JPS5953258B2 - ４−ニトロ−ｎ−メチルフタルイミドの製法 - Google Patents
４−ニトロ−ｎ−メチルフタルイミドの製法Info
- Publication number
- JPS5953258B2 JPS5953258B2 JP50082833A JP8283375A JPS5953258B2 JP S5953258 B2 JPS5953258 B2 JP S5953258B2 JP 50082833 A JP50082833 A JP 50082833A JP 8283375 A JP8283375 A JP 8283375A JP S5953258 B2 JPS5953258 B2 JP S5953258B2
- Authority
- JP
- Japan
- Prior art keywords
- methylene chloride
- methylphthalimide
- nitrification
- nitro
- reaction
- 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.)
- Expired
Links
- 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 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 110
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 10
- 229910017604 nitric acid Inorganic materials 0.000 claims description 10
- 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 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- FWIZOFDVGZCRTB-UHFFFAOYSA-N 2-methyl-4-nitroisoindole-1,3-dione Chemical compound C1=CC([N+]([O-])=O)=C2C(=O)N(C)C(=O)C2=C1 FWIZOFDVGZCRTB-UHFFFAOYSA-N 0.000 claims 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 10
- 238000000605 extraction Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 7
- 150000001491 aromatic compounds Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- 231100001261 hazardous Toxicity 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001441723 Takifugu Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B43/00—Formation or introduction of functional groups containing nitrogen
- C07B43/02—Formation or introduction of functional groups containing nitrogen of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48635674A | 1974-07-08 | 1974-07-08 | |
| US486356 | 1974-07-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5129450A JPS5129450A (xx) | 1976-03-12 |
| JPS5953258B2 true JPS5953258B2 (ja) | 1984-12-24 |
Family
ID=23931564
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50082833A Expired JPS5953258B2 (ja) | 1974-07-08 | 1975-07-07 | ４−ニトロ−ｎ−メチルフタルイミドの製法 |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5953258B2 (xx) |
| BR (1) | BR7504323A (xx) |
| CA (1) | CA1066295A (xx) |
| DD (1) | DD119206A5 (xx) |
| DE (1) | DE2522818C2 (xx) |
| DK (1) | DK309275A (xx) |
| FR (1) | FR2277797A1 (xx) |
| GB (1) | GB1511345A (xx) |
| IT (1) | IT1039626B (xx) |
| NL (1) | NL7508085A (xx) |
| SE (1) | SE427032B (xx) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS552546B2 (xx) * | 1971-11-24 | 1980-01-21 | ||
| US4339618A (en) * | 1979-06-21 | 1982-07-13 | Ciba-Geigy Ag | Process for the production of substituted nitroaryl compounds |
| US6935577B2 (en) | 2003-02-28 | 2005-08-30 | Illinois Tool Works Inc. | One-piece fluid nozzle |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3100797A (en) * | 1958-01-23 | 1963-08-13 | Dow Chemical Co | Production and crystallization of 3,5-dinitro-o-toluic acid from nitric and sulfuric acid |
-
1975
- 1975-05-20 GB GB21479/75A patent/GB1511345A/en not_active Expired
- 1975-05-23 DE DE2522818A patent/DE2522818C2/de not_active Expired
- 1975-05-23 CA CA227,680A patent/CA1066295A/en not_active Expired
- 1975-07-04 DD DD187108A patent/DD119206A5/xx unknown
- 1975-07-04 IT IT25086/75A patent/IT1039626B/it active
- 1975-07-07 JP JP50082833A patent/JPS5953258B2/ja not_active Expired
- 1975-07-07 NL NL7508085A patent/NL7508085A/xx not_active Application Discontinuation
- 1975-07-08 SE SE7507839A patent/SE427032B/xx unknown
- 1975-07-08 DK DK309275A patent/DK309275A/da not_active Application Discontinuation
- 1975-07-08 BR BR7504323*A patent/BR7504323A/pt unknown
- 1975-07-08 FR FR7521329A patent/FR2277797A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DK309275A (da) | 1976-01-09 |
| DE2522818A1 (de) | 1976-01-29 |
| SE427032B (sv) | 1983-02-28 |
| AU8141975A (en) | 1976-11-25 |
| DD119206A5 (xx) | 1976-04-12 |
| CA1066295A (en) | 1979-11-13 |
| BR7504323A (pt) | 1976-07-06 |
| FR2277797B1 (xx) | 1979-10-19 |
| GB1511345A (en) | 1978-05-17 |
| NL7508085A (nl) | 1976-01-12 |
| DE2522818C2 (de) | 1985-05-09 |
| JPS5129450A (xx) | 1976-03-12 |
| SE7507839L (sv) | 1976-01-09 |
| IT1039626B (it) | 1979-12-10 |
| FR2277797A1 (fr) | 1976-02-06 |
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