JP2018504374A5 - - Google Patents
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- Publication number
- JP2018504374A5 JP2018504374A5 JP2017530653A JP2017530653A JP2018504374A5 JP 2018504374 A5 JP2018504374 A5 JP 2018504374A5 JP 2017530653 A JP2017530653 A JP 2017530653A JP 2017530653 A JP2017530653 A JP 2017530653A JP 2018504374 A5 JP2018504374 A5 JP 2018504374A5
- Authority
- JP
- Japan
- Prior art keywords
- anhydride
- dissolved
- isolated
- chlorosulfonylphthalic
- sodium chloride
- 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 43
- PVSMAAZGXZNOCG-UHFFFAOYSA-N n-diazo-1,3-dioxo-2-benzofuran-5-sulfonamide Chemical compound [N-]=[N+]=NS(=O)(=O)C1=CC=C2C(=O)OC(=O)C2=C1 PVSMAAZGXZNOCG-UHFFFAOYSA-N 0.000 claims description 36
- VDBLRYZZFGJCLY-UHFFFAOYSA-N 1,3-dioxo-2-benzofuran-5-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C2C(=O)OC(=O)C2=C1 VDBLRYZZFGJCLY-UHFFFAOYSA-N 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 29
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 28
- 239000011780 sodium chloride Substances 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000007787 solid Substances 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 10
- 239000008346 aqueous phase Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 6
- IWFDIIDATFUMQH-UHFFFAOYSA-K trisodium;4-sulfonatophthalate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=CC=C(S([O-])(=O)=O)C=C1C([O-])=O IWFDIIDATFUMQH-UHFFFAOYSA-K 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- 238000005660 chlorination reaction Methods 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- -1 4-chlorosulfonyl anhydride Chemical class 0.000 claims description 2
- 239000012320 chlorinating reagent Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 3
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 6
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- CWPXQHTWOUWBKJ-UHFFFAOYSA-N 1,3-dioxo-2-benzofuran-4-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=C2C(C(=O)OC2=O)=CC=C1 CWPXQHTWOUWBKJ-UHFFFAOYSA-N 0.000 description 1
- YBSZPTGGIBVAKD-UHFFFAOYSA-N 4-azidosulfonylphthalic acid Chemical compound OC(=O)C1=CC=C(S(=O)(=O)N=[N+]=[N-])C=C1C(O)=O YBSZPTGGIBVAKD-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462097786P | 2014-12-30 | 2014-12-30 | |
| US62/097,786 | 2014-12-30 | ||
| PCT/US2015/067597 WO2016109389A1 (en) | 2014-12-30 | 2015-12-28 | Process for producing 4-azidosulfonylphthalic anhydride |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018504374A JP2018504374A (ja) | 2018-02-15 |
| JP2018504374A5 true JP2018504374A5 (OSRAM) | 2020-02-06 |
| JP6657219B2 JP6657219B2 (ja) | 2020-03-04 |
Family
ID=55300758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017530653A Active JP6657219B2 (ja) | 2014-12-30 | 2015-12-28 | ４−アジドスルホニルフタル酸無水物を生産する方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10005751B2 (OSRAM) |
| EP (1) | EP3240782B1 (OSRAM) |
| JP (1) | JP6657219B2 (OSRAM) |
| CN (1) | CN107001308B (OSRAM) |
| AR (1) | AR103071A1 (OSRAM) |
| BR (1) | BR112017013246B1 (OSRAM) |
| ES (1) | ES2719139T3 (OSRAM) |
| MX (1) | MX2017007376A (OSRAM) |
| WO (1) | WO2016109389A1 (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6789617B2 (ja) * | 2015-06-25 | 2020-11-25 | キヤノン株式会社 | カルボン酸無水物の製造方法、カルボン酸イミドの製造方法および電子写真感光体の製造方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3701788A (en) * | 1971-05-10 | 1972-10-31 | Upjohn Co | 4-azidosulfonylphthalic anhydride |
| EP0160218B1 (en) | 1984-04-02 | 1987-10-21 | Merck & Co. Inc. | Process for preparing c8 -c24 alkylbenzene sulfonylazides |
| US4772733A (en) * | 1986-07-17 | 1988-09-20 | Hercules Incorporated | Epoxy-azides |
| CN1228336C (zh) * | 2003-09-25 | 2005-11-23 | 华东师范大学 | 一种4－氯代苯酐的制备方法 |
| JP4500983B2 (ja) * | 2003-12-22 | 2010-07-14 | 東洋紡績株式会社 | ６−アルコキシ−２−ナフタレンチオールおよびその製造方法 |
| JP4871287B2 (ja) * | 2005-09-26 | 2012-02-08 | マナック株式会社 | 無水３−ヒドロキシフタル酸の製造方法 |
| JP5694109B2 (ja) * | 2011-09-26 | 2015-04-01 | 株式会社東芝 | パターン形成方法 |
| JP5795519B2 (ja) * | 2011-11-01 | 2015-10-14 | 住友精化株式会社 | クロロスルホニルベンゾイルクロライド化合物の製造方法 |
| EP2813249A1 (en) * | 2013-06-14 | 2014-12-17 | Biowintech | Implantable material grafted with a cell antiproliferative and/or antibacterial film synthetized from a bifunctional molecule |
| CN103641806A (zh) * | 2013-11-19 | 2014-03-19 | 常州市天华制药有限公司 | 一种4-苯乙炔苯酐的制备方法 |
-
2015
- 2015-12-17 AR ARP150104145A patent/AR103071A1/es active IP Right Grant
- 2015-12-28 JP JP2017530653A patent/JP6657219B2/ja active Active
- 2015-12-28 ES ES15831254T patent/ES2719139T3/es active Active
- 2015-12-28 MX MX2017007376A patent/MX2017007376A/es unknown
- 2015-12-28 EP EP15831254.6A patent/EP3240782B1/en active Active
- 2015-12-28 WO PCT/US2015/067597 patent/WO2016109389A1/en not_active Ceased
- 2015-12-28 CN CN201580069156.8A patent/CN107001308B/zh active Active
- 2015-12-28 BR BR112017013246-0A patent/BR112017013246B1/pt active IP Right Grant
- 2015-12-28 US US15/541,207 patent/US10005751B2/en active Active
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