JP2021536465A - ビスフェノールを製造するプロセス - Google Patents
ビスフェノールを製造するプロセス Download PDFInfo
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- JP2021536465A JP2021536465A JP2021512513A JP2021512513A JP2021536465A JP 2021536465 A JP2021536465 A JP 2021536465A JP 2021512513 A JP2021512513 A JP 2021512513A JP 2021512513 A JP2021512513 A JP 2021512513A JP 2021536465 A JP2021536465 A JP 2021536465A
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- JP
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- Prior art keywords
- catalyst
- bisphenol
- exchange resin
- acetone
- anion exchange
- 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.)
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- 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 title claims abstract description 120
- 238000000034 method Methods 0.000 title claims abstract description 44
- 229930185605 Bisphenol Natural products 0.000 title description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 78
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000003054 catalyst Substances 0.000 claims abstract description 39
- 239000003957 anion exchange resin Substances 0.000 claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 230000002378 acidificating effect Effects 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 239000002638 heterogeneous catalyst Substances 0.000 claims abstract description 8
- 125000001741 organic sulfur group Chemical group 0.000 claims abstract description 7
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 9
- 239000012452 mother liquor Substances 0.000 claims description 9
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical class C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 238000005342 ion exchange Methods 0.000 claims description 5
- -1 alkyl mercaptans Chemical class 0.000 claims description 4
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical class OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 3
- 125000005365 aminothiol group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical class OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 125000001302 tertiary amino group Chemical group 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 abstract description 3
- 238000010586 diagram Methods 0.000 abstract description 2
- CETBSQOFQKLHHZ-UHFFFAOYSA-N Diethyl disulfide Chemical compound CCSSCC CETBSQOFQKLHHZ-UHFFFAOYSA-N 0.000 description 32
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 19
- 238000006482 condensation reaction Methods 0.000 description 18
- LSDPWZHWYPCBBB-UHFFFAOYSA-N methyl mercaptane Natural products SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 18
- 238000009833 condensation Methods 0.000 description 15
- 230000005494 condensation Effects 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 229920001429 chelating resin Polymers 0.000 description 8
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 6
- 239000003377 acid catalyst Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000003729 cation exchange resin Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- ZCLZVWYFTIREFE-UHFFFAOYSA-N 4-benzyl-1-methyl-3,6-dihydro-2h-pyridine;hydrochloride Chemical compound Cl.C1N(C)CCC(CC=2C=CC=CC=2)=C1 ZCLZVWYFTIREFE-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000005349 anion exchange Methods 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 4
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 4
- 239000003456 ion exchange resin Substances 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- 229940023913 cation exchange resins Drugs 0.000 description 3
- 239000007809 chemical reaction catalyst Substances 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000001311 chemical methods and process Methods 0.000 description 2
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 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 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- BBYNYNMPOUQKKS-UHFFFAOYSA-N 2,2-bis(methylsulfanyl)propane Chemical compound CSC(C)(C)SC BBYNYNMPOUQKKS-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 230000001668 ameliorated effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229920003247 engineering thermoplastic Polymers 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000000769 gas chromatography-flame ionisation detection Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 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
- 239000000126 substance Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 150000003548 thiazolidines Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Images
Classifications
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- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/36—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving ionic interaction
- B01D15/361—Ion-exchange
- B01D15/363—Anion-exchange
-
- 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
- C07C37/70—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
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
(a)酸性不均一系触媒と、少なくとも1種の有機硫黄含有化合物を含んでいる触媒促進剤と、を含んでいる触媒系の存在下に、アセトンとフェノールとを反応させて、ビスフェノールA、水、未反応アセトン、未反応フェノール、および触媒促進剤の少なくとも一部を含んでいる反応流出物を製造する工程;
(b)反応流出物の少なくとも一部を蒸留して、水、触媒促進剤および未反応アセトンを除去し、かつビスフェノールAを含有する残余流れを残す工程;
(c)残余流れの少なくとも一部を塩基性アニオン交換樹脂と接触させて、精製された流れを製造する工程;および
(d)精製された流れからビスフェノールAを回収する工程。
[実施例4〜6]
Claims (12)
- ビスフェノールAを製造するプロセスであって、以下の工程を含むプロセス:
(a)酸性不均一系触媒と、少なくとも1種の有機硫黄含有化合物を含んでいる触媒促進剤と、を含んでいる触媒系の存在下に、アセトンとフェノールとを反応させて、ビスフェノールA、水、未反応アセトン、未反応フェノール、および触媒促進剤の少なくとも一部を含んでいる反応流出物を製造する工程;
(b)前記反応流出物の少なくとも一部を蒸留して、水、前記触媒促進剤および未反応アセトンを除去し、かつビスフェノールAを含有する残余流れを残す工程;
(c)前記残余流れの少なくとも一部を塩基性アニオン交換樹脂と接触させて、精製された流れを製造する工程;および
(d)前記精製された流れからビスフェノールAを回収する工程。 - 前記酸性不均一系触媒が、スルホン化イオン交換樹脂を含んでいる、請求項1に記載のプロセス。
- 前記触媒促進剤が、アルキルメルカプタン、メルカプトカルボン酸、メルカプトスルホン酸、メルカプトアルキルピリジン、メルカプトアルキルアミン、チアゾリジンおよびアミノチオールから成る群から選ばれた少なくとも1つの有機硫黄含有化合物を含んでいる、請求項1または2に記載のプロセス。
- 蒸留工程(b)が、155〜185°Cの温度および50〜85kPa−aの圧力で実施される、請求項1〜3のいずれか1項に記載のプロセス。
- 前記残余流れが、1,000重量ppm未満の水、500重量ppm未満のアセトンおよび100重量ppm未満の硫黄含有触媒促進剤を含有する、請求項1〜4のいずれか1項に記載のプロセス。
- 蒸留工程(b)で除去された前記触媒促進剤の少なくとも一部を、反応工程(a)にリサイクルする、請求項1〜5のいずれか1項に記載のプロセス。
- 接触工程(c)が、80〜120°Cの温度で実施される、請求項1〜6のいずれか1項に記載のプロセス。
- 接触工程(c)が、前記塩基性アニオン交換樹脂の床を通り抜ける前記残余流れの下降流によって実施される、請求項1〜7のいずれか1項に記載のプロセス。
- 前記アニオン交換樹脂が、一級、二級または三級アミン基を含有する弱塩基性アニオン交換樹脂である、請求項1〜8のいずれか1項に記載のプロセス。
- 回収工程(d)が、前記精製された流れを固体のビスフェノールA含有製品と母液流れとに分離する晶析を含む、請求項1〜9のいずれか1項に記載のプロセス。
- 前記母液流れが、ビスフェノールA以外のジフェニロールプロパンの他の異性体を含んでおり、かつ前記プロセスが以下の工程をさらに含む、請求項10に記載のプロセス:
(f)前記母液を、前記ジフェニロールプロパンの他の異性体の少なくとも一部をビスフェノールAに変換する条件下で、スルホン化酸性イオン交換触媒と接触させて、異性化された製品流れを製造する工程。 - 以下の工程をさらに含む、請求項11に記載のプロセス:
(g)前記異性化された製品流れの少なくとも一部を反応工程(a)に供給する工程。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201862727230P | 2018-09-05 | 2018-09-05 | |
US62/727,230 | 2018-09-05 | ||
PCT/US2019/049462 WO2020051186A1 (en) | 2018-09-05 | 2019-09-04 | Process for producing bisphenol-a |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2021536465A true JP2021536465A (ja) | 2021-12-27 |
Family
ID=67998721
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2021512513A Pending JP2021536465A (ja) | 2018-09-05 | 2019-09-04 | ビスフェノールを製造するプロセス |
Country Status (9)
Country | Link |
---|---|
US (1) | US20210188750A1 (ja) |
EP (1) | EP3847150B1 (ja) |
JP (1) | JP2021536465A (ja) |
KR (1) | KR20210055062A (ja) |
CN (1) | CN113166011A (ja) |
ES (1) | ES2971879T3 (ja) |
SG (1) | SG11202102127WA (ja) |
TW (1) | TW202030170A (ja) |
WO (1) | WO2020051186A1 (ja) |
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---|---|---|---|---|
JPH01156937A (ja) * | 1987-10-05 | 1989-06-20 | General Electric Co <Ge> | ビスフェノールaの収率および純度を最大にする方法 |
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WO2013061274A1 (en) * | 2011-10-27 | 2013-05-02 | Sabic Innovative Plastics Ip B.V. | Process for producing bisphenol a with reduced sulfur content, polycarbonate made from the bisphenol a, and containers formed from the polycarbonate |
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Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH01211543A (ja) * | 1988-02-17 | 1989-08-24 | Mitsui Toatsu Chem Inc | ビスフェノールaの製造方法 |
US5124490A (en) | 1991-06-17 | 1992-06-23 | General Electric Company | Removal of acids from phenol using anionic exchange resins |
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- 2019-09-04 SG SG11202102127WA patent/SG11202102127WA/en unknown
- 2019-09-04 KR KR1020217009826A patent/KR20210055062A/ko not_active Application Discontinuation
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- 2019-09-04 WO PCT/US2019/049462 patent/WO2020051186A1/en active Application Filing
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ES2971879T3 (es) | 2024-06-10 |
KR20210055062A (ko) | 2021-05-14 |
WO2020051186A1 (en) | 2020-03-12 |
SG11202102127WA (en) | 2021-04-29 |
CN113166011A (zh) | 2021-07-23 |
EP3847150B1 (en) | 2023-11-22 |
US20210188750A1 (en) | 2021-06-24 |
TW202030170A (zh) | 2020-08-16 |
EP3847150A1 (en) | 2021-07-14 |
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