acetone.
  • aqueous layer component discharged from the neutralization tank was introduced into a neutralization tank at 50 ° C. for sufficient layer separation, and then, 14 g of the reaction product produced by the decomposition reaction in Example 1 was neutralized. After further feeding into the bath, the pH was adjusted to 6.6 level using sulfuric acid (H 2 SO 4 ) while stirring, and after standing, the layers were separated within minutes to analyze the component content of each layer.
  • sulfuric acid H 2 SO 4
  • Example 2 The separation of the layers in the neutralization tank of Examples 2 and 3 was all performed within a short time, in the case of Example 2, the content of water (H 2 O) in the organic layer is 12% by weight, the content of organic matter in the aqueous layer is 1% by weight In the case of Example 3, the content of water (H 2 O) in the organic layer was measured to 8.5% by weight, and the content of organic matter in the aqueous layer was 1.2% by weight, so that both Examples 2 and 3 had good layer separation performance. Indicated.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de récupération de phénol et d'acétone à partir d'un produit de la réaction de décomposition d'un résidu de bisphénol A, le procédé permettant d'améliorer la faisabilité économique et le rendement grâce à un procédé de purification de phénol/acétone utilisé dans la production de bisphénol A. Le procédé de récupération de phénol et d'acétone à partir d'un produit de la réaction de décomposition d'un résidu de bisphénol A est caractérisé en ce qu'il comprend les étapes consistant à : (a) décomposer et purifier de d'hydroperoxyde de cumène, qui est obtenu par oxydation du cumène, pour en séparer le phénol et l'acétone ; (b) séparer le bisphénol A, qui est obtenu par une réaction du phénol et de l'acétone séparés, et évacuer et récupérer un courant de purge contenant le bisphénol A non séparé ou une partie ou la totalité du phénol, afin de décomposer le courant de purge concentré davantage dans une solution aqueuse alcaline ; et (c) introduire le produit de réaction issu de la réaction de décomposition dans le procédé de séparation de phénol et d'acétone, ce qui permet de séparer le phénol et l'acétone de celui-ci, les étapes (a) et (c) étant effectuées simultanément.
PCT/KR2016/014334 2015-12-23 2016-12-07 Procédé de récupération de phénol et d'acétone à partir d'un produit de la réaction de décomposition d'un résidu de bisphénol a WO2017111357A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP16879224.0A EP3395791B1 (fr) 2015-12-23 2016-12-07 Procédé de récupération de phénol et d'acétone à partir d'un produit de la réaction de décomposition d'un résidu de bisphénol a
JP2018506969A JP6571270B2 (ja) 2015-12-23 2016-12-07 ビスフェノールａ残渣分解反応生成物からフェノールおよびアセトンを回収するための方法
US15/751,360 US10358403B2 (en) 2015-12-23 2016-12-07 Method for recovering phenol and acetone from cracking reaction product of bisphenol-A residue
CN201680055797.2A CN108026009B (zh) 2015-12-23 2016-12-07 从双酚a残余物的裂化反应产物中回收苯酚和丙酮的方法

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KR20150185426 2015-12-23
KR10-2015-0185426 2015-12-23
KR10-2016-0143198 2016-10-31
KR1020160143198A KR101953801B1 (ko) 2015-12-23 2016-10-31 비스페놀-a 잔사물 분해 반응 생성물로부터 페놀 및 아세톤을 회수하기 위한 방법

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111868020A (zh) * 2018-12-20 2020-10-30 株式会社Lg化学 分解酚类副产物的方法和设备

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09110766A (ja) * 1995-10-20 1997-04-28 Mitsubishi Chem Corp ビスフェノールａの製造方法
KR20100017484A (ko) * 2007-05-09 2010-02-16 스톤 앤드 웹스터 인코포레이티드 비스페놀-ａ 처리 개선 방법
US8431749B2 (en) 2011-06-06 2013-04-30 Badger Licensing Llc Recovery of phenol and acetone from bisphenol-A streams
KR20150032842A (ko) * 2012-06-28 2015-03-30 이데미쓰 고산 가부시키가이샤 비스페놀 a의 제조 방법
KR20160143198A (ko) 2015-06-04 2016-12-14 박민규 실리카 및 마그네시아 추출을 위한 슬래그의 처리방법

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09110766A (ja) * 1995-10-20 1997-04-28 Mitsubishi Chem Corp ビスフェノールａの製造方法
KR20100017484A (ko) * 2007-05-09 2010-02-16 스톤 앤드 웹스터 인코포레이티드 비스페놀-ａ 처리 개선 방법
US8431749B2 (en) 2011-06-06 2013-04-30 Badger Licensing Llc Recovery of phenol and acetone from bisphenol-A streams
KR20140037843A (ko) * 2011-06-06 2014-03-27 바져 라이센싱 엘엘씨 비스페놀-에이 스트림들로부터 페놀 및 아세톤의 회수
KR20150032842A (ko) * 2012-06-28 2015-03-30 이데미쓰 고산 가부시키가이샤 비스페놀 a의 제조 방법
KR20160143198A (ko) 2015-06-04 2016-12-14 박민규 실리카 및 마그네시아 추출을 위한 슬래그의 처리방법

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111868020A (zh) * 2018-12-20 2020-10-30 株式会社Lg化学 分解酚类副产物的方法和设备
JP2021514964A (ja) * 2018-12-20 2021-06-17 エルジー・ケム・リミテッド フェノール系副産物の分解方法およびその分解装置
US11247958B2 (en) 2018-12-20 2022-02-15 Lg Chem, Ltd. Method and apparatus for decomposing phenolic by-product
JP7104794B2 (ja) 2018-12-20 2022-07-21 エルジー・ケム・リミテッド フェノール系副産物の分解方法およびその分解装置
CN111868020B (zh) * 2018-12-20 2023-10-24 株式会社Lg化学 分离酚类副产物的方法和设备

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