RU2020112285A - Соединение, содержащее фторсульфонильную группу, мономер, содержащий фторсульфонильную группу, и способы их получения - Google Patents
Соединение, содержащее фторсульфонильную группу, мономер, содержащий фторсульфонильную группу, и способы их получения Download PDFInfo
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- RU2020112285A RU2020112285A RU2020112285A RU2020112285A RU2020112285A RU 2020112285 A RU2020112285 A RU 2020112285A RU 2020112285 A RU2020112285 A RU 2020112285A RU 2020112285 A RU2020112285 A RU 2020112285A RU 2020112285 A RU2020112285 A RU 2020112285A
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- compound represented
- following formula
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- fluoride
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- 150000001875 compounds Chemical class 0.000 title claims 41
- 239000000178 monomer Substances 0.000 title claims 11
- 238000000034 method Methods 0.000 title claims 5
- -1 fluorosulfonyl group Chemical group 0.000 claims 15
- 125000006551 perfluoro alkylene group Chemical group 0.000 claims 9
- 238000004519 manufacturing process Methods 0.000 claims 6
- 239000003795 chemical substances by application Substances 0.000 claims 4
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 claims 4
- 229910001512 metal fluoride Inorganic materials 0.000 claims 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 3
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims 3
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 3
- 238000005979 thermal decomposition reaction Methods 0.000 claims 3
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 claims 2
- HIGGFWFRAWSMBR-UHFFFAOYSA-N 2-Methyl-3-hexanone Chemical compound CCCC(=O)C(C)C HIGGFWFRAWSMBR-UHFFFAOYSA-N 0.000 claims 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 claims 2
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 claims 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- HYTRYEXINDDXJK-UHFFFAOYSA-N Ethyl isopropyl ketone Chemical compound CCC(=O)C(C)C HYTRYEXINDDXJK-UHFFFAOYSA-N 0.000 claims 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims 2
- 238000003682 fluorination reaction Methods 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims 2
- QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- CEBDXRXVGUQZJK-UHFFFAOYSA-N 2-methyl-1-benzofuran-7-carboxylic acid Chemical compound C1=CC(C(O)=O)=C2OC(C)=CC2=C1 CEBDXRXVGUQZJK-UHFFFAOYSA-N 0.000 claims 1
- 229910015900 BF3 Inorganic materials 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N N,N-Diethylethanamine Substances CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 1
- JJVGROTXXZVGGN-UHFFFAOYSA-H [Li+].[Li+].[Li+].[Li+].[Li+].[Li+].[F-].[F-].[F-].[F-].[F-].[F-] Chemical compound [Li+].[Li+].[Li+].[Li+].[Li+].[Li+].[F-].[F-].[F-].[F-].[F-].[F-] JJVGROTXXZVGGN-UHFFFAOYSA-H 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000012320 chlorinating reagent Substances 0.000 claims 1
- 239000012025 fluorinating agent Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 150000002222 fluorine compounds Chemical class 0.000 claims 1
- OXZOLXJZTSUDOM-UHFFFAOYSA-N fluoro 2,2,2-trifluoroacetate Chemical compound FOC(=O)C(F)(F)F OXZOLXJZTSUDOM-UHFFFAOYSA-N 0.000 claims 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims 1
- RLKHFSNWQCZBDC-UHFFFAOYSA-N n-(benzenesulfonyl)-n-fluorobenzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)N(F)S(=O)(=O)C1=CC=CC=C1 RLKHFSNWQCZBDC-UHFFFAOYSA-N 0.000 claims 1
- QKCGXXHCELUCKW-UHFFFAOYSA-N n-[4-[4-(dinaphthalen-2-ylamino)phenyl]phenyl]-n-naphthalen-2-ylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C=C4C=CC=CC4=CC=3)C=3C=C4C=CC=CC4=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=C21 QKCGXXHCELUCKW-UHFFFAOYSA-N 0.000 claims 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims 1
- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 claims 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims 1
- 235000003270 potassium fluoride Nutrition 0.000 claims 1
- 239000011698 potassium fluoride Substances 0.000 claims 1
- FWZMWMSAGOVWEZ-UHFFFAOYSA-N potassium;hydrofluoride Chemical compound F.[K] FWZMWMSAGOVWEZ-UHFFFAOYSA-N 0.000 claims 1
- ABTOQLMXBSRXSM-UHFFFAOYSA-N silicon tetrafluoride Chemical compound F[Si](F)(F)F ABTOQLMXBSRXSM-UHFFFAOYSA-N 0.000 claims 1
- 229940096017 silver fluoride Drugs 0.000 claims 1
- REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 claims 1
- 235000013024 sodium fluoride Nutrition 0.000 claims 1
- 239000011775 sodium fluoride Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims 1
- JOHWNGGYGAVMGU-UHFFFAOYSA-N trifluorochlorine Chemical compound FCl(F)F JOHWNGGYGAVMGU-UHFFFAOYSA-N 0.000 claims 1
- SMBZJSVIKJMSFP-UHFFFAOYSA-N trifluoromethyl hypofluorite Chemical compound FOC(F)(F)F SMBZJSVIKJMSFP-UHFFFAOYSA-N 0.000 claims 1
Classifications
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- B01D67/0093—Chemical modification
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- B01D71/36—Polytetrafluoroethene
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- B01D71/06—Organic material
- B01D71/76—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74
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- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
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- C07—ORGANIC CHEMISTRY
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- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
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Claims (37)
1. Способ получения соединения, содержащего фторсульфонильную группу, включающий в себя
реагирование соединения, представленного следующей формулой 1, выбранного из группы ацетона, метил этил кетона, диэтил кетона, метил пропил кетона, этил пропил кетона, дипропил кетона, диизопропил кетона, изопропил метил кетона, изопропил этил кетона или изопропил пропил кетона, с сульфонирующим агентом, выбранным из группы хлоросульфуриновой кислоты, флюоросульфоновой кислоты, триоксида серы, комплекса триоксида серы, дымящейся серной кислоты или концентрированной серной кислоты, для получения соединения, представленного следующей формулой 2,
реагирование соединения, представленного следующей формулой 2, с хлорирующим агентом, выбранным из группы тионил хлорида, фосфора пентахлорида, фосфора трихлорида, хлорида фосфорила, хлоросульфуриновая кислота, сульфурилхлорида или оксалилхлорида, для получения соединения, представленного следующей формулой 3,
реагирование соединения, представленного следующей формулой 3, с фторирующим агентом, выбранным из группы гидрофторида калия, гидрофторида натрия, фторида калия, фторида натрия, фторида цезия, фторида серебра, четырехзамещенного фторида аммония (например, фторида тетраэтиламмония или фторида тетрабутиламмония), фторида водорода, гидрофторной кислоты или комплекса фторида водорода, такого как комплекса HF-пирида или HF-триэтиламина), для получения соединения, представленного следующей формулой 4, и
воздействие на соединение, представленное следующей формулой 4, обработкой фторированием путем контактирования с газообразным фтором или соединением фтора, выбранным из группы фтористого водорода, трифторида хлора, пентафторида йода, трифторида бора, трифторида азота, пентафторида фосфора, тетрафторида кремния или гексафторида серы, фторида лития или фторида никеля (II), трифторметила гипофторита или трифторацетила гипофторита, агента реакции электрофильного фторирования, такого как N-фторбензолсульфонимид, для получения соединения, представленного следующей формулой 5
где R1 и R2 представляют собой C1-3 алкиленовую группу, а RF1 и RF2 представляют собой C1-3 перфторалкиленовую группу.
2. Способ получения мономера, содержащего фторсульфонильную группу, включающий в себя получение соединения, представленного формулой 5, способом получения соединения, содержащего фторсульфонильную группу, по п. 1, и реагирование соединения, представленного формулой 5, с перфтораллилирующим агентом, имеющим формулу CF2=CFCF2-G, где G представляет собой -OSO2F, -OSO2Rf2, атом хлора, атом брома или атом йода, и Rf2 представляет собой C1-8 перфторалкильную группу, для получения соединения, представленного следующей формулой 7
где RF1 и RF2 представляет собой C1-3 перфторлкиленовую группу.
3. Способ получения мономера, содержащего фторсульфонильную группу, включающий в себя получение соединения, представленного формулой 5, способом получения мономера, содержащего фторсульфонильную группу, по п. 1, добавление 2 молей гексафторпропиленоксида к 1 молю соединения, представленного формулой 5, в присутствии фторида металла для получения соединения, представленного следующей формулой 8a, и термическое разложение соединения, представленного следующей формулой 8a, для получения соединения, представленного следующей формулой 9а
где RF1 и RF2 представляют собой C1-3 перфторалкиленовую группу.
4. Способ получения мономера, содержащего фторсульфонильную группу, включающий в себя получение соединения, представленного формулой 5, способом получения соединения, содержащего фторсульфонильную группу, по п. 1, добавление 1 моля гексафторпропиленоксида к 1 молю соединения, представленного формулой 5, в присутствии фторида металла для получения соединения, представленного следующей формулой 8b, и термическое разложение соединения, представленного следующей формулой 8b, для получения соединения, представленного следующей формулой 10:
где RF1 и RF2 представляют собой C1-3 перфторалкиленовую группу.
5. Способ получения мономера, содержащего фторсульфонильную группу, включающий в себя взаимодействие соединения, представленного следующей формулой 5, с перфтораллилирующим агентом, имеющим формулу CF2=CFCF2-G, где G представляет собой -OSO2F, -OSO2Rf2, атом хлора, атом брома или атом йода, и Rf2 представляет собой C1-8 перфторалкильную группу, с получением соединения, представленного следующей формулой 7
где RF1 и RF2 представляют собой C1-3 перфторалкиленовую группу.
6. Способ получения мономера, содержащего фторсульфонильную группу, который включает добавление 2 молей гексафторпропиленоксида к 1 молю соединения, представленного следующей формулой 5, в присутствии фторида металла для получения соединения, представленного следующей формулой 8a, и термическое разложение соединения, представленного следующей формулой 8а, с получением соединения, представленного следующей формулой 9а
где RF1 и RF2 представляют собой C1-3 перфторалкиленовую группу.
7. Способ получения мономера, содержащего фторсульфонильную группу, который включает добавление 1 моля гексафторпропиленоксида к 1 молю соединения, представленного следующей формулой 5, в присутствии фторида металла с получением соединения, представленного следующей формулой 8b, и термическое разложение соединения, представленного следующей формулой 8b, с получением соединения, представленного следующей формулой 10
где RF1 и RF2 представляют собой C1-3 перфторалкиленовую группу.
8. Соединение, содержащее фторсульфонильную группу, которое представляет собой одно или оба из соединения, представленного следующей формулой 5, и соединения, представленного следующей формулой 5'
где RF1 и RF2 представляют собой CF2- группу.
9. Мономер, содержащий фторсульфонильную группу, который представляет собой соединение, представленное следующей формулой 7
где RF1 и RF2 представляют собой C1-3 перфторалкиленовую группу.
10. Мономер, содержащий фторсульфонильную группу, который представляет собой соединение, представленное следующей формулой 9а
где RF1 и RF2 представляют собой CF2- группу.
11. Мономер, содержащий фторсульфонильную группу, который представляет собой соединение, представленное следующей формулой 10:
где RF1 и RF2 представляют собой C1-3 перфторалкиленовую группу.
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EP3677570A4 (en) | 2021-06-16 |
US20220041765A1 (en) | 2022-02-10 |
RU2771278C2 (ru) | 2022-04-29 |
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JPWO2019045064A1 (ja) | 2020-10-29 |
EP3677571A4 (en) | 2021-06-30 |
EP3677570A1 (en) | 2020-07-08 |
EP3677570B1 (en) | 2023-11-08 |
RU2020112285A3 (ru) | 2021-10-04 |
CN111065624B (zh) | 2022-07-26 |
WO2019045064A1 (ja) | 2019-03-07 |
WO2019045063A1 (ja) | 2019-03-07 |
US20200190233A1 (en) | 2020-06-18 |
JP7173019B2 (ja) | 2022-11-16 |
CN111065624A (zh) | 2020-04-24 |
JP7056664B2 (ja) | 2022-04-19 |
RU2020112290A3 (ru) | 2021-10-01 |
JP2022044614A (ja) | 2022-03-17 |
KR102616339B1 (ko) | 2023-12-20 |
US11414502B2 (en) | 2022-08-16 |
RU2020112290A (ru) | 2021-10-01 |
JP2022169648A (ja) | 2022-11-09 |
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