NO130114B - - Google Patents
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- Publication number
- NO130114B NO130114B NO694398A NO439869A NO130114B NO 130114 B NO130114 B NO 130114B NO 694398 A NO694398 A NO 694398A NO 439869 A NO439869 A NO 439869A NO 130114 B NO130114 B NO 130114B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- nicotinic acid
- mother liquor
- brought
- pyridine carboxylic
- Prior art date
Links
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 55
- 239000012452 mother liquor Substances 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 32
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 25
- 229910017604 nitric acid Inorganic materials 0.000 claims description 25
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 17
- 230000002378 acidificating effect Effects 0.000 claims description 14
- 230000003647 oxidation Effects 0.000 claims description 14
- 238000007254 oxidation reaction Methods 0.000 claims description 14
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 132
- 235000001968 nicotinic acid Nutrition 0.000 description 67
- 229960003512 nicotinic acid Drugs 0.000 description 66
- 239000011664 nicotinic acid Substances 0.000 description 66
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 description 32
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000007795 chemical reaction product Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 230000007306 turnover Effects 0.000 description 13
- 229940081066 picolinic acid Drugs 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 8
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- MPFLRYZEEAQMLQ-UHFFFAOYSA-N dinicotinic acid Chemical compound OC(=O)C1=CN=CC(C(O)=O)=C1 MPFLRYZEEAQMLQ-UHFFFAOYSA-N 0.000 description 8
- 229910052719 titanium Inorganic materials 0.000 description 8
- 239000010936 titanium Substances 0.000 description 8
- 238000005119 centrifugation Methods 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- LVPMIMZXDYBCDF-UHFFFAOYSA-N isocinchomeronic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)N=C1 LVPMIMZXDYBCDF-UHFFFAOYSA-N 0.000 description 5
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical class C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 150000003222 pyridines Chemical class 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- ZZKDGABMFBCSRP-UHFFFAOYSA-N 3-ethyl-2-methylpyridine Chemical compound CCC1=CC=CN=C1C ZZKDGABMFBCSRP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- RNPNPEKBPDIYQF-UHFFFAOYSA-N nitric acid;pyridine-3-carboxylic acid Chemical compound O[N+]([O-])=O.OC(=O)C1=CC=CN=C1 RNPNPEKBPDIYQF-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- BZFGKBQHQJVAHS-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC(C(F)(F)F)=C1 BZFGKBQHQJVAHS-UHFFFAOYSA-N 0.000 description 1
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- WYNHBAHYKOLIIX-UHFFFAOYSA-N [N+](=O)(O)[O-].N1=C(C=CC=C1)C(=O)O Chemical compound [N+](=O)(O)[O-].N1=C(C=CC=C1)C(=O)O WYNHBAHYKOLIIX-UHFFFAOYSA-N 0.000 description 1
- WDENQIQQYWYTPO-IBGZPJMESA-N acalabrutinib Chemical compound CC#CC(=O)N1CCC[C@H]1C1=NC(C=2C=CC(=CC=2)C(=O)NC=2N=CC=CC=2)=C2N1C=CN=C2N WDENQIQQYWYTPO-IBGZPJMESA-N 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- MUYSADWCWFFZKR-UHFFFAOYSA-N cinchomeronic acid Chemical compound OC(=O)C1=CC=NC=C1C(O)=O MUYSADWCWFFZKR-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002814 niacins Chemical class 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1668868A CH495990A (de) | 1968-11-08 | 1968-11-08 | Verfahren zur Herstellung von Pyridincarbonsäuren |
| CH273269A CH504437A (de) | 1968-11-08 | 1969-02-24 | Verfahren zur Herstellung von Pyridincarbonsäuren |
| CH862269A CH511848A (de) | 1968-11-08 | 1969-06-06 | Verfahren zur Herstellung von Pyridincarbonsäuren |
| CH1175969A CH527193A (de) | 1968-11-08 | 1969-08-01 | Verfahren zur Herstellung von Pyridincarbonsäuren |
| CH1416869A CH548394A (de) | 1969-09-19 | 1969-09-19 | Verfahren zur herstellung von pyridincarbonsaeuren. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO130114B true NO130114B (de) | 1974-07-08 |
Family
ID=27509078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO694398A NO130114B (de) | 1968-11-08 | 1969-11-06 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3657259A (de) |
| AT (1) | AT293388B (de) |
| BE (1) | BE741373A (de) |
| DE (1) | DE1956117C3 (de) |
| DK (1) | DK126652B (de) |
| FR (1) | FR2030070A1 (de) |
| GB (1) | GB1222778A (de) |
| HU (1) | HU162275B (de) |
| IT (1) | IT1046927B (de) |
| NL (1) | NL162640C (de) |
| NO (1) | NO130114B (de) |
| PL (1) | PL80332B1 (de) |
| RO (1) | RO56145A (de) |
| SE (1) | SE379539B (de) |
| YU (1) | YU34402B (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4001257A (en) * | 1972-12-02 | 1977-01-04 | Nippon Soda Company Limited | Process for producing nicotinic acid |
| US5520828A (en) * | 1994-06-16 | 1996-05-28 | Lever Brothers Company, Division Of Conopco, Inc. | Fabric conditioners derived from pyridine carboxylic acids |
-
1969
- 1969-10-28 US US871951A patent/US3657259A/en not_active Expired - Lifetime
- 1969-11-05 YU YU2771/69A patent/YU34402B/xx unknown
- 1969-11-06 RO RO196961489A patent/RO56145A/ro unknown
- 1969-11-06 AT AT1043469A patent/AT293388B/de active
- 1969-11-06 BE BE741373D patent/BE741373A/xx not_active IP Right Cessation
- 1969-11-06 DK DK587869AA patent/DK126652B/da not_active IP Right Cessation
- 1969-11-06 NO NO694398A patent/NO130114B/no unknown
- 1969-11-06 SE SE6915254A patent/SE379539B/xx unknown
- 1969-11-06 HU HULO351A patent/HU162275B/hu unknown
- 1969-11-07 NL NL6916844.A patent/NL162640C/xx not_active IP Right Cessation
- 1969-11-07 GB GB54683/69A patent/GB1222778A/en not_active Expired
- 1969-11-07 DE DE1956117A patent/DE1956117C3/de not_active Expired
- 1969-11-07 FR FR6938523A patent/FR2030070A1/fr not_active Withdrawn
- 1969-11-07 PL PL1969136745A patent/PL80332B1/pl unknown
- 1969-11-08 IT IT6941288A patent/IT1046927B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| SE379539B (de) | 1975-10-13 |
| DK126652B (da) | 1973-08-06 |
| HU162275B (de) | 1973-01-29 |
| NL6916844A (de) | 1970-05-12 |
| DE1956117C3 (de) | 1975-09-04 |
| GB1222778A (en) | 1971-02-17 |
| NL162640C (nl) | 1980-06-16 |
| YU34402B (en) | 1979-07-10 |
| DE1956117A1 (de) | 1970-06-11 |
| RO56145A (de) | 1974-03-01 |
| US3657259A (en) | 1972-04-18 |
| IT1046927B (it) | 1980-07-31 |
| NL162640B (nl) | 1980-01-15 |
| PL80332B1 (en) | 1975-08-30 |
| DE1956117B2 (de) | 1975-01-23 |
| AT293388B (de) | 1971-10-11 |
| BE741373A (de) | 1970-04-16 |
| YU277169A (en) | 1978-12-31 |
| FR2030070A1 (de) | 1970-10-30 |
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