DE1770840C3 - Verfahren zur Herstellung von Pyromellitsäurediimid - Google Patents
Verfahren zur Herstellung von PyromellitsäurediimidInfo
- Publication number
- DE1770840C3 DE1770840C3 DE1770840A DE1770840A DE1770840C3 DE 1770840 C3 DE1770840 C3 DE 1770840C3 DE 1770840 A DE1770840 A DE 1770840A DE 1770840 A DE1770840 A DE 1770840A DE 1770840 C3 DE1770840 C3 DE 1770840C3
- Authority
- DE
- Germany
- Prior art keywords
- formamide
- pyromellitic
- pyromellitic acid
- acid
- diimide
- 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
- UGQZLDXDWSPAOM-UHFFFAOYSA-N pyrrolo[3,4-f]isoindole-1,3,5,7-tetrone Chemical compound C1=C2C(=O)NC(=O)C2=CC2=C1C(=O)NC2=O UGQZLDXDWSPAOM-UHFFFAOYSA-N 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 5
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 60
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 37
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 12
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000013459 approach Methods 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 239000012452 mother liquor Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 5
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 5
- 229910000071 diazene Inorganic materials 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 2
- VUTICWRXMKBOSF-UHFFFAOYSA-N 2,5-dibromoterephthalic acid Chemical compound OC(=O)C1=CC(Br)=C(C(O)=O)C=C1Br VUTICWRXMKBOSF-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VBGLAHNCYJVFHL-UHFFFAOYSA-N 4,6-dicarbamoylbenzene-1,3-dicarboxylic acid Chemical compound OC(=N)C1=CC(C(O)=N)=C(C(O)=O)C=C1C(O)=O VBGLAHNCYJVFHL-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- YNPFMWCWRVTGKJ-UHFFFAOYSA-N mianserin hydrochloride Chemical compound [H+].[Cl-].C1C2=CC=CC=C2N2CCN(C)CC2C2=CC=CC=C21 YNPFMWCWRVTGKJ-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- UGJCNRLBGKEGEH-UHFFFAOYSA-N sodium-binding benzofuran isophthalate Chemical compound COC1=CC=2C=C(C=3C(=CC(=CC=3)C(O)=O)C(O)=O)OC=2C=C1N(CCOCC1)CCOCCOCCN1C(C(=CC=1C=2)OC)=CC=1OC=2C1=CC=C(C(O)=O)C=C1C(O)=O UGJCNRLBGKEGEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1770840A DE1770840C3 (de) | 1968-07-10 | 1968-07-10 | Verfahren zur Herstellung von Pyromellitsäurediimid |
| US837946A US3697541A (en) | 1968-07-10 | 1969-06-30 | Process for the manufacture of pyromellitic acid diimide |
| JP5419269A JPS5323320B1 (enExample) | 1968-07-10 | 1969-07-10 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1770840A DE1770840C3 (de) | 1968-07-10 | 1968-07-10 | Verfahren zur Herstellung von Pyromellitsäurediimid |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1770840A1 DE1770840A1 (de) | 1972-01-13 |
| DE1770840B2 DE1770840B2 (de) | 1978-03-23 |
| DE1770840C3 true DE1770840C3 (de) | 1978-11-23 |
Family
ID=5700662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1770840A Expired DE1770840C3 (de) | 1968-07-10 | 1968-07-10 | Verfahren zur Herstellung von Pyromellitsäurediimid |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3697541A (enExample) |
| JP (1) | JPS5323320B1 (enExample) |
| DE (1) | DE1770840C3 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ191821A (en) * | 1978-10-23 | 1982-08-17 | Merck & Co Inc | Pyromellitic diimides and feed efficiency increasing compositions for ruminants |
| JPS63101319U (enExample) * | 1986-08-20 | 1988-07-01 | ||
| KR102599207B1 (ko) | 2018-07-20 | 2023-12-15 | 삼성전자 주식회사 | 전자 디바이스의 표면 측정 장치 및 방법 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3078228A (en) * | 1959-11-06 | 1963-02-19 | Houghton & Co E F | Imide compounds and lubricants containing the same |
-
1968
- 1968-07-10 DE DE1770840A patent/DE1770840C3/de not_active Expired
-
1969
- 1969-06-30 US US837946A patent/US3697541A/en not_active Expired - Lifetime
- 1969-07-10 JP JP5419269A patent/JPS5323320B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE1770840B2 (de) | 1978-03-23 |
| US3697541A (en) | 1972-10-10 |
| DE1770840A1 (de) | 1972-01-13 |
| JPS5323320B1 (enExample) | 1978-07-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |