CN107059047A - Sc‑co2体系中电化学制备3‑甲基‑3‑丁烯酸的方法 - Google Patents
Sc‑co2体系中电化学制备3‑甲基‑3‑丁烯酸的方法 Download PDFInfo
- Publication number
- CN107059047A CN107059047A CN201710039848.9A CN201710039848A CN107059047A CN 107059047 A CN107059047 A CN 107059047A CN 201710039848 A CN201710039848 A CN 201710039848A CN 107059047 A CN107059047 A CN 107059047A
- Authority
- CN
- China
- Prior art keywords
- methyl
- butenoic acid
- electrolyte
- carbon dioxide
- fluid
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 27
- 230000005518 electrochemistry Effects 0.000 title claims abstract description 17
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 title abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title abstract description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 68
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 52
- 239000003792 electrolyte Substances 0.000 claims abstract description 37
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000000047 product Substances 0.000 claims abstract description 23
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims abstract description 22
- 238000005868 electrolysis reaction Methods 0.000 claims abstract description 22
- 238000002156 mixing Methods 0.000 claims abstract description 21
- 239000012530 fluid Substances 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 238000005516 engineering process Methods 0.000 claims abstract description 12
- 229910001629 magnesium chloride Inorganic materials 0.000 claims abstract description 11
- 239000007788 liquid Substances 0.000 claims abstract description 10
- -1 methyl imidazolium tetrafluoroborate Chemical compound 0.000 claims abstract description 8
- 239000000706 filtrate Substances 0.000 claims abstract description 7
- 239000002918 waste heat Substances 0.000 claims abstract description 7
- 230000006837 decompression Effects 0.000 claims abstract description 6
- 239000007789 gas Substances 0.000 claims abstract description 6
- 239000002608 ionic liquid Substances 0.000 claims abstract description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 3
- IGRURXZWJCSNKU-UHFFFAOYSA-N Isopropenylacetic acid Chemical compound CC(=C)CC(O)=O IGRURXZWJCSNKU-UHFFFAOYSA-N 0.000 claims description 30
- 239000008151 electrolyte solution Substances 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 238000009826 distribution Methods 0.000 claims description 5
- 238000007710 freezing Methods 0.000 claims description 5
- 230000008014 freezing Effects 0.000 claims description 5
- 238000010792 warming Methods 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 5
- 230000007613 environmental effect Effects 0.000 abstract description 4
- 238000001704 evaporation Methods 0.000 abstract description 4
- 230000008020 evaporation Effects 0.000 abstract description 4
- 239000005431 greenhouse gas Substances 0.000 abstract description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000007818 Grignard reagent Substances 0.000 description 8
- 150000004795 grignard reagents Chemical class 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 5
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 4
- 238000003912 environmental pollution Methods 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical class CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 239000003810 Jones reagent Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- QDOXWKRWXJOMAK-UHFFFAOYSA-N chromium(III) oxide Inorganic materials O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- CPJRRXSHAYUTGL-UHFFFAOYSA-N isopentenyl alcohol Chemical class CC(=C)CCO CPJRRXSHAYUTGL-UHFFFAOYSA-N 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007634 remodeling Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201710039848.9A CN107059047B (zh) | 2017-01-19 | 2017-01-19 | Sc-co2体系中电化学制备3-甲基-3-丁烯酸的方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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CN201710039848.9A CN107059047B (zh) | 2017-01-19 | 2017-01-19 | Sc-co2体系中电化学制备3-甲基-3-丁烯酸的方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN107059047A true CN107059047A (zh) | 2017-08-18 |
CN107059047B CN107059047B (zh) | 2018-12-04 |
Family
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Family Applications (1)
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CN201710039848.9A Active CN107059047B (zh) | 2017-01-19 | 2017-01-19 | Sc-co2体系中电化学制备3-甲基-3-丁烯酸的方法 |
Country Status (1)
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CN (1) | CN107059047B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108808177A (zh) * | 2018-06-14 | 2018-11-13 | 北京理工大学 | 一种离子液体-超临界二氧化碳混合电解质、制备及电池 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101531584A (zh) * | 2009-04-16 | 2009-09-16 | 华东师范大学 | 一种3-丁烯酸的制备方法 |
CN101531585A (zh) * | 2009-04-16 | 2009-09-16 | 华东师范大学 | 一种3-甲基-3-丁烯酸的制备方法 |
CN102719844A (zh) * | 2012-07-03 | 2012-10-10 | 北京化工大学 | 一种苯甲醇氧化制苯甲醛的方法 |
-
2017
- 2017-01-19 CN CN201710039848.9A patent/CN107059047B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101531584A (zh) * | 2009-04-16 | 2009-09-16 | 华东师范大学 | 一种3-丁烯酸的制备方法 |
CN101531585A (zh) * | 2009-04-16 | 2009-09-16 | 华东师范大学 | 一种3-甲基-3-丁烯酸的制备方法 |
CN102719844A (zh) * | 2012-07-03 | 2012-10-10 | 北京化工大学 | 一种苯甲醇氧化制苯甲醛的方法 |
Non-Patent Citations (2)
Title |
---|
DONG-FANG NIU ET AL.,: "Electrocatalytic carboxylation of aliphatic halides at silver cathode in acetonitrile", 《TETRAHEDRON》 * |
JC FOLEST ET AL.,: "Electrocatalyzed carboxylation of organic halides by a cobalt-salen complex", 《TETRAHEDRON LETTERS》 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108808177A (zh) * | 2018-06-14 | 2018-11-13 | 北京理工大学 | 一种离子液体-超临界二氧化碳混合电解质、制备及电池 |
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Publication number | Publication date |
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CN107059047B (zh) | 2018-12-04 |
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TR01 | Transfer of patent right |
Effective date of registration: 20230214 Address after: 312000 South side of Yuzhang Road, Zhangzhen Town, Shangyu District, Shaoxing City, Zhejiang Province Patentee after: Shaoxing Shangyu Eplon Chemical Technology Co.,Ltd. Address before: 315400 Room 303, Building 17, North Area, Jiangnan Huadu A, Yuyao City, Ningbo City, Zhejiang Province Patentee before: Li Dejie |
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TR01 | Transfer of patent right | ||
CI03 | Correction of invention patent |
Correction item: Patentee|Address Correct: Li Dejie|315400 Room 303, Building 17, North Area, Jiangnan Huadu A, Yuyao City, Ningbo City, Zhejiang Province False: Shaoxing Shangyu Eplon Chemical Technology Co.,Ltd.|312000 South side of Yuzhang Road, Zhangzhen Town, Shangyu District, Shaoxing City, Zhejiang Province Number: 08-02 Volume: 39 |
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CI03 | Correction of invention patent | ||
TR01 | Transfer of patent right |
Effective date of registration: 20230315 Address after: 312000 South side of Yuzhang Road, Zhangzhen Town, Shangyu District, Shaoxing City, Zhejiang Province Patentee after: Shaoxing Shangyu eplong Chemical Technology Co.,Ltd. Address before: 315400 Room 303, Building 17, North Area, Jiangnan Huadu A, Yuyao City, Ningbo City, Zhejiang Province Patentee before: Li Dejie |
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TR01 | Transfer of patent right |