RU2401255C2 - Способ выделения фенола из фенолсодержащих потоков производства бисфенола а - Google Patents
Способ выделения фенола из фенолсодержащих потоков производства бисфенола а Download PDFInfo
- Publication number
- RU2401255C2 RU2401255C2 RU2007103892/04A RU2007103892A RU2401255C2 RU 2401255 C2 RU2401255 C2 RU 2401255C2 RU 2007103892/04 A RU2007103892/04 A RU 2007103892/04A RU 2007103892 A RU2007103892 A RU 2007103892A RU 2401255 C2 RU2401255 C2 RU 2401255C2
- Authority
- RU
- Russia
- Prior art keywords
- phenol
- bisphenol
- stream
- column
- distillation column
- Prior art date
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 89
- 238000000034 method Methods 0.000 title claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 title abstract description 10
- 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 claims abstract description 104
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 40
- 238000000926 separation method Methods 0.000 claims abstract description 27
- 238000005292 vacuum distillation Methods 0.000 claims abstract description 10
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 9
- 239000003377 acid catalyst Substances 0.000 claims abstract description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 32
- 230000002378 acidificating effect Effects 0.000 claims description 16
- 238000003776 cleavage reaction Methods 0.000 claims description 16
- 230000007017 scission Effects 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 12
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 230000003993 interaction Effects 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 abstract description 17
- 239000006227 byproduct Substances 0.000 abstract description 12
- 230000000694 effects Effects 0.000 abstract description 4
- 238000000605 extraction Methods 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 1
- 238000004821 distillation Methods 0.000 description 27
- 239000000047 product Substances 0.000 description 22
- 238000002425 crystallisation Methods 0.000 description 13
- 230000008025 crystallization Effects 0.000 description 13
- 239000011347 resin Substances 0.000 description 13
- 229920005989 resin Polymers 0.000 description 13
- 239000007791 liquid phase Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 239000007790 solid phase Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- 239000003456 ion exchange resin Substances 0.000 description 6
- 229920003303 ion-exchange polymer Polymers 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000012452 mother liquor Substances 0.000 description 6
- PBEHQFUSQJKBAS-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;phenol Chemical compound OC1=CC=CC=C1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 PBEHQFUSQJKBAS-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- -1 for example Chemical class 0.000 description 5
- 239000012535 impurity Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000008707 rearrangement Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 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 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000001843 chromanes Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 2
- 150000002468 indanes Chemical class 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- YQDJQYVIHZYJSE-UHFFFAOYSA-N 1-phenyl-2,3-dihydroindene-1,2-diol Chemical class OC1CC2=CC=CC=C2C1(O)C1=CC=CC=C1 YQDJQYVIHZYJSE-UHFFFAOYSA-N 0.000 description 1
- MLCQXUZZAXKTSG-UHFFFAOYSA-N 2-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=C(O)C=C1 MLCQXUZZAXKTSG-UHFFFAOYSA-N 0.000 description 1
- JGDWYKQLFQQIDH-UHFFFAOYSA-N 2-phenyl-3,4-dihydrochromen-2-ol Chemical class C1CC2=CC=CC=C2OC1(O)C1=CC=CC=C1 JGDWYKQLFQQIDH-UHFFFAOYSA-N 0.000 description 1
- WUQYBSRMWWRFQH-UHFFFAOYSA-N 2-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC=C1O WUQYBSRMWWRFQH-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002614 Polyether block amide Polymers 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical class O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000005489 p-toluenesulfonic acid group Chemical class 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
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 238000000066 reactive distillation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003732 xanthenes Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
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
- C07C37/68—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
- 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
- C07C37/86—Purification; separation; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004032232.5 | 2004-07-02 | ||
| DE102004032232A DE102004032232A1 (de) | 2004-07-02 | 2004-07-02 | Verfahren zur Abtrennung von Phenol aus phenolhaltigen Strömen aus der Herstellung von Bisphenol A |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2007103892A RU2007103892A (ru) | 2008-08-10 |
| RU2401255C2 true RU2401255C2 (ru) | 2010-10-10 |
Family
ID=35063346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2007103892/04A RU2401255C2 (ru) | 2004-07-02 | 2005-06-18 | Способ выделения фенола из фенолсодержащих потоков производства бисфенола а |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7301056B2 (https=) |
| EP (1) | EP1765752B1 (https=) |
| JP (1) | JP2008504320A (https=) |
| KR (1) | KR20070028473A (https=) |
| CN (1) | CN1980876B (https=) |
| DE (1) | DE102004032232A1 (https=) |
| ES (1) | ES2550008T3 (https=) |
| RU (1) | RU2401255C2 (https=) |
| WO (1) | WO2006002788A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7858830B2 (en) * | 2008-10-28 | 2010-12-28 | Badger Licensing Llc | Process for recovering phenol from a BPA waste stream |
| US8431749B2 (en) * | 2011-06-06 | 2013-04-30 | Badger Licensing Llc | Recovery of phenol and acetone from bisphenol-A streams |
| TWI557103B (zh) * | 2011-06-06 | 2016-11-11 | 貝吉特許有限責任公司 | 雙酚－ａ殘留物流份之處理 |
| CN104056464B (zh) * | 2014-07-02 | 2015-08-05 | 南通星辰合成材料有限公司 | 以蒸汽喷射与液环真空泵实现双酚a汽提单元真空的方法 |
| WO2022074635A1 (en) * | 2020-10-09 | 2022-04-14 | Sabic Global Technologies B.V. | Phenol recovery of bisphenol-a mother liquor purge using purification train in the phenol production unit |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0812815A2 (en) * | 1996-06-13 | 1997-12-17 | General Electric Company | Process for manufacture of bisphenol |
| US5785823A (en) * | 1995-08-14 | 1998-07-28 | Bayer Ag Konzernverwaltung Rp | Process for the purification of bisphenol |
| RU2139848C1 (ru) * | 1994-04-18 | 1999-10-20 | Байер Аг | Способ очистки бисфенола а |
| US6307111B1 (en) * | 1997-05-16 | 2001-10-23 | Bayer Aktiengesellschaft | Method for continuous production of dihydroxydiarylalkanes |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6015648B2 (ja) * | 1980-09-29 | 1985-04-20 | アイシン化工株式会社 | シエルモ−ルド用樹脂の製造方法 |
| ES2112574T3 (es) | 1994-05-02 | 1998-04-01 | Ferag Ag | Procedimiento y dispositivo para almacenar preformas. |
| US6133486A (en) * | 1998-12-30 | 2000-10-17 | General Electric Company | Phenol recovery from BPA process waste streams |
-
2004
- 2004-07-02 DE DE102004032232A patent/DE102004032232A1/de not_active Withdrawn
-
2005
- 2005-06-18 KR KR1020067027776A patent/KR20070028473A/ko not_active Ceased
- 2005-06-18 ES ES05756999.8T patent/ES2550008T3/es not_active Expired - Lifetime
- 2005-06-18 CN CN2005800225273A patent/CN1980876B/zh not_active Expired - Fee Related
- 2005-06-18 WO PCT/EP2005/006603 patent/WO2006002788A1/de not_active Ceased
- 2005-06-18 EP EP05756999.8A patent/EP1765752B1/de not_active Expired - Lifetime
- 2005-06-18 RU RU2007103892/04A patent/RU2401255C2/ru not_active IP Right Cessation
- 2005-06-18 JP JP2007518497A patent/JP2008504320A/ja not_active Withdrawn
- 2005-06-28 US US11/168,025 patent/US7301056B2/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2139848C1 (ru) * | 1994-04-18 | 1999-10-20 | Байер Аг | Способ очистки бисфенола а |
| US5785823A (en) * | 1995-08-14 | 1998-07-28 | Bayer Ag Konzernverwaltung Rp | Process for the purification of bisphenol |
| EP0812815A2 (en) * | 1996-06-13 | 1997-12-17 | General Electric Company | Process for manufacture of bisphenol |
| US6307111B1 (en) * | 1997-05-16 | 2001-10-23 | Bayer Aktiengesellschaft | Method for continuous production of dihydroxydiarylalkanes |
Also Published As
| Publication number | Publication date |
|---|---|
| US7301056B2 (en) | 2007-11-27 |
| US20060004234A1 (en) | 2006-01-05 |
| ES2550008T3 (es) | 2015-11-03 |
| EP1765752B1 (de) | 2015-08-26 |
| KR20070028473A (ko) | 2007-03-12 |
| DE102004032232A1 (de) | 2006-01-19 |
| WO2006002788A1 (de) | 2006-01-12 |
| RU2007103892A (ru) | 2008-08-10 |
| CN1980876B (zh) | 2010-12-01 |
| JP2008504320A (ja) | 2008-02-14 |
| CN1980876A (zh) | 2007-06-13 |
| EP1765752A1 (de) | 2007-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20110619 |