TWI331990B - - Google Patents
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- Publication number
- TWI331990B TWI331990B TW093134333A TW93134333A TWI331990B TW I331990 B TWI331990 B TW I331990B TW 093134333 A TW093134333 A TW 093134333A TW 93134333 A TW93134333 A TW 93134333A TW I331990 B TWI331990 B TW I331990B
- Authority
- TW
- Taiwan
- Prior art keywords
- acetone
- reaction step
- supplied
- methanol
- concentration
- Prior art date
Links
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 304
- 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 89
- 238000006243 chemical reaction Methods 0.000 claims description 81
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 49
- 238000004821 distillation Methods 0.000 claims description 31
- 239000003054 catalyst Substances 0.000 claims description 28
- 239000002994 raw material Substances 0.000 claims description 27
- 238000004519 manufacturing process Methods 0.000 claims description 22
- 239000012535 impurity Substances 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 230000002378 acidificating effect Effects 0.000 claims description 15
- -1 thiamine compound Chemical class 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 claims description 6
- 229960003495 thiamine Drugs 0.000 claims description 6
- 235000019157 thiamine Nutrition 0.000 claims description 6
- 239000011721 thiamine Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 239000012295 chemical reaction liquid Substances 0.000 claims description 4
- 229930185605 Bisphenol Natural products 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 231
- 239000007788 liquid Substances 0.000 description 52
- 238000000034 method Methods 0.000 description 42
- 238000002425 crystallisation Methods 0.000 description 32
- 238000000926 separation method Methods 0.000 description 32
- 230000008025 crystallization Effects 0.000 description 31
- 238000009835 boiling Methods 0.000 description 26
- 239000012452 mother liquor Substances 0.000 description 26
- 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 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 239000003729 cation exchange resin Substances 0.000 description 11
- 239000013078 crystal Substances 0.000 description 10
- 239000002002 slurry Substances 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 7
- 230000006866 deterioration Effects 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 239000003456 ion exchange resin Substances 0.000 description 5
- 229920003303 ion-exchange polymer Polymers 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 238000009841 combustion method Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000004332 deodorization Methods 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000000126 substance Substances 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
- 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
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001356 alkyl thiols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001877 deodorizing effect Effects 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940093495 ethanethiol Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- FTDXCHCAMNRNNY-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1 FTDXCHCAMNRNNY-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 239000011941 photocatalyst Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- JXHZRQHZVYDRGX-UHFFFAOYSA-M sodium;hydrogen sulfate;hydrate Chemical compound [OH-].[Na+].OS(O)(=O)=O JXHZRQHZVYDRGX-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 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
- C07C37/82—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)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003383991 | 2003-11-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200526565A TW200526565A (en) | 2005-08-16 |
| TWI331990B true TWI331990B (https=) | 2010-10-21 |
Family
ID=34587307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW093134333A TW200526565A (en) | 2003-11-13 | 2004-11-10 | Method for producing bisphenol A |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20060211893A1 (https=) |
| EP (1) | EP1683779A4 (https=) |
| KR (1) | KR101090192B1 (https=) |
| CN (1) | CN100582069C (https=) |
| BR (1) | BRPI0415552B1 (https=) |
| RU (1) | RU2384558C2 (https=) |
| TW (1) | TW200526565A (https=) |
| WO (1) | WO2005047222A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4918264B2 (ja) * | 2006-02-02 | 2012-04-18 | 出光興産株式会社 | ビスフェノールａの回収方法および回収設備 |
| KR101593706B1 (ko) * | 2007-08-29 | 2016-02-15 | 블루 큐브 아이피 엘엘씨 | 비스페놀-ａ 제조 공정에서 재순환 스트림 중의 메탄올을 감소시키는 방법 |
| PL217484B1 (pl) * | 2012-04-16 | 2014-07-31 | Inst Ciężkiej Syntezy Organicznej Blachownia | Sposób otrzymywania bisfenolu A |
| WO2014002787A1 (ja) * | 2012-06-28 | 2014-01-03 | 出光興産株式会社 | ビスフェノールａの製造方法 |
| US10005709B2 (en) | 2016-05-10 | 2018-06-26 | Sabic Global Technologies B.V. | Method for producing a Bisphenol |
| CN109790096B (zh) * | 2016-11-28 | 2022-03-15 | 株式会社Lg化学 | 甲醇、丙酮去除单元及含该单元的苯酚、双酚a生产系统 |
| EP3466915B1 (en) * | 2017-10-06 | 2019-11-27 | SABIC Global Technologies B.V. | Method of purifying acetone |
| KR102542336B1 (ko) * | 2022-12-15 | 2023-06-13 | 송원산업 주식회사 | 4,4'-（3,5,5-트리메틸 시클로헥실리덴）비스페놀류 화합물 제조 방법 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5780690A (en) * | 1992-04-28 | 1998-07-14 | Bayer Aktiengesellschaft | Bisphenol synthesis on modified ion-exchange resins using specially purified carbonyl compounds |
| JP3475960B2 (ja) * | 1992-09-11 | 2003-12-10 | 出光石油化学株式会社 | ２，２−ビス（４−ヒドロキシフェニル）プロパンの製造方法 |
| CN1205683A (zh) * | 1995-12-19 | 1999-01-20 | 国际壳牌研究有限公司 | 生产双酚的改进方法 |
| WO1997022573A1 (en) * | 1995-12-19 | 1997-06-26 | Shell Internationale Research Maatschappij B.V. | Improved process for the production of bisphenols |
| JP4723105B2 (ja) * | 2001-03-01 | 2011-07-13 | 出光興産株式会社 | ビスフェノールａ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 |
| US7112702B2 (en) * | 2002-12-12 | 2006-09-26 | General Electric Company | Process for the synthesis of bisphenol |
-
2004
- 2004-11-05 EP EP04818457A patent/EP1683779A4/en not_active Withdrawn
- 2004-11-05 BR BRPI0415552-1A patent/BRPI0415552B1/pt not_active IP Right Cessation
- 2004-11-05 KR KR1020067006570A patent/KR101090192B1/ko not_active Expired - Lifetime
- 2004-11-05 RU RU2006110205/04A patent/RU2384558C2/ru active
- 2004-11-05 WO PCT/JP2004/016406 patent/WO2005047222A1/ja not_active Ceased
- 2004-11-05 CN CN200480030557A patent/CN100582069C/zh not_active Expired - Lifetime
- 2004-11-10 TW TW093134333A patent/TW200526565A/zh not_active IP Right Cessation
-
2006
- 2006-03-20 US US11/378,637 patent/US20060211893A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| TW200526565A (en) | 2005-08-16 |
| WO2005047222A1 (ja) | 2005-05-26 |
| CN1867533A (zh) | 2006-11-22 |
| KR101090192B1 (ko) | 2011-12-06 |
| US20060211893A1 (en) | 2006-09-21 |
| RU2384558C2 (ru) | 2010-03-20 |
| CN100582069C (zh) | 2010-01-20 |
| KR20060117311A (ko) | 2006-11-16 |
| RU2006110205A (ru) | 2007-10-10 |
| BRPI0415552B1 (pt) | 2014-04-29 |
| EP1683779A4 (en) | 2007-08-29 |
| EP1683779A1 (en) | 2006-07-26 |
| BRPI0415552A (pt) | 2006-12-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4A | Expiration of patent term of an invention patent |