KR900007770A - 방향족 화합물의 알킬화에 의한 큐멘 제조방법 및 그 큐멘에 의한 페놀 제조방법 - Google Patents

방향족 화합물의 알킬화에 의한 큐멘 제조방법 및 그 큐멘에 의한 페놀 제조방법 Download PDF

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KR900007770A
KR900007770A KR1019890017325A KR890017325A KR900007770A KR 900007770 A KR900007770 A KR 900007770A KR 1019890017325 A KR1019890017325 A KR 1019890017325A KR 890017325 A KR890017325 A KR 890017325A KR 900007770 A KR900007770 A KR 900007770A
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cumene
isopropanol
acetone
benzene
phenol
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KR1019890017325A
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KR0149008B1 (ko
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신다로오 아라끼
후지히사 마쓰나가
히로시 후꾸하라
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다께바야시 쇼오고
미쓰이세끼유 가가꾸고요교오 가부시끼가이샤
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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
    • C07C409/00—Peroxy compounds
    • C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
    • C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
    • C07C409/08—Compounds containing six-membered aromatic rings
    • C07C409/10—Cumene hydroperoxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
    • C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
    • C07C2/66—Catalytic processes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
    • C07C2/862—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms
    • C07C2/864—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms the non-hydrocarbon is an alcohol
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C407/00—Preparation of peroxy compounds
    • 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
    • C07C45/53—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 of hydroperoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
    • Y—GENERAL 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

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

Abstract

내용 없음

Description

방향족 화합물의 알킬화에 의한 큐멘 제조방법 및 그 큐멘에 의한 페놀 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
제1도는 본 발명의 실시에 사용되는 반응계의 개략도.

Claims (10)

  1. (a-1) 벤젠을 이소프로판올로 알킬화하여 큐멘을 합성하는 단계, (b) 상기 단계(a-1)에서 얻은 큐멘을 산화시켜 큐멘하이드로 퍼옥사이드를 얻는 단계, (c) 상기 큐멘하이드로 퍼옥사이드를 산분열시켜 페놀과 아세톤을 얻는 단계, 및 (d) 상기 단계 (c)에서 얻은 아세톤을 수소화하여, 상기 단계 (a-1)로 제순환될 이소프로판올을 얻는 단계를 포함하는 것을 특징으로 하는 페놀의 제조방법.
  2. (a-2) 벤젠을 이소프로판올과 프로필렌으로 알킬화하여 큐멘을 합성하는 단계, (b) 상기 단계 (a-2)에서 얻은 큐멘을 산화시켜 큐멘하이드로 퍼옥사이드를 얻는 단계, (c) 상기 큐멘하이드로 퍼옥사이드를 산분열시켜 페놀과 아세톤을 얻는 단계, 및 (d) 상기 단계 (c)의 아세톤을 수소화하여, 단계 (a-2)로 재순환될 이소프로판올 얻는 단계를 포함하는 것이 특징인 페놀의 제조방법.
  3. (a-3) 벤젠과 프로필렌을 반응시켜 큐멘을 합성하는 단계, (b-2) 상기 단계 (a-3) 및/또는 하기단계 (a-4)에서 얻는 큐멘을 산화시켜 큐멘하이드로 퍼옥사이드를 얻는 단계, (c) 상기 큐멘하이드로 퍼옥사이드를 산분열시켜 페놀과 아세톤을 얻는 단계, (d) 상기 단계(c)에서 얻은 아세톤을 수소화하여 이소프로판올을 얻는 단계, 및 (a-4) 벤젠을, 이소프로판올 또는 이소프로판올과 프로필렌과의 혼합물로 알킬화하여 상기 단계 (b-2)로 재순환될 큐멘을 합성하는 단계를 포함하는 것이 특징인 페놀의 제조방법.
  4. 제1항, 2항 또는 제3항에서, 상기 알킬화반응을 제올라이트 촉매존재하에서 행하는 것이 특징인 페놀의 제조방법.
  5. 제4항에서, 상기 제올라이트가, 실리카대 알루미나 비가 4~10미만인 양자교환 Y형 골격 제올라이트인 것이 특징인 페놀의 제조방법.
  6. 제1항, 2항 또는 3항에서, 벤젠대 이소프로판올, 또는 이소프로판올과 프로필렌과의 혼합물의 몰비가 1/10~10/1의 범위내인 것이 특징인 페놀의 제조방법.
  7. 제1항, 2항 또는 제3항에서, 상기 알킬화반응을 150~350℃범위의 온도에서 행하는 것이 특징인 페놀의 제조방법.
  8. 제1항, 2항 또는 제3항에서, 한 반응기 내에서 이소프로판올에 의한 벤젠의 알킬화반응이, 올레핀을 함유하는 반응혼합물을, 제1부분과 제2부분의 비가 1보다 크도록 상기 반응기로부터 제1부분과 제2부분으로 분리하는 단계와, 상기 제1부분을 상기 반응기로 재순환시키는 단계, 및 상기 잔류하는 제2부분을 상기 반응계로부터 반응 생성 혼합물로서 취출하므로써, 이소프로판올에 의한 올레핀 부생물의 생성을 최소화하는 동시에 알킬화수율(%)을 높이는 단계를 포함하는 것이 특징인 페놀의 제조방법.
  9. 제8항에서, 상기 제1부분 대 제2부분의 비율이 2/1~100/1의 범위내인 것이 특징인 페놀의 제조방법.
  10. 제1항, 2항 또는 제3항에서, 상기 단계(d)의 실온~200℃의 온도에서 수소화 반응을 실온~200℃의 온도에서 행하는 것이 특징인 페놀의 제조방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019890017325A 1988-11-28 1989-11-28 방향족 화합물의 알킬화에 의한 큐멘 제조방법 및 그 큐멘에 의한 페놀 제조방법 KR0149008B1 (ko)

Applications Claiming Priority (9)

Application Number Priority Date Filing Date Title
JP63-300300 1988-11-28
JP30030088 1988-11-28
JP88-300300 1988-11-28
JP88-302617 1988-11-30
JP63-302617 1988-11-30
JP63302617A JP2593212B2 (ja) 1988-11-30 1988-11-30 クメンの製造方法
JP63328722A JP2603711B2 (ja) 1988-12-26 1988-12-26 クメンの製造方法
JP63-328722 1988-12-26
JP88-328722 1988-12-26

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KR900007770A true KR900007770A (ko) 1990-06-01
KR0149008B1 KR0149008B1 (ko) 1998-10-15

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Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1313007B1 (it) * 1999-07-13 2002-05-29 Enichem Spa Processso per l'alchilazione di composti aromatici in fase gas.
IT1313008B1 (it) * 1999-07-13 2002-05-29 Enichem Spa Processo per l'alchilazione di composti aromatici.
DE10008924A1 (de) * 2000-02-25 2001-09-06 Phenolchemie Gmbh & Co Kg Verfahren zur Herstellung von Phenol
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
WO2008062644A1 (en) 2006-11-21 2008-05-29 Mitsui Chemicals, Inc. Method for producing alkylated aromatic compound and method for producing phenol
KR101044481B1 (ko) 2007-02-23 2011-06-27 미쓰이 가가쿠 가부시키가이샤 알킬화 방향족 화합물의 제조방법
JP5255318B2 (ja) * 2007-04-18 2013-08-07 三井化学株式会社 アルキル化芳香族化合物の製造方法およびフェノールの製造方法
US8273932B2 (en) 2008-06-10 2012-09-25 Mitsui Chemicals, Inc. Process for producing alkylated aromatic compounds and process for producing phenol
EP2298718B1 (en) 2008-06-10 2018-03-28 Mitsui Chemicals, Inc. Methods for producing cumene and phenol
KR20110082156A (ko) * 2008-10-06 2011-07-18 바져 라이센싱 엘엘씨 큐멘의 제조방법
TWI436969B (zh) 2008-10-23 2014-05-11 Mitsui Chemicals Inc 烷基化芳香族化合物之製造方法，異丙苯之製造方法及酚之製造方法
SG174409A1 (en) 2009-03-19 2011-10-28 Mitsui Chemicals Inc Process for producing alkylated aromatic compounds and process for producing phenols
WO2014011359A1 (en) * 2012-07-13 2014-01-16 Badger Licensing Llc Process for producing phenol

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5211511B2 (ko) * 1972-06-01 1977-03-31
US4393262A (en) * 1978-12-14 1983-07-12 Mobil Oil Corporation Production of isopropylbenzene
JPS58216128A (ja) * 1982-06-11 1983-12-15 Mitsui Petrochem Ind Ltd モノアルキルベンゼンの製法

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JPH02231442A (ja) 1990-09-13

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