GB1565667A - Deculouration of bipshenol-a recycle stream with cation exchange resin - Google Patents
Deculouration of bipshenol-a recycle stream with cation exchange resin Download PDFInfo
- Publication number
- GB1565667A GB1565667A GB3918676A GB3918676A GB1565667A GB 1565667 A GB1565667 A GB 1565667A GB 3918676 A GB3918676 A GB 3918676A GB 3918676 A GB3918676 A GB 3918676A GB 1565667 A GB1565667 A GB 1565667A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenol
- water
- mother liquor
- recycle stream
- bisphenol
- 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.)
- Expired
Links
- 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 description 26
- 239000003729 cation exchange resin Substances 0.000 title claims description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 52
- 239000012452 mother liquor Substances 0.000 claims description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 42
- 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 description 41
- 238000000034 method Methods 0.000 claims description 38
- 238000002835 absorbance Methods 0.000 claims description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 22
- 239000011347 resin Substances 0.000 claims description 17
- 229920005989 resin Polymers 0.000 claims description 17
- 230000002378 acidificating effect Effects 0.000 claims description 16
- 239000003463 adsorbent Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 238000001179 sorption measurement Methods 0.000 claims description 11
- 239000012535 impurity Substances 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000003377 acid catalyst Substances 0.000 claims description 5
- 125000002091 cationic group Chemical group 0.000 claims description 5
- 238000003795 desorption Methods 0.000 claims description 4
- 230000001186 cumulative effect Effects 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000005259 measurement Methods 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 238000010908 decantation Methods 0.000 claims description 2
- 230000006326 desulfonation Effects 0.000 claims description 2
- 238000005869 desulfonation reaction Methods 0.000 claims description 2
- 238000002474 experimental method Methods 0.000 claims description 2
- 238000007710 freezing Methods 0.000 claims description 2
- 230000008014 freezing Effects 0.000 claims description 2
- KSSNXJHPEFVKHY-UHFFFAOYSA-N phenol;hydrate Chemical compound O.OC1=CC=CC=C1 KSSNXJHPEFVKHY-UHFFFAOYSA-N 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 238000002791 soaking Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000523 sample Substances 0.000 description 14
- 239000003456 ion exchange resin Substances 0.000 description 13
- 229920003303 ion-exchange polymer Polymers 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- NUHSROFQTUXZQQ-UHFFFAOYSA-N isopentenyl diphosphate Chemical compound CC(=C)CCO[P@](O)(=O)OP(O)(O)=O NUHSROFQTUXZQQ-UHFFFAOYSA-N 0.000 description 8
- 238000010926 purge Methods 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 229940106691 bisphenol a Drugs 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical class C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- 230000000274 adsorptive effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 238000011067 equilibration Methods 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- JAGRUUPXPPLSRX-UHFFFAOYSA-N 4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C=C1 JAGRUUPXPPLSRX-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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
- C07C37/82—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by solid-liquid treatment; by chemisorption
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61602675A | 1975-09-23 | 1975-09-23 | |
| US69672676A | 1976-06-16 | 1976-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1565667A true GB1565667A (en) | 1980-04-23 |
Family
ID=27087657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3918676A Expired GB1565667A (en) | 1975-09-23 | 1976-09-22 | Deculouration of bipshenol-a recycle stream with cation exchange resin |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5242861A (enrdf_load_stackoverflow) |
| DE (1) | DE2642596A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2325627A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1565667A (enrdf_load_stackoverflow) |
| IT (1) | IT1071481B (enrdf_load_stackoverflow) |
| NL (1) | NL7610522A (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4954661A (en) * | 1988-03-11 | 1990-09-04 | Mitsui Toatsu Chemicals, Inc. | Process for preparing high-purity bisphenol A |
| US6680270B2 (en) | 2001-04-24 | 2004-01-20 | General Electric Company | Regeneration of catalysts used in the manufacture of bisphenols |
| EP1149816A4 (en) * | 1999-12-03 | 2004-04-07 | Mitsui Chemicals Inc | HIGH QUALITY BISPHENOL A AND METHOD FOR THE PRODUCTION THEREOF |
| US7696388B2 (en) | 2008-07-09 | 2010-04-13 | Sabic Innovative Plastics Ip B.V. | Process for producing bisphenol-A |
| CN104379546A (zh) * | 2012-06-28 | 2015-02-25 | 出光兴产株式会社 | 双酚a的制备方法 |
| US11312822B2 (en) | 2017-01-17 | 2022-04-26 | Sabic Global Technologies B.V. | Reduced color polycarbonate compositions, methods of manufacture, and articles thereof |
| US12084542B2 (en) | 2018-12-05 | 2024-09-10 | Sabic Global Technologies B.V. | Polycarbonate compositions with improved oxidation stability and methods of manufacturing the same |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4051079A (en) * | 1976-06-22 | 1977-09-27 | Union Carbide Corporation | Regeneration of acidic cation exchange resin using acidified phenol-water mixture |
| DE2860850D1 (en) * | 1977-11-09 | 1981-10-22 | Shell Int Research | Preparation of bisphenols |
| US4636393A (en) * | 1984-11-28 | 1987-01-13 | Campbell Soup Company | Method of processing meat for inclusion in high acid type foods and product thereof |
| 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 |
| JPH0365408U (enrdf_load_stackoverflow) * | 1989-10-30 | 1991-06-26 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2222607A1 (de) * | 1972-05-09 | 1973-11-22 | Rheinstahl Ag | Ringwalzwerk |
-
1976
- 1976-09-22 IT IT2751276A patent/IT1071481B/it active
- 1976-09-22 DE DE19762642596 patent/DE2642596A1/de not_active Ceased
- 1976-09-22 NL NL7610522A patent/NL7610522A/xx not_active Application Discontinuation
- 1976-09-22 JP JP11316276A patent/JPS5242861A/ja active Granted
- 1976-09-22 FR FR7628514A patent/FR2325627A1/fr not_active Withdrawn
- 1976-09-22 GB GB3918676A patent/GB1565667A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4954661A (en) * | 1988-03-11 | 1990-09-04 | Mitsui Toatsu Chemicals, Inc. | Process for preparing high-purity bisphenol A |
| EP1149816A4 (en) * | 1999-12-03 | 2004-04-07 | Mitsui Chemicals Inc | HIGH QUALITY BISPHENOL A AND METHOD FOR THE PRODUCTION THEREOF |
| US6680270B2 (en) | 2001-04-24 | 2004-01-20 | General Electric Company | Regeneration of catalysts used in the manufacture of bisphenols |
| US7696388B2 (en) | 2008-07-09 | 2010-04-13 | Sabic Innovative Plastics Ip B.V. | Process for producing bisphenol-A |
| CN104379546A (zh) * | 2012-06-28 | 2015-02-25 | 出光兴产株式会社 | 双酚a的制备方法 |
| CN104379546B (zh) * | 2012-06-28 | 2018-10-09 | 出光兴产株式会社 | 双酚a的制备方法 |
| US11312822B2 (en) | 2017-01-17 | 2022-04-26 | Sabic Global Technologies B.V. | Reduced color polycarbonate compositions, methods of manufacture, and articles thereof |
| US12084542B2 (en) | 2018-12-05 | 2024-09-10 | Sabic Global Technologies B.V. | Polycarbonate compositions with improved oxidation stability and methods of manufacturing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5534779B2 (enrdf_load_stackoverflow) | 1980-09-09 |
| DE2642596A1 (de) | 1977-04-07 |
| NL7610522A (nl) | 1977-03-25 |
| IT1071481B (it) | 1985-04-10 |
| FR2325627A1 (fr) | 1977-04-22 |
| JPS5242861A (en) | 1977-04-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |