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KR900007770A - Method for preparing cumene by alkylation of aromatic compounds and method for producing phenol by cumene - Google Patents

Method for preparing cumene by alkylation of aromatic compounds and method for producing phenol by cumene 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 (en
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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 없음No content

Description

방향족 화합물의 알킬화에 의한 큐멘 제조방법 및 그 큐멘에 의한 페놀 제조방법Method for preparing cumene by alkylation of aromatic compounds and method for producing phenol by cumene

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

제1도는 본 발명의 실시에 사용되는 반응계의 개략도.1 is a schematic diagram of a reaction system used in the practice of the present invention.

Claims (10)

(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.(a-1) alkylating benzene with isopropanol to synthesize cumene, (b) oxidizing the cumene obtained in step (a-1) to obtain cumene hydroperoxide, (c) the cumene hydroperoxide Acid cleavage to obtain phenol and acetone, and (d) hydrogenation of the acetone obtained in step (c) to obtain isopropanol to be recycled to step (a-1). Manufacturing method. (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.(a-2) alkylating benzene with isopropanol and propylene to synthesize cumene, (b) oxidizing the cumene obtained in step (a-2) to obtain cumene hydroperoxide, (c) the cumene hydroperoxide Obtaining phenol and acetone by acid cleaving oxide, and (d) Hydrogenating the acetone of step (c), obtaining isopropanol to be recycled to step (a-2). (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.(a-3) synthesizing cumene by reacting benzene and propylene; (b-2) cumene hydroperoxide is obtained by oxidizing cumene obtained in the above step (a-3) and / or following step (a-4). Obtaining (c) acid cleaving the cumene hydroperoxide to obtain phenol and acetone, (d) hydrogenating the acetone obtained in step (c) to obtain isopropanol, and (a-4) benzene, Alkylating with isopropanol or a mixture of isopropanol and propylene to synthesize cumene to be recycled to step (b-2). 제1항, 2항 또는 제3항에서, 상기 알킬화반응을 제올라이트 촉매존재하에서 행하는 것이 특징인 페놀의 제조방법.The method for producing phenol according to claim 1, 2 or 3, wherein the alkylation reaction is carried out in the presence of a zeolite catalyst. 제4항에서, 상기 제올라이트가, 실리카대 알루미나 비가 4~10미만인 양자교환 Y형 골격 제올라이트인 것이 특징인 페놀의 제조방법.5. The method according to claim 4, wherein the zeolite is a proton exchange Y-type framework zeolite having a silica to alumina ratio of less than 4 to 10. 제1항, 2항 또는 3항에서, 벤젠대 이소프로판올, 또는 이소프로판올과 프로필렌과의 혼합물의 몰비가 1/10~10/1의 범위내인 것이 특징인 페놀의 제조방법.The method for producing phenol according to claim 1, 2 or 3, wherein the molar ratio of benzene to isopropanol or a mixture of isopropanol and propylene is in the range of 1/10 to 10/1. 제1항, 2항 또는 제3항에서, 상기 알킬화반응을 150~350℃범위의 온도에서 행하는 것이 특징인 페놀의 제조방법.The method for producing phenol according to claim 1, 2 or 3, wherein the alkylation reaction is performed at a temperature in the range of 150 to 350 ° C. 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.4. The process according to claim 1, 2 or 3, wherein the alkylation of benzene with isopropanol in one reactor results in the reaction mixture containing olefin being removed from the reactor such that the ratio of the first portion and the second portion is greater than one. Separation of the first and second portions, recycling the first portion to the reactor, and withdrawing the remaining second portion from the reaction system as a reaction product mixture to produce olefin by-products with isopropanol Method of producing a phenol, characterized in that it comprises a step of increasing the alkylation yield (%) at the same time to minimize. 제8항에서, 상기 제1부분 대 제2부분의 비율이 2/1~100/1의 범위내인 것이 특징인 페놀의 제조방법.9. The method of claim 8, wherein the ratio of the first portion to the second portion is in the range of 2/1 to 100/1. 제1항, 2항 또는 제3항에서, 상기 단계(d)의 실온~200℃의 온도에서 수소화 반응을 실온~200℃의 온도에서 행하는 것이 특징인 페놀의 제조방법.The method for producing phenol according to claim 1, 2 or 3, wherein the hydrogenation reaction is carried out at a temperature of room temperature to 200 ° C in the step (d). ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019890017325A 1988-11-28 1989-11-28 Preparation of cumene through alkylation of an aromatic compound and preparation of penol through cumene Expired - Lifetime KR0149008B1 (en)

Applications Claiming Priority (9)

Application Number Priority Date Filing Date Title
JP63-300300 1988-11-28
JP88-300300 1988-11-28
JP30030088 1988-11-28
JP88-302617 1988-11-30
JP63302617A JP2593212B2 (en) 1988-11-30 1988-11-30 How to make cumene
JP63-302617 1988-11-30
JP63-328722 1988-12-26
JP88-328722 1988-12-26
JP63328722A JP2603711B2 (en) 1988-12-26 1988-12-26 How to make cumene

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

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1313007B1 (en) * 1999-07-13 2002-05-29 Enichem Spa PROCESS FOR THE ALKYLATION OF AROMATIC COMPOUNDS IN THE GAS PHASE.
IT1313008B1 (en) * 1999-07-13 2002-05-29 Enichem Spa PROCESS FOR THE ALKYLATION OF AROMATIC COMPOUNDS.
DE10008924A1 (en) * 2000-02-25 2001-09-06 Phenolchemie Gmbh & Co Kg Process for the production of 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
US8581016B2 (en) 2006-11-21 2013-11-12 Mitsui Chemicals, Inc. Process for producing alkylated aromatic compound and process for producing phenol
KR101044481B1 (en) 2007-02-23 2011-06-27 미쓰이 가가쿠 가부시키가이샤 Method for preparing alkylated aromatic compound
JP5255318B2 (en) * 2007-04-18 2013-08-07 三井化学株式会社 Method for producing alkylated aromatic compound and method for producing phenol
CN102056869B (en) 2008-06-10 2013-09-18 三井化学株式会社 Method for producing an alkylated aromatic compound and method for producing phenol
EP2298718B1 (en) 2008-06-10 2018-03-28 Mitsui Chemicals, Inc. Methods for producing cumene and phenol
EP2346798A2 (en) * 2008-10-06 2011-07-27 Badger Licensing, LLC Process for producing cumene
TWI436969B (en) * 2008-10-23 2014-05-11 Mitsui Chemicals Inc Method for producing alkylated aromatic compound, method for producing cumene and method for producing phenol
WO2010106967A1 (en) 2009-03-19 2010-09-23 三井化学株式会社 Method for producing alkylated aromatic compound and method for producing phenol
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 (en) * 1972-06-01 1977-03-31
US4393262A (en) * 1978-12-14 1983-07-12 Mobil Oil Corporation Production of isopropylbenzene
JPS58216128A (en) * 1982-06-11 1983-12-15 Mitsui Petrochem Ind Ltd Preparation of monoalkylbenzene

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JPH02231442A (en) 1990-09-13

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