CN106637283A - 一种全氟甲基环己烷的制备方法 - Google Patents
一种全氟甲基环己烷的制备方法 Download PDFInfo
- Publication number
- CN106637283A CN106637283A CN201611046140.8A CN201611046140A CN106637283A CN 106637283 A CN106637283 A CN 106637283A CN 201611046140 A CN201611046140 A CN 201611046140A CN 106637283 A CN106637283 A CN 106637283A
- Authority
- CN
- China
- Prior art keywords
- pfmch
- perfluoromethylcyclohexane
- preparation
- product
- electrolysis
- 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
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- QIROQPWSJUXOJC-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6-undecafluoro-6-(trifluoromethyl)cyclohexane Chemical compound FC(F)(F)C1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F QIROQPWSJUXOJC-UHFFFAOYSA-N 0.000 title claims abstract description 83
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 36
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000005868 electrolysis reaction Methods 0.000 claims abstract description 32
- 239000012071 phase Substances 0.000 claims abstract description 20
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 15
- 239000012074 organic phase Substances 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 239000003792 electrolyte Substances 0.000 claims abstract description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 55
- 239000000047 product Substances 0.000 claims description 43
- 239000012043 crude product Substances 0.000 claims description 21
- 239000007788 liquid Substances 0.000 claims description 19
- 239000005416 organic matter Substances 0.000 claims description 13
- 238000000926 separation method Methods 0.000 claims description 12
- -1 cyclohexyl acyl chlorides Chemical class 0.000 claims description 11
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 5
- 239000005711 Benzoic acid Substances 0.000 claims description 4
- 235000010233 benzoic acid Nutrition 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- CHCFOMQHQIQBLZ-UHFFFAOYSA-N azane;phthalic acid Chemical compound N.N.OC(=O)C1=CC=CC=C1C(O)=O CHCFOMQHQIQBLZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000036647 reaction Effects 0.000 claims description 2
- 229960004365 benzoic acid Drugs 0.000 claims 2
- WQPDQJCBHQPNCZ-UHFFFAOYSA-N cyclohexa-2,4-dien-1-one Chemical group O=C1CC=CC=C1 WQPDQJCBHQPNCZ-UHFFFAOYSA-N 0.000 claims 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims 2
- GOKQOZYJEDDDOC-UHFFFAOYSA-N C(=O)OC.C1=CC=CC=C1 Chemical group C(=O)OC.C1=CC=CC=C1 GOKQOZYJEDDDOC-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- GFAUNYMRSKVDJL-UHFFFAOYSA-N formyl chloride Chemical compound ClC=O GFAUNYMRSKVDJL-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 abstract description 7
- 239000003513 alkali Substances 0.000 abstract description 4
- 238000005516 engineering process Methods 0.000 abstract description 2
- 238000004334 fluoridation Methods 0.000 abstract 2
- 238000004134 energy conservation Methods 0.000 abstract 1
- 230000007613 environmental effect Effects 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 30
- 238000000034 method Methods 0.000 description 11
- 230000005611 electricity Effects 0.000 description 10
- 238000003682 fluorination reaction Methods 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 6
- 239000012535 impurity Substances 0.000 description 5
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- CYMRPDYINXWJFU-UHFFFAOYSA-N 2-carbamoylbenzoic acid Chemical class NC(=O)C1=CC=CC=C1C(O)=O CYMRPDYINXWJFU-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000002482 conductive additive Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 229940095102 methyl benzoate Drugs 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000002000 Electrolyte additive Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011265 semifinished product Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 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
- C25B3/20—Processes
- C25B3/27—Halogenation
- C25B3/28—Fluorination
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (9)
Priority Applications (1)
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CN201611046140.8A CN106637283B (zh) | 2016-11-22 | 2016-11-22 | 一种全氟甲基环己烷的制备方法 |
Applications Claiming Priority (1)
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CN201611046140.8A CN106637283B (zh) | 2016-11-22 | 2016-11-22 | 一种全氟甲基环己烷的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN106637283A true CN106637283A (zh) | 2017-05-10 |
CN106637283B CN106637283B (zh) | 2018-08-07 |
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CN201611046140.8A Active CN106637283B (zh) | 2016-11-22 | 2016-11-22 | 一种全氟甲基环己烷的制备方法 |
Country Status (1)
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CN (1) | CN106637283B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107604378A (zh) * | 2017-10-19 | 2018-01-19 | 浙江巨圣氟化学有限公司 | 一种全氟已烷的制备方法 |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3871975A (en) * | 1972-06-01 | 1975-03-18 | Shunji Nagase | Electrolytic process for production of perfluorocyclohexane derivatives |
US3876515A (en) * | 1972-12-27 | 1975-04-08 | Agency Ind Science Techn | Method for manufacture of perfluorocyclohexane derivatives |
CN1106077A (zh) * | 1993-08-31 | 1995-08-02 | 美国3M公司 | 含氟化合物的制备方法 |
CN1144545A (zh) * | 1994-03-29 | 1997-03-05 | 美国3M公司 | 制备支化全氟化学品的方法 |
CN1450204A (zh) * | 2003-05-08 | 2003-10-22 | 樊福定 | 全氟三丁胺的工业化制备方法 |
RU2430909C1 (ru) * | 2010-03-17 | 2011-10-10 | Федеральное государственное унитарное предприятие "Российский научный центр "Прикладная химия" | Способ получения фторангидрида перфторциклогексанкарбоновой кислоты |
CN103261484A (zh) * | 2010-12-15 | 2013-08-21 | 巴斯夫欧洲公司 | 有机化合物的电化学氟化方法 |
CN104805467A (zh) * | 2015-03-26 | 2015-07-29 | 浙江巨圣氟化学有限公司 | 一种全氟环已基甲酰氟的制备方法 |
-
2016
- 2016-11-22 CN CN201611046140.8A patent/CN106637283B/zh active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3871975A (en) * | 1972-06-01 | 1975-03-18 | Shunji Nagase | Electrolytic process for production of perfluorocyclohexane derivatives |
US3876515A (en) * | 1972-12-27 | 1975-04-08 | Agency Ind Science Techn | Method for manufacture of perfluorocyclohexane derivatives |
CN1106077A (zh) * | 1993-08-31 | 1995-08-02 | 美国3M公司 | 含氟化合物的制备方法 |
CN1144545A (zh) * | 1994-03-29 | 1997-03-05 | 美国3M公司 | 制备支化全氟化学品的方法 |
CN1450204A (zh) * | 2003-05-08 | 2003-10-22 | 樊福定 | 全氟三丁胺的工业化制备方法 |
RU2430909C1 (ru) * | 2010-03-17 | 2011-10-10 | Федеральное государственное унитарное предприятие "Российский научный центр "Прикладная химия" | Способ получения фторангидрида перфторциклогексанкарбоновой кислоты |
CN103261484A (zh) * | 2010-12-15 | 2013-08-21 | 巴斯夫欧洲公司 | 有机化合物的电化学氟化方法 |
CN104805467A (zh) * | 2015-03-26 | 2015-07-29 | 浙江巨圣氟化学有限公司 | 一种全氟环已基甲酰氟的制备方法 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107604378A (zh) * | 2017-10-19 | 2018-01-19 | 浙江巨圣氟化学有限公司 | 一种全氟已烷的制备方法 |
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Publication number | Publication date |
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CN106637283B (zh) | 2018-08-07 |
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Effective date of registration: 20240423 Address after: 324000 Kecheng District, Quzhou City, Zhejiang Province Patentee after: ZHEJIANG JUSHENG FLUOROCHEMICAL CO.,LTD. Country or region after: China Address before: 324004 No.6 Zhongxing Road, Kecheng District, Quzhou City, Zhejiang Province Patentee before: ZHEJIANG JUSHENG FLUOROCHEMICAL CO.,LTD. Country or region before: China Patentee before: ZHEJIANG JUHUA Co.,Ltd. FLUOR POLYMERIC PLANT |
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