DE127138C - - Google Patents
Info
- Publication number
- DE127138C DE127138C DENDAT127138D DE127138DA DE127138C DE 127138 C DE127138 C DE 127138C DE NDAT127138 D DENDAT127138 D DE NDAT127138D DE 127138D A DE127138D A DE 127138DA DE 127138 C DE127138 C DE 127138C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- phthalimide
- salts
- isatoic
- excess alkali
- 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.)
- Active
Links
- XKJCHHZQLQNZHY-UHFFFAOYSA-N Phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 6
- RFQGAFQKNITSIA-UHFFFAOYSA-N 2-(carboxyamino)benzoic acid Chemical compound OC(=O)NC1=CC=CC=C1C(O)=O RFQGAFQKNITSIA-UHFFFAOYSA-N 0.000 claims description 3
- QWPPOHNGKGFGJK-UHFFFAOYSA-N Hypochlorous acid Chemical class ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RWZYAGGXGHYGMB-UHFFFAOYSA-N Anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical compound [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000006105 Hofmann reaction Methods 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N Sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Bisher war schon bekannt, dafs unterchlorigsaure Salze auf Phtalimid in Gegenwart von überschüssigem Alkali unter Bildung von Anthranilsäure einwirken.It was previously known that hypochlorous acid salts on phthalimide in the presence of act on excess alkali to form anthranilic acid.
Es wurde nun gefunden, dafs eine Einwirkung von unterchlorigsauren Salzen auf Phtalimid bezw. Salze des Phtalimids auch unter Ausschlufs von freiem Alkali stattfindet, und dafs unter diesen Bedingungen nicht Anthranilsäure, sondern Isatosäure entsteht. Dies Resultat ist insofern überraschend, als die Hofmann'sehe Reaction sonst immer unter gleichzeitiger Abspaltung von Kohlensäure verläuft. It has now been found that there is an action of hypochlorous acid salts Phthalimide and Salts of phthalimide also take place with the exclusion of free alkali, and that under these conditions it is not anthranilic acid but isatoic acid that is produced. This result is surprising insofar as the Hofmann reaction is otherwise always below simultaneous splitting off of carbonic acid takes place.
i. 100 g Phtalimid werden in 1 Mol. verdünnter Natronlauge gelöst und unter Kühlen und Rühren mit 1 Mol. Natriumhypochlorit versetzt. Nach kurzer Zeit scheiden sich glänzende Blättchen aus, die der Analyse nach die Zusammensetzung C8 Ha.N O4 Na besitzen, und in welchen das saure Natriumsalz deri. 100 g of phthalimide are dissolved in 1 mol of dilute sodium hydroxide solution, and 1 mol of sodium hypochlorite is added while cooling and stirring. After a short time, shiny flakes separate out which, according to the analysis, have the composition C 8 H a .N O 4 Na , and in which the acid sodium salt of
COOH
Isatosäure C1. HX vorliegt. COOH
Isatoic acid C 1 . HX is present.
NH-COONaNH-COONa
2. 100 g Phtalimid werden in 2 1 Wasser angerührt, auf io° gekühlt und eine Aufschlämmung von 130 g 37proc. Chlorkalk in Va 1 Wasser zugegeben. Nach einiger Zeit läfst sich die Isatosäure2. 100 g of phthalimide are dissolved in 2 l of water stirred, cooled to 10 ° and a slurry of 130 g of 37proc. Chlorinated lime in Va 1 water was added. After a while the isato acid dissolves
C6 hX\ >oC 6 hX \ > o
WH. C O W H. CO
durch - Ansäuern mit verdünnter H Cl ausfällen. precipitate by - acidification with dilute H Cl.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE127138C true DE127138C (en) |
Family
ID=395753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT127138D Active DE127138C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE127138C (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3324119A (en) * | 1963-12-23 | 1967-06-06 | Maumee Chemical Company | Production of isatoic anhydride and certain halo derivatives thereof |
| US3687951A (en) * | 1968-05-20 | 1972-08-29 | Bayer Ag | Process for the preparation of isatoic anhydride |
| EP0020969A1 (en) * | 1979-06-20 | 1981-01-07 | BASF Aktiengesellschaft | Process for the preparation of a mixture of 3-chloro-anthranilic acid alkyl ester and 6-chloro-anthranilic acid alkyl ester |
| US4328339A (en) * | 1979-01-26 | 1982-05-04 | Basf Aktiengesellschaft | Continuous preparation of isatoic anhydride |
| US6490141B2 (en) | 1999-05-28 | 2002-12-03 | Ellenberger & Poensgen Gmbh | Power distribution system |
-
0
- DE DENDAT127138D patent/DE127138C/de active Active
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3324119A (en) * | 1963-12-23 | 1967-06-06 | Maumee Chemical Company | Production of isatoic anhydride and certain halo derivatives thereof |
| US3687951A (en) * | 1968-05-20 | 1972-08-29 | Bayer Ag | Process for the preparation of isatoic anhydride |
| US4328339A (en) * | 1979-01-26 | 1982-05-04 | Basf Aktiengesellschaft | Continuous preparation of isatoic anhydride |
| EP0020969A1 (en) * | 1979-06-20 | 1981-01-07 | BASF Aktiengesellschaft | Process for the preparation of a mixture of 3-chloro-anthranilic acid alkyl ester and 6-chloro-anthranilic acid alkyl ester |
| US6490141B2 (en) | 1999-05-28 | 2002-12-03 | Ellenberger & Poensgen Gmbh | Power distribution system |
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