CA1232277A - Process for the production of 2,5-bis- (hydrocarbyldithio-1,3,4-thiadiazoles - Google Patents
Process for the production of 2,5-bis- (hydrocarbyldithio-1,3,4-thiadiazolesInfo
- Publication number
- CA1232277A CA1232277A CA000461741A CA461741A CA1232277A CA 1232277 A CA1232277 A CA 1232277A CA 000461741 A CA000461741 A CA 000461741A CA 461741 A CA461741 A CA 461741A CA 1232277 A CA1232277 A CA 1232277A
- Authority
- CA
- Canada
- Prior art keywords
- bis
- production
- hydrogen peroxide
- thiadiazoles
- hydrocarbyldithio
- 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
- 238000000034 method Methods 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- -1 hydrocarbyl mercaptan Chemical compound 0.000 abstract 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 1
- ZBADMMCYTSORHN-UHFFFAOYSA-N 2,5-bis(dodecyldisulfanyl)-1,3,4-thiadiazole Chemical compound CCCCCCCCCCCCSSC1=NN=C(SSCCCCCCCCCCCC)S1 ZBADMMCYTSORHN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- 238000011158 quantitative evaluation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833330918 DE3330918A1 (de) | 1983-08-27 | 1983-08-27 | Verfahren zur herstellung von 2,5-bis-(hydrocarbyldithio)-1,3,4-thiadiazolen |
| DEP3330918.3 | 1983-08-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1232277A true CA1232277A (en) | 1988-02-02 |
Family
ID=6207576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000461741A Expired CA1232277A (en) | 1983-08-27 | 1984-08-24 | Process for the production of 2,5-bis- (hydrocarbyldithio-1,3,4-thiadiazoles |
Country Status (5)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10647939B2 (en) * | 2016-11-18 | 2020-05-12 | International Petroleum Products & Additives Company, Inc. | Thiadiazole components, compositions, and methods |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3087932A (en) * | 1959-07-09 | 1963-04-30 | Standard Oil Co | Process for preparing 2, 5-bis(hydrocarbondithio)-1, 3, 4-thiadiazole |
| US3663561A (en) * | 1969-12-29 | 1972-05-16 | Standard Oil Co | 2-hydrocarbyldithio - 5 - mercapto-1,3,4-thiadiazoles and their preparation |
-
1983
- 1983-08-27 DE DE19833330918 patent/DE3330918A1/de not_active Withdrawn
-
1984
- 1984-08-16 EP EP84109743A patent/EP0135778B1/de not_active Expired
- 1984-08-16 AT AT84109743T patent/ATE37363T1/de not_active IP Right Cessation
- 1984-08-16 DE DE8484109743T patent/DE3474142D1/de not_active Expired
- 1984-08-22 JP JP59173442A patent/JPS6061577A/ja active Granted
- 1984-08-24 CA CA000461741A patent/CA1232277A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0135778A3 (en) | 1985-09-25 |
| JPH0533706B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-05-20 |
| EP0135778A2 (de) | 1985-04-03 |
| DE3330918A1 (de) | 1985-03-07 |
| EP0135778B1 (de) | 1988-09-21 |
| DE3474142D1 (en) | 1988-10-27 |
| ATE37363T1 (de) | 1988-10-15 |
| JPS6061577A (ja) | 1985-04-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |