BR112017013246B1 - Processo para produzir anidrido 4-azidossulfonilftálico - Google Patents
Processo para produzir anidrido 4-azidossulfonilftálico Download PDFInfo
- Publication number
- BR112017013246B1 BR112017013246B1 BR112017013246-0A BR112017013246A BR112017013246B1 BR 112017013246 B1 BR112017013246 B1 BR 112017013246B1 BR 112017013246 A BR112017013246 A BR 112017013246A BR 112017013246 B1 BR112017013246 B1 BR 112017013246B1
- Authority
- BR
- Brazil
- Prior art keywords
- anhydride
- isolated
- chlorosulfonylphthalic
- dissolved
- solvent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 58
- 150000008064 anhydrides Chemical class 0.000 title claims 2
- 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 abstract description 69
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 62
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims abstract description 54
- 238000006243 chemical reaction Methods 0.000 claims abstract description 39
- 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 abstract description 39
- 239000011780 sodium chloride Substances 0.000 claims abstract description 31
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 239000007787 solid Substances 0.000 claims abstract description 15
- 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 abstract description 15
- WNKQDGLSQUASME-UHFFFAOYSA-N 4-sulfophthalic acid Chemical compound OC(=O)C1=CC=C(S(O)(=O)=O)C=C1C(O)=O WNKQDGLSQUASME-UHFFFAOYSA-N 0.000 claims abstract description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 70
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 238000005660 chlorination reaction Methods 0.000 claims description 14
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 10
- 239000008346 aqueous phase Substances 0.000 claims description 8
- 239000012320 chlorinating reagent Substances 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- 239000007791 liquid phase Substances 0.000 claims description 5
- -1 4-chlorosulfonyl anhydride Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 23
- 229920000642 polymer Polymers 0.000 description 15
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 14
- 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 description 14
- 238000004519 manufacturing process Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 239000000178 monomer Substances 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 7
- 239000004810 polytetrafluoroethylene Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000002390 rotary evaporation Methods 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- 239000004809 Teflon Substances 0.000 description 4
- 229920006362 Teflon® Polymers 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- HWEXKRHYVOGVDA-UHFFFAOYSA-M sodium;3-trimethylsilylpropane-1-sulfonate Chemical compound [Na+].C[Si](C)(C)CCCS([O-])(=O)=O HWEXKRHYVOGVDA-UHFFFAOYSA-M 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000013529 heat transfer fluid Substances 0.000 description 3
- 230000010354 integration Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000003828 vacuum filtration Methods 0.000 description 3
- 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 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- NVRBTKMAZQNKPX-UHFFFAOYSA-N trimethyl-(4-trimethylsilylphenyl)silane Chemical compound C[Si](C)(C)C1=CC=C([Si](C)(C)C)C=C1 NVRBTKMAZQNKPX-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- HTVPMHKGNPIQBO-UHFFFAOYSA-N S(=O)(=O)(O)C=1C=C(C(C(=O)O)=CC1)C(=O)O.[Na].[Na].[Na] Chemical compound S(=O)(=O)(O)C=1C=C(C(C(=O)O)=CC1)C(=O)O.[Na].[Na].[Na] HTVPMHKGNPIQBO-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- WZKJANWNNBJHRS-UBEDBUPSSA-N n-[9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-oxo-3h-purin-2-yl]benzamide Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(NC(NC(=O)C=2C=CC=CC=2)=NC2=O)=C2N=C1 WZKJANWNNBJHRS-UBEDBUPSSA-N 0.000 description 1
- VKXKHWFBLWKDKB-UHFFFAOYSA-N n-diazo-1,3-dioxo-2-benzofuran-4-sulfonamide Chemical compound [N-]=[N+]=NS(=O)(=O)C1=CC=CC2=C1C(=O)OC2=O VKXKHWFBLWKDKB-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229920006029 tetra-polymer Polymers 0.000 description 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/89—Benzo [c] furans; Hydrogenated benzo [c] furans with two oxygen atoms directly attached in positions 1 and 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
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 (2)
| Publication Number | Publication Date |
|---|---|
| BR112017013246A2 BR112017013246A2 (pt) | 2018-02-27 |
| BR112017013246B1 true BR112017013246B1 (pt) | 2021-09-14 |
Family
ID=55300758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112017013246-0A BR112017013246B1 (pt) | 2014-12-30 | 2015-12-28 | Processo para produzir anidrido 4-azidossulfonilftálico |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10005751B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3240782B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6657219B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN107001308B (cg-RX-API-DMAC7.html) |
| AR (1) | AR103071A1 (cg-RX-API-DMAC7.html) |
| BR (1) | BR112017013246B1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2719139T3 (cg-RX-API-DMAC7.html) |
| MX (1) | MX2017007376A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2016109389A1 (cg-RX-API-DMAC7.html) |
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 |
| WO2007034558A1 (ja) * | 2005-09-26 | 2007-03-29 | Manac Inc. | 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 BR BR112017013246-0A patent/BR112017013246B1/pt active IP Right Grant
- 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 ES ES15831254T patent/ES2719139T3/es active Active
- 2015-12-28 US US15/541,207 patent/US10005751B2/en active Active
- 2015-12-28 MX MX2017007376A patent/MX2017007376A/es unknown
- 2015-12-28 CN CN201580069156.8A patent/CN107001308B/zh active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP6657219B2 (ja) | 2020-03-04 |
| CN107001308A (zh) | 2017-08-01 |
| AR103071A1 (es) | 2017-04-12 |
| MX2017007376A (es) | 2017-11-06 |
| CN107001308B (zh) | 2020-09-25 |
| US10005751B2 (en) | 2018-06-26 |
| EP3240782B1 (en) | 2019-01-30 |
| US20170369464A1 (en) | 2017-12-28 |
| ES2719139T3 (es) | 2019-07-08 |
| EP3240782A1 (en) | 2017-11-08 |
| JP2018504374A (ja) | 2018-02-15 |
| BR112017013246A2 (pt) | 2018-02-27 |
| WO2016109389A1 (en) | 2016-07-07 |
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