IL32455A - Manufacture of bipyridylium salts - Google Patents
Manufacture of bipyridylium saltsInfo
- Publication number
- IL32455A IL32455A IL32455A IL3245569A IL32455A IL 32455 A IL32455 A IL 32455A IL 32455 A IL32455 A IL 32455A IL 3245569 A IL3245569 A IL 3245569A IL 32455 A IL32455 A IL 32455A
- Authority
- IL
- Israel
- Prior art keywords
- salt
- bipyridylium
- cyano
- employed
- reaction mixture
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 34
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 238000000034 method Methods 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 47
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 26
- -1 N-substituted-4-cyano pyridinium salt Chemical class 0.000 claims description 21
- 150000001768 cations Chemical class 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 14
- 239000007800 oxidant agent Substances 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- REJHVSOVQBJEBF-OWOJBTEDSA-N 5-azaniumyl-2-[(e)-2-(4-azaniumyl-2-sulfonatophenyl)ethenyl]benzenesulfonate Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1\C=C\C1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-OWOJBTEDSA-N 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- AQHLWAARHKACOY-UHFFFAOYSA-N Amsonic acid Natural products N1C2=CC=CC=C2C2=C1C1CC3C(C(O)=O)COC(C)(O)C3CN1CC2 AQHLWAARHKACOY-UHFFFAOYSA-N 0.000 claims description 9
- 230000003993 interaction Effects 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 6
- 239000003729 cation exchange resin Substances 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229910001448 ferrous ion Inorganic materials 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000004291 sulphur dioxide Substances 0.000 claims description 2
- 235000010269 sulphur dioxide Nutrition 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical group [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims 1
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical class Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 claims 1
- 229910001447 ferric ion Inorganic materials 0.000 claims 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims 1
- 239000000243 solution Substances 0.000 description 12
- 150000002500 ions Chemical class 0.000 description 9
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229950003153 amsonate Drugs 0.000 description 3
- 229940023913 cation exchange resins Drugs 0.000 description 3
- 229920001429 chelating resin Polymers 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
- AYBRYHGEIXONDD-UHFFFAOYSA-N 4,5-bis(2-methylpropoxy)imidazolidin-2-one Chemical compound CC(C)COC1NC(=O)NC1OCC(C)C AYBRYHGEIXONDD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 238000004435 EPR spectroscopy Methods 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 125000000129 anionic group Chemical group 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
- 238000009835 boiling Methods 0.000 description 1
- 229940045348 brown mixture Drugs 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 238000012505 colouration Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 150000002170 ethers Chemical class 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
- 150000004688 heptahydrates Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- INFDPOAKFNIJBF-UHFFFAOYSA-N paraquat Chemical compound C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 INFDPOAKFNIJBF-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- BJDYCCHRZIFCGN-UHFFFAOYSA-N pyridin-1-ium;iodide Chemical compound I.C1=CC=NC=C1 BJDYCCHRZIFCGN-UHFFFAOYSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB31366/68A GB1277734A (en) | 1968-07-01 | 1968-07-01 | Manufacture of bipyridylium salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL32455A0 IL32455A0 (en) | 1969-08-27 |
| IL32455A true IL32455A (en) | 1972-12-29 |
Family
ID=10322037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL32455A IL32455A (en) | 1968-07-01 | 1969-06-23 | Manufacture of bipyridylium salts |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3723444A (ro) |
| AT (1) | AT290537B (ro) |
| BE (1) | BE735349A (ro) |
| BR (1) | BR6910358D0 (ro) |
| CA (1) | CA929524A (ro) |
| CH (1) | CH518280A (ro) |
| DE (1) | DE1933418A1 (ro) |
| DK (1) | DK127296B (ro) |
| ES (1) | ES368994A1 (ro) |
| FR (1) | FR2012113A1 (ro) |
| GB (1) | GB1277734A (ro) |
| IE (1) | IE33390B1 (ro) |
| IL (1) | IL32455A (ro) |
| NL (1) | NL6910049A (ro) |
| RO (1) | RO55857A (ro) |
| ZA (1) | ZA694331B (ro) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1406881A (en) * | 1972-04-13 | 1975-09-17 | Ici Ltd | Herbicidal compositions |
| US6057267A (en) * | 1997-12-05 | 2000-05-02 | Henkel Corporation | Use of fatty alcohol carbonates as solvents in agricultural formulations |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1073081A (en) * | 1964-04-09 | 1967-06-21 | Ici Ltd | Production of bis-quaternary salts of 4:4'-bipyridyls |
-
1968
- 1968-07-01 GB GB31366/68A patent/GB1277734A/en not_active Expired
-
1969
- 1969-06-03 RO RO60384A patent/RO55857A/ro unknown
- 1969-06-12 IE IE806/69A patent/IE33390B1/xx unknown
- 1969-06-13 CA CA054334A patent/CA929524A/en not_active Expired
- 1969-06-16 US US00833710A patent/US3723444A/en not_active Expired - Lifetime
- 1969-06-18 ZA ZA694331A patent/ZA694331B/xx unknown
- 1969-06-23 IL IL32455A patent/IL32455A/en unknown
- 1969-06-27 BE BE735349D patent/BE735349A/xx unknown
- 1969-06-27 AT AT615269A patent/AT290537B/de not_active IP Right Cessation
- 1969-06-30 CH CH1000069A patent/CH518280A/de not_active IP Right Cessation
- 1969-07-01 BR BR210358/69A patent/BR6910358D0/pt unknown
- 1969-07-01 NL NL6910049A patent/NL6910049A/xx unknown
- 1969-07-01 DK DK356269AA patent/DK127296B/da unknown
- 1969-07-01 ES ES368994A patent/ES368994A1/es not_active Expired
- 1969-07-01 DE DE19691933418 patent/DE1933418A1/de active Pending
- 1969-07-01 FR FR6922223A patent/FR2012113A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CA929524A (en) | 1973-07-03 |
| GB1277734A (en) | 1972-06-14 |
| AT290537B (de) | 1971-06-11 |
| ZA694331B (en) | 1971-02-24 |
| DE1933418A1 (de) | 1970-01-15 |
| IE33390B1 (en) | 1974-06-12 |
| DK127296B (da) | 1973-10-15 |
| ES368994A1 (es) | 1971-05-16 |
| US3723444A (en) | 1973-03-27 |
| BE735349A (ro) | 1969-12-29 |
| IE33390L (en) | 1970-01-01 |
| CH518280A (de) | 1972-01-31 |
| BR6910358D0 (pt) | 1973-01-09 |
| NL6910049A (ro) | 1970-01-05 |
| IL32455A0 (en) | 1969-08-27 |
| RO55857A (ro) | 1973-11-20 |
| FR2012113A1 (ro) | 1970-03-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4424390A (en) | Process for producing 5-halomethylfurfural | |
| US3967956A (en) | Separation of noble metals | |
| US1822016A (en) | Separation of organic acids | |
| IL24158A (en) | Method for preparing metal salts | |
| IL32455A (en) | Manufacture of bipyridylium salts | |
| Bemporad et al. | Nucleophilic heteroaromatic substitution. XXXI. Meisenheimer-type compounds from heteroaromatic substrates. The reaction of methoxide ion with 3, 5-dinitro-4-methoxypyridine in methanol solution | |
| US3790585A (en) | Manufacture of bipyridylium salts | |
| US3899499A (en) | Manufacture of bipyridylium salts | |
| US3899500A (en) | Manufacture of bipyridylium salts | |
| US3793319A (en) | Manufacture of 1,1'-disubstituted-4,4'-bipyridylium salts | |
| US3755337A (en) | Manufacture of 1,1-disubstituted-4,4-bipyridylium salts | |
| US4025518A (en) | Process for preparing quinacridonequinone by oxidation of dihydroquinacridone | |
| US3254948A (en) | Process of removing iron from aluminum salt solutions | |
| Oki et al. | The role of perchlorate ion in the chloroform extraction of zinc with oxine | |
| US3787426A (en) | Manufacture of 1,1-disubstituted-4,4-bipyridylium salts | |
| US3793335A (en) | Manufacture of 1,1'-disubstituted-4,4'-bipyridylium salts and related compounds | |
| US3905986A (en) | Manufacture of 1,1-disubstituted-4,4-bipyridylium salts | |
| Pocker et al. | Radiochlorine Exchange and Racemization of 1-Phenylethyl Chloride and p-Methylbenzhydryl Chloride in Nitromethane | |
| NL8003565A (nl) | Werkwijze ter bereiding van een 1,1'-digesubstitueerd 4,4'-bipyridyliumzout. | |
| NL8003564A (nl) | Werkwijze ter bereiding van een 1,1'-digesubstitueerd 4,4'-bipyridyliumzout. | |
| US3864352A (en) | Manufacture of bipyridylium salts | |
| US2487874A (en) | Recovery of pyridine carboxylic acid | |
| GB1270863A (en) | Bipyridylium salts | |
| US3886172A (en) | Manufacture of bipyridylium salts | |
| NL8500042A (nl) | Werkwijze ter bereiding van een 1,1'-digesubstitueerd 4,4'-bipyridyliumzout. |