CN113501842B - 三甲基硅烷基2-(氟磺酰基)二氟乙酸酯的制备方法 - Google Patents
三甲基硅烷基2-(氟磺酰基)二氟乙酸酯的制备方法 Download PDFInfo
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- CN113501842B CN113501842B CN202110940858.6A CN202110940858A CN113501842B CN 113501842 B CN113501842 B CN 113501842B CN 202110940858 A CN202110940858 A CN 202110940858A CN 113501842 B CN113501842 B CN 113501842B
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- Prior art keywords
- fluorosulfonyl
- difluoroacetate
- trimethylsilyl
- controlling
- pyridine
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- YMLAVJJQEPGJAP-UHFFFAOYSA-N 1-(bromomethyl)-2-phenylmethoxybenzene Chemical compound BrCC1=CC=CC=C1OCC1=CC=CC=C1 YMLAVJJQEPGJAP-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title abstract description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 45
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 36
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000010438 heat treatment Methods 0.000 claims abstract description 12
- 239000005051 trimethylchlorosilane Substances 0.000 claims abstract description 12
- VYDQUABHDFWIIX-UHFFFAOYSA-N 2,2-difluoro-2-fluorosulfonylacetic acid Chemical compound OC(=O)C(F)(F)S(F)(=O)=O VYDQUABHDFWIIX-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000000926 separation method Methods 0.000 claims abstract description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000007788 liquid Substances 0.000 claims abstract description 8
- 238000004321 preservation Methods 0.000 claims abstract description 8
- 238000010992 reflux Methods 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 238000010521 absorption reaction Methods 0.000 claims abstract description 3
- 239000007789 gas Substances 0.000 claims abstract description 3
- 238000004821 distillation Methods 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 7
- 238000001577 simple distillation Methods 0.000 claims description 3
- -1 trimethylsilyl 2- (fluorosulfonyl) difluoroacetate ester Chemical class 0.000 claims description 3
- 238000011534 incubation Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 8
- 235000017304 Ruaghas Nutrition 0.000 description 6
- 241000554738 Rusa Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical group ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
- 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 1
- IQOOSURRNAYCJV-UHFFFAOYSA-N 2,2-difluoro-2-fluorosulfonylacetyl chloride Chemical compound ClC(=O)C(F)(F)S(F)(=O)=O IQOOSURRNAYCJV-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005888 cyclopropanation reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1896—Compounds having one or more Si-O-acyl linkages
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
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CN202110940858.6A CN113501842B (zh) | 2021-08-17 | 2021-08-17 | 三甲基硅烷基2-(氟磺酰基)二氟乙酸酯的制备方法 |
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CN202110940858.6A CN113501842B (zh) | 2021-08-17 | 2021-08-17 | 三甲基硅烷基2-(氟磺酰基)二氟乙酸酯的制备方法 |
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CN113501842A CN113501842A (zh) | 2021-10-15 |
CN113501842B true CN113501842B (zh) | 2022-11-15 |
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Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1446803A (zh) * | 2002-03-22 | 2003-10-08 | 浙江工业大学 | 1-氯甲酰基-3-甲磺酰基-2-咪唑烷酮的化学合成方法 |
CN101648965A (zh) * | 2009-07-30 | 2010-02-17 | 杭州师范大学 | 一种双(n,n-二乙基)氨基甲基三氟丙基硅烷及其合成方法 |
CN101774923A (zh) * | 2010-01-26 | 2010-07-14 | 中化国际(苏州)新材料研发有限公司 | 一种氟代碳酸乙烯酯的制备方法 |
CN103467513A (zh) * | 2013-08-29 | 2013-12-25 | 深圳新宙邦科技股份有限公司 | 一种磷酸三烯丙酯的制备方法 |
CN103992285A (zh) * | 2014-06-03 | 2014-08-20 | 如皋市金陵化工有限公司 | 1-h苯并三氮唑乙酸酯的生产方法 |
CN107325024A (zh) * | 2017-08-11 | 2017-11-07 | 黄河三角洲京博化工研究院有限公司 | 一种苯二亚甲基二异氰酸酯的制备方法 |
CN110943250A (zh) * | 2018-09-21 | 2020-03-31 | 宁德新能源科技有限公司 | 电解液和含有电解液的锂离子电池 |
CN110964050A (zh) * | 2019-12-19 | 2020-04-07 | 仙桃市蓝化有机硅有限公司 | 一种甲基乙烯基二(n-乙基乙酰氨基)硅烷的制备方法 |
-
2021
- 2021-08-17 CN CN202110940858.6A patent/CN113501842B/zh active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1446803A (zh) * | 2002-03-22 | 2003-10-08 | 浙江工业大学 | 1-氯甲酰基-3-甲磺酰基-2-咪唑烷酮的化学合成方法 |
CN101648965A (zh) * | 2009-07-30 | 2010-02-17 | 杭州师范大学 | 一种双(n,n-二乙基)氨基甲基三氟丙基硅烷及其合成方法 |
CN101774923A (zh) * | 2010-01-26 | 2010-07-14 | 中化国际(苏州)新材料研发有限公司 | 一种氟代碳酸乙烯酯的制备方法 |
CN103467513A (zh) * | 2013-08-29 | 2013-12-25 | 深圳新宙邦科技股份有限公司 | 一种磷酸三烯丙酯的制备方法 |
CN103992285A (zh) * | 2014-06-03 | 2014-08-20 | 如皋市金陵化工有限公司 | 1-h苯并三氮唑乙酸酯的生产方法 |
CN107325024A (zh) * | 2017-08-11 | 2017-11-07 | 黄河三角洲京博化工研究院有限公司 | 一种苯二亚甲基二异氰酸酯的制备方法 |
CN110943250A (zh) * | 2018-09-21 | 2020-03-31 | 宁德新能源科技有限公司 | 电解液和含有电解液的锂离子电池 |
CN110964050A (zh) * | 2019-12-19 | 2020-04-07 | 仙桃市蓝化有机硅有限公司 | 一种甲基乙烯基二(n-乙基乙酰氨基)硅烷的制备方法 |
Non-Patent Citations (1)
Title |
---|
"Preparation and use of a new difluorocarbene reagent. trimethylsilyl 2-fluorosulfonyl-2,2-difluoroacetate: n-butyl 2,2-difluorocyclopropanecarboxylate";W. R. Dolbier 等;《Organic Syntheses》;20031230;第80卷;第172-173页 * |
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Address after: 050000 No. 1, Lingda Road, Douyu Industrial Zone, Luancheng District, Shijiazhuang, Hebei Applicant after: Hebei Shengtai Materials Co.,Ltd. Applicant after: HEBEI SONGCHEN PHARMACEUTICAL TECHNOLOGY CO.,LTD. Address before: 051430 douyu Industrial Zone, Shijiazhuang City, Hebei Province Applicant before: SHIJIAZHUANG SHENGTAI CHEMICAL Co.,Ltd. Applicant before: HEBEI SONGCHEN PHARMACEUTICAL TECHNOLOGY CO.,LTD. |
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Inventor after: Li Qingzhan Inventor after: Xing Yanzhao Inventor after: Liu Peng Inventor before: Li Qingzhan Inventor before: Xing Yanzhao Inventor before: Liu Peng Inventor before: Wu Hongsong |
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Effective date of registration: 20230327 Address after: 050000 No. 1, Lingda Road, Douyu Industrial Zone, Luancheng District, Shijiazhuang, Hebei Patentee after: Hebei Shengtai Materials Co.,Ltd. Address before: 050000 No. 1, Lingda Road, Douyu Industrial Zone, Luancheng District, Shijiazhuang, Hebei Patentee before: Hebei Shengtai Materials Co.,Ltd. Patentee before: HEBEI SONGCHEN PHARMACEUTICAL TECHNOLOGY CO.,LTD. |