JPH11508918A - キノリン塩基の製造方法 - Google Patents
キノリン塩基の製造方法Info
- Publication number
- JPH11508918A JPH11508918A JP9505979A JP50597997A JPH11508918A JP H11508918 A JPH11508918 A JP H11508918A JP 9505979 A JP9505979 A JP 9505979A JP 50597997 A JP50597997 A JP 50597997A JP H11508918 A JPH11508918 A JP H11508918A
- Authority
- JP
- Japan
- Prior art keywords
- methylquinoline
- molar ratio
- formaldehyde
- aldehyde
- catalyst
- 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
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title claims description 45
- 238000004519 manufacturing process Methods 0.000 title abstract description 15
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical compound C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 claims abstract description 77
- 238000006243 chemical reaction Methods 0.000 claims abstract description 43
- 238000000034 method Methods 0.000 claims abstract description 39
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 34
- 150000001448 anilines Chemical class 0.000 claims abstract description 9
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract description 6
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 77
- 239000003054 catalyst Substances 0.000 claims description 61
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 45
- RNVCVTLRINQCPJ-UHFFFAOYSA-N ortho-methyl aniline Natural products CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 claims description 36
- BELFSAVWJLQIBB-UHFFFAOYSA-N 2,8-dimethylquinoline Chemical compound C1=CC=C(C)C2=NC(C)=CC=C21 BELFSAVWJLQIBB-UHFFFAOYSA-N 0.000 claims description 10
- 239000011973 solid acid Substances 0.000 claims description 9
- 239000010457 zeolite Substances 0.000 claims description 9
- 229910021536 Zeolite Inorganic materials 0.000 claims description 8
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000011959 amorphous silica alumina Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical group CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims 2
- RNVCVTLRINQCPJ-VJJZLTLGSA-N 2-methylaniline Chemical group CC1=CC=CC=C1[15NH2] RNVCVTLRINQCPJ-VJJZLTLGSA-N 0.000 claims 1
- 150000003248 quinolines Chemical class 0.000 abstract description 15
- 229940111121 antirheumatic drug quinolines Drugs 0.000 abstract description 13
- 238000010574 gas phase reaction Methods 0.000 abstract description 4
- 239000000047 product Substances 0.000 description 19
- 150000001299 aldehydes Chemical class 0.000 description 18
- 238000002474 experimental method Methods 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- DTBDAFLSBDGPEA-UHFFFAOYSA-N 3-methylquinoline Chemical compound C1=CC=CC2=CC(C)=CN=C21 DTBDAFLSBDGPEA-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- DWRUXVJOLNAHGL-UHFFFAOYSA-N 3,8-dimethylquinoline Chemical compound CC1=CC=CC2=CC(C)=CN=C21 DWRUXVJOLNAHGL-UHFFFAOYSA-N 0.000 description 3
- 238000005614 Skraup synthesis reaction Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 238000001354 calcination Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- JYUCDFZMJMRPHS-UHFFFAOYSA-N 2-acetylpyridine-3-carboxylic acid Chemical compound CC(=O)C1=NC=CC=C1C(O)=O JYUCDFZMJMRPHS-UHFFFAOYSA-N 0.000 description 2
- WHNQFLAEAOWDTD-UHFFFAOYSA-N 2-methylaniline Chemical group CC1=CC=CC=C1N.CC1=CC=CC=C1N WHNQFLAEAOWDTD-UHFFFAOYSA-N 0.000 description 2
- LMYVCXSKCQSIEQ-UHFFFAOYSA-N 5-methylquinoline Chemical compound C1=CC=C2C(C)=CC=CC2=N1 LMYVCXSKCQSIEQ-UHFFFAOYSA-N 0.000 description 2
- RLZSSWLXBLSQKI-UHFFFAOYSA-N 6,8-dimethylquinoline Chemical compound N1=CC=CC2=CC(C)=CC(C)=C21 RLZSSWLXBLSQKI-UHFFFAOYSA-N 0.000 description 2
- KDYVCOSVYOSHOL-UHFFFAOYSA-N 7-methylquinoline Chemical compound C1=CC=NC2=CC(C)=CC=C21 KDYVCOSVYOSHOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 1
- YKOLZVXSPGIIBJ-UHFFFAOYSA-N 2-Isopropylaniline Chemical compound CC(C)C1=CC=CC=C1N YKOLZVXSPGIIBJ-UHFFFAOYSA-N 0.000 description 1
- JOAWUJDFFAMORU-UHFFFAOYSA-N 3,5-dimethylquinoline Chemical compound C1=CC=C(C)C2=CC(C)=CN=C21 JOAWUJDFFAMORU-UHFFFAOYSA-N 0.000 description 1
- WLWBKLRAHBGNIU-UHFFFAOYSA-N 3-ethylquinoline Chemical compound C1=CC=CC2=CC(CC)=CN=C21 WLWBKLRAHBGNIU-UHFFFAOYSA-N 0.000 description 1
- YSHMQTRICHYLGF-UHFFFAOYSA-N 4-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=NC=C1 YSHMQTRICHYLGF-UHFFFAOYSA-N 0.000 description 1
- FAHUZGNYQXPESZ-UHFFFAOYSA-N 8-propan-2-ylquinoline Chemical compound C1=CN=C2C(C(C)C)=CC=CC2=C1 FAHUZGNYQXPESZ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- -1 Lumaldehyde Chemical compound 0.000 description 1
- XADDXAZRRQSLJH-UHFFFAOYSA-N N.[Sn+4] Chemical compound N.[Sn+4] XADDXAZRRQSLJH-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- UWAOJIWUVCMBAZ-UHFFFAOYSA-N [1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl]-dimethylazanium;chloride Chemical compound Cl.C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UWAOJIWUVCMBAZ-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000007730 finishing process Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229940045623 meridia Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 229910052680 mordenite Inorganic materials 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- OBBXFSIWZVFYJR-UHFFFAOYSA-L tin(2+);sulfate Chemical compound [Sn+2].[O-]S([O-])(=O)=O OBBXFSIWZVFYJR-UHFFFAOYSA-L 0.000 description 1
- 229910000375 tin(II) sulfate Inorganic materials 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US104995P | 1995-07-11 | 1995-07-11 | |
| US60/001,049 | 1995-07-11 | ||
| PCT/US1996/011547 WO1997003051A1 (en) | 1995-07-11 | 1996-07-11 | Process for preparing quinoline bases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH11508918A true JPH11508918A (ja) | 1999-08-03 |
Family
ID=21694139
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9505979A Pending JPH11508918A (ja) | 1995-07-11 | 1996-07-11 | キノリン塩基の製造方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5700942A (en, 2012) |
| EP (1) | EP0847389A4 (en, 2012) |
| JP (1) | JPH11508918A (en, 2012) |
| AU (1) | AU6488796A (en, 2012) |
| IN (1) | IN181930B (en, 2012) |
| TW (1) | TW343969B (en, 2012) |
| WO (1) | WO1997003051A1 (en, 2012) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5883033A (en) * | 1997-07-09 | 1999-03-16 | Phillips Petroleum Company | Hydrocarbon conversion catalyst composition and processes therefor and therewith |
| WO2011140829A1 (en) | 2010-05-14 | 2011-11-17 | The University Of Hong Kong | Solid supported gold nanoparticles, methods of use thereof, and methods for making same |
| US9604203B2 (en) | 2011-09-19 | 2017-03-28 | Exxonmobil Research And Engineering Company | Reforming catalyst compositions |
| US10501341B2 (en) | 2015-12-04 | 2019-12-10 | King Fahd University Of Petroleum And Minerals | Method for removing heavy metals from wastewater |
| US10364164B2 (en) * | 2015-12-04 | 2019-07-30 | King Fahd University Of Petroleum And Minerals | Cross-linked polymeric resin and methods for wastewater treatment |
| RU2688228C1 (ru) * | 2018-11-29 | 2019-05-21 | Федеральное государственное бюджетное научное учреждение Уфимский федеральный исследовательский центр Российской академии наук | Способ получения 2,3-диалкилхинолинов |
| RU2690535C1 (ru) * | 2018-11-29 | 2019-06-04 | Федеральное государственное бюджетное научное учреждение Уфимский федеральный исследовательский центр Российской академии наук | Способ получения 2,3-диалкилхинолинов |
| RU2697875C1 (ru) * | 2018-12-12 | 2019-08-21 | Федеральное государственное бюджетное научное учреждение Уфимский федеральный исследовательский центр Российской академии наук | Способ получения 2,3-диалкил-N-фенил-1,2,3,4-тетрагидрохинолин-4-аминов |
| RU2697876C1 (ru) * | 2018-12-14 | 2019-08-21 | Федеральное государственное бюджетное научное учреждение Уфимский федеральный исследовательский центр Российской академии наук | Способ получения 2,3-диалкил-N-фенил-1,2,3,4-тетрагидрохинолин-4-аминов |
| RU2702354C1 (ru) * | 2018-12-14 | 2019-10-08 | Федеральное государственное бюджетное научное учреждение Уфимский федеральный исследовательский центр Российской академии наук | Способ получения 2,3-диалкил-N-фенил-1,2,3,4-тетрагидрохинолин-4-аминов |
| RU2738603C1 (ru) * | 2019-12-04 | 2020-12-14 | Федеральное государственное бюджетное научное учреждение Уфимский федеральный исследовательский центр Российской академии наук | Способ получения хинолинов реакцией Скраупа в присутствии иерархического цеолита Н-Ymmm |
| CN110872252B (zh) * | 2019-12-12 | 2021-06-29 | 北京成宇化工有限公司 | 3-甲基喹啉-8-磺酰氯的制备方法 |
| RU2740912C1 (ru) * | 2020-02-18 | 2021-01-21 | Федеральное государственное бюджетное научное учреждение Уфимский федеральный исследовательский центр Российской академии наук | Способ получения хинолина реакцией Скраупа в присутствии иерархического цеолита H-ZSM-5mmm |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3020280A (en) * | 1962-02-06 | Quinoline synthesis | ||
| US3020281A (en) * | 1957-07-22 | 1962-02-06 | Reilly Tar & Chem Corp | Method of preparing quinoline |
| US3020282A (en) * | 1957-07-22 | 1962-02-06 | Reilly Tar & Chem Corp | Process of preparing quinoline |
| US4439607A (en) * | 1982-05-25 | 1984-03-27 | American Cyanamid Company | Method for the preparation of certain pyridine and quinoline 2,3-dicarboxylic anhydrides |
| DE3337569A1 (de) * | 1983-10-15 | 1985-04-25 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von chinolinen |
| US4723011A (en) * | 1985-10-28 | 1988-02-02 | American Cyanamid Company | Preparation of substituted and disubstituted-pyridine-2,3-dicarboxylate esters |
-
1996
- 1996-07-11 JP JP9505979A patent/JPH11508918A/ja active Pending
- 1996-07-11 EP EP96924434A patent/EP0847389A4/en not_active Withdrawn
- 1996-07-11 IN IN1268CA1996 patent/IN181930B/en unknown
- 1996-07-11 AU AU64887/96A patent/AU6488796A/en not_active Abandoned
- 1996-07-11 US US08/678,155 patent/US5700942A/en not_active Expired - Fee Related
- 1996-07-11 WO PCT/US1996/011547 patent/WO1997003051A1/en not_active Application Discontinuation
- 1996-07-27 TW TW085109191A patent/TW343969B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| US5700942A (en) | 1997-12-23 |
| AU6488796A (en) | 1997-02-10 |
| TW343969B (en) | 1998-11-01 |
| EP0847389A1 (en) | 1998-06-17 |
| IN181930B (en, 2012) | 1998-11-14 |
| WO1997003051A1 (en) | 1997-01-30 |
| EP0847389A4 (en) | 2001-04-11 |
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