JP2006526625A - クメンヒドロペルオキシドからビスフェノールaを製造するための統合プロセス - Google Patents
クメンヒドロペルオキシドからビスフェノールaを製造するための統合プロセス Download PDFInfo
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- JP2006526625A JP2006526625A JP2006509906A JP2006509906A JP2006526625A JP 2006526625 A JP2006526625 A JP 2006526625A JP 2006509906 A JP2006509906 A JP 2006509906A JP 2006509906 A JP2006509906 A JP 2006509906A JP 2006526625 A JP2006526625 A JP 2006526625A
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- JP
- Japan
- Prior art keywords
- acetone
- pat
- phenol
- catalyst
- bpa
- 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.)
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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
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
-
- 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
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
-
- 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
- C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
- C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
-
- 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
- Y02P20/10—Process efficiency
-
- 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)
- Catalysts (AREA)
Abstract
Description
(a)酸処理クレー触媒の存在下でCHPを開裂してフェノール及びアセトンを生成させる段階と、
(b)好ましくは中間精製なしに、段階(a)で生成したフェノール及びアセトンを陽イオン交換樹脂触媒の存在下で反応させてBPAを製造する段階と
を含んでなる方法によって、CHPからBPAを製造する。
図1は、本発明によるBPA製造用設備の第一の実施形態の略図を示す。
55℃で、16.33mlのアセトンと1.9gのFiltrol−24(Engelhard社)酸処理モンモリロナイトクレーとの混合物に25.3gの工業用80%CHP(81%CHP、8.7%DMBA、1.36%α−メチルスチレン、0.7%アセトフェノン及び7.2%クメンからなるものとして分析されるもの)をゆっくりと添加した。添加は、反応温度を65℃以下に維持するように制御した。CHP添加の完了後、混合物を55℃でさらに30分間攪拌し、ガスクロマトグラフィーを用いて完結状態を分析した。CHPを基準にして95%の収率でフェノールを得た。
酸性クレー触媒の代わりに2gのXE−760(Rohm and Haas社)をCHP開裂触媒として使用し、第二のBPA合成段階では40%PEM添加XE−760の代わりに3gmのXE−760を使用した点を除き、実施例1の実験を繰り返した。得られたp,p−BPAのモル収率は(CHPを基準にして)50.9%であり、そのp−p/o−p比は88.97%であった。
酸性クレー触媒の代わりに硫酸(300ppm)をCHP開裂触媒として使用した点を除き、実施例1の実験を繰り返した。同等な選択率が得られたが、p,p−BPAの収率はCHPを基準にして18.45%にすぎなかった。
同じ作業条件下で実施例1の方法を繰り返したが、今回はCHP開裂のための触媒として2.0gのAmberlyst XE−760(Rohm and Haas社)を使用した。フェノールの収率は95%であった一方、得られたp,p−BPAのモル収率は(CHPを基準にして)85.4%であり、BPAのp−p/o−p比は97.3%であった。
Claims (10)
- ビスフェノールAの製造方法であって、
(a)酸性クレー触媒の存在下でクメンヒドロペルオキシドを開裂して、クメンヒドロペルオキシドをフェノールとアセトンを含む開裂体に実質的に転化させる段階と、
(b)陽イオン交換樹脂及びメルカプタン又はメルカプトアルカン酸助触媒を含む陽イオン交換樹脂触媒の存在下で開裂体を反応させて、開裂体中のフェノール及びアセトンをビスフェノールAに実質的に転化させる段階と
を含んでなる方法。 - 段階(a)で生成した開裂体を、中間精製なしに段階(b)で反応させる、請求項1記載の方法。
- クメンヒドロペルオキシドを開裂する段階が55〜65℃の温度で実施される、請求項1又は請求項2記載の方法。
- さらに、段階(a)で生成した開裂体にフェノールを添加するか又は開裂体からアセトンを除去することで、1:20〜1:10のアセトン:フェノールモル比を得る段階を含む、請求項1乃至請求項3のいずれか1項記載の方法。
- 得られるアセトン:フェノールモル比が1:13である、請求項4記載の方法。
- 段階(b)が40〜100℃の温度で実施される、請求項1乃至請求項5のいずれか1項記載の方法。
- 陽イオン交換樹脂触媒が助触媒としてピリジルエチルメルカプタンを含む、請求項1乃至請求項6のいずれか1項記載の方法。
- ピリジルエチルメルカプタンが20〜70重量%の量で陽イオン交換樹脂触媒に添加される、請求項7記載の方法。
- ピリジルエチルメルカプタンが40重量%の量で陽イオン交換樹脂触媒に添加される、請求項8記載の方法。
- 触媒が酸処理したモンモリロナイトクレーである、請求項1乃至請求項9のいずれか1項記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/250,114 US7491855B2 (en) | 2003-06-04 | 2003-06-04 | Integrated process for the production of bisphenol A from cumene hydroperoxide |
US10/250,114 | 2003-06-04 | ||
PCT/US2004/011144 WO2004108640A2 (en) | 2003-06-04 | 2004-04-12 | Integrated process for the production of bisphenol a from cumene hydroperoxide |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2006526625A true JP2006526625A (ja) | 2006-11-24 |
JP4790601B2 JP4790601B2 (ja) | 2011-10-12 |
Family
ID=33489123
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006509906A Expired - Fee Related JP4790601B2 (ja) | 2003-06-04 | 2004-04-12 | クメンヒドロペルオキシドからビスフェノールaを製造するための統合プロセス |
Country Status (10)
Country | Link |
---|---|
US (1) | US7491855B2 (ja) |
EP (1) | EP1636157B1 (ja) |
JP (1) | JP4790601B2 (ja) |
KR (1) | KR20060006847A (ja) |
CN (1) | CN100369878C (ja) |
AT (1) | ATE455747T1 (ja) |
DE (1) | DE602004025238D1 (ja) |
RU (1) | RU2339609C2 (ja) |
TW (1) | TWI339653B (ja) |
WO (1) | WO2004108640A2 (ja) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7417003B2 (en) * | 2006-12-29 | 2008-08-26 | Uop Llc | Solid acid catalyst and process for decomposition of cumene hydroperoxide |
RU2566504C1 (ru) * | 2014-08-08 | 2015-10-27 | Общество с ограниченной ответственностью "Научно-производственное объединение ЕВРОХИМ" | Способ окисления алкилароматических углеводородов и реактор для его осуществления |
WO2017044229A1 (en) * | 2015-09-11 | 2017-03-16 | Sabic Global Technologies B.V. | A method of recovering phenol from a bpa production plant and the plant for recovering the same |
EP3383833B1 (en) | 2015-12-03 | 2020-11-11 | SABIC Global Technologies B.V. | Method of recovering phenol from a bpa production facility and the facility for recovering the same |
EP3210963B1 (en) * | 2016-02-25 | 2019-03-27 | SABIC Global Technologies B.V. | Method of recovering acetone and a plant for recovering the same |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02169529A (ja) * | 1988-10-24 | 1990-06-29 | Texaco Dev Corp | クメンヒドロペルオキシドからフェノール及びアセトンを製造する方法 |
JP2001503377A (ja) * | 1995-12-19 | 2001-03-13 | シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ | ビスフェノールの改良された製造方法 |
JP2002069023A (ja) * | 2000-08-30 | 2002-03-08 | Mitsubishi Chemicals Corp | ビスフェノールの製造方法 |
JP2002316962A (ja) * | 2001-04-17 | 2002-10-31 | Idemitsu Petrochem Co Ltd | ビスフェノールaの製造方法 |
Family Cites Families (28)
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US2923744A (en) | 1960-02-02 | Preparation of bis-z | ||
US3172916A (en) | 1965-03-09 | Bisphenol axpreparation u using ion ex- change resin containing mercapto and sulfonic acid groups | ||
US2468982A (en) | 1946-10-19 | 1949-05-03 | Goodrich Co B F | Preparation of bis-phenols |
GB766549A (en) | 1952-10-31 | 1957-01-23 | Bergwerksgesellschaft Hibernia | Improvements in or relating to hydroxy aryl substituted propane compounds |
US3394089A (en) | 1964-12-02 | 1968-07-23 | Dow Chemical Co | Ion exchange catalyst for the preparation of bisphenols |
DE2931036A1 (de) | 1979-07-31 | 1981-02-26 | Bayer Ag | Katalysator fuer die herstellung von bisphenolen |
DE2935316A1 (de) | 1979-08-31 | 1981-03-26 | Bayer Ag, 51373 Leverkusen | Verfahren zur herstellung reiner 4,4'-dihydroxydiphenylalkane bzw. -cycloalkane |
US4294995A (en) | 1979-12-13 | 1981-10-13 | General Electric Company | Method and catalyst for making bisphenol |
US4423252A (en) | 1980-08-07 | 1983-12-27 | Mitsubishi Chemical Industries Limited | Process for preparing bisphenols |
US4396728A (en) | 1980-09-30 | 1983-08-02 | General Electric Company | Method and catalyst for making bisphenol |
US4455409A (en) | 1982-12-02 | 1984-06-19 | General Electric Company | Method for making bisphenol catalysts |
US4490566A (en) | 1983-05-06 | 1984-12-25 | Mobil Oil Corporation | Production of phenol |
US4490565A (en) | 1983-05-06 | 1984-12-25 | Mobil Oil Corporation | Production of phenol |
US5212206A (en) | 1986-06-10 | 1993-05-18 | Bayer Aktiengesellschaft | Ion exchange modified with mercapto amines |
DE3736814A1 (de) | 1987-10-30 | 1989-05-11 | Roehm Gmbh | Verfahren zur herstellung von bisphenolaromaten |
DE3835204A1 (de) | 1988-10-15 | 1990-04-19 | Bayer Ag | Verfahren zur herstellung von dihydroxidiarylalkanen |
US4870217A (en) | 1988-10-24 | 1989-09-26 | Texaco Chemical Company | Method for production of phenol/acetone from cumene hydroperoxide |
US4898987A (en) | 1989-03-17 | 1990-02-06 | Texaco Chemical Company | Method for production of phenol/acetone from cumene hydroperoxide |
US4898995A (en) | 1988-10-24 | 1990-02-06 | Texaco Chemical Company | Method for production of phenol/acetone from cumene hydroperoxide |
US5113034A (en) | 1991-08-05 | 1992-05-12 | Exxon Research And Engineering Company | Dimerization catalyst and process therefor |
DE4227520A1 (de) | 1992-08-20 | 1994-02-24 | Bayer Ag | Verfahren zur Herstellung von Bisphenolen |
US5315042A (en) | 1993-03-22 | 1994-05-24 | General Electric Company | Use of partial acetone conversion for capacity increase and quality/yield improvement in the bisphenol-A reaction |
US5824622A (en) | 1994-01-12 | 1998-10-20 | E. I. Du Pont De Nemours And Company | Porous microcomposite of perfluorinated ion-exchange polymer and metal oxide, a network of silica, or a network of metal oxide and silica derived via a sol-gel process |
US6013845A (en) * | 1996-03-21 | 2000-01-11 | Shell Oil Company | Fixed bed reactor packing |
US6169215B1 (en) | 1999-03-25 | 2001-01-02 | Mobil Oil Corporation | Production of phenol |
US6169216B1 (en) | 1999-04-22 | 2001-01-02 | Mobil Oil Corporation | Production of phenol |
US6297406B1 (en) | 1999-08-03 | 2001-10-02 | Mobil Oil Corporation | Production of phenol |
US6534686B1 (en) | 2001-09-18 | 2003-03-18 | General Electric Company | Method for producing bisphenol catalysts and bisphenols |
-
2003
- 2003-06-04 US US10/250,114 patent/US7491855B2/en not_active Expired - Fee Related
-
2004
- 2004-04-12 RU RU2005137703/04A patent/RU2339609C2/ru not_active IP Right Cessation
- 2004-04-12 DE DE602004025238T patent/DE602004025238D1/de not_active Expired - Lifetime
- 2004-04-12 AT AT04749983T patent/ATE455747T1/de not_active IP Right Cessation
- 2004-04-12 JP JP2006509906A patent/JP4790601B2/ja not_active Expired - Fee Related
- 2004-04-12 WO PCT/US2004/011144 patent/WO2004108640A2/en active Application Filing
- 2004-04-12 CN CNB2004800155581A patent/CN100369878C/zh not_active Expired - Fee Related
- 2004-04-12 KR KR1020057023061A patent/KR20060006847A/ko not_active Application Discontinuation
- 2004-04-12 EP EP04749983A patent/EP1636157B1/en not_active Expired - Lifetime
- 2004-05-19 TW TW093114115A patent/TWI339653B/zh active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02169529A (ja) * | 1988-10-24 | 1990-06-29 | Texaco Dev Corp | クメンヒドロペルオキシドからフェノール及びアセトンを製造する方法 |
JP2001503377A (ja) * | 1995-12-19 | 2001-03-13 | シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ | ビスフェノールの改良された製造方法 |
JP2002069023A (ja) * | 2000-08-30 | 2002-03-08 | Mitsubishi Chemicals Corp | ビスフェノールの製造方法 |
JP2002316962A (ja) * | 2001-04-17 | 2002-10-31 | Idemitsu Petrochem Co Ltd | ビスフェノールaの製造方法 |
Also Published As
Publication number | Publication date |
---|---|
CN100369878C (zh) | 2008-02-20 |
CN1798720A (zh) | 2006-07-05 |
WO2004108640A2 (en) | 2004-12-16 |
TWI339653B (en) | 2011-04-01 |
WO2004108640A3 (en) | 2005-02-24 |
ATE455747T1 (de) | 2010-02-15 |
RU2339609C2 (ru) | 2008-11-27 |
TW200505833A (en) | 2005-02-16 |
RU2005137703A (ru) | 2007-06-10 |
KR20060006847A (ko) | 2006-01-19 |
EP1636157B1 (en) | 2010-01-20 |
EP1636157A2 (en) | 2006-03-22 |
US20040249224A1 (en) | 2004-12-09 |
JP4790601B2 (ja) | 2011-10-12 |
DE602004025238D1 (de) | 2010-03-11 |
US7491855B2 (en) | 2009-02-17 |
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