US3892760A - Bis-(2-pyridyl-1-oxide) disulfide - Google Patents
Bis-(2-pyridyl-1-oxide) disulfide Download PDFInfo
- Publication number
- US3892760A US3892760A US466328A US46632874A US3892760A US 3892760 A US3892760 A US 3892760A US 466328 A US466328 A US 466328A US 46632874 A US46632874 A US 46632874A US 3892760 A US3892760 A US 3892760A
- Authority
- US
- United States
- Prior art keywords
- oxide
- alkali metal
- disulfide
- hydrogen peroxide
- bis
- 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 - Lifetime
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 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 29
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 13
- -1 alkali metal salt Chemical class 0.000 claims abstract description 13
- 230000003647 oxidation Effects 0.000 claims abstract description 9
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 9
- 230000001590 oxidative effect Effects 0.000 claims abstract description 9
- 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 6
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 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
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 26
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 159000000000 sodium salts Chemical class 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 7
- 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 description 3
- 239000001744 Sodium fumarate Substances 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- MSJMDZAOKORVFC-SEPHDYHBSA-L disodium fumarate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C\C([O-])=O MSJMDZAOKORVFC-SEPHDYHBSA-L 0.000 claims description 3
- MSJMDZAOKORVFC-UAIGNFCESA-L disodium maleate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C/C([O-])=O MSJMDZAOKORVFC-UAIGNFCESA-L 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229940005573 sodium fumarate Drugs 0.000 claims description 3
- 235000019294 sodium fumarate Nutrition 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 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 7
- 239000000047 product Substances 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 5
- FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical compound [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 description 5
- 238000003556 assay Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 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
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 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
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 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
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 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
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- OATNQHYJXLHTEW-UHFFFAOYSA-N benzene-1,4-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(S(O)(=O)=O)C=C1 OATNQHYJXLHTEW-UHFFFAOYSA-N 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
- 239000004744 fabric Substances 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
- 229960002598 fumaric acid Drugs 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 150000005748 halopyridines Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000000630 rising effect Effects 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
Definitions
- 3,759,932 also generally discloses the preparation of a disulfide compound using an in.-situ preparation technique wherein? mercaptopyridine is not "isolated. -rWh-ile these references broadly disclose the preparati'on' of the disulfide, problems have arisen when using the alkali metal salt of Z-mercaptopyridine-l-oxide in an in-situ technique wherein the alkali metal salt was obtained by oxidizing 2-chloropyridine with permaleic acid ,to form the N- oxide followed by mercaptization to form the salt.
- oxidationby the; known techniques as shown for,example in U.S. Pat. No. 2,742,476 resulted in the formation of undesired by-products such as the alkali metal maleate and alkali-metal fumarate. This contaminated the desired disulfideproduct and lowered the yield.
- drosulfide in accordance with known procedures as disclosed if] Us; Pat. No. 2,686,786.1"he'key step in this invention is the oxidation ofjthe preparedlalkali metal salt of2-mercaptopyridinel' oxide using hydrogen peroxide and a reaction pH of about i to about 5.
- a reaction pH of about i to about 5.
- the hydrogen peroxide concentration may be varied with about 5 to about 30 percent in aqueous solution being generally used. Generally a stoichiometi' ric. ratio of the alkali metal salt of 2-mercaptopyridine and hydrogen peroxide of about 2 moles of the mercaptopyri dine salt to about 1 mole of peroxide or a slight excess of up to about 15 percent peroxide is used.
- the pH of the reaction mixture is generally adjusted before the peroxide oxidation step by using any suitable acidifying agent such as the non-oxidizing mineral acids such as HCl andthe non-oxidizing organic acids.
- the 'disulf ed compounds prepared in accordance with the method of this invention have a variety of known uses, particularly as antibacterialand antifungal agentsin a variety of applications such as to combat agricultural plant diseases, and in plastics and fabrics to resist mildew or other fungus attack as disclosedin U.S. Pat. No. 2,742,476.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Cosmetics (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US466328A US3892760A (en) | 1974-05-02 | 1974-05-02 | Bis-(2-pyridyl-1-oxide) disulfide |
| IL46996A IL46996A (en) | 1974-05-02 | 1975-04-01 | Method for preparing bis-(2-pyridyl-1-oxide)disulfide |
| ZA00752024A ZA752024B (en) | 1974-05-02 | 1975-04-01 | Method for preparing bigs-(2-pyridyl-1-oxide) disufide |
| IE716/75A IE41103B1 (en) | 1974-05-02 | 1975-04-02 | Method for preparing bis-(2-pyridyl-1-oxide) disulfide |
| CA223,892A CA1052792A (en) | 1974-05-02 | 1975-04-04 | Method for preparing bis-(2-pyridyl-1-oxide) disulfide |
| GB1439675A GB1469907A (en) | 1974-05-02 | 1975-04-08 | Method for preparing bis-2-pyridyl-1-oxide- disulphide |
| AU79968/75A AU484367B2 (en) | 1974-05-02 | 1975-04-09 | METHOD FOR PREPARING BIS-(2-PYRIDYL-l-OXIDE DISULFIDE |
| DK168275A DK143650C (da) | 1974-05-02 | 1975-04-18 | Fremgangsmaade til fremstilling af bis-(2-pyridyl-1-oxid)-disulfid |
| NL7504696A NL7504696A (nl) | 1974-05-02 | 1975-04-21 | Werkwijze voor de bereiding van bis(2-pyridyl- -1-oxyde)disulfide. |
| IT49240/75A IT1035419B (it) | 1974-05-02 | 1975-04-22 | Procedimento per la produzione di bis 2 piridil i ossido di sol furo |
| FI751253A FI58917C (fi) | 1974-05-02 | 1975-04-25 | Foerfarande foer framstaellning av bis-(2-pyridyl-1-oxid)disulfid |
| BR3288/75D BR7502591A (pt) | 1974-05-02 | 1975-04-29 | Aperfeicoamento em processo de preparar dissulfeto de bis-(1-oxido de 2-piridila) |
| FR7513649A FR2269525B1 (enrdf_load_stackoverflow) | 1974-05-02 | 1975-04-30 | |
| CH554575A CH597190A5 (enrdf_load_stackoverflow) | 1974-05-02 | 1975-04-30 | |
| JP5307175A JPS5421344B2 (enrdf_load_stackoverflow) | 1974-05-02 | 1975-05-01 | |
| SE7505136A SE401508B (sv) | 1974-05-02 | 1975-05-02 | Forfarande for framstellning av bis(2-pyridyl-1-oxid)-disulfid |
| DE19752519715 DE2519715C3 (de) | 1974-05-02 | 1975-05-02 | Verfahren zur Herstellung von Bis-(2-pyridyl-l-oxid)-disulfid |
| BE156038A BE828695A (fr) | 1974-05-02 | 1975-05-02 | Preparation du bis-(2-pyridyl-1-oxyde) disulfure |
| AR20854677D AR208546A1 (es) | 1974-05-02 | 1977-02-15 | Metodo de preparacion de disulfuro de bis-(2-piridil-1-oxido) |
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 |
|---|---|
| US3892760A true US3892760A (en) | 1975-07-01 |
Family
ID=23851343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US466328A Expired - Lifetime US3892760A (en) | 1974-05-02 | 1974-05-02 | Bis-(2-pyridyl-1-oxide) disulfide |
Country Status (17)
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4504667A (en) * | 1983-06-24 | 1985-03-12 | Olin Corporation | Process for oxidizing halopyridines to halopyridine-N-oxides |
| US4585871A (en) * | 1982-03-26 | 1986-04-29 | Olin Corporation | Process for oxidizing halopyridines to halopyridine-N-oxides |
| 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 |
| US20040171600A1 (en) * | 2001-03-06 | 2004-09-02 | Toshimasa Ohnishi | Antimicrobial compositions |
Citations (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
Patent Citations (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 |
Cited By (5)
| 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 |
| US20040171600A1 (en) * | 2001-03-06 | 2004-09-02 | Toshimasa Ohnishi | Antimicrobial compositions |
| US7416736B2 (en) * | 2001-03-06 | 2008-08-26 | Janssen Pharmaceutica N.V. | Antimicrobial compositions |
| 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 |
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 |
| CA1052792A (en) | 1979-04-17 |
| 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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