EP1713753A1 - Entwässerung von kreislaufströmen bei der herstellung von bisphenol a - Google Patents
Entwässerung von kreislaufströmen bei der herstellung von bisphenol aInfo
- Publication number
- EP1713753A1 EP1713753A1 EP05701121A EP05701121A EP1713753A1 EP 1713753 A1 EP1713753 A1 EP 1713753A1 EP 05701121 A EP05701121 A EP 05701121A EP 05701121 A EP05701121 A EP 05701121A EP 1713753 A1 EP1713753 A1 EP 1713753A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- distillation
- acetone
- phenol
- bisphenol
- reaction
- 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.)
- Withdrawn
Links
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
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
-
- 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
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
-
- 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
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- 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
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
- C07C39/16—Bis-(hydroxyphenyl) alkanes; Tris-(hydroxyphenyl)alkanes
Definitions
- the present application relates to a process for the preparation of bisphenol A, in which the reaction mixture obtained by acid-catalyzed conversion of phenol and acetone is freed from the water formed during the reaction by distillation, a large part of the unreacted acetone remaining in the reaction mixture.
- Bisphenols as condensation products of phenols and carbonyl compounds are starting materials or intermediates for the production of a large number of commercial products. Of particular technical importance is the condensation product from the reaction between phenol and acetone, 2,2-bis (4-hydroxyphenyl) propane (bisphenol A, BPA). BPA serves as a raw material for. Production of various types of polymeric materials such as polyarylates, polyether imides, polysulfones and modified phenol-formaldehyde resins. Preferred areas of application are in the production of epoxy resins and polycarbonates.
- cocatalyst usually thiols that have at least one SH function.
- the cocatalyst can either be dissolved homogeneously in the reaction solution or, in the case of the acidic ion exchangers, can be fixed on the catalyst itself.
- Homogeneous cocatalysts are, for example, mercapto propionic acid, hydrogen sulfide, alkyl sulfides such as ethyl sulfide and similar compounds.
- Fixed cocatalysts are aminoalkylthiols and pyridylalkylthiols which are ionically bound to the catalyst, where the SH function can be protected and is only released to the catalyst during or after fixation.
- the cocatalyst can be covalently bound to the catalyst as alkyl or aryl thiol.
- reaction is usually carried out in such a way that 100% conversion of the acetone is not achieved and 0.1-0.6% by weight in the reactor outlet. Acetone are included.
- a processing and purification method of BPA is carried out by separating BPA from the reaction mixture in the form of an approximately equimolar crystalline. Adduct with phenol by cooling the reaction mixture with crystallization of the BPA-phenol adduct in a suspension crystallization. The BPA-phenol adduct crystals are then separated from the liquid phase by a suitable apparatus for solid-liquid separation, such as rotary filters or centrifuges, and sent for further purification.
- Adduct crystals obtained in this way typically have a purity of> 99% by weight of BPA, based on the sum of BPA and the secondary components, with a phenol content of approximately 40% by weight.
- suitable solutions which typically contain one or more components from the group consisting of acetone, water, phenol, BPA and secondary components, the adduct crystals can be freed from impurities adhering to the surface.
- the liquid stream (mother liquor) obtained in the solid-liquid separation contains phenol, BPA, water formed in the reaction, unreacted acetone and is enriched in the secondary components typically obtained in the production of BPA.
- This mother liquor stream is usually returned to the reaction unit.
- water previously formed is removed by distillation, wherein any acetone still present is also removed from the mother liquor.
- the dewatered reaction stream thus obtained is supplemented by phenol and acetone and returned to the reaction unit.
- water and acetone can also be removed by distillation before the suspension crystallization of the BPA-phenol adduct is carried out.
- the BPA-phenol adduct crystals obtained after the above-described suspension crystallization of the reaction solution and solid-liquid separation are passed on to further purification steps, with the separation of phenol and possibly a reduction in the concentration of secondary components being achieved.
- the BPA-phenol adduct crystals can thus be recrystallized from phenol, organic solvents, water or mixtures of the solvents mentioned, which may also contain BPA and / or its isomers, by means of a suspension crystallization.
- the phenol present in the adduct crystals can also be removed in whole or in part by the choice of suitable solvents. Any phenol remaining in the BPA after recrystallization is then completely separated off by suitable distillative, desorptive or extractive methods.
- the phenol can also be removed from the BPA-phenol adduct crystals by means of a melting process. In these processes, however, the BPA is subject to thermal loads, which leads to undesirable splitting of BPA.
- a bisphenol A melt is obtained which can be used without prior solidification for the production of polycarbonate by the transesterification process (melt polycarbonate).
- the bisphenol A melt can, however, also be solidified by known processes, such as, for example, by the prilling process or by desquamation, for sale or further use.
- the melt can be dissolved in sodium hydroxide solution and used in the polycarbonate process using the phase interface process.
- Ge sacrificeen- if the phenol-free bisphenol A can be subjected to a purification step such as melt crystallization, distillation and / or primary crystallization from phenol, water or an organic solvent such as toluene or mixtures of these substances before further processing.
- the mother liquor must be dewatered before it is returned to the reaction, since, due to the thermodynamic equilibrium, the water of reaction would strongly suppress the reaction of phenol and acetone to bisphenol A and thus reduce the reaction conversion.
- the unreacted residual acetone should remain in the reaction solution, since it would otherwise have to be laboriously isolated from side streams and returned to the reaction in order to keep raw material losses low for economic reasons
- the object of the present invention was therefore to provide a process for the preparation of bisphenol A. With which the water of reaction can be removed from the reaction solution or from the mother liquor which comes from the crystallization and filtration, the unreacted Most of the residual acetone remains in the reaction solution.
- the invention relates to a process for the preparation of bisphenol A, in which
- step b) before or after the distillation in step b), a bisphenol A-phenol adduct is separated off from the reaction mixture by crystallization and filtration.
- the invention is based on the knowledge that when the reaction mixture is worked up by distillation in a vacuum distillation for water removal, the water can be separated off almost quantitatively, ie to more than 95%. At the same time, however, more than 80% of the unconverted acetone introduced into the distillation preferably remains in the bottom product in this vacuum distillation.
- the bottom product also preferably contains between 0.01 and 0.2% by weight of water (based on the bottom product).
- the distillation column used with a bottom temperature of 100 to 150 ° C, preferably 110 to 140 ° C, particularly preferably 125 to 135 ° C and a top temperature of 20 to 80 ° C, preferably 30 to 70 ° C, particularly preferably 50 to 60 ° C operated.
- the vacuum in the top of the column is 50 to 300 mbar, preferably 80 to 200 mbar, particularly preferably 100 to 150 mbar.
- the bottom vacuum is from 100 to 300mbar 5 preferably from 120 to 250mbar and more preferably 150 to 200 mbar.
- Distillation devices which are known to the person skilled in the art and which contain internals, for example packing elements and / or packings and / or bottoms, can be used as the separation process for solving the problem.
- the bottom product obtained in the distillation is, if appropriate after separating off the bisphenol A-phenol adduct crystals by means of a suspension crystallization, for reuse in the reaction after addition of the used components phenol and acetone and optionally cocatalyst.
- the phenol used can be supplemented in whole or in part before the distillation.
- Another advantage of the process according to the invention is that degradation compounds of the sulfur-containing cocatalyst, such as mercaptopropionic acid and of the sulfonic acid ion exchanger, are likewise removed overhead with the water of reaction and thus when the bottom product is returned to the reaction, not in the reaction and, above all, in the later removal of the Disrupt bisphenol A.
- impurities from the raw materials used such as methanol, and by-products resulting from the production of bisphenol A, such as anisole from methanol and phenol, and the compounds resulting from the self-condensation of acetone, such as, for example, mesitylene, mesityl oxide and diacetone alcohol, can be at least partially, but preferably at least 5 . 0%, cut off overhead.
- mercaptopropionic acid is used as the cocatalyst, the cocatalyst remains in the bottom product. Only the decomposed portion and the portion lost due to the withdrawal from the circuit have to be added in order to run the reaction with a constant cocatalyst content. ' ⁇ ⁇
- the bisphenol A produced by the process according to the invention is preferably reacted with phosgene according to the interfacial process or with diaryl carbonates, preferably diphenyl carbonate, according to the melt process to polycarbonate.
- phosgene phosgene according to the interfacial process
- diaryl carbonates preferably diphenyl carbonate
- the vacuum is 163 mbar in the sump and 129 mbar in the head.
- Over 95% of the water of reaction introduced into the column is condensed at the top, the rest remaining in the bottom product.
- the top product contains 5% by weight of phenol and 5% by weight of acetone, based on the top product.
- anisole and methanol as well as acetone's own condensation products such as.
- the BPA originating from this process is suitable for the production of polycarbonate using both the phase interface and the transesterification (melt) process.
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102004005726A DE102004005726A1 (de) | 2004-02-05 | 2004-02-05 | Entwässerung von Kreislaufströmen bei der Herstellung von Bisphenol A |
PCT/EP2005/000616 WO2005075397A1 (de) | 2004-02-05 | 2005-01-22 | Entwässerung von kreislaufströmen bei der herstellung von bisphenol a |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1713753A1 true EP1713753A1 (de) | 2006-10-25 |
Family
ID=34801629
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP05701121A Withdrawn EP1713753A1 (de) | 2004-02-05 | 2005-01-22 | Entwässerung von kreislaufströmen bei der herstellung von bisphenol a |
Country Status (9)
Country | Link |
---|---|
US (1) | US7078573B2 (de) |
EP (1) | EP1713753A1 (de) |
JP (1) | JP2007520503A (de) |
KR (1) | KR20060132895A (de) |
CN (1) | CN1914142B (de) |
DE (1) | DE102004005726A1 (de) |
RU (1) | RU2392261C2 (de) |
TW (1) | TW200604157A (de) |
WO (1) | WO2005075397A1 (de) |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9290618B2 (en) | 2011-08-05 | 2016-03-22 | Sabic Global Technologies B.V. | Polycarbonate compositions having enhanced optical properties, methods of making and articles comprising the polycarbonate compositions |
US8962117B2 (en) | 2011-10-27 | 2015-02-24 | Sabic Global Technologies B.V. | Process for producing bisphenol A with reduced sulfur content, polycarbonate made from the bisphenol A, and containers formed from the polycarbonate |
CN104205376B (zh) | 2012-02-03 | 2018-04-27 | 沙特基础全球技术有限公司 | 发光二极管器件及用于生产其的包括转换材料化学的方法 |
CN105206732B (zh) | 2012-02-29 | 2018-11-09 | 沙特基础全球技术有限公司 | 塑料模制器件和发光器件 |
EP2819981B1 (de) | 2012-02-29 | 2016-12-21 | SABIC Global Technologies B.V. | Polycarbonat aus bisphenol a mit niedrigem schwefelgehalt und mit umwandlungsmaterialchemie sowie daraus hergestellte artikel |
US9346949B2 (en) | 2013-02-12 | 2016-05-24 | Sabic Global Technologies B.V. | High reflectance polycarbonate |
WO2014066784A1 (en) | 2012-10-25 | 2014-05-01 | Sabic Innovative Plastics Ip B.V. | Light emitting diode devices, method of manufacture, uses thereof |
WO2014186548A1 (en) | 2013-05-16 | 2014-11-20 | Sabic Innovative Plastics Ip B.V. | Branched polycarbonate compositions having conversion material chemistry and articles thereof |
CN105408408B (zh) | 2013-05-29 | 2018-05-04 | 沙特基础全球技术有限公司 | 颜色稳定的热塑性组合物 |
US9772086B2 (en) | 2013-05-29 | 2017-09-26 | Sabic Innovative Plastics Ip B.V. | Illuminating devices with color stable thermoplastic light transmitting articles |
DE102016116078B3 (de) | 2016-08-29 | 2018-01-04 | Epc Engineering Consulting Gmbh | Verfahren zur Herstellung eines Polycarbonats unter Einsatz einer Strippvorrichtung |
KR20220050899A (ko) | 2019-08-27 | 2022-04-25 | 코베스트로 인텔렉쳐 프로퍼티 게엠베하 운트 콤파니 카게 | 히드록시아세톤의 존재 하에 비스페놀 a (bpa)를 제조하는 방법 |
CN116867760A (zh) | 2021-02-23 | 2023-10-10 | 科思创德国股份有限公司 | 在异丙苯存在下制备双酚a(bpa)的方法 |
CN116867761A (zh) | 2021-02-23 | 2023-10-10 | 科思创德国股份有限公司 | 在2-甲基苯并呋喃存在下制备双酚a(bpa)的方法 |
WO2022179901A1 (en) | 2021-02-23 | 2022-09-01 | Covestro Deutschland Ag | Process for preparing bisphenol a (bpa) in the presence of at least two impurities |
CN116888092A (zh) | 2021-02-23 | 2023-10-13 | 科思创德国股份有限公司 | 在苯乙酮存在下制备双酚a(bpa)的方法 |
KR20230149814A (ko) | 2021-02-23 | 2023-10-27 | 코베스트로 도이칠란트 아게 | 알파-메틸스티렌의 존재 하에 비스페놀 a (bpa)를 제조하는방법 |
JP2024508774A (ja) | 2021-02-23 | 2024-02-28 | コベストロ、ドイチュラント、アクチエンゲゼルシャフト | ベンゼンの存在下でビスフェノールa(bpa)を作製するプロセス |
WO2023280514A1 (en) | 2021-07-05 | 2023-01-12 | Sabic Global Technologies B.V. | Method for the manufacture of bisphenol a |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01211544A (ja) * | 1988-02-19 | 1989-08-24 | Mitsui Toatsu Chem Inc | ビスフェノールaの製造方法 |
US4994594A (en) * | 1988-02-29 | 1991-02-19 | General Electric Company | Oligomeric carbonate chainstoppers |
EP0720976B2 (de) * | 1994-12-09 | 2005-05-18 | The Dow Chemical Company | Verfahren zur Herstellung eines Addukts aus einem Bisphenol mit einer Phenol-Verbindung |
DE19529855A1 (de) * | 1995-08-14 | 1997-02-20 | Bayer Ag | Verfahren zur Reinigung von Bisphenol |
JP4093655B2 (ja) * | 1998-10-22 | 2008-06-04 | 出光興産株式会社 | ビスフェノールaの製造法 |
DE19954311A1 (de) * | 1999-11-11 | 2001-05-17 | Bayer Ag | Bisphenol-Herstellung |
DE19954786A1 (de) * | 1999-11-15 | 2001-05-17 | Bayer Ag | Schmelzkristallisation |
JP2001199919A (ja) | 2000-01-18 | 2001-07-24 | Idemitsu Petrochem Co Ltd | ビスフェノールaの製造方法 |
JP4080710B2 (ja) * | 2000-09-26 | 2008-04-23 | 三菱化学株式会社 | 芳香族ポリカーボネートの製造方法 |
JP2003055286A (ja) * | 2001-08-06 | 2003-02-26 | Idemitsu Petrochem Co Ltd | ビスフェノールaの製造方法 |
-
2004
- 2004-02-05 DE DE102004005726A patent/DE102004005726A1/de not_active Withdrawn
-
2005
- 2005-01-22 EP EP05701121A patent/EP1713753A1/de not_active Withdrawn
- 2005-01-22 KR KR1020067015877A patent/KR20060132895A/ko not_active Application Discontinuation
- 2005-01-22 RU RU2006131516/04A patent/RU2392261C2/ru not_active IP Right Cessation
- 2005-01-22 WO PCT/EP2005/000616 patent/WO2005075397A1/de active Application Filing
- 2005-01-22 JP JP2006551755A patent/JP2007520503A/ja active Pending
- 2005-01-22 CN CN2005800035885A patent/CN1914142B/zh not_active Expired - Fee Related
- 2005-01-26 US US11/043,275 patent/US7078573B2/en not_active Expired - Fee Related
- 2005-02-03 TW TW094103288A patent/TW200604157A/zh unknown
Non-Patent Citations (1)
Title |
---|
See references of WO2005075397A1 * |
Also Published As
Publication number | Publication date |
---|---|
DE102004005726A1 (de) | 2005-08-25 |
RU2392261C2 (ru) | 2010-06-20 |
CN1914142A (zh) | 2007-02-14 |
CN1914142B (zh) | 2010-05-26 |
WO2005075397A1 (de) | 2005-08-18 |
RU2006131516A (ru) | 2008-03-10 |
US20050177007A1 (en) | 2005-08-11 |
TW200604157A (en) | 2006-02-01 |
KR20060132895A (ko) | 2006-12-22 |
US7078573B2 (en) | 2006-07-18 |
JP2007520503A (ja) | 2007-07-26 |
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Legal Events
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PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
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Effective date: 20060905 |
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RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: NEUMANN, RAINER Inventor name: BLASCHKE, ULRICH Inventor name: WESTERNACHER, STEFAN |
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DAX | Request for extension of the european patent (deleted) | ||
RBV | Designated contracting states (corrected) |
Designated state(s): BE ES NL PT |
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17Q | First examination report despatched |
Effective date: 20100630 |
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Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
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18D | Application deemed to be withdrawn |
Effective date: 20110802 |