CN107876089B - Ionic liquid catalyst system for bisphenol A synthesis and preparation method thereof - Google Patents
Ionic liquid catalyst system for bisphenol A synthesis and preparation method thereof Download PDFInfo
- Publication number
- CN107876089B CN107876089B CN201711193935.6A CN201711193935A CN107876089B CN 107876089 B CN107876089 B CN 107876089B CN 201711193935 A CN201711193935 A CN 201711193935A CN 107876089 B CN107876089 B CN 107876089B
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- CN
- China
- Prior art keywords
- ionic liquid
- bisphenol
- catalyst system
- liquid catalyst
- molar ratio
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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 112
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 107
- 239000003054 catalyst Substances 0.000 title claims abstract description 91
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 238000001308 synthesis method Methods 0.000 title abstract description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 74
- 239000011831 acidic ionic liquid Substances 0.000 claims abstract description 47
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 31
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 30
- 238000002156 mixing Methods 0.000 claims abstract description 15
- 239000002994 raw material Substances 0.000 claims abstract description 15
- 238000001914 filtration Methods 0.000 claims abstract description 12
- 238000002844 melting Methods 0.000 claims abstract description 12
- 230000008018 melting Effects 0.000 claims abstract description 12
- 239000011259 mixed solution Substances 0.000 claims abstract description 12
- 238000005406 washing Methods 0.000 claims abstract description 12
- 230000002194 synthesizing effect Effects 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 4
- 125000003396 thiol group Chemical class [H]S* 0.000 abstract description 12
- 238000006482 condensation reaction Methods 0.000 abstract description 4
- 239000003960 organic solvent Substances 0.000 abstract description 4
- 230000036632 reaction speed Effects 0.000 abstract description 4
- 230000002195 synergetic effect Effects 0.000 abstract description 3
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 230000007797 corrosion Effects 0.000 description 5
- 238000005260 corrosion Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- WUQYBSRMWWRFQH-UHFFFAOYSA-N 2-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC=C1O WUQYBSRMWWRFQH-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 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 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 1
- 238000012113 quantitative test Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000004065 wastewater treatment 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0285—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre also containing elements or functional groups covered by B01J31/0201 - B01J31/0274
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0298—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature the ionic liquids being characterised by the counter-anions
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201711193935.6A CN107876089B (en) | 2017-11-24 | 2017-11-24 | Ionic liquid catalyst system for bisphenol A synthesis and preparation method thereof |
Applications Claiming Priority (1)
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CN201711193935.6A CN107876089B (en) | 2017-11-24 | 2017-11-24 | Ionic liquid catalyst system for bisphenol A synthesis and preparation method thereof |
Publications (2)
Publication Number | Publication Date |
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CN107876089A CN107876089A (en) | 2018-04-06 |
CN107876089B true CN107876089B (en) | 2020-08-25 |
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CN201711193935.6A Active CN107876089B (en) | 2017-11-24 | 2017-11-24 | Ionic liquid catalyst system for bisphenol A synthesis and preparation method thereof |
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CN (1) | CN107876089B (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110092712B (en) * | 2019-04-10 | 2022-07-01 | 三峡大学 | Preparation method of bisphenol A |
CN111001440A (en) * | 2019-12-26 | 2020-04-14 | 福州大学 | Polyacid site ionic liquid catalyst and preparation method and application thereof |
CN113248441A (en) * | 2021-04-30 | 2021-08-13 | 大连理工大学 | Dual-functional ionic liquid, preparation method thereof and application thereof in catalytic synthesis of bisphenol compound |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1741979A (en) * | 2002-12-12 | 2006-03-01 | 通用电气公司 | Process for the synthesis of bisphenol |
US20110178306A1 (en) * | 2005-12-12 | 2011-07-21 | Phostech Lithium Inc. | Sulphonyl-1,2,4-Triazole Salts |
CN102701955A (en) * | 2012-05-10 | 2012-10-03 | 中科院广州化学有限公司 | Application of acidic ionic liquid in catalyzing and synthesizing diphenolic acid and/or diphenolic acid ester |
US20150158801A1 (en) * | 2011-09-23 | 2015-06-11 | Kun Wang | Process for Producing Phenol |
CN105669384A (en) * | 2015-12-27 | 2016-06-15 | 湘潭大学 | Method of catalytically synthesizing biphenol F being high in 4-4' isomer content |
-
2017
- 2017-11-24 CN CN201711193935.6A patent/CN107876089B/en active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1741979A (en) * | 2002-12-12 | 2006-03-01 | 通用电气公司 | Process for the synthesis of bisphenol |
US20110178306A1 (en) * | 2005-12-12 | 2011-07-21 | Phostech Lithium Inc. | Sulphonyl-1,2,4-Triazole Salts |
US20150158801A1 (en) * | 2011-09-23 | 2015-06-11 | Kun Wang | Process for Producing Phenol |
CN102701955A (en) * | 2012-05-10 | 2012-10-03 | 中科院广州化学有限公司 | Application of acidic ionic liquid in catalyzing and synthesizing diphenolic acid and/or diphenolic acid ester |
CN105669384A (en) * | 2015-12-27 | 2016-06-15 | 湘潭大学 | Method of catalytically synthesizing biphenol F being high in 4-4' isomer content |
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CN107876089A (en) | 2018-04-06 |
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PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
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GR01 | Patent grant | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20230222 Address after: 457500 puwang Industrial Park, fan County, Puyang City, Henan Province Patentee after: PUYANG SHENGTONGJUYUAN ADVANCED MATERIALS Co.,Ltd. Address before: 100098 b-1907, 16th floor, building 1, 18 Zhongguancun East Road, Haidian District, Beijing Patentee before: PEKING PUYUAN INSTITUTE FOR ADVANCED MATERIALS AND TECHNOLOGY |
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PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Ionic liquid catalyst system and preparation method for bisphenol A synthesis Effective date of registration: 20230720 Granted publication date: 20200825 Pledgee: China Petroleum Finance Co.,Ltd. Pledgor: PUYANG SHENGTONGJUYUAN ADVANCED MATERIALS Co.,Ltd. Registration number: Y2023980048997 |
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PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Granted publication date: 20200825 Pledgee: China Petroleum Finance Co.,Ltd. Pledgor: PUYANG SHENGTONGJUYUAN ADVANCED MATERIALS Co.,Ltd. Registration number: Y2023980048997 |
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PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Ionic liquid catalyst system and preparation method for the synthesis of bisphenol A Granted publication date: 20200825 Pledgee: China Petroleum Finance Co.,Ltd. Pledgor: PUYANG SHENGTONGJUYUAN ADVANCED MATERIALS Co.,Ltd. Registration number: Y2024980021619 |
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PE01 | Entry into force of the registration of the contract for pledge of patent right |