JPS6315269B2 - - Google Patents
Info
- Publication number
- JPS6315269B2 JPS6315269B2 JP14060679A JP14060679A JPS6315269B2 JP S6315269 B2 JPS6315269 B2 JP S6315269B2 JP 14060679 A JP14060679 A JP 14060679A JP 14060679 A JP14060679 A JP 14060679A JP S6315269 B2 JPS6315269 B2 JP S6315269B2
- Authority
- JP
- Japan
- Prior art keywords
- pyridine
- formaldehyde
- picoline
- ethanol
- pyridyl
- 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
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 78
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 51
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 15
- 150000003335 secondary amines Chemical class 0.000 claims description 6
- BXGYBSJAZFGIPX-UHFFFAOYSA-N 2-pyridin-2-ylethanol Chemical compound OCCC1=CC=CC=N1 BXGYBSJAZFGIPX-UHFFFAOYSA-N 0.000 claims description 5
- DWPYQDGDWBKJQL-UHFFFAOYSA-N 2-pyridin-4-ylethanol Chemical compound OCCC1=CC=NC=C1 DWPYQDGDWBKJQL-UHFFFAOYSA-N 0.000 claims description 5
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 4
- 150000003141 primary amines Chemical class 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- QJHOHDKABVJMEC-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)ethanol Chemical compound CC1=CC=CC(CCO)=N1 QJHOHDKABVJMEC-UHFFFAOYSA-N 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229920000768 polyamine Polymers 0.000 claims description 2
- PIPCMPONTDMDST-UHFFFAOYSA-N 1-(5-ethylpyridin-2-yl)ethanol Chemical compound CCC1=CC=C(C(C)O)N=C1 PIPCMPONTDMDST-UHFFFAOYSA-N 0.000 claims 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 26
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000001577 simple distillation Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 9
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 8
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 6
- -1 2- (2,6-dimethyl-4-pyridyl)ethanol Chemical compound 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 229930040373 Paraformaldehyde Natural products 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920002866 paraformaldehyde Polymers 0.000 description 4
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- UTBIMNXEDGNJFE-UHFFFAOYSA-N 2,3,6-trimethylpyridine Chemical compound CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 2
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
- JDQNYWYMNFRKNQ-UHFFFAOYSA-N 3-ethyl-4-methylpyridine Chemical compound CCC1=CN=CC=C1C JDQNYWYMNFRKNQ-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- BRHGIEPBWOHPOH-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)ethanol Chemical compound CC1=CC(CCO)=CC=N1 BRHGIEPBWOHPOH-UHFFFAOYSA-N 0.000 description 1
- SHAFQNPHBRVPFJ-UHFFFAOYSA-N 2-(3-ethylpyridin-2-yl)ethanol Chemical compound CCC1=CC=CN=C1CCO SHAFQNPHBRVPFJ-UHFFFAOYSA-N 0.000 description 1
- FKNDBTCAFYWRHI-UHFFFAOYSA-N 2-(3-ethylpyridin-4-yl)ethanol Chemical compound CCC1=CN=CC=C1CCO FKNDBTCAFYWRHI-UHFFFAOYSA-N 0.000 description 1
- OUJMXIPHUCDRAS-UHFFFAOYSA-N 2-(5-ethylpyridin-2-yl)ethanol Chemical compound CCC1=CC=C(CCO)N=C1 OUJMXIPHUCDRAS-UHFFFAOYSA-N 0.000 description 1
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- JGXRFQKRGPKWPP-UHFFFAOYSA-N 2-pyridin-2-ylpropane-1,3-diol Chemical compound OCC(CO)C1=CC=CC=N1 JGXRFQKRGPKWPP-UHFFFAOYSA-N 0.000 description 1
- KRQAKTLJNCKGLB-UHFFFAOYSA-N 2-pyridin-4-ylprop-2-en-1-ol Chemical compound OCC(=C)C1=CC=NC=C1 KRQAKTLJNCKGLB-UHFFFAOYSA-N 0.000 description 1
- SDTJRMWVGWPOJY-UHFFFAOYSA-N 2-pyridin-4-ylpropane-1,3-diol Chemical compound OCC(CO)C1=CC=NC=C1 SDTJRMWVGWPOJY-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical class C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- ZZKDGABMFBCSRP-UHFFFAOYSA-N 3-ethyl-2-methylpyridine Chemical compound CCC1=CC=CN=C1C ZZKDGABMFBCSRP-UHFFFAOYSA-N 0.000 description 1
- VJXRKZJMGVSXPX-UHFFFAOYSA-N 4-ethylpyridine Chemical compound CCC1=CC=NC=C1 VJXRKZJMGVSXPX-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- 239000002031 ethanolic fraction Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- HVAAHUDGWQAAOJ-UHFFFAOYSA-N n-benzylethanamine Chemical compound CCNCC1=CC=CC=C1 HVAAHUDGWQAAOJ-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 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
- 150000004992 toluidines Chemical class 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14060679A JPS5665870A (en) | 1979-10-31 | 1979-10-31 | Removal of formaldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14060679A JPS5665870A (en) | 1979-10-31 | 1979-10-31 | Removal of formaldehyde |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5665870A JPS5665870A (en) | 1981-06-03 |
| JPS6315269B2 true JPS6315269B2 (de) | 1988-04-04 |
Family
ID=15272611
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14060679A Granted JPS5665870A (en) | 1979-10-31 | 1979-10-31 | Removal of formaldehyde |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5665870A (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010270008A (ja) * | 2009-05-19 | 2010-12-02 | Sanyo Chem Ind Ltd | ピリジンエタノール誘導体の製造方法 |
-
1979
- 1979-10-31 JP JP14060679A patent/JPS5665870A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010270008A (ja) * | 2009-05-19 | 2010-12-02 | Sanyo Chem Ind Ltd | ピリジンエタノール誘導体の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5665870A (en) | 1981-06-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0002901B1 (de) | Substitution und Dequaternisierung von quaternären Pyridyläthylsalzen von Pyridin- und Bipyridinbasen | |
| US3332959A (en) | 4, 4'-bipyridylium quaternary salts | |
| JPS58208266A (ja) | 改良チチバビン反応 | |
| JPS6315269B2 (de) | ||
| EP1409460B1 (de) | Verfahren für die herstellung von heterorylaminderivaten | |
| US2186769A (en) | Method for the manufacture of basic substituted carboxylic acid amides | |
| US20120171730A1 (en) | Method and substances for preparation of n-substituted pyridinium compounds | |
| US3410861A (en) | Production of beta-(2-or 4-pyridyl alkyl)-amines | |
| TW212173B (de) | ||
| CA2218480A1 (en) | Process for preparing racemic and enantiomeric 1-(pyridyl)-2-cyclohexylethylamine | |
| JP5303463B2 (ja) | シアノピリジンを含有する気体反応生成物を急冷するためのプロセス | |
| US3370059A (en) | 2-diethylaminoethylmercapto and 2-morpholinoethylmercapto-chloropyridines | |
| EP0192003A1 (de) | Herstellung von 4-substituierten Pyridinen und dabei verwendbare quaternäre Pyridinsalze | |
| JPS6016420B2 (ja) | ビニルピリジンの回収方法 | |
| JPS6016422B2 (ja) | メチロ−ル化アルキルピリジン類反応液の処理方法 | |
| US3290320A (en) | Benzoyl pyridine oximino ethers and methods for their manufacture | |
| JP2010500369A5 (de) | ||
| US3793336A (en) | Process for the preparation of 2-amino-pyridines | |
| US2442865A (en) | Heteboctcuc substituted fhenacxl | |
| JP2606968B2 (ja) | ジ―カチオンエーテルの製造 | |
| CA1310650C (en) | Process for producing 2,3,5,6-tetrachloropyridine | |
| MXPA02007060A (es) | Procedimiento para la obtencion de compuestos heterociclicos. | |
| US3577426A (en) | 4-(4-tetrahydropyranyl)pyridines | |
| CA1203804A (en) | .alpha.-(2-PYRIDYL)LOWER ALKYLAMINE | |
| US3116297A (en) | Process for the preparation of phenylpyridylalkylamines |