US20110306800A1 - Method for the decomposition of cumene hydroperoxide - Google Patents

Method for the decomposition of cumene hydroperoxide Download PDF

Info

Publication number
US20110306800A1
US20110306800A1 US12/797,321 US79732110A US2011306800A1 US 20110306800 A1 US20110306800 A1 US 20110306800A1 US 79732110 A US79732110 A US 79732110A US 2011306800 A1 US2011306800 A1 US 2011306800A1
Authority
US
United States
Prior art keywords
stage
temperature
residence time
acetone
phenol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US12/797,321
Other languages
English (en)
Inventor
Scott Roy Keenan
Michael Keith Hagans
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Honeywell International Inc
Original Assignee
Honeywell International Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Honeywell International Inc filed Critical Honeywell International Inc
Priority to US12/797,321 priority Critical patent/US20110306800A1/en
Priority to BR112012031216A priority patent/BR112012031216A2/pt
Priority to PCT/US2011/039068 priority patent/WO2011156227A2/en
Priority to EP11792928.1A priority patent/EP2580181B1/en
Priority to RU2012156422/04A priority patent/RU2562236C2/ru
Priority to CA2802092A priority patent/CA2802092A1/en
Priority to KR1020127033746A priority patent/KR101804596B1/ko
Priority to CN201180028747.2A priority patent/CN103108855B/zh
Priority to SG2012090379A priority patent/SG186237A1/en
Priority to JP2013514234A priority patent/JP5793187B2/ja
Assigned to HONEYWELL INTERNATIONAL INC. reassignment HONEYWELL INTERNATIONAL INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SUNOCO, INC. (R&M)
Publication of US20110306800A1 publication Critical patent/US20110306800A1/en
Priority to US13/432,141 priority patent/US8247616B1/en
Abandoned legal-status Critical Current

Links

Images

Classifications

    • 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
    • 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
    • C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C27/00—Processes involving the simultaneous production of more than one class of oxygen-containing compounds
    • 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
    • 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
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/08—Acetone
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
    • C07C2527/053—Sulfates or other compounds comprising the anion (SnO3n+1)2-
    • C07C2527/054—Sulfuric acid or other acids with the formula H2Sn03n+1
    • 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

Definitions

  • the present invention relates to an improved method for the production of phenol, acetone and alpha-methyl styrene (AMS) from a cumene hydroperoxide and dimethylbenzyl alcohol (DMBA) mixture.
  • AMS alpha-methyl styrene
  • DMBA dimethylbenzyl alcohol
  • DMBA dimethylbenzyl alcohol
  • AMS alpha-methyl styrene
  • a key to the two stage approach is to use a lower temperature first stage, targeting the selective decomposition of CHP into phenol and acetone while maximizing preservation of DMBA (and ultimately the AMS product from it) as dicumyl peroxide (DCP).
  • the second stage is typically run shorter and hotter to selectively decompose the DCP into phenol, acetone and AMS, and dehydrate the residual DMBA from the first stage to AMS.
  • the present invention relates to a method for the production of phenol, acetone, and alpha-methyl styrene from a mixture of cumene hydroperoxide and dimethylbenzyl alcohol wherein the first stage is carried out with an acetone to phenol mole ratio of 1.0-1.5, water content of 0.5 to 1.5 wt. %, sulfuric acid concentration of 20-400 ppm, a reactor pressure of 500-760 mmHg, and a temperature of 60-85° C., being optimized to maximize the yield of dicumyl peroxide from cumene hydroperoxide and dimethylbenzyl alcohol under any specific set of feed and operational conditions. Additional water, 0.5 to 5 wt.
  • % is then added prior to the second stage which is maintained preferably at 130-140° C., regardless of residence time by controlling the rate of water addition. Water addition at a fixed temperature is then further refined to minimize residual dicumyl peroxide and maximize overall dimethylbenzyl alcohol to alpha-methyl styrene yield.
  • FIG. 1 is a graph of AMS yield and second stage residual DCP versus temperature, with and without approximately 2% additional water added.
  • the decomposition process is run at higher temperatures, e.g., 110-150° C., most preferably in the range of 130-140° C., and shorter times to balance maximum yield against the rate of organic fouling and the thermal decomposition of DCP, so as to give additional DMBA equivalents.
  • Yield is optimized in the second stage by monitoring residual DCP and DMBA and targeting levels that have been established as representing optimum yield at a given feed composition to, and operation of, the first stage.
  • a method for the production of phenol, acetone and alpha-methyl styrene from a mixture of cumene hydroperoxide and dimethylbenzyl alcohol wherein the first stage is carried out with an acetone to phenol mole ratio of about 1.2-1.5, a water content of about 1.0-1.5 wt. %, sulfuric acid concentration of about 300-350 ppm, a reactor pressure of about 500-600 mm Hg, a temperature of about 75-81° C., and a 5-6 minute residence time, mixing being provided via vigorous boiling of the mixture and return of the subsequently condensed volatiles.
  • FIG. 1 The results in FIG. 1 were generated using a well stirred glass reactor that was charged with 15 ml of a solution of 1/1 molar phenol/acetone spiked with approximately 8.2% DCP, 1.3% DMBA, 1.4% AMS, 12% cumene, and sufficient water added to give either 1.3% or 3.3% water content.
  • the solution was brought to target temperature, and 8 ⁇ L of 0.5 molar sulfuric acid added (approximately 25 ppm in the bulk reaction) to start the reaction. Samples were taken at various times, neutralized with a small amount of base, and analyzed for a complete component profile.
  • a CHP-containing stream with 80% CHP, 3.6% DMBA, 0.4% acetophenone (AP), and the residual cumene was fed to the back mixed first stage of a commercial CHP decomposer operating under conditions of vigorous boiling at 550-600 mm Hg pressure, 78-80° C., a 1.25-1.35 mole ratio of acetone to CHP, 5-6 minute residence time, 300-350 ppm of sulfuric acid, and 1.0-1.3 wt. % water under optimum conditions. With no additional water added ahead of a plug flow second stage with 0.8-1.0 minutes of residence time, an average AMS yield of 80.8% was obtained at 108 C, with 0.09 to 0.12 wt. % DCP, and 0.16 to 0.18% DMBA residuals exiting the second stage.
  • a method for the production of phenol, acetone and alpha-methyl styrene from a mixture of cumene hydroperoxide and dimethylbenzyl alcohol which comprises a first stage reaction with an acetone to phenol mole ratio of about 1.0-1.5, a water content of about 0.5 to 1.5 wt. %, a sulfuric acid concentration of about 20-400 ppm, a reactor pressure of about 450-760 mm Hg, a temperature of about 60-85° C., and a residence time of 4-45 minutes, with about 0.5 to 3 wt. % additional water then being added prior to a plug flow, and a second stage reactor maintained at about 110-150° C.
  • the first stage reaction conditions are about 300-350 ppm sulfuric acid, about 450-500 mm Hg operating pressure, about 78-80° C. operating temperature, and a 5-6 minute residence time, the acetone to phenol mole ratio being about 1.25 to 1.35, and the water content being about 1.0-1.2 wt. % in the first stage, and the second stage reaction conditions are a residence time of 0.7 to 1.0 minutes, about 1-2 wt. % additional added water, and a temperature of about 120-140° C.
  • exit concentrations of dicumyl peroxide are maintained at about 0.01-0.15 wt. %.
  • the first stage reaction conditions are an acetone to phenol ratio of about 1.0, a sulfuric acid concentration of about 20-50 ppm, atmospheric to slightly negative pressure, and a residence time of 15-45 minutes
  • the second stage reaction conditions are a residence time of 5 to 20 minutes, about 1-2 wt. % additional added water, and a temperature of about 120-140° C., with a temperature of 134-138° C. particularly preferred.
  • exit concentrations of dicumyl peroxide are maintained at about 0.06 to 0.10 wt. %, with about 0.02-0.03 wt. % being particularly preferred.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
US12/797,321 2010-06-09 2010-06-09 Method for the decomposition of cumene hydroperoxide Abandoned US20110306800A1 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
US12/797,321 US20110306800A1 (en) 2010-06-09 2010-06-09 Method for the decomposition of cumene hydroperoxide
CA2802092A CA2802092A1 (en) 2010-06-09 2011-06-03 Method for the decomposition of cumene hydroperoxide
PCT/US2011/039068 WO2011156227A2 (en) 2010-06-09 2011-06-03 Method for the decomposition of cumene hydroperoxide
EP11792928.1A EP2580181B1 (en) 2010-06-09 2011-06-03 Method for the decomposition of cumene hydroperoxide
RU2012156422/04A RU2562236C2 (ru) 2010-06-09 2011-06-03 Способ разложения гидропероксида кумола
BR112012031216A BR112012031216A2 (pt) 2010-06-09 2011-06-03 método para a produção de fenol, acetona e alfa-metil estireno
KR1020127033746A KR101804596B1 (ko) 2010-06-09 2011-06-03 큐멘 하이드로퍼옥사이드의 분해 방법
CN201180028747.2A CN103108855B (zh) 2010-06-09 2011-06-03 用于分解过氧化氢异丙苯的方法
SG2012090379A SG186237A1 (en) 2010-06-09 2011-06-03 Method for the decomposition of cumene hydroperoxide
JP2013514234A JP5793187B2 (ja) 2010-06-09 2011-06-03 クメンヒドロペルオキシドの分解方法
US13/432,141 US8247616B1 (en) 2010-06-09 2012-03-28 Method for the decomposition of cumene hydroperoxide

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US12/797,321 US20110306800A1 (en) 2010-06-09 2010-06-09 Method for the decomposition of cumene hydroperoxide

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US13/432,141 Continuation US8247616B1 (en) 2010-06-09 2012-03-28 Method for the decomposition of cumene hydroperoxide

Publications (1)

Publication Number Publication Date
US20110306800A1 true US20110306800A1 (en) 2011-12-15

Family

ID=45096749

Family Applications (2)

Application Number Title Priority Date Filing Date
US12/797,321 Abandoned US20110306800A1 (en) 2010-06-09 2010-06-09 Method for the decomposition of cumene hydroperoxide
US13/432,141 Active US8247616B1 (en) 2010-06-09 2012-03-28 Method for the decomposition of cumene hydroperoxide

Family Applications After (1)

Application Number Title Priority Date Filing Date
US13/432,141 Active US8247616B1 (en) 2010-06-09 2012-03-28 Method for the decomposition of cumene hydroperoxide

Country Status (10)

Country Link
US (2) US20110306800A1 (ja)
EP (1) EP2580181B1 (ja)
JP (1) JP5793187B2 (ja)
KR (1) KR101804596B1 (ja)
CN (1) CN103108855B (ja)
BR (1) BR112012031216A2 (ja)
CA (1) CA2802092A1 (ja)
RU (1) RU2562236C2 (ja)
SG (1) SG186237A1 (ja)
WO (1) WO2011156227A2 (ja)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013134049A1 (en) * 2012-03-09 2013-09-12 Honeywell International Inc. Method for producing alpha-methyl styrene from cumene
EP3174630A4 (en) * 2014-07-29 2018-04-04 AdvanSix Resins & Chemicals LLC Reactor with baffle configuration
CN114436756A (zh) * 2020-10-16 2022-05-06 中国石油化工股份有限公司 一种制备异丙苯的方法、系统与应用
CN114981232A (zh) * 2020-12-21 2022-08-30 株式会社Lg化学 制备α-甲基苯乙烯的方法

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2757209A (en) * 1951-04-26 1956-07-31 Allied Chem & Dye Corp Recovery of phenol and alphamethylstyrene from cumene oxidation reaction mixtures
US4358618A (en) 1981-06-22 1982-11-09 Allied Corporation Decomposition of cumene oxidation product
US7166752B2 (en) * 1989-01-17 2007-01-23 Sunoco, Inc. (R&M) Decomposition of cumene oxidation product
RU2068404C1 (ru) * 1992-07-15 1996-10-27 Грозненский химический комбинат Способ совместного получения фенола, ацетона и альфа-метилстирола
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
US5371305A (en) 1992-12-31 1994-12-06 Hercules Incorporated Process for producing phenol from cumene
RU2108318C1 (ru) * 1994-03-01 1998-04-10 Закошанский Владимир Михайлович СПОСОБ ПОЛУЧЕНИЯ ФЕНОЛА, АЦЕТОНА И α МЕТИЛСТИРОЛА
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
RU2141938C1 (ru) 1996-12-15 1999-11-27 ООО "Илла Интернешнл", Лтд. Энергосберегающий и высокоселективный способ получения фенола и ацетона (процесс иф-96)
RU2142932C1 (ru) 1997-11-03 1999-12-20 Закошанский Владимир Михайлович Высокоселективный способ получения фенола и ацетона (процесс фан-98)
AU6135999A (en) * 1998-09-04 2000-03-27 Illa International L.L.C. High selective method of phenol and acetone production
DE19858770A1 (de) 1998-12-18 2000-06-21 Phenolchemie Gmbh & Co Kg Verfahren zur Herstellung von Phenol und Aceton durch säurekatalysierte Spaltung von Cumolhydroperoxid
US6201157B1 (en) 2000-01-10 2001-03-13 Sunoco, Inc. (R&M) Method for production of phenol and acetone by decomposition of cumene hydroperoxide
WO2004009522A1 (en) * 2002-07-19 2004-01-29 Sunoco, Inc. (R & M) Decomposition of cumene oxidation product
JP4078547B2 (ja) * 2003-06-16 2008-04-23 三菱化学株式会社 フェノール及びその製造方法
KR20070002039A (ko) 2004-03-31 2007-01-04 제너럴 일렉트릭 캄파니 페놀의 제조방법
RU2330011C1 (ru) 2007-03-01 2008-07-27 Общество с ограниченной ответственностью "Еврохим-СПб-Трейдинг" Способ получения фенола и ацетона

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013134049A1 (en) * 2012-03-09 2013-09-12 Honeywell International Inc. Method for producing alpha-methyl styrene from cumene
US8865957B2 (en) 2012-03-09 2014-10-21 Honeywell Intenational Inc. Method for producing alpha-methyl styrene from cumene
KR20140133844A (ko) * 2012-03-09 2014-11-20 허니웰 인터내셔널 인코포레이티드 큐멘으로부터 알파-메틸 스티렌의 생성 방법
CN104203880A (zh) * 2012-03-09 2014-12-10 霍尼韦尔国际公司 由枯烯制备α-甲基苯乙烯的方法
KR102039761B1 (ko) 2012-03-09 2019-11-01 어드밴식스 레진즈 앤드 케미컬즈 엘엘씨 큐멘으로부터 알파-메틸 스티렌의 생성 방법
EP3174630A4 (en) * 2014-07-29 2018-04-04 AdvanSix Resins & Chemicals LLC Reactor with baffle configuration
CN114436756A (zh) * 2020-10-16 2022-05-06 中国石油化工股份有限公司 一种制备异丙苯的方法、系统与应用
CN114981232A (zh) * 2020-12-21 2022-08-30 株式会社Lg化学 制备α-甲基苯乙烯的方法
EP4043420A4 (en) * 2020-12-21 2023-01-04 LG Chem, Ltd. PROCESS FOR PRODUCTION OF ALPHA-METHYLSTYRENE
US20230034930A1 (en) * 2020-12-21 2023-02-02 Lg Chem, Ltd. Method for preparing alpha-methylstyrene
US11858874B2 (en) * 2020-12-21 2024-01-02 Lg Chem, Ltd. Method for preparing alpha-methylstyrene

Also Published As

Publication number Publication date
US8247616B1 (en) 2012-08-21
WO2011156227A3 (en) 2012-04-05
RU2562236C2 (ru) 2015-09-10
EP2580181B1 (en) 2020-01-08
CA2802092A1 (en) 2011-12-15
US20120197045A1 (en) 2012-08-02
JP5793187B2 (ja) 2015-10-14
EP2580181A4 (en) 2015-11-04
KR20130122533A (ko) 2013-11-07
RU2012156422A (ru) 2014-07-20
KR101804596B1 (ko) 2017-12-04
CN103108855B (zh) 2015-07-22
JP2013531649A (ja) 2013-08-08
SG186237A1 (en) 2013-01-30
EP2580181A2 (en) 2013-04-17
BR112012031216A2 (pt) 2016-10-25
CN103108855A (zh) 2013-05-15
WO2011156227A2 (en) 2011-12-15

Similar Documents

Publication Publication Date Title
US8247616B1 (en) Method for the decomposition of cumene hydroperoxide
KR20010050752A (ko) 페놀, 아세톤 및 메틸 에틸 케톤의 제조방법
US7482493B2 (en) Method for the production of phenol and acetone
RU2334734C1 (ru) Способ получения фенола и ацетона
RU2404954C2 (ru) Способ получения фенола и ацетона
US8003827B2 (en) Method for producing phenol and acetone
US10745333B2 (en) Optimization of O-sulfonated phenol production for cumene hydroperoxide cleavage
US6875898B2 (en) Process for preparing phenols
EP4043420B1 (en) Method for producing alpha-methylstyrene
KR20010050696A (ko) 페놀의 제조방법
CN108602743B (zh) 纯化苯酚的方法
EP2193113B1 (en) Method for the production of phenol and acetone
EP1494984A1 (en) Process for preparing phenols
MXPA00006676A (en) Process for the preparation of phenol
EP3381885A1 (en) Method for purifying phenol

Legal Events

Date Code Title Description
AS Assignment

Owner name: HONEYWELL INTERNATIONAL INC., NEW JERSEY

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:SUNOCO, INC. (R&M);REEL/FRAME:026795/0045

Effective date: 20110722

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO PAY ISSUE FEE