SU509222A3 - Способ получени солей 1,11-дизамещенного4,41-дипиридили - Google Patents

Способ получени солей 1,11-дизамещенного4,41-дипиридили

Info

Publication number: SU509222A3
Authority: SU; USSR - Soviet Union
Prior art keywords: tube; ammonia; resulting; solution; sulfur dioxide
Prior art date: 1970-04-03

Application number

SU1637443A

Other languages

English (en)

Russian (ru)

Inventor

Джерард Карей Джон

Original Assignee

Империал Кемикал Индастризлимитед (Фирма)

Priority date (The priority date 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 date listed.)

1970-04-03

Filing date

1971-03-29

Publication date

1976-03-30

1971-03-29 Application filed by Империал Кемикал Индастризлимитед (Фирма) filed Critical Империал Кемикал Индастризлимитед (Фирма)

1976-03-30 Application granted granted Critical

1976-03-30 Publication of SU509222A3 publication Critical patent/SU509222A3/ru

Links

150000003839 salts Chemical class 0.000 title claims description 18
238000000034 method Methods 0.000 title claims description 12
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 31
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 26
238000006243 chemical reaction Methods 0.000 claims description 25
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 22
239000000243 solution Substances 0.000 claims description 16
-1 3,5-dimethylmorpholineacetyl Chemical group 0.000 claims description 9
229910021529 ammonia Inorganic materials 0.000 claims description 8
239000007864 aqueous solution Substances 0.000 claims description 8
239000012299 nitrogen atmosphere Substances 0.000 claims description 8
150000002500 ions Chemical class 0.000 claims description 7
239000007788 liquid Substances 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 7
230000003647 oxidation Effects 0.000 claims description 7
238000007254 oxidation reaction Methods 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
239000000725 suspension Substances 0.000 claims description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
MWVTWFVJZLCBMC-UHFFFAOYSA-N 4,4'-bipyridine Chemical class C1=NC=CC(C=2C=CN=CC=2)=C1 MWVTWFVJZLCBMC-UHFFFAOYSA-N 0.000 claims description 2
238000002474 experimental method Methods 0.000 claims description 2
238000001914 filtration Methods 0.000 claims description 2
239000000047 product Substances 0.000 claims description 2
239000002244 precipitate Substances 0.000 claims 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 2
239000013049 sediment Substances 0.000 claims 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
DPMLZTVWIBNBLI-UHFFFAOYSA-N CC1C=CC=C(N1C)C.I Chemical compound CC1C=CC=C(N1C)C.I DPMLZTVWIBNBLI-UHFFFAOYSA-N 0.000 claims 1
239000013078 crystal Substances 0.000 claims 1
150000002148 esters Chemical class 0.000 claims 1
238000001704 evaporation Methods 0.000 claims 1
230000008020 evaporation Effects 0.000 claims 1
230000003993 interaction Effects 0.000 claims 1
PJPOCNJHYFUPCE-UHFFFAOYSA-N picen-1-ol Chemical compound C1=CC=CC2=C(C=CC=3C4=CC=C5C=CC=C(C=35)O)C4=CC=C21 PJPOCNJHYFUPCE-UHFFFAOYSA-N 0.000 claims 1
238000001953 recrystallisation Methods 0.000 claims 1
238000000926 separation method Methods 0.000 claims 1
239000011541 reaction mixture Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000007800 oxidant agent Substances 0.000 description 6
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
239000013067 intermediate product Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
238000003756 stirring Methods 0.000 description 3
MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
235000013877 carbamide Nutrition 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
239000003880 polar aprotic solvent Substances 0.000 description 2
238000002798 spectrophotometry method Methods 0.000 description 2
YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
QAIGYXWRIHZZAA-UHFFFAOYSA-M 1-methylpyridin-1-ium;chloride Chemical compound [Cl-].C[N+]1=CC=CC=C1 QAIGYXWRIHZZAA-UHFFFAOYSA-M 0.000 description 1
ZRQWXZLJRJZNJO-UHFFFAOYSA-M 2-pyridin-1-ium-1-ylethanol;chloride Chemical compound [Cl-].OCC[N+]1=CC=CC=C1 ZRQWXZLJRJZNJO-UHFFFAOYSA-M 0.000 description 1
WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241001133287 Artocarpus hirsutus Species 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
206010011703 Cyanosis Diseases 0.000 description 1
GRWPXSTZEBUPPR-UHFFFAOYSA-N N#CC#N.CC(=O)C Chemical compound N#CC#N.CC(=O)C GRWPXSTZEBUPPR-UHFFFAOYSA-N 0.000 description 1
ITTMYLVSYMQVQB-UHFFFAOYSA-N O=S=O.O=S=O Chemical compound O=S=O.O=S=O ITTMYLVSYMQVQB-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
150000004056 anthraquinones Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000007844 bleaching agent Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
OZECDDHOAMNMQI-UHFFFAOYSA-H cerium(3+);trisulfate Chemical compound [Ce+3].[Ce+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O OZECDDHOAMNMQI-UHFFFAOYSA-H 0.000 description 1
239000007806 chemical reaction intermediate Substances 0.000 description 1
OSVXSBDYLRYLIG-UHFFFAOYSA-N chlorine dioxide Inorganic materials O=Cl=O OSVXSBDYLRYLIG-UHFFFAOYSA-N 0.000 description 1
235000019398 chlorine dioxide Nutrition 0.000 description 1
210000004081 cilia Anatomy 0.000 description 1
230000007423 decrease Effects 0.000 description 1
ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical class Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229910001867 inorganic solvent Inorganic materials 0.000 description 1
239000003049 inorganic solvent Substances 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
125000005429 oxyalkyl group Chemical group 0.000 description 1
150000002926 oxygen Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
150000004053 quinones Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1

Landscapes

Pyridine Compounds (AREA)

SU1637443A 1970-04-03 1971-03-29 Способ получени солей 1,11-дизамещенного4,41-дипиридили SU509222A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB1596070		1970-04-03

Publications (1)

Publication Number	Publication Date
SU509222A3 true SU509222A3 (ru)	1976-03-30

Family

ID=10068680

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU1637443A SU509222A3 (ru)	1970-04-03	1971-03-29	Способ получени солей 1,11-дизамещенного4,41-дипиридили

Country Status (8)

Country	Link
ES (1)	ES389879A2 (2)
HU (1)	HU164619B (2)
IE (1)	IE35140B1 (2)
IT (1)	IT1044919B (2)
PL (1)	PL87147B1 (2)
RO (1)	RO59996A7 (2)
SU (1)	SU509222A3 (2)
ZA (1)	ZA711864B (2)

1971
- 1971-03-19 IE IE35071A patent/IE35140B1/xx unknown
- 1971-03-23 ZA ZA711864A patent/ZA711864B/xx unknown
- 1971-03-23 PL PL14708871A patent/PL87147B1/pl unknown
- 1971-03-29 SU SU1637443A patent/SU509222A3/ru active
- 1971-03-31 IT IT2257771A patent/IT1044919B/it active
- 1971-04-02 HU HUIE000445 patent/HU164619B/hu unknown
- 1971-04-03 ES ES389879A patent/ES389879A2/es not_active Expired
- 1971-04-03 RO RO6647171A patent/RO59996A7/ro unknown

Also Published As

Publication number	Publication date
HU164619B (2)	1974-03-28
ZA711864B (en)	1971-12-29
IT1044919B (it)	1980-04-21
IE35140B1 (en)	1975-11-26
RO59996A7 (2)	1976-06-15
PL87147B1 (en)	1976-06-30
IE35140L (en)	1971-10-03
ES389879A2 (es)	1973-06-16

Publication	Publication Date	Title
Hopkins et al.	2017	Formation of N-sulfonyl imines from iminoiodinanes by iodine-promoted, N-centered radical sulfonamidation of aldehydes
Gasnot et al.	2020	Taming the Reactivity of Phosphiranium Salts: Site‐Selective C‐Centered Ring Opening for Direct Synthesis of Phosphinoethylamines
Fasani et al.	2001	Unexpected photoreactions of some 7‐amino‐6‐fluoroquinolones in phosphate buffer
US2766243A (en)	1956-10-09	Acyclic, polynitrile-containing, unsaturated compound and its salts, and preparation thereof
SU509222A3 (ru)	1976-03-30	Способ получени солей 1,11-дизамещенного4,41-дипиридили
US3755337A (en)	1973-08-28	Manufacture of 1,1-disubstituted-4,4-bipyridylium salts
Itoh et al.	2000	Radical scavenging by N-aminoazaaromatics
US2315534A (en)	1943-04-06	Preparation of ammonium thiosulphates
US3793335A (en)	1974-02-19	Manufacture of 1,1'-disubstituted-4,4'-bipyridylium salts and related compounds
US2889366A (en)	1959-06-02	Substituted alkyl hydrazinium chlorides
Okamoto et al.	1963	Reaction of N-Aminopyridinium Derivatives. II. The Reactions of 1-(N-Acylalkylamino) pyridinium Salt Derivatives with Cyanide Ion.: A New Synthesis of Primary Amines.
Kharasch	1921	AN INDIRECT METHOD OF PREPARATION OF ORGANIC MERCURIC DERIVATIVES AND A METHOD OF LINKING CARBON TO CARBON. Preliminary Report.
Lüning et al.	1991	Concave reagents, 8. Concave pyridines and 1, 10‐phenanthrolines with sulfonamide bridgeheads. Increased basicity by 4‐diethylamino substitution of the pyridine unit
US3905986A (en)	1975-09-16	Manufacture of 1,1-disubstituted-4,4-bipyridylium salts
US3868381A (en)	1975-02-25	Manufacture of 1,1-disubstituted-4,4 -bipyridylium
US3046278A (en)	1962-07-24	Process of cyanation
US3790585A (en)	1974-02-05	Manufacture of bipyridylium salts
US3864352A (en)	1975-02-04	Manufacture of bipyridylium salts
US3272833A (en)	1966-09-13	Certain substituted 5-nitro-2-furylamidoximes
Ogata et al.	1971	Photodecomposition of 1-substituted 3, 4-dihydroisoquinolines
US3723444A (en)	1973-03-27	Manufacturing of bipyridylium salts
US3622477A (en)	1971-11-23	Synthesis of n:n{40 -distributed bipyridylium salts
JPH04321609A (ja)	1992-11-11	イソチアゾリノン製剤の安定化における改良
SU490288A3 (ru)	1975-10-30	Способ получени соли 1,1"-ди/оксиалкил/-4,4"бипиридила
PL89660B1 (2)	1976-12-31