KR102457801B1 - 페놀 제조 공정에서의 부산물 분해방법 - Google Patents
페놀 제조 공정에서의 부산물 분해방법 Download PDFInfo
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- KR102457801B1 KR102457801B1 KR1020180096150A KR20180096150A KR102457801B1 KR 102457801 B1 KR102457801 B1 KR 102457801B1 KR 1020180096150 A KR1020180096150 A KR 1020180096150A KR 20180096150 A KR20180096150 A KR 20180096150A KR 102457801 B1 KR102457801 B1 KR 102457801B1
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- phenol
- acetophenone
- tar
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- reaction distillation
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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
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
- C07C15/085—Isopropylbenzene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
- C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
- C07C15/46—Styrene; Ring-alkylated styrenes
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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
- C07C37/50—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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/04—Phenol
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- 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
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
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- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
Abstract
Description
도 2는 반응기와 증류탑이 일체화된 형태의 종래의 페놀 부산물 분해장치(비교예 2)를 간략히 도시한 것이다.
도 3은 본 발명의 일 실시예에 따른 반응증류탑의 형태(실시예 1)를 간략히 도시한 것이다.
도 4는 본 발명의 다른 실시예에 따른 열교환기를 포함하는 반응증류탑의 형태(실시예 2)를 간략히 도시한 것이다.
도 5는 반응기와 증류탑이 일체화된 형태의 종래의 페놀 부산물 분해장치에서 유효성분만을 컬럼 측면에서 분리하는 형태(비교예 3)를 간략히 도시한 것이다.
| ※페놀 부산물 1000kg/hr 기준 AP 약 99 중량% 이상 혼합 시 | |||||||
| 구분 | 페놀 부산물 | 실시예 1 | 실시예 2 | 비교예 1 | 비교예 2 | 비교예 3 | |
| Pressure (KG) | - | 0.00 | 0.00 | 0.00 | 7.00 | 0.00 | |
| Heat duty (Gcal/hr) | - | 0.27 | 0.22 | 0.35 | 0.38 | 0.25 | |
| 회수된 유효성분의 성분 비율 (중량%) | Phenol | 4.21 | 7.72 | 7.72 | 8.59 | 12.28 | 4.61 |
| Alpha-methylstyrene | 7.88 | 28.85 | 28.85 | 24.48 | 7.33 | 22.40 | |
| cumene | 0.00 | 5.56 | 5.56 | 3.53 | 6.49 | 3.90 | |
| Acetophenone | 19.22 | 0.04 | 0.04 | 0.04 | 0.04 | 0.04 | |
| Cumyl phenol | 28.04 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | |
| Dimers of alpha-methylstyrene | 15.40 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | |
| Others | 25.25 | 1.96 | 1.96 | 1.96 | 1.95 | 0.05 | |
| Total | 100.00 | 44.13 | 44.13 | 38.60 | 28.09 | 31.00 | |
Claims (8)
- 페놀 제조 공정에서 생성되는 페놀 부산물의 분해하는 방법에 있어서,
상기 부산물을 반응증류탑에 공급하여 분해반응을 실시하는 단계;
상기 반응증류탑 하부로부터 타르를 회수하는 단계;
반응증류탑 중간 측면부로부터 아세토페논을 회수하는 단계;
반응증류탑 상부로부터 유효성분을 회수하는 단계를 포함하고,
상기 반응증류탑 중간 측면부는 상기 반응증류탑의 총 단수의 25 ~ 90 % 위치에 구비된 것인 페놀 부산물 분해방법. - 제1항에 있어서,
상기 반응증류탑은 0.5 ~ 3 bar 에서 운전되는 것인 페놀 부산물의 분해방법. - 제1항에 있어서,
상기 회수된 아세토페논을 상기 타르와 혼합하는 단계를 더 포함하는 페놀 부산물의 분해방법. - 제1항에 있어서,
상기 타르 및 아세토페논의 혼합 스트림과 상기 반응증류탑에 공급되는 부산물을 열교환하여 페놀 부산물을 가열하는 단계를 더 포함하는 페놀 부산물의 분해방법. - 제1항에 있어서,
상기 유효성분은 페놀, 알파메틸스티렌 및 큐멘을 포함하는 것인 페놀 부산물의 분해방법. - 페놀 제조 공정의 부산물을 반응증류탑에 공급하기 위한 페놀 부산물 공급부;
상기 반응증류탑 하부에 구비된 타르 회수부;
상기 타르 회수부로부터 회수된 타르를 이송하는 타르 이송라인;
상기 반응증류탑 측면의 중간부에 구비된 아세토페논 회수라인;
상기 아세토페논 회수라인으로부터 회수된 아세토페논을 상기 회수된 타르와 혼합하기 위하여 상기 타르 이송라인과 연결된 아세토페논 이송라인; 및
상기 반응증류탑 상부에 구비된 유효성분 회수부를 포함하고,
상기 아세토페논 회수라인은 반응증류탑의 총 단수의 25 ~ 90 % 위치에 구비된 것인 페놀 부산물의 분해장치. - 삭제
- 제6항에 있어서,
상기 회수된 타르 및 아세토페논의 혼합스트림과 상기 페놀 부산물 사이의 열교환을 위한 열교환기를 더 구비하는 페놀 부산물의 분해장치.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020170154969 | 2017-11-20 | ||
| KR20170154969 | 2017-11-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20190058273A KR20190058273A (ko) | 2019-05-29 |
| KR102457801B1 true KR102457801B1 (ko) | 2022-10-21 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020180096150A Active KR102457801B1 (ko) | 2017-11-20 | 2018-08-17 | 페놀 제조 공정에서의 부산물 분해방법 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US11407694B2 (ko) |
| EP (1) | EP3680226B1 (ko) |
| JP (1) | JP7104707B2 (ko) |
| KR (1) | KR102457801B1 (ko) |
| CN (1) | CN110461806A (ko) |
| WO (1) | WO2019098501A1 (ko) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102337898B1 (ko) * | 2017-11-20 | 2021-12-09 | 주식회사 엘지화학 | 페놀 제조 공정에서의 부산물 분해방법 |
| KR102441561B1 (ko) * | 2018-12-20 | 2022-09-06 | 주식회사 엘지화학 | 페놀계 부산물의 분해 방법 및 이의 분해 장치 |
| KR102489404B1 (ko) | 2019-09-16 | 2023-01-16 | 주식회사 엘지화학 | 페놀계 부산물 분해 방법 |
| KR102489410B1 (ko) | 2019-09-16 | 2023-01-16 | 주식회사 엘지화학 | 페놀계 부산물 분해 방법 |
| KR102860383B1 (ko) | 2020-06-23 | 2025-09-15 | 주식회사 엘지화학 | 페놀계 부산물 분해방법 |
| KR102861475B1 (ko) | 2020-07-10 | 2025-09-17 | 주식회사 엘지화학 | 페놀계 부산물 분해방법 |
| KR102755582B1 (ko) | 2020-07-17 | 2025-01-14 | 주식회사 엘지화학 | 페놀계 부산물 분해방법 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100262026B1 (ko) * | 1994-10-04 | 2000-07-15 | 제이 엘. 차스킨, 버나드 스나이더, 아더엠. 킹 | 페놀타르 폐기물의 환원방법 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
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| NL127228C (ko) * | 1959-07-15 | |||
| US3850996A (en) * | 1970-10-08 | 1974-11-26 | Hercules Inc | Treatment of the heavy ends fraction of cumene hydroperoxide cleavage reaction mixture |
| GB1574420A (en) | 1976-12-18 | 1980-09-03 | Bp Chem Int Ltd | Process for recovering crude phenol from catalyst-free cumene hydroperoxide cleavage reaction products |
| CA1098916A (en) * | 1978-08-18 | 1981-04-07 | Max M. Wirth | Process for the production of a phenol and a carbonyl compound by the catalysed decomposition of an aromatic hydroperoxide |
| JPS60123434A (ja) * | 1983-12-06 | 1985-07-02 | Mitsui Toatsu Chem Inc | クメン法フェノ−ル蒸留残渣の処理方法 |
| IT1181903B (it) * | 1984-06-15 | 1987-09-30 | Anic Spa | Procedimento per la pirolisi di peci fenoliche |
| JP2920567B2 (ja) | 1990-08-07 | 1999-07-19 | ザ ダウ ケミカル カンパニー | 二成分繊維の製造法 |
| US5240568A (en) | 1991-08-29 | 1993-08-31 | Allied-Signal Inc. | Removal of acetophenone from phenol purification residues |
| RU2032656C1 (ru) * | 1992-04-23 | 1995-04-10 | Дыкман Аркадий Самуилович | Способ выделения фенола из фенольной смолы производства фенола и ацетона кумольным методом |
| EP0863195B1 (en) | 1997-02-28 | 2010-11-24 | SABIC Innovative Plastics IP B.V. | Phenol tar cracking process |
| RU2120433C1 (ru) | 1997-02-28 | 1998-10-20 | Дыкман Аркадий Самуилович | Способ переработки фенольной смолы, полученной в производстве фенола и ацетона кумольным методом |
| US6965056B1 (en) | 1999-05-03 | 2005-11-15 | Shell Oil Company | Removal of salts in the manufacture of phenolic compound |
| KR100321518B1 (ko) | 1999-05-07 | 2002-01-24 | 서곤 | 페놀 제조공정 부산물로부터 페놀, 큐멘, α-메틸스티렌의 회수방법 및 그의 장치 |
| JP5661466B2 (ja) | 2007-10-26 | 2015-01-28 | シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー | フェノール製造の間でのアセトフェノンの回収 |
| EP2234951B1 (en) | 2007-12-20 | 2016-10-19 | Borealis Technology OY | Purification of phenol |
| KR101378274B1 (ko) | 2010-06-08 | 2014-04-01 | 주식회사 엘지화학 | 페놀 불순물 제거 방법 |
| CN106631729A (zh) * | 2013-04-25 | 2017-05-10 | 乐天化学株式会社 | 苯乙酮的合成方法 |
| KR102337898B1 (ko) * | 2017-11-20 | 2021-12-09 | 주식회사 엘지화학 | 페놀 제조 공정에서의 부산물 분해방법 |
-
2018
- 2018-08-17 EP EP18878724.6A patent/EP3680226B1/en active Active
- 2018-08-17 US US16/478,802 patent/US11407694B2/en active Active
- 2018-08-17 JP JP2019536539A patent/JP7104707B2/ja active Active
- 2018-08-17 CN CN201880006831.6A patent/CN110461806A/zh active Pending
- 2018-08-17 KR KR1020180096150A patent/KR102457801B1/ko active Active
- 2018-08-17 WO PCT/KR2018/009459 patent/WO2019098501A1/ko not_active Ceased
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100262026B1 (ko) * | 1994-10-04 | 2000-07-15 | 제이 엘. 차스킨, 버나드 스나이더, 아더엠. 킹 | 페놀타르 폐기물의 환원방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| US11407694B2 (en) | 2022-08-09 |
| JP2021503436A (ja) | 2021-02-12 |
| EP3680226A4 (en) | 2020-12-23 |
| WO2019098501A1 (ko) | 2019-05-23 |
| EP3680226A1 (en) | 2020-07-15 |
| KR20190058273A (ko) | 2019-05-29 |
| EP3680226B1 (en) | 2023-10-25 |
| JP7104707B2 (ja) | 2022-07-21 |
| WO2019098501A8 (ko) | 2019-09-12 |
| CN110461806A (zh) | 2019-11-15 |
| US20210130256A1 (en) | 2021-05-06 |
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