PL413157A1 - Method for obtaining 4-chlorophthalonitrile - Google Patents
Method for obtaining 4-chlorophthalonitrileInfo
- Publication number
- PL413157A1 PL413157A1 PL413157A PL41315715A PL413157A1 PL 413157 A1 PL413157 A1 PL 413157A1 PL 413157 A PL413157 A PL 413157A PL 41315715 A PL41315715 A PL 41315715A PL 413157 A1 PL413157 A1 PL 413157A1
- Authority
- PL
- Poland
- Prior art keywords
- chlorophthalonitrile
- chlorophthalamide
- chlorophthalimide
- obtaining
- dehydration
- Prior art date
Links
- SZSLISKYJBQHQC-UHFFFAOYSA-N 4-chlorobenzene-1,2-dicarbonitrile Chemical compound ClC1=CC=C(C#N)C(C#N)=C1 SZSLISKYJBQHQC-UHFFFAOYSA-N 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 6
- YGIFSVAYJLFDLC-UHFFFAOYSA-N 4-chlorobenzene-1,2-dicarboxamide Chemical compound NC(=O)C1=CC=C(Cl)C=C1C(N)=O YGIFSVAYJLFDLC-UHFFFAOYSA-N 0.000 abstract 4
- BGJNRQSGJHVURK-UHFFFAOYSA-N 5-chloroisoindole-1,3-dione Chemical compound ClC1=CC=C2C(=O)NC(=O)C2=C1 BGJNRQSGJHVURK-UHFFFAOYSA-N 0.000 abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 2
- 235000011114 ammonium hydroxide Nutrition 0.000 abstract 2
- 238000005915 ammonolysis reaction Methods 0.000 abstract 2
- 230000018044 dehydration Effects 0.000 abstract 2
- 238000006297 dehydration reaction Methods 0.000 abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 2
- DVIPPHSQIBKWSA-UHFFFAOYSA-N 4-chlorophthalic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1C(O)=O DVIPPHSQIBKWSA-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 229910002651 NO3 Inorganic materials 0.000 abstract 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 abstract 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 229910052938 sodium sulfate Inorganic materials 0.000 abstract 1
- 235000011152 sodium sulphate Nutrition 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Sposób otrzymywania 4-chloroftalonitrylu, polegający na otrzymaniu 4-chloroftalimidu, następnie poddaniu 4-chloroftalimidu amonolizie do 4-chloroftalamidu przy użyciu wody amoniakalnej i odwodnieniu 4-chloroftalamidu do 4-chloroftalonitrylu, z wykorzystaniem reakcji odwodnienia amidu do nitrylu za pomocą chlorku tionylu w środowisku N,N-dimetyloformamidu, charakteryzuje się tym, że 4-chloroftalimid otrzymuje się w reakcji imidowania soli monosodowej kwasu 4-chloroftalowego za pomocą mocznika w środowisku glikolu etylenowego, dietylenowego lub propylenowego, w obecności kwaśnego siarczanu sodu, kwasu p-toluenosulfonowego lub kwasu amidosulfonowego. Reakcję amonolizy 4-chloroftalimidu do 4-chloroftalamidu prowadzi się w 25% wodzie amoniakalnej z dodatkiem soli amonowej, jak chlorek, siarczan, azotan lub węglan, po czym 4-chloroftalamid odwadnia się do 4-chloroftalonitrylu działaniem chlorku tionylu w środowisku N,N-dimetyloformamidu.The method of obtaining 4-chlorophthalonitrile, which consists in obtaining 4-chlorophthalimide, then subjecting 4-chlorophthalimide to ammonolysis to 4-chlorophthalamide using ammonia water and dehydration of 4-chlorophthalamide to 4-chlorophthalonitrile, using the dehydration of amide to nitrile with thionyl chloride in the environment N, N-dimethylformamide is characterized in that 4-chlorophthalimide is obtained by imidating the monosodium salt of 4-chlorophthalic acid with the use of urea in an ethylene, diethylene or propylene glycol medium, in the presence of sodium sulfate, p-toluenesulfonic acid or sulfamic acid . The ammonolysis reaction of 4-chlorophthalimide to 4-chlorophthalamide is carried out in 25% ammonia water with the addition of an ammonium salt, such as chloride, sulfate, nitrate or carbonate, after which 4-chlorophthalamide is dehydrated to 4-chlorophthalonitrile by the action of thionyl chloride in an N, N- environment dimethylformamide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL413157A PL227254B1 (en) | 2015-07-16 | 2015-07-16 | Method for obtaining 4-chlorophthalonitrile |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL413157A PL227254B1 (en) | 2015-07-16 | 2015-07-16 | Method for obtaining 4-chlorophthalonitrile |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL413157A1 true PL413157A1 (en) | 2017-01-30 |
| PL227254B1 PL227254B1 (en) | 2017-11-30 |
Family
ID=57867760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL413157A PL227254B1 (en) | 2015-07-16 | 2015-07-16 | Method for obtaining 4-chlorophthalonitrile |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL227254B1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110396055B (en) * | 2019-08-31 | 2022-12-23 | 三门峡环宇生化科技有限公司 | Method for directly synthesizing parachlorobenzonitrile from parachlorobenzoic acid and urea |
-
2015
- 2015-07-16 PL PL413157A patent/PL227254B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL227254B1 (en) | 2017-11-30 |
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