DE1224748B - Verfahren und Vorrichtung zur kontinuierlichen Darstellung der Anthranilsaeure - Google Patents
Verfahren und Vorrichtung zur kontinuierlichen Darstellung der AnthranilsaeureInfo
- Publication number
- DE1224748B DE1224748B DEF38439A DEF0038439A DE1224748B DE 1224748 B DE1224748 B DE 1224748B DE F38439 A DEF38439 A DE F38439A DE F0038439 A DEF0038439 A DE F0038439A DE 1224748 B DE1224748 B DE 1224748B
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- alkali
- acid
- column
- anthranilic acid
- 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
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 title claims description 38
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 43
- 239000003513 alkali Substances 0.000 claims description 28
- 239000000243 solution Substances 0.000 claims description 23
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims description 20
- GVTLFGJNTIRUEG-ZHACJKMWSA-N (e)-n-(3-methoxyphenyl)-3-phenylprop-2-enamide Chemical compound COC1=CC=CC(NC(=O)\C=C\C=2C=CC=CC=2)=C1 GVTLFGJNTIRUEG-ZHACJKMWSA-N 0.000 claims description 13
- 238000002156 mixing Methods 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- SXNZFKZMKXCAFD-UHFFFAOYSA-N 2-aminobenzoic acid;sodium Chemical compound [Na].NC1=CC=CC=C1C(O)=O SXNZFKZMKXCAFD-UHFFFAOYSA-N 0.000 description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- 239000005708 Sodium hypochlorite Substances 0.000 description 3
- -1 alkali metal hypochlorite Chemical class 0.000 description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CYMRPDYINXWJFU-UHFFFAOYSA-N 2-carbamoylbenzoic acid Chemical compound NC(=O)C1=CC=CC=C1C(O)=O CYMRPDYINXWJFU-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- AJPGKIKVWCSLPU-UHFFFAOYSA-N C(C=1C(C(=O)N)=CC=CC1)(=O)O.[Na] Chemical compound C(C=1C(C(=O)N)=CC=CC1)(=O)O.[Na] AJPGKIKVWCSLPU-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010667 large scale reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF38439A DE1224748B (de) | 1962-12-01 | 1962-12-01 | Verfahren und Vorrichtung zur kontinuierlichen Darstellung der Anthranilsaeure |
| US32738263 US3322820A (en) | 1962-12-01 | 1963-12-02 | Process for the continuous production of anthranilic acid |
| CH1739265A CH472377A (de) | 1962-12-01 | 1965-12-16 | Verfahren und Vorrichtung zur Darstellung von Anthranilsäure |
| NL6516752A NL6516752A (en:Method) | 1962-12-01 | 1965-12-22 | |
| GB5461865A GB1112780A (en) | 1962-12-01 | 1965-12-23 | Process for the continuous production of anthranilic acid and the alkali metal salts thereof |
| FR44560A FR1462683A (fr) | 1962-12-01 | 1965-12-31 | Procédé et dispositif pour la fabrication continue de l'acide anthranilique |
| BE674678A BE674678A (en:Method) | 1962-12-01 | 1966-01-03 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF38439A DE1224748B (de) | 1962-12-01 | 1962-12-01 | Verfahren und Vorrichtung zur kontinuierlichen Darstellung der Anthranilsaeure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1224748B true DE1224748B (de) | 1966-09-15 |
Family
ID=5657391
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF38439A Pending DE1224748B (de) | 1962-12-01 | 1962-12-01 | Verfahren und Vorrichtung zur kontinuierlichen Darstellung der Anthranilsaeure |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3322820A (en:Method) |
| BE (1) | BE674678A (en:Method) |
| CH (1) | CH472377A (en:Method) |
| DE (1) | DE1224748B (en:Method) |
| FR (1) | FR1462683A (en:Method) |
| GB (1) | GB1112780A (en:Method) |
| NL (1) | NL6516752A (en:Method) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2815522A1 (de) * | 1978-04-11 | 1979-10-25 | Basf Ag | Verfahren zur kontinuierlichen herstellung von anthranilsaeure |
| US4276433A (en) * | 1979-01-10 | 1981-06-30 | Basf Aktiengesellschaft | Continuous preparation of anthranilic acid |
| EP2368872A1 (en) | 2010-03-25 | 2011-09-28 | Serichim S.r.l. | Process for the preparation of Gabapentin |
-
1962
- 1962-12-01 DE DEF38439A patent/DE1224748B/de active Pending
-
1963
- 1963-12-02 US US32738263 patent/US3322820A/en not_active Expired - Lifetime
-
1965
- 1965-12-16 CH CH1739265A patent/CH472377A/de not_active IP Right Cessation
- 1965-12-22 NL NL6516752A patent/NL6516752A/xx unknown
- 1965-12-23 GB GB5461865A patent/GB1112780A/en not_active Expired
- 1965-12-31 FR FR44560A patent/FR1462683A/fr not_active Expired
-
1966
- 1966-01-03 BE BE674678A patent/BE674678A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1462683A (fr) | 1966-12-16 |
| CH472377A (de) | 1969-05-15 |
| GB1112780A (en) | 1968-05-08 |
| US3322820A (en) | 1967-05-30 |
| BE674678A (en:Method) | 1966-05-03 |
| NL6516752A (en:Method) | 1967-06-23 |
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