CA1136147A - Process for the purification of nicotinic acid amide ii - Google Patents
Process for the purification of nicotinic acid amide iiInfo
- Publication number
- CA1136147A CA1136147A CA000382757A CA382757A CA1136147A CA 1136147 A CA1136147 A CA 1136147A CA 000382757 A CA000382757 A CA 000382757A CA 382757 A CA382757 A CA 382757A CA 1136147 A CA1136147 A CA 1136147A
- Authority
- CA
- Canada
- Prior art keywords
- nicotinamide
- solution
- exchanger
- nicotinic acid
- ion
- 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.)
- Expired
Links
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 title claims abstract description 76
- 235000005152 nicotinamide Nutrition 0.000 title claims abstract description 38
- 239000011570 nicotinamide Substances 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims abstract description 22
- 238000000746 purification Methods 0.000 title description 3
- 229960003966 nicotinamide Drugs 0.000 claims abstract description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000001953 recrystallisation Methods 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 4
- 150000002500 ions Chemical class 0.000 claims description 14
- 150000001768 cations Chemical class 0.000 claims description 8
- 150000001450 anions Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 4
- 239000003456 ion exchange resin Substances 0.000 claims description 4
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 4
- 238000011084 recovery Methods 0.000 claims description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 abstract description 20
- 239000011664 nicotinic acid Substances 0.000 abstract description 13
- 235000001968 nicotinic acid Nutrition 0.000 abstract description 13
- 229960003512 nicotinic acid Drugs 0.000 abstract description 10
- 150000003839 salts Chemical class 0.000 abstract description 3
- 230000002349 favourable effect Effects 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 16
- 239000004793 Polystyrene Substances 0.000 description 11
- 239000012535 impurity Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- -1 nicotinate ions Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- KFLRWGSAMLBHBV-UHFFFAOYSA-M sodium;pyridine-3-carboxylate Chemical compound [Na+].[O-]C(=O)C1=CC=CN=C1 KFLRWGSAMLBHBV-UHFFFAOYSA-M 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 1
- LQVXSNNAFNGRAH-QHCPKHFHSA-N BMS-754807 Chemical compound C([C@@]1(C)C(=O)NC=2C=NC(F)=CC=2)CCN1C(=NN1C=CC=C11)N=C1NC(=NN1)C=C1C1CC1 LQVXSNNAFNGRAH-QHCPKHFHSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- ONJIBHRZSUEBDS-UHFFFAOYSA-N azane;pyridine-3-carboxylic acid Chemical compound [NH4+].[O-]C(=O)C1=CC=CN=C1 ONJIBHRZSUEBDS-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229960000443 hydrochloric acid Drugs 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- WCZVUZYEOJQHNJ-UHFFFAOYSA-M potassium;pyridine-3-carboxylate Chemical compound [K+].[O-]C(=O)C1=CC=CN=C1 WCZVUZYEOJQHNJ-UHFFFAOYSA-M 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3028791.3 | 1980-07-30 | ||
| DE19803028791 DE3028791A1 (de) | 1980-07-30 | 1980-07-30 | Verfahren zur reinigung von nicotinsaeureamid ii. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1136147A true CA1136147A (en) | 1982-11-23 |
Family
ID=6108402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000382757A Expired CA1136147A (en) | 1980-07-30 | 1981-07-29 | Process for the purification of nicotinic acid amide ii |
Country Status (9)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0424316A3 (en) * | 1989-10-19 | 1991-09-25 | Ciba-Geigy Ag | Purification of 2-aryl-2h-benzotriazoles |
| TW539670B (en) * | 1998-07-21 | 2003-07-01 | Reilly Ind Inc | Processes for producing highly pure nicotinamide |
| CN114634269B (zh) * | 2020-12-15 | 2022-12-02 | 山东潍坊润丰化工股份有限公司 | 一种从废水中回收烟酰胺的方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2471518A (en) * | 1949-05-31 | Nicotinic acid amide and processes | ||
| US2483250A (en) * | 1949-09-27 | Tt a it tt | ||
| US2412749A (en) * | 1942-03-02 | 1946-12-17 | Gelatin Products Corp | Method of preparing nicotinamide |
| US2544157A (en) * | 1947-05-08 | 1951-03-06 | Upjohn Co | Purification of nicotinamide |
| DE828247C (de) * | 1948-10-02 | 1953-07-02 | Degussa | Verfahren zur Herstellung von Nicotinsaeureamid |
| GB879551A (en) * | 1957-10-28 | 1961-10-11 | Merck & Co Inc | Ion-exchange purification of nicotinamide |
| US2932648A (en) * | 1958-10-06 | 1960-04-12 | Abbott Lab | Nicotinamide process |
| US3678060A (en) * | 1970-08-03 | 1972-07-18 | Merck & Co Inc | Process for separating an acid from an amide |
| DE2517054C2 (de) * | 1975-04-17 | 1985-04-25 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Nicotinsäureamid |
| DE2517053A1 (de) * | 1975-04-17 | 1976-10-28 | Degussa | Verfahren zur gewinnung von nicotinsaeureamid |
-
1980
- 1980-07-30 DE DE19803028791 patent/DE3028791A1/de not_active Withdrawn
-
1981
- 1981-07-20 IN IN814/CAL/81A patent/IN154600B/en unknown
- 1981-07-23 ES ES504207A patent/ES504207A0/es active Granted
- 1981-07-25 EP EP81105903A patent/EP0045080B1/de not_active Expired
- 1981-07-25 DE DE8181105903T patent/DE3166837D1/de not_active Expired
- 1981-07-27 MX MX819569U patent/MX6429E/es unknown
- 1981-07-29 US US06/288,187 patent/US4447614A/en not_active Expired - Fee Related
- 1981-07-29 JP JP56117903A patent/JPS5754173A/ja active Pending
- 1981-07-29 CA CA000382757A patent/CA1136147A/en not_active Expired
- 1981-07-29 BR BR8104892A patent/BR8104892A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX6429E (es) | 1985-05-30 |
| EP0045080B1 (de) | 1984-10-24 |
| DE3166837D1 (en) | 1984-11-29 |
| ES8206482A1 (es) | 1982-08-16 |
| US4447614A (en) | 1984-05-08 |
| DE3028791A1 (de) | 1982-02-25 |
| ES504207A0 (es) | 1982-08-16 |
| EP0045080A1 (de) | 1982-02-03 |
| IN154600B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-11-17 |
| JPS5754173A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-03-31 |
| BR8104892A (pt) | 1982-04-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |