CA1052792A - Method for preparing bis-(2-pyridyl-1-oxide) disulfide - Google Patents
Method for preparing bis-(2-pyridyl-1-oxide) disulfideInfo
- Publication number
- CA1052792A CA1052792A CA223,892A CA223892A CA1052792A CA 1052792 A CA1052792 A CA 1052792A CA 223892 A CA223892 A CA 223892A CA 1052792 A CA1052792 A CA 1052792A
- Authority
- CA
- Canada
- Prior art keywords
- oxide
- alkali metal
- disulfide
- pyridyl
- hydrogen peroxide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- ZHDBTKPXEJDTTQ-UHFFFAOYSA-N dipyrithione Chemical compound [O-][N+]1=CC=CC=C1SSC1=CC=CC=[N+]1[O-] ZHDBTKPXEJDTTQ-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title claims description 21
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 25
- -1 alkali metal salt Chemical class 0.000 claims abstract description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 11
- 230000003647 oxidation Effects 0.000 claims abstract description 10
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 10
- DZKRDHLYQRTDBU-UPHRSURJSA-N (z)-but-2-enediperoxoic acid Chemical compound OOC(=O)\C=C/C(=O)OO DZKRDHLYQRTDBU-UPHRSURJSA-N 0.000 claims abstract description 8
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 claims abstract description 8
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000001590 oxidative effect Effects 0.000 claims abstract description 6
- WYSRTEVFLQJJDN-UHFFFAOYSA-N 2-chloro-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1Cl WYSRTEVFLQJJDN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052977 alkali metal sulfide Inorganic materials 0.000 claims abstract description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 4
- 239000001744 Sodium fumarate Substances 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- MSJMDZAOKORVFC-SEPHDYHBSA-L disodium fumarate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C\C([O-])=O MSJMDZAOKORVFC-SEPHDYHBSA-L 0.000 claims description 2
- MSJMDZAOKORVFC-UAIGNFCESA-L disodium maleate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C/C([O-])=O MSJMDZAOKORVFC-UAIGNFCESA-L 0.000 claims description 2
- 229940005573 sodium fumarate Drugs 0.000 claims description 2
- 235000019294 sodium fumarate Nutrition 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 150000001204 N-oxides Chemical class 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical compound [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 150000005749 2-halopyridines Chemical class 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229940050411 fumarate Drugs 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000005748 halopyridines Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material 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
- C07D213/89—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 with hetero atoms directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US466328A US3892760A (en) | 1974-05-02 | 1974-05-02 | Bis-(2-pyridyl-1-oxide) disulfide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1052792A true CA1052792A (en) | 1979-04-17 |
Family
ID=23851343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA223,892A Expired CA1052792A (en) | 1974-05-02 | 1975-04-04 | Method for preparing bis-(2-pyridyl-1-oxide) disulfide |
Country Status (17)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4585871A (en) * | 1982-03-26 | 1986-04-29 | Olin Corporation | Process for oxidizing halopyridines to halopyridine-N-oxides |
| US4504667A (en) * | 1983-06-24 | 1985-03-12 | Olin Corporation | Process for oxidizing halopyridines to halopyridine-N-oxides |
| JP2002265310A (ja) * | 2001-03-06 | 2002-09-18 | Nagase Chemtex Corp | 抗微生物剤組成物 |
| US6664280B2 (en) | 2001-07-25 | 2003-12-16 | The United States Of America As Represented By The Secretary Of The Army | Antivesicant compounds and methods of making and using thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2686786A (en) * | 1953-01-09 | 1954-08-17 | Olin Mathieson | Nu-hydroxy-2-pyridinethiones and method of preparing same |
| US2742476A (en) * | 1953-10-26 | 1956-04-17 | Olin Mathieson | Derivatives of 2-mercaptopyridine 1-oxide |
| US2951844A (en) * | 1958-11-05 | 1960-09-06 | Olin Mathieson | Cyclic process for manufacture of 2-chloropyridine-1-oxide |
| US3759932A (en) * | 1972-08-25 | 1973-09-18 | Olin Corp | Method for preparing mercaptopyridines using alkali metal polysulfides |
-
1974
- 1974-05-02 US US466328A patent/US3892760A/en not_active Expired - Lifetime
-
1975
- 1975-04-01 ZA ZA00752024A patent/ZA752024B/xx unknown
- 1975-04-01 IL IL46996A patent/IL46996A/en unknown
- 1975-04-02 IE IE716/75A patent/IE41103B1/xx unknown
- 1975-04-04 CA CA223,892A patent/CA1052792A/en not_active Expired
- 1975-04-08 GB GB1439675A patent/GB1469907A/en not_active Expired
- 1975-04-18 DK DK168275A patent/DK143650C/da not_active IP Right Cessation
- 1975-04-21 NL NL7504696A patent/NL7504696A/xx not_active Application Discontinuation
- 1975-04-22 IT IT49240/75A patent/IT1035419B/it active
- 1975-04-25 FI FI751253A patent/FI58917C/fi not_active IP Right Cessation
- 1975-04-29 BR BR3288/75D patent/BR7502591A/pt unknown
- 1975-04-30 CH CH554575A patent/CH597190A5/xx not_active IP Right Cessation
- 1975-04-30 FR FR7513649A patent/FR2269525B1/fr not_active Expired
- 1975-05-01 JP JP5307175A patent/JPS5421344B2/ja not_active Expired
- 1975-05-02 BE BE156038A patent/BE828695A/xx unknown
- 1975-05-02 SE SE7505136A patent/SE401508B/xx unknown
-
1977
- 1977-02-15 AR AR20854677D patent/AR208546A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| BE828695A (fr) | 1975-11-03 |
| FI58917B (fi) | 1981-01-30 |
| IT1035419B (it) | 1979-10-20 |
| AR208546A1 (es) | 1977-02-15 |
| FR2269525B1 (enrdf_load_stackoverflow) | 1979-10-05 |
| DK143650C (da) | 1982-02-15 |
| IL46996A (en) | 1977-12-30 |
| IE41103L (en) | 1975-11-02 |
| FR2269525A1 (enrdf_load_stackoverflow) | 1975-11-28 |
| JPS5421344B2 (enrdf_load_stackoverflow) | 1979-07-30 |
| FI751253A7 (enrdf_load_stackoverflow) | 1975-11-03 |
| DK143650B (da) | 1981-09-21 |
| CH597190A5 (enrdf_load_stackoverflow) | 1978-03-31 |
| AU7996875A (en) | 1976-10-14 |
| DK168275A (da) | 1975-11-03 |
| FI58917C (fi) | 1981-05-11 |
| NL7504696A (nl) | 1975-11-04 |
| GB1469907A (en) | 1977-04-06 |
| BR7502591A (pt) | 1976-03-16 |
| ZA752024B (en) | 1976-02-25 |
| DE2519715A1 (de) | 1975-11-06 |
| SE7505136L (sv) | 1975-11-03 |
| IE41103B1 (en) | 1979-10-24 |
| US3892760A (en) | 1975-07-01 |
| JPS50149680A (enrdf_load_stackoverflow) | 1975-11-29 |
| DE2519715B2 (de) | 1977-03-31 |
| IL46996A0 (en) | 1975-06-25 |
| SE401508B (sv) | 1978-05-16 |
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