TWI250976B - Combination ion exchange resin bed for the synthesis of bisphenol A - Google Patents
Combination ion exchange resin bed for the synthesis of bisphenol A Download PDFInfo
- Publication number
- TWI250976B TWI250976B TW089102540A TW89102540A TWI250976B TW I250976 B TWI250976 B TW I250976B TW 089102540 A TW089102540 A TW 089102540A TW 89102540 A TW89102540 A TW 89102540A TW I250976 B TWI250976 B TW I250976B
- Authority
- TW
- Taiwan
- Prior art keywords
- resin
- bed
- upper layer
- ion exchange
- crosslinking
- Prior art date
Links
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 title claims abstract description 54
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 239000003456 ion exchange resin Substances 0.000 title claims abstract description 34
- 229920003303 ion-exchange polymer Polymers 0.000 title claims abstract description 34
- 230000015572 biosynthetic process Effects 0.000 title description 8
- 238000003786 synthesis reaction Methods 0.000 title description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 82
- 239000011347 resin Substances 0.000 claims abstract description 68
- 229920005989 resin Polymers 0.000 claims abstract description 68
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 42
- 238000004132 cross linking Methods 0.000 claims abstract description 37
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 19
- 125000000542 sulfonic acid group Chemical group 0.000 claims abstract description 14
- 238000005342 ion exchange Methods 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 6
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 230000002079 cooperative effect Effects 0.000 claims description 4
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 claims 1
- 239000012991 xanthate Substances 0.000 claims 1
- 230000009849 deactivation Effects 0.000 abstract description 6
- 230000003197 catalytic effect Effects 0.000 abstract description 5
- 230000008569 process Effects 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 12
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 7
- 239000011324 bead Substances 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 239000012508 resin bead Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 208000005156 Dehydration Diseases 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- -1 polyphenylene Ethylene Polymers 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000011269 tar Substances 0.000 description 2
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- XDTRNDKYILNOAP-UHFFFAOYSA-N phenol;propan-2-one Chemical compound CC(C)=O.OC1=CC=CC=C1 XDTRNDKYILNOAP-UHFFFAOYSA-N 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
- B01J8/04—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds the fluid passing successively through two or more beds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
- B01J31/10—Ion-exchange resins sulfonated
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
- B01J2231/341—1,2-additions, e.g. aldol or Knoevenagel condensations
- B01J2231/347—1,2-additions, e.g. aldol or Knoevenagel condensations via cationic intermediates, e.g. bisphenol A type processes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25823599A | 1999-02-26 | 1999-02-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI250976B true TWI250976B (en) | 2006-03-11 |
Family
ID=22979669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW089102540A TWI250976B (en) | 1999-02-26 | 2000-02-15 | Combination ion exchange resin bed for the synthesis of bisphenol A |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6486222B2 (https=) |
| EP (1) | EP1163198B1 (https=) |
| JP (1) | JP2002537116A (https=) |
| KR (1) | KR100693659B1 (https=) |
| CN (1) | CN1173910C (https=) |
| AT (1) | ATE253029T1 (https=) |
| BR (1) | BR0008481A (https=) |
| DE (1) | DE60006220T2 (https=) |
| RU (1) | RU2001126118A (https=) |
| TW (1) | TWI250976B (https=) |
| WO (1) | WO2000050372A1 (https=) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4995372B2 (ja) * | 2001-01-19 | 2012-08-08 | 出光興産株式会社 | ビスフェノールａの製造方法 |
| US6703530B2 (en) * | 2002-02-28 | 2004-03-09 | General Electric Company | Chemical reactor system and process |
| US7141640B2 (en) | 2002-10-08 | 2006-11-28 | General Electric Company | Process for producing dihydroxy compounds using upflow reactor system |
| US7112702B2 (en) | 2002-12-12 | 2006-09-26 | General Electric Company | Process for the synthesis of bisphenol |
| US7132575B2 (en) | 2003-07-01 | 2006-11-07 | General Electric Company | Process for the synthesis of bisphenol |
| US7015365B2 (en) * | 2003-12-19 | 2006-03-21 | General Electric Company | Methods for preparing cycloalkylidene bisphenols |
| DE102004005724A1 (de) * | 2004-02-05 | 2005-08-25 | Bayer Materialscience Ag | Herstellung von Bisphenol A mit verringerter Isomerenbildung |
| DE102004005722A1 (de) * | 2004-02-05 | 2005-08-25 | Bayer Materialscience Ag | Verfahren zur Herstellung von Bisphenolen mit optimaler Befüllung des Reaktors mit Katalysator |
| US8735634B2 (en) | 2011-05-02 | 2014-05-27 | Sabic Innovative Plastics Ip B.V. | Promoter catalyst system with solvent purification |
| CN102250065B (zh) * | 2011-05-20 | 2015-05-13 | 浙江海正药业股份有限公司 | 取代的三嗪苯脲衍生物及其用途 |
| 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 |
| 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 |
| WO2013130610A1 (en) | 2012-02-29 | 2013-09-06 | Sabic Innovative Plastics Ip B.V. | Polycarbonate compositions containing conversions material chemistry and having enhanced optical properties, methods of making and articles comprising the same |
| CN104144902A (zh) | 2012-02-29 | 2014-11-12 | 沙特基础创新塑料Ip私人有限责任公司 | 用于生产低硫双酚a的方法、用于生产聚碳酸酯的方法以及由聚碳酸酯制作的制品 |
| US9346949B2 (en) | 2013-02-12 | 2016-05-24 | Sabic Global Technologies B.V. | High reflectance polycarbonate |
| EP2912107B1 (en) | 2012-10-25 | 2018-03-28 | SABIC Global Technologies 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 |
| CN105492519B (zh) | 2013-05-29 | 2018-03-09 | 沙特基础全球技术有限公司 | 具有颜色稳定的热塑性光传输制品的照明设备 |
| CN103896742B (zh) * | 2014-01-21 | 2015-12-02 | 湘潭大学 | 一种阳离子交换树脂固载离子液体催化合成双酚f的方法 |
| WO2017221205A1 (en) | 2016-06-24 | 2017-12-28 | Sabic Global Technologies B.V. | Cross-linked polystyrene catalyst, method of making, and uses thereof |
| CN108479861A (zh) * | 2018-05-08 | 2018-09-04 | 中国船舶重工集团公司第七0七研究所九江分部 | 一种耐振离子交换树脂滤芯 |
| WO2023110712A1 (en) | 2021-12-17 | 2023-06-22 | Sabic Global Technologies B.V. | Method for manufacturing a core-shell catalyst and method and upflow reactor for carrying out a catalysed reaction between phenol and acetone to form bisphenol a |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3394089A (en) | 1964-12-02 | 1968-07-23 | Dow Chemical Co | Ion exchange catalyst for the preparation of bisphenols |
| US4051079A (en) | 1976-06-22 | 1977-09-27 | Union Carbide Corporation | Regeneration of acidic cation exchange resin using acidified phenol-water mixture |
| US4400555A (en) | 1981-10-06 | 1983-08-23 | General Electric Company | Ion exchange catalyzed bisphenol synethesis |
| US4391997A (en) | 1981-10-23 | 1983-07-05 | General Electric Company | Ion exchange catalyzed bisphenol process |
| US4590303A (en) | 1985-06-03 | 1986-05-20 | General Electric Company | Method for making bisphenol |
| US5212206A (en) | 1986-06-10 | 1993-05-18 | Bayer Aktiengesellschaft | Ion exchange modified with mercapto amines |
| US5284981A (en) | 1986-06-10 | 1994-02-08 | Bayer Aktiengesellschaft | Ion exchangers modified with mercapto amines |
| DE3619450A1 (de) | 1986-06-10 | 1987-12-17 | Bayer Ag | Mit mercaptoaminen modifizierte ionenaustauscher |
| JPH0597741A (ja) * | 1991-10-11 | 1993-04-20 | Chiyoda Corp | ビスフエノール化合物の製造方法 |
| DE4312039A1 (de) | 1993-04-13 | 1994-10-20 | Bayer Ag | Optimierte Ionenaustauscherschüttungen für die Bis-phenol-A Synthese |
| DE4312038A1 (de) | 1993-04-13 | 1994-10-20 | Bayer Ag | Mehrfach regenerierbare Ionenaustauscherharze mit geringer Alkyl-SH-Gruppen-Belegung |
| US5723691A (en) | 1995-08-31 | 1998-03-03 | General Electric Company | Method for preparing ion-exchange resin for use as a catalyst in the synthesis of bisphenols |
-
2000
- 2000-01-31 CN CNB008042780A patent/CN1173910C/zh not_active Expired - Fee Related
- 2000-01-31 JP JP2000600957A patent/JP2002537116A/ja not_active Ceased
- 2000-01-31 EP EP00905845A patent/EP1163198B1/en not_active Expired - Lifetime
- 2000-01-31 RU RU2001126118/04A patent/RU2001126118A/ru not_active Application Discontinuation
- 2000-01-31 DE DE60006220T patent/DE60006220T2/de not_active Expired - Lifetime
- 2000-01-31 AT AT00905845T patent/ATE253029T1/de not_active IP Right Cessation
- 2000-01-31 BR BR0008481-6A patent/BR0008481A/pt not_active IP Right Cessation
- 2000-01-31 WO PCT/US2000/002339 patent/WO2000050372A1/en not_active Ceased
- 2000-01-31 KR KR1020017010829A patent/KR100693659B1/ko not_active Expired - Fee Related
- 2000-02-15 TW TW089102540A patent/TWI250976B/zh not_active IP Right Cessation
-
2001
- 2001-04-09 US US09/828,721 patent/US6486222B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CN1341089A (zh) | 2002-03-20 |
| RU2001126118A (ru) | 2003-08-10 |
| JP2002537116A (ja) | 2002-11-05 |
| WO2000050372A1 (en) | 2000-08-31 |
| KR20020003196A (ko) | 2002-01-10 |
| KR100693659B1 (ko) | 2007-03-14 |
| US6486222B2 (en) | 2002-11-26 |
| EP1163198B1 (en) | 2003-10-29 |
| ATE253029T1 (de) | 2003-11-15 |
| DE60006220T2 (de) | 2004-07-29 |
| US20020147241A1 (en) | 2002-10-10 |
| BR0008481A (pt) | 2002-01-22 |
| EP1163198A1 (en) | 2001-12-19 |
| DE60006220D1 (de) | 2003-12-04 |
| CN1173910C (zh) | 2004-11-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |