SU722484A3 - Способ получени -метилнитрофталимидов - Google Patents
Способ получени -метилнитрофталимидов Download PDFInfo
- Publication number
- SU722484A3 SU722484A3 SU752127885A SU2127885A SU722484A3 SU 722484 A3 SU722484 A3 SU 722484A3 SU 752127885 A SU752127885 A SU 752127885A SU 2127885 A SU2127885 A SU 2127885A SU 722484 A3 SU722484 A3 SU 722484A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- sulfuric acid
- solution
- methylene chloride
- extraction
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract description 21
- FWIZOFDVGZCRTB-UHFFFAOYSA-N 2-methyl-4-nitroisoindole-1,3-dione Chemical class C1=CC([N+]([O-])=O)=C2C(=O)N(C)C(=O)C2=C1 FWIZOFDVGZCRTB-UHFFFAOYSA-N 0.000 title abstract description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 67
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 60
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract description 13
- 229910017604 nitric acid Inorganic materials 0.000 abstract description 13
- ZXLYYQUMYFHCLQ-UHFFFAOYSA-N 2-methylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(C)C(=O)C2=C1 ZXLYYQUMYFHCLQ-UHFFFAOYSA-N 0.000 abstract description 12
- 239000000203 mixture Substances 0.000 abstract description 3
- JBCHWGTZAAZJKG-UHFFFAOYSA-N 2-methyl-5-nitroisoindole-1,3-dione Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(C)C(=O)C2=C1 JBCHWGTZAAZJKG-UHFFFAOYSA-N 0.000 abstract description 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- ANYWGXDASKQYAD-UHFFFAOYSA-N 5-nitroisoindole-1,3-dione Chemical class [O-][N+](=O)C1=CC=C2C(=O)NC(=O)C2=C1 ANYWGXDASKQYAD-UHFFFAOYSA-N 0.000 abstract 1
- 238000000605 extraction Methods 0.000 description 22
- 239000000243 solution Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000006396 nitration reaction Methods 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 3
- ABCGRFHYOYXEJV-UHFFFAOYSA-N 4-methylisoindole-1,3-dione Chemical compound CC1=CC=CC2=C1C(=O)NC2=O ABCGRFHYOYXEJV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- KIYCGQOKSPJGDG-UHFFFAOYSA-N 2-methylisoindole-1,3-dione;nitric acid Chemical compound O[N+]([O-])=O.C1=CC=C2C(=O)N(C)C(=O)C2=C1 KIYCGQOKSPJGDG-UHFFFAOYSA-N 0.000 description 1
- JKLDLZVPEFRPLS-UHFFFAOYSA-N 2-nitroisoindole-1,3-dione Chemical class C1=CC=C2C(=O)N([N+](=O)[O-])C(=O)C2=C1 JKLDLZVPEFRPLS-UHFFFAOYSA-N 0.000 description 1
- ROFZMKDROVBLNY-UHFFFAOYSA-N 4-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC2=C1C(=O)OC2=O ROFZMKDROVBLNY-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/468,012 US3933852A (en) | 1974-05-08 | 1974-05-08 | Process for making N-methyl nitrophthalimides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU722484A3 true SU722484A3 (ru) | 1980-03-15 |
Family
ID=23858068
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752127885A SU722484A3 (ru) | 1974-05-08 | 1975-04-25 | Способ получени -метилнитрофталимидов |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3933852A (enExample) |
| JP (1) | JPS5953257B2 (enExample) |
| BR (1) | BR7502773A (enExample) |
| DD (1) | DD119786A5 (enExample) |
| DE (1) | DE2509949C2 (enExample) |
| FR (1) | FR2270247B1 (enExample) |
| GB (1) | GB1510735A (enExample) |
| IT (1) | IT1037923B (enExample) |
| NL (1) | NL7505437A (enExample) |
| SU (1) | SU722484A3 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4005102A (en) * | 1974-07-08 | 1977-01-25 | General Electric Company | Process for making 4-nitro-n-methylphthalimide |
| US4017511A (en) * | 1976-03-24 | 1977-04-12 | General Electric Company | Preparation of aromatic bisimides |
| US4116980A (en) * | 1976-10-04 | 1978-09-26 | General Electric Company | Method for making aromatic bis (ether phthalic acid) or aromatic bis (ether anhydride)s |
| US4217281A (en) * | 1976-10-04 | 1980-08-12 | General Electric Company | Imide carbonyl compounds and method for making |
| US4599429A (en) * | 1983-12-08 | 1986-07-08 | General Electric Company | Destruction of DNPI in an all nitric acid nitration process |
| DE3479211D1 (en) * | 1983-12-08 | 1989-09-07 | Gen Electric | Method for making n-substituted nitrophthalimides |
| US4902809A (en) * | 1983-12-08 | 1990-02-20 | General Electric Company | Method for making N-substituted nitrophthalimides |
| EP0165300B1 (en) * | 1983-12-08 | 1988-11-09 | General Electric Company | Nitration of phthalic acid and phthalic anhydride using nitric acid |
| US4921970A (en) * | 1984-01-03 | 1990-05-01 | General Electric Company | Nitration reactions with acid anhydride promoters |
| US4757149A (en) * | 1986-12-31 | 1988-07-12 | General Electric Company | Synthesis of bis(N-substituted phthalimide)ethers |
| US5068353A (en) * | 1986-12-31 | 1991-11-26 | General Electric Company | Synthesis of aromatic bis(ether phthalimide) compounds |
| US6008374A (en) * | 1994-05-27 | 1999-12-28 | General Electric Company | Process for preparing bis (ether anhydrides) using alkylamine derived bisimides having low melting temperatures |
| US20060029671A1 (en) * | 2004-08-06 | 2006-02-09 | Grain Processing Corporation | Tablet coating composition |
| US8080671B2 (en) | 2008-05-23 | 2011-12-20 | Sabic Innovative Plastics Ip B.V. | Production of low color polyetherimides |
| WO2017117449A1 (en) * | 2015-12-29 | 2017-07-06 | Sabic Global Technologies B.V. | Methods for the manufacture of an aromatic bisimide and a polyetherimide |
| WO2020131258A1 (en) | 2018-12-21 | 2020-06-25 | Sabic Global Technologies B.V. | Method for the manufacture of 4-nitro-n-(c1-8 alkyl)phthalimide |
-
1974
- 1974-05-08 US US05/468,012 patent/US3933852A/en not_active Expired - Lifetime
-
1975
- 1975-03-07 DE DE2509949A patent/DE2509949C2/de not_active Expired
- 1975-04-23 GB GB16788/75A patent/GB1510735A/en not_active Expired
- 1975-04-25 SU SU752127885A patent/SU722484A3/ru active
- 1975-05-06 DD DD185865A patent/DD119786A5/xx unknown
- 1975-05-07 BR BR3536/75D patent/BR7502773A/pt unknown
- 1975-05-07 JP JP50053944A patent/JPS5953257B2/ja not_active Expired
- 1975-05-07 NL NL7505437A patent/NL7505437A/xx not_active Application Discontinuation
- 1975-05-07 IT IT23096/75A patent/IT1037923B/it active
- 1975-05-07 FR FR7514301A patent/FR2270247B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2509949C2 (de) | 1983-06-23 |
| GB1510735A (en) | 1978-05-17 |
| NL7505437A (nl) | 1975-11-11 |
| BR7502773A (pt) | 1976-03-16 |
| FR2270247A1 (enExample) | 1975-12-05 |
| DE2509949A1 (de) | 1975-11-27 |
| JPS5953257B2 (ja) | 1984-12-24 |
| DD119786A5 (enExample) | 1976-05-12 |
| FR2270247B1 (enExample) | 1979-06-08 |
| AU7914775A (en) | 1976-09-23 |
| US3933852A (en) | 1976-01-20 |
| IT1037923B (it) | 1979-11-20 |
| JPS50151871A (enExample) | 1975-12-06 |
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