RU2384558C2 - Способ получения бисфенола а - Google Patents
Способ получения бисфенола а Download PDFInfo
- Publication number
- RU2384558C2 RU2384558C2 RU2006110205/04A RU2006110205A RU2384558C2 RU 2384558 C2 RU2384558 C2 RU 2384558C2 RU 2006110205/04 A RU2006110205/04 A RU 2006110205/04A RU 2006110205 A RU2006110205 A RU 2006110205A RU 2384558 C2 RU2384558 C2 RU 2384558C2
- Authority
- RU
- Russia
- Prior art keywords
- acetone
- methanol
- reaction
- concentration
- phenol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 50
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 318
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 261
- 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 91
- 238000006243 chemical reaction Methods 0.000 claims abstract description 81
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 52
- 239000003054 catalyst Substances 0.000 claims abstract description 28
- 238000004821 distillation Methods 0.000 claims abstract description 23
- 239000012535 impurity Substances 0.000 claims abstract description 21
- 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 abstract description 18
- 239000003729 cation exchange resin Substances 0.000 claims abstract description 13
- 238000004064 recycling Methods 0.000 claims abstract description 7
- -1 amine compound Chemical class 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 239000007858 starting material Substances 0.000 claims description 14
- 230000002378 acidificating effect Effects 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 239000003456 ion exchange resin Substances 0.000 claims description 7
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 230000003993 interaction Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 26
- 238000004519 manufacturing process Methods 0.000 abstract description 15
- 230000000694 effects Effects 0.000 abstract description 9
- 239000012452 mother liquor Substances 0.000 description 39
- 239000007788 liquid Substances 0.000 description 34
- 238000000926 separation method Methods 0.000 description 30
- 238000009835 boiling Methods 0.000 description 25
- 239000007787 solid Substances 0.000 description 25
- 238000002425 crystallisation Methods 0.000 description 22
- 230000008025 crystallization Effects 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229940023913 cation exchange resins Drugs 0.000 description 4
- 230000009849 deactivation Effects 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- VBAOEVKQBLGWTH-UHFFFAOYSA-N 2-pyridin-4-ylethanethiol Chemical compound SCCC1=CC=NC=C1 VBAOEVKQBLGWTH-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004332 deodorization Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- 229910018994 (KOHYO) No Inorganic materials 0.000 description 1
- SNPQRYOQWLOTFA-UHFFFAOYSA-N 2,2-dimethyl-1,3-thiazolidine Chemical compound CC1(C)NCCS1 SNPQRYOQWLOTFA-UHFFFAOYSA-N 0.000 description 1
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 1
- HSAYSFNFCZEPCN-UHFFFAOYSA-N 3-(dimethylamino)propane-1-thiol Chemical compound CN(C)CCCS HSAYSFNFCZEPCN-UHFFFAOYSA-N 0.000 description 1
- IYGAMTQMILRCCI-UHFFFAOYSA-N 3-aminopropane-1-thiol Chemical compound NCCCS IYGAMTQMILRCCI-UHFFFAOYSA-N 0.000 description 1
- YLXAAHHOPYLRJV-UHFFFAOYSA-N 4-(dibutylamino)butane-1-thiol Chemical compound CCCCN(CCCC)CCCCS YLXAAHHOPYLRJV-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009841 combustion method Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- 239000002781 deodorant agent Substances 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
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 235000016709 nutrition Nutrition 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
- 238000006385 ozonation reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000001699 photocatalysis Effects 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003383991 | 2003-11-13 | ||
| JP2003-383991 | 2003-11-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2006110205A RU2006110205A (ru) | 2007-10-10 |
| RU2384558C2 true RU2384558C2 (ru) | 2010-03-20 |
Family
ID=34587307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2006110205/04A RU2384558C2 (ru) | 2003-11-13 | 2004-11-05 | Способ получения бисфенола а |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20060211893A1 (enExample) |
| EP (1) | EP1683779A4 (enExample) |
| KR (1) | KR101090192B1 (enExample) |
| CN (1) | CN100582069C (enExample) |
| BR (1) | BRPI0415552B1 (enExample) |
| RU (1) | RU2384558C2 (enExample) |
| TW (1) | TW200526565A (enExample) |
| WO (1) | WO2005047222A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2619461C2 (ru) * | 2012-04-16 | 2017-05-16 | Инстытут Ценжкей Сынтезы Органичней "Бляховня" | Способ получения бисфенола a |
| RU2782457C2 (ru) * | 2018-07-06 | 2022-10-27 | Бэджер Лайсенсинг Ллс | Обработка остаточных потоков от производства бисфенолов |
Families Citing this family (7)
| 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 |
| CN101790505B (zh) * | 2007-08-29 | 2013-12-11 | 陶氏环球技术公司 | 在双酚a生产工艺中减少再循环流中的甲醇的方法 |
| RU2627266C2 (ru) * | 2012-06-28 | 2017-08-04 | Идемицу Козан Ко., Лтд. | Способ получения бисфенола |
| US10005709B2 (en) | 2016-05-10 | 2018-06-26 | Sabic Global Technologies B.V. | Method for producing a Bisphenol |
| KR102040820B1 (ko) * | 2016-11-28 | 2019-11-06 | 주식회사 엘지화학 | 메탄올 및 아세톤의 제거 유닛 및 이를 포함하는 페놀 및 비스페놀 a의 제조 시스템 |
| 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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001503377A (ja) * | 1995-12-19 | 2001-03-13 | シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ | ビスフェノールの改良された製造方法 |
| JP2002255880A (ja) * | 2001-03-01 | 2002-09-11 | Idemitsu Petrochem Co Ltd | ビスフェノールａの製造方法 |
Family Cites Families (5)
| 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 |
| 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 CN CN200480030557A patent/CN100582069C/zh not_active Expired - Lifetime
- 2004-11-05 EP EP04818457A patent/EP1683779A4/en not_active Withdrawn
- 2004-11-05 RU RU2006110205/04A patent/RU2384558C2/ru active
- 2004-11-05 BR BRPI0415552-1A patent/BRPI0415552B1/pt not_active IP Right Cessation
- 2004-11-05 WO PCT/JP2004/016406 patent/WO2005047222A1/ja not_active Ceased
- 2004-11-05 KR KR1020067006570A patent/KR101090192B1/ko 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
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001503377A (ja) * | 1995-12-19 | 2001-03-13 | シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ | ビスフェノールの改良された製造方法 |
| JP2002255880A (ja) * | 2001-03-01 | 2002-09-11 | Idemitsu Petrochem Co Ltd | ビスフェノールａの製造方法 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2619461C2 (ru) * | 2012-04-16 | 2017-05-16 | Инстытут Ценжкей Сынтезы Органичней "Бляховня" | Способ получения бисфенола a |
| RU2782457C2 (ru) * | 2018-07-06 | 2022-10-27 | Бэджер Лайсенсинг Ллс | Обработка остаточных потоков от производства бисфенолов |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1867533A (zh) | 2006-11-22 |
| CN100582069C (zh) | 2010-01-20 |
| TWI331990B (enExample) | 2010-10-21 |
| KR101090192B1 (ko) | 2011-12-06 |
| EP1683779A4 (en) | 2007-08-29 |
| BRPI0415552A (pt) | 2006-12-26 |
| EP1683779A1 (en) | 2006-07-26 |
| KR20060117311A (ko) | 2006-11-16 |
| TW200526565A (en) | 2005-08-16 |
| WO2005047222A1 (ja) | 2005-05-26 |
| BRPI0415552B1 (pt) | 2014-04-29 |
| RU2006110205A (ru) | 2007-10-10 |
| US20060211893A1 (en) | 2006-09-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD4A | Correction of name of patent owner | ||
| PC43 | Official registration of the transfer of the exclusive right without contract for inventions |
Effective date: 20171102 |
|
| PD4A | Correction of name of patent owner |