DE1768232A1 - Verfahren zur Herstellung von 2,6-Dichlorbenzamid und daraus herstellbarem 2,6-Dichlorbenzonitril - Google Patents
Verfahren zur Herstellung von 2,6-Dichlorbenzamid und daraus herstellbarem 2,6-DichlorbenzonitrilInfo
- Publication number
- DE1768232A1 DE1768232A1 DE19681768232 DE1768232A DE1768232A1 DE 1768232 A1 DE1768232 A1 DE 1768232A1 DE 19681768232 DE19681768232 DE 19681768232 DE 1768232 A DE1768232 A DE 1768232A DE 1768232 A1 DE1768232 A1 DE 1768232A1
- Authority
- DE
- Germany
- Prior art keywords
- chloride
- iodine
- under
- halide
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- JHSPCUHPSIUQRB-UHFFFAOYSA-N 2,6-dichlorobenzamide Chemical compound NC(=O)C1=C(Cl)C=CC=C1Cl JHSPCUHPSIUQRB-UHFFFAOYSA-N 0.000 title description 3
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims description 12
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 12
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 239000011630 iodine Substances 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 229910001507 metal halide Inorganic materials 0.000 claims description 6
- 150000005309 metal halides Chemical class 0.000 claims description 6
- 239000011592 zinc chloride Substances 0.000 claims description 6
- 235000005074 zinc chloride Nutrition 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 231100000518 lethal Toxicity 0.000 claims 1
- 230000001665 lethal effect Effects 0.000 claims 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000001256 steam distillation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- -1 1,2-epoxy-2,6,6-trichloro-cyclohexane-carbonic acid Chemical compound 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 229910015449 FeCU Inorganic materials 0.000 description 1
- 101100316117 Rattus norvegicus Unc50 gene Proteins 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000005899 aromatization reaction Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 235000020130 leben Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6706282A NL6706282A (en:Method) | 1967-05-04 | 1967-05-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1768232A1 true DE1768232A1 (de) | 1971-11-18 |
Family
ID=19800037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681768232 Pending DE1768232A1 (de) | 1967-05-04 | 1968-04-18 | Verfahren zur Herstellung von 2,6-Dichlorbenzamid und daraus herstellbarem 2,6-Dichlorbenzonitril |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3576867A (en:Method) |
| AT (2) | AT283329B (en:Method) |
| BE (1) | BE714566A (en:Method) |
| CH (1) | CH529099A (en:Method) |
| DE (1) | DE1768232A1 (en:Method) |
| ES (1) | ES353404A1 (en:Method) |
| FR (1) | FR1561022A (en:Method) |
| GB (1) | GB1206513A (en:Method) |
| IL (1) | IL29927A (en:Method) |
| NL (1) | NL6706282A (en:Method) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4766103A (en) * | 1986-07-07 | 1988-08-23 | Phillips Petroleum Company | Preparation of 1,4-dichlorobenzene |
-
1967
- 1967-05-04 NL NL6706282A patent/NL6706282A/xx unknown
-
1968
- 1968-04-18 DE DE19681768232 patent/DE1768232A1/de active Pending
- 1968-04-30 US US725537A patent/US3576867A/en not_active Expired - Lifetime
- 1968-05-01 CH CH647868A patent/CH529099A/de not_active IP Right Cessation
- 1968-05-01 GB GB20578/68A patent/GB1206513A/en not_active Expired
- 1968-05-02 ES ES353404A patent/ES353404A1/es not_active Expired
- 1968-05-02 BE BE714566D patent/BE714566A/xx unknown
- 1968-05-02 AT AT423568A patent/AT283329B/de not_active IP Right Cessation
- 1968-05-02 AT AT960169A patent/AT286272B/de not_active IP Right Cessation
- 1968-05-03 FR FR1561022D patent/FR1561022A/fr not_active Expired
- 1968-05-03 IL IL29927A patent/IL29927A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3576867A (en) | 1971-04-27 |
| IL29927A (en) | 1972-03-28 |
| GB1206513A (en) | 1970-09-23 |
| ES353404A1 (es) | 1969-10-01 |
| IL29927A0 (en) | 1968-07-25 |
| NL6706282A (en:Method) | 1968-11-05 |
| AT286272B (de) | 1970-12-10 |
| BE714566A (en:Method) | 1968-11-04 |
| AT283329B (de) | 1970-08-10 |
| CH529099A (de) | 1972-10-15 |
| FR1561022A (en:Method) | 1969-03-21 |
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