TWI324145B - - Google Patents
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- Publication number
- TWI324145B TWI324145B TW93110379A TW93110379A TWI324145B TW I324145 B TWI324145 B TW I324145B TW 93110379 A TW93110379 A TW 93110379A TW 93110379 A TW93110379 A TW 93110379A TW I324145 B TWI324145 B TW I324145B
- Authority
- TW
- Taiwan
- Prior art keywords
- phenol
- bisphenol
- solution
- recovered
- exchange resin
- Prior art date
Links
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 98
- 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 92
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 50
- 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 claims description 31
- 238000000034 method Methods 0.000 claims description 28
- 239000003456 ion exchange resin Substances 0.000 claims description 27
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 27
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 claims description 23
- 238000004821 distillation Methods 0.000 claims description 22
- 230000002378 acidificating effect Effects 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 229960003495 thiamine Drugs 0.000 claims description 17
- 235000019157 thiamine Nutrition 0.000 claims description 17
- 239000011721 thiamine Substances 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 238000005406 washing Methods 0.000 claims description 16
- -1 thiamine compound Chemical class 0.000 claims description 14
- 238000002425 crystallisation Methods 0.000 claims description 12
- 230000008025 crystallization Effects 0.000 claims description 12
- 239000002994 raw material Substances 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 238000006482 condensation reaction Methods 0.000 claims description 7
- 238000005292 vacuum distillation Methods 0.000 claims description 5
- 238000004064 recycling Methods 0.000 claims description 4
- SNPQRYOQWLOTFA-UHFFFAOYSA-N 2,2-dimethyl-1,3-thiazolidine Chemical compound CC1(C)NCCS1 SNPQRYOQWLOTFA-UHFFFAOYSA-N 0.000 claims description 3
- 238000004140 cleaning Methods 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000012295 chemical reaction liquid Substances 0.000 claims 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 23
- 238000012986 modification Methods 0.000 description 10
- 230000004048 modification Effects 0.000 description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 239000000203 mixture Substances 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- 239000003729 cation exchange resin Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 231100000989 no adverse effect Toxicity 0.000 description 3
- ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- GIPPXXPTVWLFAO-UHFFFAOYSA-N 1-pyridin-4-ylethanethiol Chemical compound CC(S)C1=CC=NC=C1 GIPPXXPTVWLFAO-UHFFFAOYSA-N 0.000 description 1
- FHTDDANQIMVWKZ-UHFFFAOYSA-N 1h-pyridine-4-thione Chemical compound SC1=CC=NC=C1 FHTDDANQIMVWKZ-UHFFFAOYSA-N 0.000 description 1
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical class NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 1
- WCDSVWRUXWCYFN-UHFFFAOYSA-N 4-aminobenzenethiol Chemical compound NC1=CC=C(S)C=C1 WCDSVWRUXWCYFN-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- HSANASOQSCIDJG-UHFFFAOYSA-N OC1=CC=CC=C1.OC1=CC=CC=C1.OC1=CC=CC=C1 Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1.OC1=CC=CC=C1 HSANASOQSCIDJG-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- JXSFMYJZBZPCFI-UHFFFAOYSA-N ethanethiol;pyridine Chemical compound CCS.C1=CC=NC=C1 JXSFMYJZBZPCFI-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 238000011179 visual inspection Methods 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
- C07C37/11—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
- C07C37/70—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
Landscapes
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003108698A JP4615831B2 (ja) | 2003-04-14 | 2003-04-14 | ビスフェノールａの製造におけるフェノールの回収方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200508187A TW200508187A (en) | 2005-03-01 |
| TWI324145B true TWI324145B (ja) | 2010-05-01 |
Family
ID=33295895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW093110379A TW200508187A (en) | 2003-04-14 | 2004-04-14 | Method of recovering phenol in bisphenol A production |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP4615831B2 (ja) |
| CN (1) | CN1771218B (ja) |
| TW (1) | TW200508187A (ja) |
| WO (1) | WO2004092102A1 (ja) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014010510A1 (ja) * | 2012-07-13 | 2014-01-16 | 出光興産株式会社 | ビスフェノールａの製造方法 |
| CN105669388B (zh) * | 2016-03-08 | 2018-09-28 | 江苏常青树新材料科技有限公司 | 一种亚磷酸一苯二异辛酯生产装置上苯酚与异辛醇混合物的分离回收工艺 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3727641A1 (de) * | 1987-08-19 | 1989-03-02 | Bayer Ag | Mit thiazolinen modifizierte ionenaustauscher |
| JP2962441B2 (ja) * | 1991-10-11 | 1999-10-12 | 千代田化工建設株式会社 | 着色性の低いビスフェノールａの製造方法 |
| JPH06340564A (ja) * | 1993-06-01 | 1994-12-13 | Chiyoda Corp | ビスフェノールａの製造方法 |
| JPH09176069A (ja) * | 1995-12-26 | 1997-07-08 | Nippon Steel Chem Co Ltd | ビスフェノール類の製造方法 |
| JPH11246458A (ja) * | 1998-02-26 | 1999-09-14 | Mitsubishi Chemical Corp | ビスフェノールの製造方法 |
| 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 |
| JP2001335522A (ja) * | 2000-05-25 | 2001-12-04 | Mitsubishi Chemicals Corp | ビスフェノールの製造方法 |
| JP4689059B2 (ja) * | 2001-02-28 | 2011-05-25 | 出光興産株式会社 | ビスフェノールａの製造方法 |
-
2003
- 2003-04-14 JP JP2003108698A patent/JP4615831B2/ja not_active Expired - Fee Related
-
2004
- 2004-04-13 WO PCT/JP2004/005239 patent/WO2004092102A1/ja active Application Filing
- 2004-04-13 CN CN200480009711.XA patent/CN1771218B/zh not_active Expired - Fee Related
- 2004-04-14 TW TW093110379A patent/TW200508187A/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1771218A (zh) | 2006-05-10 |
| JP4615831B2 (ja) | 2011-01-19 |
| TW200508187A (en) | 2005-03-01 |
| WO2004092102A1 (ja) | 2004-10-28 |
| JP2004315387A (ja) | 2004-11-11 |
| CN1771218B (zh) | 2010-05-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |