HU192035B - Process for production of ftalimid and tetrahydroftalimid - Google Patents
Process for production of ftalimid and tetrahydroftalimid Download PDFInfo
- Publication number
- HU192035B HU192035B HU842328A HU232884A HU192035B HU 192035 B HU192035 B HU 192035B HU 842328 A HU842328 A HU 842328A HU 232884 A HU232884 A HU 232884A HU 192035 B HU192035 B HU 192035B
- Authority
- HU
- Hungary
- Prior art keywords
- urea
- anhydride
- reaction
- added
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000004202 carbamide Substances 0.000 claims abstract description 33
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000011541 reaction mixture Substances 0.000 claims abstract description 7
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 14
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 14
- CIFFBTOJCKSRJY-UHFFFAOYSA-N 3α,4,7,7α-tetrahydro-1h-isoindole-1,3(2h)-dione Chemical compound C1C=CCC2C(=O)NC(=O)C21 CIFFBTOJCKSRJY-UHFFFAOYSA-N 0.000 claims description 7
- -1 phthalic acid imide Chemical class 0.000 claims description 7
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 claims description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 5
- 230000000630 rising effect Effects 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 19
- 239000002904 solvent Substances 0.000 abstract description 11
- 125000004122 cyclic group Chemical group 0.000 abstract description 4
- 239000007789 gas Substances 0.000 abstract description 4
- 230000002378 acidificating effect Effects 0.000 abstract description 3
- 230000008929 regeneration Effects 0.000 abstract description 2
- 238000011069 regeneration method Methods 0.000 abstract description 2
- 238000003912 environmental pollution Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 150000008064 anhydrides Chemical class 0.000 description 5
- 239000012467 final product Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000003972 cyclic carboxylic anhydrides Chemical class 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000002912 waste gas Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 1
- 238000010936 aqueous wash Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000003736 gastrointestinal content Anatomy 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003860 storage Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pyrrole Compounds (AREA)
Abstract
Die Erfindung betrifft ein Verfahren zur Herstellung von cyclischen Dicarbonsaeureimiden durch Umsetzung von cyclischen Dicarbonsaeureanhydriden und Harnstoff ohne Loesungsmittel und ohne den Einsatz von Harnstoff in Ueberschuss. Ziel und Aufgabe der Erfindung ist es, die Reinheit und die Ausbeute bei derartigen Verfahren zu erhoehen und Umweltbelastungen erheblich zu verringern. Erfindungsgemaess wird die gestellte Aufgabe dadurch geloest, dass man in das geschmolzene Dicarbonsaeureanhydrid den Harnstoff stufenweise einfuehrt, wobei das Reaktionsgemisch staendig sauer gehalten wird und man die waehrend der Reaktion entstehenden substituierenden Gase und Daempfe aufnimmt und nach ihrer Regenerierung in das Reaktionsgemisch zurueckfuehrt.
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU842328A HU192035B (en) | 1984-06-18 | 1984-06-18 | Process for production of ftalimid and tetrahydroftalimid |
| IL75199A IL75199A0 (en) | 1984-06-18 | 1985-05-15 | Preparation of cyclic dicarboxylic acid imides |
| DE19853518619 DE3518619A1 (de) | 1984-06-18 | 1985-05-23 | Verfahren zur herstellung von cyclischen dicarbonsaeureimiden |
| FR8508037A FR2565975B1 (fr) | 1984-06-18 | 1985-05-29 | Procede de preparation d'imides d'acide dicarboxylique cyclique |
| DD85277208A DD234002A5 (de) | 1984-06-18 | 1985-06-10 | Verfahren zur herstellung von cyclischen dicarbonsaeure-imiden |
| YU00990/85A YU99085A (en) | 1984-06-18 | 1985-06-13 | Process for preaparation of cyclical imida dicarbonic acids |
| SU853909600A SU1355124A3 (ru) | 1984-06-18 | 1985-06-17 | Способ получени фталимида или тетрагидрофталимида |
| RO119176A RO92318B (ro) | 1984-06-18 | 1985-06-17 | Procedeu pentru prepararea de imide ciclice de acizi dicarboxilici |
| BG070701A BG43864A3 (en) | 1984-06-18 | 1985-06-17 | Method for preparing of imides of cyclic dicarbonic acids |
| JP60130066A JPS6112661A (ja) | 1984-06-18 | 1985-06-17 | 環状ジカルボン酸イミドの調製方法 |
| CS854451A CS250691B2 (en) | 1984-06-18 | 1985-06-18 | Method of dicarboxyl acids' cyclic imides production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU842328A HU192035B (en) | 1984-06-18 | 1984-06-18 | Process for production of ftalimid and tetrahydroftalimid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU192035B true HU192035B (en) | 1987-04-28 |
Family
ID=10958856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU842328A HU192035B (en) | 1984-06-18 | 1984-06-18 | Process for production of ftalimid and tetrahydroftalimid |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS6112661A (de) |
| BG (1) | BG43864A3 (de) |
| CS (1) | CS250691B2 (de) |
| DD (1) | DD234002A5 (de) |
| DE (1) | DE3518619A1 (de) |
| FR (1) | FR2565975B1 (de) |
| HU (1) | HU192035B (de) |
| IL (1) | IL75199A0 (de) |
| RO (1) | RO92318B (de) |
| SU (1) | SU1355124A3 (de) |
| YU (1) | YU99085A (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110804011A (zh) * | 2019-11-12 | 2020-02-18 | 内蒙古科迈化工有限公司 | 一种邻苯二甲酰亚胺合成方法 |
| CN111454196A (zh) * | 2020-05-12 | 2020-07-28 | 河南源博新材料有限公司 | 一种顺式-1,2,3,6-四氢邻苯二甲酰亚胺的生产合成方法 |
| CN115353481B (zh) * | 2022-08-31 | 2024-03-29 | 宁夏格瑞精细化工有限公司 | 一种顺式-1,2,3,6-四氢邻苯二甲酰亚胺的催化合成方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3819648A (en) * | 1971-11-12 | 1974-06-25 | Dawe Labor Inc S | Production of phthalimide |
-
1984
- 1984-06-18 HU HU842328A patent/HU192035B/hu not_active IP Right Cessation
-
1985
- 1985-05-15 IL IL75199A patent/IL75199A0/xx unknown
- 1985-05-23 DE DE19853518619 patent/DE3518619A1/de not_active Withdrawn
- 1985-05-29 FR FR8508037A patent/FR2565975B1/fr not_active Expired
- 1985-06-10 DD DD85277208A patent/DD234002A5/de not_active IP Right Cessation
- 1985-06-13 YU YU00990/85A patent/YU99085A/xx unknown
- 1985-06-17 RO RO119176A patent/RO92318B/ro unknown
- 1985-06-17 SU SU853909600A patent/SU1355124A3/ru active
- 1985-06-17 BG BG070701A patent/BG43864A3/xx unknown
- 1985-06-17 JP JP60130066A patent/JPS6112661A/ja active Pending
- 1985-06-18 CS CS854451A patent/CS250691B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU99085A (en) | 1987-10-31 |
| IL75199A0 (en) | 1985-09-29 |
| JPS6112661A (ja) | 1986-01-21 |
| SU1355124A3 (ru) | 1987-11-23 |
| BG43864A3 (en) | 1988-08-15 |
| FR2565975B1 (fr) | 1988-08-26 |
| DD234002A5 (de) | 1986-03-19 |
| RO92318A (ro) | 1987-08-31 |
| FR2565975A1 (fr) | 1985-12-20 |
| RO92318B (ro) | 1987-09-01 |
| CS250691B2 (en) | 1987-05-14 |
| DE3518619A1 (de) | 1985-12-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HPC4 | Succession in title of patentee |
Owner name: NITROKEMIA 2000 IPARI ES VAGYONKEZELOE RT., HU |
|
| HMM4 | Cancellation of final prot. due to non-payment of fee |