TWI336325B - Process for the manufacture of 2,3-dichloropyridine - Google Patents
Process for the manufacture of 2,3-dichloropyridine Download PDFInfo
- Publication number
- TWI336325B TWI336325B TW094100423A TW94100423A TWI336325B TW I336325 B TWI336325 B TW I336325B TW 094100423 A TW094100423 A TW 094100423A TW 94100423 A TW94100423 A TW 94100423A TW I336325 B TWI336325 B TW I336325B
- Authority
- TW
- Taiwan
- Prior art keywords
- copper
- amino
- molar ratio
- hydrochloric acid
- solution
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 123
- MAKFMOSBBNKPMS-UHFFFAOYSA-N 2,3-dichloropyridine Chemical compound ClC1=CC=CN=C1Cl MAKFMOSBBNKPMS-UHFFFAOYSA-N 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 96
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 claims description 71
- 239000000203 mixture Substances 0.000 claims description 59
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 56
- 229910052802 copper Inorganic materials 0.000 claims description 48
- 239000010949 copper Substances 0.000 claims description 48
- 239000003795 chemical substances by application Substances 0.000 claims description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 239000007789 gas Substances 0.000 claims description 26
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 25
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 24
- -1 amino-2-chloropyrene Chemical compound 0.000 claims description 22
- MEQBJJUWDCYIAB-UHFFFAOYSA-N 2-chloropyridin-3-amine Chemical compound NC1=CC=CN=C1Cl MEQBJJUWDCYIAB-UHFFFAOYSA-N 0.000 claims description 18
- 239000002585 base Substances 0.000 claims description 16
- 230000002140 halogenating effect Effects 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- 239000012954 diazonium Substances 0.000 claims description 12
- 150000001989 diazonium salts Chemical class 0.000 claims description 12
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 11
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 11
- 230000003647 oxidation Effects 0.000 claims description 11
- 238000007254 oxidation reaction Methods 0.000 claims description 11
- 229960003966 nicotinamide Drugs 0.000 claims description 10
- 235000005152 nicotinamide Nutrition 0.000 claims description 10
- 239000011570 nicotinamide Substances 0.000 claims description 10
- 239000012320 chlorinating reagent Substances 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 6
- MUKAGFLFIMVSQN-UHFFFAOYSA-N 3-n-benzylpyridine-2,3-diamine Chemical compound NC1=NC=CC=C1NCC1=CC=CC=C1 MUKAGFLFIMVSQN-UHFFFAOYSA-N 0.000 claims description 5
- WDRNCZFWROPPSH-UHFFFAOYSA-N C(CCCCCCCCC)N.N1=CC=CC(=C1)C1N(C)CCC1 Chemical compound C(CCCCCCCCC)N.N1=CC=CC(=C1)C1N(C)CCC1 WDRNCZFWROPPSH-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 238000012360 testing method Methods 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 4
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims description 4
- 239000011833 salt mixture Substances 0.000 claims description 4
- 229910000831 Steel Inorganic materials 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000010959 steel Substances 0.000 claims description 3
- 229910021592 Copper(II) chloride Inorganic materials 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000013043 chemical agent Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- XNYFAJZQMFNULQ-UHFFFAOYSA-N pyridin-1-ium-3-amine;chloride Chemical compound Cl.NC1=CC=CN=C1 XNYFAJZQMFNULQ-UHFFFAOYSA-N 0.000 claims description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims 2
- NEQIRASUEZEXJF-UHFFFAOYSA-N 2-chloropyridin-3-amine;hydrochloride Chemical compound Cl.NC1=CC=CN=C1Cl NEQIRASUEZEXJF-UHFFFAOYSA-N 0.000 claims 1
- BYAKIEBZLGEIAF-UHFFFAOYSA-N 2-pyridin-1-ium-2-ylpyridine;chloride Chemical compound Cl.N1=CC=CC=C1C1=CC=CC=N1 BYAKIEBZLGEIAF-UHFFFAOYSA-N 0.000 claims 1
- XCEAGAJKBRACAD-UHFFFAOYSA-N [Cu].[Ru] Chemical compound [Cu].[Ru] XCEAGAJKBRACAD-UHFFFAOYSA-N 0.000 claims 1
- GCYKKHRWVYGZMD-UHFFFAOYSA-N [Ru].[Cu]=O Chemical compound [Ru].[Cu]=O GCYKKHRWVYGZMD-UHFFFAOYSA-N 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001509 sodium citrate Substances 0.000 claims 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical group O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 claims 1
- 239000000243 solution Substances 0.000 description 47
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 239000007864 aqueous solution Substances 0.000 description 32
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000002309 gasification Methods 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical group [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 238000005660 chlorination reaction Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 239000005751 Copper oxide Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000005708 Sodium hypochlorite Substances 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 229910000431 copper oxide Inorganic materials 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000006193 diazotization reaction Methods 0.000 description 5
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 5
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 4
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000012296 anti-solvent Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 229960002715 nicotine Drugs 0.000 description 4
- 238000006462 rearrangement reaction Methods 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 239000012485 toluene extract Substances 0.000 description 4
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 3
- MJVZSRZTBDMYLX-UHFFFAOYSA-N 2,6-dichloropyridin-3-amine Chemical compound NC1=CC=C(Cl)N=C1Cl MJVZSRZTBDMYLX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WBMLFMGHAORUTE-UHFFFAOYSA-N 1,2-dichloropyrene Chemical compound C1=CC=C2C=CC3=C(Cl)C(Cl)=CC4=CC=C1C2=C43 WBMLFMGHAORUTE-UHFFFAOYSA-N 0.000 description 1
- CJYIFBGXLCPMDQ-UHFFFAOYSA-N 1,3-dipyridin-3-ylurea Chemical compound C=1C=CN=CC=1NC(=O)NC1=CC=CN=C1 CJYIFBGXLCPMDQ-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 1
- FNRMMDCDHWCQTH-UHFFFAOYSA-N 2-chloropyridine;3-chloropyridine;4-chloropyridine Chemical compound ClC1=CC=NC=C1.ClC1=CC=CN=C1.ClC1=CC=CC=N1 FNRMMDCDHWCQTH-UHFFFAOYSA-N 0.000 description 1
- SOCJVFLTFAWZPV-UHFFFAOYSA-N 2h-oxazin-6-amine Chemical compound NC1=CC=CNO1 SOCJVFLTFAWZPV-UHFFFAOYSA-N 0.000 description 1
- GHCKERHPOQWERJ-UHFFFAOYSA-N 3-aminoacridine Chemical compound C1=CC=CC2=NC3=CC(N)=CC=C3C=C21 GHCKERHPOQWERJ-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- SQMMQAWYLLBBIN-UHFFFAOYSA-N C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=NC=C1 Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=NC=C1 SQMMQAWYLLBBIN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000007107 Gatterman reaction Methods 0.000 description 1
- 108010068370 Glutens Proteins 0.000 description 1
- 238000007167 Hofmann rearrangement reaction Methods 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- QAAXRTPGRLVPFH-UHFFFAOYSA-N [Bi].[Cu] Chemical compound [Bi].[Cu] QAAXRTPGRLVPFH-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- KRZRNXHQZJZPPZ-UHFFFAOYSA-N benzoyl(trimethyl)azanium Chemical compound C[N+](C)(C)C(=O)C1=CC=CC=C1 KRZRNXHQZJZPPZ-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- PSFLGCAUZCAVBI-UHFFFAOYSA-N copper strontium Chemical compound [Cu].[Sr] PSFLGCAUZCAVBI-UHFFFAOYSA-N 0.000 description 1
- 239000012045 crude solution Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 235000021312 gluten Nutrition 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Inorganic materials Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 1
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- YPJRHEKCFKOVRT-UHFFFAOYSA-N lerociclib Chemical compound C1CN(C(C)C)CCN1C(C=N1)=CC=C1NC1=NC=C(C=C2N3C4(CCCCC4)CNC2=O)C3=N1 YPJRHEKCFKOVRT-UHFFFAOYSA-N 0.000 description 1
- 230000002934 lysing effect Effects 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- FXADMRZICBQPQY-UHFFFAOYSA-N orthotelluric acid Chemical compound O[Te](O)(O)(O)(O)O FXADMRZICBQPQY-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005373 pervaporation Methods 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- NGXSWUFDCSEIOO-UHFFFAOYSA-N pyrrolidin-3-amine Chemical compound NC1CCNC1 NGXSWUFDCSEIOO-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 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
- C07D213/61—Halogen atoms or nitro radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4402—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 2, e.g. pheniramine, bisacodyl
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4406—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 3, e.g. zimeldine
-
- 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- 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
- C07D213/82—Amides; Imides in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Output Control And Ontrol Of Special Type Engine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53906804P | 2004-01-23 | 2004-01-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200533654A TW200533654A (en) | 2005-10-16 |
| TWI336325B true TWI336325B (en) | 2011-01-21 |
Family
ID=34807252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW094100423A TWI336325B (en) | 2004-01-23 | 2005-01-07 | Process for the manufacture of 2,3-dichloropyridine |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US20070161797A1 (https=) |
| EP (1) | EP1706381A2 (https=) |
| JP (1) | JP2007523065A (https=) |
| KR (1) | KR20060130618A (https=) |
| CN (1) | CN1910152B (https=) |
| AR (1) | AR048217A1 (https=) |
| AU (1) | AU2005206576A1 (https=) |
| BR (1) | BRPI0506502A (https=) |
| CA (1) | CA2553850A1 (https=) |
| CO (1) | CO5720997A2 (https=) |
| IL (1) | IL176420A (https=) |
| MX (1) | MXPA06008208A (https=) |
| MY (1) | MY136794A (https=) |
| RU (1) | RU2359960C2 (https=) |
| TW (1) | TWI336325B (https=) |
| UA (1) | UA86604C2 (https=) |
| WO (1) | WO2005070888A2 (https=) |
| ZA (1) | ZA200605616B (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI1599463T1 (sl) * | 2003-01-28 | 2013-10-30 | E.I. Du Pont De Nemours And Company | Ciano antranilamidni insekticidi |
| AU2006283181A1 (en) * | 2005-08-24 | 2007-03-01 | E. I. Du Pont De Nemours And Company | Anthranilamides for controlling invertebrate pests |
| CN100357272C (zh) * | 2006-02-06 | 2007-12-26 | 南京广通医药化工有限责任公司 | 一种2,3－二氯吡啶的合成方法 |
| TW200946504A (en) * | 2008-03-13 | 2009-11-16 | Du Pont | Improved process for the manufacture of 2,3-dichloropyridine |
| CN101302190B (zh) * | 2008-06-30 | 2011-07-27 | 河北亚诺化工有限公司 | 一种制备2,3-二氯吡啶的方法 |
| US8293918B2 (en) * | 2008-12-19 | 2012-10-23 | Jubilant Organosys Limited | Process for producing dihalopyridines |
| CN102086174B (zh) * | 2011-03-07 | 2012-10-31 | 南京广通医药化工有限责任公司 | 2,3-二氯吡啶的生产方法 |
| CN102153507B (zh) | 2011-03-13 | 2012-11-21 | 联化科技股份有限公司 | 一种2，3-二氯吡啶的制备方法 |
| CN102558039A (zh) * | 2012-01-13 | 2012-07-11 | 江苏中邦制药有限公司 | 一种2,3-二氯吡啶的制备方法 |
| CN102584693B (zh) * | 2012-02-09 | 2013-08-14 | 雅本化学股份有限公司 | 一种高纯度2-氯-3-氨基吡啶盐酸盐的制备方法 |
| CN104662003A (zh) | 2012-06-01 | 2015-05-27 | 弗特鲁斯专业公司 | 用于制备二卤吡啶的方法 |
| CN103145609B (zh) * | 2013-03-05 | 2015-08-05 | 衢州恒顺化工有限公司 | 一种2,3-二氯吡啶的制备方法 |
| CN103193703B (zh) * | 2013-04-26 | 2014-10-15 | 山东天信化工有限公司 | 一种2，3-二氯吡啶的提纯方法 |
| EP2816031A1 (de) | 2013-06-18 | 2014-12-24 | Saltigo GmbH | Verfahren zur Herstellung von 2,3-Dichlorpyridin |
| CN103420903A (zh) * | 2013-09-03 | 2013-12-04 | 天津安锦科技发展有限公司 | 一种合成2,4-二氯-5-溴吡啶的方法 |
| CN103570609B (zh) * | 2013-10-28 | 2015-11-18 | 南通天泽化工有限公司 | 一种2,3-二氯吡啶的制备方法 |
| CN104926715A (zh) * | 2015-06-03 | 2015-09-23 | 安徽绩溪县徽煌化工有限公司 | 一种2,3-二氯吡啶的制备方法 |
| CN111170937A (zh) * | 2020-01-08 | 2020-05-19 | 山东泓达生物科技有限公司 | 一种3-氨基吡啶的制备方法 |
| CN113149896A (zh) * | 2021-03-09 | 2021-07-23 | 利尔化学股份有限公司 | 一种3-氨基吡啶的制备方法 |
| CN113582918B (zh) * | 2021-07-16 | 2023-01-17 | 内蒙古源宏精细化工有限公司 | 氯化制备2,3-二氯吡啶的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1695659B1 (de) * | 1967-12-18 | 1971-12-16 | Ruetgerswerke Ag | Verfahren zur Herstellung von 2-Chlorpyridinen |
| US3838136A (en) * | 1973-01-16 | 1974-09-24 | Abbott Lab | Preparation of 2-chloro-3-aminopyridine |
| IT1017606B (it) * | 1973-06-06 | 1977-08-10 | Basf Ag | Processo per la preparazione di amine e di uree sostituit |
| US4082749A (en) * | 1973-06-06 | 1978-04-04 | Basf Aktiengesellschaft | Process for the production of amines |
-
2005
- 2005-01-07 TW TW094100423A patent/TWI336325B/zh not_active IP Right Cessation
- 2005-01-20 MY MYPI20050242A patent/MY136794A/en unknown
- 2005-01-21 WO PCT/US2005/002462 patent/WO2005070888A2/en not_active Ceased
- 2005-01-21 BR BRPI0506502-0A patent/BRPI0506502A/pt not_active IP Right Cessation
- 2005-01-21 US US10/583,635 patent/US20070161797A1/en not_active Abandoned
- 2005-01-21 RU RU2006130368/04A patent/RU2359960C2/ru not_active IP Right Cessation
- 2005-01-21 MX MXPA06008208A patent/MXPA06008208A/es active IP Right Grant
- 2005-01-21 JP JP2006551437A patent/JP2007523065A/ja active Pending
- 2005-01-21 EP EP05712075A patent/EP1706381A2/en not_active Withdrawn
- 2005-01-21 UA UAA200606998A patent/UA86604C2/ru unknown
- 2005-01-21 ZA ZA200605616A patent/ZA200605616B/en unknown
- 2005-01-21 KR KR1020067014736A patent/KR20060130618A/ko not_active Ceased
- 2005-01-21 AR ARP050100219A patent/AR048217A1/es not_active Application Discontinuation
- 2005-01-21 CA CA002553850A patent/CA2553850A1/en not_active Abandoned
- 2005-01-21 AU AU2005206576A patent/AU2005206576A1/en not_active Abandoned
- 2005-01-21 CN CN2005800026918A patent/CN1910152B/zh not_active Expired - Lifetime
-
2006
- 2006-06-19 IL IL176420A patent/IL176420A/en not_active IP Right Cessation
- 2006-08-22 CO CO06082639A patent/CO5720997A2/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1910152A (zh) | 2007-02-07 |
| UA86604C2 (en) | 2009-05-12 |
| MXPA06008208A (es) | 2006-08-31 |
| US20070161797A1 (en) | 2007-07-12 |
| BRPI0506502A (pt) | 2007-02-27 |
| IL176420A0 (en) | 2006-10-05 |
| TW200533654A (en) | 2005-10-16 |
| KR20060130618A (ko) | 2006-12-19 |
| CA2553850A1 (en) | 2005-08-04 |
| AR048217A1 (es) | 2006-04-12 |
| WO2005070888A2 (en) | 2005-08-04 |
| EP1706381A2 (en) | 2006-10-04 |
| ZA200605616B (en) | 2008-05-28 |
| JP2007523065A (ja) | 2007-08-16 |
| RU2006130368A (ru) | 2008-02-27 |
| RU2359960C2 (ru) | 2009-06-27 |
| CO5720997A2 (es) | 2007-01-31 |
| WO2005070888A3 (en) | 2005-10-20 |
| IL176420A (en) | 2011-05-31 |
| MY136794A (en) | 2008-11-28 |
| AU2005206576A1 (en) | 2005-08-04 |
| CN1910152B (zh) | 2010-07-21 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |