KR840000460A - 큐멘 산화생성물의 분해공정 - Google Patents

큐멘 산화생성물의 분해공정 Download PDF

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KR840000460A
KR840000460A KR1019820002607A KR820002607A KR840000460A KR 840000460 A KR840000460 A KR 840000460A KR 1019820002607 A KR1019820002607 A KR 1019820002607A KR 820002607 A KR820002607 A KR 820002607A KR 840000460 A KR840000460 A KR 840000460A
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reaction mixture
mixture
dicumyl peroxide
cumene
temperature
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KR1019820002607A
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KR850001469B1 (ko
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시프니아데스 스틸리아노스 (외 2)
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로이 에이취. 멧신길
알라이드 코오포레이션
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C27/00Processes involving the simultaneous production of more than one class of oxygen-containing compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C409/00Peroxy compounds
    • C07C409/16Peroxy compounds the —O—O— group being bound between two carbon atoms not further substituted by oxygen atoms, i.e. peroxides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/08Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/02Compounds 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
    • C07C39/04Phenol
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C407/00Preparation of peroxy compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/517Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/53Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/52Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

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

Abstract

내용 없음

Description

큐멘 산화생성물의 분해공정
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
제1도는 본 발명의 공정도. 제2도는 여러온도에서의 반응시간에 따른 비반응 DCP의 퍼셀트와 생성 AMS의 수율을 표시한 그래프.

Claims (8)

  1. 다음 단계들을 포함하여, 큐멘 하이드로퍼옥사이드(CHP) 및 디메틸페닐 카비놀(DMPC)을 포함하는 큐멘산화 생성물을 분해하여 페놀, 아세톤 및 알파-메틸스티렌(AMS)을 제조하는 공정 :
    a) 반응혼합물의 약 0.4-4.5wt 정도되는 물 존재하의 역혼합 반응조에서 큐멘산화생성물을 산촉매와 함께 혼합한 후, 역혼합 반응 혼합물의 CHP 농도를 약 0.5-5.0wt%로 감소시키고 큐멘산화물 혼합물 중의 DMPC의 최소한 40% 이상을 디큐밀 퍼옥사이드(DCP)로 전환하기에 충분한 시간동안 온도를 약 50-90℃로 유지시킴.
    b) 반응혼합물을, 플러그 흐름 조건하에서, 약 0.4wt% 이하의 CHP 농도를 갖는 2차혼합물을 형성하기에 충분한 시간동안 약 50-90℃에서 반응시킴.
    c) 상기 2차혼합물을, 플러그 흐름 조건하에서, 최소한 90% 이상의 DCP를 AMS, 페놀 및 아세톤으로 전환시키기에 충분한 시간동안 약 120-150℃에서 반응시킴.
  2. 역혼합 반응혼합물이 약 0.8-1.5%의 수분 및 130-100ppm의 이산화황 또는 황산을 포함하며 60-80℃로 유지 되는, 주장 1의 공정.
  3. 단계(b)의 반응시간이 CHP 능도를 0.2% 이하로 낮추기에 충분한 정도인, 주장 1의 공정.
  4. 단계(b)로부터의 생성물을 단계(c)의 온도에서 30추이하동안 플러그 흐름조건하에 가열시킨뒤 이어 최소한 30초동안 그 온도를 유지시킴을 특징으로하는, 주장 1의 공정.
  5. 단계(c)동안 DCP 농도를 측정하여 이차반응혼합물중에 약 0.5-5%의 DCP가 미전환 잔류할때 반응 혼합물을 100℃이하로 냉각시키는 단계를 부가적으로 포함하는, 주장 1의 공정.
  6. 다음 단계를 포함하여, 페놀-아세톤-큐멘용액에서 알피-메틸스티렌을 제조하는 방법.
    a) 페놀, 아세톤, 큐멘 및 디큐밀 퍼옥사이드를 포함하는 일차혼합물을 플러그 흐름 조건하에서 120-150℃로 가열함. b) 디큐밀 퍼옥사이드의 능도를 측정함. c) 디큐밀 퍼옥사이드의 농도가 일차혼합물의 디큐밀 퍼옥사이드 농도의 약 0.5-5.0%가 되었을 때 반응혼합물이 100℃ 이하로 냉각하여 알피-메틸스티렌으로부터의 부산물생성을 감소시킴.
  7. 상기 단계(b)가 반응혼합물의 분취량(aliquot)을 기체크로마토그래피로 분석하여 디큐밀 퍼옥사이드 피크의 면적을 측정하는 것을 포함 하는, 주장 6의 방법.
  8. 상기 일차혼합물을 상기온도에서 30초이하동안 가열한후부가적으로 최소한 30초동안 그 온도를 유지시킴을 특징으로 하는, 주장 6 또는 7의 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR8202607A 1981-06-22 1982-06-11 큐멘 산화생성물의 분해공정 KR850001469B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US276,223 1981-06-22
US06/276,233 US4358618A (en) 1981-06-22 1981-06-22 Decomposition of cumene oxidation product
US276223 1994-07-15

Publications (2)

Publication Number Publication Date
KR840000460A true KR840000460A (ko) 1984-02-22
KR850001469B1 KR850001469B1 (ko) 1985-10-10

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KR8202607A KR850001469B1 (ko) 1981-06-22 1982-06-11 큐멘 산화생성물의 분해공정

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US (1) US4358618A (ko)
JP (1) JPS5832831A (ko)
KR (1) KR850001469B1 (ko)
CA (1) CA1178616A (ko)
DE (1) DE3222533A1 (ko)
GB (1) GB2100730B (ko)
IT (1) IT1156366B (ko)
MX (1) MX165355B (ko)

Families Citing this family (55)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4567304A (en) * 1983-04-05 1986-01-28 General Electric Company Process for preparing acetone and phenol
US7166752B2 (en) * 1989-01-17 2007-01-23 Sunoco, Inc. (R&M) Decomposition of cumene oxidation product
JPH04119106U (ja) * 1991-04-10 1992-10-26 株式会社村田製作所 方向性結合器
US5245090A (en) * 1992-09-11 1993-09-14 Aristech Chemical Corporation Two-stage cleavage of cumene hydroperoxide
US5254751A (en) 1992-09-14 1993-10-19 General Electric Company Method for the decomposition of cumene hydroperoxide by acidic catalyst to phenol and acetone
CA2127375A1 (en) * 1992-11-05 1994-05-11 Shintaro Araki Process for producing aromatic hydroxylic compound
US5371305A (en) * 1992-12-31 1994-12-06 Hercules Incorporated Process for producing phenol from cumene
JP3711504B2 (ja) * 1994-03-01 2005-11-02 ゼネラル・エレクトリック・カンパニイ 工業用クメンヒドロペルオキシドのフェノール、アセトン及びα−メチルスチレンへの酸分解方法
CN1061969C (zh) * 1994-03-01 2001-02-14 通用电气公司 工业级枯烯过氧化氢酸性裂解生产苯酚、丙酮和α-甲基苯乙烯的方法
US5457244A (en) * 1994-10-04 1995-10-10 General Electric Company Phenol tar waste reduction process
TW318174B (ko) * 1994-11-04 1997-10-21 Gen Electric
CA2161995A1 (en) * 1994-11-23 1996-05-24 Arkady S. Dyckman Method of phenol tar desalting
US5510543A (en) * 1994-12-09 1996-04-23 General Electric Company Removal and neutralization of acid catalyst from products of cumene hydroperoxide cleavage
US5463136A (en) * 1994-12-22 1995-10-31 Shell Oil Company Cumene hydroperoxide cleavage process
JP3769050B2 (ja) * 1995-07-07 2006-04-19 三井化学株式会社 フェノールの製造方法
DE69525248T2 (de) 1995-08-23 2002-09-26 Toshiba Tungaloy Co. Ltd., Kawasaki Flächen-kristallines Wolframkarbid enthaltendes Hartmetall, Zusammensetzung zur Herstellung von flächen-kristallines Wolframkarbid und Verfahren zur Herstellung des Hartmetalls
US5672774A (en) * 1995-10-24 1997-09-30 General Electric Company Phenol tar processing method
US5962751A (en) * 1996-04-26 1999-10-05 General Electric Company Phenol tar desalting method
RU2125038C1 (ru) * 1996-09-24 1999-01-20 Закошанский Владимир Михайлович Безотходный экономичный способ получения фенола и ацетона
RU2141938C1 (ru) 1996-12-15 1999-11-27 ООО "Илла Интернешнл", Лтд. Энергосберегающий и высокоселективный способ получения фенола и ацетона (процесс иф-96)
AU6135999A (en) * 1998-09-04 2000-03-27 Illa International L.L.C. High selective method of phenol and acetone production
AU2001241836A1 (en) * 2000-03-03 2001-09-17 Illa International L.L.C. Method of producing cumene hydroperoxide, phenol and acetone
DE10021482A1 (de) * 2000-05-03 2001-11-08 Phenolchemie Gmbh & Co Kg Verfahren zur thermischen Nachbehandlung von Spaltprodukt aus der säurekatalysierten Spaltung von Cumolhydroperoxid
DE10051581A1 (de) * 2000-10-18 2002-06-20 Phenolchemie Gmbh & Co Kg Verfahren zur Spaltung von Alkylarylhydroperoxiden
DE10110392A1 (de) * 2001-03-03 2002-09-12 Phenolchemie Gmbh & Co Kg Verfahren zur Herstellung von Phenolen
DE10111889A1 (de) * 2001-03-13 2002-10-02 Phenolchemie Gmbh & Co Kg Verfahren zur säurekatalysierten Spaltung von Cumolhydroperoxid
US6825387B2 (en) * 2002-10-15 2004-11-30 Kellogg Brown & Root, Inc. Low sodium cleavage product
US6984761B2 (en) * 2002-12-16 2006-01-10 Exxonmobil Chemical Patents Inc. Co-production of phenol, acetone, α-methylstyrene and propylene oxide, and catalyst therefor
US7312365B2 (en) * 2003-02-14 2007-12-25 Shell Oil Company Process for low temperature cleavage of an oxidation mixture comprising hydroperoxides
US7141703B2 (en) * 2003-02-14 2006-11-28 Shell Oil Company Process for producing phenol and ketone using neutralizing base
US7282613B2 (en) * 2003-02-14 2007-10-16 Shell Oil Company Process for producing phenol and methyl ethyl ketone
EP1641732B1 (en) * 2003-07-04 2008-02-13 INEOS Phenol GmbH & Co. KG Process for the preparation of phenolic compounds, for separating phenol from cleavage product mixtures, and an apparatus
US7626060B2 (en) * 2003-07-11 2009-12-01 INEOS Phenol GmbH & Co., KG Process for the preparation of phenolic compounds, for separating phenol from cleavage product mixtures, and an apparatus
EP1732869A1 (en) * 2004-03-31 2006-12-20 General Electric Company A Corporation of the State of New York Process for producing phenol
US7141701B1 (en) * 2005-08-19 2006-11-28 Uop Llc Decomposition of cumene hydroperoxide
US7141700B1 (en) * 2005-08-19 2006-11-28 Uop Llc Decomposition of cumene hydroperoxide
WO2007137020A2 (en) * 2006-05-16 2007-11-29 Shell Oil Company Method for decomposing di(phenylalkyl)peroxides to produce hydroxybenzenes and phenylalkenes using solid catalysts
WO2007137021A2 (en) * 2006-05-16 2007-11-29 Shell Oil Company Catalysts comprising a combination of oxidized metals and a method for cleaving phenylalkyl hydroperoxides using the catalysts
US7417003B2 (en) * 2006-12-29 2008-08-26 Uop Llc Solid acid catalyst and process for decomposition of cumene hydroperoxide
US7888537B2 (en) 2006-12-29 2011-02-15 Uop Llc Solid acid catalyst and process for decomposition of cumene hydroperoxide
JP5486010B2 (ja) 2008-10-10 2014-05-07 エクソンモービル・ケミカル・パテンツ・インク フェノールの製造方法
WO2010098916A2 (en) 2009-02-26 2010-09-02 Exxonmobil Chemical Patents Inc. Process for producing phenol
US9321710B2 (en) 2010-01-25 2016-04-26 Exxonmobil Chemical Patents Inc. Process for producing phenol
US20110306800A1 (en) * 2010-06-09 2011-12-15 Scott Roy Keenan Method for the decomposition of cumene hydroperoxide
WO2012036824A1 (en) 2010-09-14 2012-03-22 Exxonmobil Chemical Patents Inc. Oxidation of alkylbenzenes and cycloalkylbenzenes
CN105646156B (zh) 2010-09-14 2018-07-13 埃克森美孚化学专利公司 用于制备苯酚的方法
EP2616421A2 (en) 2010-09-14 2013-07-24 ExxonMobil Chemical Patents Inc. Processes for producing phenol
EP2616422A1 (en) 2010-09-14 2013-07-24 ExxonMobil Chemical Patents Inc. Processes for producing phenol
US9388102B2 (en) 2011-04-19 2016-07-12 Exxonmobil Chemical Patents Inc. Process for producing phenol
SG194008A1 (en) 2011-04-19 2013-11-29 Exxonmobil Chem Patents Inc Process for producing phenol
US9249078B2 (en) 2011-10-07 2016-02-02 Exxonmobil Chemical Patents Inc. Mixed metal oxide catalysts and use thereof
US9278897B2 (en) 2012-09-17 2016-03-08 Exxonmobil Chemical Patents Inc. Process for producing phenol and/or cyclohexanone from cyclohexylbenzene
SG11201503421WA (en) 2012-12-06 2015-05-28 Exxonmobil Chem Patents Inc Process for producing phenol
WO2014088842A1 (en) 2012-12-06 2014-06-12 Exxonmobil Chemical Patents Inc. Process for producing phenol
US9193652B2 (en) 2014-03-04 2015-11-24 Kellogg Brown & Root Llc Phenol resin treatment improvement

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2668180A (en) * 1950-07-01 1954-02-02 Hercules Powder Co Ltd Preparation of aryldialkyl peroxides
US2757209A (en) * 1951-04-26 1956-07-31 Allied Chem & Dye Corp Recovery of phenol and alphamethylstyrene from cumene oxidation reaction mixtures
US2761877A (en) * 1951-05-17 1956-09-04 Rhone Poulenc Sa Production of phenols and carbonyl compounds
US3497561A (en) * 1967-06-08 1970-02-24 Lummus Co Decomposition of hydroperoxides
US4207264A (en) * 1969-10-29 1980-06-10 The Goodyear Tire & Rubber Company Rearrangement of aralkyl hydroperoxides to form phenols and carbonyl compounds
US4016213A (en) * 1971-05-03 1977-04-05 Allied Chemical Corporation Recovery of phenol, acetone and dimethyl phenyl carbinol from cumene oxidation product
EP0018159B1 (en) * 1979-04-20 1983-05-11 Imperial Chemical Industries Plc Process for the production of phenol, acetone and alpha methylstyrene
US4333801A (en) * 1981-08-03 1982-06-08 Uop Inc. Recovery of a cumene/alpha-methylstyrene fraction from a mixture thereof with phenol and water

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Publication number Publication date
GB2100730A (en) 1983-01-06
IT8267783A0 (it) 1982-06-21
GB2100730B (en) 1985-08-14
JPH0251408B2 (ko) 1990-11-07
JPS5832831A (ja) 1983-02-25
MX165355B (es) 1992-11-05
CA1178616A (en) 1984-11-27
US4358618A (en) 1982-11-09
KR850001469B1 (ko) 1985-10-10
IT1156366B (it) 1987-02-04
DE3222533C2 (ko) 1990-11-29
DE3222533A1 (de) 1983-01-13

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